The Signed Blog

Hi. We have a new logo.

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.

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!

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.

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?

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.

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!

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!

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!

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.