
In this episode, Lex chats with Yoshi Yokokawa, CEO of Alpaca — a brokerage infrastructure company that provides API-based trading and custody services to fintechs and developers globally.
The conversation begins with their shared experience at Lehman Brothers during the 2008 financial crisis, where Yoshi worked in fixed income securitization and learned that even when market participants sense a bubble, they keep dancing because timing the exit is impossible. After Lehman's collapse, Yoshi pursued entrepreneurship, building a computer vision AI company acquired by Kyocera before founding Alpaca in 2017. Initially inspired by Robinhood, Yoshi pivoted after experiencing firsthand the friction of accessing brokerage infrastructure—realizing the deeper opportunity was building API-first brokerage rails for developers. Today Alpaca powers 9 million accounts through 300+ partners across 45 countries, recently raising $150 million at a unicorn valuation.
The discussion explores how Alpaca follows Robinhood's product roadmap to anticipate partner demand, the challenges of adding crypto, and Yoshi's thesis that finance is undergoing a generational shift from digital to on-chain operations. Lex shares examples of legacy infrastructure dysfunction—from faxing PDFs to TD Ameritrade in 2012 to the Synapse collapse caused by manual CSV uploads—illustrating why Alpaca built its own custody and ledger systems as a path to competing in the $350 trillion global securities custody market.
NOTABLE DISCUSSION POINTS:
TOPICS
Alpaca, Lehman Brothers, Barclays, Nomura, Neuberger Berman, Blackrock, Robinhood, Interactive Brokers, TD Ameritrade, BNY Mellon, Brokerage infrastructure, API, trading, tokenization, embedded finance, fintech, crypto, web3
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