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On this episode of Dare to Lead

I talk with Guy Raz, the creator and host of the popular podcasts How I Built This, Wisdom From the Top, and The Rewind. Guy and I dig into the importance of an entrepreneurial mindset, what gets in the way of innovation, and the transformative power of story. I think his new book, How I Built This: The Unexpected Paths to Success from the World’s Most Inspiring Entrepreneurs, should be mandatory reading in business schools — it’s an incredible playbook!

About the guest

Guy Raz

Guy Raz is the creator and host of the popular podcasts How I Built This, Wisdom From the Top, and The Rewind on Spotify. He’s also the co-creator of the acclaimed podcasts TED Radio Hour and the children’s program Wow in the World. He’s received the Edward R. Murrow Award, the Daniel Schorr Journalism Prize, the National Headliner Award, and the NABJ Award, among many others, and was a Nieman journalism fellow at Harvard. He lives in the Bay Area. His new book, How I Built This: The Unexpected Paths to Success From the World’s Most Inspiring Entrepreneurs, came out in September 2020.

Show notes

How I Built This: The Unexpected Paths to Success from the World’s Most Inspiring Entrepreneurs

How I Built This with Guy Raz from NPR

Wow in the World from NPR

Wisdom From the Top by Built-It Productions

“All of these songs remind me of a time and a place that was meaningful and that brings meaning to my life. And when I think of those songs, I think of those experiences, and they make me happy.”


Brené Brown: Hi, everyone. I’m Brené Brown, and welcome to the Dare to Lead podcast. In today’s episode, I am talking with the one and only Guy Raz, creator and host of the popular podcasts How I Built This, Wisdom From The Top, and The Rewind, about what inspires an entrepreneurial mindset. Let me tell you, as someone who spends a lot of time in organizations working with leaders, more and more, the people that I see rising into positions of influence and leadership positions, the people that I see getting really great jobs are people who have what many people call a founder’s mentality or an entrepreneurial mindset. And Guy’s new book that is based on the podcast, How I Built This, is such, just full of wisdom. This book is so important. I have to say that if I was inside of a business school teaching bachelor’s level business majors or MBA students, or folks that are preparing for leadership in NGOs and nonprofits, or healthcare leadership, I would have this book in at least one class. This is what we expect from people in organizations. We expect for people to learn, to grow, to stretch. An interesting point that Guy makes, that the same mistakes are made over and over, 1000 times every day, how can we learn from them?

BB: So we’re going to talk about this entrepreneurial mindset. We’re going to talk about what our culture is demanding of leaders today, what’s getting in the way of us showing up in innovative brave ways, and how can we shift. I cannot wait for you to hear this conversation. It just blew me away. So many of you probably know Guy, have listened to his podcast. He is the creator and host of, again, How I Built This, Wisdom From The Top, and The Rewind podcast on Spotify. He’s also the co-creator of the acclaimed podcast, TED Radio Hour, and the children’s program, Wow in the World. He’s received the Edward R. Murrow award, the Daniel Schorr Journalism Prize, among many others. He is a Nieman Journalism Fellow at Harvard. He lives in the Bay Area, and his new book, the one that we’re going to really dig into, is How I Built This: The Unexpected Paths to Success from the World’s Most Inspiring Entrepreneurs. And we’re just going to jump right in.

BB: So I must just start by saying I’m a little intimidated.


GR: How can I make you feel less intimidated? I’m an open book. I am surrendering.


GR: I have surrendered to, to you here.

BB: I’m intimidated, because I’m a new podcaster, and the New York Times calls you one of the most important podcasters in history. Did you know that?

GR: Yeah, but it’s one writer in the New York Times who put that in an article. But then, of course, it turns into the institution of the New York Times saying all these things. And so it’s very nice, I appreciate it, but I don’t really know if it’s true. [laughter]

BB: Okay, so let me just start by saying we’re going to talk about How I Built This, the book, which I think should be mandatory reading in every business school and MBA program in the world. I’m going to recommend it in the MBA program that I am actually teaching, at the University of Texas. I love the podcast, I love the book, but before we even go into the book… Well, I’m going to Guy Raz you a little bit.

GR: All right.

BB: So I want to talk about what you’ve built. You’ve built something pretty significant. Tell me about all of the podcasts that you’re involved in, and tell me how they came to be.

