The Exchanges

Q read it back in 2005, 2006, somewhere in that time. I think it's probably worth reading that because it would really, it might spark an idea of how you can take the brand that you already have, which is already in a great spot, and elevate it to the next level to get people's attention. And the kind of thing that, like, what would get you on a morning show?

A Yeah. And there's a way to do that, Joe. I mean, I've got a, I'm not trying to promote it, but I've got a whole kid's podcast and, and, and a whole kid's, um, science business, and we just release, like, toys. So we've got exploding volcanoes and stomp rockets, and they're sold in, in, in shops and on Amazon. And we basically did, um, a whole day, two, three days of, Of just back-to-back-to-back local news interviews, me and my, my partner, Mindy Thomas, you know, you just basically hit up every local news channel talking about this thing. I mean, your story's great, and local news needs to fill time. I promise you that. You can go to every, I mean, from South Carolina all the way to Eugene, Oregon, and beyond. I mean, it's going to take a little investment, not as much as you think, though.

AI assessment note: “you just basically hit up every local news channel talking about this thing”

Q a journalist, and you think these are the stories that people want to hear. And as humans, I feel like we are just drawn to the hero myth. I mean, Joseph Campbell makes the point that this is, like, pretty much universal. All cultures have a hero myth. What do you think it is about the hero's myth that we love so much, that, like, draws us in so much?

A I mean, I think we're drawn into it because there are elements of it that mirror our own lives. We will all experience grief and hardship and struggle and challenges and moments, um, you know, maybe not, not this extreme, but moments where we're on the bathroom floor crying in the fetal position. What I think is so remarkable about the stories on how I built this is that they're designed to be relatable. You know, I want people to hear the story of Sarah Blakely and imagine Sarah Blakely Going door to door selling fax machines. And, you know, after the 100th person tells her, please leave our premises, no soliciting, you can picture her in her car just crying and saying, this is not, this is not what I want to do. This is not how I want to live my life. And I think anybody listening to that story can relate to it. You know, Sarah Blakely, of course, started Spanx and became the youngest self-made billionaire in American history.

AI assessment note: “we're drawn into it because there are elements of it that mirror our own lives.”

Q So B, your B to B, just go, kind of, go that route?

A I don't think it's one or the other, but I think that's a really promising channel for you, because this is something that, you know, um, you could sell to, like, my family's going to, you know, we just got back from Italy for three weeks. We could have gone and, and done that, but selling a kit, a one-off kit, you know, to a family every five or seven years, uh, is one, is one channel, but, but having a company that has people traveling all the time, That will then need to renew the kits because, you know, medicine, as you know, right, it, it expires. Um, that to me seems like a really cool opportunity to really think about working with, um, you know, corporate partners.

AI assessment note: “I don't think it's one or the other, but I think that's a really promising channel”

Q Your precondition is that you don't accept preconditions?

A Right. We don't say that to be difficult, or to embarrass people, but a lot of, you know, a lot of famous people are used to doing interviews where there are, there's kind of a give and take. Like, I won't talk about this They won't talk about that. They won't talk about that. And I totally respect that. That's fair enough, especially when it comes to celebrities who want to protect their privacy. On our show, we can't do that because we, we are avatars for our listeners, for our audience. Our audience expects us to ask the questions that they want answers to. So what, what I always say to our guests is this is a 360 degree view of who you are. There's nobody on planet Earth who is perfect. Every single person has flaws. Everybody's made mistakes. Everybody's done stupid things. That's the point of the show. It's to show your entire journey, you know, this full contextualized story of who you are, what you did, the mistakes you made, why you did them, what you learned from them along the way. And I think that's been really, you know, that's been a really important part of why the show connects with people, because I'm actually much less interested in success than I am in failure. We learn so much more from people's failures than we do from their successes. If you heard our recent episode we did on Ring doorbells with Jamie Siminoff, 80% of that, that episode is about his failur…

AI assessment note: “Right. We don't say that to be difficult, or to embarrass people”

Q ends well, but at the time, you're on your last credit card, you don't know that the story's gonna end well. And in the process of writing the book, because that is a little bit of a different process, although the book is very, very related and intertwined with the show, Did you learn anything either about the show, or I'm just wondering what that process kind of taught you?

