When Ali Dasjerdi and Nathan Ondrasek became freshman roommates at Harvard University in 2015, they never expected they would one day become co-founders together, or even launch a startup with a third friend they had never met.
Ondrasek met Samuel Ilkka at AWS, his first job out of college, and the two quickly hit it off and became roommates in Seattle. Dastjerdi, who worked remotely as an investor at Insight Partners during the pandemic, lived with the company for a year. Working and living together solidified the three-way friendship.
In 2022, the trio quit their jobs and co-founded Raylu, an AI startup building agents to help private market investors automate their procurement efforts. The company announced Monday that it has raised $8 million in Series A funding, bringing its total funding to $12 million.
HighlandX, one of our early customers, led the round. Dasjerdi said the VC firm used the product and liked it, but eventually asked how they could invest in it.
The Raylu team consists of 11 people and plans to expand to 20 by January.
Three 28-year-olds told me that Rail works because friendships work. One of the ways they protect their friendship is a bottle of unopened beer in the office refrigerator.
“The day a company goes out of business is the day we drink that beer,” Ondraczek said.
This is a reminder that their friendship is worth toasting, even if the company they built falls apart.
From roommates to founders
Ondráček and Dasjerdi met in the beginning of many college friendships. Harvard University assigned new students roommates through a 200-question survey, and the two ended up sharing a room. “From that point on, we really started getting along,” Ondraczek said. “Ali was the best man at my wedding.”
They took the same classes, computer science and statistics, and were roommates all four years. They spent late nights coming up with business ideas, but none of them took off. But the urge to build something together grew.
When Dasjerdi moved to Seattle with Ondráček and Ilkka, it was clear that this was a “once-in-a-lifetime opportunity to start a company with two close friends that I think are really great.”
“Some people start a company because of an idea. I think we started a company because there is a one in a million chance that this group will start a company,” Dasjerdi said.
The trio are currently based in New York, working out of WeWork’s offices, and do not currently live together.
benefits of deep friendship
Mixing friendship and business usually involves risk. But the three co-founders say they’re not afraid of duplication.
Dasjerdi said he sought advice from a mentor who once started a company with his childhood best friend. The instructor asked him a question. “If you and these two friends had the biggest fight ever, what would happen the next day?”
“I probably didn’t say anything,” Dasjerdi recalled. “We just got back to what we were doing,” Mentor said, which is a good sign.
The trio said there are benefits to working together as best friends. They trust each other, reset quickly after an argument, and know each other’s strengths and weaknesses.
“It’s a bit of a brotherhood,” Ondraczek said, explaining that the grievances do not lead to lasting hostility.
When we asked the trio to describe each other, their dynamic came into focus. Ilkka said Dasjerdi brought “urgency” and understanding to the investment community and called Ondraček “the best engineer” he knew. Dasjerdi described Ilka as the team’s optimist and risk-taker.
Rules for staying friends and staying sane
The co-founders said the dynamics have changed since they started their business together.
Dasjerdi said one of the most difficult adjustments for her was remembering how to be “constant friends” outside of work. Since “99%” of his thoughts revolve around the company, he’s had to build what he calls a “mental firewall” to keep co-founder mode from seeping into friend mode.
Trust has also become non-negotiable. For Ikka, he had to learn not to look over their shoulders when they were working. “I can stress about everything and trust that the people I work with can carry my weight,” he said.
They learned to celebrate victories more intentionally. Especially since we celebrate them not just as founders, but as friends.
“You have to celebrate the good things because no one is going to celebrate the good things for you,” Ondraczek said.
Thoughts as a founder
The founders say that through their journey, they have learned some valuable lessons worth sharing.
Ondráček said that the most important thing for a startup is its people.
“If people don’t work, nothing works,” Ondraczek said. “You can adapt your product to the best possible market, but if your people aren’t working, you’re doomed from the start,” he added.
Dasjerdi said founders shouldn’t get carried away with an idea too quickly.
“We went through it over and over again and felt like someone liked what we did,” he said. “When we actually found product-market fit, it was definitely different. It’s like people have to strip you of the product.”
He added that continuing to iterate, be selective, and make more pivots can sometimes lead to bigger wins.
Iruka cautioned against rushing to become a founder just because others started young. The right time, he said, is when you are ready and have a real purpose for making the decision.
What if you’re building with your best friend? Make sure you still want to grab a beer together even when things go awry.
Do you have a story to share about building an AI startup? Contact this reporter at: cmlee@insider.com Or send a signal at @cmlee.81.
