He sold his first startup for $100M. Then raised $250M in 18 months. | Dileep Thazhmon, Founder of Jeeves

Most second-time founders overthink their next move. Dileep Thazhmon did the opposite: he started eight different companies simultaneously to see which one would stick. The winner became Jeeves, a cross-border business banking platform that hit $7M ARR in just over a year and raised $250M in 18 months. His approach reveals why the most successful serial entrepreneurs treat early-stage company building like rapid prototyping, not careful planning.

Thazhmon's method sounds chaotic but follows a specific framework. "Eight different comp like, starting eight different companies. One was in the health space. One was, you know, in kind of, financial infrastructure," he explains. The selection criteria were deceptively simple: what can you contribute that's special, how big is the market, and is there a timing component pushing demand. COVID provided that timing component for Jeeves, accelerating the need for digital-first banking as Latin American companies expanded internationally.

This shotgun approach only works if you can execute across multiple domains simultaneously. Thazhmon calls it the "60% rule" , founders need to be 60% good at everything rather than exceptional at one thing. "Product was a great example. I I would be on every single call every day. We had two stand ups. Obviously, not good enough to scale it, but good enough to get it off the ground. I did the UX. I did the UI. I came up with the logo, the lion, like, you do everything and just keep it moving."

The 60% rule challenges conventional wisdom about founder-market fit and specialization. Most advice tells founders to focus on their core competency and hire for weaknesses. Thazhmon argues the opposite works better in the earliest stages. Being decent at design, product, sales, and operations lets you move faster than assembling a perfect team. The key insight is recognizing when 60% is enough to reach the next milestone versus when you need to upgrade to true expertise.

Jeeves succeeded because it solved a problem traditional banks wouldn't touch: cross-border payments for growing Latin American companies. "If you look at The US, it's a large single market with a single currency. If there wasn't competition, I would just do The US as well. It's much easier," Thazhmon notes. "But companies in Mexico that grow have to go to other countries to increase their TAM. Now they have the core problem, which is they have multiple cards, multi" currencies and complex banking relationships across borders.

This geographic constraint created the market opportunity. While US fintech companies could build massive businesses serving domestic customers, Latin American companies needed international solutions from day one. Traditional banks saw cross-border payments as compliance headaches. Jeeves saw them as the core product. The company now operates across 25 countries, turning regulatory complexity into competitive advantage.

Product-market fit at Jeeves evolved through multiple phases, contradicting the common narrative that PMF is a binary state you either have or don't. Thazhmon describes it as an iterative tightening process: "There's the initial PMF, then there's the okay. But now we need actually a growing business and then you start turning things off and so you're tightening the PMF." The initial fit was broad and loose. As the business scaled, they had to cut features and narrow focus to build sustainable unit economics.

This staged approach to PMF reflects a deeper truth about scaling fintech companies. Early growth often comes from saying yes to every customer need. Sustainable growth requires saying no to everything that doesn't drive core metrics. Thazhmon's willingness to "turn things off" after achieving initial product-market fit demonstrates the discipline required to build a venture-scale business rather than just a growing startup.

The Jeeves model suggests three actionable principles for founders in complex markets. First, test multiple ideas simultaneously rather than perfecting one concept in isolation. Second, prioritize broad competency over deep specialization in the earliest stages. Third, treat initial product-market fit as the beginning of the optimization process, not the end goal.

For founders building in international markets or regulated industries, Thazhmon's path offers a different playbook. Instead of avoiding complexity, embrace it as a moat. Instead of seeking perfect founder-market fit, develop the capability to be good enough at everything that matters. The companies that win in complex markets aren't necessarily the ones with the best initial idea , they're the ones that can execute across multiple dimensions while their competitors are still planning.