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.
Early-stage founders don't need to be experts. Dileep Thazhmon handled UX, UI, and logo design himself. The goal is to be just good enough across all functions to maintain momentum and reach the next stage, not to achieve perfection.
To survive the startup grind, founders must be intrinsically motivated by the problem they are solving. Jeeves founder Dileep Thazhmon explored eight different ideas for a year, discarding those where he wasn't passionate about the core challenge, even if they were good business opportunities.
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.
When their card provider shut them down, Jeeves faced a 60-day gap with no product. To survive, they launched a credit-based payment product managed on a spreadsheet. This crisis-born MVP now accounts for 40% of the company's revenue.
To test its core hypothesis without building costly local infrastructure, Jeeves shipped standard US corporate cards internationally and absorbed the 2% foreign exchange fees. This unprofitable, unscalable MVP quickly proved strong demand for their cross-border product.
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.
The Jeeves founder strategically includes potential leads for his next funding round in his current round, even for a small check. This gives them an insider's view of the company's progress, building trust and making it easier to secure their lead investment in the subsequent round.
Dileep Thazhmon left his >$50M revenue company because he "wasn't learning at the velocity" he wanted. He advises that your time is your most valuable asset and you should optimize for learning speed over staying in a comfortable, stagnant role.
A founder can only excel at one function at a time. In the beginning, it's product. Once that's solid, the focus must shift entirely to go-to-market and founder-led sales. Later, it may become finance. This is a conscious trade-off and sequential juggling act.
Product-Market Fit isn't just any hockey-stick growth. The founder of Jeeves defines it as the moment your target customers—the ones you want to grow with long-term—start coming to you organically. Early growth from non-ideal customers can be a false positive.