A Yeah, I mean, so much. You know, ultimately, what is really remarkable about when you sort of begin to see this in context is that every single person who has been on the show is, starts out more or less at the exact same place. Not in terms of the resources they might have, or maybe connections, but the same exact place, which is They haven't proven anything. They haven't gained the confidence of anybody yet. You know, Airbnb, the guys who created Airbnb in 2008, they went to 20 investors. Not a single investor invested. And so what really strikes me is that we are all at a certain point starting out more or less in the same spot. You know, there's a great line that Bob Dylan sang once, you know, sometimes even the president of the United States must have to stand naked. And it's a reminder that we are all in this vulnerable spot, you know, at a certain point in our lives, and all it really takes is a slight nudge, pivot, twist, turn, luck, hard work, call it whatever you want, but something that then gets you out of that moment of vulnerability, and that's what's really, you know, incredible to me about all these stories.

AI assessment note: “every single person who has been on the show is, starts out more or less”

Q maybe this is, is too insider baseball-y, but you said When you started the show, you'd done thousands of interviews with all kinds of different people in all sorts of circumstances, but that you were actually quite nervous for your first How I Built This Interview, which very much captivated my mind, because I wonder, like, what, what was that first interview like for you, and why were you nervous?

A Yeah, I mean, the way I think I express nerves is a little bit different. I mean, I get nervous, aversion, I experience aversion of nervousness before every interview I do. And it's not, not nervous about the, you know, meeting the person or being in a room with them or whatever it might be. I want it to be so powerful. I want the story to be so, you know, so resonant. I want it to be worth our listeners' time. If you, as a listener, Are going to give me an hour of your time. I have to make it worth your time. I have to, I mean, an hour of your time is extremely valuable. You know, we have maybe three or four hours at most of free time to ourselves every day, and fewer if you've got people that you take care of. And I'm asking somebody to give me an hour of their time on a certain day to listen to how I built this. I better be giving you something worth your time. And so that's really where the nervousness comes from. And with Sarah Blakely, um, I wanted that first episode to be so powerful. I wanted us to send a signal that we were doing something different, that we were going to create a show about business that was going to sound different, that wasn't going to include the usual suspects, that was going to be full of diverse voices. And I want every episode we do to be excellent. I want people listening to it to come out of that Feeling inspired and energized and, and really…

AI assessment note: “I wanted that first episode to be so powerful. I wanted us to send a signal”

Q when I'm at the football game is take a picture to show my friends that I was there. And that's where the knocks kind of, can you, can you get that? I guess. Cause kids, I mean, everywhere I go now, all they do Is these selfies and these, like, it's, again, I don't love it personally, but I think from a business side, you have to lean into it.

A I think that's, I think that's really, really interesting. I, I'm going to take a slightly different tech. I think Jamie's probably right. Like, if you want to make money, follow Jamie's advice. If you don't want to make money, follow the advice I'm about to give you, which is, I actually think your biggest competition is distraction, right? And, and I'm really interested in this whole Movement of people who are interested in analog experiences, putting their phones. I've got this thing called a brick. It's on my fridge. I scan my phone, and it locks it up, and I got to go back physically to that thing, and it unlocks. It's very analog, but it's great. I think that maybe you might want to think about creating some kind of campaign around like a daily ritual, like put away the phone, no phone, uh, you know, take a walk. Go outside. Look up. I just think that there's an opportunity to lean into this kind of screen-free, like, sort of decompress kind of thing that's happening, because a lot of people are interested in it. Their brains are overloaded with junk that they're getting from their devices, and I wonder whether you might want to kind of lean into that.

AI assessment note: “I'm going to take a slightly different tech. I think Jamie's probably right.”

Q mothership all of these great products that we've already figured out how to make. I mean, franchising isn't necessarily my first avenue of choice. I mean, I think, you know, in cream, in the world of cream cheese, do I really want to take on Philadelphia? Like, I've got really big boxing gloves, but can I do that? I mean, the world of dairy is like a whole nother thing.

A It seems to me, it seems to me, Jennifer, that your competitive advantage is your, is your brand, right? And, and also their sourdough bagels, which is, which is somewhat of a differentiator, but it's your brand. Badass bagels. You've got a great logo. You've got a great look. You know, we have an episode of our show about Dave's Hot Chicken, and that brand was started in a It was basically a parking lot. It was a couple of friends, and they basically decided to sell fried chicken sandwiches. Within a year, they were approached by somebody who had experience in franchising and paid them a significant amount of money, and that's actually really worked for them. But, you know, Pete, it seems to me that if Jennifer were to do this, she would want to really be mindful about who that partner is.

