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

Stories about starting a business are almost always full of drama. They’re about ambition, loss, triumph, catastrophe, resilience. And they’re also full of life lessons – which is why Guy Raz launched How I Built This 10 years ago: He wanted to host a free master class in entrepreneurship, one conversation at a time. Ten years on, he’s conducted over 600 interviews with some of the world’s most successful founders, and on today’s show, he replays some of the most memorable moments and lessons. Joining him is Jamie Siminoff, the founder of RING and a former guest on the show. Why Jamie? He’s a friend, a fan, and – as you may remember from his first interview - he doesn’t hide his emotions. Timestamps: 7:38 A lightbulb switches on at an NYC bodega: “Oh my God, look at all those cherries!” 11:52 The moment Stitch Fix founder Katrina Lake realized she should start her own business. 13:50 The difference between scary and dangerous, and why it matters for founders 21:17 Eileen Fisher’s first, terrifying trade show: “I couldn’t speak. I just stood there.” 26:56 “Everything was on one computer?” The chaotic launch of Instagram 31:15 How Sara Blakely sold her first Spanx 35:45 The marketing genius behind Liquid Death 42:22 Why 2008 was the worst year of Joe Gebbia’s life 50:01 How the co-founder of Banana Republic fell asleep at the wheel—literally 58:39 Makeup mogul Bobbi Brown on selling to Estee Lauder: “I am not a follow-the- leader-kind of person.” 1:06:59 Luck, skill, and staying on the surfboard This episode was produced by Casey Herman, with music by Ramtin Arablouei. Edited by Neva Grant. Our audio engineer was Robert Rodriguez. Follow How I Built This: Instagram → @howibuiltthis https://www.instagram.com/howibuiltthis/ X → @HowIBuiltThis https://x.com/howibuiltthis Facebook → How I Built This https://www.facebook.com/howibuiltthis Follow Guy Raz: Instagram → @guy.raz https://www.instagram.com/guy.raz/ Youtube →guy_raz https://www.youtube.com/channel/UCNSfrxNEmCruNtjIzxCBHjg X → @guyraz https://x.com/guyraz Substack →https://urldefense.com/v3/__http:/guyraz.substack.com__;!! Iwwt! RZoD751oWzUzoqqdJiqaoL6HdJfRHDUO1TKvYJ424d3Udn7-Pw9Nj6nEsauh9zcgEvLjUEc$guyraz.substack.com http://guyraz.substack.com/ Website → guyraz.com http://guyraz.com/ See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Guy Raz?

  Our presenting sponsor today is Anthropic, the team behind Claude. Every founder on this show started with a hard question, not the marketing plan, the 2:00 AM kind. Is this idea any good? Am I the one to build it? Should I quit my job? Anthropic got built the same way, a public benefit corporation founded on one hard question. How do we make sure AI goes well for people? So they asked over 100,000 people their hopes and their fears and are publishing what they find, even the uncomfortable parts. Me? I've got my own hard question about AI. Here it is. If everyone has access to something that can help them write the business plan,

• 0:45Guy Raz?

  build the prototype, analyze the market, maybe even come up with the idea, what separates the people who actually build something from everyone else? I don't have a clean answer yet, so I've been sitting with it with Claude. There's hope in hard questions. Ask yours at claude.ai/hibt. We get support from US Bank, a question I love asking founders. What's the one decision you almost didn't make, the one that changed everything? Because it's never the obvious stuff. It's never, I decided to start a company. It's the small, boring, Tuesday afternoon decision you barely remember making until

• 1:27Guy Raz?

  you realize it's the reason everything after it either worked or didn't. Say you're 18 months in, business is growing, you've got expenses coming from six directions, gas for the van, office supplies, your phone bill, team lunches that are actually client meetings, and you're putting it all on whatever card you grabbed in year one. You're not thinking about it. Why would you? You've got bigger problems. But here's the thing. Path A, you keep going like that. End of the year, you're sorting through statements, trying to figure out what went where. You've left hundreds, maybe thousands on the table in rewards you never earned, money that could have gone back into the business.

• 2:07Guy Raz?

  Path B, you pause and get the US Bank Triple Cash Rewards Visa Business Card. Now you're earning 3% cash back on gas and EV charging, office supply stores, cell phone service, and restaurants. You pick up an extra $750 cash back as a bonus. And you've got a low APR on purchases and balance transfers for 12 months while you're scaling. Same business, same expenses, two completely different outcomes based on one small decision. Visit usbank.com/business to learn more. The creditor and issuer of this card is US Bank National Association pursuant to a license

• 2:50Guy Raz?

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• 3:33Guy Raz?

  each medallion year when flying Delta together. That's up to $950 in annual value. Value estimate based on $50 per visit rate to purchase additional visits or bring a guest to the Delta Sky Club. Make every trip feel more rewarding with the card that upgrades your travel. Apply today at delta.com/cardsocial. Offer ends November 4, 2026. Minimum spending requirements and terms apply. Flights are fulfilled as flight certificates valid for Delta Comfort or Delta Main to select domestic destinations. Book 21-plus days in advance. Up to $80 per person and taxes and fees apply. Other restrictions apply.

• 4:14Guy Raz?

  When I pull up to a gas pump to fill my car, I'm not thinking about chemistry or engineering. I'm thinking about getting in, filling up, and getting on with my day. And it reminds me a little bit of the founders I talked to on this show, because the best ones obsess over things their customers will never see. Tiny details, invisible improvements, relentless iteration. And not because anyone's watching, but because it makes the product better. That's what the mobile brand does. It engineers fuel the same way great founders engineer their products. Mobile Supreme Plus Premium Gas helps keep engines three times cleaner, which can mean better performance and improved gas mileage.

• 4:56Guy Raz?

  It's for people who care about what's under the hood, even if they never see it. Three times cleaner compared to mobile regular gas in port fuel-injected engines. Actual results may vary. Visit mobilefuels.com for details.

• 5:19Speaker 01

  There's so many things to worry about in business, including what you don't know. And so I am always kind of panicked. Fear drives me. 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 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.

• 5:49Guy Raz?

  Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.

• 6:03Guy Raz?

  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.

• 6:24Guy Raz?

  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 on this 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.

• 7:09Guy Raz?

  Over the last 10 years, we've talked to more than 600 founders, people like Jensen Huang, 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,

• 7:51Guy Raz?

  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.

• 8:19Speaker 01

  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 like you pay it forward.

• 8:47Guy Raz?

  There's a real vulnerability in what you say here, which I think is emblematic of what we hear on the show. You're like, fear is real.

• 8:55Speaker 01

  Yep.

• 8:55Guy Raz?

  There's this cliche about being an entrepreneur, being a successful businessperson, 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.

• 9:17Speaker 01

  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 seized up and you can't move.

• 9:34Speaker 01

  3:00 AM. There's something about 3:00 AM. I wake up when I'm in that sort of mode.

• 9:39Guy Raz?

  Yes.

• 9:39Speaker 01

  I mean, on the dot, like 3:00, 00. Like, I don't know what it is, but there's like a-

• 9:44Guy Raz?

  There's a 3:00 AM panic button encoded in our genetics.

• 9:47Speaker 01

  And I'm sweaty.

• 9:48Guy Raz?

  Yeah.

• 9:49Speaker 01

  And I'm like upset and I'm like scared and my brain is freaking out. It's the worst.

• 9:56Guy Raz?

  All right. So, a lot of people will ask, well, how do you start? How does a business start? And what are my 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 lightbulb moment on our team when we're producing the show. We want to find, we're looking for that lightbulb moment of, "The world needs X." And so I want to play a clip. This is of Sam Caligoni. He was 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.

• 10:37Speaker 01

  As I was walking to my apartment, my homebrew kit, 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.

• 11:06Guy Raz?

  Little did he know that he would eventually, because of that, create like a global, like world-class, award-winning beer that, you know, had a huge impact on craft beer making.

