10 Years of How I Built This: A Decade of Innovation, Risk and Reinvention

How I Built This with Guy Raz

Guy Raz celebrates the 10th anniversary of How I Built This by revisiting foundational episodes with guest Jamie Siminoff, founder of Ring. Togethe

Key takeaways

• Jamie Siminoff reflects on how fear motivated him to build Ring and emphasizes that entrepreneurs often put themselves out of business through panic rather than external forces.
• Sam Calagione's lightbulb moment for Dogfish Head Beer came from squishing cheap, fly-covered cherries into a homebrew kit in his Manhattan apartment.

Main topics

• Fear and vulnerability in entrepreneurship
• Scrappy experimentation and iteration

Notable quotes

"The thing that I believe puts companies out of business is yourself."

Conclusion

The episode serves as both a retrospective and a practical masterclass,

Transcript preview

Speaker 1 (0:08) There's so many things to worry about in business, including what you don't know. And so I am always kind of panicked. You know, fear drives me. You know, now I'd say it's a digestible fear. Back then, I had everything in this thing. And if it went away, such a giant thing that I had built would have been just, you know, wiped out. I'd have nothing. I always say, like, the thing that I believe puts companies out of business is yourself. I was terrified. Speaker 2 (0:38) Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built. Speaker 2 (0:52) I'm Guy Raz, and on the show today, it's our 10-year anniversary. And we're listening back to some of our favorite moments, a decade of lessons and stories about struggle, doubt, failure, joy, catastrophe, and, of course, success. Speaker 2 (1:13) So 10 years ago, we started How I Built This. And the idea was actually pretty simple. I was just really curious about the people behind businesses and how they actually built them. Because when you really get into these stories, they're kind of amazing. Things go wrong. People make mistakes. People run out of money. Relationships fall apart. They get rejected, sometimes over and over again. And then sometimes, miraculously, something works. And I think what we all realized in the show pretty early on was there was just so much to learn from these stories. And not just about business, but about taking risks or dealing with failure or solving problems or figuring out what to do when you have absolutely no idea what to do. Over the last 10 years, we've talked to more than 600 founders, people like Jensen Wong and Sarah Blakely and Howard Schultz, and also the founders of Netflix and Airbnb and Chipotle and so many others. And I have learned a ton from them. And I hope that somewhere along the way, you heard something on the show that helped you or inspired you or maybe just gave you a little push to try something you weren't sure you could do. But mostly. I just want to thank you for listening because 10 years is a long time. And the fact that so many of you have stuck with us and spent all these hours with us, it really means a lot. So for this anniversary show, we went back through hundreds of episodes and we pulled out some moments that have stayed with us, things that surprised us and things we learned and things we still think about. And to help me do this, I invited Jamie Siminoff, the founder of Ring, to come back and listen with me. Because Jamie also happens to be a huge fan of the show and a careful listener. And you also heard Jamie's voice at the top of the show talking about how fear actually motivated him to keep going. Speaker 1 (3:08) It's funny to listen to yourself saying that stuff. I think the most important thing in that clip, which I still think is so true, is... We put ourselves out of business. It's more us than anyone else. And the problem for entrepreneurs is they can't see the light at the end of the tunnel, no matter what you tell them. And so we're trying to show them that there is light there, that you can keep going forward and further. And so I think it is important because once you've gotten there, you've probably had someone else help you get there. It's Speaker 8 (3:35) like you pay it forward. There's a real Speaker 2 (3:37) vulnerability in what you say here, which I think is emblematic of what we hear on the show. You're like, fear is real. There's this cliche about being an entrepreneur or being a successful business person, you know, like, oh, fearless. I jump out of airplanes. And some people are like that. That's true. And occasionally we've had people on the show like that. But I think in general, I think fear has to be real. I mean, it's a human instinct. It's there to protect us and to make sure we don't actually die. Speaker 1 (4:06) And I think if you can, if you are like me and you have a lot of fear, I think you can use it to fuel yourself. And I think a lot of times fear can also have the opposite effect, which is it sort of, you know, you like, you sort of panic attack it. Like you just, you get like seized up and you can't move, you know, 3am. There's something about 3am. I wake up when I'm, when I'm in that sort of mode. Yes. I mean, on the dot, like three zero zero. Like, I don't know what Speaker 8 (4:32) it is, but there's like a. There's Speaker 2 (4:33) a Speaker 8 (4:33) 3am. panic button encoded in our genetics. And I'm sweaty. Yeah. And I'm like upset and I'm like scared and my brain is freaking out. Speaker 1 (4:44) It's Speaker 2 (4:45) the worst. All right. So a lot of people will ask, well, how do you start? How does a business start? And my, what am I? very simple answers is, and I know you have a version of this, is what is a problem you have that other people have too, that you can solve for yourself and many other people? And this is really what, you know, we sort of call the light bulb moment on our team when we're producing the show. We want to find, we're looking for that light bulb moment of The world needs X. And so I want to play a clip. This is of Sam Calagione. He is the co-founder with his wife, Maria, of Dogfish Head Beer. And this was the moment that he decided to start brewing beer in his apartment in