AI assessment note: “competitive advantage is your, is your brand, right? And, and also their sourdough bagels”

Q But how do you balance, um, I mean, I think there are definitely things that can be done to improve the store. How do you balance the national brands? Like, you met Olipop, and you mentioned Bobo's. You know, how do you balance the local brands versus the national brands in a, in a cooperative store?

A I think the key is, is curation. It's finding, it's finding products that you guys really like. I mean, this is what makes Trader Joe's so successful. You know, they don't, they don't have thousands of SKUs. They have very few, uh, products on, on the shelves, but people know that it's been through, you know, Trader Joe's people have tested it, and, and if they don't like, like something after a while, it goes away, but you know that what you're going to get there is probably good. I think you want to take advantage of your Of, of the curation of the, of the folks who, who run the co-op, uh, and, and that's what people trust. They, they want to go in and say, oh, I've never seen this beef jerky. It might be a national brand that they still haven't seen, or it might be a national brand that they have seen, like Olipop. It's, you're going to have some of that too, but, um, I, I think the key is, is that your, the products that you've got in the store are practical. They're things that people want to use and want to cook with and also eat, obviously, but they are also products that they know, you know, You guys have tested out that you guys like, and, and I think that's what's going to make the difference.

AI assessment note: “I think the key is, is curation. It's finding products that you guys really like.”

Q business? What's the next milestone for what we want to build? And then let's get there as quickly as we can. Okay. We, we raised, you know, as you said, another a hundred million dollars in March of 2019. What's next? Okay. Let's, let's get ready to be a public company. What is that like? So yeah, It was really, I think, more self-imposed pressure to get public than anything.

A But going public means that you have to reveal everything. Going public means you're all your financial statements, your documents are now public documents, because that's what it means to be a public company. And so, a month before your IPO, you had to, you know, this, all your documents are out in the open, and it showed that you were not profitable. That actually you had lost money in the previous quarter and that the company wasn't yet profitable. That's fine. That happens all the time with many companies. And when people buy a stock, it's often on the belief that eventually they'll reach profitability, but, but it, but all of a sudden you kind of lay, lay it out there, right? I mean, you're not, you, you, it's all out in the open.

AI assessment note: “going public means that you have to reveal everything. Going public means you're all”

Q That you say quite a bit. The word is wow. You're very known for it. It's like your signature. I'm wondering if you can talk to me about wow. Why, why does this come up so much in your interviews?

A You know, before I do an interview with somebody, we spend a lot of time digging into their life. So, I know a lot about the person. What I then do when I go into the interview is try and forget all of it, and go inside of that person's head. Because we are all living in our own movie, right? We're all, our consciousness is basically our, our movie. Everyone's life is from their own perspective. And it's almost impossible Pretty much impossible to get inside somebody's head and to see the world through somebody's perspective. When what I'm trying to do is to get inside somebody's, you know, into the cockpit of their brain and to sit there, you know, next to them with the steering wheel and relive that journey with them. What happens is, is that I am swept up in that story so intensely because I'm with them on that journey. I'm with that person. I'm with, you know, Kate Spade. I'm with her as she's She comes to New York City from Arizona to start her job at, you know, is it a low-level editorial assistant at Cosmo, and, and the day, you know, her husband, uh, Andy arrives, and, and he, and she can't find her keys, and he has to climb the, the fire escape ladder to get to their studio apartment in New York in the eighties. You know, I'm with her. I'm with her as she's telling me that story, and it's mind-blowing. It's just so exciting, and so the wow is not a conscious thing that…

AI assessment note: “the wow is not a conscious thing that I do. I'm, I'm just in awe.”

Q Exactly. The customer drove us to, to a national footprint, and ultimately international, right?

A Yeah. Yeah. I think by, by 2006 pods, so this is like eight years in. It's franchised in 45 states in the US. It, uh, expands to Canada and Australia. There were thousands of pickups and deliveries a day. Um, I mean, you probably were doing three hundred million dollars in revenue at that point, and around that time, I think it was, it was, it was about, it was 2007, um, you did an interview on a local, about, uh, public television show, and, um, you know, this guy, this guy's interviewing you about your story, and, uh, he says, what do you, what do you want to do? Where do you see pods going? And you say in this interview, oh, I think we can be, you know, like, work with, eBay or, you know, where if people want to sell, you know, their, their exercise equipment, you could just stick in a pod and we can ship that over to another part of the country really quickly, like FedEx or UPS and make it seamless and frictionless. And shortly after that, you sold the company.