• 11:17Speaker 01

  And I mean, I love how he even describes it, like, you know, the flies and like, he doesn't sort of hold any punches. It's just like, "I walked by this 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 this embodiment of that.

• 11:52Guy Raz?

  Totally. Yeah. 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, you know, 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 Orfola. And he was at USC. And he noticed really long lines outside of a copy store.

• 12:30Speaker 02

  This place called Magic Machine, it was right by SC. They did Xerox copies for three cents a copy, and there were lines, unbelievably long lines.

• 12:38Guy Raz?

  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?

• 12:51Speaker 02

  Yes.

• 12:51Guy Raz?

  At the time?

• 12:52Speaker 02

  Yes. And you could just see so many applications for it. I could just see it mushrooming.

• 12:58Guy Raz?

  And what does a long line mean to you when you see a long line?

• 13:02Speaker 02

  Money.

• 13:03Guy Raz?

  Jamie, what do you think?

• 13:05Speaker 01

  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."

• 13:24Guy Raz?

  And 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, "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?'"

• 13:53Speaker 01

  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.

• 14:05Guy 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, this doesn't sound like I'm typecasting them, but it's like, somebody goes to business school.

• 14:18Speaker 01

  Yeah.

• 14:18Guy Raz?

  And there, a lot of them still today go into consulting or to venture and finance. And occasionally, we've had founders who 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.

• 14:48Speaker 03

  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.

• 15:01Guy Raz?

  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.

• 15:09Speaker 03

  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.

• 15:23Guy Raz?

  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, 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."

• 15:39Speaker 01

  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.

• 15:58Guy Raz?

  But 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 I think, yeah, sorry.

• 16:07Speaker 01

  But being able to hear stories, like she, you know, she was at a VC, which typically, that's how you had to hear these stories.

• 16:14Guy Raz?

  Yeah.

• 16:14Speaker 01

  You've allowed it to be democratized to like kids listen to it on their iPhones or whatever. And I just think it, once you hear enough of them, you're like, "Oh, I can relate to these people."

• 16:25Guy Raz?

  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, you know, he just, but he was bored. And he wasn't happy. And he decided to quit.

• 16:58Speaker 04

  And 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.

• 17:09Guy Raz?

  Yeah.

• 17:09Speaker 04

  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.

• 17:34Guy Raz?

  Yeah.

• 17:35Speaker 04

  Okay. Walking across, you know, a 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.

• 18:15Speaker 04

  And getting to, you know, 65 and looking back and go, "Oh, my God, I wasted my life."

• 18:25Guy Raz?

  I've 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, even if it's scary?"

• 18:36Speaker 01

  I think, to be fair, the young, this is where the younger you are, the less dangerous that slope is, you know, 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.

• 19:00Guy Raz?

  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 with 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.

• 19:22Speaker 01

  I 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.

• 19:47Guy Raz?

  That pressure, yes.

• 19:47Speaker 01

  I certainly don't wish that on anyone, but yeah.

• 19:50Guy Raz?

  Right. 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.

• 20:10Speaker 01

  Yeah.

• 20:11Guy Raz?

  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, he 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 and Louisiana. He was, he was like a scholarship kid. His family were immigrants. Like, he had nothing. And I remember him telling me the story about, you know, explaining to his mom, you know, that he was leaving this lucrative job and how stressful that was.

• 20:55Speaker 01

  Yeah, you can imagine my mother, who, you know, when I told her I'd quit my job, you know, I still, her first word was, "What?"

• 21:04Speaker 05

  And 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. You know, not only was there a monetary aspect to it, there was probably a shame aspect to this as well. That, that, you know, was, was, was hard.

• 21:26Guy Raz?

  I mean, and it's not only like, and this story is, comes up oftentimes with, 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, my parents didn't know where it was. They, I didn't grow up listening to it. And I remember just feeling like, God, they, this, I, I thought it was a big deal, you know, but they really, um, when their friends would ask, they say, is we're in a radio station in Washington DC. So I, I, I know the feeling.

• 21:59Speaker 01

  I, I mean, I went and made doorbells, so I, I know the feeling too, which is, you know, it's, it's, it's easy to forget that when like, you know, when you started with a doorbell, that 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.

• 22:28Guy Raz?

  You know, whatever we're talking about, whether it's a piece of apparel or food, we really get into the, 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.

• 22:43Speaker 06

  I would do a peanut butter and grape jelly, peanut butter and strawberry jelly, and I mixed them together in the food processor. So very quickly I had 30 or 40 different jars.

• 22:53Guy Raz?

  We did Justin's 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, you know, all the stuff and then you want to add flavors.

• 23:11Speaker 06

  Let's just say you wanted to make honey peanut butter. It sounds simple, three ingredients.

• 23:15Guy Raz?

  Right.

• 23:16Speaker 06

  Peanuts, honey and salt.

• 23:17Guy Raz?

  Right.

• 23:18Speaker 06

  All right, well, what type of peanuts do I want to use? Cause at the store here, there's Valencia peanuts, there's Virginia peanuts, there's Spanish peanuts.

• 23:25Guy Raz?

  Right.

• 23:25Speaker 06

  There's runner peanuts. And then do I want to?

• 23:28Speaker 01

  And so it's weird, cause you're looking at it from the, like, you're listening to him and saying the product. I'm listening to him and I'm saying, just like I looked like, and again, I didn't really know it at the time, but home security. And I figured out a way to get the thin edge of the wedge. Like, I figured out a way to like slice razor into home security. He figured his way out to get into the peanut butter business. Like, all these peanut butters, this huge market, and he figured out how to like, get his wedge in there and then, and now it's a huge peanut butter business.

• 23:57Guy Raz?

  One of the things that we really grind in on is the early prototypes. And one, I remember a conversation I had, we talked to Eileen Fisher, who is an amazing fashion designer, and she was and is super introverted. And she, you know, she just wanted to make very simple, elegant clothing for women. She was not super experienced, it's the early 80s. And, you know, she decided to go to a trade show and she was, she just felt so unprepared for what she was about to face.

• 24:31Speaker 07

  So I thought, well, I will, I committed to a booth, a small section, just like a one wall of a booth.

• 24:38Guy Raz?

  You thought, I'm gonna go there and show my clothes there?

• 24:41Speaker 07

  I'm gonna go there and I'm gonna show my clothes, right.

• 24:43Guy Raz?

  And did you have?

• 24:45Speaker 07

  No, I had no clothes, I had.

• 24:46Guy Raz?

  Did you have a name for the company?

• 24:47Speaker 07

  No, I had no name, I had no clothes, I had no fabric, I had no styles, I had nothing.

• 24:54Guy Raz?

  You had designs though, right?

• 24:55Speaker 07

  No, don't get carried away now, it wasn't really a fashion line to start out, it was four garments.

• 24:59Guy Raz?

  Well, so what did you end up calling it for that, for that show?

• 25:02Speaker 07

  So I called it Eileen Fisher, because I couldn't think of anything else. And I, and I was so freaked out. The first day, I literally couldn't speak. I just stood there. People would ask me questions like, how much does it cost? What's the style number? And I like froze and.

• 25:19Guy Raz?

  I just want to give you a hug and say, it's gonna be okay, Eileen, it's gonna be okay.

• 25:24Speaker 07

  I was like a deer in headlights.

• 25:26Guy Raz?

  Jamie, did you remember feeling that way?

• 25:28Speaker 01

  Oh, I mean, like, I remember I went to CES and I took my wife's Jeep and packed a booth that we made out of all the boxes that we taped up on the wall that we got a, and you know, I always like the charity booth, they like gave a booth to like this poor company that like couldn't make it, the CES gives you in like the back corner. And yeah.

• 25:47Guy Raz?

  And like the basement, like, like three floors down and like the, the Venetian hotel.

