From Startup to 'Cashtag' Legend: Vlad Tenev & I Recount Robinhood’s Rise and The Future

Good afternoon…

Last week, I sat down with Vlad Tenev, co-founder and CEO of Robinhood ($HOOD ( ▲ 1.33% ) ) and winner of the Cashtag Legend Award at last week’s Stocktwits Cashtag Awards. We reflect on the remarkable journey from a startup idea to a $40 billion company reshaping investing. Vlad recounts Robinhood’s early days—pivoting from high-frequency trading software to mobile-first commission-free investing—and the challenges of fundraising and navigating regulation when no one wanted to back a brokerage startup.

We dive into pivotal moments: the explosive growth after Robinhood’s waitlist launch, the GameStop crisis, and steering the company through intense public scrutiny during the COVID era. Vlad opens up about the evolution of his role as CEO, from scrappy founder to leading a 3,000-person company, and shares why his passion remains rooted in building new products—from prediction markets to digital banking.

The most exciting and interesting takeaway for me as I think about Robinhood and the whole ‘degenerate economy’ around brokerage, wealth management, investing, trading, prediction markets and betting is Robinhood will not have to battle the brokerage incumbents like they did to get started. There is so much ‘open field’ (TAM - total addressable market) for them to grow into with their millions of customers.

JUMP TO THE GOOD STUFF:

• (0:00) The Birth of Robinhood: From Google Glasses to Innovation

• (6:58) Overcoming the Catch-22 of Raising Capital

• (9:33) Evolution and Growth of a Crypto Company

• (14:33) The Rise of Desktop Trading with Robinhood

• (19:19) Overcoming the COVID Era and Becoming a Legend

• (23:48) Evaluating Robinhood's Financial Offerings

• (25:06) Who Would Vlad Nominate For The Next Cashtag Legend Award?