This Week in Startups How Robinhood became a $68B company w/ Vlad Tenev
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Mar 18, 2026 
Vlad Tenev, Robinhood co-founder and CEO, joins for a sharp look at how a fintech giant scaled fast. He gets into free trading as a growth engine. He talks about relaunching products again and again. There’s also startup survival through bad press, hiring and design taste, and how AI could reshape products, support, and competition.
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Jason Backed Robinhood When The Pitch Sounded Absurd
- Jason Calacanis invested after Vlad Tenev said Robinhood would offer free stock trading to millennials, despite sounding like zero TAM and zero revenue.
- Jason backed the idea because if it worked, a whole generation would grow up on the app.
Free Trading Expanded The Business Instead Of Shrinking It
- Robinhood proved that winning users first can create a much bigger business than optimizing the first revenue line.
- Vlad Tenev said free trading led to 11 business lines over $100M each by removing the visible $10 commission and keeping smaller market-structure revenue.
Launch Missing Features Like New Products
- Robinhood turned a missing table-stakes feature into a launch event instead of quietly patching it.
- Robinhood Instant solved the three-day settlement wait and let users trade within minutes, then the team relaunched again when the waitlist came off.