I have started three companies. None of them became what I originally mapped out on a whiteboard. One was acquired; two died an unglamorous death. All three taught me things I couldn't have learned anywhere else — and in each instance, the lesson arrived disguised as a minor catastrophe.
This is not a sermon on the spiritual value of losing. Failure is not a gift. It is an expensive, exhausting, and frequently humiliating affair that is entirely obvious in retrospect.
But looking back across a decade of scar tissue, I can see a single, stubborn thread that connected every failure. The killer was never a lack of market size, poor timing, or technical incompetence. It was my own recurring inability to be ruthless with reality — to sit down with myself, my co-founders, and my data, and look at the situation exactly as it was, rather than how I wished it to be.
Bhalu.com: the tyranny of the false binary
In 2009, I was a student at IIT Kharagpur. Caught up in the early, intoxicating fumes of the app economy, my co-founder and I built Bhalu.com — a hyperlocal task marketplace confined to our sprawling campus. It was TaskRabbit for residential college life. Students used it to outsource everything from fetching laundry to smuggling cigarettes past the hostel gates.
The marketplace was shockingly alive. We even ended up hiring a local "man Friday" to handle the logistical overflow. Our metrics eventually caught the eye of an investor from one of India's very few startup accelerators at the time. The offer was life-altering: real capital, on the sole condition that we drop out of school immediately and commit full-time.
Silicon Valley identity: dropping out is a romantic badge of honour. Middle-class India reality: dropping out is considered an act of financial lunacy.
To understand our panic, you must understand the geography of 2009 India. Leaving an institution like IIT wasn't viewed as a daring entrepreneurial leap; it would be viewed by our middle-class families as a profound mental breakdown. We didn't have the generational safety nets required to view a startup failure as a mere detour.
We panicked, refused to drop out, and let the company wither.
For years, I comforted myself with a simple, binary narrative: we chose completing our education over wild ambition. But that framing was a cop-out. The real failure wasn't the decision we made; it was our total lack of administrative imagination. We treated a complex negotiation as a crude "either-or" switch.
We could have negotiated a formal gap year. We could have hired an operational manager to run the campus boots-on-the-ground while we finished our degrees. We could have asked the investor for a six-month probationary period. We explored none of these because the sheer weight of the choice had blinded us to the creative avenues that lie between absolute capitulation and total ruin. In startups, almost every terrifying binary choice is actually a multi-variable problem in disguise.
Croak.it!: the romance of the wrong medium
By 2012, my co-founder Teja and I wanted to build short-form video. There was only one structural hitch: we were sitting in India, 3G was a mythical rumour, and the entire nation was tethered to 2G connections that choked on basic images.
So, we engineered a workaround. If video was an architectural impossibility, we would conquer short-form audio. We built Croak.it! — a platform for 30-second voice clips, complete with filters. We began with a browser extension that allowed users to leave voice annotations across the internet, then graduated to a dedicated mobile application.
Our thesis: audio is the future of low-bandwidth self-expression. The reality: audio was just a temporary waiting room before video arrived.
Raising capital for user-generated content in the India of 2012 was an exercise in theatrical persuasion. The prevailing investor wisdom at the time was that ordinary people merely consumed media; the idea that they would actively create it was considered foreign nonsense.
Against the odds, we raised money from Singapore and secured a coveted spot at Plug and Play in Silicon Valley. We had our bags packed when the US immigration authorities promptly rejected our visa applications.
It was a staggering blow. Banished from California, we performed a frantic geopolitical pivot and fled to Startup Chile in Santiago to maintain a base of operations. But that six-month bureaucratic detour ruined our timing. While we were navigating South American immigration logistics, the macroeconomic landscape shifted beneath our feet.
Vine launched. Snapchat introduced Stories. Most critically, cheap Android smartphones and stable 3G flooded the Indian market. The infrastructure bottleneck that had forced us into audio dissolved overnight.
The world didn't want short-form audio; it wanted video all along. Yet, we refused to pivot.
We had fallen completely in love with our own workaround. We had built an entire identity around voice; we had defended it to sceptical rooms of investors for years. To abandon audio felt like admitting that our grand thesis was merely a temporary patch for a bad network connection — which, in hindsight, was exactly what it was.
We eventually sold Croak.it! to Exotel. It was a soft landing for an exhausted team, but it was a fraction of what could have been achieved if we had possessed the intellectual honesty to separate our mission (short-form self-expression) from our medium (audio). When you marry the implementation rather than the problem, you guarantee your own obsolescence.
Athlete Diaries: the unspoken friction
In 2015, I launched my third venture. The thesis was clean: a dedicated media platform where professional athletes told their own stories, inspired by the success of The Players' Tribune in the United States. In a sports-obsessed nation where non-cricket athletes were treated as historical footnotes by mainstream media, the white space was massive.
We signed forty-one elite athletes — boxers, wrestlers, track stars. I spent my weeks chasing leads, interviewing athletes, editing manuscripts, and publishing raw first-person accounts.
Then, right as our traction began to curve upward, a formal legal notice arrived from the legal representation of the actual Players' Tribune. They were entering India and demanded we surrender our original name, The Players' Diary.
My immediate reaction was unadulterated thrill. If an American giant was sending us legal threats, it meant our small, underfunded operation had shown up on their radar. It was a massive market validation.
My interpretation: "We are David fighting Goliath! This is spectacular marketing!" My co-founders' interpretation: "We are about to be sued into oblivion by an American corporation."
My co-founders did not share my enthusiasm. Where I saw an invitation to rebrand and fight, they saw existential financial risk. The legal letter fractured our psychological alignment. We changed our name to Athlete Diaries, but the early electric momentum had evaporated. My co-founders quietly pulled back from the day-to-day operations, leaving me to handle the interviewing, the engineering, the sales, and the logistics alone. You cannot run a media empire as a solo hobbyist. The platform slowly ground to a halt.
The legal threat didn't kill the company; our unspoken divergence in risk tolerance did. We were perfectly aligned when the graph was moving up and to the right, but we had never stress-tested our partnership for a crisis.
The cost of the slow-motion no
Three companies, three entirely different sectors, and three distinct varieties of autopsy. Yet each failure was born from the exact same psychological luxury: choosing the comfort of a narrative over the cold metrics of reality.
With Bhalu, I accepted a false choice because choosing a binary exit was easier than initiating a complex, messy negotiation. With Croak.it!, I protected an outdated technical medium because admitting we were wrong meant throwing away years of prideful engineering work. With Athlete Diaries, I assumed cultural alignment with my partners because having an uncomfortable conversation about risk at the starting line felt too awkward.
If there is one piece of advice I could pass down to founders currently in the trenches, it is this: the ultimate tax on a startup is the time spent protecting your own ego.
It is the weeks spent ignoring a stagnant retention curve because the daily sign-up volume looks impressive. It is the months spent keeping a disconnected co-founder on the cap table because firing them is too confrontational. It is the slow-motion collapse that we choose to label "persistence" because we are terrified of what happens when we finally stop and turn the machine off.
I don't regret a single mile of the journey. The scars are precisely what gave me the taste to lead large-scale product deployments today. But the real art of leadership isn't learning how to survive the grind; it's developing the courage to look at the data on a bleak Tuesday afternoon and tell yourself the unvarnished truth.