Manhattan. Speaker 5 (5:26) As I was walking to my apartment with my homebrew kid, I passed a bodega that was having a sale outside on like all this moldy or just squishy like. fruit fly covered fruit and for some reason i was like oh my god look at all those cherries look how cheap that is what if i take this pale ale kit and squish the cherries into it you know it's not the recipe but i wonder how that would taste so that was kind of the moment you know for me i took that kit home and started boiling it in our little tiny apartment Speaker 2 (5:56) Little did he know that he would eventually, because of that, create a global, world-class, award-winning beer that had a huge impact on craft beer making. And I mean, Speaker 1 (6:07) I love how he even describes it. Like, you know, the flies and he doesn't sort of hold any punches. It's just like, I walked by this, you know, crappy thing, saw this sort of like toss away stuff and thought, why don't I just do this? You know, I think it's why so many startups start in garages. And I'd say like his apartment in this case. kind of was the New York version of a garage. Like, I think what a lot of times happens when people start businesses is they so quickly get to where they're forced to try to make the business work that they don't have that time to have that experimentation. And the garage is like sort of Speaker 8 (6:39) this embodiment of that. Totally. Yeah. Speaker 2 (6:42) I mean, sometimes it's also a reminder that, you know, when your eyes are open, you start to see things, right? It sounds like it's self-evident, but it's sometimes important to remind ourselves of that. I mean, there's also, we've also had founders on who, And there's nothing wrong with it. They want to make money. For whatever reason, they have a passion for figuring out how to make money. And this was a story we came across. It was a great episode. We told the story of Kinko's and Paul Orfala. And he was at USC. And he noticed really long lines outside of a copy store. Speaker 5 (7:19) This place called Magic Machine, it was right by SC. They did Xerox copies for three cents a copy. Speaker 2 (7:25) And there were lines, unbelievably long lines. And this is in like 1969. And photocopy machines were like these giant things. And it took like a photograph. Like it was like, there was like a flash of light for every copy, right? Yes. At the time? Yes. Speaker 5 (7:42) And you could just see so many applications for it. I could just see it mushrooming. Speaker 2 (7:47) And what does a long line mean to you when you see a long line? Speaker 5 (7:51) Money. Speaker 8 (7:53) Jamie, what do you think? I feel Speaker 1 (7:55) 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, Speaker 8 (8:12) yeah, there's a line. And Speaker 2 (8:14) how many times, I'm sure you've experienced this. You're somewhere, something happens, you know, like, why don't they make a, you know, this thing like that? Like, 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? Speaker 1 (8:42) 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 Speaker 8 (8:52) just like it's like just do it. Speaker 2 (8:54) One of the things that I 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 how the sounds. This doesn't sound like I'm typecasting them, but it's like somebody goes to business school. And there are a lot of them still today go into consulting or to 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 in 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 7 (9:37) I probably met over 100 entrepreneurs in the time that I was there. And the most important learning, actually, was that all of these people were just like super unqualified, normal people with lots of ideas, just like I was. Speaker 2 (9:50) They weren't like these superheroes with like, they were just really good at, I guess, kind of like making the case for their idea. Speaker 7 (9:58) Yeah. And so I think it was actually the more powerful thing was that I realized that if I have all these ideas about what should be happening, like I don't need to be in the peanut gallery lobbying my ideas at people, like I should just do it myself and that I could do it myself. Speaker 2 (10:13) Yeah, it's a cool story. And she was one of the first founders, female founders to take a company public. And it was a great, great story. I mean, it, you know, Stitch Fix went through its ups and downs. But yeah, I mean, that's a thing like that. Just being in that position thinking, I think I could do that, too. Speaker 1 (10:28) Yeah, I call it like the country club effect. It's like, you don't know what's behind the wall because like you're not a member. And it's I think, you know, she saw it in her way. I hope the internet, YouTube, shows like yours are democratizing this more and more so that young people feel like these walls don't exist and they can just do it. But Speaker 2 (10:47) it's hard. And it's not like, we're not a hustle culture show. And again, I hope it doesn't sound like we're just promoting the show. That's not what I'm, but what I think, yeah, sorry. But being Speaker 8 (10:57) able to hear stories like she, she Speaker 1 (11:00) was at a VC, which typically that's how you had to hear these stories. You've allowed it to be democratized. to let kids listen to it on their iPhones or whatever. And I just think once you hear enough of them, you're like, oh, I can relate to these people. Speaker 2 (11:14) Yeah, exactly. One of the things, and we talked about this a little bit earlier, about this idea of fear that really does animate a lot of these stories. And one of the stories we told in the early days was about Sam Adams Beer, Boston Beer Company, founded by this guy, Jim Cook, who's just a lovely, wonderful. person. And he was a consultant. He was at Boston Consulting Group. He had a really stable job. But he was bored and he wasn't happy. And he decided to quit. And Speaker 3 (11:48) it's the difference in life between things that are scary and things that are dangerous. And there are plenty of things that are dangerous, but not scary. Those are the things that get you. I can give you a climbing analogy from Outward