GR: Well, the one that probably most people know me for is How I Built This. And that really began as kind of a side project for another show that I was the host of and one of the co-creators of, called The TED Radio Hour, which is where we first met, because you were on the show. And I’ve been in audio for like 23 years. I started out as a radio reporter back in the day, and in 2012, I kind of left the news world and I helped to create the show, The TED Radio Hour, which was this amazing, exciting collaboration with TED, the TED Talks people. And it was a wonderful, incredible, creative endeavor where we were able to talk to people like you and Daniel Kahneman and Bill Gates, anybody we wanted to who had given a TED talk about their ideas. And a few years in, I’d always wanted to do a show about entrepreneurs, I’d wanted to do it for quite some time. So I’m going to wind back for a moment because in 2008, I had the opportunity to do a fellowship for journalists at Harvard, called the Nieman Fellowship, and it’s an amazing experience. I had this opportunity to take any class I wanted, and I took classes on ancient history, and I took classes in the Divinity School, I took classes at the Law School, I took one class at the Business School because I thought, “You know, I don’t know anything about business. Why don’t I take a class at the Business School.”

GR: And I was blown away to discover in 2008, that the way they teach business is through stories, the case study method. On day one we got this packet. It was the story of Howard Schultz and Starbucks, and I was riveted, it was so interesting. I was gobbling up all of these case studies. And it really occurred to me that there was something there, that what we do, what I’ve been doing my whole career is storytelling. And it, back then, occurred to me that there’s something to be done about this, that these are stories that we could tell in a very rich and deep way. As I kind of filed it in my head and put it to the side and continued to… I was a host of All Things Considered, and then eventually helped create The TED Radio Hour, which I was the host of. And a few years in, I decided to try this as a side project, this was about four and a half years ago.

GR: And, we launched it almost four years ago, and it was really designed to just see if people would like it and it kind of became my thing. And here I am now. So that is the main show I do. I no longer host The TED Radio Hour. But I also have a few other shows that I do, notably a children’s show called Wow In The World, which I created with my very good friend Mindy Thomas, who is just a brilliant children’s communicator. She has a program on Sirius XM. We’ve been friends for a long time in Washington, DC, when I used to live there. And we were on a hike her family and my family, and this was like, I don’t know, like five years ago, and I said, “Mindy… ” I had been going on her show on Sirius XM once a week to talk about the news for children. We would just talk about what was going on in the world. And I said, “Mindy, we should start our own podcast. We could do this.” We would take these long hikes in Great Falls, Virginia, or we’d go out, all of our families, her family and mine, and we would have these long conversations. And we decided to create Wow In The World, which we launched four years ago.

GR: We both as parents were freaking out and continue to freak out at how much our children look at screens all day.

BB: Oh God, yeah.

GR: I’ve got a nine year old and an 11 year old, and screens are so powerful. They are powerful over us as adults. And we really wanted to create a screen alternative, but that wasn’t only good for you, but something that kids actually would want. So we came up with this concept for Wow In The World, which was, it would be a cartoon for the ear, and every episode would be rooted in a peer reviewed scientific journal article. So we essentially take peer reviewed scientific journal articles and translate them for children between the ages of five and 12. And we go on adventures around the world, underwater, into space, back in time, we have a flying pigeon, we have a time machine, we have a shrink wand. Mindy lives in a gingerbread mansion, I live in a Eco Friendly House in the woods. I am basically kind of a hyperbolized version of myself, and Mindy is too. We are very much like those characters in real life, [laughter] and our dynamic is like that, and that’s been an amazing experience. So we launched that four years ago, and that continues to go.

GR: And then I do another show called Wisdom From the Top, which is about leadership, and I interview leaders about how they think about leadership, so… And in the past, I’ve done other shows, but those are the three shows I now do: How I Built This, Wow In The World, and Wisdom From The Top.

BB: So I want to read something from your book to you, and then I want to ask you a question. Especially, this is related very much to not just How I Built This, but the fact that you’ve created… I mean, you’re responsible for a lot of revenue, right? You’re shaking your head yes.

GR: Oh yeah. Yeah, yes, yes.

BB: Yes, right? You are an entrepreneur in many ways, right?

GR: Yeah.

BB: Do you have direct reports?

GR: So I’m in an interesting kind of model, which is, I have always been entrepreneurial. I think a lot of people who work for organizations have been entrepreneurial, like…

BB: Totally.

