# Signed > Portfolio tracking for angel investors Signed is a portfolio management and performance tracking application designed for angel investors, small fund managers, and startup employees. It automates the tedious parts of managing startup investments so you can focus on what matters. ## Who Is Signed For? - **Angel investors** tracking personal startup investments - **Small fund managers** managing portfolios across multiple entities - **Startup employees** tracking equity and options across companies they've worked at ## Core Features ### Portfolio Tracking and Performance Analytics Track your startup investments across companies, funds, and SPVs. Signed calculates key performance metrics including IRR (Internal Rate of Return), TVPI (Total Value to Paid-In), and DPI (Distributions to Paid-In) automatically. View portfolio value over time, asset allocation breakdowns, and per-investment performance. ### AI-Powered Diligence Upload pitch decks, financial documents, and other materials for AI-powered analysis. Get structured summaries and insights to speed up your due diligence process. ### Investor Update Management Receive and organize investor updates from your portfolio companies in one place. Track company progress, key metrics, and milestones without digging through email. ### Pitch Triage and Submission Portal Set up a public pitch submission portal so founders can send you deals directly. Review, rate, and triage incoming pitches efficiently. ### Tax Reporting Generate tax-ready reports for your startup investments. Track cost basis, distributions, and realized/unrealized gains. ### Team Collaboration Collaborate with co-investors, partners, or advisors. Share notes, emails, and attachments on specific companies. Manage multiple investment entities with team access. ### Public Investor Profiles and Directory Create a public profile showcasing your investment interests, check sizes, and portfolio. Browse the investor directory to find investors by category. ### MCP Server Connect an AI assistant to your Signed account through the MCP (Model Context Protocol) server at https://mcp.signed.com. Works with claude.ai, Claude Desktop, Claude Code, Cursor, and any MCP client: paste the URL into the client's connector settings and it will walk you through authorizing with OAuth. Tools cover portfolio value and performance (IRR, TVPI, DPI), companies, pitches, notes, follows, and public investor profiles; your assistant can also jot a note or log an investment for you, everything else is read-only, and connections can be revoked any time from Settings. ### Public MCP Server (no account needed) The angel investor directory is also an MCP server at https://mcp.signed.com/investors, with no sign-in, OAuth, or token: add the URL to any MCP client with authentication set to none, or POST JSON-RPC 2.0 to it directly. Tools: search_investors (keyword, sector, check size), list_investors (browse by sector or check size, most complete profiles first), get_investor (one public profile: bio, investment focus, links, pinned portfolio companies, pitch submission form if they take pitches, follower counts, similar investors), list_investor_followers, list_investor_following, list_sectors, and list_check_sizes. Only investors who made their Signed profile public appear; it is read-only and rate limited per address. The page at that URL documents every tool's arguments with a sample request. ## Public Pages - [Home](https://signed.com/) - Main landing page with product overview - [About](https://signed.com/about) - Background on Signed and founder Zach Holman - [Pricing](https://signed.com/pricing) - Plans and what each tier includes - [Blog](https://signed.com/blog) - Product updates, insights, and guides - [Contact](https://signed.com/contact) - Get in touch - [Privacy](https://signed.com/privacy) - Privacy policy - [Investor Directory](https://signed.com/investors) - Browse investors by category - [Learn Center](https://signed.com/learn) - Guides and resources for angel investors covering investing basics, entity setup, taxes, and portfolio management - [Tools](https://signed.com/tools) - Free calculators for angel investors, open to anyone without an account - [QSBS Calculator](https://signed.com/tools/qsbs-calculator) - Estimates the Section 1202 gain exclusion for a single position. Routes stock to the correct regime by acquisition date: stock acquired after July 4, 2025 gets the One Big Beautiful Bill Act's tiered exclusion (50% at three years, 75% at four, 100% at five), a $15M per-issuer cap, and a $75M gross assets ceiling; stock acquired on or before that date keeps the pre-OBBBA rules (100% at five years, $10M cap, $50M ceiling). Reports excluded gain, taxable gain, federal tax, state tax, and the date the next exclusion tier opens. Also models state conformity, which is date-dependent: California, Pennsylvania, Alabama, Mississippi, and Oregon (from January 1, 2026) tax the gain the federal exclusion removes; New Jersey conformed on January 1, 2026; Hawaii conforms only to the old 50% exclusion. Non-US taxpayers are told the exclusion generally doesn't apply to them. ## Learn Center Articles ### Help with Signed #### Building Your Angel Investor Profile https://signed.com/learn/articles/building-your-angel-investor-profile Establishing your presence as an angel investor goes beyond cutting checks. A public profile helps you build credibility, attract interesting deals, and connect with founders and fellow investors. On Signed, you can easily set up a public page (for example, signed.com/@holman) to showcase your investing activity and interests — all on your terms. Why Have a Public Investor Profile? Think of your public page as your digital business card in the startup world. By highlighting select deals and sharing a bit about yourself, you make it easier for founders to find you and understand what you're looking for. You might even catch the eye of other investors with similar interests, sparking new connections or syndicate opportunities. Plus, it gives you a place to direct people when someone inevitably asks, “So, what do you invest in?” Features of Your Signed Public Page Within your Signed settings, you can enable a public profile with just a few clicks. Once it's live, you have control over what appears: • Custom handle: Choose your personalized URL (e.g., signed.com/@yourname). • Featured investments: Select which deals to make public, showing off your favorite portfolio companies or verticals. • Bio & interests: Share a short description, areas of focus, and other relevant details founders or co-investors might want to know. • Pitch submissions: Let founders send you their startup pitches directly via your public page, streamlining your inbound deal flow. For more on this, see Receive Startup Pitches from Founders. How to Enable (and Curate) Your Profile Head to your Signed account settings and look for the public profile section. You can toggle visibility on or off at any time. From there, pick which deals you want to highlight and write a short blurb about yourself. You stay in control — nothing goes public unless you decide it should. Growing Your Reputation Having a public investor profile helps you stand out in a sea of anonymous checks. When founders can see your track record and interests, they're more likely to reach out with relevant pitches. Over time, your Signed public page can become a valuable part of your personal investor brand — no search engine optimization wizardry required (but it doesn’t hurt). #### Exporting your AngelList investment portfolio https://signed.com/learn/articles/exporting-your-angellist-investment-portfolio If you've made angel investments through AngelList, you might want a clearer, more detailed view of your portfolio than their dashboard provides. Signed lets you import your AngelList holdings and start tracking performance, history, and analytics all in one place. Step 1: Export Your AngelList Portfolio First, log in to your AngelList account. Head to the Portfolio page. Scroll down until you see your table of holdings. There, you’ll find an Export CSV button—usually right in the middle of the page. Click this button to download a CSV file containing your current AngelList investments. Step 2: Upload to Signed Once you’ve grabbed your AngelList CSV, you can upload it on our Import page. Click to select, or drag and drop to upload your CSV. We'll churn through your CSV and take a look if we can match them to existing companies in your portfolio. Before dropping all your AngelList investments into your Signed investments, we'll give you a confirmation step to make sure everything looks good, or to massage the data a bit better to match up with your portfolio. There's also a rollback, too- so if you do import and it suddenly looks super odd everywhere... head back to the Import page and click the Revert Import button to roll it back. The goal is to be able to add new data as you go, but still be able to bail out so you don't muck up any data. Keep on importing The importer itself is idempotent, meaning you can keep uploading your portfolio from AngelList whenever you'd like and we'll make sure to only update what's changed. This is actually pretty helpful: valuation changes in AngelList are pretty hidden and mysterious, so by bringing your CSV into Signed on a semi-regular basis, you can check the Timeline to get an explicit breakdown of which investments got marked up, which got marked down, and which exited. Many investors have a regular "monthly update" kind of routine to handle these manual steps: maybe once a month they'll do the manual export from AngelList or other third-party services, dump them into Signed, and get a freshly up-to-date portfolio thereafter. It's a nice time to take stock of all your investments and future plans, too! #### Forward Your Emails into Signed: inbox@signed.com https://signed.com/learn/articles/email-forwarding Your inbox is already the system of record for your angel portfolio — pitches land there, founder updates land there, term sheets land there. Signed has a single address that turns that pile back into structured data: inbox@signed.com. Forward anything investing-related to that address and we'll do the parsing on the other side. You don't need to clean it up, strip the forwarding headers, or pick a category first. Just hit forward. What you can send There are two main flavors of email worth forwarding: • Pitches and intros. A founder cold-emailing you, a friend introducing a company, a deck attached to a "thoughts?" one-liner — any of these will land in your pitch queue, with the company, founders, round details, and deck pulled out automatically. If a PDF deck is attached, we'll keep it on the pitch so you don't have to go dig through your inbox later. • Investor updates. The monthly or quarterly notes founders send to their cap table. Forward them in and they'll show up on that company's timeline, so the next time you open the company page you can scroll back through every update they've ever sent — not just the one you happen to remember. You don't need to flag which is which. A short LLM pass figures it out from the content of the email itself. Who you can send it from Forwarded mail has to come from an email address that's tied to your Signed account, otherwise we have no way to know which portfolio it belongs to. Your primary account email works out of the box. If you triage deals from more than one inbox — a personal Gmail, a fund address, a Superhuman alias — add the others under Settings → Emails. Each one needs a quick verification click, and after that you can forward from any of them and it'll end up in the same place. If a forward ever bounces back, the most common reason is that you sent it from an unverified address. We'll email you back with a heads-up so you don't have to wonder where it went. A few practical tips Apple Mail and Gmail both add their own quoting around forwarded messages, and that's fine — the parser is built to handle it. You don't need to clean up the email before sending. If you want a frictionless workflow, set up a filter in your mail client that auto-forwards anything from a portfolio company's domain straight to inbox@signed.com. New update lands in your inbox, copy lands on the company timeline, no extra clicks. Other Signed users have done well with an updates@ inbox on their domain, which auto-forwards all investor updates into Signed from that mailbox. And if you're testing it out for the first time, send yourself a quick forward and check the Pitches or company page a minute later. The round trip is usually fast enough that you'll see it before you've finished refilling your coffee. #### How Multiple Currencies Work in Signed https://signed.com/learn/articles/multiple-currencies Signed tracks investments in 30 currencies. You can have a check in euros, another in pounds and a third in Singapore dollars, and still see one total for the whole portfolio. This guide covers how that works: which currency each figure is in, which exchange rate applies when, and what happens when you change something. If you only need the short version: • Every investment stays in the currency you made it in. • Your portfolio adds up in your home currency, which you set in Settings. • Cost basis converts once, at the rate on the day the money moved, and stays fixed. • Current value converts at today's rate, so returns in your home currency include currency movements. Three currencies Any figure in Signed belongs to one of three currencies. The check's currency. What the money was actually wired in. A €50,000 check is stored as €50,000. The company's currency. What the company reports in. It covers the company's marks, price per share, post-money valuation, metrics (ARR, cash, burn) and, for a pitch, the round terms. Usually this matches your checks, but it doesn't have to. You can invest in a euro-denominated company from a dollar account, for example. Your home currency. What your portfolio totals, cost basis, gains, IRR and multiples are in. It defaults to US dollars. When a figure isn't in your home currency, Signed shows it in its own currency first, with the home-currency amount after it in muted brackets: Hover over the bracketed figure, or tab to it with the keyboard, to see the rate behind it. For a check, that's the rate on the check's date ("€1 = $1.11 on May 14, 2024"). For a price or a valuation, it's today's rate. A figure that's already in your home currency shows once, with no brackets. Entering money in another currency The main money field on each form has a currency chip on its right side. That's the amount on a transaction, the value on a mark, the post-money on a SAFE conversion, and committed capital on a new fund. Click the chip to pick a currency. Your home currency and the company's currency are listed first, followed by the rest. The form's other money fields switch their symbol to match. The quicker way is to type the currency. Currency Magic™ reads symbols and codes on either side of the number, in upper or lower case: You type You get €50k €50,000.00, in euros 50k chf CHF 50,000.00, in Swiss francs CHF 1.5M CHF 1,500,000.00 CA$500k CA$500,000.00, in Canadian dollars £2.5k + 500 £3,000.00, in pounds 1500000 jpy ¥1,500,000, in yen (no decimals) A plain $ or ¥ stays in the form's current currency if that currency already uses the sign. So $5k on a Canadian-dollar check stays Canadian. If you leave the chip on the company's currency, the check follows the company. Pick something else, and the check keeps that currency even if the company's currency changes later. A company's currency The first check sets it. If a company has nothing priced yet (no checks, marks, metrics or round terms) and no currency of its own, your first check gives the company that check's currency. Put €25,000 into a new company and it's a euro company from then on. After that, checks keep their own currency. A dollar check into a company that's already in euros stays a dollar check. Signed converts it into the company's currency where it needs to, for example when working out a price per share. Changing a company's currency relabels; it doesn't convert. Suppose the company was set to dollars by mistake and the €2.50 share price was entered as $2.50. Switching it to euros fixes the label and leaves the 2.50 alone. Every figure already on the company keeps its number and is read in the new currency. Signed then recalculates the home-currency amounts at each check's own date. Because this changes what your figures mean, Signed asks you to confirm when the company already has figures on it. If what you actually want is a conversion, say the company redomiciled and now reports in pounds, enter the new figures in pounds from that point on. Earlier checks and marks will still be in their original currency. Your home currency and number format Both live in Settings → Currency. This is the currency your portfolio adds up in: total value, invested, gains, IRR, multiples, tax estimates, reporting and the dashboard. When you change it, Signed converts every check again at the rate from the day it went in, not at today's rate. Your history comes out the way it would look if you'd had this home currency from the start. The dashboard and the settings page show "Re-expressing your portfolio…" until this is done, then refresh themselves. There is one case where Signed refuses the change: when a check falls on a date the European Central Bank has no rate for. That means anything before January 4, 1999 (when the ECB began publishing), a few currencies before 2000 (BRL, CNY, ILS and INR), and the Icelandic króna between 2008 and 2018. In that case, Signed tells you which company and date are the problem rather than leaving your figures half-converted. You can also choose how numbers are written: Format Example 1,234.56 US, UK and most of Asia 1.234,56 Germany, Italy, Spain, Brazil and others 1 234,56 France, Canada (French), Scandinavia and others 1'234.56 Switzerland The format applies everywhere Signed writes a number: money, percentages (39,9%), multiples (4,70x), share counts and your emails. It also applies to what you type. In the 1.234,56 format, 25.000 means twenty-five thousand. Pasting a US-style 1,500,000 still works in every format. How conversion works A check converts into your home currency once, at the rate on its date, and that figure is saved with it. Your cost basis, proceeds from a sale and distributions are all fixed this way. A strong week for the euro doesn't change what your 2022 investment cost you. This is also the usual way to report foreign-currency investments for tax: each purchase and each sale at the rate on its own date. Your accountant has the final word on that. What a position is worth converts at today's rate: shares × price per share, or a fund's NAV. As a result, returns in your home currency combine two things: how the company did, and how its currency did against yours. A mark or metric can have a currency of its own, separate from the company's. Signed converts it into the company's currency at the rate on its own date before comparing it with earlier figures. That way a markup reads as a markup, not as a change in exchange rate. Money Signed reads for you Not every figure in Signed gets typed in. These are all currency-aware too: • AngelList imports. Each row is recorded in the currency its Invested column names, or US dollars if it doesn't name one. See Exporting your AngelList investment portfolio for how to get the file. • CSV imports. Signed reads the currency from a symbol or code in the money columns, from a currency column, or from a currency the whole sheet uses. The review step shows a Currency column when it finds one, so you can check it before importing. • Forwarded email. When you forward an investor update or a pitch, figures like €5M ARR are read in the currency they're written in. If the company already has another currency, the figure is converted into it at that day's rate. • Pitch decks and deal documents. Round size, valuation and financials are read in the deck's currency. Pitches that come in through your pitch page get the same treatment. • MCP. Signed's MCP server accepts a currency on new transactions, pitches and company updates. It also reports your home currency, so your assistant knows what your totals are in. If a company already has figures, changing its currency over MCP needs an explicit relabel, just like the confirmation in the app. • Company chat. The assistant on each company page is told the currency of every figure, and is asked not to convert them. Exports Your Signed CSV export (Settings → Your data) has four columns at the end of each transaction row: • Currency: the currency of the check. • Amount (Home): the amount in your home currency, at the rate on its date. • Home Currency: your home currency. • FX Rate: the rate used. The tax events export has a Currency column after Gain/Loss. A US-dollar account gets the same columns, filled with USD and a rate of 1. Supported currencies Signed supports all 30 currencies in the ECB's reference set: AUD (Australian dollar), BRL (Brazilian real), CAD (Canadian dollar), CHF (Swiss franc), CNY (Chinese yuan), CZK (Czech koruna), DKK (Danish krone), EUR (Euro), GBP (British pound), HKD (Hong Kong dollar), HUF (Hungarian forint), IDR (Indonesian rupiah), ILS (Israeli shekel), INR (Indian rupee), ISK (Icelandic króna), JPY (Japanese yen), KRW (South Korean won), MXN (Mexican peso), MYR (Malaysian ringgit), NOK (Norwegian krone), NZD (New Zealand dollar), PHP (Philippine peso), PLN (Polish złoty), RON (Romanian leu), SEK (Swedish krona), SGD (Singapore dollar), THB (Thai baht), TRY (Turkish lira), USD (US dollar), and ZAR (South African rand). Yen, won and krónur have no decimal places, so Signed doesn't add .00 to them. Currencies outside the ECB set, such as the UAE dirham, Nigerian naira and Argentine peso, aren't supported yet. If you invest in one of them, let us know. It helps us decide which to add next. What stays in US dollars A few things are in dollars because the rules define them that way: • QSBS limits. The Section 1202 exclusion cap ($10 million, or $15 million for stock issued after July 4, 2025) is written in dollars in US tax law, so Signed shows it in dollars. If you're not a US taxpayer, read QSBS for Non-US Investors first. • Our free QSBS calculator, for the same reason. • Billing. Plans are priced in US dollars. Common questions My check shows a different home amount than my bank statement. Signed uses the ECB reference rate for the day. Your bank charged its own rate, probably plus a spread. If you want the exact figure, you can enter the check in your home currency for the amount that actually left your account. Note that it will then be a home-currency check rather than a foreign-currency one. Why didn't my cost basis change when the exchange rate moved? Cost basis is fixed at the rate on the day you invested. Only current value moves with today's rate. See "How conversion works" above. I changed a company's currency and now the numbers look wrong. Changing a company's currency relabels its figures without converting them. If you meant to convert, switch the company back and enter new figures in the new currency instead. Why does the multiple on the timeline differ from the Holdings page? The timeline's figures are in your home currency, so they include currency movements. The Holdings page shows each lot in its own currency. Both are correct; they're answering different questions. Can I see my whole portfolio in another currency without changing my home currency? Not yet. Your home currency is the one lens on the totals. Changing it is safe, though: Signed converts every check again at its original date's rate, and you can switch back at any time. Is my IRR in my home currency? Yes. Signed works out IRR and MOIC from your home-currency cash flows: checks at the rate on the day they went in, and today's value at today's rate. #### Monitoring Your AngelList Portfolio https://signed.com/learn/articles/monitoring-your-angellist-portfolio If you invest through AngelList, you know the drill: you make your investments, maybe get an occasional email from an SPV runner, and… that's about it. Want to track updates, see which positions have appreciated or declined, or just get a sense of how your portfolio's evolving? AngelList doesn't surface any of that. It’s a bit like sending your money off to a distant cousin and hoping for a holiday card. The Challenge: Sparse Updates AngelList is great at connecting you to early-stage deals. But once your investment is made, portfolio monitoring takes a back seat. AngelList doesn’t provide markups, markdowns, or any clear timeline of changes in your investments. Unless a founder or fund manager proactively shares an update, you’re left in the dark about how your portfolio is performing over time. This is where Signed’s AngelList importer steps in. Signed lets you export your AngelList investment data and upload it to your Signed account. Your exported data gets analyzed, compares it to any previous versions you’ve imported, and highlights what’s changed. Here’s what you get: • Explicit Markups & Markdowns: See, in plain language, which of your positions have gone up or down — and by how much. • Change Tracking: Get a clear timeline of updates, so you can spot new investments, exits, or changes in valuation as they happen. • Portfolio Insights: View all your alternative assets — not just AngelList — in one place for a holistic picture of your investments. The