Bound. Like one of the things we taught people to do was rappel off a cliff. And they're really, it's a very scary thing to do. But you're also held by a belay rope and that rope will hold a car. So walking off the cliff backwards is scary but not dangerous. Yeah. Okay. Walking across, you know, 35. degree angle snow field on a beautiful afternoon with this blue sky. It's not scary at all, but it's very dangerous because the snow is melting. Eventually, it's going to find a layer of ice. The water will lubricate that, and you have an avalanche. That is dangerous, but not scary. And in my situation, staying at BCG was dangerous, but not scary. And the danger there, the risk was continuing to do something that didn't make me happy and getting to, you know, 65 and looking back and go, oh, my God, I wasted Speaker 2 (13:12) my life. I thought about this quote. so many times over the last 10 years in my own decision-making, like, am I going to regret not doing this in five, 10 years, Speaker 8 (13:24) even if it's scary? I think to be fair, Speaker 1 (13:27) the young, this is where the younger you are, the less dangerous that slope is, you know, of, of the thing, because you have less, you know, as to be fair to people when they're, you know, I do feel bad for someone who's 45 and has three kids and a family. And you say like, Oh, leave your job to do this thing. It's like, You're starting to get to that point where that's not just, you know, you can't just do that. You have other dependents. Speaker 2 (13:49) Yeah. That being said, we do love founders who start businesses after 40, and we've done many, many, if not half of our episodes. have been the founders who started later. And again, I agree. I respect that so much because it's harder, but you also have advantages when you're over 40. You know, you've made connections in business and in life and you've got more credibility because you have experience. I Speaker 1 (14:12) could say firsthand. I mean, my son Oliver was three when I started Ring. And I remember the times when, you know, like, it's like, this thing's not going to go well. And like, I'm going to have to like move my... family out of a house. Like the weight of that is extreme. Now, by the way, it sadly also maybe pushed me. So like it was that fear of that also pushed me. But I wouldn't wish that on anyone, that emotion. I certainly don't wish that on anyone. Speaker 8 (14:38) But yeah. Right. Speaker 2 (14:40) One of the stories, it's one of the very few nonprofit stories. A lot of people ask me why we don't do more nonprofits. And it's not because I don't like them. Nonprofits are awesome. It's just in general, and I know I'm going to get letters from people, but in general, the stakes are different because if a nonprofit fails, usually there isn't a lot of money that people have put on the line, you know, that's catastrophic. But we did tell the story of Khan Academy early on and maybe five, six, seven years ago. But Sal Khan did take a massive risk. I mean, he was a guy. He went to MIT, went to Harvard Business School. I mean, he had tons of. massively lucrative offers. He did work in finance for a while. I mean, he's a guy that decided, and again, this is a kid who grew up with almost nothing. I mean, he was raised in, you know, just outside of New Orleans in Louisiana. He was like a scholarship kid. His family were immigrants. He had nothing. And I remember him telling me the story about, you know, explain to his mom, you know, that he was leaving this lucrative job and how stressful that was. Speaker 8 (15:44) You can imagine my mother who, you know, when I told her I'd quit my job, you know, I still remember her Speaker 5 (15:49) first word was, what? It was literally in that tone because, you know, I had now fallen into a really lucrative career. And then to give that up and to do that for something that was like not something that she could tell her friends at the next Indian party. Not only was there a monetary aspect to it, there was probably a shame aspect to this as well Speaker 2 (16:12) that was hard. I mean, and it's not only like, and this story comes up oftentimes, especially with people from immigrant backgrounds. But, you know, I remember, by the way, when I first started my career back in the late 90s, I started out. working at NPR. But at the time, my parents didn't know what it was. I didn't grow up listening to it. And I remember just feeling like, God, I thought it was a big deal. But they really, when their friends would ask, they'd say, is working in a radio station in Washington, D.C. So I know Speaker 8 (16:47) the feeling. I mean, I went and Speaker 1 (16:50) made doorbells, so I know the feeling too, which is, you know, it's easy to forget that when like... You know, when you started with a doorbell at that time, it was like a joke. But like, it's what he did is unbelievable because he did. He left such a lucrative thing to do something that like this democratizing of knowledge, intelligence, learning, like all these things. I mean, he is a foundational piece of that that has changed really. I think it has changed the world. Speaker 2 (17:17) You know, whatever we're talking about, whether it's a piece of apparel or food, we really get into the garage, so to speak. And one of the things I just love about getting into the garage is the obsessive experimentation and iteration, even with things like peanut butter. Speaker 5 (17:32) I would do a peanut butter and grape jelly, peanut butter and strawberry jelly, and I'd mix them together in the food processor. So very quickly, I had 30 or 40 different jars. We did Justin's Speaker 2 (17:43) Nut Butters, and Justin Gold, the founder. He was obsessive about, and you're thinking peanut butter. What's so, you know, what do you, but actually he was making so many different kinds of peanut butter and ways to make it and trying to, because it is a complex product. There's oil and all the stuff and they want to add flavors. Let's just say you wanted to make honey Speaker 5 (18:02) peanut butter. It sounds simple. Three ingredients. Right. Peanuts, honey, and salt. Right. All right.