GR: Your employer is the University of Houston, right? And so you have been entrepreneurial within that system, but also have done things outside that system. And for most of my career, I was able to do entrepreneurial things within NPR, and then at a certain point, I left NPR as an employee, but continued to work with NPR as a partner, which is what I’ve been doing that for the last several years. It’s a wonderful relationship, because I can produce programs for NPR that are really profitable for NPR. And NPR is a nonprofit, and that money is plowed right back into the system. It doesn’t go to shareholders, it goes to building bureaus in investigative journalism and in creating new podcasts. And so, of course, I think of sustainability with everything I create, but I never think, “Oh, How I Built This is going to make millions and millions of dollars.” Really the point of How I Built This was to tell stories about people that we perceive to be incredibly powerful, but to actually show that they are exactly what you talk about, that they’re vulnerable, and that they have had moments where they’re on the bathroom floor in the fetal position crying, right?

BB: Yes, lots.

GR: Like, I want to hear that story from Howard Schultz, I want to hear that story from Sara Blakely, I want to hear that story from the people we bring on, and that was the point of the show. It was really designed to show people who are interested in business or creativity or building ideas, that those people you admire, those people you put on pedestals and you think of as superheroes, they’re not that different from you.

BB: No.

GR: They have anxiety, and they have moments of total terror and fear and self-doubt, and I wanted that to come out. And the fact that it has been successful, not just for our audience, but also for NPR is like an additional bonus, and something that we’re all really proud of.

BB: So do you have a production company?

GR: Yes. So I have two production companies. Now it sounds very lofty, but as anyone who has a business knows, ultimately a business is really just a file folder with some documents inside of it.

BB: With an LLC in there somewhere, yeah.

GR: Yes.

BB: Yeah, yeah, I got one of those too.

GR: And then of course, we have an office, and if you want, and some employees. And so I do have a production company called Built it Productions, and we have employees and co-produce How I Built This, and then we separately produce Wisdom From The Top. And then I have a separate production company called Tinkercast, and I’m partners with Mindy Thomas and Meredith Halpern-Ranzer, two incredibly talented women who have amazing experience in children’s media. And we produce kids content, Wow In The World is our podcast, but we make educational content for kids for free. In normal times, we have a robust live show that we perform all over the country. We’re working on a digital platform that will help kids learn through listening. We’re trying to focus on a screen alternative to get kids to listening, and to kind of spark, you know, get the synapses in their brains firing just by listening to things. And so we’re taking this very retro idea of old school radio theater, but modernizing it. There’s a lot going on, I’ve got a lot of different things going on, but it’s so fun, because at the end of the day, these are creative pursuits.

BB: Right.

GR: I get to work with people who I just admire so much, my team that produces How I Built This, and the work we do on Wow In The World. And I learn so much from the people I work with every day, because they’re so smart, and they’re so creative, and it’s so fun. It doesn’t mean that we don’t have moments of tension and frustration, but in general, we’re really able to focus on producing material that we think will enhance people’s lives, we hope will enhance people’s lives.

BB: So I’m reading this, and it’s interesting to me because I may be putting two and two together and getting 495, I’ve been known to do that in the past, but I’m reading this book and I’m thinking… I know about your journalism days, war reporting, and I’m thinking, “Guy Raz, how did you build this?” I’m not just thinking like, “Tell me about what you learned from people who built this,” but I’m reading this and it says, this is about your journey to start this podcast. In high school and college, I used to think that business was a dirty word. To me, it was the realm of hucksters and pitchmen, selling cheap consumer products on late night infomercials.

BB: Why would I care about the story of some business? It’s not like business was ever going to be my thing, especially because I watched the ups and downs of my parents’ pearl importing business and how much time and energy it sucked out of them. I have vivid memories of my parents grinding away at the kitchen table, late into the evening, combing through customer lists, making cold calls that more often than not ended with the proverbial door being slammed in their faces, all in the service of providing a stable life for me, my younger brother, and my two older sisters. So I have two questions. One, after talking to all these entrepreneurs… And you and I share a fundamental belief, I think, about the transformative power of story, is that a true statement?

GR: Yes.

BB: Yes, okay. After hearing all these stories and doing these podcasts, do you think any differently when you think about your parents at that table and that business?

GR: Yes, 100%. Family is complicated because they’re so close to you.

BB: Yeah.

GR: And usually our most challenging and complex relationships are with the people that we’re the closest to and that we love the most, because we take it for granted.

BB: For sure.

GR: And there is that unconditional love, so you can get away with bad behavior sometimes, and there’s baggage from… [chuckle] from living together, from knowing each other.

