Howard Lindzon does something most venture capitalists would never do: he tells his limited partners, upfront, that most of his bets will fail. The StockTwits CEO and Social Capital founder describes his seed fund using a metaphor he borrowed from a Larry David sensibility.
“You are betting on me to hang 30 pieces of art in Howie’s gallery, the Larry David gallery. And you will pick the 2 that went to zero,” Lindzon said on Barry Ritholtz’s Masters in Business podcast. His goal is one company that turns into a “100-bagger.”
The Power Law Underneath the Confidence
Seed investing is governed by a power law: a handful of winners pay for everything. Lindzon admits the discomfort. “Our job is to find a Robinhood. And we found many of them, you know, LifeLock, Robinhood, Beehive,” he said. He recently invested in Alpaca, which “powers 1,000 Robinhoods around the world.” You can hear the full conversation on Bloomberg’s Masters in Business.
The release valve, he said, is integrity: “The integrity of telling my investors that upfront is the release.” I have followed Lindzon’s writing for over a decade, and this is the through-line: tell people what you are actually doing, then go do it.
Why Robinhood Still Matters to the Thesis
Robinhood (NASDAQ:HOOD | HOOD Price Prediction) is the canonical Lindzon win, and the company keeps illustrating his power-law point in public form. Shares are down 32% year to date to $76.55, after Q1 revenue of $1.067 billion missed the $1.135 billion consensus and crypto revenue collapsed 47% to $134 million. Yet event contracts rose 320% year over year, and the Gold subscriber base hit 4.3 million. One product line dies, another compounds.
The Public Market Echo
The seed dynamic repeats across the brokerage stack. Coinbase (NASDAQ:COIN) just printed a $1.49 per share GAAP net loss and announced a 14% headcount cut, while Interactive Brokers (NASDAQ:IBKR) is up 69% over the past year with customer accounts growing 31%. Charles Schwab (NYSE:SCHW) closed its Forge Global acquisition in March 2026, pushing retail into private markets, the same lane Robinhood is targeting with its Ventures Fund I. Different paths, same power-law math.
The Takeaway for Retail
Lindzon’s advice for everyone else is refreshingly unsexy. “I think most people should index, but everybody should learn how to pick stocks too in this era,” he said, pointing to AI tools that make every investor sharper. “Everyone’s a CFA all of a sudden” with Claude in their pocket.
You would want to own a basket of brokers if you believe retail participation keeps compounding. The inverse holds if you think the current cycle exhausts itself. Either way, Lindzon’s gallery metaphor stands: hang 30 paintings, expect two to be ridiculed, and hunt relentlessly for the one that funds the rest.
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