Sam Parr and a guest discuss why entrepreneurs struggle with job applications at startups like Stripe and Uber. They explore the opportunity cost of missing early equity: one rejected Vungle offer later sold for $800 million. The conversation covers what to prioritize in a job today, from good managers to sectors like biotech, and why you should apply to companies you'd want to invest in.
And by the way, when you— so have you had a job? Have you been employed? Let's say not like kind of like college age, but like since then, or have you just done businesses of your own?
Uh, we had like an acquisition and I was kind of employed there, but I—
but you haven't gone and just interviewed for jobs?
I interviewed once, uh, a couple times and I never got them.
What'd you interview for?
For Vungle, for Jack Smith, my best friend. I interviewed for his job and I didn't get it.
What happened?
They just didn't call me back. I started—
they didn't call you back? Jack didn't tell you?
The guy who's like my best friend now, I didn't know him I interviewed at his job.
Oh, you didn't know him at the time?
I didn't know him.
Okay.
They interviewed me and they didn't hire me. And then 2 years later we became best friends.
And you were trying to be a salesperson or what?
I don't even remember. I think so.
Um, by the way, I have a similar story. I, uh, applied to Stripe. I think I might have told this story already, so apologies if I did. But, uh, 2012 I applied to, uh, I was gonna apply for a job for the first time in my life. I had started 2 companies before that. I was like, I'm moving to Silicon Valley. I'm gonna get a job. I'm gonna learn from other people. Rather than start my own thing. And, um, I only applied to 2 jobs. One was Stripe, and I got to the phone screen. Um, and I, I really had it made because the guy who was interviewing me, his mentor in life was one of my former advisors in my startup and had written a blog post being like, this guy Sean is like, he said it specifically, he has the highest bias for action of any entrepreneur I've ever met. He made a warm intro to this guy and was like, trust me, this guy's legit, you should hire this kid.
How the fuck did you not get that job?
And so I thought I was cruising too, and maybe that's why I didn't get it. But I get to the part of the interview where he was like, all right, you know, this job has a lot of sort of sales and persuasion stuff. Um, so, you know, we're a piece of software, so I want you to, you know, we're gonna do a little role play. You're gonna sell me a piece of software. And he's like, you can pick any software you like, whatever you're familiar with.
Oh, you probably got creative or something.
And I was just like, um, I was like, okay, so I, here's what I would do. I would talk to you about this. He said, no, no, no, don't tell me what you would do. Like, I'm the customer. Hello, I just picked up the phone. Go. And I was like, fuck. And so I, I was like, hey, uh, you know, I'm telling you about, I picked Basecamp, uh, as my software. Big mistake. Cause I don't even know Basecamp very well. And so I just like pulled, I just took it.
So they didn't call you back for that reason?
By the, by the end of that role play, He was just like, yeah, I don't think this is for you. I'm just being honest with you. Like, I just don't think you're, you know, a good fit for this.
That was 8 years ago.
So yeah, I was like probably 22, 23 or 24 at the time.
How— fuck, how early?
But I'm like, I blew it. Like, it wasn't their bad. Like, I definitely blew that interview.
How early of an employee would you have been?
So I think they were at like 50, maybe 50 people or less or 100 people or less.
It cost you $5 million. Well, yeah, I don't know how much equity I would have.
I would have had to do the rocket ship thing. I would have had to start in a crappy seat, crush it, and then get into a good seat to get equity.
But like, I did that with Uber and Airbnb. I had job interviews at Airbnb and Uber early-ish, first 100 people. And one of them I got employed, one of them I got the offer, but then they rescinded it because I lied about my resume. And the other one I didn't get past the final.
What did you lie about?
I had a criminal record and I told them I didn't. Okay, so I moved all the way out here.
Called my bluff. Fair play.
I moved all the way out here and they're like, oh, All right. Don't come to work on Monday.
Dude, that's hilarious. At least you had good eye for picking these companies.
And then I applied at Vungle and they sold for $800 million. So I always tell people, find out where I want to work at, who will also deny me, and then invest there.
Okay, let's start with where would you want to work at today if you were you back then? Where would you be applying today?
Great question. Do you have an answer?
You want to go for a couple of years ago? I answered this. I was like, the only place I would be really interested working was AngelList at the time.
No, that'd be horrible place to work.
And so I thought AngelList was doing really interesting shit, and I think it's gonna be big, and it did end up becoming big. And this was like 7 years ago, so it was a while ago.
Yeah, no, that would be a horrible place to work though, because that Naval guy is fucking crazy.
Really? I love Naval.
Well, I don't know, but he seems like a brilliant genius, so a great person to listen to, but a horrible person to manage you.
If—
okay, if I had to work somewhere, I probably Hmm, probably just somewhere with really good managers. Um, most startups have horrible managers and it means—
but like when you were looking at Uber, Airbnb, you didn't know the managers, so you weren't using that criteria then.
No, but the— and I don't know if it would've been successful. Sarah, my wife, works at Airbnb and she loves her managers. And you know how everyone's like, so what are you gonna do next? They always say that. And she's like, what do you mean? Why would I ever do anything next? This is awesome. I'll be here for a really long time.
Right.
And, uh, I would love to have that feeling.
I would probably now look for a company that's— I would go find all the most interesting, uh, biotech-based companies. So anybody doing something with genetics, genomics modification, anything like that. I think that's a big wave that's coming. I'd go try to be early there. Self-driving cars. If there's someone who's awesome there, I would do something in that. If—
or, um, it's hard though.
It's really hard to—
if I wanted to make a lot of money, let's say I wanted to like be like, all right, I'm gonna try and save hundreds of thousands of dollars in the next 3 years of work.
Just go work at Facebook or what?
Facebook, Google, or an enterprise sales role at a super boring B2B, uh, uh, enterprise software company, right? Where the, where the average deal is like $300,000 or $400,000 a year.
Right.
That's what I would do.
So, so if I took my own advice, I would look for who's a rocket ship. So I would try to maybe like Lambda School, I think is interesting. Um, I would just basically try to go find who's the fastest growing startup right now that's at maybe 50 people or 20 people or 10 people, whatever they are. I would go try to find them and then I would be like, hey, I'll come solve any problem you got. Like, we'll figure it out.
I went to the Substack office the other day. They just raised $16 million in funding. You know how many employees they have? 5.
5.
I would— that would be an interesting place to work.