• 25:51Speaker 01

  It's so embarrassing, like, because you do have friends that you know that work in industry that like come over, they're like, oh, you're doing really well, Jamie. And it's like, you're like in this like corner thing with like, it's dark and it's, it's horrible. So, you know, to your, you said like, I, I wish I could just give you a hug. When people ask me like, what would you have done differently? It's not what I would have done differently, I just wish someone had come to me and said, it's gonna be okay. That's the, it is what you want. You want a guy hug, like when you're there and you're like in this thing and it's like, you're just fighting through it because you're, you gotta put your face on. I mean, these people are coming over. And it's just so hard to keep that face of like, I'm, I'm doing great.

• 26:35Speaker 01

  And it's like, you know, you're a total loser, like you can, it's obvious.

• 26:39Guy Raz?

  Yeah. Well, and I hear you, you get emotional and I, and I really appreciate that. And you did in our conversation too, because you feel it, you remember it, you know? And it's like, if somebody was there, you're just like, it would have been so helpful.

• 26:53Speaker 01

  Yeah, like, I want to go hug her. Like, I totally know that feeling, it's like just awful, like it does bring it back. It's like all this stuff. And it is emotional, it's an emotional journey.

• 27:04Guy Raz?

  When we come back in just a moment, more lessons, stories and ideas from 10 years of this show. I'm Guy Raz and you're listening to How I Built This. Stay with us.

• 27:19Guy Raz?

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• 28:02Guy Raz?

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• 28:44Guy Raz?

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• 29:26Guy Raz?

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• 29:50Speaker 08

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• 30:35Speaker 09

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• 30:58Guy Raz?

  Hey, welcome back to How I Built This. I'm Guy Raz. And me and Jamie Simonoff are looking back at some of the highlights from the past 10 years of the show. So, one of our earliest episodes was with Mike Krieger and Kevin Systrom, the founders of Instagram. And they talked about how when they first put it out into the world, they were totally overwhelmed.

• 31:18Speaker 01

  Before you knew it, we actually had overloaded our system, and it was a very small, naive system. It was a single computer in a co-location space somewhere in LA.

• 31:26Guy Raz?

  Everything was on one computer?

• 31:28Speaker 01

  Yeah, it was, it was nothing more exhilarating than seeing all those people stream in, and nothing more crushing than then seeing, you know, people posting on Twitter or on their blogs and saying like, oh, another startup that doesn't know how to scale, like, oh, like, so clowny. We were both, I mean, at that point, like, running on zero sleep for two days, devastated. And I was like, this is it. We built this great thing, and we totally messed it up.

• 31:50Guy Raz?

  Jamie, you know, you had this situation where you had sent rings to people, and they were failing in their home. Like, they were trying to install them, and they were failing.

• 31:58Speaker 01

  Oh, yeah.

• 31:59Guy Raz?

  Yeah. I mean, but that's a lot of, in a lot of cases, people think that's it. It's over. We are, we are done. And similar story, by the way, with Squarespace, who we had on the show years ago. He had to, like, drive up to a server in Delaware and fix it because it had gone down. And like, people's websites, this is early days of Squarespace, people couldn't, their websites went down.

• 32:20Speaker 01

  The crazy thing is, there is a balance, though, of like, you heard about Instagram more because it was crashing. Now, if they never got it fixed, people would just sort of stop using it. But there is a, sometimes there is this weird thing that, like, some of that patina and those bumpy things do, like, Squarespace. Like, I remember hearing about Squarespace going down, but also like, oh, there's a place that I can build a website.

• 32:41Guy Raz?

  Right. Because Instagram initially was like for, they put it out to journalists and designers and photographers. But then people hear about this failing, you know, server, and they're like, wait, what is this thing? You can get pictures on your phone, and they look cool? I want that.

• 32:54Speaker 01

  Yeah. It's almost interesting, if you could go back and see if they launched it, and it worked perfect, if it would have actually taken off the way it did, without the sort of, you know, bumps.

• 33:05Guy Raz?

  It's a good lesson about failure, which I really, I hope people hear in every episode, that there are moments of failure, and even longer than moments of failure. And you have to experience that failure or setbacks in order to understand how to make something that works. And one of the best stories we told about failure was, was the story of James Dyson, of course, famously known for the Dyson vacuum cleaner and many other things. And he was already in his early 40s, you know, when he was still experimenting with how to make a bagless vacuum cleaner. He spent five years on this thing, and he built thousands of prototypes in his backyard shed.

• 33:43Speaker 10

  So, and I've learned that with developing new technology, that when you feel like giving up, it's precisely the point everybody else gives up. So, it's at that point that you must put in extra effort.

• 33:56Speaker 01

  So, it's funny, you don't know this, but that episode came out early 2018, and it was when I was doing the Amazon deal to buy Ring. And this was, you know, before it was announced. And there's a term called pencils down in a deal, when sort of, like, a side decides they're going to walk away. And Amazon, that week, went pencils down on us. And my president, Leila Rui, said, Jamie, you need to just get out of the office, and like, go for runs, and like, we'll figure this out. And that episode came out, and I can still remember being on a run, listening to it, and thinking, like, he was my hero. James Dyson was like, my hero.

• 34:37Guy Raz?

  Well, I did not know this story. That's amazing to hear. And came out, I mean, that's-

• 34:41Speaker 01

  And Dyson was someone who I looked at for Ring as, like, to build the brand. I mean, obviously not copying, but like, you know, how he put himself out there. And I did the same thing. Like, I used sort of James Dyson, I've never met him, but I kind of mimicked a lot of things that I saw him do. I've always looked up to it.

• 34:58Guy Raz?

  Hey, sometimes things happen for a reason. It came out right when you needed it.

• 35:02Speaker 01

  Yeah.

• 35:02Guy Raz?

  Um, one of the things, and it's, you hear Dyson's story, you hear it, and even Howard Schultz, everyone's stories, how scrappy people were at the beginning of their careers, and they're building this brand out. They had to be scrappy, because nobody took them seriously. Nobody would take their phone calls, you know? And one of the, actually, it was our first episode of How I Built This, back in 2016, was with Sarah Blakely, the founder of Spanx. And Sarah, she comes up with this product, this undergarment, this shapewear, that is still, it's, she has to introduce this idea to people, and she's just her. And, but she has a prototype, and she finally gets through to a buyer at Neiman Marcus. And, and so she flies down to Dallas to meet with the buyer.

• 35:46Speaker 11

  In the middle of my meeting with her, I could tell I was losing her, and I got, I just knew it was my one shot. So, I said, you know what, Diane, will you come with me to the bathroom? I want to show you my own product before and after. And she, she said, okay. And she walked down the hall with me, and I went in the stall, and I had on my cream pants that were the reason I invented this, without Spanx on. And then I went in the stall and put Spanx on underneath, and came out. And she looked at me, and she goes, wow, I get it. It's brilliant. And she said, I'm going to place an order, and I'm going to put it in seven stores and see how it goes.

• 36:20Guy Raz?

  And, and at that point, you know, like, a lot of people listening might think, oh, you're set. You got Neiman Marcus. But not really, right? Like, that is not a guarantee that you were going to make it.

• 36:30Speaker 11

  Oh, my gosh. That is the biggest mistake that entrepreneurs make. That is when the work begins. First of all, I paid people, basically friends, to go buy the product and create a buzz about it, because I was like, you know, I got to have these things move off the shelf, or the buyer's not going to give me any, any more chance.

• 36:47Guy Raz?

  Wait, you paid people to buy them?

• 36:50Speaker 11

  Yes. And called friends that I hadn't even spoken to since 4th grade, and, you know, kind of like, hi, it's Sarah, remember me from 4th grade? Do you mind going to the store and buying Spanx, and I'll send you a check?

• 37:01Guy Raz?

  Did you ever get people to, to order rings like that?

