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

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

This Week in Startups

March 18, 2026

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Speakers: Jason Calacanis, Vlad Tenev
**Jason Calacanis** (0:00)
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. But they were, even back then in the 90s and early 2000s, four, five, $6,000 a ticket. And back then, they charged you to show your startup on stage. $20,000, yeah. I was like, well, that's some real bullshit.

**SPEAKER_2** (0:23)
I can't even afford the ticket. So I used to do something called lobby crashing.

**Jason Calacanis** (0:28)
And I would find out where these fancy conferences were. And I would buy the cheapest ticket possible, go in through two or three cities, get the cheapest hotel possible before Airbnb. And I would just hang out in the lobby with my laptop and hope to meet famous entrepreneurs, Bill Gates, Steve Jobs. And I did actually do that, Michael Dell. I would see them in the lobby.

**SPEAKER_3** (0:51)
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**Jason Calacanis** (1:26)
A guy named Tim O'Reilly, who had a company called O'Reilly Publishing. Anybody read those books still? I guess you know what I'm talking about. Yeah. And he saw me at one of his conferences and he's like, your lobby crashing again. I was like, yeah, I hope I'm not in trouble. He's like, 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. He said, just don't tell anybody I gave you a free ticket. And I was like, wow, this is incredible act of kindness. 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, I'm going to make a conference where all the founders come for free and they don't have to pay to be on stage. And I'll just pay for it myself or get some sponsors or something. Well, that's what Launch Festival is.
And I couldn't do it without Backblaze and Render, two of our great sponsors, and I'll thank them a bunch of times. And also Jetro, who's helping me launch Founder University in Japan. Mercury, Goodwin, Every, Backblaze, PayPal, Render. These are all just great companies that'll help me rent spaces like this, get the AV and maybe put out a little coffee. We try to keep it gritty. It's not pretty, but it's gritty, right? That's what I like to do at these events. Keep it gritty, keep it real. Everybody, who in the room is an active founder right now? Raise your hand nice and high. Take a look around. It's everybody. You're amongst friends. This is like Professor X's mutant academy.
That's what I always say, founders like mutants. When I started my angel investing career, I would just walk around and was hanging out one night at Antonio's Nut House, which was a bar, really the most disgusting dive bar you've ever seen in Palo Alto. It's shut down now, probably for health code violations. Really tall, good-looking guy came up to me and said, you're Jason? Yeah. I said, yeah. He said, I want to tell you about the company I'm building. We're going to help people trade stocks. I said, what kind of people? He said, millennials. I said, the ones who don't have drivers licenses and are on their mom's Netflix accounts. He said, yeah. Those people. I was like, okay. How do you make money? He goes, oh, it's the best part. We're going to make it free. I said, free to trade and millennials. So your TAM is zero and your revenue model is zero.

**SPEAKER_2** (3:57)
He said, gee, Jason, when you say it like that, I feel kind of dumb.

**Jason Calacanis** (4:01)
I said, I'm in.

**SPEAKER_2** (4:02)
He said, can I ask you why you're in?

**Jason Calacanis** (4:04)
I said, what if it works? You'll have a whole generation will grow up on this amazing app. And this is when the iPhone had recently come out. And now he's known by one name, Vlad from Robinhood.
Whenever I ask Vlad to come talk to founders, he says yes, which he's very busy, he's running a giant company. But just reminiscing there about the early days, you went to investors, and you had to sell them on zero tan. When they said to you, hey, Vlad, what company are you disrupting, and how much money are these people spending already on this service so they can get an idea? What was the objection, and how did you deal with that objection?

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