BB: Yeah. Yeah.

GR: I never really had the kinds of conversations with my parents about their business that directly led me to that conclusion. It was really a matter of reflecting on observing them and then transposing those reflections to my adult self, right? Because as a kid, you’re not sophisticated enough to look at your parents and say, “Oh, they’re struggling.” They eventually built a sustainable business that enabled them to support their kids, but what I realized in writing this book, telling that story, but also telling all of the other stories I tell is that, when you begin to understand somebody’s story, you inevitably become more empathetic towards that person. There’s no way you can’t not feel something for somebody else when you really understand their story. And I first actually learned that fairly late in life, only in my early 30’s or maybe not so late in life, I don’t know. But in that year, when I took a year off to do this fellowship, one of the most amazing experiences I had on the Nieman fellowship was a tradition that they have, which is called The Sounding.

GR: Every Monday night, a different fellow, there are 20 American fellows and 20 international fellows, every Monday night, a different fellow presents their life story and they serve a meal, based on their culture, where they come from, if it’s from Columbia or South Africa or China, wherever they’re from, they serve a meal, and they tell their life story over the course of two hours, with slides. Now, in any group of 40 people, you are going to interact, and some people you naturally come into contact with and there’s chemistry and some people connect and some people just don’t. By the time you know everybody’s story at the end of the year, you are inevitably closer. You see that person in just a completely different way.

BB: No question.

GR: It changes how you interact with them. You might have thought that that person was kind of a jerk or maybe standoffish or introverted or arrogant or whatever it was, and your perceptions were entirely wrong once you understood their story. We trust our intuition so much to our detriment. We think when we see somebody, we know about them. Many of us just instinctively make judgments about other people based on quick interactions or maybe one passing remark in a party or a function or something. The reality is, you don’t really know somebody until you know their story. And what’s remarkable to me is how often we don’t know the stories of people that we interact with every day. I remember about five years ago, maybe six years ago, one of the NPR newscasters passed away. His name was Craig Windham. I passed by Craig in the hallways for 15 years every day. I would say hello to him, he would say hello back. I would hear Craig Windham deliver the news.

GR: I didn’t know he was sick because he kept that quiet, which is his, of course, his right to do so. But I didn’t know anything about him. I only learned about Craig when I read his obit. I only learned that every single week, he drove a bus of kids who were disabled to Sunday school, that he was a Sunday school teacher, that he was really committed to helping poor communities and building houses on his spare time. I knew none of that, about this guy. It just really tore me apart to think, “I pass him every single day in the hallways and I say hello, and I didn’t know any of this about him.” And that’s the thing about stories. What you talk about is unlocking our vulnerabilities, our selves, our potential, and that to me is like… That’s the keyhole.

GR: When we know someone’s story and we know where they come from, we know what they’re about, we know the good and the bad, because How I Built This, it’s not a fairy tale. I want to know the things that you did that were stupid, I want to know the mistakes you made, I want to know when you kicked yourself, I want to know when you regretted things. Do you ever hear people in interviews, they’ll say, ” Brené, do you have any regrets in life?” And then the person will say, “No, I have no regrets.” And I never understood that because I have regrets, I think we all have regrets. Regrets are, to me, are very natural, and normal, and important.

BB: And I think they’re a function of empathy. Regret is our function of empathy. It’s looking back and saying, “I could have been kinder. I could have done something different.”

GR: And that’s the thing, it doesn’t mean that you’re going to love everything about that person. I think that there are people who have been on How I Built This who might still rub people the wrong way. But we know where they come from. We know more about why they are how they are. We know about their upbringing, and the obstacles they faced, and the challenges they faced, and the disappointments they encounter. And I love that because we all share that. The only obstacle is we don’t all know each other’s stories.

BB: Yeah. And to your point, I think when you’re a kid watching your parents… My dad was a tax attorney for an oil company, and then he had this huge entrepreneurial spirit, and it was interesting because he left that job and started his own business, and it was an oil-related business in Houston in 1982. Yeah, so it failed…

GR: Right before the bust, yeah.

BB: Yeah. And when you’re a kid, you just… You don’t know the story. You just know the implications of the choices that you’re living through right then. I related so much to that, you watching your parents toil at this table, and I would have been like, “God, I would have hated that.” I lived through that with my parents, but then that toiling, when I listen to your podcast, is my favorite part of the podcast. Do you know what I mean?