• 37:06Speaker 01

  No comment, Guy. I take the Fifth Amendment. Sorry, I'm not testifying. Yeah, of course I did. I mean, God, that clip is just, it's just founder. Like, that's just every part of that, like, from setting up the meeting, to being in the meeting, to showing it, to getting in the store, to realize, it's like, every part of that clip, there's like, 30 things you can learn from that clip, but they all come down to, like, founder. Like, nothing was going to stop Sarah from succeeding. That's it.

• 37:35Guy Raz?

  And she, by the way, later told the story about how she would go into Neiman Marcus, and she would find the Spanx alongside pantyhose, whatever, and she would remove them, and put them in a little display she would bring next to the cash register, like, when no one was looking. Or they would just assume that she was, you know, allowed to do that. She was-

• 37:53Speaker 01

  And, and by the way, when you're small, you can get away with anything. I mean, but don't, like, break the law. But like, but like, going into a store and like, moving your product, like, you're small. Like, it's fine. Like, I can't do that today with Ring. Like, I get a lot of trouble. But like-

• 38:06Guy Raz?

  Yeah.

• 38:07Speaker 01

  Yeah.

• 38:07Guy Raz?

  I mean, that's the thing. Like, you have to be creative and scrappy. A story that always comes back to me about, like, just really thinking creatively about a product was Sun Bum, which is, of course, sunscreen. And Tom Ranks, he was based in Grand Rapids, Michigan, right? A freezing cold place, not something you think about when you think about sunscreen. So, he didn't want to put, like, you know, Grand Rapids, Michigan on the bottle, you know, as, as the, the address or the place where it was coming from. He wanted to put somewhere where people would think, oh, that makes sense. Sun Bum is from this place. So, he decided to basically set up the brand in Cocoa Beach, Florida.

• 38:48Speaker 12

  Cocoa Beach just sounded like a good place for a sunscreen company, right?

• 38:52Guy Raz?

  Yeah.

• 38:52Speaker 12

  Like, Cocoa Beach.

• 38:53Guy Raz?

  Exactly. And that sounded good. So, we liked that. So, we got a P.O. box in

• 38:57Speaker 12

  Cocoa Beach. And then we, you know, all the calls were getting transferred up, you know? And then we, yeah, we had a-

• 39:04Guy Raz?

  You mean the, the customer service calls?

• 39:06Speaker 12

  Yeah, customer service calls.

• 39:07Guy Raz?

  They were getting transferred up to Grand Rapids?

• 39:08Speaker 12

  To Grand Rapids, yeah.

• 39:10Guy Raz?

  Like, in the middle of winter?

• 39:11Speaker 12

  Yes. So, we'd be on the phone. I, you know, nobody ever lied. But we, we did say, you know, if they call and ask how the weather is, you know, just tell them it's unbelievable, if it's snowing outside or whatever, because then you're not lying. It's unbelievable, right? And they'll think you mean unbelievably good, but it's unbelievably bad.

• 39:27Speaker 01

  I think it just comes down to, there's this, like, weird line that we get close to as entrepreneurs, of this reality distortion. And I think we all have it. And I love that he said, like, we didn't lie, but they also certainly didn't try to, like, tell them they were in Grand Rapids, Michigan, freezing, their tushies off.

• 39:45Guy Raz?

  One of the, one of the stories that we have told, actually, more often than, than people may realize, are of products that were not inventing something new. It was a new way of introducing the product to people. Things that people would say, oh, that's a saturated market. Why do you want to get into that? And one of the best examples of this was, Mike Cesario founded a water brand. And when he entered that space, water was, it still is to some extent, totally dominated by, you know, four or five multinationals. And what he realized was that there was a wormhole. There was an opportunity to take this thing that everybody drank, and, you know, lots of people buy, and turn it into something, at least in someone's mind, that was much more interesting.

• 40:29Speaker 13

  A beverage called Liquid Death, like, when I finally decided, hey, I want this thing to look like a beer. Like, that was kind of the concept. I remember calling one of my best friends and telling them, I'm like, hey, I want to put water in cans that look like cheap beer. And that felt right to me, because I'm like, you know, everybody wants stuff they're not supposed to have. You know, it's like, they say, hey, if you want teens to think something's cool, you actually market it to people in their 20s. So then, but from like, a naming perspective, I thought some of the craft beers had some of the most interesting, like, brand names. There was like a Skull Crusher IPA. There was like arrogant bastard ale.

• 41:05Guy Raz?

  Yeah, yeah.

• 41:07Speaker 13

  And the only chance this has at survival is it has to be something that people naturally want to share on social. And that's where it's like, you literally start trying to think of, what's the craziest thing you could think of? Like, start there.

• 41:19Guy Raz?

  Yeah.

• 41:19Speaker 13

  Do the opposite of what you think you should do. But I remember thinking, like, Liquid Death, like, there is no chance someone's not sharing that if they see that in a store.

• 41:30Guy Raz?

  It's a simple product and a brilliant way of thinking about it. Because I remember when I first saw Liquid Death in the store, I thought it was malt liquor. I didn't realize it was water until I looked at them. But I went to the buy, because I started at Whole Foods and I was like, why is Whole Foods selling tallboys of beer or malt liquor? And then I looked at it and said, you know, mountain spring water. It's just so weird.

• 41:52Speaker 01

  To me, it's an invention. Like, he invented this brand differentiator that let them cut through this giant shelf of just all these waters that are already out there. But I just think it's like, there's something like about that, not just product, but like invention.

• 42:07Guy Raz?

  One of the things that we get asked a lot about is money. You know, people say, I don't have money. I don't, I'm not wealthy. I don't have access to parents who have money. And the reality is, actually, most people who have been on How I Built This don't either. Money is always really challenging. Where do you get it from? Who do you ask? And I remember we interviewed Gary Hershberg. He's the founder of Stonyfield Yogurt, and also a pioneer, one of the pioneers in sort of natural foods. And this is a fantastic episode, just full of failure. If you want to hear a great failure episode that, of course, resulted in the success of the end, this is the one to listen to. And, you know, early on, he raised money from friends and family.

• 42:52Guy Raz?

  And he, you know, he would be calling his mother-in-law for loans, oftentimes while his, his wife was asleep nearby, and it was hard for him.

• 43:04Speaker 14

  And by this point, it was a half a million dollar business. And I never had cash in the bank that night before payroll, never. Just, this became our way of life. Thinking Meg was asleep in our bedroom, which was about 50 feet from my office, I would, on many occasions, tiptoe over to the office to call my mother-in-law, to have a chat, to see if I could borrow another 3,500 or 2,500 to make ends meet. And eventually, Meg got on to this. And one night, I heard the click, click of call waiting on my mother-in-law's phone. And Meg was calling from the house to say, Mom, don't do this.

• 43:39Guy Raz?

  Wait, your wife was telling her mom not to lend you money for the business?

• 43:44Speaker 14

  Right.

• 43:45Guy Raz?

  Because she didn't have confidence in it?

• 43:46Speaker 14

  Well, look, she's living in a nightmare. I mean, she saw how crazy it was. I mean, we had chimney fires. We had, the well pump would go out, the, the power would, I mean, we're on this hilltop farm, a long way from anywhere.

• 43:58Guy Raz?

  Was Meg saying to you, let's just ditch this thing, let's bag it? I mean, or did she, because it sounds like she, maybe she didn't believe in it.

• 44:04Speaker 14

  Well, she had no reason to believe in it. It was insane.

• 44:07Guy Raz?

  It was insane. They were making really great tasting yogurt, but it was a failing business for many, many, many years. And part of this process is just the psychological weight of knowing that all these people, whether you know them personally, or their family, or their distant relatives, or their friends of friends of friends who happen to have, you know, $5,000 or whatever, that not only can you be held accountable for that forever, but like, the person that introduced you to them is always going to be like, I introduced you and you just like, lost all their money.