other nice thing about Signed? It actually has a list of angel investors. "AngelList" doesn't really... have a list... of angels anywhere. Odd. #### Receive Startup Pitches from Founders https://signed.com/learn/articles/pitch-submission Signed gives you a public link you can hand out to founders so they can send you their pitch directly. Share it on Twitter, drop it in your email signature, give it to a friend at a fund — anyone who visits the link can submit a deck and a short pitch, and it'll land in your pipeline automatically. No more digging through your inbox for that PDF someone forwarded you three weeks ago. Want to see one in the wild? Here's Tifo's pitch page — that's one example of what a founder sees when they land on your link. How it works When a founder visits your pitch link, they see a simple, branded page with your name and logo and a short form: their contact info, the company name, a one-line tagline, a short description, and a place to drop a deck. When they hit submit, the pitch shows up in Signed under the Triage stage of your pipeline, and we'll send you a quick email letting you know. If they upload a PDF deck, Signed reads through it for you and pulls out highlights, insights, and a few suggested tags before you even open it. By the time you click in, you've already got a head start on the read. Enabling pitch submissions Your pitch link is tied to an entity, so you can have different links for different vehicles — your personal angel checks, a fund, an SPV, whatever. To turn it on, head to your entities and either pick an existing one or create a new one. Then: 1. Give it a slug if it doesn't have one — that's the bit where you can customize or brand the URL. 2. Flip Accepting pitches on. 3. Add a logo, public name, and short description if you'd like. This is what founders see, so a little polish goes a long way. That's it. Your link is live at signed.com/pitch/your-slug. Finding your link You don't need to memorize the URL. Head to Pitches and look at the left sidebar — there's a "Receive pitches at" section that lists every entity that's currently accepting pitches, with the link right there to copy. If you've got multiple entities turned on, each one has its own link, so you can tell at a glance which channel a deal came from. Working through pitches New submissions land in Triage. From there, you can move pitches through the rest of the pipeline as you talk to founders: • Triage — fresh in, haven't looked yet • Tracking — interesting, keeping an eye on it • Meeting — had a chat, taking it seriously • Diligence — going deep • Passed — not this one Click into any pitch to see the deck, the highlights Signed pulled out, the founder's contact info, your notes, and anywhere else you've been chatting with them. Saying yes When you're ready to invest, hit Invest in Company at the top of the pitch page. You'll pick what kind of investment it is — equity, fund LP, or SPV — and Signed handles the rest: it spins up an investment record, carries over all the files, notes, and tags, and moves the company out of your pipeline and into your portfolio. Nothing gets lost in the shuffle. Other ways pitches come in The public link isn't the only way pitches show up. If a founder emails you (or someone forwards you a deck), you can forward any email to inbox@signed.com and it'll drop it into Triage just like a form submission. Same deal — if there's a PDF attached, you'll get the highlights and insights waiting for you. If something gets misfiled — say, an investor update comes in but lands as a pitch — there's a Correct to Investor Update button on the pitch page that'll reclassify it. Taking a break If you want to stop receiving pitches for a while, just flip Accepting pitches off on the entity. The link goes dark, and you can turn it back on whenever — your slug stays the same, so any link you've shared before will still work when you're ready again. #### Using Signed’s MCP Server https://signed.com/learn/articles/using-signed-s-mcp-server Signed’s MCP server (mcp.signed.com) makes it easy to bring your alternative investment data into large language models like ChatGPT and Claude. Here’s how to connect, what to expect, and how to troubleshoot common issues. What is the MCP Server? The MCP server is a secure API endpoint that exposes your Signed portfolio and investment data in a machine-friendly format. You can connect third-party tools, or even your AI assistants, for streamlined access to your financial information—without having to copy/paste a thing. Adding MCP to ChatGPT • Open ChatGPT (Plus or Team required for browsing and plugins). • Choose "Browse with Bing" or "Advanced Data Analysis" (for file uploads) modes. • Paste your MCP endpoint — https://mcp.signed.com — directly into the chat and prompt ChatGPT to fetch or summarize your portfolio. • For custom workflows, use the "Plugins" or "Actions" feature and add the MCP endpoint as a data source. For detailed setup, check OpenAI’s plugin documentation. Adding MCP to Claude • Open Claude (Anthropic’s web app, or via integrated partner platforms). • Prompt Claude with your MCP endpoint: "Please retrieve my portfolio from https://mcp.signed.com". • If you need API keys or authentication, follow instructions from your Signed account dashboard. Some Claude integrations may require you to add the MCP endpoint as a "tool" or "custom source"—see your provider’s documentation for specifics. Common Questions & Troubleshooting • Does MCP require authentication? Authentication is primarily handled over OAuth, but you may also generate a long-lived Personal Access Token in your Connections page for clients that don't place nicely with OAuth. • The AI says "I can’t access this server." Some LLM tools block external URLs for safety. You may need to use built-in plugin or data upload features, or check if your LLM provider allows custom APIs. • Is my data safe? Yup! All MCP tools are behind the same authentication that is used for Signed itself. For additional protection, you might want to add Passkeys to your account. If you’re stuck, contact Signed support or check our help articles for more data integration tips. #### What is Signed's Currency Magic™? https://signed.com/learn/articles/currency-magic Every money field in Signed has a little label in the corner that says Currency Magic™, and it exists so you never have to count zeros again: Here's everything it can do. Shorthand that expands itself Type a number the way you'd say it out loud, and Signed expands it the moment you leave the field: • k for thousands — 35k becomes $35,000 • m for millions — 2.5m becomes $2,500,000 • b for billions — 1b becomes $1,000,000,000 Capitalization doesn't matter (5M and 5m are the same), decimals work (7.5k → $7,500), and you can even mix in commas (1,500k → $1,500,000) if that's how your brain works. It does the math for you A money field is also a tiny calculator. Type a simple expression and Signed evaluates it when you tab away: • Addition — 5500 + 7300 becomes $12,800. Handy when one investment arrived as two wires. • Subtraction — 100k - 12500 becomes $87,500. • Multiplication — 50k * 3 becomes $150,000. Or multiply price per share by your share count and skip the spreadsheet entirely. You can chain operations and mix shorthand freely — 35k + 5k works, and so does 2 * 1.5m + 250k. Multiplication happens first, then addition and subtraction, just like you learned in school. (We considered calling the feature "arithmetic," but it didn't test as well.) When you save, Signed strips the display commas behind the scenes so the exact value is recorded — the formatting is for your eyes, not the database. Where you'll find it Anywhere Signed asks you for a dollar amount: investment amounts, post-money valuations, valuation caps, price per share, SAFE conversions, marks, committed capital, and company metrics like ARR, cash, and monthly burn. If there's a $ in the field, the magic is there — hover the Currency Magic™ label for a quick reminder of the syntax. So the next time you're logging a $2,500,000 round, just type 2.5m and move on with your day. #### What Happens If You Downgrade or Your Card Fails https://signed.com/learn/articles/downgrade-or-failed-payment Billing hiccups happen. A card expires, an annual renewal shows up at a bad moment, or you just decide you'd rather not pay for a plan this quarter. Here's exactly what happens to your account when it does — and the short version is that nothing you've put into Signed goes away. Your data stays put Downgrading to Free, canceling, or letting a payment fail does not delete anything. Your investments, transactions, marks, entities, pitches, contacts, notes, and every file you've uploaded all stay exactly where they are. We don't archive them, we don't wipe them after 30 days, and we don't hold them hostage. If you resume billing next week or next year, you'll log in and find your portfolio precisely as you left it. There's no re-import, no restore step, no "contact us to reactivate." The only thing that actually removes your data is deleting your account, which lives at the bottom of your data settings and requires your password to confirm. That one's permanent, and it's the only one that is. If your card expires or a charge fails When a payment doesn't go through, Stripe retries it over the following days and emails you about it. You keep full access to your plan during that retry window — we'd rather not lock you out of your own portfolio over an expired expiration date. To fix it, head to Billing and click Manage Subscription. That opens the Stripe billing portal where you can update your card and settle the outstanding invoice. Once it clears, nothing else changes; your billing date and plan stay the same. If the retries eventually run out and Stripe cancels the subscription, your account moves to the Free plan. See below for what that looks like. If you cancel or downgrade on purpose Cancel through Manage Subscription and you keep full access until the end of the period you've already paid for. The billing page will tell you the exact date. When that date passes, the account drops to Free. Switching between paid plans works differently and is instant — moving from Angel to Investor unlocks the new features right away with a prorated charge, and moving down does the same in reverse. What the Free plan looks like Free covers portfolio tracking, performance and analytics, tax basics, search, following other investors, document storage, and CSV export. It's capped at 5 positions. Two things worth knowing about that cap: • It only limits adding. If you had 40 positions on a paid plan and drop to Free, all 40 remain in your account and remain visible. You just can't add a 41st until you upgrade. • The same goes for entities. Extra LLCs or trusts you've set up keep working; you just can't create new ones on a plan that doesn't include multi-entity tracking. What you do lose is access to the paid feature areas until you resume. On Free, that's pitch triage and the deal pipeline, investor updates, email forwarding, CRM editing, and AI deal analysis. Dropping from Investor to Angel additionally parks the tax dashboards, QSBS clock, pro rata tracking, pitch reporting, and white-labeled emails. In every case, the feature is what's gated — not the data behind it. Your pitches, your K-1s, your QSBS holding periods, and your contacts are all still in the database, waiting. Upgrade and the pages light back up with everything already in them. Take an export whenever you want You don't have to take our word for any of this. Any plan, including Free, can generate a full export from Settings → Your Data. You'll get a zip containing a CSV of your positions, transactions, and marks, plus every file you've uploaded — decks, side letters, SAFEs, K-1s, all of it. Larger portfolios take a few minutes to build, and we'll email you when the download is ready. One note: we clear out generated export archives after seven days to avoid sitting on copies of your data indefinitely. If your link has expired, just generate a fresh one. There's no limit on how often you can do this. Resuming Go to Billing, pick a plan, and you're back. No reactivation fee, no waiting period, no "we deleted your account after 90 days of inactivity" surprise. If something about your billing looks wrong — a charge you don't recognize, a plan that didn't switch, a card that won't update — email us and we'll sort it out. ### Investing Basics #### Choosing a Bank for Angel Investing https://signed.com/learn/articles/choosing-a-bank-for-angel-investing Look: you're probably going to want a separate bank account for your angel investments. If you’re making angel investments, your bank account isn’t just a place to stash cash. It’s the launchpad for every wire transfer, the home for incoming returns, and—crucially—the first thing a startup or fund will see when you wire money their way. It also gives you the possibility of separation of concerns, where you won't tie your personal expenses or income in with your startup investments... which can be super helpful in case your account gets suspended because of larger check transfers you might do semi-regularly. Those tend to be red flags for most humans, but they happen frequently for angels! Personal vs. Entity Accounts One of the biggest rookie mistakes is wiring money from an account that doesn’t match the name on your signed investment documents. If you invest as “Jane Q. Angel LLC” but wire funds from your personal account, you may end up with delays, refund requests, or issues with your ownership record. Which: take our word for it... is pretty embarassing when you're dealing with a new founder you're trying to impress. Always open a bank account in the exact name of your investing entity—whether that’s your personal name, an LLC, a trust, or something else. This small detail helps make compliance and tax filings smooth, and it reassures recipients they’re dealing with the right party. If you’re investing as yourself, your personal checking account can work (but again, ideally you use a separate account). If you’ve set up an LLC, S-corp, or trust for your investments (see: tax and liability reasons), you’ll want to open a dedicated business account for that entity. Some banks require articles of incorporation or operating agreements to open accounts—gather these ahead of time to streamline the process. Banking Options for Angels Most traditional banks (think Chase, Wells Fargo, Bank of America) can open business accounts for your entity. But many angel investors are moving to online banks for their speed, UI, and lower fees- in particular, traditional banks tend to frown on a lot of larger-check wire transfers. Mercury is a favorite for tech-savvy angels and startups alike. It offers a modern interface, easy business account setup (even for LLCs), and quick domestic and international wires. Opening an account is typically fast—sometimes in a day or two—and you can manage everything online. Another great tool in the toolkit: Wise. Originally known for low-cost international transfers, Wise now offers multi-currency accounts and business banking features. If you invest across borders, Wise makes it simple to hold balances in USD, EUR, GBP, and more, then wire funds to startups worldwide without eye-watering conversion fees. Even if you're not multi-currency, Wise gets used a lot just because its UI is not a complete headache. Other digital-first options include Rho (which targets businesses and investors with cash management features), Brex (aimed at startups but open to investors), and Relay (geared towards small businesses and professional service entities). If you’re investing through a trust or other structure, check if your preferred bank can support that specific entity type—some fintechs are still catching up. Practical Tips for Transfers and Wires Double-check wire instructions, verify recipient account names, and always confirm routing numbers—typos can lead to lost funds or awkward emails with founders. For larger wires, some banks set daily or transaction limits; plan ahead if you’ll be moving more than $50,000 at once, and ask your bank to raise limits in advance if needed. Wise in particular is nice for handling this; much like Signed, they let you upload wire instructions and parse the account numbers out for you. One less step. Keep digital copies of every wire confirmation. Not only does this help if there’s ever a dispute about payment, but it also makes tax time easier. Many founders or fund managers will ask for your wire confirmation to match up incoming transfers. Build the habit of saving PDFs or screenshots in a dedicated folder (Google Drive, Dropbox, etc.) or on Signed itself. If you’re investing alongside others in a roll-up vehicle or syndicate, confirm whether you need to send funds to a third-party account. Some platforms or lead investors require entity-matched wires for compliance. The fewer surprises, the smoother your investment experience. Banking Hygiene and Record Keeping Separate your angel investing activity from your day-to-day spending. This makes accounting, taxes, and compliance dramatically simpler. Use your dedicated investment account for all deal activity—wires out, returns in, tax payments, and so on. If you invest through multiple entities, keep separate accounts for each. Reconcile your statements monthly. It’s easy to forget about a small dividend, a returned wire, or a surprise fee. Regular reviews help you catch mistakes and maintain a clean paper trail—critical if you ever get audited, or just want to remember what that $8,000 wire in February was for. Pop the details into your Signed account to track all your proceeds, cash, and payments. #### How to Find Angel Investors https://signed.com/learn/articles/how-to-find-angel-investors Finding the right angel investor can feel a little like matchmaking: you’re not just looking for a check, but for someone who gets your vision, fits your stage, and maybe even brings more than money to the table. While there's no one-size-fits-all approach, there are some effective ways to get started—and some creative tactics you might not have considered. Start with Your Network—And Beyond Begin by looking close to home. Reach out to founders who've raised money before, mentors, or advisors. These people often know angels or have been through the process themselves. Even if they aren’t writing checks, they can make warm introductions or help you refine your pitch. Remember: the startup world is surprisingly small, and a few thoughtful messages can open unexpected doors. Don’t stop with the “usual suspects.” Think about people in your extended professional or personal circles who are experts in your industry. Someone who’s led product at an established company, scaled a similar business, or even just worked in a tangential field could be interested in getting involved—sometimes as a first-time angel investor. These folk may not have a formal track record, but they can bring experience and connections that busy angels might not be able to provide. Plus, they might be more willing to roll up their sleeves and help than those busiest professional angels. Signed's directories Hey, we've got our own stuff, too. Signed has an angel investor directory where you can browse the investors on Signed and filter by a specific startup area. Find an AI investor that fits just right for you, or someone who tackles bio investment really well, things like that. And then you can submit your pitch straight from Signed without having to do the shady "how can I find an email address and stalk these people" approaches. Get Involved Locally Local startup events, pitch nights, or accelerator demo days are great for meeting both experienced angels and up-and-coming investors. Even if your city isn’t a startup hub, there are often regional groups or university programs where you can connect in person. Don’t overlook local business leaders or alumni from your school who have an interest in supporting emerging founders. Most of these people, even if they're wildly successful, have had people who have helped and believed in them early in their careers, too; give 'em a shot. #### How to Start Angel Investing https://signed.com/learn/articles/how-to-start-angel-investing Angel investing can be a fascinating way to put your capital to work, support founders, and maybe even land a front-row seat to the next big thing. But if you’re new to the world of early-stage investing, it can seem daunting. Here’s a practical guide to help you take the leap, understand the basics, and avoid common pitfalls. What Is Angel Investing? Angel investors use their own money to invest in early-stage startups, usually in exchange for equity or convertible securities. Unlike venture capitalists, angels invest as individuals (or sometimes as part of a group), and typically get involved before a company is well established. The risks are high, but the rewards—financial or otherwise—can be significant. Who Can Become an Angel Investor? First, the legal stuff: in the U.S., most startup investments are available only to accredited investors. This generally means you’ll need at least $200,000 in annual income ($300,000 if married) or a net worth over $1 million (excluding your primary residence). Some platforms have different requirements, but it’s best to check before you dive in. How to Find Deals You can’t invest if you don’t have opportunities. Many new angels start by: • Joining angel networks (local or online) • Building relationships with founders and other investors • Exploring platforms like Signed, AngelList, Republic, or SeedInvest • Attending pitch events and startup demo days For a deeper dive, see How to Find Angel Investors—even if you’re looking to invest, you'll want to know how founders find you. Making Your First Investment When evaluating a startup, look at the team, market size, product, traction, and deal terms. Don’t be afraid to ask founders tough questions—after all, it’s your money. You’ll likely encounter structures like SAFEs, convertible notes, or priced rounds. If you’re not sure what these mean, read up on SAFEs and Roll-Up Vehicles. How Much Should You Invest? One of the biggest mistakes new angels make: putting too much into one company. Early-stage investing is risky and unpredictable. Most angels spread their investments across many deals—think 10, 20, or even more. Learn more in How Many Investments Should I Make?. Setting Up to Invest Before you wire your first funds, you’ll need: • A bank account suitable for investing (see Choosing a Bank for Angel Investing) • Legal and tax advice, if possible • Some way to keep track of your investments, paperwork, and updates Tracking Your Angel Portfolio Angel investing isn’t set-and-forget. You’ll receive updates, new investment opportunities (pro rata rights), and tax forms. Keeping your portfolio organized is crucial for decision-making and compliance. That’s where tools like Signed come in. With Signed, you can track all your investments, store documents, get reminders about action items, and keep everything in one place. You can even forward investment emails directly to Signed or import your AngelList portfolio. Sign up for free to get started. Tax Considerations Some early-stage investments come with tax benefits (like QSBS), but also tax headaches. It’s worth reading up on QSBS Benefits for Angel Investors and what to do if an investment goes south (Handling Startup Investment Losses). Staying Sharp Angel investing is a journey, not a one-and-done transaction. Keep learning, build your network, and don’t be afraid to ask dumb questions—everyone starts somewhere. And remember: if you ever feel overwhelmed, you can always take a break and let your portfolio do the worrying for you (it’s good at that). Ready to Dive In? Becoming an angel investor is as much about staying curious as it is about writing checks. With the right mindset, tools, and a bit of luck, you’ll find your footing. Good luck—and welcome to the world of angel investing. #### Understanding Pro Rata Rights https://signed.com/learn/articles/understanding-pro-rata-rights When you make your first angel investment, the term "pro rata rights" might pop up in conversations or documents. It sounds technical, but it’s actually a simple—and important—concept to grasp if you want to keep your seat at the table as startups grow. What Are Pro Rata Rights? Pro rata rights give you, as an investor, the option to maintain your percentage ownership in a company during future funding rounds. In other words, if you own 1% of a startup and the company raises more money later, pro rata rights let you invest enough in that round to keep your 1% stake—not more, not less. Why Do They Matter? Startups often raise money in stages. If things go well, the company’s value increases with each round. Pro rata rights are valuable because they let you invest again at each stage and avoid having your ownership diluted by new investors. In hot companies, these rights can be gold: later rounds might be oversubscribed, and only investors with pro rata rights might have a shot at getting in. How Do You Get Pro Rata Rights? They’re typically negotiated up front, when you first invest. Some investment documents (like SAFEs—see our article What is a SAFE?) may or may not grant them by default. Always check the fine print, and don’t be shy about asking founders or your fellow investors how pro rata rights work for your deal. Using Your Rights (or Not) Pro rata rights are an option, not an