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The Hidden Edge in Dual-Market Investing

I was thinking more about how Thrive Capital’s investment in Carvana positioned them to distribute 0.2 times the cash their investors put into the 2022 fund (see here). That distribution happened in 2025, which was after only two to three years, depending on when the fund closed. For a fund that invests in private companies to return $0.20 for every $1 invested in the fund in just two to three years is amazing. Like I said yesterday, it usually takes five to seven years before any cash is returned.

When you consider the current landscape, in which venture capital (VC) and private equity (PE) funds haven’t been able to return much cash to their investors, that cash distribution looks even more impressive. Many investors in PE and VC funds want to use cash returns from previous investments in PE and VC funds to fund new ones. But that’s hard when your old fund investments aren’t returning cash.

The Carvana investment was definitely an exception. Recovering from a 96% loss to a handsome profit isn’t the norm. But what really stood out to me was that Thrive was investing in private and public technology companies simultaneously. Investing in private start-ups and growth-stage companies requires a unique skill set. You’re trying to make a transaction happen between two sophisticated buyers. Public-market investing is a different animal. You have no idea who you’re buying from; they may or may not be more sophisticated than you. It’s an auction-driven market where price is determined by supply and demand flows.

From my experience, it’s common for investors to be comfortable in either private- or public-market investing, but not both. It’s uncommon for VC investors to simultaneously invest in public companies. Nor is it common for firms that focus on investing in the stock market to invest in early-stage or growth start-ups simultaneously. The skill sets are just so different. Also, for companies that invest mainly in public markets, it’s hard to invest in private companies when your investors have daily redemption rights. You might not be able to sell an illiquid position quickly enough to meet those redemption requests.

With that said, I think that being skilled in both areas is a huge advantage for an investor. Especially a technology investor. For example, understanding early-stage private companies can give them an edge in recognizing an amazing company before other public-market investors understand the company’s potential (think Amazon in the early 2000s through early 2010s). And vice versa, understanding how various public-market companies’ business models work and how public investors value them can help with pricing private deals and adding strategic value to the founder or management team.

I’m a fan of both; I think investors who can be proficient in both have a leg up on their competition. Personally, right now, I’m enjoying learning about and investing in public markets.

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