Failure Feels Confusing Because It’s Incremental
- by: Jatin Chaudhary
Failure in startups rarely happens in a single moment. More often, it creeps in quietly. A customer seems less engaged. A launch lands flat. Numbers stop rising and just sit there. Each signal alone feels fixable. Together, they shift the ground under your feet.
Harsh Pokharna, co-founder of OkCredit, once reflected on how ambition can backfire. On instagram he admitted: “We launched in 14 languages. Then killed most of them.”
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Others describe failure as a slow build of small mistakes. Nithin Kamath of Zerodha put it sharply: “Sustainability is more important than valuation. Misjudging the market size and opportunity, then setting wrong expectations and chasing valuations are probably the biggest reasons why startups fail.”
For some, the lesson is personal. Sam Altman wrote on X: “i failed pretty hard at my first startup–it sucked!–and am doing pretty well on my second.”
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Even future giants have been told their idea was too small. Brian Chesky of Airbnb recalled that in 2008 an investor told him the market “did not seem large enough.”
Founders who endure often share their own grounding habits. Ghazal Alagh of Mamaearth posted on LinkedIn: “Clarity is power. Habit is greater than willpower. Choose discomfort. Consistency over perfection any day.”
Others speak to the emotional whiplash. Paul Graham, in his essay “What Startups Are Really Like,” described it like this: “The emotional ups and downs were the biggest surprise for me. One day, we’d think of ourselves as the next Google and dream of buying islands; the next, we’d be pondering how to let our loved ones know of our utter failure.”
And sometimes the advice is simply to own what has already happened. Mark Pincus said it at FailCon: “If we can all intellectually and emotionally own our failures, then you control your destiny.”
Failure rarely comes as a crash. It comes like a season. Sometimes, by the time you notice, you have already been living in it. The question is not whether you have failed. Everyone does, in small ways. The real question is which story you are in right now: the season of drift, or the season that teaches you how to begin again.