obligation. You can choose to invest more money in future rounds, or you can pass—but you won’t get another chance if you skip it. Some investors use them to double down on winners; others save their cash for new opportunities. There’s no right answer, but knowing your rights gives you flexibility. #### What Are Roll-Up Vehicles? https://signed.com/learn/articles/what-are-roll-up-vehicles If you’re just getting into angel investing, you might have heard the term “roll-up vehicle” (or RUV) thrown around. These are a relatively new way for individual investors—especially those writing smaller checks—to participate in startup deals that might otherwise be out of reach. Let’s break down how roll-up vehicles work, how they came to be, and what they mean for you as an angel. The Origin of Roll-Up Vehicles Roll-up vehicles as a concept started gaining traction thanks to AngelList, which introduced them as a way to streamline startup fundraising. Before RUVs, if a founder wanted to accept lots of small checks from a crowd of angel investors, it was a paperwork nightmare. Each investor became a new entry on the company’s cap table, complicating everything from future fundraising to compliance. How Roll-Up Vehicles Work A roll-up vehicle pools multiple individual investors into a single legal entity—often an LLC. This entity, rather than each investor, is what appears on the company’s cap table. Behind the scenes, you and all the other angels in the RUV own a proportional share of that LLC. The result? The startup deals with just one shareholder, and you get to invest in deals that might otherwise require a much larger minimum check. Why They Matter for Angels Traditionally, startups set minimum investment amounts—sometimes $25,000, $50,000, or more—just to keep the cap table manageable. For many newer or smaller-check angels, that’s a non-starter. RUVs let you participate with much smaller checks, sometimes as low as $1,000 or $2,500. This democratizes access to deals and lets you diversify across more companies. What’s in It for Founders? Founders love RUVs because they simplify company ownership. Instead of wrangling 30 individual angels (and their lawyers), they see one line on the cap table. This can make future fundraising easier, reduce legal complexity, and keep things tidy for everyone involved. Fees and Considerations Of course, there are costs. RUVs typically charge a setup fee and ongoing administrative fees. These vary depending on the platform and the deal size. It’s worth reading the fine print so you understand how fees affect your returns. Also, liquidity is limited—exiting your share in a RUV before the startup sells or IPOs can be tricky. Decision-Making and Rights As an investor in a RUV, you usually don’t get direct voting rights or communication with founders. The lead investor—or whoever is managing the vehicle—acts on behalf of all backers. Read the terms carefully to know what rights you have (or don’t have). If you’re interested in learning more about the rights investors sometimes get, this guide to pro rata rights can help. Comparing RUVs to Traditional Syndicates RUVs are similar to syndicates, but with a focus on efficiency and cost—especially for founders. Syndicates often include a lead investor who negotiates deal terms and may charge a carry (a percentage of profits). RUVs are designed for smaller, simpler deals and sometimes have lower minimums and less active management. Is a Roll-Up Vehicle Right for You? If you’re looking to build a broad portfolio with smaller checks, RUVs can be a great tool. They let you participate in deals you’d otherwise miss and keep things simple for your founders. Just be sure to weigh the fees, your lack of direct rights, and the long-term illiquidity that comes with startup investing. Roll-up vehicles are a sign of angel investing becoming more accessible. If you’re ready to take the plunge, explore your options on platforms like AngelList, and always do your homework before wiring any money. After all, in startup investing, the only thing you want rolling up is your returns—not your sleeves for unnecessary paperwork. #### What is a SAFE? https://signed.com/learn/articles/what-is-a-safe If you’re exploring startup investing, you’ll quickly run into the term SAFE. No, it’s not just about keeping your money safe: SAFE stands for Simple Agreement for Future Equity. It’s a popular tool for early-stage startup fundraising, and it’s designed to make investing (and raising money) faster and simpler. The Origin of SAFEs SAFEs were introduced by Y Combinator in late 2013. Their goal? Replace convertible notes with something less complicated, less risky for founders, and easier for investors to understand. Since then, SAFEs have become a go-to fundraising instrument for startups, especially in the pre-seed and seed stages. How a SAFE Works When you invest in a startup via a SAFE, you’re not buying stock immediately. Instead, you’re signing an agreement that says your investment will convert into shares later—typically when the company raises a priced equity round. Until then, you don’t own equity, but you do have a legal right to get it in the future. Key terms in most SAFEs include: • Valuation Cap: The maximum company valuation at which your investment will convert into equity. If the next round is at a higher valuation, you still convert at the cap (giving you more shares). • Discount Rate: Some SAFEs offer a discount (often 10–20%) on the price per share in the next round, rewarding you for investing early. • No Interest, No Maturity Date: Unlike convertible notes, SAFEs don’t accrue interest or expire by a certain date. How Startups Issue SAFEs Startups use SAFEs to raise money quickly, often before they have enough traction to set a formal company valuation. Founders and investors sign the SAFE, funds are transferred, and the startup can focus on growth. There’s no need for lengthy negotiations or complex paperwork—just a straightforward agreement. How SAFEs Convert Your SAFE converts into equity (shares) when a specific event happens—usually the next equity financing round or sometimes an acquisition. The number of shares you receive is determined by the agreed valuation cap or discount (whichever gets you the best deal). After conversion, you become a shareholder just like investors in the new funding round. Things to Watch For SAFEs are streamlined, but there are details to consider: • They’re not debt, so you can’t get your money back if the company doesn’t raise another round. • You don’t have shareholder rights until conversion. • Terms can vary, so always read the SAFE agreement closely. #### What is a Valuation? https://signed.com/learn/articles/what-is-a-valuation If you spend any time around startups, you’ll hear people talk about "valuation" a lot — and for good reason. A company’s valuation is basically its estimated worth at a given moment. For founders, investors, and anyone holding equity, it’s a number that shapes the whole investment conversation. What Does a Valuation Represent? In simple terms, a valuation is what investors and founders agree the company is worth right now. It’s not always tied to revenue or profits (especially in early-stage startups), but it reflects the potential value of the business based on things like market opportunity, team strength, intellectual property, and traction so far. Why Valuation Matters in Fundraising Valuation comes up every time a company raises money. It sets the price for new investors to buy in and determines how much of the company they get for their investment. For example, if a startup raises $2 million at a $10 million valuation, the new investors collectively own 20% of the company post-raise. Valuation is especially important with instruments like SAFEs (Simple Agreements for Future Equity). SAFEs often include a valuation cap, which sets the maximum company value at which your investment will convert into shares. The lower the cap, the better for you as an investor — you get more ownership for your money if the company takes off. What Goes Into a Valuation? There’s no single formula for startup valuation, but here are a few ingredients that usually go into the mix: • Traction: Revenue, user growth, or any evidence the business is working. • Market size: The bigger the opportunity, the higher the potential value. • Team: Founders’ experience and track record can drive up the number. • Comparable companies: What similar startups have raised at, or what they’ve sold for. • Competitive landscape: How crowded or unique the space is. Ultimately, valuation is as much art as science — it reflects negotiation, investor sentiment, and sometimes just plain hype. Pre-Money vs. Post-Money Valuation There are two flavors of valuation that matter during a fundraise: pre-money and post-money. Pre-money valuation is how much the company is worth before the new investment comes in. Post-money valuation is the company’s value after the investment is added. The math is simple: • Post-money valuation = Pre-money valuation + New investment For example, if a startup has a pre-money valuation of $8 million and raises $2 million, the post-money valuation is $10 million. Most modern investment documents (and platforms like Signed) use post-money, because it makes it easier to calculate your ownership stake after the round closes. ### Taxes & Compliance #### Handling Startup Investment Losses https://signed.com/learn/articles/handling-startup-investment-losses Investing in startups comes with high hopes—and sometimes, hard losses. If your investment in a startup turns into a total loss, you might wonder what happens next on your tax return. The good news: the IRS doesn’t just leave you out in the cold. There are ways to use those losses to reduce your tax bill. Capital Losses and How They Work If you sell or abandon your stake in a failed startup, you’ll likely have a capital loss. Most startup investments are considered capital assets, so when you lose money, you can use that loss to offset any capital gains you have elsewhere—say, from stocks or real estate. If your capital losses exceed your gains, you can deduct up to $3,000 per year ($1,500 if married filing separately) from your ordinary income. If your loss is more than that, you can carry it forward to future years until it’s used up. Ordinary Losses: A Special Case Some startup investments—like those in Section 1244 stock—might qualify as an ordinary loss if the company goes out of business. This is a big deal: ordinary losses can be deducted against your ordinary income (like salary or business income), not just capital gains. For individuals, you can deduct up to $50,000 per year ($100,000 if married filing jointly) as an ordinary loss under Section 1244. But not every startup issues 1244 stock, so check your paperwork or consult a tax advisor. Documenting Your Loss To claim a loss, you need to show the investment is truly worthless. Usually, this means the company has been liquidated, or you’ve sold your shares for nothing. Keep records of your investment, communications on the company’s shutdown, and any liquidation paperwork. For more details, see IRS Publication 550. Filling Out Your Tax Return • Capital losses: Report on Schedule D of your Form 1040. • Section 1244 ordinary losses: Also use Schedule D, but note the ordinary loss portion on Form 4797. ### QSBS #### QSBS Benefits for Angel Investors https://signed.com/learn/articles/qsbs-benefits-for-angel-investors QSBS: A Quick Overview Qualified Small Business Stock (QSBS) is a tax benefit that can make angel investing even more attractive. Under Section 1202 of the Internal Revenue Code, if you invest in the right kind of startup and hold long enough, you may be able to exclude up to 100% of your gains from federal taxes when you sell your shares. That’s not a typo. The potential tax savings can be enormous, and they’re designed to reward investors willing to take risks on early-stage companies. Two Schedules, Split by July 4, 2025 The One Big Beautiful Bill Act rewrote Section 1202 on July 4, 2025, and the date you acquired your stock decides which set of rules you live under. This is the single most important thing to understand about QSBS today, because a portfolio can hold two positions in the same company running on two different schedules. Stock acquired after July 4, 2025 earns a tiered exclusion: • 3 years: 50% of the gain excluded • 4 years: 75% excluded • 5 years: 100% excluded The cap is the greater of $15 million or 10x your basis, and the company-side gross-assets ceiling rose to $75 million. Stock acquired on or before July 4, 2025 keeps the older all-or-nothing rule: nothing at all until you pass five years, then 100%, capped at the greater of $10 million or 10x basis, against a $50 million gross-assets ceiling. Note that the tiers are cliffs, not an accrual. A lot on the new schedule is worth 0% at two years and eleven months and 50% a month later. There is no partial credit for partial time. What Still Has to Be True The tiers only matter if the stock qualifies in the first place, and those rules didn’t loosen: • The stock must be issued by a U.S. C corporation (not an LLC or S corp). • The company’s gross assets must be under the ceiling at the time of issuance — $75M for stock issued after July 4, 2025, $50M before. • You must acquire the shares directly from the company, not from another investor. • The company must be an active business (not an investment holding company, for example). One subtlety worth internalizing: the holding period starts the day after you acquire the stock, so the earliest qualifying sale is one day past the anniversary. That is exactly the kind of detail worth tracking rather than eyeballing. Federal vs. State Tax Treatment At the federal level the rules are relatively clear and generous. But it’s not all champagne and confetti: state tax treatment of QSBS varies. Many states follow the federal exclusion, but some — like California — do not recognize it. That means if you’re a California resident, you’ll still owe California state taxes on your gains even if you’re fully exempt federally. Other states, such as New Jersey and Pennsylvania, also do not conform. Always check your specific state’s tax code or consult a tax professional before celebrating those potential windfalls. SAFEs and QSBS: A Complication SAFEs (Simple Agreements for Future Equity) are a popular way for startups to raise early capital. But when it comes to QSBS, SAFEs add a wrinkle: because a SAFE is not stock, the QSBS holding period generally doesn’t begin until the SAFE converts into actual shares. That conversion date also decides which schedule you land on — a SAFE signed in 2024 that converts in 2026 is new stock on the tiered schedule, not old stock on the five-year one. Eligibility also depends on the company’s gross assets at the time the stock is issued, not when the SAFE was purchased, so a later conversion could jeopardize eligibility if the company has grown past the ceiling. Importantly, gross assets are not the same as valuation: a company can be valued well above $75M and still qualify if its actual assets remain below the limit, though large financings can push it over. If you’re investing via a SAFE and aiming for QSBS treatment, track conversion timing and company growth carefully — which Signed can help with, naturally — and consult your tax advisor. The company itself is a good resource too; they can often tell you plainly whether your shares qualify. Making the Most of QSBS QSBS can be a powerful incentive for angel investors, but it comes with fine print, and since 2025 that fine print depends on a date. Track your acquisition dates carefully, note the types of shares you receive, and keep an eye on both federal and state treatment. If you’re serious about angel investing, understanding QSBS could help you keep a great deal more of your gains — just make sure you’re working with a good tax advisor to navigate the details. This is general information, not tax advice. #### How Long Do You Have to Hold Stock for QSBS? https://signed.com/learn/articles/qsbs-holding-period Five years for the full exclusion. That part hasn’t changed. What changed in July 2025 is what a shorter hold is worth, and the answer now depends on the day you acquired the stock. Stock acquired after July 4, 2025 earns the Section 1202 exclusion in tiers: 50% of the gain is excluded once you’ve held for three years, 75% at four, and 100% at five. Stock acquired on or before July 4, 2025 stays on the older rule for its whole life: nothing until you’ve held more than five years, then 100%. If you’re not sure which side of the line your shares fall on, the acquisition date decides it, and the QSBS calculator will route a position to the right rulebook and show you each date it crosses into a better tier. When the clock starts The holding period runs from the day the stock was issued to you. For an angel writing a check into a priced round, that’s the closing date. For everyone else it’s later than they think: • A SAFE or convertible note isn’t stock, so the clock generally doesn’t start until it converts at the priced round. Measuring from the wire date is the most common way to come up years short. • Stock options start the clock on the day you exercise. Not the grant date, not the vesting date, and not your start date. • RSUs start it on the day they settle into shares, which at most companies is at or after an IPO. The anniversary is a cliff, not a ramp The tiers are steps, not an accrual. A lot on the new schedule is worth nothing at two years and eleven months and 50% a month later; there is no partial credit for the time in between. Under the old rule the drop is steeper: four years and eleven months is worth exactly as much as one day. The two schedules also count the anniversary itself differently. The new tiers read “held for at least” three, four, or five years, so a tier opens on the anniversary. The old rule reads “more than five years,” which is the day after the fifth anniversary. Selling pre-2025 stock on the anniversary itself leaves you one day short of the exclusion, and one day short is the same as never having qualified. If a sale is anywhere near a milestone, check the actual date before you sign. What a partial tier is worth Less than the percentage suggests. Gain that qualifies as QSBS but isn’t excluded is taxed at up to 28%, not the ordinary 20% long-term rate, so a 50% exclusion cuts the bill by about a third rather than half. Three years is a real benefit under the new rules, but it isn’t half of five. Ways the clock carries over A few transfers keep the holding period intact. Stock received by gift or inheritance takes the original holder’s acquisition date. Preferred stock converted into common keeps the date the preferred was issued. And if you have to sell before you qualify, a Section 1045 rollover lets you carry the holding period into newly issued QSBS, provided you’ve held more than six months and reinvest within 60 days. What never carries over is a purchase from another holder. Shares bought in a tender offer or on a secondary market aren’t QSBS at any holding period. Write the date down Every one of these rules turns on a date you won’t be able to reconstruct from memory years later: the closing, the conversion, the exercise. Record it when you invest, while the answer is still one email away. Signed keeps a clock on every QSBS-flagged position so the next milestone is never a surprise, but a spreadsheet with the right column does the job too. This is general information, not tax advice. #### QSBS Rules Before and After July 4, 2025 https://signed.com/learn/articles/qsbs-rules-before-and-after-july-4-2025 The One Big Beautiful Bill Act rewrote Section 1202 on July 4, 2025, and it did so without touching anything already issued. Stock acquired after that date runs on a new schedule. Stock acquired on or before it keeps the old one, in full, for as long as you hold it. Most angel portfolios built across 2025 now straddle both. Which rulebook you’re on is decided by the acquisition date and nothing else. The sale date is irrelevant: pre-2025 stock sold in 2035 is still on the old rules. The QSBS calculator routes a position from its acquisition date, which is the one input it can’t guess. What changed The holding period. Old rules: nothing until you’ve held more than five years, then 100% of the gain excluded. New rules: 50% at three years, 75% at four, 100% at five. More on how the holding period works, including why the anniversary counts differently under each. The per-issuer cap. The exclusion is limited, per company, to the greater of a dollar cap or ten times your basis in the stock. The dollar cap rose from $10 million to $15 million. The new $15 million figure is indexed for inflation beginning in 2027; the old $10 million cap isn’t. Married taxpayers filing separately get half of either. The gross-assets ceiling. The company’s aggregate gross assets have to be under a ceiling at the time your stock is issued. That ceiling rose from $50 million to $75 million, also indexed from 2027. Gross assets are the company’s balance sheet, not its valuation, so a company valued at $200 million can still be under the ceiling if it hasn’t raised or retained that much. The AMT preference. Under the old law a partial exclusion (the 50% and 75% rates that applied to stock issued before September 28, 2010) put a slice of the excluded gain back into the alternative minimum tax. The new tiers carry no AMT preference at all. What didn’t change Everything that decides whether stock is QSBS in the first place. It still has to be stock in a U.S. C corporation, acquired by you at original issuance for money, property, or services, in an active business rather than a holding company or a professional-services firm. Gain that qualifies but isn’t excluded is still taxed at up to 28% rather than 20%. And the states that ignore Section 1202 still ignore both versions of it. Two lots in one company A follow-on check almost certainly lands on a different schedule from the first one. Seed stock bought in 2024 and Series A stock bought in 2026 in the same company are two lots with two holding periods, two exclusion schedules, and two caps. Track them separately, and expect a sale of the whole position to produce two different tax answers. The date that matters for a lot is when the stock was issued, which isn’t always when you paid. A SAFE signed in 2024 that converts in 2026 is 2026 stock on the new tiers. An option granted in 2023 and exercised in 2026 is the same. The law also stops you from moving old stock onto the new schedule by swapping it: shares received in exchange for pre-2025 stock in a reorganization keep the old date. The edge case Stock acquired on July 4, 2025 is old-rules stock. The new schedule applies to stock acquired after the date of enactment, and the holiday itself is on the wrong side of that line. This is general information, not tax advice. #### Why QSBS Gain Is Taxed at 28%, Not 20% https://signed.com/learn/articles/qsbs-28-percent-rate Run a three-year sale through the QSBS calculator and the tax on the half that isn’t excluded comes out at 28% federal, not the 20% long-term capital gains rate you were expecting. That isn’t a bug in the calculator, and it isn’t a surcharge. It’s the reason a 50% exclusion doesn’t save you 50% of your tax bill. Long-term gain isn’t one rate Three years clears the one-year test for long-term treatment easily. But long-term capital gain isn’t taxed at a single rate. Section 1(h) of the tax code sorts it into bands, and one of those bands, capped at 28%, is reserved for two things: collectibles, and “Section 1202 gain,” meaning gain from qualified small business stock that the exclusion didn’t reach. The excluded portion leaves your income entirely. Whatever is left is in the 28% band. The 28% is a ceiling, not a flat rate. A seller whose ordinary bracket is lower pays that instead. But for anyone with a seven-figure exit in the year of sale, 28% is the number. On top of that sits the 3.8% net investment income tax, which applies to the non-excluded gain the same way it applies to any other investment income. Excluded gain isn’t in your gross income, so it escapes the NIIT too. Taken together, the taxable part of a partial-tier sale runs at about 31.8%. What a tier is actually worth Take a $1 million gain on stock acquired after July 4, 2025, sold by someone in the top bracket: • Not QSBS: the full gain at 20% plus 3.8% is about $238,000 in federal tax. • Three years, 50% excluded: $500,000 comes out. The other $500,000 at 28% plus 3.8% is about $159,000. That’s a third off the bill, not half. • Four years, 75% excluded: $250,000 taxed at 31.8% is about $79,500. Two thirds off. • Five years, 100% excluded: nothing, federally. The tiers are still worth reaching. Three years is a real discount, and it’s a discount that stock on the old rules doesn’t get at all. But when you’re deciding whether to wait another year for the next step, price the step at what it actually saves, not at the percentage on the label. The holding period article covers when each step opens. Why the band exists None of this is new. The 28% band has held Section 1202 gain since the 1990s, back when the exclusion was 50% for everyone. It just stopped mattering for a decade: stock issued after September 27, 2010 got a 100% exclusion, so for most angels there was never any non-excluded QSBS gain to tax. The 2025 rewrite brought partial exclusions back for everyone, and the 28% band