Why do successful people secretly fear losing?
I asked Phani Sama, Founder of RedBus, this question on my podcast and his answer has stayed with me all week.
Growing up in Telangana, moving to Hyderabad, stacking win after academic win, Phani built what he calls a "virtue cycle of winning." Every success fed his confidence, which fed the next success. It's the same cycle that eventually took him to BITS Pilani, into a bus-ticketing idea born out of pure frustration, and to a company that sold for 600+ crores.
But here's the part founders don't usually admit out loud:
"I realized that virtuous cycle of winning, that habit of winning, is a shackle. You don't want to get out of it. You fear losing. Even in an argument, right if you and I are talking, I don't want to lose."
The same habit that builds you becomes the habit that cages you. You stop admitting you're wrong. You stop changing your mind. You start protecting the streak instead of chasing the truth.
RedBus itself was born from exactly the kind of humility that habit tries to kill — Phani missed a bus on Diwali 2005, realized the "no seats" problem was really a "no visibility" problem, and instead of forcing bus operators to adopt his software, he simply asked them what they wanted. They said: sell more seats. So that's what RedBus did — two seats at a time, until they were managing half a bus.
Post-exit, he's built a very different kind of scoreboard: Kakati Sandbox, a nonprofit that's skilled rural youth to a 90%+ job placement rate on a 5-acre campus. And he's had to relearn, deliberately, how to lose, journaling his conversations, consciously letting arguments go, catching himself before he defends a position just to stay undefeated.
What made him is also what could have stopped him. That's the whole episode, in one sentence.
We go deep on the RedBus origin story, the pivot that actually built the company, his 3-phase framework for entrepreneurship (0→1, 1→10, 10→∞), and why he thinks Elon Musk and Mukesh Ambani have something rare that most successful people lose along the way.
What's a "winning habit" you've had to unlearn?
