How Robinhood became a $68B company w/ Vlad Tenev

How Robinhood became a $68B company w/ Vlad Tenev

Author: Jason Calacanis March 18, 2026 Duration: 49:41
This Week in Startups
Technology

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Today’s show:


We’ve got a treat for you today on TWiST! Jason is live from LAUNCH Fest in San Francisco, where he’s joined by Robinhood founder Vlad Tenev.

The era of AI is here. Robinhood found success in the midst of the last great technological shift. What lessons did Vlad take from this, and how can founders apply these to this next transformative period? What elements are the same and what elements have changed?

Let’s get inside the mind of one of the greatest founders of the last decade!

Timestamps:

0:00 Why Jason runs events like LAUNCH Fest.

3:25 The early days of Jason and Vlad.

5:54 Why getting users before monetizing creates a bigger business.

9:49 Deel - Founders ship faster on Deel. Set up payroll for any country in minutes and get back to building. Visit https://deel.com/twist to learn more.

11:03 Finding ways to launch a product multiple times.

13:49 How Robinhood identified its initial customers.

20:09 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist.

21:04 Robinhood's "give to get" and waitlist mechanics explained.

25:07 Navigating mistakes that feel existential (they're not!)

27:36 Leaning into negative press.

30:30 Iru - Iru unifies identity, endpoint security, and compliance into one platform. TWiST listeners get 20% off when they book a demo at https://iru.com/twist

32:13 Tackling competition in the AI era.

37:20 How Vlad hires and develops talent.

42:16 What is good design in an era of vibe coded slop?

46:46 Vlad's top lessons from the last 10 years.


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Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
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