came back with them. One piece of the old regime that didn’t come back is the alternative minimum tax. Partial exclusions on pre-2010 stock put 7% of the excluded gain back into the AMT calculation. The new tiers carry no AMT preference. The state layer All of the above is federal. A state that follows Section 1202 taxes the same non-excluded gain at its own rate, and a state that doesn’t follow it taxes the whole gain regardless of tier. In California, the state bill on a partial-tier sale is often larger than the federal one. This is general information, not tax advice. #### Which States Tax QSBS Gains? https://signed.com/learn/articles/which-states-tax-qsbs Section 1202 is a federal rule. Most states inherit it automatically, because their income tax starts from federal income and gain the exclusion removed never arrives. A handful of states start from their own definition of income instead, and in those states a fully excluded federal gain is still fully taxed. This is the most volatile corner of QSBS right now, and it’s where the largest number missing from most estimates lives. The QSBS calculator carries a conformity table for every state; this article is the reasoning behind it. States that tax the gain anyway As of late summer 2026, five states decline to follow Section 1202 at all. If you’re a resident of one of them when you sell, the entire gain is taxable at the state level, no matter how long you held or which federal tier you reached: • California, at a top rate of 13.3%. More below. • Pennsylvania, at a flat 3.07%. • Alabama, at up to 5%. • Mississippi, at up to 4%. • Oregon, at up to 9.9%. Oregon is the newest addition: SB 1507 decoupled the state from Section 1202 entirely, old rules and new, for sales on or after January 1, 2026. Hawaii is a partial case. It conforms only to the original 50% exclusion, so the state benefit stops at half the gain regardless of your federal tier. States in motion Conformity is decided by legislatures, and several have moved recently or are trying to: • New Jersey went the other direction and started following Section 1202 for sales on or after January 1, 2026. Sell before that date and the gain was fully taxable; sell after and it follows the federal exclusion. • District of Columbia decoupled by emergency act in December 2025. Congress disapproved that act in February 2026, which put DC back in conformity. Expect another attempt. • New York conforms today. A bill to decouple was introduced in January 2026 and withdrawn. New York City residents owe roughly another 3.9% of local tax on the non-excluded part. • Washington has no income tax but levies a capital gains excise tax of 7%, rising to 9.9% on gains over $1 million, above a standard deduction near $278,000. Because it starts from federal capital gain, excluded QSBS gain falls outside it, but the Department of Revenue’s position has been contested and bills to reach QSBS gain directly have already been filed. • Massachusetts conforms, but also has its own small business stock regime with a separate 3% rate that can apply instead. Worth checking locally before trusting either number. One more wrinkle for stock on the new tiers. Some states conform to the federal code as of a fixed date rather than automatically, and where that date predates July 2025 the state hasn’t formally adopted the tiered schedule yet. Iowa, Kentucky, Maine, North Carolina, Vermont, and West Virginia are in this position as of this writing. Treat the state figure on a partial-tier sale in those states as unsettled until the legislature catches up. Why California costs so much more California had its own version of the QSBS exclusion until a court struck it down in 2012 for favoring in-state companies. The legislature responded in 2013 by repealing the exclusion entirely rather than fixing it, and it has never come back. Every dollar the federal government exempts is fully taxable in California at ordinary income rates, which top out at 13.3%. On a $3 million gain, that’s roughly $399,000 the federal exclusion does nothing about. For a California angel with a fully qualified five-year hold, the state bill is frequently the entire tax bill, and it doesn’t shrink by waiting. The calculator shows this as its worked example for a reason. Which state is “your” state The state that taxes the gain is the one you’re a resident of when you sell, not the one the company is in. A California company sold by a Texas resident owes no California tax on the gain; a Texas company sold by a California resident owes the full 13.3%. Changing residency ahead of an exit is a real strategy and a heavily audited one, and it is very much a conversation for a CPA rather than an article. The states with no income tax on this gain at all are Alaska, Florida, Nevada, New Hampshire, South Dakota, Tennessee, Texas, and Wyoming. Everyone not named on this page follows the federal number. Rates change every session; the calculator lets you overwrite its rate for exactly that reason. This is general information, not tax advice. #### QSBS and SAFEs: When the Holding Period Starts https://signed.com/learn/articles/qsbs-and-safes Most angel checks today go in on a SAFE, and most angels measure their QSBS holding period from the day the money left. Those two facts don’t fit together. Section 1202 is a rule about stock, and a SAFE isn’t stock. It’s a contract to receive stock later, and the holding period generally doesn’t start until that later actually arrives. The clock starts at conversion A SAFE converts into shares when the company closes a priced round. That conversion is when you acquire stock, so it’s when the Section 1202 clock starts, when the company’s gross assets are tested, and when the acquisition date that decides which rulebook you’re on is set. A SAFE signed in 2024 that converts in 2026 is 2026 stock, on the new tiered schedule, with a holding period that starts in 2026. The 2024 wire date does nothing. Convertible notes work the same way, and for the same reason: debt isn’t stock either. Put the conversion date into the QSBS calculator, not the SAFE date, and the tier timeline it shows will be the real one. Signed treats an unconverted SAFE as a position that isn’t on a clock yet, and starts the clock the day you record the conversion. The gross-assets trap The company’s aggregate gross assets have to be under the ceiling ($75 million for stock issued after July 4, 2025; $50 million before) at the time the stock is issued. For a SAFE, that’s the priced round, and the priced round is precisely when a company is most likely to have just crossed the line. Gross assets are the balance sheet, not the valuation. A company can be valued at $300 million and still be under the ceiling if its cash and other assets are below it. But a large financing that lands before your SAFE converts, or the same round that converts it, can push assets over. If it does, the stock you receive was never QSBS, and no holding period fixes that. Note that the test is on the money the company has, so a $60 million round closing into a company with $20 million on hand converts your SAFE into stock that doesn’t qualify. This is one of the most common ways QSBS is lost without anyone noticing. SAFEs that never convert If the company is acquired before a priced round, a SAFE typically pays out in cash. You never held stock, so there was never QSBS to exclude. The gain on the SAFE is generally treated as capital gain, long-term if you held it more than a year, taxed at the ordinary long-term rate rather than the 28% Section 1202 band. That’s not the worst outcome. It just isn’t the exclusion. The argument that SAFEs are stock Some tax advisors take the position that a post-money SAFE is close enough to equity that the holding period should run from the SAFE’s purchase date. The IRS hasn’t said so, and there’s no ruling or case to lean on. The conservative planning assumption, and the one the calculator uses, is the conversion date. If your advisor takes the aggressive position, understand that it’s a position, and that the difference is usually a year or two of holding period on the largest tax break you’ll ever claim. What to write down The SAFE date, the conversion date, the gross assets at conversion if the company will tell you, and the share count you received. The company usually can say plainly whether your shares qualify, and the moment to ask is the round that converts you, not the exit five years later. This is general information, not tax advice. #### QSBS for Stock Options: When Your Clock Starts https://signed.com/learn/articles/qsbs-stock-options Section 1202 tests the stock, not your job title, and the statute never mentions employment. An employee who exercises options and holds the shares clears the same bar an angel does, on the same tiers, with their own per-issuer cap of $10 million or $15 million rather than a slice of one shared across the cap table. What catches employees isn’t eligibility. It’s the date the clock starts. The clock starts at exercise Not the grant date, not the vesting date, and not your start date. Option shares are issued to you when you pay for them, so the holding period runs from the day you exercise. Someone who joined at seed, vested over four years, and exercised the week the acquisition closed has held QSBS for days. The QSBS calculator takes the exercise date as the acquisition date for this reason. Early exercise with an 83(b) election starts the clock immediately, on shares that haven’t vested yet, which is most of the reason early exercise is worth doing at a company you believe in. Early exercise without an 83(b) election starts it at vesting instead, one tranche at a time. The exercise date also decides which rulebook you’re on. Options granted in 2023 and exercised in 2026 are 2026 stock on the new tiered schedule. Exercising too late can disqualify you entirely This one is quieter than the holding period. The company’s gross assets are tested when the stock is issued, which for options means the day you exercise, not the day you were granted them. Join when the company has $8 million on the books, exercise after it has crossed $75 million ($50 million for shares issued on or before July 4, 2025), and the stock may never have been QSBS at all. Holding it for five years afterward doesn’t fix that. It’s an argument for exercising early that has nothing to do with the strike price. Gross assets are the balance sheet, not the valuation, so ask the company where it stands rather than guessing from the last round’s headline number. Your cost basis Basis does double duty in Section 1202. It sets the gain, and it sets the ten-times-basis floor under the per-issuer cap, so an employee with a large basis can exclude more than the $15 million headline figure. Your basis is what you paid, plus any spread you’ve already paid ordinary income tax on. Exercise a non-qualified stock option and the spread is W-2 income that year, so your basis is the full fair market value on the exercise date. Exercise an incentive stock option and hold it through a qualifying disposition and your basis is just the strike; the spread is an alternative minimum tax item, not regular-tax basis. Sell ISO shares in a disqualifying disposition and the spread becomes ordinary income, and the basis rises to match. Note that the ISO holding periods (two years from grant, one from exercise) and the Section 1202 holding period are separate tests that happen to run concurrently. Meeting one says nothing about the other. Exercising at the exit A cashless or net exercise the week a deal closes produces shares you hold for hours. Those shares are genuinely QSBS, if the company qualified on the exercise date, and the exclusion is genuinely worth zero, because the holding period is zero. The same is true of shares you buy from a colleague in a tender offer, for a different reason: they weren’t issued to you by the company at all. If you’re holding RSUs rather than options, the picture is worse still; RSUs rarely qualify. This is general information, not tax advice. #### Do RSUs Qualify for QSBS? https://signed.com/learn/articles/do-rsus-qualify-for-qsbs In principle, yes. In practice, almost never. The reason is timing, and it’s the same timing that makes stock options tricky, pushed one step further. An RSU isn’t stock until it settles A restricted stock unit is a promise to deliver shares later. Until it settles, you don’t own stock, so nothing Section 1202 cares about has happened yet. Both the holding period and the gross-assets test land on the settlement date, when the shares are actually issued to you. At most private companies, RSUs are “double-trigger”: they vest over time but only settle on a liquidity event, an IPO or an acquisition. That structure exists for good reasons (it keeps employees from owing income tax on shares they can’t sell), but it means the shares arrive at the worst possible moment for QSBS. The company’s gross assets are long past the $75 million ceiling, so the shares don’t qualify on issuance. And even where they somehow did, the clock would start on the day of the liquidity event, five years before any exclusion applies. Your basis is the settlement price Even in the rare case where RSUs settle at a qualifying company, the shares arrive with a basis equal to their fair market value on settlement, because that value is taxed as ordinary income when you receive them. The only gain QSBS could ever exclude is appreciation after settlement. Everything the RSU earned between grant and settlement was already taxed as wages. When it can work RSUs qualify when a company small enough to be under the gross-assets ceiling settles them early, on a single vesting trigger rather than at a liquidity event. That’s uncommon, since a company that small usually issues options instead, and it’s exactly why QSBS is mostly an options question. Don’t confuse RSUs with restricted stock awards. An RSA is actual stock, issued to you at grant and subject to vesting, and with an 83(b) election the Section 1202 clock starts at grant, just as it does for early-exercised options. Founders’ stock is usually an RSA. If you hold one, you may well have QSBS; run the numbers with the grant date in the QSBS calculator. If you hold RSUs at a late-stage company Section 1202 isn’t your break, and no amount of holding will make it one. The planning that matters for you is ordinary capital gains planning: the one-year mark for long-term treatment on post-settlement appreciation, the timing of sales across tax years, and your state’s treatment of the gain. This is general information, not tax advice. #### Tender Offers, Secondary Shares, and QSBS https://signed.com/learn/articles/qsbs-tender-offers-and-secondary-shares Section 1202 requires original issuance. Your stock has to have come from the company itself, in exchange for money, property, or services. That single requirement decides most tender offer and secondary questions, and it decides them in opposite directions depending on which side of the trade you’re on. Buying in a tender: not QSBS If you buy a colleague’s shares in a tender offer, or an early employee’s shares on a secondary marketplace, or a founder’s shares directly, you’re a secondary purchaser. The shares may have been QSBS in the seller’s hands; the exclusion doesn’t travel with them. Your shares aren’t QSBS at any holding period, and five years of patience won’t change that. The same applies to an SPV or fund that buys secondary shares and passes the position through to you. A partnership can pass QSBS treatment to its partners, but only for stock the partnership acquired at original issuance while you were a partner. Ask before you wire. Selling into a tender: a sale like any other Selling your own shares into a tender offer is a disposition, and if your shares qualified and you’ve reached a tier, the exclusion applies exactly as it would on an acquisition. This is what the QSBS calculator prices. The date of the tender against your tier dates is the whole question; a tender that lands a month before a milestone is a good reason to sell only part of a position, or none of it. If you haven’t reached a tier and have to sell anyway, a Section 1045 rollover can carry the holding period into new QSBS, provided you’ve held more than six months and reinvest within 60 days. The redemption rules There’s a quieter problem when the company is the buyer. A tender offer where the company itself repurchases shares is a redemption, and Section 1202 has rules designed to stop companies from recycling old stock as new QSBS. Two windows matter: • Stock isn’t QSBS if, within two years before or after it was issued, the company redeemed stock from you or a related person, beyond a small de minimis amount. • Stock isn’t QSBS if, within one year before or after it was issued, the company made “significant” redemptions, generally more than 5% of the aggregate value of all its stock. So a company-funded buyback can void QSBS status for shares issued to other investors around the same time, including a round that closed a few months earlier. The regulations carve out redemptions on termination of employment, death, disability, and divorce, and the thresholds have some give. But if a company you hold is running a buyback near a financing, this is a question worth putting to a CPA before the exit rather than after. Investor-led tenders, where a third party buys and the company merely facilitates, aren’t redemptions. What counts as original issuance Stock you bought in a priced round. Stock a SAFE or convertible note converted into. Shares you received by exercising options or on the settlement of RSUs, since those are issued by the company as compensation. Stock received by gift or inheritance from someone who acquired it at original issuance, with their holding period intact. Stock received in certain reorganizations in exchange for QSBS. What’s never on the list is a purchase from another holder, however the trade was arranged. This is general information, not tax advice. #### QSBS for Non-US Investors https://signed.com/learn/articles/qsbs-non-us-taxpayers Section 1202 is an exclusion from US federal income tax. It can only help you if you owe US federal income tax on the gain in the first place, and if you’re not a US taxpayer, you usually don’t. For most non-US angels investing in American startups, QSBS is a rule that applies to their co-investors and not to them. The QSBS calculator has an option for exactly this case, and it mostly reports that there’s nothing to exclude. Non-resident aliens generally owe no US tax on the gain A non-resident alien, meaning someone who is neither a US citizen nor a US tax resident, generally isn’t subject to US tax on the gain from selling stock in a US company. Two exceptions: gain that’s effectively connected with a US trade or business you conduct, and the rule that taxes capital gains of a non-resident who was physically present in the US for 183 days or more in the year of sale. Outside those, there’s no US tax for Section 1202 to remove. That means your home country’s rules govern, along with any tax treaty it has with the US. Most treaties give the taxing right on share sales to the country of residence. The UK, Canada, Germany, Australia, and most other countries tax their residents on worldwide capital gains, and none of them recognizes Section 1202. Some have their own incentives with a family resemblance: the UK’s EIS and SEIS reliefs, or Canada’s lifetime exemption for “qualified small business corporation” shares, which despite the near-identical name is a different rule with different tests that a US startup won’t meet. US citizens and green card holders abroad You’re still a US taxpayer wherever you live, and Section 1202 applies to you normally. You’ll typically owe tax where you live as well, and whether that country gives you a credit for US tax on the gain (or the US gives you one for theirs) is a treaty question. Note that an exclusion produces no US tax to credit, so a fully excluded federal gain can still be fully taxed abroad, much as it is in California. If you become a US taxpayer while holding Nothing in Section 1202 requires you to have been a US taxpayer when the stock was issued. Whether the stock is QSBS depends on the company and the issuance: a US C corporation, under the gross-assets ceiling at issuance, shares acquired by you at original issuance. If those held when you invested, the holding period counts from the original acquisition date, not from the day you moved. Someone who invested from London in 2023 and became a California resident in 2026 may well hold QSBS, with a clock that’s already three years along. The company has to be American The rule that trips up non-US angels most often runs the other direction. Section 1202 requires a domestic C corporation. A Delaware C-corp founded by non-US founders qualifies; a UK Ltd, an Estonian OÜ, or a Singapore Pte. Ltd. does not, no matter where the investor lives. If you’re a US taxpayer investing internationally, none of those positions are QSBS. If a foreign startup later flips into a Delaware parent, the stock you receive in the flip may or may not qualify, and the answer depends on the details of the exchange. This is general information, not tax advice. #### Section 1045 Rollovers: The QSBS Escape Hatch https://signed.com/learn/articles/section-1045-rollovers The QSBS Escape Hatch Most Angels Don't Know About Every angel investor eventually learns about QSBS — the tax break that can wipe out federal taxes on millions of dollars in startup gains. Far fewer know about its companion provision, Section 1045. That's a shame, because Section 1045 solves the single most common way angels lose their QSBS benefit: the exit they didn't choose. Here's the uncomfortable truth about angel investing: you don't control when your companies sell. Founders and boards do. And startups have a habit of getting acquired at year two or three — right in the middle of your QSBS holding period, before you've earned the exclusion you were counting on. When that happens, most angels shrug, pay the capital gains tax, and move on. They don't have to. Section 1045 lets you roll the gain from an early exit into new startup investments, defer the tax entirely, and — this is the remarkable part — keep your original holding-period clock running. Used well, it can turn a "too early" exit into a fully tax-free one. Let's dig in. A Quick QSBS Refresher Qualified Small Business Stock (Section 1202 of the tax code) lets you exclude enormous amounts of startup gains from federal taxes — historically up to $10 million or 10x your basis, whichever is greater. We've covered the benefits and the common mistakes in separate articles, so here's just the part that matters for this one: the holding period. The 2025 tax law split QSBS into two regimes, depending on when your stock was issued: Stock issued on or before July 4, 2025 plays by the old rules. You must hold for five years to get any exclusion at all. It's a cliff: four years and eleven months gets you nothing. Stock issued after July 4, 2025 gets a friendlier, tiered schedule: a 50% exclusion after three years, 75% after four, and 100% after five. The exclusion cap also rose to $15 million (or 10x basis), and companies can now have up to $75 million in gross assets at issuance, up from $50 million. Either way, the clock is everything. And a clock only helps if the company survives — as your company, with you as a shareholder — long enough for it to run out. The Early Exit Problem Say you invested $50,000 in a startup in 2023. In 2026, three years in, the company gets acquired for cash and your stake is suddenly worth $550,000. Congratulations — and condolences. Your stock was issued before July 5, 2025, so the old all-or-nothing rule applies: you're two years short of the five-year mark, your QSBS exclusion evaporates, and that $500,000 gain is fully taxable. At federal long-term capital gains rates plus the net investment income tax, you could be writing a check for roughly $120,000. You didn't sell early. The company sold early. The tax code, it turns out, has sympathy for exactly this situation. What Section 1045 Actually Does Section 1045 says: if you sell QSBS you've held for more than six months, and within 60 days you reinvest the proceeds into new QSBS, you don't recognize the gain now. Instead, the gain gets deferred — rolled into your new shares — and your original holding period carries over to the replacement stock. Read that last part again, because it's the magic. This isn't just a tax deferral. Your new shares inherit the age of your old ones. In the example above, your replacement stock starts life with three years already on the clock. Hold it two more years, and the combined five-year holding period qualifies the entire rolled gain for the full Section 1202 exclusion — as if the early exit never happened. Three requirements, then, and each has teeth: You held the original stock more than six months. Notably lenient — you don't need years of tenure to use a rollover, just six months and a day. (If you invested via a SAFE, remember your holding period starts when the SAFE converts to actual stock, not when you wired the money.) You reinvest within 60 days of the sale. Not 60 days from when the wire lands, not 60 business days, and there are no extensions. The clock starts on the sale date. More on why this is the hard part below. The replacement stock is genuinely QSBS. Newly issued stock, bought directly from a U.S. C-corporation that passes the