Why I decided to quit my high-paying job to start-up once again?

Leaving the safe harbors in pursuit of solving another problem

It was mid-February 2020, right before the world drove off the cliff with Covid-19 and all travel ceased. I was flying back to Delhi from a meeting with Microsoft in Atlanta.

A year back, I had sold my 1^st start-up to a UK-listed billion-dollar company. My bank account had more digits than I had ever seen in my life. As a part of the deal, I was now a high-ranking honcho on the corporate ladder with great perks and a fabulous 8-figure salary.

Life was great. Gone were the days when I slogged out in the economy class, fighting for legroom on red-eye flights while my co-passenger snored and breathed on me. With my newfound stature, I was now entitled to business class flights with chilled drinks, lie flatbeds, and smiling air-crew cheerfully at my service.

At the time the start-up hustle was at its ferocious prime, I would scramble a last-minute weekend getaway with Mausmi (incidentally my wife and co-founder) to a nearby hill station from Delhi in a half-decent resort with awful food and would still feel guilty about missing work over the weekend. Now, we took leisurely 3 weeks off in New Zealand with great wine, juicy lamb chops, and a top-of-the-line Mustang GT Convertible as our chariot.

In short, life was great. Everything looked set for a cushiony lifestyle. And then, I was asked to go and meet Microsoft at the global innovation center in Atlanta. On my return leg to Delhi, I had a stopover in Munich. The ground crew informed me that I was being upgraded to 1st class. Wow! I was ecstatic.

Just before the boarding, I went to a coffee shop and ordered a latte. The shop was crowded, so I had to sit at a table that was occupied. That’s when I met this guy. He was sipping his coffee and looking pale and tired. We got talking and he told me that he was a founder of a fledgling start-up. When we started discussing his product, his tiredness just sublimated and his eyes shined and his voice became animated. He was excited. His infectious zeal and passionate oratory about his start-up moved me. I was impressed.

Shortly after that, we took off. The 1^st class is a resplendent lavish affair. It is like having your own mansion 30,000 feet in the air. The pampering with chilled champagne and a procession of entre was incessant. I felt like a king. After a lovely meal of lobsters and brandy, I stepped out of my luxury 1st class cocoon and peeked into the cattle class economy cabin. It was nighttime. The lights were dimmed. A few entertainment screens were on and I saw the founder peering into his laptop and whipping up a storm on his keyboard.

“That guy used to be me.” I thought. Not long back, on all overnight flights I would review designs, draft replies to emails, straighten out my presentations, did my expense logging… And nowadays I would be shrouded by luxury and comfort and watch movies. I racked my brains. What did I remember about my meetings in Atlanta? The after-meeting dinner spread of brisket and the wine were great but the meeting was bland and had nothing that stimulated my thoughts.

And that’s when I got my epiphany. I didn’t want this – no more. I needed to be in the economy seat – tired to the bone, scared shitless but never short of inspiration and drive.

The sterile lap of luxury and security was great but the nervous tension emanating from the creative anxiety of building a start-up is a drug that once taken – hooks you up for life.

I had to pitch to 119 investors to get my 1st investment dollar in my last start-up. I used to spend 100 days around the world, always flying economy, showing people our innovation… There was enormous pressure to deliver, scale, and grow. It was breathless and intense but it was never sterile. It was never boring.

A start-up is a romance. It starts from a rational urge to creatively solve a problem at hand and then comes the irrational part of leaving the safe harbors in pursuit of the solution. And in that maelstrom of chaos and disorder, you strive to build structure and meaning and hopefully some success.

30,000 feet in the air, ensconced by the opulence of the 1st class, I realized that I belonged to the back of the plane where you fight for the legroom, you fight for another inch to recline your seat, you fight fatigue and demons in your head but you are always inspired and always raring to go.

I knew I was quitting, I knew I was starting up again…