• 44:40Speaker 01

  Yeah. And the thing I think he doesn't talk about in there, but he infers, is like, you know, it's like, she says, like, she would have loved to shut it down. I don't think that was an option at that point. Like, my guess is, shutting down at that moment, they would have probably eviscerated everyone's capital, including their own. So like, you do get to this point where like, there's a one-way street. Like, you either get out of this one-way street by being successful, which means taking, you know, grabbing some more money along the way, or you're dead.

• 45:09Guy Raz?

  And, you know, we've come across this story so many times with founders who are so, who've built businesses that are so well-known, that you're like, how could people have said no to it? But of course, in context, it makes sense. A lot of these ideas were outlandish, or they didn't make sense, or there was no track record. And this was the case with, with Whole Foods. In the late 80s, John Mackey and his co-founders, they opened a few stores around Austin. They were like, what you would think of as like a 70s food co-op with like, bulk bins. But they were doing well, and they were looking to raise money to expand it out, the concept out further.

• 45:43Speaker 15

  We hired a banker, and we began to try to raise venture capital money. And we got rejected again, and again, and again. And we, trying to talk to the venture capitalists, they just couldn't get what we were doing. I mean, one guy who turned me down, he said to me, he said, you know, John, I see you got a really good business here, but it looks to me like, I looked at all the stores, and you're just a bunch of hippies, and you're just selling food to other hippies. And I don't think that's a very big market.

• 46:10Guy Raz?

  I mean, he wasn't wrong, right? That's what it was? Of course, it turns out that hippies were, were baby boomers, and that was the like, biggest potential market, you know, in modern history. This is, by the way, this is all, I'll play another clip. This is also the story, so believe it or not, with Airbnb. I mean, they had a prototype product that they had out there, and they had a little bit of traction. And so they were like, okay, let's go.

• 46:35Speaker 16

  We thought, well, this is a great time to talk to investors. Our numbers are up. Look, it's actually working. We have stories that we can share. We've got press. We get introduced to 20 investors in Silicon Valley. 10 of them replied to our email. Five of them met us for coffee. Zero invested in us.

• 46:54Guy Raz?

  Wow.

• 46:55Speaker 16

  It was completely demoralizing. Like, 2008 was the worst year of my life.

• 46:59Guy Raz?

  Like, Jamie, you're listening to that, you're like, oh, my God, I wish I was on that email list, right?

• 47:03Speaker 01

  But you know, but I probably would have, sadly, I probably would have said the same thing. Like, it's like, you, you, that's what makes it so hard being, by the way, it's hard being on the other side, because even though you believe in it, you still question when someone intelligent says to you, like, this thing can expand. You're like, you're not on to something. Like, it does, you do say like, oh, well, maybe I am crazy. So like, I heard it with, you know, with Ring, and you see it with all these companies. I mean, it's, it's amazing, the doubt that happens. And that's what makes it so hard to build something great.

• 47:35Guy Raz?

  And Mark Cuban, I think, he turned down an opportunity to invest with Uber. And, you know, he's kind of funded himself for that. I think the point of this is also to remind people that like, when people turn you down, it doesn't necessarily invalidate the idea. And when people give you money, it can feel validating, but the other side is that it may not always be validating. The point is, is that when you're starting a business and you're, you want to raise money, you have to expect that, if you're lucky, two to five people out of 100 will invest. And so 95% no rate is, is not invalidation. It's not saying your idea sucks.

• 48:13Speaker 01

  I would say it's kind of the opposite, which is that the businesses that have the easiest time raising money are usually the worst, and the ones that have the hardest time are usually the best. Now, of course, there's like, different things in those, but it's, and it makes sense, because real invention, real sort of market-changing things are not obvious.

• 48:33Guy Raz?

  Yeah. And the, again, like, knowing that you've got to go to a lot of places is part of the game, right? We talked to Kathy Hughes, who founded a radio network called Urban One back in the late 70s, and grew it to the largest black-owned radio network in America. An incredible entrepreneur, an amazing story. She was a single mom, and she really built this incredible media empire. And she was trying to raise a million dollars in the late 70s to buy a radio station. And that was really hard. I mean, she's, she's a black woman with no real background in business. She'd worked at radio stations, and she was ambitious and smart, but, you know, really hard. She had no collateral.

• 49:18Guy Raz?

  She went to 32 banks, and every single one of them said no. And finally, she found the 33rd bank. She found a banker there, who happened to be a woman as well, who agreed to do the loan.

• 49:30Speaker 17

  She said yes, and I just kept, by now, my presentation should have been taught in colleges, because it was flawless. I mean, after 32 times of perfecting it, okay, I mean, I was, I should have gotten an Academy Award, I was so good at it. I kept convincing her. And she said something to me that I teach all my salespeople. She said, please, don't sell past the close. And I never forgot that, because that was another one of those slap in the faces. I was like, wow, she's absolutely correct. She said yes. I couldn't believe she had said yes.

• 50:04Guy Raz?

  When she said yes, you kept selling her on it?

• 50:05Speaker 17

  Yeah, I kept convincing her, right. Exactly. That's correct. I kept, right. I kept trying to convince her. And she said, Ms. Hughes, let me give you a little advice, never sell past the close.

• 50:15Speaker 01

  You know, sometimes when people hear this, it's like, oh, I have to talk to 33 banks. It's like, no, she was going to talk to 1,000 banks. Like, she was never going to stop until someone said yes. She didn't know after 32 that 33 was going to say yes. She just wasn't going to stop.

• 50:32Guy Raz?

  When we come back in just a moment, more from the past 10 years of the show, including that question that some love, some hate. Is it luck, or is it skill? Stay with us. I'm Guy Raz, and you're listening to How I Built This.

• 51:04Guy Raz?

  Hey, welcome back to the 10 year anniversary episode of How I Built This. And I've been listening back to some of the highlights with our friend Jamie Siminoff from Ring. And you might have noticed that we're leaning pretty heavily on the early years of founding a business and, you know, all those moments of difficulty and doubt and failure. But as Jamie and I were talking about that, he was saying, you know, it's good that we're telling stories about how tough it can be, because it's very real.

• 51:33Speaker 01

  It's part of the problem of like, especially these larger companies, these PR departments is like, we've just sort of like whitewashed reality. And it's not good for like, mental health, because people are sitting out there alone and trying to do this. And they're real. And like, when they hear someone who's just crushing everything and great at everything and perfect, it's like, you do want to hear like, that James Dyson almost gave up. And that all these people that you look up to that like, you've done these amazing interviews, these people that you're like, listen, you're like, oh, they're, I'm not different. I just, I'm just not successful, but I'm not different.

• 52:06Guy Raz?

  Yeah. You know, one of the reasons why we focus on the challenges and just the grind is because I want people to understand that there's a huge price that you have to pay personally and professionally. And there's also the physical toll on your body and your health. And that's something that when I talk privately to founders and to groups, I'm always saying, that's the only thing that you really have.

• 52:31Speaker 01

  Yeah.

• 52:32Guy Raz?

  And we did the story of Banana Republic, which is a great story. Mel and Patricia Ziegler founded this, or actually Marin County, here in Northern California. You know, they were making a lot of the clothes themselves. And then they start to make this, what became this iconic catalog to promote it, which some people remember in the 80s, it had like, safari themed and jungle themed. It was really cool. But they were working nonstop at the time.

• 52:55Speaker 18

  I remember going to the East, or San Francisco, to the printer to put out our latest catalog. And I hadn't, I hadn't slept in like, three nights, I think I was just up around the clock. And I was driving home, across the Golden Gate Bridge. And all of a sudden, I hear this honk. I wake up and realize I've veered into the oncoming traffic on the bridge.

• 53:20Guy Raz?

  You were falling asleep.

• 53:20Speaker 18

  I was falling asleep. I was so sleep starved. And I went home and I just broke down.

• 53:26Guy Raz?

  The good news, Jamie, is that today, there is a physical barrier on the Golden Gate Bridge that I, I use all the time. And so you can't, you could crash into a barrier, not into an oncoming traffic.