AI assessment note: “Yeah. Yeah. I think by, by 2006 pods... expands to Canada and Australia.”

Q as equitable or fair. And that came to bear for a lot of other sort of companies of our time, because we had all ushered in this, hey, we can build a company, do good, be transparent, and treat everyone well. Our customers, our employees, our factories. And then I, COVID happens, and it's sort of like, how do you, how do you do right anywhere when everything goes wrong?

A I've been thinking a lot about what's, what happened with a lot of companies, and, and still is happening to some extent. They started with this premise that you're part of a mission, and the mission is transparency and openness, whatever it might be. It's, it's making the world a better place. And employees believe that that was their role. And I wonder whether some of that Tension, because you had employees who were really mad, and, you know, and lots of companies did. And I wonder whether some of that comes from that idea, that, that All of a sudden, they're like, wait, my mission is to make money for the company? I don't know. Is that, does any of that resonate with you?

AI assessment note: “I wonder whether some of that comes from that idea”

Q stores and distribution, you know, if most of the people already buy their, um, toothpaste through, um, existing stores, You know, how can you be alongside, um, where those other products are? Because at the end of the day, um, changing habits is really hard, and you almost don't want to change. You want to take the world as it is, and then sort of insert your product into it.

A Yeah, I mean, there are probably millions, but you want to really focus on, like, 10,000 parents, right, who live on TikTok or in Facebook groups who are, Who sort of gather around some of these issues, uh, brushing, fluoride free, et cetera. Sampling makes, is to me, I completely agree with Neil. It's like sample, sample, sample. You can make these small packets and you, whoever is willing to give a daycare center, swim schools, summer camps, you know, Neil said birthday party goodie bags. Um, you know, because what, what you have, right? Your product is, Essentially is a gummy toothpaste, but what it makes me think of, Neil and I were talking about this earlier off mic, um, Jeff Rader, who, who co-founded Warby Parker and then went on to start Harry's, uh, they have a product that they now bought called Lumi deodorant, right, Neil? Is that right?

AI assessment note: “Sampling makes, is to me, I completely agree with Neil. It's like sample, sample, sample.”

Q And so I feel like I have to ask you, what was the biggest moment of struggle for you in starting the show? Was there a moment when, I don't know, you felt like it wasn't going to work, or you didn't want to do it, or when you hit a wall yourself?

A Yeah, I mean, there were certainly moments where, um, it was certainly not clear whether it was going to happen, but you know, I think what's important And one of the reasons why I focus so much on crisis and struggle is that implicitly in how I built this, right, the people who come on the show, we know they're successful. We know they have achieved some level of success, not always financial, but they've built something that's out in the world that has had some kind of cultural impact. And I think we often default into thinking that these people are superheroes. And that's why I focus so much on those moments of failure. The moments of crisis. You know, when Jamie Siminoff is wondering whether they should take a line of credit against their mortgage and worrying that they're going to lose their house. Or James Dyson pretty much broke at the age of 42 because he spent seven years trying to perfect this vacuum cleaner, and everyone thinks he's crazy. Or Gary Hirshberg spending eight or nine years losing money while building Stonyfield yogurt and not really sure whether it's going to work. Throughout my career, I've had so many failures that were so pivotal and so challenging and so difficult at the moment, but were so important in hindsight. You know, now, now that I can reflect on them and can think about those moments of failure, I really understand that they were so necessar…

AI assessment note: “there were certainly moments... but you know, I think what's important”

Q can get this right. We'll get this right would mean what if everybody was liable for the downstream harms that could occur and they all moved at a slower pace. Not a generically slower pace, but at a pace in which we're doing the relevant safety work. And how would we rebalance that equation so that everyone is doing a race to safety versus a race to power and capabilities?

A How will people start to see this impact their lives? So I, I was on Instagram this week and, um, I got delivered a surfing video and it was a video of Kelly Slater surfing and beautiful, pristine waters. And he was just weaving in and out of other surfers, maybe 40 surfers. It was an amazing video, and I looked at the comments, and they were uniformly, you know, you just went down, they're like, wow, this guy's the goat. This is amazing. Wow. And then finally, there was one comment, and it was like, guys, this is AI generated, and I looked, looked at this video, and I, I'm pretty sure it was AI generated, you know. That's already happening. Some of it is very good, and it's not even a fraction as good as it's going to be if, as you say, this, there's this exponential curve as good as it'll be in A year, five years, 10 years from now. What are we talking about? To lay it out for me, Tristan, I mean, are we talking about a world where nothing is real and everything is, I mean, it's, it's like Aldous Huxley again on steroids. We just will not be able to even know if a call from our spouse is real.