gross asset test and the active business requirement. Buying someone's shares secondhand doesn't count, and neither does most fund investing (the same limitations we covered in Costly QSBS Mistakes). The Math: Basis, Partial Rollovers, and What Actually Gets Deferred The mechanics are cleaner than most tax provisions, but two rules matter. You must reinvest the full proceeds to defer the full gain — not just the gain. Gain is recognized to the extent your sale proceeds exceed what you put into replacement stock. Take the example above: you received $550,000 in proceeds on a $500,000 gain. To defer everything, you need to reinvest $550,000 — the whole check, not just the profit. If you reinvest $400,000 and keep $150,000, you'll recognize $150,000 of gain now and defer the remaining $350,000. Partial rollovers are perfectly allowed; they're just proportionally less powerful. The deferred gain reduces your basis in the new stock. Roll $550,000 into a new startup while deferring $500,000 of gain, and your basis in the new shares is $50,000 — your original cost, effectively transplanted. That deferred gain hasn't vanished; it's embedded in the new shares, waiting. If the new company exits after your combined holding period crosses five years, Section 1202 can exclude it. If you sell early again... you can roll again. There's no limit on chaining rollovers, and some sophisticated investors have kept gains rolling across multiple companies for a decade. One more feature worth knowing: your 10x-of-basis exclusion cap is computed on QSBS math, and because the rolled shares carry your original (low) basis, the greater-of-$10M-or-10x cap usually means the flat dollar cap is what protects you. For most angel-sized checks, the cap is a distant concern — but if you're rolling seven-figure gains, talk to your tax advisor about how the caps stack across companies. The 60-Day Scramble Here's where theory meets reality. Sixty days is a brutally short window to find a startup worth backing, complete diligence, negotiate, and wire funds. Acquisitions also rarely surprise you on the day they close — but angels are often the last to know, and escrows and delayed payouts can complicate what counts as proceeds and when. A few practical habits make the difference between angels who can actually use Section 1045 and those who just read about it: Know your clocks before you need them. The moment an acquisition rumor surfaces, you should be able to answer: when did I acquire this stock (not the SAFE — the stock)? How long have I held it? Is it pre- or post-OBBBA stock? What's my basis? If your records live in a shoebox of PDFs and old emails, a 60-day sprint becomes a 60-day panic. This is precisely the kind of thing your portfolio tracker should surface at a glance. Keep live deal flow. Angels who see a steady stream of pitches can move inside 60 days; angels who invest opportunistically once a year usually can't. It's fine to accelerate an investment you were already considering — the replacement company doesn't need to be found after the sale, only funded after it. Get QSBS representations from the replacement company. Your rollover only works if the new stock actually qualifies — and stays qualified for substantially all of your remaining holding period. Ask the company to confirm its QSBS eligibility at investment, and ideally to refresh that confirmation annually. If the replacement company quietly blows its qualification two years in, your deferred gain can come rushing back. Loop in your CPA before the sale closes, not at tax time. The election is made on your return for the year of sale (extensions count), reported on Form 8949 with a statement attached. It's not hard, but it's not automatic — miss it and the deferral is gone. It's also revocable only with IRS consent, so you want the decision made deliberately. The Fine Print That Bites A few caveats belong in any honest discussion of Section 1045. States don't all play along. The rollover defers federal tax. California, most notably, doesn't conform to the federal QSBS rules at all — California residents owe state tax on the gain regardless. Several other states have partial or no conformity. Factor your state into the math before assuming a rollover makes you whole. SPVs and funds complicate things. If you invested through a syndicate or SPV structured as a partnership, rollover rights exist but run through partnership rules — the partnership can roll at the entity level, or you can sometimes opt out and roll your share individually by buying replacement stock in your own name and notifying the partnership in writing. It's workable, but it requires coordination and a cooperative fund manager. Ask before you assume. Stock deals are different. Section 1045 is built for sales — you receive cash, you reinvest cash. If your company is acquired in a stock-for-stock merger, different provisions may let your QSBS status carry into the acquirer's shares automatically. That's a topic for another article (and definitely for your tax advisor). Crossing the 2025 boundary raises open questions. If you roll pre-July-2025 stock into newly issued stock, which regime applies — the old five-year cliff or the new tiered schedule? The interaction of holding-period tacking with the OBBBA effective dates has genuine wrinkles that the IRS hasn't fully clarified. If you're doing a cross-regime rollover, get professional advice rather than assuming the friendlier answer. Why This Matters More Than Ever Under the old all-or-nothing QSBS regime, Section 1045 was a niche rescue tool. Under the new tiered rules, it's becoming a portfolio strategy. Post-2025 stock earns a 50% exclusion at year three and 75% at year four — which means an early exit might qualify for a partial exclusion, with Section 1045 available to roll the rest. Exclude what you can, defer what you can't, keep the clock running on the remainder. The two provisions were always designed to work together; the new rules just made the combination far more common in practice. The bigger lesson is one that runs through everything we write about QSBS: these benefits are won or lost on record-keeping and timing, usually years before you know which exit will make them matter. Every acquisition date, every SAFE conversion, every basis figure is a small detail — until a company sells at year three and those details are worth six figures. #### Costly QSBS Mistakes https://signed.com/learn/articles/costly-qsbs-mistakes Why QSBS Matters Qualified Small Business Stock (QSBS) can be a powerful tax break for angel investors. If you qualify, you could exclude $15 million or more of gains from federal taxes. But the rules are strict, and even a small misstep could cost you dearly. Here are the most common QSBS mistakes investors make, and how to avoid them. 1. Assuming Everything Runs on a Five-Year Clock The One Big Beautiful Bill Act rewrote Section 1202 on July 4, 2025. Stock acquired after that date earns 50% of the exclusion at three years, 75% at four, and 100% at five, capped at the greater of $15 million or 10x basis. Stock acquired on or before it keeps the old all-or-nothing five-year rule and a $10 million cap. The mistake is applying one mental model to a whole portfolio. Positions bought a year apart can sit on different schedules with different caps, and a follow-on check into a company you already own almost certainly does. Selling everything at the five-year mark is fine; assuming nothing is worth anything before then can cost you a 50% or 75% exclusion you already earned. 2. Selling One Day Too Early The holding period starts the day after you acquire the stock, so the earliest qualifying sale is one day past the anniversary, not on it. Tiers are cliffs: a lot is worth 0% at two years and eleven months and 50% a month later, with no credit for the time in between. If a sale is anywhere near a milestone, check the actual date before you sign. 3. SAFE Conversions After the Gross-Assets Ceiling If you invest through a SAFE, your QSBS holding period starts when it converts into actual stock. If that conversion happens after the company’s gross assets exceed the ceiling — $75 million for stock issued after July 4, 2025, $50 million before — your shares won’t qualify at all, even if your original check was tiny. Timing matters. Be mindful of company growth and conversion triggers. 4. Buying Secondary Shares QSBS benefits only apply to stock purchased directly from the company. If you buy shares on the secondary market (that is, from another investor), those shares won’t qualify. Always confirm the source of your shares before assuming you’ll get the tax break. 5. Investing via a Fund (Usually) Most venture funds are structured as partnerships or LLCs. Unless the fund is structured specifically to pass QSBS benefits through, you won’t be eligible — even if the portfolio company qualifies. If you’re investing through a fund or SPV, ask about QSBS treatment before signing anything. 6. Transferring Shares Incorrectly QSBS can sometimes survive transfers (like gifting to family), but the rules are intricate. Transfers to trusts, partnerships, or other entities can reset the holding period or disqualify the shares entirely. If you’re planning to transfer your QSBS, consult a tax advisor first. 7. Never Writing the Date Down Every mistake above is really the same mistake: the exclusion is decided by dates you can’t reconstruct from memory years later. Record the acquisition date, the conversion date, and where the shares came from at the time you invest, while the answer is still easy to get. This is general information, not tax advice — but the record-keeping is on you either way. ### Portfolio Management #### De-Risking After a Big Win https://signed.com/learn/articles/de-risking-after-a-big-win So you’ve backed a startup that’s taken off—maybe you’re up 10x or more on paper. Congratulations! But now you face a classic angel investing dilemma: do you cash out some of your gains, or hold tight for even more upside? Let’s break down how to think about this using a diversification mindset. Rebalancing: Not Just for Public Stocks Diversification isn’t a one-time thing. Even if you started with a balanced set of bets, a single big winner can leave your portfolio dangerously concentrated. If one investment grows to become, say, 40% or more of your total portfolio value, you’re now heavily exposed to the fate of that single company—no matter how promising it looks. When to Consider Selling Unlike public markets, selling startup shares isn’t always easy. But options like tender offers or secondary market sales do come up, usually after a company’s major growth rounds. Here’s a way to approach the decision: • Think in Multiples: If your investment is up 5x, 10x, or more, consider what that means for your overall returns. Would selling a portion at a 10x multiple materially improve your portfolio’s risk/reward balance? • Portfolio Proportion: If one winner is more than 25-40% of your total portfolio value, it might be time to de-risk—especially if the rest of your investments are early-stage and less liquid. • “Let it Ride”—But Not All of It: Many experienced angels sell a portion (say, 25-50%) when given the chance, letting the remaining shares ride. This way, you lock in some gains but keep skin in the game for future upside. Scenario Example Let’s say you’ve made 10 angel investments. Nine are valued at your original $10k each, but one is now worth $300k—a 30x on your $10k. Your total portfolio is $390k, and that one company represents over 75%. If a tender offer comes along, selling even a third of your position ($100k) would reduce your concentration, realize significant gains, and still leave you exposed to further upside if the company continues to grow. In the end, there’s no perfect answer. But if you’re sitting on a big winner, ask yourself: what’s my risk tolerance, and how would I feel if this one company stumbles? A little de-risking can go a long way toward keeping your angel investing journey (and your stress levels) on track. Want to dive deeper into portfolio strategy? Check out How Many Investments Should I Make? for more on portfolio construction and risk. #### How Many Investments Should I Make? https://signed.com/learn/articles/how-many-investments-should-i-make When you picture successful angel investing, you might imagine a savvy investor picking just a handful of winners and riding them to glory. In reality, the data tells a different story: broad diversification—making many, smaller bets—often leads to better overall returns. The Power of Many Bets AngelList has published several reports over the years showing that angel investors who make more investments (think 25, 50, or even 100+ deals) tend to see more consistent and higher returns than those who concentrate their capital in only a few startups. Their 2022 analysis shows that the odds of hitting a true outlier—the kind of startup that returns 10x or more—increase dramatically as you expand your portfolio. It’s a numbers game: more tickets, better chance of a jackpot. Startups are risky. Even the smartest investors can’t reliably predict which early-stage companies will break out. By spreading your investments across more companies, you increase your chance of catching a big winner while reducing the sting of inevitable failures. This approach is especially important in venture and angel investing, where power-law returns (a few big hits drive most of the gains) are the norm. How Many Investments Should You Make? There’s no magic number, but many experienced angels aim for at least 20-30 investments to start seeing the benefits of diversification. Some go much higher. The exact number depends on your capital, risk tolerance, and access to deals. Just keep in mind: don’t put all your eggs in one startup’s basket. Other Allocation Tips • Don’t chase every deal—focus on opportunities that fit your interests and thesis. • Consider smaller check sizes to stretch your capital across more startups. • Revisit your allocation periodically. You may want to double down on later-stage follow-ons or rebalance over time. • Stay mindful of your overall financial plan. Angel investing is risky and should only be a slice of your net worth. While investing in startups will always involve some luck, the evidence is clear: spreading your bets gives you the best shot at startup investing success. And if you hit the next unicorn, you can always tell your friends it was pure skill. ## Glossary Angel investing terms, defined. Index at https://signed.com/learn/glossary. ### Accredited Investor https://signed.com/learn/glossary/accredited-investor An accredited investor is a person or entity that meets income, net-worth, or professional-credential thresholds set by the SEC, qualifying them to invest in private securities that aren't registered with regulators. For individuals, the main tests are $200,000 in annual income ($300,000 jointly with a spouse) over the past two years, or $1 million in net worth excluding a primary residence. Most angel deals are open only to accredited investors. The thresholds are the practical gate to angel investing. You qualify if your income has been at least $200,000 (or $300,000 with your spouse) for the last two years with the expectation it continues, or if your net worth exceeds $1 million excluding the value of your home. Since 2020 you can also qualify by credential rather than money — holding an active Series 7, 65, or 82 license counts — which opened the door to finance professionals who are knowledgeable but not yet wealthy. The reason this matters is that nearly every SAFE, convertible note, and priced seed round relies on a securities exemption (most often Regulation D, Rule 506) that limits the deal to accredited investors. In practice you'll self-certify your status when you invest, and for some deals the company or syndicate may verify it with documents like tax returns or a letter from your accountant. Being accredited is the entry ticket; the next tier up, the qualified purchaser, unlocks access to larger private funds with looser investor-count limits. ### Angel Investing https://signed.com/learn/glossary/angel-investing Angel investing is the practice of providing financial backing to early-stage startups, typically in exchange for equity ownership. Unlike venture capital firms that invest institutional money, angel investors use their own personal funds. Most angel investments range from $5,000 to $100,000. In practice, most angels write checks into companies they hear about through their own network — a founder they used to work with, a deal a friend is already in, or a syndicate they follow. Deal flow is the whole game: the best investors see hundreds of opportunities a year and say no to nearly all of them. A typical angel might make 5 to 10 investments a year at $10K–$25K each, building a portfolio of 20 or 30 companies over time. Angel investing is a power-law business, not an average-returns business. Most of your companies will return nothing, a handful will return your money, and one or two — if you're lucky and patient — return enough to make the whole portfolio work. That's why diversification matters so much: a concentrated portfolio of three startups is closer to gambling than investing. In the US, you generally need to be an accredited investor (roughly $200K in annual income or $1M in net worth excluding your home) to participate in most deals. ### ARR https://signed.com/learn/glossary/arr Annual Recurring Revenue (ARR) is a metric used primarily by SaaS and subscription-based companies. It represents the annualized value of recurring revenue, giving investors a normalized view of a company's revenue run rate. ARR is one of the most important metrics for evaluating early-stage software companies. ARR is usually calculated from the most recent month's recurring revenue: a company doing $100K in subscription revenue in March is running at roughly $1.2M ARR. Investors lean on ARR because it strips out one-time noise — a big setup fee or a one-off consulting project shouldn't count, because it won't repeat next year. When a founder quotes ARR, it's worth asking what's actually recurring underneath the number. ARR matters most as a growth signal and a valuation anchor. A seed company growing from $500K to $2M ARR in a year is telling a very different story than one stuck at $500K, even if both are the same size today. Early-stage software is often valued as a multiple of ARR, so a company at $2M ARR valued at a 10x multiple implies a $20M valuation. Watch the growth rate and net revenue retention alongside the headline number — ARR that grows only because the company keeps spending more to acquire each new customer is far less valuable than ARR that compounds from existing customers expanding. ### Cap Table https://signed.com/learn/glossary/cap-table A capitalization table (cap table) is a spreadsheet or document that shows the equity ownership structure of a company. It lists all shareholders, their ownership percentages, and the types of securities they hold (common stock, preferred stock, options, warrants, SAFEs, etc.). Cap tables become increasingly complex as companies raise multiple rounds of funding. A simple early cap table might show two founders splitting common stock 50/50, a 15% option pool reserved for employees, and a handful of angels holding SAFEs that haven't converted yet. After a priced round, it grows to include preferred shares for the new investors, updated ownership percentages for everyone, and the fully diluted totals that account for unexercised options and outstanding SAFEs. For an angel, the cap table is where dilution becomes real. Say you buy 2% of a company at the seed stage. After a Series A and Series B, that 2% might be diluted to 1.2% — your share count never changed, but the company issued new shares to new investors. A clean, well-maintained cap table also surfaces warning signs: too much founder stock given away too early, a messy collection of convertible instruments at different caps, or a tiny option pool that will force more dilution at the next raise. When companies report new rounds, your ownership and effective price per share shift, which is exactly the kind of thing tools like Signed track automatically. ### Convertible Note https://signed.com/learn/glossary/convertible-note A convertible note is a short-term debt instrument that converts into equity, usually at a discount, when the company raises a subsequent financing round. Unlike SAFEs, convertible notes carry an interest rate and a maturity date. They were the standard instrument for early-stage investing before SAFEs became popular. Here's a concrete example. You invest $50,000 in a convertible note with a 20% discount, an 8% interest rate, and a $5M valuation cap. Two years later the company raises a priced round at a $10M pre-money valuation. Your note has accrued about $8,000 in interest, so you're converting roughly $58,000. Because the round price is above your cap, you convert at the $5M cap rather than the $10M round price — effectively buying your shares at half the price the new investors pay. The two features that don't exist in a SAFE are the ones to watch: interest and a maturity date. Interest increases the dollar amount that converts, and the maturity date is a hard deadline by which the note must either convert, be repaid, or be renegotiated. In the rare case a company never raises another round and the note matures, the investor is technically a creditor — though in practice early-stage startups rarely have the cash to repay, so notes usually get extended. Most seed deals have moved to SAFEs because they avoid this debt machinery, but you'll still see convertible notes, especially in bridge financings between rounds. ### Cost Basis https://signed.com/learn/glossary/cost-basis Cost basis is the original value of an investment for tax purposes, typically the purchase price plus any associated costs. When you sell or otherwise dispose of an investment, the difference between the proceeds and your cost basis determines your capital gain or loss for tax reporting. For a straightforward equity purchase, cost basis is simply what you paid: invest $25,000 for shares and your basis is $25,000. If that stake is later acquired for $100,000, your taxable gain is the $75,000 difference. Where it gets subtle is with SAFEs and convertible notes — your cost basis is the cash you put in, but the holding period and share details don't fully settle until the instrument converts to actual stock, which matters for both long-term capital gains and QSBS eligibility. Tracking cost basis accurately is one of the most underrated parts of angel investing, because it directly drives your tax bill years later when an exit finally happens. Keep records of the exact amount invested, the date, and the documents for every position — including follow-on checks into the same company, which each carry their own basis and holding period. When a portfolio spans dozens of companies and multiple instruments, reconstructing this from memory at exit time is painful, which is why it's worth recording as you go. ### Dilution https://signed.com/learn/glossary/dilution Dilution is the decrease in an existing shareholder's ownership percentage that happens when a company issues new shares, typically in a financing round. Your share count stays the same, but because the total number of shares grows, the slice of the company you own shrinks. Dilution is a normal and expected part of startup investing — the goal is for the company's rising value to more than offset the smaller percentage you hold. Picture buying 2% of a company at the seed stage. The company then raises a Series A and issues new preferred shares to the incoming investors. You didn't sell anything and your share count is unchanged, but the pie now has more slices, so your 2% might fall to 1.4%. Raise a Series B and it drops again. Each round you don't participate in chips away at the percentage, even as the price per share climbs. The thing to internalize is that dilution isn't inherently bad — owning 1% of a company worth $500M beats owning 2% of one worth $20M. What matters is whether each round raises the value of the company faster than it shrinks your stake. Two things make dilution worse than it needs to be: oversized option pool top-ups, which come out of existing holders before the new money arrives, and down rounds, where new shares are issued at a lower price than the last round. Angels with pro rata rights can defend their percentage by investing more in later rounds, but most simply accept dilution as the cost of the company growing. ### Discount https://signed.com/learn/glossary/discount A discount gives investors on a SAFE or convertible note the right to convert into equity at a reduced price relative to the next priced round — commonly 20%. It compensates early investors for writing checks before the company had a priced valuation. When an instrument carries both a discount and a valuation cap, the investor converts at whichever produces the better price. Here's the mechanics. You invest $25,000 on a SAFE with a 20% discount. When the company later raises a priced round at $1.00 per share, your SAFE converts at $0.80 — so your $25,000 buys 31,250 shares where a new investor's $25,000 buys 25,000. The discount is the early-bird price: you took the risk before there was a priced round, and the discount is how that risk gets paid for at conversion. Most SAFEs and notes carry both a discount and a valuation