• 53:37Speaker 01

  You don't use the barrier all the time. You use the Golden Gate Bridge.

• 53:39Guy Raz?

  I use the bridge all the time. But if you watch, if you watch like, a Dirty Harry movie, or like, you know, a Steve McQueen movie from the 70s, when they show that people are driving over the bridge, there was no barrier. It was just a painted line in the middle of the Golden Gate Bridge.

• 53:55Speaker 01

  Yeah. I mean, the only tool I've found, because you do need some mechanism or something to keep yourself healthy, is I tried to run every day. Like, that 30, 40 minutes a day, you have to take that time out, because you stop making good decisions. And that's usually like, failure is, it's us. Like, it is like, we started this, like, it's, it's on us. And so the failure usually comes down to making a bad decision, not working harder.

• 54:19Guy Raz?

  Yeah. You know, the idea of like, being in this black tunnel, this tunnel with no light, and then starting to see the light. And, and, you know, as we talked about, it can be years before that happens. I remember we, we had Hamdi Ulukaya on the show a few years ago, founder of Chobani. Another amazing story, I know I say this about every story, but really, they are.

• 54:42Speaker 01

  They are, they're all amazing.

• 54:44Guy Raz?

  And he, you know, an immigrant from Turkey, he spoke no English, like, he just started making yogurt. He, he was able to finance this dilapidated yogurt factory that had been sitting there vacant in upstate New York, and got a really good deal on a loan. And but it was a real struggle for many years. And also to convince people to eat Greek yogurt, Greek style yogurt. There were some brands, but Chobani, it brought it to like, the masses in regular supermarkets, you know. And, and I remember him talking about like, after like, five, six years, that he starts to see some of that light as they start to sell, they start to sell their product.

• 55:25Speaker 19

  And it feels like I'm in the soccer game. I'm in the middle of the soccer game, and I love it. And I'm into this game in such a massive way. And I'm completely elevated. First time in my life, I feel like things are coming out of my being that I didn't even realize it existed. It's like, I'm wondering what is behind that mountain, what is behind that mountain. I have this enormous amount of curiosity. And I feel alive.

• 55:53Guy Raz?

  You feel alive. Maybe it's a ray of light, maybe it's a distant light coming through a part of that tunnel.

• 55:59Speaker 01

  And it is, it's just these little boosts that you do need along the way. And it is, you're in that tunnel, you maybe you see like, just like, it looks like it's getting a little, like, little sort of brighter ahead. Like, it's not, it's not, you don't know if it's the exit, but like, it like, at least there's like, maybe there's an escape hatch or something.

• 56:15Guy Raz?

  Yeah. Yeah. You know, Jamie, I want to get back to something that, that we talked about a little earlier, which is raising money, right? Because for a lot of founders, that need just never goes away. Like, it can be an ongoing part of the story, right? Because the company keeps growing, and then it just needs more and more cash. And we've had episodes like the story of Serena and Lily, the furniture maker, where, you know, the two founders, they had to raise a fair amount of money, because furniture production is cash intensive. And they were in the Bay Area, where investors were used to, the investors they were talking to were used to just, you know, funding software. So a lot of their money, they were taking from traditional VC, who wanted growth, growth, growth. But it was challenging when they weren't

• 56:59Guy Raz?

  growing, and they needed more money. And the VCs were like, well, we gave you the money. So they found themselves in a position where they had to bring on another investor who unfortunately had very different goals.

• 57:11Speaker 20

  We still, because of this cash incinerator of this growing company, we brought in more of a private equity type of investor on the now this third major round.

• 57:24Guy Raz?

  Okay.

• 57:24Speaker 20

  And so they wanted profitability. They wanted slowing down the growth.

• 57:32Guy Raz?

  I mean, could you have done that? Could you say, we got to do this, we got to conserve cash, we're going to slow down growth? Or was that just not an option?

• 57:41Speaker 20

  I think the answer kind of resides in the middle. More people around the table were more in favor of the growth.

• 57:48Guy Raz?

  And this, at the time, that was the model, grow, just grow, grow, grow. Because you were not profitable yet, I imagine.

• 57:53Speaker 20

  No, we were slow growers.

• 57:56Speaker 01

  I mean, the hard part is, you got to raise money. Like, the company will go out of business without money. So sometimes, you go out there, and it's like, it's nice to say that you want people to have conviction. But at the end of the day, like, I would have taken Satan's money for Ring, you know, if I had to, like, because I needed money. Like, I do love when she said cash incinerator, because people just underestimate, like, a growing business looks so good on the outside. But like, when you're in the physical hardware business, which, you know, they were in a physical business, growth like that is just, it is a cash incinerator.

• 58:29Guy Raz?

  And sometimes, it's not always critical to scale, scale, scale, scale. You know, a really successful, small business that generates, you know, $4 million in, in sales a year, but is totally profitable, and the founders are walking away with $1 million. That is a better business than, you know, a huge, you know, multimillion dollar business that has never made a profit.

• 58:53Speaker 01

  I mean, a lot of times, the slower number two makes more money. I mean, the bigger number one looks like they made more money, but actually, the slower number two, like, the people actually make more money, because, yeah, less dilution, all of these things.

• 59:04Guy Raz?

  Yeah. And so there are some brands that we've had on the show that did not take any outside investment. One of the stories we told was about a brand called Title IX, founded by Missy Park. It's a women's sports apparel brand. She was a collegiate athlete in the 70s. And so she was inspired to create a brand for female athletes. And so she never raised money, and part because she wasn't so focused on like, growing, growing, growing, 500, 10, you know, 1,000%. She talked about this idea that, you know, you can have a really great, sustainable business, like, in her case apparel, that didn't have to be as big as Lululemon, or, or Athleta, or another brand, like, that is okay.

• 59:45Speaker 21

  For me, I'm just like, I'm going to just stay in the game here. I'm going to kind of keep hitting little singles. And I think it's, it kind of goes to basically, a business philosophy is just, if you hit singles, Which we do and we're good at. You're not going to hit a grand slam.

• 1:00:01Guy Raz?

  Yeah.

• 1:00:02Speaker 21

  And that's just, you need to make your peace with that. And I think I would take the staying in the game of singles to striking out a whole bunch and every once in a while, getting a grand slam.

• 1:00:13Speaker 01

  I think the most important thing is knowing who you are. Because if you're going to be singles, don't raise big venture capital money because it's going to force you to have a company that does singles, that's going to try to hit grand slams. That's bad. And on the flip side, if you're going to go for the grand slam, raise all the money. Like, I see people try to go for grand slams, but hold back on the raise to try to maximize their ownership. It's better to own 2% of a $100 billion company than 100% of a tiny thing.

• 1:00:39Guy Raz?

  Yeah.

• 1:00:40Speaker 01

  But she owned 100% of a, probably a deck of, you know, tens of millions of dollar business and like, that's still great.

• 1:00:46Guy Raz?

  A dilemma in some cases, and in some cases, it's not a dilemma, is whether to sell your company. And in many cases, it works out great. It worked out great for you. You're still at Ring, of course. But sometimes it's really hard. And we've had founders who sold their brands and had a hard time finding themselves after because it was their identity. It was their team, the camaraderie, you know, it was like going in every day and then it was gone. I remember we, we had Bobby Brown on the show and of course, you know, she started her eponymous cosmetics company in the early 90s. And she sold it just a few years after the brand was launched to Estee Lauder. And she had stayed on, she stayed on as the chief creative officer for 25 years after the sale.

• 1:01:30Guy Raz?

  But, you know, towards the end, she talked about how it got harder and harder for her to be at a big company. And so she had, she had to decide what to do.

• 1:01:39Speaker 22

  It got so big. The company got so big. The corporation got so big. They bought so many other companies. It was growing. It was huge. I am not a follow the leader kind of person. I am the leader, okay? I can't help it. And if I see things not working where it makes sense to me and wasting energy and time, I don't like it. And I like to try new things and invent new things. So, yeah, it was always a struggle. And so then the last couple of years were really tough.

