Reverse Engineering: Gautam Gupta Goes From VC to Entrepreneur

Gautam Gupta had it all. He was just 26 and a rising venture capitalist with a bright future and a big salary. An associate at General Catalyst Partners, he’d sourced six deals, deployed $65 million and had just opened General Catalyst’s Palo Alto office.

Then he threw it all away to launch a startup. And not some cool startup with a mobile-social app poised to be acquired for $1 billion. An e-commerce startup. Even his mother began to wonder.

“My mom’s first question was, ‘Are you sure about this?’” Gupta recalls.

Indeed, it was a surprising decision. Maybe not as surprising as Ben Horowitz’s decision to go public with his unironic and cringeworthy embrace of better management through gangster rap… but still.

Reverse Engineering

Most standout Silicon Valley careers track the other direction, from successful entrepreneur to venture capitalist (see: Peter Thiel, Reid Hoffman, etc.). Why did Gupta go the other way?

“I had never really done anything in my career outside venture capital,” he says. He joined General Catalyst straight out of Babson College. “So now I am 26 and I thought I should spend at least a few years of my life trying to build a business or do something on the operating side before I got too deep into VC and was not able to get out of it.”

Together with a college friend, he started a company called NatureBox, which sells healthy snacks online. He wasn’t completely starting over; General Catalyst provided a large piece of the new company’s seed financing.

Health food is familiar territory for Gupta. He weighed 210 pounds when he was 12 years old – he trimmed his 5-foot-6 frame to 145 pounds by improving his eating habits. E-commerce is also a good fit, since Gupta specialized in e-commerce investments while at General Catalyst. He knows it’s not the sexiest tech space these days, but he likes the challenge.

Solving Difficult Problems

“The first reaction to the food industry you get from VCs is, ‘Why would you want to start a food company? The margins are so low, it’s perishable,’ and on and on. But I like the idea of solving a difficult problem. You can still build an awesome business in the space – it has been done.”

Besides, it’s counterintuitive. Like Gupta.