Zach Holman treats sports team investments the same way he treats angel investing in startups—by backing things he is personally interested in, even when traditional financial logic would not satisfy standard fund LPs. He has invested in Oakland Roots SC through a cold DM to the club's chairman, joined the ownership group of Cagliari in Serie A Italy, and committed capital to a fund acquiring European women's league clubs.
This approach reflects a fundamental shift in how Holman thinks about capital allocation. Rather than enforcing strict return thresholds or rigid financial metrics, he views sports ownership as an extension of his broader angel portfolio—a place where passion and belief in a project can justify the investment decision, even when spreadsheet returns do not support it.
As Zach explains in the episode, the mindset is straightforward: if he cares deeply about a team, a league, or the potential of a market, the investment makes sense. This is distinctly different from how many institutional investors or traditional fund managers evaluate opportunities.
"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; Early Engineer at GitHub. Zach joined GitHub in 2010 and spent five years there before Microsoft acquired the company in 2017. After leaving GitHub, he moved into advising companies including GitLab, which naturally led him into angel investing. Over the past seven to eight years, he has invested in approximately a couple hundred companies across sectors including developer tools and sports, ultimately building Signed.com to solve the portfolio tracking chaos that frustrated him personally.
The Oakland Roots SC investment came about through direct outreach—Holman simply cold-DMed the club's chairman, expressed interest, and became an investor. That same directness and personal conviction shaped his decision to join Cagliari's ownership structure, one of Serie A's historic Italian clubs. Neither move was the result of a formal deal flow or institutional pitch process; both stemmed from genuine interest in the sport and the potential of the franchises involved.
His participation in a fund dedicated to acquiring European women's league clubs points to another dimension of his sports investing thesis: backing undervalued markets and emerging opportunities. Women's professional soccer in Europe represents exactly the kind of asymmetric opportunity that appeals to an angel investor who is willing to take on risk in exchange for a chance to build something meaningful.
The logic Holman applies is borrowed directly from how he evaluates startups. Just as an angel investor might back an early-stage founder with a vision despite uncertain unit economics, Holman backs sports teams because he believes in the long-term trajectory of the franchise, the league, or the sport itself. The financial return is not irrelevant, but it is not the primary filter either.
This stance acknowledges a hard truth: most angel investments fail or underperform, yet investors continue to participate because the potential upside and the thrill of backing something meaningful justify the risk. Sports teams operate under similar logic—ownership is as much about influence, community impact, and pride as it is about dividend yield or exit multiples.
As discussed in The Angel Next Door podcast, Holman's sports portfolio is not separate from his startup investments; it is part of the same portfolio philosophy. The difference is that sports deals tend to come with fewer historical comparables and more emotional weight.
According to Zach Holman, the key unlock is organizing data around transactions rather than lump-sum entries — maintaining one sheet for company background and another for transaction history allows for cleaner tracking and easier migration to portfolio management tools.
Signed.com is building features to help investors track which of their portfolio companies and funds issue K-1s and which do not, and to create an audit trail that simplifies tax preparation and compliance work during tax season.
Signed.com supports direct integration with AngelList, allowing investors to export their AngelList portfolio — including any syndicates — and drag and drop that data directly into Signed.com for consolidated tracking.