GR: We can relate to it, we can see ourselves in Jamie Siminoff of Ring going to his wife and saying, “I don’t think this video doorbell is going to work, we’re like three weeks away from going bust,” and his wife saying, “Well, let’s take a second mortgage out on our home.” Him recounting that story and crying because he really believed that everything he had done until that point, none of it really took off, none of it worked. It’s those stories where you’re like, my God, the Ring doorbell that everybody has now, this guy was freaking out just a few years ago about whether he was going to pay his mortgage? That’s real. And I think that we hear that and we say, okay, I’m not alone. I’m not alone.

BB: That’s… Oh my God, that’s right. I’m looking, and my sister’s in the room when I’m recording, so this is the impact this has on me. I wanted to listen to some of the episodes I had not heard of How I Built This. I work inside organizations so much, so I go for the ones if I either know the leaders or I’ve done work for them. So I’m reading… Is your wife’s name Hannah?

GR: Yeah.

BB: So I’m reading that Hannah is pissed off at you because she’s gone for a run and she gets back and she’s like, “Why didn’t you tell me about this episode? It’s so… ” And I was like, “What episode’s Hannah talking about?” So I listened to this episode about the Chicken Salad Chick. I’m so devastated by it that I call Barrett who’s laughing right now, because she’s sitting in the room. And Barrett, what do I say to you?

BG: It is hard.

BB: I’m like, it’s hard, but bring me Chicken Salad from Chick, because there’s one by her house outside of Houston. I was like, “I want the one with the dill, and I want the one with the cheddar and the bacon.” She’s like, “What’s this chicken salad obsession all of a sudden?” I’m like, “I just have to eat it. I know she’s sold the business, but I have to eat it for her.” Run through this story with us, this is such a great example of How I Built This.

GR: It’s such a hero’s journey. It’s such an epic story, and Stacy Brown is a wonderful person, and I’m still in touch with her and just spoke to her recently. She was a single mom, her ex-husband left her with nothing, and she had three children, a nine-year-old, a six-year-old, and a two-year-old. She had spent all that time at home raising the kids, so she never had an opportunity to have a job after college, she went to Auburn, and was living in Auburn, Alabama, and needed to make ends meet, she needed money. She was a pretty good home cook, so she started to make chicken salad and sell it to PTA groups and teachers’ lounges out of a cooler in her car. Eventually a family friend who knew her said, “Hey, this is pretty good stuff, we should partner up. I can help you, and we can get a little kiosk and maybe sell this out of a kiosk.”

GR: And they got a little 800-square-foot place in Auburn, Alabama, which was 300 bucks a month, and started selling chicken salad. And from there, the story becomes really, really powerful and devastating. There’s incredible success and growth and devastating personal loss, and not only almost the loss of the business from unscrupulous investors, but there’s love, and then there’s tragic loss, tragic personal loss. And today, Chicken Salad Chick is one of the fastest growing fast casual chains in the South. I think they’ve got 180 locations from Virginia to Texas today, and it started with a woman who was on her own with a cooler of chicken salad. It is such an incredible story, and it began in Auburn, Alabama, which is not a place where people think big companies are created, but it was the product of just an incredibly determined and genuinely kind person who built this amazing business and also had experienced incredible sacrifice, loss, and just devastating heartbreak along that journey.

BB: God, the story telling in every one of these podcasts, like I miss commuting and flying for this reason, when I’m walking… Because I just listened to it this morning. When I’m walking, I have to stop, and I’m sure my neighbors are like, “What the hell is Brené doing?” Because I’ll have my hands on my hips and I’ll be like, “No. No, sir.”

GR: Right.

BB: That is not how this story is going to end.

GR: Yeah.

BB: So one of the things we also share in common because we believe in the transformative power of story, we’re both drawn to the monomyth or Joseph Campbell’s Hero’s Journey. PS, I’ll just say to you that I love that you use the pronoun her when you’re describing it, because as someone who really loves that, it’s very hard because most of the stories that are used for examples are men.

GR: All men.

BB: Yeah. And so I love that.

GR: By the way, that’s why I love the new Star Wars because Rey is the hero.

BB: Yes. Yes.

GR: And my kids think of the Jedi as Rey. My boys do, and that’s amazing.

BB: That’s amazing. Like we need that, right?

GR: Yeah, yeah, yes.

BB: Because it’s my journey too. And so you talk about the call, it’s interesting. You talk about the call, the test and tribulations, and then the success in finding the wisdom and the return, right?

