Sheel Mohnot: Lessons from Investing in Flexport and Missing on Robinhood | 20VC #917

(beeping) Three, two, one, zero. You have now arrived at your destination. Sheel, I am excited for this. I have heard so many good things, from, uh, snacking options that you love, to jumping over pools. This is gonna be a unique interview, so thank you so much for joining me today. (laughs)

Thank you for having me. And yeah, I've been, I've been a listener for so many years. Uh, super excited to be on the show.

That is a very kind way of saying of my aging, but, uh, I would love to start today-

(laughs)

... with, uh, a little bit-

Well, you still can when you're 18, so. (laughs)

This is true, I'm actually-

But, um-

... Benjamin Muffin in disguise. Um, but, uh-

(laughs) Exactly.

... I wanna start with a little bit of your context. How did you make your way into the world of venture, and then how did you come to found Better Tomorrow most recently?

Yeah. So, I made my way into venture, uh, I think probably a not unusual path. I was a founder. I, um, first joined on with a friend to start a company, uh, now in 2010, and then that company got acquired in 2012. Ended up starting a company, uh, shortly afterwards. That company got acquired in 2015. And at that point, 500 Startups, who had invested in the first company, asked me, uh, to join them. And originally, I was just joining them as a mentor, and then I found that I loved it. I think, you know, I loved helping founders at the earlier stages, and thought, "Hey, maybe I could make my career doing this." And that's sort of evolved into what it is today. So at 500 Startups, I started a fund, 500 Fintech, and then, um, over the course of a couple of years, I started interviewing at other funds, uh, and I was interviewing alongside this guy Jake Gibson, who was a friend of mine. He had started NerdWallet. I knew him well. He became an EIR of mine at 500 Fintech, and we're both interviewing at other funds. Things are going well, but we're talking to each other on the phone all the time, like, "How did your interview go? What did they ask you? What was difficult? What's the next step?" And so we kinda just became, like, really close during this time. And it's, to some people, it could've been a rivalry, like we were probably competing for the same jobs. Like, there's only gonna be one GP that specializes in fintech at a tier one fund. But we took it as a friendly thing, more than anything else. And any time a fund was interviewing one of us, we'd say, "Oh, hey, have you considered Jake? Have you considered Sheel?" And so we ended up getting offers at- at funds, but decided, during this time that he and I got to know each other a lot better, we decided, "Hey, maybe we should just do our own thing. These funds are maybe not for us. Some of them are too bureaucratic, some of them have different personalities than we like. Let's just do our own thing." So that was, uh, towards the end of 2019, and we haven't looked back. It's been amazing.