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.
Next up on our tax week ships: the last QSBS Calculator you'll ever need.
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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.
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.
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.
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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:
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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.
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!
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:
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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.
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:
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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.
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:
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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:
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.
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.
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):