• 1:02:09Guy Raz?

  Like what happened?

• 1:02:11Speaker 22

  Oh, my God. There was just, you know, they start, and I used to hire, approve and hire and interview every person that walked in that brand.

• 1:02:18Guy Raz?

  Sure.

• 1:02:19Speaker 22

  And then I didn't anymore. And all of a sudden, there were people working on my brand that I never met before and that I might not have hired. And, you know, it was a struggle. And I tried to let go of the details, but then I realized the details were what makes the company so special.

• 1:02:37Guy Raz?

  Jamie, what do you think? It was a different story for you. You hadn't a different experience. You were, obviously you were so, it was overwhelming to sell the, the brand and exciting. And you stayed on.

• 1:02:47Speaker 01

  Yeah. And I, it's like, there's, it's one of these things, there's like, there's no right answer. You know, should you sell? Should you not sell? In some ways, the fact that I'm still here just says that I'm a super frustrated person who can't find something they love as much as the business they started. Like, I love Ring.

• 1:03:04Guy Raz?

  I asked Jensen Huang of Nvidia, you know, he famously went through many years of just being in a trough. And their stock price was in the dumps. Their investors were frustrated because they were making a computer chip for video games. And he saw potential in that to do many, many different things, things that, that he couldn't imagine yet, but he knew that there would be something to it. And so he was investing a lot of money. This is like 2005, 6, 7, you know, when, the idea of AI is, it's on the minds of like, science fiction writers and some thinkers, but it wasn't practical yet.

• 1:03:46Guy Raz?

  And, you know, it was just, it was years of dealing with a failing business until, of course, it, it became the most valuable business in human history. But that happened only in the last five or six years. So I asked him, I said, you know, would you, knowing, you know, what you know, knowing about the struggle, would you do it again? And, and this is what he said.

• 1:04:07Speaker 23

  When somebody asked me, would I do this again? If your question is, knowing how Nvidia turned out.

• 1:04:14Guy Raz?

  Yeah.

• 1:04:15Speaker 23

  Knowing the contribution we've made to the world, all of the benefits that we have accrued as a result of our success. Do I love those things? The answer is yes. But that wasn't the question.

• 1:04:27Guy Raz?

  Right.

• 1:04:28Speaker 23

  You know? The question is, suppose I knew everything then that I now know, how hard it is and all of the pain and suffering and all the embarrassment and humiliation and all the setbacks and you compress all of that and you just told that 30-year-old kid, listen, this is going to take a lot longer than you think and you're going to be the person who delivers most of the most horrific financial return news that anybody's ever explained, you know, so on and so forth. You'll be going out of business. You'll be, you have to lay people off. Would you start again? The answer, absolutely not.

• 1:05:06Guy Raz?

  I love that. Because you think of this guy, you know, Jensen, and, and he talked about the sacrifices. He didn't get to see his kids growing and missed a lot. And he got quite emotional talking about that, missing out on, you know, sports games and birthdays and, you know, there was a lot that he didn't get to, to do and to see.

• 1:05:25Speaker 01

  And I, I think, you know, it's an incredible story of someone who like, just was so convicted without knowing what that tunnel was going to end like. I mean, like to your point of AI, like, he was building stuff that other things had to happen in order for him to be successful that no one knew were going to for sure happen, but he believed it would.

• 1:05:41Guy Raz?

  Yeah.

• 1:05:42Speaker 01

  I do love his honesty of like, if I really actually saw it, like, and not knowing it was going to be successful, like, he probably would say no because it was just too hard.

• 1:05:49Guy Raz?

  There's so much wisdom on the show from different founders and in very diverse ways. You know, like we had, I remember Danny Meyer of Shake Shack, you know, talking about, he's, he's the founder of some amazing restaurants and then of course Shake Shack. And he talked about, in his view, what, like, why he's been good at business. I think about this a lot because it, it's very simple, but it does still require a discipline.

• 1:06:14Speaker 24

  Let's cut right to the chase. This is one of the greatest pieces of advice I got from my, my late grandfather, Irving Harris. He heard me complaining one day, soon after Union Square Cafe opened, about how hard something was or, he said, you know, stop complaining about problems. He said, problems is the definition of business.

• 1:06:34Guy Raz?

  Yep.

• 1:06:35Speaker 24

  And he said, the people who do best in business aren't the ones with the least problems or the people who solve their problems better and have more fun doing it with better people.

• 1:06:46Guy Raz?

  I love that. That have fun solving, it's hard to say, you have fun solving problems all the time, but I think it's true. I mean, one of the things that I wanted this show to be is a compendium of mistakes on how, how people solve problems that you might not exactly deal with if you're, you know, starting Ring or an apparel business and you're listening to a guy who's got a hamburger joint. But actually, a lot of the problems that he solved are problems you're going to have. You know, how to deal with personnel, how to deal with difficult conversations, how to deal with a challenging investor, how to get people to believe in this idea and, and want to try it.

• 1:07:21Speaker 01

  Yeah. And I think if you're looking at it in that way, like he said, like, it's like surrounding yourself with like, the people that want to help solve these problems, that is the cycle time. That's how you get like business to, to move forward and build great companies.

• 1:07:33Guy Raz?

  In the last 10 or 15, maybe 20 years, there's been this kind of philosophy around business that it's a family. And I think that's starting to change and shift a little bit back to, but this idea that, oh, you know, we're a family and, and, and I will say, you know, at the end of the day, in my view, a business is valuable because it employs people, it gives people a sense of purpose, it enables them hopefully to build a stable and secure life. And hopefully for a lot of people. But I remember when I talked to Paul Orfala, the founder of Kinko's, he had a very refreshing take, you know, he was just very straightforward about the idea that a business is not your baby, that you should have some emotional distance from it.

• 1:08:17Speaker 24

  And I'll tell you something that bothers me, is when a business person says, I love my business. That's absolute bullshit. You love your family, you can enjoy your business, but once that becomes a love affair, you lose your objectivity. I never loved my business. I could enjoy it, but man, your business is an instrument to make you happy and you own it, it doesn't own you.

• 1:08:41Speaker 01

  I just love this guy. Like, it's just like, why is there a line, money? You know, it's like, it's like your business. I, I actually disagree on this one. I think, I mean, for me, Ring is much more than that. And I'm not saying that's healthy. It's just, that's what it is. Like, that's just, it is a part of my family and me and what I, you know, I am linked to it forever and I care about it deeply. And when I saw it not performing as well, I wanted to help it again. But, you know, in some ways, I wish I had his ability to say, I don't care. Like, I, I wish it was just like, I own it. I, I don't. Ring does own me.

• 1:09:17Guy Raz?

  Yeah. I think there's a, a healthy attitude in, in what Paul says, you know, and definitely it's hard for a lot of people to have that view. I understand why, because there's an emotional part to this. But it, it is refreshing. I mean, it is a new way of looking at it. You know, I, I would say the most controversial thing about the show, Jamie, is my last question that I ask people. I say, what do you think is the reason why you succeeded? Was it, was it luck? Was it skill? What do you think? And I started this from early on, maybe the first, I can't remember, one or, and it was just a throwaway question I asked. And it just became organically the thing that I ask at the end. And I, in a few episodes, I didn't ask it because I thought, okay, you know, because

• 1:09:59Guy Raz?

  occasionally on Twitter or somewhere, people would write in and say they hate that question or you, but when I didn't ask it, people were like, what is going on? Like, the overwhelming response. And I realized that those occasional voices who were like, I hate that question, so stupid, okay, you know, this comes in territory. The thing is, is that I'm not actually asking. And it's important for the listener to know the context because I have just interviewed that person in a way that for most of them, the vast majority of them, is the deepest, most intimate interview they've had in a public setting ever. They've bared their heart to us. And so I'm at a vulnerable moment, I'm sort of saying, okay, now answer this thing.

