How Robinhood became a $68B company w/ Vlad Tenev
This Week in Startups
Jason Calacanis
4.2 • 1.4K Ratings
🗓️ 18 March 2026
⏱️ 50 minutes
🧾️ Download transcript
Summary
This Week In Startups is made possible by:
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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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Transcript
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| 0:00.0 | I was a founder my whole life and I always dreamed, gosh, I wish I could go to this demo conference or this PC forum. |
| 0:08.0 | But they were even back then in the 90s and early 2000s, $4,000, $6,000 a ticket. |
| 0:15.0 | And back then they charged you to show your startup on stage, $20,000. |
| 0:19.0 | Yeah, I was like, well, that's some real bullshit. |
| 0:23.5 | I can't even afford the ticket. |
| 0:25.8 | So I used to do something called lobby crashing. |
| 0:28.1 | And I would find out where these fancy conferences were. |
| 0:32.1 | And I would buy the cheapest ticket possible, |
| 0:34.9 | going through two or three cities, |
| 0:36.2 | get the cheapest hotel possible before Airbnb. |
| 0:38.7 | And I would just hang out in the lobby with my laptop and hope to meet famous entrepreneurs, |
| 0:43.3 | Bill Gates, Steve Jobs. |
| 0:45.0 | And I did actually do that, Michael Dell. |
| 0:47.1 | I would see them in the lobby. |
| 0:50.7 | This weekend startups is brought to you by Eru, Unify Yourify your identity, endpoint security, and compliance into a single platform. |
| 0:58.9 | Twist listeners get 20% off when they book a demo at iru.com slash twist. |
| 1:04.4 | LinkedIn jobs. Higher right the first time. Post your job and get $100 off towards your job post at LinkedIn.com slash twist and deal. Founders |
| 1:14.9 | ship faster on deal. Set up payroll for any country in minutes and get back to building. Visit |
| 1:21.0 | deal.com slash twist to learn more. |
| 1:26.2 | A guy named Tim O'Reilly, who had a company called O'Reilly Publishing. Anybody read those books still? Because he know what I talk about, yeah. And he saw me at one of his conferences, and he's like, you're lobby crashing again. I was like, yeah, I hope I'm not in trouble. He's like, I, here, and he just took out a pass and he handed it to me and I was like no no Tim I don't have the money for it |
| 1:48.0 | he said just don't tell anybody he gave you a free ticket and I was like wow this is incredible act of kindness |
| 1:53.7 | and I never forgot it because then I was in I was in the room where it happened I said you know if I ever make it |
... |
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