AI assessment note: “How will people start to see this impact their lives?”

Q Wouldn't it be nice to just own one restaurant?

A I mean, you could, for example, there are certainly many examples of this, you could lend your name to a restaurant chain, right? And, you know, Wolfgang Puck is an example. You can go to airports and see Wolfgang Puck restaurants, but he's not controlling the The quality of those restaurants. And so, obviously, you can make a lot of money doing that. You could have, you know, Thomas Keller presents, you know, bakeries all around the world. And I wonder whether, A, would you be willing to do that? And B, do you think you could do that and still control the quality of those places? Because you've got, it's a lot, but you have a relatively manageable number of places now that you can make sure that they are up to your standards.

AI assessment note: “you could lend your name to a restaurant chain, right?”

Q Absolutely wasteful. And you end up, when you have to make like that, that's why you are selling a pair of jeans for a thousand dollars, is because you didn't figure out the supply chain at all for that, right? It takes a year to figure that out.

A One of the really interesting things that you did was, and I don't mean this in a pejorative way, so I hope it doesn't come out that way, but you kind of used the, the, the sort of the machinery of the fashion industry to build yourself up to a certain level, and once you were able to make the choice to completely reject it and move away and start your own thing, and that may have been that 400,000 dollar grant in 2017 that kind of helped you to jumpstart it. You were able to do it, right? Because you had, you kind of got to the point as far as you could get with the fashion industry, and you knew that in order to, to, to grow and to thrive, you had to leave it. Is that, is that a fair interpretation?

AI assessment note: “One of the really interesting things that you did was”

Q Yeah. That business in Saudi Arabia is Half of it is state-owned. Now, what do you do? Do you work with it or not?

A Let me, let me ask you about this world of content creators. I mean, obviously, today, it seems like everybody is a content creator, and you have this academy that really helps people build out their brands and their platforms and to monetize it, but can we have a world where everybody is a content creator and that, and for that world to be productive and harmonious and Sustainable. I mean, part of me is like, I kind of worry that so many people want to become YouTubers, so many young people, my kids, you know, they're friends. And again, I might just be like, I have the worst, stupidest perspective about this. I concede, but part of me is like, I don't, I'm not sure that's sustainable, that we can all become content creators.

AI assessment note: “Let me, let me ask you about this world of content creators.”

Q limits that you only know that you're capable of achieving. That's what this is about. So, you know, in life, it's all about the decision. You, you can make a right, a left, A U You can follow the map, or you can choose to wing it and go in a different direction. It's all about your decision. How do we take responsibility for that? That's what this is about.

A Yeah. I mean, on, on our show and how I built this, we talk so much about failure with entrepreneurs because failure is more interesting than success, right? Like we learn more through the failures of others than we do through their successes. And I really feel like the failures I've had in my career, you know, the jobs I didn't get and the, you know, directions I didn't take were blessings. They're really blessings. I mean, they're hard at the time they were crushing, but had those failures not happened, I wouldn't be doing what I do now. Is there a failure like that in your career that was just crushing at the moment? But when you look back on it, you think, God, Thank God that actually happened.

AI assessment note: “on our show and how I built this, we talk so much about failure”

Q terms of how this is going to devastate. The majority of employment in the United States of America is based on small businesses, small entrepreneurs. They are being wiped out. They are being totally eliminated. They were already under fire trying to compete. What happens when we don't have these independent entrepreneurial ventures to provide services, number one, and also to provide employment? So while I'm encouraged, I'm also frightened.

A You know, Kathy, it's, it's really sobering to hear you talk about that. Cause you're probably one of the most optimistic people I've ever met in my life. I remember when you were on the show, I kept asking you about, you know, all of the struggles that you went through. And I want to talk about some of them being bankrupt for years, having creditors breathe down your, your neck and, and, and still being positive, knowing that you were going to succeed. I remember you saying, I knew I had no doubt. I was worried, but I was never worried that I wouldn't make it. And that was like, it was such a Charge, you know, when, when you said that in the show, because, I mean, you really struggled for so many years to build this now an empire.

AI assessment note: “it's really sobering to hear you talk about that. Cause you're probably one of the most optimistic”