Three best friends built an AI startup — and have a pact to drink one beer if it all collapses

When Ali Dastjerdi and Nathan Ondracek became freshman roommates at Harvard in 2015, they could hardly foresee the entrepreneurial journey that awaited them. Their bond grew stronger as they shared experiences in college, but it was a chance encounter with another friend, Samuel Ilkka, that would lead to the formation of their AI startup, Raylu. The trio, who now operate from New York, took a leap of faith in 2022, leaving their stable jobs to cofound Raylu, a company focused on developing AI agents designed to streamline sourcing work for private-market investors. Just recently, they announced an impressive $8 million in Series A funding, boosting their total raised capital to $12 million, with HighlandX leading the investment round. Their unique friendship serves as the backbone of Raylu's operations. Among their strategies to maintain camaraderie amidst the pressures of startup life is a single unopened beer stored in their office fridge. "The day the company collapses is the day we drink that beer," Ondracek remarked, emphasizing the importance of their friendship, regardless of their business outcomes. The three cofounders attribute their success to the deep trust they share. Having spent years together as friends, they navigate challenges with a sense of understanding that allows them to recover quickly from disagreements. Dastjerdi noted that their relationship resembles that of siblings, where temporary conflicts do not lead to lasting resentment. As they reflect on their journey, they acknowledge that the dynamics of their friendship have evolved since starting the company. Dastjerdi admitted the difficulty of switching between friend mode and cofounder mode, while Ilkka shared the importance of trusting his partners without micromanaging. The founders have learned valuable lessons along the way. Ondracek stressed the significance of having the right people within a startup, stating, "Nothing works if the people don't work." Dastjerdi advised aspiring founders to stay flexible and not cling too closely to initial ideas, while Ilkka cautioned against rushing into entrepreneurship just because others are doing it. For them, the true measure of success lies beyond the business — it’s about continuing to enjoy each other’s company, even in challenging times.