Three co-founders on what makes a strong team and chasing their entrepreneurial dreams together

Before they even moved into their dorm room at the University of Pennsylvania, Nick Fleisher and Liam Germain conspired to co-found a company. “When we got to Penn the first day, we basically said we are going to drop out,” Fleisher told Founder Brew. “We made a pact that was: Our goal is to build a business so great that we’re able to both just drop out and not go back to school.”

Fleisher and Germain’s pact to drop out didn’t happen—both roommates ended up getting their undergraduate degrees from the school—but their entrepreneurial ambitions stayed. They dabbled in building projects together, and Fleisher got a day job as a consultant at McKinsey.

At McKinsey, Fleisher met Jarryd Strydom, a former lawyer turned consultant with a penchant for startups. The two hit it off. “Jarryd and I were already coding every day after McKinsey,” Fleisher told Founder Brew. “It wasn’t like, ‘Hey, let’s start using our free time to build stuff.’ We were already building a bunch.”

Fleisher connected Germain and Strydom, and the three decided to build a company to smooth out intake processes for legal issues. Sandstone, an AI platform for legal teams, launched earlier this year.

Now, the trio navigate the realities of entrepreneurship, like the trust needed to build a successful product or hiring experts whose careers began before they were born.

“That’s just a weird reality that you don’t really prepare for,” Fleisher said.

This interview has been edited for length and clarity.

As a team of founders, how did you learn to trust each other?

Fleisher: The nice thing for us was that we all had some dynamics before. Jarryd and I worked together on things at McKinsey. Liam and I have started businesses together before. Liam and I had two co-founders break up with us in one of our last startups. We’ve been through a lot. These two didn’t know each other, but I like to think I was some weird middle ground that helped them become comfortable with each other. Ironically, they now maybe spend more time with each other than I spend with both of them.

Some people think strangers make better co-founders. How do you respond?

Has there been a day you’re thankful you were already friends?

Fleisher: One of the nice things with having co-founders who know you very well personally is that they can call you out on flaws and push you to do better…One of our first big Fortune 500 demos, I remember calling Jarryd before and being like, “We can’t do this demo. We’re so not ready.” I’m very hyper as a person. I’m like, “You need to be perfect to nail this.” Jarryd is super calm, and he knows that I am very intense, but he’s very good at just calming me down. He wouldn’t know that if we hadn’t spent time socially together to understand my personality.

Germain: It’s very nice that if there’s something going on in my life or anyone’s life here, that we trust one another enough that it’s no big deal. We’ll cover for that person.

Strydom: My whole family’s in South Africa, my whole life is basically in South Africa. One week I messaged Nick with one hour’s notice, saying, “Dude, I actually have to go to South Africa for a week. I’m dealing with something personal.” He’s like, “Cool, no worries.” That’s a good example of being able to just adapt and cover for each other, which is big in the space when every day counts.

How early did you know you wanted to start a company?

Fleisher: In middle school, I had all these fake businesses. I got all my friends together and we’re like, “We’re going to start a hedge fund.” I think that’s always been a thing. Liam and I, we met before we started at Penn because we found each other on Facebook. There was like a Facebook match group, and when we got to Penn the first day, we basically said, “We are going to drop out.” We made a pact that our goal is to build a business so great that we’re able to both just drop out and not not go back to school.

Germain: My first farmer’s market stand was at eight years old.

Did you say a middle school hedge fund?

Fleisher: You could do these mock investing accounts…We took all this mock money and we would compete against each other. I remember being on the schoolyard. It was totally ridiculous.

What was so exciting about the idea of founding a company?

Fleisher: I wanted to see people use something that I had built…The random interaction that you have with someone where you see them using your product or I saw a general counsel wearing a Sandstone hat the other day on the street, those types of things I think are what excite me.

Germain: Always the idea of controlling your own destiny in a way…If you’re going to spend all of your life working on something, I would really like it to be something that I love to do.

What’s the biggest surprise then about actually running a company?

Fleisher: People management…It’s this moment where you’re in an office with 40 people, things are completely different. You want to be able to still move super quickly, but it’s not just about your product anymore.

Germain: Now the goal is: How can we build a team that is so much better at all the things that we think we’re good at? It’s a very weird mental switch from: “Oh, this was something I was really good at, and I got everyone else to be excited about it.” Now the goal is: “I need to go find people that are 10 times better at it than me.”

Fleisher: We had someone accept an offer who started engineering at a top company before we were born. We looked at each other after the dinner, and we were like, “What the fuck are we doing?” This guy knows so much more, but now it’s at that point where everyone in the room should be better at the things that they do every day than I am in any one thing. That’s just a weird reality that you don’t really prepare for.