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YCombinator Founder: "Starting a Startup is Painful"

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By Nishat Kurwa (@nishatjaan)

The founder of YCombinator is very, very happy that he'll no longer be running that startup incubator.

That was a recurring theme of Paul Graham's "Fireside Chat" with Launch founder Jason Calacanis, in which Graham also touched on various lessons from working with more than 600 startups, and being flamed on Twitter for comments about foreign accents and women in tech.

Calacanis opened up by asking Graham a number of questions to follow up on Graham's announcement last week that he's handing the YCombinator reins to Sam Altman.

"it'll look the same to the founders, but it will feel very different to me," Graham said of the leadership shift.

He told Calacanis he'll sit for office hours with startups, but that "other than that, I'm not doing anything...(like) the internal crap that takes up time for most organizations."

Graham said "getting his brain back," and not having to spend so much time thinking about YCombinator was a primary motivation for stepping down, not necessarily the time he spent working on the incubator.

He didn't seem particularly engaged when Calacanis asked some specific questions about startups in various YCombinator cadres, at one point saying that the audience probably knew the answer better than he did. When Calanis asked about the range of valuations in the most recent batch of startups, Graham, looking distressed, grabbing his hair, and pulling at his pant legs, answered, "Who was even in the most recent batch?"

He had much more precise, if not surprising, answers about what he's learned about startup founders as YCombinator's experience with them has grown. In interviews, he admitted, he and the other founders know within minutes whether a startup will make it in, and lock eyes to transmit silent messages if founders are making their eyes glaze over.

He emphasized that founders have to get along ("they hate each other very, very often"), and that the most important thing for founders to do is focus ("you should not be grabbing coffee with investors in the middle of day when you could be working. Do the most important things, like optimizing software").

And although Calacanis gave him wide berth to make a cogent defense of his comments that drew accusations of xenophobia and sexism, none materialized. Graham used the "some-of-my- best-friends-are" varietal, saying "I'm an immigrant myself!," and blamed the pace and acrimony of Twitter for setting the story ablaze. He had a similarly oblique response about female-led startups, saying, "It's half the population. I would have to lose money to be against women starting startups."

(At this point, the man sitting next to me nudged me and said, "There's your piece!" Because -- I'm in that half of the population? Earlier he'd asked me what "got me into gigabytes." He seemed to love Graham's talk, incidentally).

Graham also reflected on the late Aaron Schwartz, who was in the first YCombinator class with Reddit. "Aaron was precocious. He had made a career of being precocious up to that point. He never wanted to do what he was supposed to do. He didn't go to high school, made money, started acting like a grownup. Kids don't realize this -- they could just start acting like a grownup, and no one is going to come with black ski masks and guns and drag them away."

When Calacanis asked Graham if he'd ever do his own startup again, Graham answered emphatically.

"No, no -- never. Starting a startup hurts. (We tell founders) if it's not a certain amount painful, you're probably not trying hard enough."

Public media's Turnstyle News covers tech and digital culture from the West Coast.