When Ali Dastjerdi and Nathan Ondracek became freshman roommates at Harvard in 2015, they didn’t expect they’d one day be cofounders together — or that they’d build a startup with a third friend they hadn’t met yet.
Ondracek met Samuel Ilkka at AWS — his first job out of college — and the two bonded quickly and became roommates in Seattle. During the pandemic, Dastjerdi, who was working remotely as an investor at Insight Partners, moved in with them for a year. Working and living together cemented the three-way friendship.
In 2022, the trio quit their jobs to cofound Raylu, an AI startup that builds agents to help private-market investors automate sourcing work. On Monday, the company announced that it had raised $8 million in Series A funding, bringing its total funding to $12 million.
One of their earliest customers, HighlandX, led the round. The VC firm used the product, loved it, and eventually asked how they could invest, Dastjerdi said.
The Raylu team consists of 11 people, with plans to expand to 20 by January.
The three 28-year-olds told me that Raylu works because the friendship works. One of the ways they protect their friendship: a single, unopened beer in their office refrigerator.
“The day the company collapses is the day we drink that beer,” Ondracek said.
It’s a reminder that even if the company they built falls apart, their friendship is still worth toasting.
From roommates to founders
Ondracek and Dastjerdi met the way many college friendships begin. Harvard assigns freshman roommates after a 200-question survey, and the two ended up in the same room. “From that point forward, we started becoming really close,” Ondracek said. “Ali was the best man at my wedding.”
They took the same classes — computer science and statistics — and stayed roommates for all four years. They spent late nights dreaming up business ideas, none of which stuck. But the urge to build something together did.
When Dastjerdi moved to Seattle with Ondracek and Ilkka, it was obvious to him that this was “a once-in-a-lifetime opportunity to build a company with two close friends that you think are truly brilliant.”
“Some people start companies because of ideas. I think we started a company because it’s a one in a million shot to have this group to be able to start it with,” Dastjerdi said.
The trio, now based in New York, works out of a WeWork office, and no longer lives together.
The perks of deep friendship
Mixing friendship and business usually comes with risks. But the three cofounders said the overlap didn’t scare them.
Dastjerdi said he sought advice from a mentor who’d once started a company with his childhood best friend. The mentor asked him one question: “If you and these two friends had just the biggest fight ever, what would happen the next day?
“I said probably nothing,” Dastjerdi recalled. “We would just get back to doing what we were doing.” The mentor said that was a good sign.
The trio said working together as best friends has upsides: They trust one another, reset fast after an argument, and know each other’s strengths and weaknesses.
“It’s like a little bit of a sibling relationship,” Ondracek said, explaining that disgruntlement doesn’t lead to lasting animosity.
When I asked the trio to describe one another, their dynamic snapped into focus. Ilkka said Dastjerdi brings “urgency” and an understanding of the investing world, and he called Ondracek the “best engineer” he knows. Dastjerdi described Ilkka as the team’s optimist and risk taker.
The rules of staying friends — and staying sane
The cofounders said their dynamic has changed after starting a business together.
Dastjerdi said one of the hardest adjustments for him was remembering how to be a “regular friend” outside work. Because “99%” of his thoughts revolve around the company, he’s had to build what he calls a “mental firewall” to keep cofounder mode from bleeding into friend mode.
Trust has also become non-negotiable. For Ikka, he has had to learn not to look over their shoulders as much when they’re working. “I can either stress about everything, or I can trust these guys I’m working with to handle their weight,” he said.
They’ve learned to celebrate wins more deliberately — especially because they’re doing this not just as founders, but as friends.
“You have to celebrate the good things because no one’s going to celebrate them for you,” Ondracek said.
Reflections on being a founder
The founders say their journey has taught them a few valuable lessons worth sharing.
Ondracek said what matters most for a startup is its people.
“Nothing works if the people don’t work,” Ondracek said. “You can have the most product market fit, and if the people don’t work, you’re doomed from the start,” he added.
Dastjerdi said founders shouldn’t fall in love with an idea too early.
“We went through many iterations where it felt like someone kind of liked what we did,” he said. “When we actually found product-market-fit, it is so tangibly different. It’s like, people have to rip the product from you.”
Keep iterating, be picky, and pivot more — sometimes that could lead to a bigger win, he added.
Ilkka warned against rushing into the founder path just because other people are starting young. The right time is when you’re ready, and when there’s a real purpose driving the decision, he said.
And if you’re building with your best friends? Make sure you still want to open a beer together when everything goes south.
Do you have a story to share about building an AI startup? Contact this reporter at [email protected] or Signal at @cmlee.81.
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