cap, and you convert at whichever gives the lower price — they don't stack. That means the discount does the work in modest rounds: if the round prices below the cap, the 20% off is what sets your price. If the company takes off and the round prices well above the cap, the cap sets your price and the discount is irrelevant. A discount alone, with no cap, is a weak deal in a breakout — 20% off a huge valuation is still a huge valuation — which is why caps became the standard companion. When you see a discount quoted on a deal, the two questions to ask are whether there's also a cap, and what the discount implies about how founders expect the next round to price. ### Distributions https://signed.com/learn/glossary/distributions Distributions are cash payments returned to investors from their investments. They can come from various events: a company being acquired, going public, paying dividends, or a fund liquidating its positions. Distributions are the ultimate measure of realized returns — paper gains don't count until cash is actually returned. A distribution event usually looks like an acquisition or IPO. Say you invested $20,000 and the company is acquired for a price that values your stake at $120,000 — once the deal closes and proceeds clear, that $120,000 lands as a distribution. Sometimes distributions come in pieces: an acquisition might pay out part of the proceeds upfront and hold the rest in escrow for a year, or an earnout might pay additional amounts if the acquired company hits targets. The reason experienced investors obsess over distributions is that everything else is just an estimate. A company can mark itself up on paper for years — your portfolio looks great in the dashboard — but until cash actually comes back, you haven't made a dollar. This is the gap between TVPI (which counts paper value) and DPI (which counts only cash returned). Early in a portfolio's life, distributions are usually zero while you wait through the long J-curve; the back half is where the realized returns finally show up. ### DPI https://signed.com/learn/glossary/dpi Distributed to Paid-In (DPI) measures how much cash has been returned to investors relative to the total amount invested. A DPI of 1.0x means you've gotten back exactly what you put in. A DPI of 0.0x means no cash has been returned yet (common in early-stage portfolios). DPI is sometimes called the 'realization ratio' because it only counts actual distributions, not paper gains. Suppose you've invested $200,000 across your portfolio and, over time, exits have returned $300,000 in cash. Your DPI is 1.5x — for every dollar you put in, a dollar fifty has come back, and it's real money in your account, not a markup. A DPI above 1.0x means you've recouped your entire investment and everything beyond it is profit; below 1.0x means you're still waiting to get whole. DPI is the metric that can't be gamed, which is why it's the truest scorecard late in a portfolio's life. The tradeoff is that it's brutally pessimistic early on — a three-year-old angel portfolio almost always shows a DPI near 0.0x, because companies haven't had time to exit yet. That's why investors pair it with TVPI: TVPI shows the full picture including paper gains, while DPI shows what's actually been realized. Watching the gap between them close over the years is watching paper value turn into cash. ### Gain/Loss https://signed.com/learn/glossary/gain-loss Gain or loss represents the difference between the proceeds from selling or disposing of an investment and its cost basis. Gains held for more than one year qualify as long-term capital gains with lower tax rates. Losses can be used to offset gains, reducing your overall tax liability. The holding period is what separates a good tax outcome from an expensive one. Sell within a year and the gain is short-term, taxed at ordinary income rates that can exceed 37%. Hold more than a year and it's long-term, taxed at the lower capital-gains rate (typically 15% or 20%). Since angel investments are illiquid for years anyway, most exits naturally land in long-term territory — and if the stock qualifies as QSBS, part or all of the gain may be excluded from federal tax depending on how long it was held. Losses aren't just dead weight. Capital losses offset capital gains dollar-for-dollar, so a $50,000 loss on one company directly reduces the taxable gain on a winner. Given that most angel investments fail, this matters: a worthless position can often be claimed as a loss, and in some cases startup losses qualify for additional treatment under Section 1244. The practical takeaway is to track every position's outcome, including the failures, because the losses do real work at tax time. ### IRR https://signed.com/learn/glossary/irr Internal Rate of Return (IRR) is the annualized return on your investment, accounting for the timing of cash flows. Unlike simple return multiples, IRR factors in when money was invested and when (or if) it was returned. A 3x return in 2 years has a much higher IRR than a 3x return in 10 years. IRR is the standard metric for comparing investment performance across different time horizons. The power of IRR is that it makes returns comparable across wildly different timelines. A 3x return sounds the same in both cases, but a 3x in 2 years is about a 73% IRR, while a 3x in 10 years is only about 12%. Time is doing the work: getting your money back faster lets you redeploy it, and IRR captures that. This is why the same MOIC can represent a phenomenal investment or a mediocre one depending on how long the capital was tied up. IRR has real quirks worth knowing. It's highly sensitive to timing, so a single early distribution can inflate it dramatically, and very young investments can show absurd IRRs (or none at all) because there's barely any time in the denominator. It also assumes you can reinvest returns at the same rate, which is rarely true. Because real portfolios have irregular cash flows — checks going out on different dates, distributions coming back unpredictably — the honest way to compute it is XIRR, which uses actual dates rather than assuming neat annual periods. Treat IRR as one lens among several, best read next to MOIC and DPI. ### MOIC https://signed.com/learn/glossary/moic Multiple on Invested Capital (MOIC) measures how many times your original investment has grown. A MOIC of 2.0x means your investment has doubled in value. Unlike IRR, MOIC doesn't account for time — a 2x return in one year looks the same as a 2x return in ten years. MOIC is useful for quickly understanding the magnitude of returns. MOIC answers a single blunt question: how big? Put in $30,000, and if the position is now worth $150,000, your MOIC is 5.0x. It's the number angels quote in conversation because it's intuitive and captures the magnitude of an outcome — a 50x company is a story; a 1.5x company is a rounding error. In a power-law portfolio, the whole job is finding the rare position with a double-digit MOIC. Its blind spot is time, which is exactly where IRR comes in. A 5x over 3 years and a 5x over 15 years have identical MOIC but completely different IRRs, and only one of them is a great use of capital. It's also worth distinguishing gross MOIC (before fees) from net MOIC (after any fund or syndicate fees and carry), since those can differ meaningfully when you invest through an SPV or fund. Read MOIC for magnitude, IRR for speed, and DPI for whether it's real yet. ### Monthly Burn https://signed.com/learn/glossary/monthly-burn Monthly burn (or burn rate) measures how much cash a company spends each month beyond its revenue. For startups that are not yet profitable, burn rate determines how long the company's cash reserves will last (its 'runway'). Investors track burn rate to understand when a company will need to raise additional funding. Runway is the number that actually keeps founders up at night, and it falls straight out of burn. A company with $1.2M in the bank burning $100K a month has 12 months of runway — and since raising a round takes months, it really needs to start fundraising around month 6. As an investor, when you read an update saying burn went from $80K to $150K, the real question is whether revenue and progress grew to match, or whether the company just got more expensive without getting more valuable. It helps to separate gross burn (total monthly spend) from net burn (spend minus revenue), because a company with real revenue can have high gross burn but modest net burn. Burn isn't bad on its own — spending to grow is the entire point of venture funding — but burn without corresponding traction is the classic path to a down round or a shutdown. The healthiest signal is burn that's deliberate: rising in step with hiring and growth, with a clear plan for the next raise well before the runway runs out. ### NIIT https://signed.com/learn/glossary/niit The Net Investment Income Tax (NIIT) is a 3.8% federal surtax on investment income — capital gains, dividends, interest, rents — owed by taxpayers whose modified adjusted gross income clears $200,000 single or $250,000 married filing jointly. It sits on top of the capital gains rate rather than replacing it, so the headline 20% long-term rate is really 23.8% for most people with an exit large enough to care. Gain excluded under Section 1202 never enters income at all, so QSBS escapes the NIIT along with the capital gains tax. The NIIT is the 3.8% almost nobody quotes when they talk about capital gains rates. It came in with the Affordable Care Act and applies to the lesser of your net investment income or the amount your modified adjusted gross income exceeds the threshold — $200,000 filing single, $250,000 married filing jointly, $125,000 married filing separately. Any exit big enough to be interesting blows past those numbers, so in practice an angel with a $2M long-term gain owes $400,000 at the 20% rate plus $76,000 of NIIT on top: $476,000, an effective 23.8%. Where it matters most for angels is the interaction with QSBS. Gain excluded under Section 1202 is excluded from gross income entirely, which means it isn't net investment income either — the exclusion takes the 3.8% off with it, and no separate election or form is needed. But gain that qualifies as QSBS and *isn't* excluded is a different story: it's Section 1202 gain taxed at a maximum 28% rate rather than 20%, and the NIIT still applies, for roughly 31.8% all in. That's the arithmetic behind the partial tiers on post-2025 stock. A 50% exclusion at three years doesn't halve the bill, because the half that stays taxable is taxed at a worse rate than an ordinary long-term gain would have been. Two details are worth carrying around. The thresholds are not indexed to inflation, so more investors drift over them every year, and they're based on MAGI — meaning a large gain can push you across the line by itself even if your salary sits well below it. The NIIT is also purely federal; states run their own rates and have nothing analogous, so it never interacts with your state bill. This is general information, not tax advice. ### Post-money Valuation https://signed.com/learn/glossary/post-money Post-money valuation is the total value of a company immediately after a round of financing. It equals the pre-money valuation plus the amount of new capital raised. For example, if a company has a $8M pre-money valuation and raises $2M, its post-money valuation is $10M. Post-money valuation determines how much of the company new investors own. The reason post-money matters more than pre-money for an investor is that it sets your ownership directly. If the post-money is $10M and you put in $100,000, you own exactly 1% — your check divided by the post-money valuation. That simple relationship is why post-money is the number to anchor on: it tells you what slice of the company your money buys, before any future dilution. The arithmetic is straightforward but the negotiation is everything. Pre-money plus new investment equals post-money, so on the same $2M raise, an $8M pre-money (20% sold) is a very different deal for founders than a $4M pre-money (33% sold). Post-money SAFEs, now the YC standard, are popular precisely because they pin down the investor's ownership percentage at signing rather than leaving it to be recalculated when the round prices. Just remember that the 1% you buy today gets diluted as the company raises more rounds — your ownership at exit is what ultimately drives your return. ### PPS https://signed.com/learn/glossary/pps Price per share (PPS) is the price of a single share of a company's stock. In venture investing, PPS is determined during each funding round and is used to calculate valuations and ownership percentages. Your effective PPS may differ from the round PPS if you invested via a SAFE or convertible note with a discount. Price per share is set at each priced round by dividing the valuation by the total share count, and it's the unit that makes ownership concrete: if the PPS is $2.00 and you invest $50,000, you own 25,000 shares. Every subsequent round establishes a new PPS, and comparing it to the price you paid is the cleanest way to see whether your position has marked up or down — a later round at $6.00 against your $2.00 entry is a 3x paper gain on price alone. Your effective price per share can be lower than the round price when you came in through a SAFE or convertible note. A 20% discount means you convert as if you paid 80% of the round's PPS, and a valuation cap can push your effective price lower still. That gap is the reward for taking early risk: when your SAFE finally converts, you may end up holding more shares per dollar than the investors who priced the round. Effective PPS, not the headline round price, is what determines how many shares you actually own. ### Pre-money Valuation https://signed.com/learn/glossary/pre-money Pre-money valuation is what a company is worth immediately before it takes in new money in a financing round. Add the new capital raised and you get the post-money valuation. Pre-money is the figure founders and investors negotiate, because it determines how much of the company the new investment buys and how much existing shareholders are diluted. The relationship is simple arithmetic: pre-money plus the new investment equals post-money. If a company negotiates an $8M pre-money and raises $2M, the post-money is $10M, and the new investors own 20% ($2M of $10M). That same $2M raise at a $4M pre-money would cost the founders a third of the company — which is why the pre-money number is the heart of the negotiation. A higher pre-money means less dilution for existing holders and a smaller stake for the new money. For an angel, it helps to remember that pre-money is the founders' starting ask, while post-money is what actually pins down your ownership. The two move together, but they answer different questions: pre-money is "what do we agree the company is worth today?" and post-money is "what slice does my check buy?" When you come in on a SAFE or convertible note, you usually don't set a pre-money at all — a valuation cap stands in for it until the priced round converts your instrument and a real pre-money gets negotiated. ### Pro Rata https://signed.com/learn/glossary/pro-rata Pro rata rights give an investor the option — but not the obligation — to put more money into a company's future rounds in order to maintain their existing ownership percentage. Without exercising pro rata, an early investor's stake gets diluted with each new round. Pro rata is one of the most valuable rights an angel can negotiate, because it lets you keep backing your winners. Say you own 2% of a company and it raises a new round that would otherwise dilute you to 1.4%. Your pro rata right lets you buy enough of the new round to hold your 2% — you write a follow-on check sized to your existing stake. You're never required to; it's an option you exercise when you still believe in the company. The point is that it puts the decision in your hands rather than letting dilution decide for you. Pro rata matters enormously in a power-law portfolio, because your returns are driven by a handful of winners and pro rata is how you put more money into exactly those companies at a still-reasonable price. The catch is capital: in a hot round, exercising pro rata across several breakout companies at once can take more cash than you have, which is why many angels can't fully use the rights they hold. Some leads pool members' pro rata into a follow-on SPV so smaller investors can still participate. When you pass on pro rata, your percentage simply dilutes — a normal outcome, but one worth choosing on purpose rather than by accident. ### QSBS https://signed.com/learn/glossary/qsbs Qualified Small Business Stock (QSBS) is a powerful tax benefit under Section 1202 of the Internal Revenue Code. Stock acquired after July 4, 2025 in a qualified small business (a domestic C corporation with gross assets under $75M) earns a tiered exclusion — 50% of the gain at three years, 75% at four, and 100% at five — capped at the greater of $15 million or 10x your basis. Stock acquired on or before that date keeps the older rules: nothing until five years, then 100%, capped at $10 million against a $50M asset ceiling. The numbers here are large enough to change your whole return. If you invest in a qualifying C corporation and later exit, you may exclude millions in capital gains from federal tax entirely. On a winning angel investment that's the difference between keeping nearly all of a multi-million-dollar gain and handing over 20%-plus to the IRS. It's frequently the single most valuable tax provision available to early-stage investors. What trips people up now is that there are two versions of the rule running side by side, and the acquisition date decides which one you're on. The One Big Beautiful Bill Act rewrote Section 1202 for stock acquired after July 4, 2025: those shares get a staircase instead of a cliff — 50% of the gain excluded at three years, 75% at four, 100% at five — with the per-issuer cap raised from $10 million to $15 million and the company's gross assets ceiling raised from $50 million to $75 million. Anything you already held on July 4, 2025 stays on the old all-or-nothing five-year rule for the rest of its life, and you can't move an old position onto the new rules by exchanging it, so most angel portfolios built across 2025 now straddle both regimes. One caveat on the partial tiers: gain that qualifies but isn't excluded is taxed at 28%, not the usual 20% long-term rate, so a 50% exclusion cuts your bill by roughly a third rather than half. The eligibility rules are strict either way. The company must be a domestic C corporation (not an LLC or S corp), under the asset ceiling at the time your stock was issued, and in a qualifying line of business. SAFEs and convertible notes are not stock yet, so the clock typically starts when they convert — a detail that catches a lot of investors off guard. The $15 million cap and the $75 million asset test are indexed to inflation starting in 2027; the old $10 million cap is not. Because the stakes are high and the rules unforgiving, QSBS is worth confirming with a tax advisor, and worth tracking acquisition dates carefully across every position so you don't accidentally sell at four years and eleven months. Note also that this is all federal: California doesn't conform to Section 1202 at all. This is general information, not tax advice. ### Qualified Purchaser https://signed.com/learn/glossary/qualified-purchaser A qualified purchaser is a status above accredited investor, defined under the Investment Company Act. For individuals, the main test is owning at least $5 million in investments. Qualified purchaser status lets funds admit them under the 3(c)(7) exemption, which can accommodate far more investors than the funds limited to accredited investors under 3(c)(1). Qualified purchaser is the rung above accredited investor, and the bar is much higher: roughly $5 million in investments for an individual (or $25 million for an entity investing on others' behalf). Note that the test is investments, not net worth, so your home and the value of a business you operate don't count toward it. There's also an intermediate tier worth knowing — the "qualified client" (about $2.2 million in net worth, or $1.1 million managed with the adviser) — which is the threshold that lets a fund manager charge performance fees or carry. The distinction matters because of fund structure, not individual deals. A fund relying on the 3(c)(1) exemption can take up to 100 investors (or 250 for smaller qualifying venture funds) and only needs them to be accredited. A fund using 3(c)(7) faces no statutory cap on investor count — though a separate rule effectively limits it to around 2,000 holders — but every single investor must be a qualified purchaser. Larger and more selective venture funds often choose 3(c)(7) for that headroom, which is why the bigger or more established the fund, the more likely you'll need qualified purchaser status to get in. For most individual angels writing checks into SAFEs and syndicate SPVs, accredited status is all you'll ever need; qualified purchaser comes up mainly once you start investing in sizable funds. ### Runway https://signed.com/learn/glossary/runway Runway is the number of months a company can keep operating before it runs out of cash, calculated as cash on hand divided by monthly burn. A company with $1.2M in the bank burning $100K a month has 12 months of runway. Because raising a round takes months, runway is the number that decides when a founder has to start fundraising — and the one an investor should watch most closely between updates. The arithmetic is simple — cash divided by monthly burn — but the number is only as fresh as the update it came from. A founder who reported twelve months of runway in March has, by September, about six left if nothing changed. That gap is why Signed tracks *implied* runway: the months reported, less the months that have passed since, so the figure on a company's page keeps draining between updates instead of freezing at whatever the last email said. When it reaches zero, one of three things happened — the company raised, cut burn, or is in trouble — and all three are worth a note to the founder. Runway also tells you when the next round is coming. Most founders start raising with six to nine months left, because a seed or Series A takes three to six months to close and nobody wants to negotiate from a position of weakness. So a company showing eight months of runway is a company about to ask you for a pro rata check, and one showing three is a company that either has a term sheet you haven't heard about or a bridge round on the way. Read runway alongside [monthly burn](/learn/glossary/monthly-burn) and [ARR](/learn/glossary/arr): burn rising while runway shrinks is fine if revenue is growing to meet it, and alarming if it isn't. ### SAFE https://signed.com/learn/glossary/safe A SAFE (Simple Agreement for Future Equity) is an investment instrument created by Y Combinator that has become the standard for seed-stage deals. Unlike convertible notes, a SAFE is not debt — it has no interest rate or maturity date. It simply converts to equity at the next priced round, subject to a valuation cap and/or discount. SAFEs are simpler and more founder-friendly than convertible notes. Here's how a SAFE plays out. You invest $25,000 on a post-money SAFE with a $5M cap. When the company raises its priced round, your SAFE converts to shares as if the company were worth $5M — so your $25,000 buys 0.5% of the company, locked in regardless of how high the actual round prices. If the round comes in below your cap, a discount (commonly 20%) usually applies instead, so you still come in cheaper than the new money. The instrument is short, standardized, and converts automatically — there's no debt, no interest, and no maturity date to manage. The most important distinction today is pre-money versus post-money SAFEs. YC's original 2013 SAFE was pre-money; its 2018 revision is post-money, and post-money is now the default. The difference is who absorbs dilution from other SAFEs: with a post-money SAFE, your ownership percentage is fixed at signing and isn't diluted by other SAFEs in the same round, which makes your stake far more predictable. The flip side is that stacking many post-money SAFEs can dilute founders more than they expect. Either way, SAFEs sit on the cap table as outstanding instruments until that first priced round converts them all into actual shares. ### Section 1045 https://signed.com/learn/glossary/section-1045 Section 1045 of the Internal Revenue Code lets an investor who sells Qualified Small Business Stock held for more than six months defer the capital gain by rolling the proceeds into newly issued QSBS within 60 days. The original holding period carries over to the replacement stock, so an early exit can still work toward the five-year requirement for the Section 1202 exclusion. Section 1045 is the escape hatch for QSBS exits that come too early. Say your company is acquired three years after you invested — well short of the five-year hold that Section 1202 requires for the gain exclusion. Instead of paying tax on the gain, you can roll the proceeds into newly issued QSBS from another qualifying C corporation within 60 days of the sale. The gain is deferred, and the replacement stock inherits your original holding period: it starts life already three years old, needing only two more to reach the full five-year