Signed.com lets investors see, at a glance, which portfolio companies and funds issue K-1s and which do not. The platform is building an audit page that estimates which tax documents will be ready — and when — so investors know exactly what to hand their CPA. The longer-term goal is a single zip file that packages everything up and goes straight to the accountant, eliminating the usual tax-season scramble.
For an investor with stakes in a couple hundred companies — as is the case for Zach Holman, founder of Signed.com — tax season is not just paperwork. It is a coordination problem. Different entities issue K-1s on different timelines, and some pass-through vehicles never issue them at all. Keeping track of that manually, across a spreadsheet, is where things break down.
Signed.com addresses this by building a dedicated tracking layer: investors can see which of their holdings will generate a K-1 and roughly when that document will land. This is the kind of visibility that transforms a reactive scramble into a planned handoff, a point Holman discusses in detail on The Angel Next Door.
The audit page is the near-term feature: a single view that estimates what documents will need to be handed to a CPA by a given point in the year. It is designed to answer the question an accountant always asks — "what are we still waiting for?" — before the investor even has to pick up the phone.
The longer-term vision goes further. Signed.com is working toward generating a zip file or package that investors can send directly to their accountant. No more forwarding individual PDFs, no more digging through old emails to find a K-1 that arrived in March. As Holman explains in this episode, that kind of consolidation is the real unlock for active angels who have dozens of positions generating tax events every year.
Signed.com launched in February–March of the recording year, with these tax features already readied ahead of that first tax season — a deliberate choice to make the platform immediately useful rather than promise features for later.
"I've invested in a couple hundred companies. I think it's really hard to do that just in a spreadsheet form and trying to figure things out and where to go from this."
Zach Holman — Founder, Signed.com. Holman joined GitHub in 2010 as an early engineer and spent five years at the company before it was acquired by Microsoft in 2017. He subsequently moved into advising, working with companies including GitLab, before transitioning into angel investing around 2018. Over seven to eight years of active investing, he built a portfolio of approximately a couple hundred companies spanning developer tools and sports — including stakes in soccer clubs. Signed.com grew directly out of his own frustration with spreadsheet-based tracking, and he discusses the tax organization problem at length in The Angel Next Door.
The tax pain Holman describes is structural, not personal. When a single crowdfunding campaign — like the Oakland Roots SC WeFunder raise — can bring in four to five thousand investors, the downstream K-1 and document management complexity becomes enormous for everyone involved. Signed.com is targeting precisely that friction point, as covered in this podcast episode.
Signed.com supports direct integration with AngelList, allowing investors to export their AngelList portfolio — including any syndicates — and drag and drop it into the platform for consolidated tracking. This removes the need to manually re-enter positions that already exist on AngelList.
Carta functions as a custodian that tracks share ownership — whether a safe is still active or has converted into shares — but it is often slow to update. Signed.com focuses on the investor's own active portfolio view rather than custodial record-keeping.
Investors can forward their investor updates directly to Signed.com, and the platform uses AI to parse the content, identify reported metrics, and track whether a company's predictions matched its actual results the following month.