GR: Yeah.

BB: And so it was interesting because when I was doing some work for Pixar, I was talking to Ed Catmull about this, and he said… It was so funny. He said… Wow, we were talking about the second phase, the test and tribulations, and he said, “One way we think about it at Pixar is the protagonist will do everything possible that does not involve vulnerability to succeed, and it’s not until they’re forced into facing failure that they’re like, ‘Okay, shit, I’ve got to be vulnerable.'”

GR: Yeah.

BB: I’ve got to do the second mortgage like… What do you think about that?

GR: I think that vulnerability is… You’ve said this better than anybody else. It is such a foundational part of our strength, of the strength that we have within us. I think that increasingly leaders understand that. One of the things that in the past I’ve have had a challenge with on How I Built This is I do a call with everybody before they come on to the show, and I talk to people for the book too, so even before they were on the book, to get additional information. People who are a little bit older, let’s say sort of, 65, 70 and older, are still grappling with this idea of vulnerability, because…

BB: Totally.

GR: Leadership at a certain time was like the Jack Welch model, right? You pounded your fist on the table and that was the sign of a good leader.

BB: Power over.

GR: There was a model. And that has really evolved so fundamentally over the last 20 years where as for today, a leader who shows vulnerability is understood to be a leader who is also strong. I just had a conversation with Brian Chesky of Airbnb, who’s in this book, and we’ve told the story of Airbnb on How I Built This, and we just had him on for an update recently in recent weeks, and it was pretty remarkable. I said, “How are you doing?” That was my first question, it’s always my first question when we do updates. And he said, “How am I doing? Well, let’s see. I’m in my sweat suit, I’m staring into a green dot, and I have been staring into a green dot for 18 hours a day, every day, for the last six months, and I live alone and I miss my friends and we had to lay off a quarter of our workforce.”

GR: It was amazing. It was amazing to hear the leader of a publicly traded company be so open and vulnerable because that actually is what, for me as a consumer, and if I were a shareholder, would give me confidence in that company. I want…

BB: Totally.

GR: My leaders to show that kind of vulnerability. I want them to be open and transparent. Because it also means that the gears in their heads are kind of turning and they’re kind of working things out and working through things to get to a better place. So it’s been really interesting, because one of the main things we focus on on How I Built This is failure. And you know this, we don’t learn from people’s successes, and success is not that interesting, right? Hearing about whether it’s Howard Schultz or Branson or Sara Blakely, hearing their story as a series of just like leap frogs from one lily pad to the next of successes…

BB: Oh, yeah.

GR: A, that’s not true, and B, it’s not instructive, it’s not helpful for us, it actually further widens the gap between us and the people we respect and admire because we think, “Oh well, they’re just successful all the time.” But in fact, they fail all the time, and those successes are really hard-won. And it’s why sometimes when I interview somebody who’s over the age of 65 or 70 on How I Built This, they will ask me, they will say, “Why are you asking me about all my failures?” This actually just happened recently. I interviewed Dave Anderson, who is the founder of Famous Dave’s Barbecue. Okay? He’s a remarkable, fascinating man, he’s a Native American, and one of the few Native American, well-known entrepreneurs who really built a big business, a publicly traded business. And in the middle of the interview, he asked, he said, “Why are you asking me about my failures? Can we talk about my successes?” And I said, “Dave, we are talking about your successes, but your failures make your successes so much more meaningful.”

BB: Yes.

GR: And he really stopped and thought about that, and he said, “Okay, alright, I guess I’ll keep doing it then.” [chuckle] And that’s why. That’s why we have these conversations about vulnerability and failure and setbacks, because that’s when we can see ourselves in that person. In my job, one of my jobs, in the book and on the show, is to encourage people to keep going. Brené, I cannot imagine how many personal messages you receive every day over Instagram and Facebook and Twitter, and then your email, those people saying, “Your books have done this.” Like every time I think about being in the arena, I think of you, right? Me, personally. And when I lived in Washington DC, I used to love going to see the Teddy Roosevelt monument because I used to think of you when I’d go there and look at this man. He was a complicated man. A blood thirsty man that was very…

BB: Super complicated.

GR: A lot of the things about him are not easy to like.

BB: Right. No.

