A program so nice, these founders did YC twice

Parker Conrad may be best known as the founder of both Zenefits and Rippling, but he is also arguably the best-known founder to have gone through Y Combinator’s accelerator program twice. Of course, he’s not the only one to go through the program twice; some founders have even gone through three times.

Y Combinator has been around for over a decade and is still largely considered the premier startup accelerator. Now that founders from its earlier cohorts are starting new companies, it only makes sense that the number of repeat founders has grown.

The accelerator is an intensive 11-week startup building program with the aim of propelling startups to the next level. YC also gives its company cohorts $500,000 in funding across two SAFE — simple agreement for future equity — notes.

There were eight repeat YC founders in this latest summer batch, per my count (check out our faves from Day 1 and Day 2). Some recent batches like winter 2023 and summer 2022 had even more. But is the program really worth doing a second time? For repeat YC founders, the answer is a resounding yes.

“Garry Tan mentioned something when he came back to YC, and it was a really poignant comment that stuck with me, it was a sense of ‘coming home,’” said Jay Reno, the co-founder and CEO of Pointhound, which lets users find and book flights using miles. “Which is not the exact way I would describe it, but it is coming back into a community you really admire and get inspired by.”

All four repeat YC founders who spoke to TechCrunch+ for this story all expressed that their love for the program, the partners and community gave them reason to go back. And building alongside other founders is incredibly motivating for them, too. But all the loving and gushing aside, there are some practical reasons for why these founders decided to do the intense three-month-long program after having gone through it at least once before.

Brian Brunner, the founder and CEO of DataShare, a data-as-a-service startup, said that he went through YC for the first time back in 2014. Not only have his career and experiences changed him over the last nine years, but also early-stage venture has gone through quite the transformation as well. “I think I was actually able to get a lot more out of it this time just because of maturity,” he told TechCrunch+. “Some of the lessons are the same, like move early, fail fast, find your early customers; I don’t think that’s changed, but I don’t know if that is the magic of YC.”

Other founders said they had more to learn, even after successfully growing and exiting a company. Tim Griffin, the co-founder and CEO at Craftwork, a tech-enabled home service professional startup, is now working in a new sector, for example. His last startup, Cloosiv, is a mobile ordering system for coffee shops. It went through the summer 2019 batch.

Another reason Brunner said he reapplied for the program is that he was looking for support as a solo founder, which is also different from the first time he went through the program. YC offers a community to bounce ideas off of in a way one might do with their co-founders. “Not having a co-founder but a group of people around me going through the same thing, it’s great for feeling out, ‘am I in the right place?’ and it’s good to commiserate,” Brunner said.

For other companies, it is the opposite. Jeremy Osborne, the co-founder and CEO of Helios Climate Industries, a tech-enabled heat pump contractor, said part of the reason he wanted to do it again was that his co-founder hadn’t been through the program yet. Plus, Osborne himself had been through as a founder but not as a CEO.

“It is a little bit different now,” Osborne said. “I also was very careful at the start to not assume I knew anything. Because it’s changed, I’m going to pretend like I don’t know too much.”

Another factor is fundraising. Reno said that fundraising is a slog, especially in a tougher market, and having that boost definitely helps. “It’s a different game where investors all find you rather than you having to go outbound,” Reno said. “There are a lot [fewer] misses.”

While it makes sense to bring back founders for another go, especially if they are getting just as much out of it, it’s unclear whether it makes sense for YC. The program accepts only 1% of applicants, and if an increasing number of those selected have done the program before, it makes it that much more selective for those who haven’t had a chance. A spokesperson from YC said repeat founders currently makes up only 1.5% of the overall group and that the organization looks at repeat founders as a positive.

But, hey, if founders find it helpful to go through it more than once, and there isn’t anything against it, why wouldn’t they?

“I’ll see Twitter threads that say, ‘I had an investor tell me not to do it.’ I’ve never heard a valid reason to not do it,” Griffin said. “If Parker Conrad can do it multiple times, so can you.”