Despite a previous successful exit, Dileep Thazhmon took Jeeves through Y Combinator not for basic education, but for brand credibility in new international markets, access to fintech expertise, and as a hedge against COVID-era uncertainty.

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YC provides a built-in go-to-market engine where startups treat their 200+ well-funded batchmates as their first customers. This 'win YC, win the market' strategy de-risks early customer acquisition and provides critical initial revenue and case studies to build momentum.

Beyond tactics and networking, YC's greatest value is psychological. Constant exposure to hyper-successful founders and casual conversations about billion-dollar outcomes normalizes massive success, fundamentally expanding a founder's own definition of what is possible and instilling greater ambition.

Second-time founders (“Act II teams”) possess a unique advantage. They can solve the same core problem but with complete clarity from the start, knowing the edge cases and organizational structure required. This allows them to leverage modern technology while avoiding the mistakes of their first venture, as seen with the founders of Workday and Affirm.

Having no prior banking experience helped Jeeves' founder. He wasn't "coded in a certain way" by industry dogma, allowing him to envision a global-first infrastructure that insiders would have dismissed as too complex. This outsider perspective was a key advantage.

YC's program for students isn't just about flexibility; it's a strategy to track promising founders for years. By encouraging repeat applications, YC gathers longitudinal data on a founder's evolution, thinking, and progress, de-risking the eventual investment by observing their entire pre-founding journey.

Duolingo's first investors admitted they didn't believe in the education market, which they considered a bad business. They invested solely because founder Luis von Ahn had a previous successful exit to Google, demonstrating that a founder's track record can be more persuasive to early VCs than the business idea itself.

Contrary to the "clean cap table" advice, Jeeves's founder intentionally raised from many small investors in his seed round. He wanted a large network of people invested in the company's outcome to call upon for help with expansion into 25 different countries.

It's easy for founders to feel they've "arrived" after getting into Y Combinator. The PointOne founders consciously avoided this, viewing it as a rational bet by YC, not a signal of success. This sober mindset kept them focused on the immense challenges that still lay ahead.

Even startups with traction and pre-seed funding find Y Combinator transformative. YC partners provide unparalleled, stage-specific feedback that founders can't easily get elsewhere, making the 7% equity cost worthwhile for companies well beyond the idea stage.

Beyond the network and money, a key YC benefit is the profound psychological impact of having respected partners who genuinely believe in your mission. For a lonely early-stage founder, this support transforms the journey from a solitary struggle into feeling like they're "playing for the home team," which raises the stakes and boosts motivation.