GR: But the arena idea is so powerful because it is true. It’s those who get into the arena, not the critics, that write history. So, so many people will write to you and say, “You’ve changed my life, you’ve kept me going,” and on a smaller scale, I get that too, every day. People who say, “I just read it before this conversation. We started the business two years ago, it’s been really hard. Listening to your show has kept us going, it keeps us motivated because we can see the light through the people you’re interviewing,” and that is an incredibly powerful feeling to know that the work you do actually touches people, moves people and improves a part of their life. It is unbelievable to know that I can do that. I’m sure you have the same feeling, to know that you can do that to people.

BB: I find it humbling and I find it, yeah, amazing sometimes. And I think… I have to be honest with you, as an accidental entrepreneur with a staff of 30 people, I had so many questions I needed your help with, just business advice. And I’m like, “He’s not a consultant, he’s not a consultant,” but I could see… You wrote… There’s a quote here that really sums up something that you do and help people that I think is interesting from your book, I have it on my list of quotes I wanted to talk to you about, actually, “Learning from other people’s mistakes is the only shortcut in the entrepreneurial world.”

GR: Yeah, yeah.

BB: And you’re doing that for people. That’s pretty awesome, don’t you think?

GR: I wanted this book to be like a yellow pages for mistakes.

BB: Yes.

GR: I wanted it to be that, because could you imagine every single mistake that is made in business or in life has been made a thousand times, not ever, that day around the world, like thousands of people have made that same mistake? And could there be a yellow pages where you just open up to that mistake and then you go and you hear about how somebody made that mistake and what they could have done to avoid that mistake? How amazing would that be?

BB: God, it would just be great.

GR: Because every…

BB: I want one for parenting, I want one for everything.

GR: Right? Exactly. Yes. [chuckle] And that’s what I’m, in a smaller way, what I’ve tried to do with the book, which is to say it’s a compendium of mistakes and also what ways those mistakes were resolved. And not just that, but how people thought creatively and think creatively about solving problems and about building ideas. I think we alluded to this earlier, but being an entrepreneur is not about hanging a shingle in front of your door, it’s a way of operating. I like to say it’s a mindset. I’m kind of ripping off Carol Dweck…

BB: Carol, yeah.

GR: Mindset. But I really do believe it’s a mindset because I am not a natural-born entrepreneur, at least I never thought of myself that way. Yes, when I was a kid, I had lemonade stands and sold things at garage sales, and I always had jobs, but I didn’t think of myself that way. I think most people, even many entrepreneurs, don’t think of themselves that way. The reality is, it’s a mindset. It’s a way of operating, it’s solving problems, it’s going around obstacles, it’s being creative, it’s coming up with all kinds of solutions. Like you have a staff of 30 people, there are entrepreneurial thinkers on your staff who are constantly coming up with ideas and ways…

BB: Thank God, yes.

GR: To get your message out to the world. And your research, you’re not just writing, inspiring content, this is rooted in serious science. So there are people on your team who are thinking entrepreneurially and creatively about how to do that. And the example that I always think of is the iPhone, right? That was invented inside of Apple by a team of entrepreneurs led by Jony Ive. So it really is a way of thinking, it’s a way of behaving, and they are all learned. It’s like anything, it’s like any… It’s like yoga. It’s like exercise, it’s a practice.

BB: It’s a practice.

GR: Right?

BB: Yeah, and here’s what I would say, this is a way I’m going to frame this up, so for those of y’all listening, you’ll hear this in the intro and you’ll hear it here. As someone who spends a lot of time in organizations working with leaders, more and more, the people I see rising into leadership positions, the people I see really getting great jobs, are people who have what they call a founder’s mentality or an entrepreneurial mentality inside organizations. That’s why I think the book is so important for MBA programs, because this is what we expect from people inside our organizations. This is what I expect from people. So all of a sudden, I’ve got 30 people working for me, I expect them to have a founder’s mentality, I expect them to be scrappy. We’re all working off agile processes, and I’m a research professor, but this is what it means to innovate.

GR: Totally. And also, it’s the increasingly good organizations are encouraging that. I am often asked…

BB: Yes.

GR: In normal times, I’m traveling around and speaking and meeting with groups of people who work for bigger companies, “Well, how can we do what Method Soap did?” Method Soap was invented, and we talk about it in the book, by two guys, Adam Lowry and Eric Ryan, in their group house in San Francisco. By the way, invented Method Soap, in the late ’90s, when everyone… In San Francisco, when all of their friends were like, “Wait, you’re living in San Francisco and you’re working on soap, not tech? What are you doing?”