exclusion. The mechanics have sharp edges. You must have held the original stock more than six months, and the 60-day reinvestment window is brutally short with no extensions — which in practice means lining up the replacement investment and your tax advisor before the sale closes, not after. To defer the entire gain you must reinvest the full proceeds; reinvest less and the shortfall is taxed now. The deferred gain isn't erased — it reduces your basis in the replacement stock, so it resurfaces when you eventually sell — unless the combined holding period crosses five years and Section 1202 excludes it entirely. The election is made on your tax return for the year of the sale. This is general information, not tax advice. ### SPV https://signed.com/learn/glossary/spv A Special Purpose Vehicle (SPV) is a legal entity (usually an LLC) created for the sole purpose of making a single investment. SPVs are commonly used by angel investors and syndicates to pool capital from multiple investors into one investment. The SPV appears as a single line item on the company's cap table, simplifying things for the startup. A typical use case is a syndicate. A lead investor finds a deal, sets up an LLC for it, and 30 smaller investors each put $5,000 to $25,000 into that LLC, which then writes one $400,000 check to the startup. The company sees a single clean line on its cap table instead of 30 separate angels, which founders strongly prefer, and the smaller investors get access to a deal they could never have reached on their own. The tradeoffs are fees and control. SPVs usually carry setup and admin costs, and the lead often takes carry — commonly 20% of the profits — plus sometimes a management fee, so your net return is lower than your gross. You also typically don't get information or voting rights directly from the company; you're a member of the LLC, and the lead handles the relationship. When you measure performance on an SPV investment, it's worth looking at net MOIC and net IRR after those fees, since gross figures can overstate what actually reaches you. ### TVPI https://signed.com/learn/glossary/tvpi Total Value to Paid-In (TVPI) measures the total value of your portfolio (both realized distributions and unrealized paper value) relative to the total amount invested. A TVPI of 2.0x means your portfolio is worth twice what you put in, counting both cash returned and current paper value. Unlike DPI, TVPI includes unrealized gains. TVPI gives you the complete picture by adding two things together: cash already distributed plus the current paper value of everything you still hold, divided by what you've put in. Invest $200,000, receive $50,000 in distributions, and hold positions currently marked at $350,000, and your TVPI is 2.0x ($400,000 of total value against $200,000 paid in). It's the most flattering of the standard metrics because it counts unrealized markups that haven't turned into cash yet. The way to read TVPI is always alongside DPI. TVPI minus DPI is, roughly, your paper gains — the value still locked inside companies that haven't exited. A portfolio at 2.5x TVPI but only 0.3x DPI is promising on paper but largely unproven; one at 2.5x TVPI and 2.0x DPI has already delivered most of its value as real cash. Early in a portfolio's life, TVPI carries the story while DPI sits near zero; over time, the goal is to watch DPI rise to meet TVPI as paper value converts into distributions. ### Valuation Cap https://signed.com/learn/glossary/valuation-cap A valuation cap is the maximum company valuation at which a SAFE or convertible note converts into equity, regardless of how high the priced round is actually valued. It rewards early investors for taking on early risk by locking in a ceiling price: if the company raises its next round above the cap, the early money converts as if the company were worth only the cap amount, buying more shares per dollar. Here's the cap doing its job. You invest $25,000 on a SAFE with a $5M cap. The company does well and raises a priced round at a $20M pre-money valuation. Without the cap, your money would convert at that $20M price; with it, you convert as if the company were worth $5M — four times cheaper, so you get four times the shares the new investors get for the same dollar. The cap is the early investor's reward for committing before the company had proof. Caps usually work alongside a discount, and the investor gets whichever produces the better price. If the round prices below your cap, the discount (commonly 20%) applies instead; if it prices above the cap, the cap wins. A lower cap is better for the investor and more dilutive for the founder, which makes it the key number to negotiate on these instruments. One nuance worth knowing: with a post-money SAFE, the cap is measured against the post-money valuation, which makes your resulting ownership percentage straightforward to calculate at signing. Until a priced round happens, the cap is effectively your stand-in for a valuation. ## Blog Posts ### Tracking $150M https://signed.com/blog/150m — published 2026-10-26 Signed is now tracking over $150M of assets. ### Now We're Pretty https://signed.com/blog/new-design — published 2026-10-23 You might have noticed a new look filtering through Signed the last few weeks, starting with our new homepage. Today we’re finishing that work, with a new portfolio view, new company views, and lots more. The New Dashboard The most noticeable change is the new Dashboard. Your portfolio itself isn’t some static spreadsheet; things are happening. The new Dashboard shows off more of a timeline view, so new pitches, investor updates, investments, and other events bubble up right to top-of-mind so you can keep a better view into what’s happening today. Still like the old table view of all your holdings? There’s a new Holdings tab that brings you the familiar spreadsheet view. It’s also a sticky selector, so clicking on Holdings will default that as your main signed.com view until you change it. The New Company Pages The main interactions you have with your portfolio companies on Signed are on the company pages themselves. We’re introducing a new unified timeline view here, too. The data you need most is right up top: your position’s value and metrics, and the holdings you have with that company. Then we go into a timeline view, giving you a good progression over the years of how your interactions have fared with the startup. This is where your notes, events such as SAFE conversions, and any sales or distributions go. Additional Bits Other areas that got some polish: there’s a new Company Holdings page that goes into deeper detail about your shares, a more performant command bar (cmd+K), WCAG 2.2 AA compliance across the app, and some changes along our new multi-currency support and .docx/.xsls previews. You'll notice tons of little quality-of-life improvements, too! Enjoy the fresh kicks. Heja Signed! ### Multi-Currency https://signed.com/blog/multi-currency — published 2026-10-15 Your next startup investment might be in the US. Or England. Or China. Good ideas come from everywhere, and everywhere includes more than just the US Dollar. Signed is now multi-currency. There are 30 currencies to pick from, and every investment can be in a different one. Every check keeps its own currency This is the main idea behind how we built it: a €50,000 check is a €50,000 check. It doesn’t quietly become $54,000 in our database and then drift around every time the exchange rate moves. We store it in euros, because you invested in euros. We also convert it into your home currency, which is what your whole portfolio adds up in. We do that once, at the exchange rate on the day the money left your account, and then we keep that number. Your cost basis is what the investment actually cost you. It doesn’t change when the euro has a good week. What does move is what the investment is worth today. Current value converts at today’s rate, which means your returns in your home currency include whatever the exchange rate did along the way. That’s the honest answer, even if it isn’t always the fun one. Currency Magic™: now with currencies Currency Magic™ already expanded 2.5m into $2,500,000 and did quick math like 50k * 3. Now it also understands currencies. Type €50k, 50k chf, CHF 1.5M or £2.5k + 500, and the field picks the currency and expands the amount. Hover the Currency Magic™ label for a quick reminder: Settings has a new Currency page. Choose your home currency there, and how you like your numbers written. Number format matters as much as currency, especially when you’re typing into a money field and 25.000 could mean twenty-five or twenty-five thousand. Whichever format you pick, Signed reads what you type in that same format. If you change your home currency, we convert every check again at the rate from the day it went in. We don’t use today’s rate for that. Currency, currency, everywhere, and not a drop to drink Typing amounts into forms is the easy part. Plenty of money gets into Signed without you typing it: • Imports. AngelList and CSV imports read the currency from each row, whether it’s a symbol, a code, or a currency column. They don’t assume dollars. • Forwarded email. When you forward an investor update or a pitch to inbox@signed.com, we read €5M ARR as five million euros, not five million dollars. • Pitch decks. Round terms and financials pulled from a deck are read in the deck’s own currency. • MCP. Your AI assistant can log a check in any supported currency, and it knows your home currency. • Exports. Your CSV export now includes each row’s currency, its home-currency amount and the exchange rate used. Now go write that check in krónur. ### Receive Pitch Submissions on Your Site https://signed.com/blog/pitch-submissions — published 2026-10-12 Signed's pitch pipeline is the best in venture capital. It's a way to accept pitches — either from founders browsing Signed, or from pitches you create manually or through forwarding emails to inbox@signed.com — and then put those pitches into a diligence cycle so you can figure out which pitch makes sense to invest in. We're adding a new feature for the pitch pipeline today: you can now take a white-labeled approach and embed the pitch submission process right on your existing website. You can start by going to your Embeds page in Settings- at the bottom of the page is a new Your own pitch form section: Since no one writes code anymore, this comes in the form of a prompt. You can see the prompt or just copy it with the button above and shoot it over to whichever agent you're using. Your agent will then create the form for you with the correct fields, making sure to use the existing look and feel of your website. And that's it. You'll be able to receive pitches from your fund or angel website, and you'll get notified over email when it's ready for you to review. As always, we'll parse out the pitch deck, any financial metrics that could be helpful for you in diligence, and other things we can find that will help you make smarter and better investing decisions. Looking for what's possible with this approach? Check out @matanya's custom pitch page on his angel fund website: exigence.vc/pitch ### Runway in Investor Updates https://signed.com/blog/investor-update-runway — published 2026-10-01 When you forward an investor update to us, we'll parse it and respond back with some quick highlights from the update. Now you'll also see a runway indicator in those emails, too: Just another quick visual indicator on how your portfolio company is doing. Now go help extend those runways. ### All Paid Plans Can Now Receive Pitches https://signed.com/blog/paid-pitches — published 2026-09-28 Quick little update: all paid plans can now receive startup pitch submissions — previously that stayed in the realm of the Investor plan, but now those on the Angel plan can bathe in the glory of dealflow. These submissions are tied to your user profile, so you'll be able to receive pitches at: signed.com/@your-username/pitch ### Support for .docx File Previews https://signed.com/blog/docx-previews — published 2026-09-28 Hot off the heels from our recent new support for .xslx and .csv file previews in Signed, we now have support for previews of .docx files. So the next time your lawyer wants you to read through the weirdest Microsoft Word redline, don't worry; we got you. ### Support for .xslx, .csv File Previews https://signed.com/blog/spreadsheet-previews — published 2026-09-26 When you get the big ol' bundle of round closing docs from your portfolio company's fundraising — or their demise — you'll sometimes get some spreadsheets thrown in among the PDFs as well. We now support previewing that file right on Signed, no download necessary: Click, and they'll show up in the familiar preview that we use for PDFs: Spreadsheet away to your heart's content. ### Find Angel Investors Through MCP https://signed.com/blog/angel-investors-mcp — published 2026-09-24 Signed already has a directory of angel investors, and now your AI assistant can read it too. Add mcp.signed.com/investors to Claude, ChatGPT, Cursor, or whatever you use, and ask it things like who writes $25K checks into climate companies? or which of these angels actually takes cold pitches? It’ll find them, tell you what they invest in and who they’ve backed, and point you to the right place to send your deck. You don’t need an account or a password. Just paste the link and ask. Investors Are you an angel investor and want to be included in the directory? Just sign up for a free account, easy peasy. For existing investors, all of this still protects your portfolio information, of course; the public MCP server only searches over investors who have made their profiles public. If you want founders to find you, make your profile public in Settings and fill it in; it's free. The more full your profile, the higher you show up. If you’d rather have your AI help with your own portfolio, you'll want our portfolio MCP at mcp.signed.com. That one needs you to sign in, for obvious reasons. ### Sectors https://signed.com/blog/sectors — published 2026-09-22 We now have Sectors in Signed: Sectors are from a set list: these are the sector breakouts we use on pages like the angel investor directory. Are sectors comprehensive? No. Are they an attempt at trying to make a general bucketing of companies that can help you compare and contrast between investments? Sure! When we first see your company or pitch, we'll try to categorize it into a Sector based on the information we have at hand. You can always remove or override any Sector decisions. We also have tags on Signed as well- those haven't changed. But now tags are much more oriented towards how you decide fit. You may tag something YC26, or To-Review, or any sort of categorization scheme you find helpful, and leave the sector classification up to us. ### Pulley shutting down: find out how you're affected https://signed.com/blog/mcp-search-facets — published 2026-09-18 This week, Pulley announced that they were shutting down. It's a real bummer; they were a lovely addition to the industry, and it was fun to see fresh blood in the space. Beyond that, though, a natural reaction for an angel investor is to wonder what their personal exposure is to this, and how they might have to shift things around in the coming months. The first step is to use our new search facets on our MCP server for investments to see how many of your portfolio companies use Pulley for their cap table: Pulley is winding down on December 8, 2026; in the meantime, a lot of the weight is shouldered by your founders, who will have to find a different path to take for their cap table management. One thing you can be proactive on is to reach out to those companies (or mention it in your next meeting with them) and shoot them a link to Pulley's shutdown FAQ, if they haven't seen it already. When dealing with cap tables and legal structures, it doesn't hurt to be a little ahead-of-the-curve, since these types of moves can take some time to accomplish. All of this is a nice benefit of ensuring you have clean data within your holdings on Signed; you'll be able to make these quick decisions via MCP or through our own website and be ready for whenever the next corporate event happens. In the meantime, if your companies are moving to another provider that's not listed within Signed, let us know; we'd be happy to add more custodians to Signed (and eventually integrate with them directly). ### New UI: Company sidebars and investor updates https://signed.com/blog/new-ui-sidebars-updates — published 2026-09-17 Quick splash of paint today! We now have a more refined sidebar that notes all of your favorite investment and startup metrics on the right sidebar on any company or pitch page. Just look for this new widget: Our investor updates have gotten a similar treatment, too. Now when you forward an investor update to Signed, you'll see a more glanceable top box denoting the metrics that we imported and measured from that startup's email: Now's a good time to remind you that these investor updates are great snapshots-in-time, too. Have a good JavaScript candidate in mind but can't remember which of your portfolio companies was looking for a JavaScript developer? Just search for "JavaScript" across your entire portfolio's history and see which startups might be a good landing spot for your them. ### Tracking your startup's runway https://signed.com/blog/startup-runway — published 2026-09-12 Venture-backed startups live by the cash and die by the cash. On occasion, you might run into a portfolio company that tries to downplay their current financial state. There's a big deal in the pipeline, or some cost savings coming, or a new feature's really going to kickstart revenue. That's all well and good, but money is the metric that cuts through that. We already parse and import investor updates from your portfolio companies; you can also manually go in and add a new metric if you just got off a phone call, for example. Signed tracks a few different things: ARR, cash, burn, and now a runway. You'll see it in your company listing when you sign in, and also on the company sidebar. We're now extracting those latest metrics from any update we have on a company and floating them up higher so you can see the import stuff right away. Signed also calculates a runway- a basic calculation of how much time the company has to live before the burn rate outweighs the cash on hand. This obviously can go up and down depending on costs, revenue, and financing rounds, and we'll keep adjusting the runway accordingly. We'll also show an idea of where the company might be at today. In the image above, for example, you can see the green bar indicates the runway available when the investor update went out. But it's been a bit of time, so the today marker has moved closer to zero. The longer time passes without an update, the less accurate the runway calculation will be (and that's a great time for you to talk to your founder and get the low-down!) Enjoy your burn! ### New logo https://signed.com/blog/new-logo — published 2026-09-06 Hi. We have a new logo. ### MCP: File uploads https://signed.com/blog/mcp-file-uploads — published 2026-09-06 Our MCP server launched as a way to ask your portfolio questions; now you can run through the whole pitch pipeline, end-to-end. Our previous release added pitch pipeline changes, where you can add new company pitches to your account. Now you can add (and remove) files from those pitches. So if you have a slide deck coming in from an email, or your agent is helping you power through your pitch triage, you can also add to the data room of those pitches. One example we've been having fun with: using deckk to take a pitch deck's URL and convert it to PDF, so Signed's built-in PDF AI analysis tools can summarize and make it searchable. As always, head to mcp.signed.com to set your agent up. ### MCP: adding and updating deals https://signed.com/blog/mcp-pitches — published 2026-08-27 Quick little update for our MCP server: you can now create and update pitches. So now you can just give your AI assistant a nudge, like: add the company I chatted with over lunch to my Signed pitch pipeline, or I'm going to pass on the deal from the company I met this afternoon. We'll always be adding more fun capabilities to our MCP server, so keep an eye out. Or have your agent keep an eye out. Agents are doing everything anyway. Except this post. This post was written by a human. Totally. Anyway, happy MCP'ing! ### Reporting: your pitch pipeline https://signed.com/blog/reporting-pitch-pipeline — published 2026-08-24 Part of Signed's biggest strength is having it take over your pitch pipeline: in other words, managing and tracking the companies you're talking to prior to deciding whether or not to invest. With our new Reporting dashboard for Pitches, you can dig into how you manage that pitch pipeline of companies. For investors that have startup pitches submitted via Signed, you can now dig into the metrics around companies submitted to you: things like how responsive you are, how selective you are, and when you tend to pass on investing. Users on the Investor plan now have access to the new Pitches dashboard. Can't improve a process without collecting the data first! Happy diligence-ing. ### Track your pro rata https://signed.com/blog/track-your-pro-rata — published 2026-08-21 One of the more important aspects of startup investing is securing pro rata: the right to re-invest in a company's future round in order to protect against dilution in the company. Pro rata is helpful when you're trying to double down on your winners: power law means your most successful winners will likely make up the lion's share of your entire portfolio. If you do have pro rata rights, it'd be helpful to track that so you have a general understanding of how much cash you might want to set aside for future rounds. Luckily, Signed can help with that now! We have a new Pro Rata Dashboard available for those on the Investor plan: This page will give you at least a rough idea of which startups you have pro rata rights for. The actual amount required to protect your ownership will depend on the valuation of the company's next round, of course, but this can form a good first step to understanding what you might be looking at. To mark a company transaction as having pro rata rights, there's now a checkbox on the holdings table within a portfolio company's page. It functions similar to the new QSBS checkbox as well: check the box, and it'll get marked in the new reporting dashboard, as well as the company sidebar. Happy... pro-rata-ing? ### Tax estimates across Signed https://signed.com/blog/tax-estimates — published 2026-08-18 In your Settings page, you'll see a new Taxes section. When you fill in your tax bracket information and your state tax treatment, Signed will give you an estimate of your tax liability: This view is on your Reporting dashboard, but we're also adding quick net value on your dashboard, your Tax Reporting dashboard, and other places around the site. It goes without saying, but your CPA — and the IRS — will have the final say on your tax liability, but the aim for Signed is to help you with a general understanding of what your potential state and federal liability might be. A little bit goes a long way when you're planning your portfolio. ### QSBS Calculator https://signed.com/blog/qsbs-calculator — published 2026-08-12 Next up on our tax week ships: the last QSBS Calculator you'll ever need. In building out our new QSBS Clock feature, it became apparent that... sheesh, there's just so much happening when you talk about QSBS. You have to keep in mind your state's application of QSBS, your company's asset level, when exactly you acquired shares, which form of QSBS your shares apply under, and a bunch more. So we made the end-all be-all QSBS calculator you'll ever need. It's all free to use and doesn't require signup, of course; just jump right in and use it. It's a good way to get a gut understanding of what your eventual return might look like, and whether you should jump into a secondary or a tender offer today or bite the bullet and wait until you can fully apply QSBS exclusions to your stake. Give it a spin! ### QSBS Clock: Track all your QSBS-qualified investments https://signed.com/blog/qsbs-clock — published 2026-08-11 It’s tax week at Signed! We have a slew of new features around taxes, QSBS, and other *insanely exciting topics* this week! Don’t act like you aren’t incredibly looking forward to improving your tax strategy, you little freak. The first ship comes today: the QSBS Clock. QSBS QSBS isn’t just a weird BS acronym: it’s one of the single most-lucrative tax advantages you can take advantage of. Qualified Small Business Stock has been around for decades, letting owners of early-stage company stock avoid paying tax on gains. Your first $10M-$15M of gains *per company* are tax-free (or 10x your basis, whichever is larger). It’s a pretty insane giveaway (which is the point: it encourages investment into early-stage, innovative companies). There are a number of caveats: companies must be under an asset number to qualify, your state — like California — might still tax your proceeds, the year you invest can play a big role due to last year’s changes in the OBBBA, you must hold it for a certain time period, and you must hold converted stock instead of a SAFE or similar. (Boy, this is a headache! It’s almost like a certain angel investor platform should launch a comprehensive tool to help with this. Check back tomorrow on that ) QSBS Clock Signed has had a simple QSBS flag for months, but we’re digging much deeper into your holdings now with our new QSBS Clock. You’ll see it in your Reporting page. Think of this as a high-level dashboard into companies that you’ve marked as being QSBS-qualifying. We handle all of the myriad scheduling differences between Classic QSBS™ and the more recent OBBBA QSBS from 2025 (and we’ll update these rules accordingly as they start changing in 2027 to adjust with inflation). We also handle all of this across multiple lots: if you have multiple checks into a given company, we’ll track your exposure separately for each lot. The primary question this screen answers is *which company stock should I continue to hold longer?