A former Y Combinator partner realised the most successful founders don't always look good on paper — there's a much more reliable sign they're destined for greatness

Courtesy of Harj TaggarWhat do you work on in your spare time? Harj Taggar pictured.
  • Harj Taggar is a former partner at Y Combinator, the tech accelerator that launched a number of successful startups including Airbnb, Dropbox, and Instacart. He’s currently the cofounder and CEO of Triplebyte.
  • Taggar said he and his YC partners placed a high value on learning what applicants did in their spare time.
  • The YC application still includes the prompt: “Please tell us about an interesting project, preferably outside of class or work, that two or more of you created together.”
  • The YC partners looked specifically for people who had created projects or explored new ideas beyond the requirements of work or school.

When he joined Y Combinator as a venture partner in 2010, Harj Taggar was the first full-time employee at the startup accelerator. He and his partners were constantly refining their selection process.

As they watched accepted entrepreneurs build their businesses, the partners came to one glaring realisation: The most successful founders didn’t always look so good on paper.

Taggar, who is currently the cofounder and CEO of Triplebyte, told Business Insider: “Often, we’d fund people that had been promoted and risen up the ranks at really top quality companies like Google. But they’d work at a startup and they couldn’t handle the ambiguity. It wasn’t a good fit for them.”

On the other hand, Taggar said, they’d see people “who had an unusual background, an eclectic mix of things that they’d done, and actually turn out to be really great at [entrepreneurship].”

He and his partners became obsessed with figuring out the best ways to identify top talent, without relying on resumes.

At some point, they realised that one of the best predictors of a founder’s success was what the founders did in their spare time.

“What projects did they work on, and in particular when did they work on projects out of personal interest, because they thought that they would learn something or they were just curious about something?” Taggar said. In other words, he was less interested in projects they did because it was required for school or for work.

The Y Combinator partners started looking more closely at founders’ responses to a prompt that’s still on the application today: “Please tell us about an interesting project, preferably outside of class or work, that two or more of you created together.”

Y Combinator looks for curiosity and the willingness to test new ideas

In the last decade, Y Combinator has launched a number of successful startups, including Airbnb, Dropbox, and Instacart.

Some startups that have applied to Y Combinator have publicly posted their initial applications, so you can see how they responded to that particular prompt.

When The Muse cofounders applied, in 2011, they mentioned a “10-year strategic review for Sesame Workshop (aka Sesame Street)’s South African production, Takalani Sesame.” Drew Houston, the founder of Dropbox, applied in 2007 and mentioned an online SAT prep company he’d previously launched.

And when the cofounders of Buffer applied, in 2011, they wrote simply, “There are no shared projects before Buffer.” Interestingly, they were rejected – although they have now raised $US3.9 million.

Taggar recalled the application submitted by Brian Armstrong, cofounder of Coinbase. At the time, Taggar said, “it wasn’t clear that [Bitcoin] was going to be anything particularly popular. But [Armstrong] had already spent a bunch of time building tools for it and making it easier to buy Bitcoin.” Taggar said it was evident that Armstrong was simply interested in this “cool new thing.”

Armstrong’s interest in building cryptocurrency tools on the side is a prime example of what Y Combinator is looking for, Taggar said. “We found that a predictor of would we want to fund someone is: Is this someone that’s got a curiosity about the world and likes getting ideas off the ground to see what happens?”

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