Triplebyte's Harj Taggar on the Second-Time Founder Syndrome

by Y Combinator12/9/2015

In this episode of Startup School Radio, host and YC partner Aaron Harris sat down with Harj Taggar.

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Taggar is the co-founder of Triplebyte, a platform for recruiting technical employees. Before founding Triplebyte, he was a partner at Y Combinator, and prior to that, he founded Auctomatic, an online auction technology startup that was acquired in 2008.

Also earlier in the episode, Harris interviewed Jacob Rosenberg, the co-founder and CTO of next-generation loan startup LendUp. You can listen to the entire episode in Soundcloud right here, or via iTunes.

It was particularly interesting in this episode to hear Harj talk about his experience starting Triplebyte, after having one startup success under his belt and working with scores of companies as a partner at YC. This part starts at around minute 41:30:

Aaron : You as a partner at YC were sitting and watching hundreds and thousands of companies every year, with founders who said they were going to create large companies. Did that increase the hurdle, or the pressure on you?

Harj : Yes. The easy answer to that is yes.

I think this is something that I feel like doesn’t get talked about enough out here. I think it’s probably a very specific Silicon Valley issue, and probably even within that subset of people out here in Silicon Valley: It’s what I call the Second-Time Founder Syndrome. And, in particular, the Second-Time Silicon Valley Founder Syndrome. Which is, you’ve seen all of these ideas, and so you really want to obviously work on the one that’s going to be a huge success.

And I think you can start thinking a lot more about which ideas are going to sound impressive when you tell other people who understand startups that you’re hanging out with. Even though, when you look at the data set rationally, the best ideas never really look like the ones that were going to be the best ideas.

That’s the single thing I probably really took away from my time [as a partner at] YC, was that it’s just so hard to predict. Zenefits and InstaCart are probably the two companies that really stand out from my time at YC. And both of those are very solid founders, very plausible ideas and theories, but truthfully, there wasn’t anything that made them stand out in the batch, from all the other ones.

Both of them came into YC purely as an idea with actually very little software — if anything, they were further behind a lot of the other companies that were coming into the batches that had already built and launched. And on the surface, neither of them sounded like amazing ideas. Health insurance, benefits and administration did not sound like it was going to be a multi-billion dollar company. But the founders obviously believed that it would be.

…As a founder, it feels as if the best advice here is do the thing that makes sense to you. Do the things that [address] the problem that you feel you want to solve, not the problem that you think other people think is cool to solve.

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  • Y Combinator

    Y Combinator created a new model for funding early stage startups. Twice a year we invest a small amount of money ($150k) in a large number of startups (recently 200). The startups move to Silicon