JS Jamie Siminoff On How I Built This (Guy Raz)

“I feel like nothing in business is complicated. It's hard. Like Kinko's was hard, but it wasn't complicated. And I think the problem is when we take this approach of that something's complicated, it scares us. We can't do it. It's too difficult.”

How I Built This (Guy Raz) · Startups & Venture · October 2026

“I feel like nothing in business is complicated. It's hard. Like Kinko's was hard, but it wasn't complicated. And I think the problem is when we take this approach of that something's complicated, it scares us. We can't do it. It's too difficult.” — Jamie Siminoff, How I Built This (Guy Raz)

From the show's tenth anniversary episode, where Guy Raz replays old interview clips and asks guests to react. Siminoff is responding to a clip about Kinko's.

Transcript

How I Built This (Guy Raz) Around 06:27 into the episode
Sam Calagioni

Money.

Guy Raz

Jamie, what do you think?

Jamie Siminoff

I feel like nothing in business is complicated. It's hard. Like Kinko's was hard, but it wasn't complicated. And I think the problem is when we take this approach of that something's complicated, it scares us. We can't do it. It's too difficult. Versus like when you heard his answer, it's like, yeah, there's a line.

Guy Raz

And how many times, I'm sure you experienced this, you're somewhere, something happens, and you're like, why do they make a, you know, this thing like that? Like, why you're sitting around, you're like, why doesn't somebody make a coffee cup that's, you know, square shaped or that has like a gyroscope on the bottom so it never falls over something, right? Why doesn't X exist? But then there are people who actually do it. They're like, yeah, it's like you. You're like, why can't we see who's ringing the doorbell, you know, when I'm in another part of my house?

Jamie Siminoff

And it is. It's like the hard part is like, it's like walking into that dark tunnel. When again, when you simplify it, it's like not that crazy to try it. Like, it's just like, it's like, just do it.

Guy Raz

One of the things that I love that comes up from time to time is, you know, we'll have, there's a certain type of founder. And I don't want to say, I hope this sounds, this doesn't sound like I'm typecasting them, but it's like somebody goes to business school. And they're, a lot of them still today go into consulting or into venture and finance. And occasionally we've had founders who were went into venture out of graduate school. And They're the ones who are like the analysts. They're the low-level analysts just vetting all these people pitching ideas for money. And that was a story of Katrina Lake and Stitch Fix. She was at a VC fund in the Bay Area, and she would listen to people pitch ideas to her all day.

Speaker names from our own diarization · position estimated from where the line sits in the episode

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