• 1:10:43Guy Raz?

  But it is also interesting and revealing to see how someone's mind works. I, I interviewed Tom Campion, the founder of Zumiez, that skate and snowboard shop that you see in malls. And it was, and I still is a, a successful company. So I asked him, I said, you know, at the end, Tom, what do you think? And this is what he said.

• 1:11:00Speaker 25

  This isn't luck. It has nothing to do with luck. That's not arrogant. It's not luck. It's about measured discipline, hard work going forward. Yeah. Luck may be a very small part of it. It's hard work. That's why not a lot of people do it because, you know, it's hard work.

• 1:11:18Guy Raz?

  And he's not wrong.

• 1:11:20Speaker 01

  I look at luck as every hour I work, I get another lottery ticket. So I have to work for it like I'm not getting luck by just sitting back. I'm working for every lottery ticket, but I'm also not guaranteed to actually win. Cause I've seen people work super hard and do everything right and just, you know, again, just bust their ass and not make it. And so I think just saying it's hard work and skill is not fair to, especially if you're trying to build something big and impactful.

• 1:11:49Guy Raz?

  Yeah. I interviewed Toby Lutka, the founder of Shopify, and he really leaned towards luck. And, you know, he had started a business that was designed to sell snowboards and he couldn't find a good website and to, to, to put his snowboards online. So he built it himself and it, it turns out that it was so good and it was so easy to use that other people were asking him if they could use the, the template. And that turned into Shopify. That, that's what turned into the business and it really wasn't planned. And so for him.

• 1:12:20Speaker 26

  I remind myself how much of this was luck. The incredible timing of when we started, like this is not a kind of company that could have been started even two years later, right? It needed to be started right then and it needed to be ready and good by the time the opportunity around the financial crisis came around. Luck is such a major component of entire journey. So like, why am I the person who ended up, you know, winning the lottery five times in a row? I don't know.

• 1:12:48Guy Raz?

  He bought a bunch of lottery tickets.

• 1:12:50Speaker 01

  But he put himself out there. He worked on it. And this is also where like small things can become big things. It's like the cherries, like you walk by the cherries and you see that. I always think about Weber, the, the grill company started as a machine shop. They basically were welders and they basically welded open a 55 gallon drum in the parking lot to barbecue from. And that became a grill company that became, you know, a massive still today, like a massive business. And so what Toby said, like he had almost get struck by lightning and he, but, but he did.

• 1:13:23Guy Raz?

  And mo- and most founders, I would say, talk about it being a combination of those two things about luck and skill, which is, you know, a version of, of what we're talking about here, putting yourself out there. And Drew Houston, who founded Dropbox, he had a really nice analogy, I thought. It was in the way he described why he thinks it worked for him.

• 1:13:45Speaker 01

  So I think about it like surfing, like that waves will come. And in our case, like we had, we caught this tidal wave, you know, we're just sort of sitting there on our board and then, oh my God, you know, suddenly we're 50 feet off the ground. But inevitably that wave like slows down and then it's like about catching another one and another one and another one. So I think there's luck in terms of when and how any given wave shows up and where you are on your board. But then there's a lot of skill in staying on and, and finding the right wave.

• 1:14:14Guy Raz?

  I love that analogy. I think that's right.

• 1:14:16Speaker 01

  So the funny thing is I've actually, I've actually surfed with Drew. So.

• 1:14:18Guy Raz?

  Oh, yeah.

• 1:14:19Speaker 01

  So, so like, it's a really visceral metaphor back by, back way back in the day, way before Ring and, and really early Dropbox days.

• 1:14:29Guy Raz?

  Wow. It's so fun. I mean, we've just scratched the surface of what we've had on the show over the last 10 years, you know, hundreds and hundreds of founders. And we've just touched on a few of them and I, and I'm listening, I'm like, oh God, we don't have this or we missed this one or what about that? But then we would have like a, a 10 hour episode and, but all the episodes are in archives and anybody can listen to them. And, you know, and I, I hope people do, and I hope people continue to get a lot out of it. Cause when I started the show, you know, I remember having conversations with people and we were like, are we going to run out of stories to tell? Are we going to run out of it? And the answer is no. Like I hope we are talking about this in 10 years from now, because I really want people to build stuff and to bring their creativity to, to, to innovating.

• 1:15:10Guy Raz?

  And, and I'm a believer in entrepreneurship and I think it's what powers and fuels good things.

• 1:15:19Speaker 01

  It's not just starting a business. It's entrepreneurship in any job you have and how you approach things. It is a, it's like a, it's a thought. It's a way of doing something. And I think that when people can unlock that, they achieve the highest and best in whatever their area is that they're in.

• 1:15:35Guy Raz?

  So you know, the question I'm asked most frequently from listeners? Guess what question?

• 1:15:40Speaker 01

  Who's your favorite episode?

• 1:15:42Guy Raz?

  That's number two.

• 1:15:43Speaker 01

  Okay.

• 1:15:43Guy Raz?

  That's number two. I'll tell you, they ask me, so what do you attribute the success of how I built this to? Do you think it's luck or skill?

• 1:15:50Speaker 01

  They turn it right around back to you. So, so Guy, I'm going to ask you, what do you attribute the success of the last 10 years of how I built this and the impact? Is it luck or skill?

• 1:16:01Guy Raz?

  I think it's, um, there's a lot of both of those things and, and skill is not the right, I don't think I'd use that word. I think it's work. We really try to give people a credible and honest account. And we're not going to get every detail right, but we really sweat the details. So that takes a lot of work and a lot of effort, but we also got lucky. I started in podcasting in 2013, when very few people were listening to podcasts and, and I've been so lucky to be part of that wave. And to start, have started the show 10 years ago, when we could still reach, you know, reach through the noise. There was just a lot more noise today. So, uh, yeah.

• 1:16:44Guy Raz?

  I mean, I think had we waited a year or two to start how I built this, it might've been different. You know, when we launched it, it was also this kind of wave, this post-financial crisis wave of money coming into startups and all kinds of people trying new consumer products and direct to consumer. Now we're changing. There's a shift into AI and to different ways of doing business. And so we're going to have amazing stories that are happening. People are writing their stories right now, which hopefully we'll be able to tell in, in five years or more. And, and that to me is so exciting.

• 1:17:17Speaker 01

  Well, it's, it's just like we talked about, it's not complicated. It's just hard, you know? And it's like, it was a ton of work and a great team and all the things you have to do. And then those waves, like Drew said, you know, like you were out there paddling and the waves kept coming.

• 1:17:33Guy Raz?

  Jamie, thank you for joining me on this. There's nobody better I could have had as a partner here.

• 1:17:37Speaker 01

  Thank you so much.

• 1:17:39Guy Raz?

  That's Jamie Siminoff, the founder of Ring. And thanks so much to all of you for listening to the show this week and every week. And you can hear the full episode of any of the stories we talked about wherever you get your podcasts, just scroll through that feed and you'll find them. And as always, please make sure to click the follow button so you never miss a new episode of the show. This episode was produced by Casey Herman and edited by Neva Grant with music by Rameen Arabloue. A special thanks to Teresa Mondria-Tarol, who helped us excavate and organize hours and hours of How I Built This audio. Our engineer for this episode was Robert Rodriguez. And finally, a shout out to the incredible team of people who have helped make this

• 1:18:20Guy Raz?

  show over the years, including Jeff Rogers, Sanaz Meshkhanpour, Julia Carney, Rachel Faulkner, James Delahoussaye, Liz Metzger and Rund Abdelfatah. And our current team, Chris Messini, Alex Chung, Sam Paulson, Carla Estevez, J C Howard, Catherine Seifer, Kerry Thompson, John Isabella and Elaine Coats. I'm Guy Raz and you've been listening to How I Built This.