* in order to leverage tax treatment. This might just be trivia that could be interesting to your portfolio, but if you’re considering taking a tender offer, selling part of your holdings in a secondary sale, or there’s an upcoming exit on the horizon, this is a fantastic sanity check (and a good idea of what your tax exposure might be). Determining *when* to exit a position can potentially save you thousands or millions. You can get started by editing a holding on a company page. We’ll also give you the full clock for that position on the sidebar: Helpful for employees, too This benefit isn’t just helpful for investors; depending on how you acquired your shares, your equity plan from your employer might qualify under QSBS as well. It’s another reason why tracking your sweat equity like any other investment really matters: don’t leave money on the table. Thinking about this as an employee can help you understand when it makes sense to exercise your options (if you didn’t already 83(b) on an early exercise of your options). That the clock only starts on exercise, not grant, has a huge impact on your whole schedule. You can also potentially roll your QSBS proceeds into a new QSBS position if you’re looking at an early exit as well (through Section 1045). But first: you have to track all this to understand how it impacts you. MCP access Of course, this is all live in our new MCP Server now as well. Point your LLM at mcp.signed.com, sign in, and ask it questions like: “which positions can I sell today without giving up a QSBS exclusion?” Digest access This is wired into our new Portfolio Digest emails as well. Since so much of QSBS treatment surrounds *when* you do certain actions, we’ll surface any upcoming QSBS milestones coming up in the next quarter in your weekly email as well. The Clock Marking a position as QSBS-qualifying is free for everyone, but the QSBS Clock and its reporting tools are available on the paid Investor plan. Happy QSBS’in! ### Signed’s MCP Server for AI assistants https://signed.com/blog/mcp-server — published 2026-07-28 Today we’re launching an MCP Server for your investment portfolio. MCP At its core, MCP just enables your AI assistant — Claude, ChatGPT, Gemini, OpenClaw, whatever —  to have direct access to your data. You aren’t tied to whatever we at Signed build for you; you can ask your AI agent to read your data, write new data, present it in weird and funky ways, whatever you want. It’s pretty easy to get started: just add `https://mcp.signed.com` as a custom MCP server in your favored AI agent, and then it’ll prompt you to sign in to Signed over the familiar OAuth protocol that the web has been using for years. Important Business Queries There’s a *bunch* of stuff you can do to get a better handle on your angel portfolio. You might use it to get better at selecting startups, or improve your communication with your portfolio companies, or to help find blind spots in your own selection approach. You can ask your agent questions like: “Read every note and pass reason in my pipeline and tell me what my actual investment thesis is — not the one I say I have.” Or: “Read the last two quarters of investor updates and flag the companies that are quietly slowing down — where the tone shifted before the numbers did.” Or: “Compare the companies I followed on into against the ones I didn't. Did my follow-on instincts add value, or would blind pro-rata have beaten me?” Or: “Draft my annual letter to myself, LP-style: what I deployed, what worked, what I'd tell myself twelve months ago.” The idea, like all things on Signed, is to get you to become a better investor, generate higher returns, and help your portfolio companies out. Workflows A lot of the benefit of AI is that can help step in and facilitate a *workflow* during your investment process. From that perspective, you’re not just doing a more static prompt-and-answer process with your companies… you’re building a process that can be proactive and keep you focused. Which is a lot of words, of course, but what does it actually mean? A few things I’ve personally started doing with my agent over the last month that have helped out a ton: • My agent will ping me every day if there’s a pitch that’s been in my pitch pipeline that I haven’t responded to or updated in a couple days. I hate the black hole that startup pitches sometimes face, and I really try to stay on top of my diligence pipeline so founders aren’t waiting on me for so long. (I mean, they still do, but I’m working on that.) • I generate notes from most of my meetings. My agent will notice the new meeting notes from Granola, determine if it ties into a company in my portfolio or pitch pipeline, and then add the meeting notes as a Note attached to that company. This has been wildly helpful to have this data in conjunction with another feature that we’ll be shipping in the near future, too. • As an angel, it’s my money I invest, and I have a few types of founders and companies that I just do not invest in. When a new pitch comes in to Signed, my agent will diligence it from that cultural fit perspective and then post a comment on the pitch with what it found. This has helped me save everyone some time by being able to pass earlier than normal, skipping a meeting or two that wouldn’t end up going anywhere. One you get into the habit of thinking of workflow rather than just prompts, you realize how many proactive things you can build into investing to allow you to focus on what really matters: helping companies grow. Funsies Obviously with AI you can do whatever you want, though. We’ve been having a lot of fun with some less-obvious prompts, too: “Assume I'm a genius and every pass was correct. Write the press release announcing my new fund on that basis.” Or: “Make the strongest possible case that my worst investment was actually my best one, and that I'm the only person who can see it.” Or: “Write my portfolio's 2030 obituary assuming everything went wrong. Then write the one where everything went right.” This one was particularly amusing, ending with this lovely bit of prose: “Signed, the tool built to make sense of all this, remained the best-instrumented and detail-oriented view of a portfolio that was inevitably doomed.” That might be our new tagline: Signed, where you know down to the penny how much money you’re burning. AI Jokes aside, Signed over MCP has been pretty spectacular to use over the last few weeks. Much like the transition from “a mediocre angel investment spreadsheet” to “everything is detailed in Signed” was a large leap, going from “everything in Signed” to “everything can be investigated now” has been eye-opening. Give it a shot! ### Portfolio digests https://signed.com/blog/portfolio-digests — published 2026-07-20 A lot of things happen in your portfolio on Signed! From founders sending you new pitches, to investor updates getting parsed and filed away, to all your metrics staying updated and recalculating in real-time... it can be a lot for a fancy-pants investor like you to stay on top of it. We're adding portfolio digest emails today to Signed. Each Monday we'll shoot an email with the details of what happened the last week in your portfolio: It's designed to give you a quick heads-up on your investments, like: giving a heads-up on pitches you might not have diligenced yet, any valuation marks that happened, the latest investor updates, new features from Signed itself, etc. These will send out weekly if you have interesting things happening in your portfolio recently; otherwise, we'll downshift it to monthly for a larger recap on everything. And, of course, you're always in control! Just hit unsubscribe or head to your email preferences if you want to change these settings at any point. ### Pitch Economics now track discounts https://signed.com/blog/pitch-economics-discounts — published 2026-07-08 Hot off the heels of our new pitch economics sidebar in your pitch pipeline, we now auto-extract and track discounts of that particular investment's raise: There's also a nice new visual showing how close they to completing the round. As always, all of these metrics can be one-clicked to enter and update the values, or we'll auto-extract them from the pitch deck, any notes you've entered, or other details you might be tracking about the company. ### Notes on Markups https://signed.com/blog/markup-notes — published 2026-06-27 Quick addition to the site: you can now add some notes to yourself when you change a company's valuation. When you click on Update valuation on a company, you'll see a new section of the form: Depending on how you want to track your valuation markups (and markdowns), it's a helpful spot to note any SPVs you might see, secondary sales, or press releases for new fundraising for your portfolio companies. We'll also show it in your investment timeline, too: ### Financials for a startup pitch https://signed.com/blog/pitch-economics — published 2026-06-10 When someone pitches their startup to you, you'll see a new section detailing the current round on the sidebar: You'll get a quick look at valuation, revenue, and raise details. To add or change them? Just click each and update it directly (and, of course, you can use Signed's Currency Magic™ to quickly add these values). Having to press keys like a Neanderthal really turning you off to using this feature? No matter. Like most of Signed, we also run the pitch deck and all your notes through an LLM to pick these numbers up for you without you lifting a finger. Once a pitch has been added to your pipeline, we'll go through everything we know about a company and pre-fill those values that we find. ### Paint it black https://signed.com/blog/dark-mode — published 2026-06-09 Signed's future might be bright, but this website ain't. We've been flirting with it since launching, but decided to rip off the band-aid and go full dark mode. Should make your up-and-to-the-right charts pop even more. We've also made a few other changes- going to a more functional header instead of the dangling-left-sidebar, as well as updated the Blog and our area to Learn about angel investing to also ditch the bright blue backgrounds. Will it make you a better investor? Probably. I mean, it worked for Bloomberg terminals, can't be bad for you. ### Secure your investments with Passkeys https://signed.com/blog/passkeys — published 2026-05-29 Your angel portfolio has a lot of sensitive data in it: both financial (your economic performance) and legal (startups share privileged data with you). Makes all the sense to worry about who can access that information. Today we're adding a new multi-factor authentication to Signed: Passkeys. Passkeys have been slowly taking over security on the web; traditional methods like SMS authentication has been broken for quite some time, and Passkeys is seeing strong support in browsers, OS integration, and password managers like 1Password. You can set up your own Passkeys in a new Passkeys page in Settings. A couple notes to keep in mind: • You'll want to have Passkeys generated on more than one device, so if you lose your phone or your laptop you have a backup so you can continue to sign in to Signed • You'll also be able to download a set of recovery keys, for when everything Goes Wrong and you need to use one of your backup codes to access your account. Save 'em in a safe place. • Once you enable passkey sign in, you no longer can sign in with your email and password. Once set up, signing in is a one-click operation (depending on how your browser or OS is set up): ...then enjoy your hecka secure account. 🔒 ### Global file upload for investment docs https://signed.com/blog/global-file-upload-for-investment-docs — published 2026-05-04 A big part of your angel portfolio is the part that touches the files of each investment: pitch decks, legal documents, financial projects, and so on. Signed is designed to take all of that in, make it searchable, and let you ask questions and query it. Today we're adding something that we're calling Global File Upload. Previously, you could be on the "Files" tab of a given investment, or on the new investment screen, and you could simply drag and drop a file to attach it to that specific company. Now, you can do that anywhere. Any time you're on a page on Signed, you can drag and drop a file on desktop to the browser window and you'll get dropped into a new upload flow: At this point, this triggers a number of things: • your document gets analyzed by AI (if you're on a paid account) for information about the company and the investment • if it's a pitch deck or deal memo, we'll start crunching highlights and a synopsis of the company so you can learn more about it • we either add it to an existing company, or create a new company or pitch if we haven't seen the company before AI isn't everything, though, and sometimes it does make mistakes. There's a new "merge company" button at the top of new company and pitch pages now, which lets you merge an errant new company in with an existing company. We'll also attempt to de-duplicate any investment details if you've already included them on the previous company. If you're already looking at a company and you just want to add another file to the company without worrying whether the file will match that company or not, you can just drag and drop onto that page and we'll add it directly. If you're adding a new file to a different company, you can also drag it to that new company instead: This'll all help you more quickly create new companies, track dealflow, and attach your docs to the right place! Happy... attaching? ### Embed your investments https://signed.com/blog/embedding-investments — published 2026-04-27 Hey you! You, that wonderful investor you. I bet as the dashing and forward-thinking startup investor that you are, you probably have a website, or blog, or tiny piece of the internet to call your own. And that's great! Because you can use it as your own platform to attract founders, build dealflow, and generally improve your angel investing portfolio as you go. Signed now has a quick and easy way to embed your portfolio and investor profile on your website. Here's a few live examples of what you can do: Pitch a startup Makes it easy for your readers and users to submit directly to your Pitches section on Signed, so you can collect their pitch decks, company information, founder information, and all sorts of things. Your investor profile We've been adding more focus on social investing as of late: the idea that who you are as an investor matters, and how you interact with the rest of the angel investor community matters as well. This embed gives you a quick and easy way to show off your background. Your highlighted investments Finally, you can show off some investments you'd like to highlight. You know, those big, awesome, interesting wins you've found as an investor that you'd like to use to attract other founders to your portfolio. And naturally, these promoted investments are all explicitly opt-in: we won't display anything unless you select your highlighted investments on your settings page. The fun part of all this is, of course, it's all kept up-to-date right along with all your normal portfolio needs on Signed. If you've ever tried to keep a list of investments or details about what you look for up-to-date and current on your About page... well, you'd know that's the first to be ignored as you focus on other more fun stuff. So: embed away! ### Inline company edits https://signed.com/blog/inline-company-edits — published 2026-04-18 You can now edit the company name and URL right from your sidebar: You know, for all you who haven't added full domain data to your investments. It's very hip and cool, and unlocks a bunch of stuff now and in the future- so when you see an investment without a domain... fill 'er up. ### Timeline filters https://signed.com/blog/timeline-filters — published 2026-04-16 Quick little update this morning: there's now filters on your portfolio's Timeline page, so you can quickly dig into the activity that's happened across your investment portfolio. ### Search across your investments https://signed.com/blog/search — published 2026-04-14 We've had a search view for a minute, but today we're rolling out a "proper" search view: The new search page searches across all the things you need: companies and pitches, obviously, but also people, any notes you've added to a company, through all investor updates any company might have sent out, and inside (most) documents you upload to Signed. Great for things like finding which companies are hiring Rails developers, or which investment might need you to update your physical address, or which founder you invested in says things like "cracked" most. And then you can refuse pro-rata accordingly. This, of course, goes-hand-in-hand with our universal cmd+K hotkey available on all signed-in pages, which lets you do a quick search across your portfolio. ### New fund and SPV view https://signed.com/blog/updated-fund-view — published 2026-04-02 The page for both funds and SPVs have been updated today: Buncha stuff in today's quick update: • Fund-level metrics and charts right at the top for the vintage aggregate (so you can get a view at a glance as to how your investments are doing at a venture firm or SPV manager) • Quick progress bars on capital calls and overall allocation for that fund, to compare weight between investments • You can dig into each individual fund vintage or SPV investment to note capital calls, update the performance of each individual fund, and so on Enjoy your LP experience just a little bit more now! ### DPI https://signed.com/blog/dpi — published 2026-03-29 Next time you sign in you'll see a DPI — distributed to paid-in capital — metric listed on the dashboard. DPI's a nice alternative measurement that gives you a bit different viewpoint on your portfolio than just MOIC and IRR, particularly when you're trying to answer questions about your own liquidity and cash flow. As always, you can mouseover terms like DPI and IRR within Signed to get a quick understanding of what a particular investment jargon™ actually means. ### Currency Magic™ https://signed.com/blog/currency-magic — published 2026-03-13 If you've spent large chunks of your life entering numbers into web forms, you know they can be a bit... limited, at times. For our currency fields across Signed, we have a nice little shortcut to saving some time or braincells: Currency Magic™. It'll let you auto-expand amounts with a lot of zeros as well as do some basic arithmetic right in the input field. Just a little niceness. ### Exports: now with files https://signed.com/blog/exporting-files — published 2026-03-12 Recently we added a data export for all your investing-related information; the backup process now has the power to suck in all of your various files you've uploaded to a company or pitch and throw them in the zipfile, too: ### Social links https://signed.com/blog/social-links — published 2026-03-10 Hot off the heels of our social investing additions, we've added some additional slots on your public profile to add your social media presence as well. Check 'em on your settings page. ### Social investing https://signed.com/blog/social-investing — published 2026-03-06 Investing is inherently a social activity: founders meet investors, investors recruit other investors to put a check in, then everyone recruits employees to help work on the company. Strangely, the whole thing is gatekept as some sort of special dance behind closed doors, where you have to know the right people to talk to so they can know the right people to talk to. It's actually strange there isn't some sort of list of angels to refer to if you're searching for other angles, for example. (You could call it... an "Angel Listing" maybe. Weird no one's done that before.) Some of the more interesting things we have planned for Signed is improving the social aspect of investing, and today there's a new experience for your user profile (here's mine, for example). It looks like this: Think of it as a quick little overview into your investment background- you can pop some highlights of previous investments up top, put a little background on how you invest, and then select some categories that you invest in so you show up in the investor directory. If you have an Entity set up, you'll be able to use this as a place to collect pitches from investors, too. This is, of course, all completely optional: everything is private by default, and you can pick and choose which companies and information to put out there (and most importantly, all of your portfolio's financial data and notes are never public). There's going to be a lot of fun stuff to come in terms of dealflow and other aspects of dealsharing, so sign up for the waitlist if you're interested in grabbing your @handle and onboarding soon! ### Export your data https://signed.com/blog/exports — published 2026-03-03 This goes without saying — although it's becoming harder and harder to see other companies say this — but your data is yours. And the data about your investments is doubly so. Quick little update today: export your data. Click a button, get all your investment details in a simple CSV for export to other systems, or just as an offsite backup for piece-of-mind. ### SAFEly have IRR in your SPV's MOIC https://signed.com/blog/definitions — published 2026-02-21 Venture capital has quite a language of its own. Like any fancy financial discipline, it's made up of a ton of acronyms to make the people in the space work faster and/or feel special. Part of what Signed is here for is to increase literacy for people just getting into investing and startups, so we've started adding little tooltips across the site explaining what weird term we might be using here. If you're confused by something, give it a little mouseover and hopefully we'll have a nice little explanation for you right there. ### Beta testing https://signed.com/blog/beta — published 2026-02-20 Made an announcement, so I guess we can say the beta is open now. Add your email to https://signed.com/signup to get added to the waitlist; we'll get you on board soon enough! ### Home sweet /home https://signed.com/blog/home — published 2026-02-17 Gone are the days of just a cryptic logo on the front page; welcome to having a real landing page! We're getting a bit more public, little by little, as we storm towards launch. This also gives a bit more color on what the hell we're actually building here. So enjoy. Enjoy a landing page. That's a phrase that's never been typed before. ### Public pitches https://signed.com/blog/public-pitches — published 2026-02-10 Signed has had public pitches for a bit, but we just gave them a freshen-up with a new design and some improved interactions during the submission form. You can take a look at Tifo's public submission page if you'd like. All of this helps with tracking the pipeline of pitches and intros you might see as an investor: new pitches get added into your Pitch dashboard, where you can use Signed's tooling to dig into the company further. ### Import your AngelList portfolio https://signed.com/blog/angellist-import — published 2026-02-09 If you've made some investments on AngelList, you can now import your entire portfolio directly into your account. Head over to our Importer and click the "AngelList Imports" link up top to get started. You can do this as often as you'd like; we'll only update the companies and values that have changed since the last time you uploaded your portfolio CSV. Great for the first-of-the-month update you might already be doing across your financial ecosystem today, or if you have the odd one-off update you want to pull into Signed. ### Product updates! https://signed.com/blog/blog — published 2026-02-09 We've been working on Signed for a while now, but as we're getting closer to launch, it's time to start to bring things together in blog form so you can use the new hotness right as they come off the press. So: welcome to the Signed Blog. Signed, Signed. ## Company Information Signed was founded by Zach Holman, who invests out of Tifo. The product was built from firsthand experience with the pain points of angel investing — tracking investments across spreadsheets, chasing investor updates via email, and cobbling together tax reporting at year end. ## Technical Details - Web application accessible at https://signed.com - MCP server at https://mcp.signed.com (Streamable HTTP, OAuth 2.1 with dynamic client registration) - Public MCP server at https://mcp.signed.com/investors (Streamable HTTP, no authentication, read-only, CORS enabled) - RSS feed available at https://signed.com/blog/feed.rss - Sitemap available at https://signed.com/sitemap.xml - Privacy-focused analytics with no third-party tracking cookies