BB: Not an app? Yeah.

GR: This is pre-app, but still this is like the web dot-com bubble. They were making a soap company. Well, they ended up creating this brand that took on Unilever and SC Johnson and the biggest soap companies in the world because they went in through the side door and they were unconstrained. They weren’t worried about people in their division saying, “That’s a dumb idea, that’s not going to work.” They didn’t have any bureaucracy to deal with, and that’s one of the challenges in big organizations, right? Because Unilever or Ford Motor Company or GE, they have the smartest people on the planet working there, so why is it harder for those companies to innovate as quickly as a few people working in a garage in San Antonio?

GR: Because of the structures that they’ve kind of put in place. But what I’m finding is increasingly, really smart, innovative companies are actually trying to break through and… Take the Google model, for example. They’re trying to create a disaggregated model where people work in smaller teams and people are given the opportunity to fail and people are given the opportunity to put forward ideas that are maybe a little odd or radical or maybe even silly, but still given the opportunity to put those ideas out there and to be heard. And I’ve seen this, actually, at Procter & Gamble, that was one of the last trips I made before COVID. And that’s a place where they are really trying to encourage that kind of thinking, because they have seen all these little start-up brands that have become huge brands that eventually they try to buy.

BB: I was going to say, eventually they… Yeah.

GR: Right. I think that’s one of the obstacles in a big company, but I think the way to break through it is to create space for people to fail and to put out radical ideas. And that’s also one of the things I hope How I Built This encourages people to do, to think in that radical way, because… And you know this. The thing that holds us back, the one thing that holds… And I’m not… I did not invent this idea, you can read about this going back to Dale Carnegie or any of these business books that have come out since then. The thing that holds most people back is fear. It’s fear of rejection, it’s fear of judgment, it’s fear of people saying, “That’s a stupid idea.”

BB: Being laughed at.

GR: It’s fear of people saying, “This isn’t going to work.” It’s why so many people in your world in academia don’t use their talent and skill to break out beyond the academic bubble, because they’re surrounded by their colleagues and they’re worried that they’re going to be judged.

BB: The shame risk is way too high in academics, yeah, because that’s our training, sadly, but I think there’s something so important in here. And for cultures, for leaders to ask, “What about our culture?” I love the idea of the entrepreneur mindset, because it is actually different than the founder’s mindset. They’re different a little bit. And I do love the idea of leaders saying, “What about our culture is inspiring an entrepreneurial mindset, what’s getting in the way, and what do we need to shift?” I do have this question. There’s like three or four questions I have to get from you, like I cannot let you go in good conscience without you… Okay. One, this is my big one. Is there any area where people just have to fail on their own regardless of the shit-ton of advice that’s out there not to do something? Are there any areas where entrepreneurs are just going to do it even though other people are saying, “God, I did that, that’s a mistake?”

GR: I think in practically every area. I think in practically every area.

BB: You’re killing me.

GR: Because look, failure is not the same for everybody, and failure doesn’t have to be a career-ending catastrophe. Failure can also be something that is a setback, that is painful, but that you could still recover from, and it might take some time. One example of this is like… One of my heroes is Sal Khan, the founder of the Khan Academy. And Sal just a genius. He had three degrees from MIT at the age of 21, two undergraduate degrees and a master’s degree. He was recruited by every hedge fund and quant fund, and he’s a math genius, and he did go work for a hedge fund and he eventually started his own hedge fund and it failed. He was losing tons and tons of money every month, and he knew the risks of starting a hedge fund, because he had been involved with hedge funds, and he still started one and it still failed at great financial cost to him when he was a younger man. But that actually… It reinforced the idea in his head that that’s not what he wanted to do with his life, but he had to do that. And we talk about it on the show, like he had to go through that failure to understand that that really wasn’t what moved him. What moved him was helping people get better in math and in science and in helping kids become better students.

GR: And when he decided to start the Khan Academy, everyone said to him, because he was in Silicon Valley, they said, “Sal, this has to be a for-profit. You’re so smart, you’re going to crush it, you’re going to be a billionaire.” And he was like, “No, I’m going to make this a non-profit. Because if we’re a for-profit, I know that I’m going to have to compromise on my principles. I know that eventually we’re not going to be able to give this stuff away for free, and there are going to be the haves and have-nots. Nope I’m going to make this a non-profit.” And for the first year he struggled to raise any money. He was just funding it himself, putting these lessons out online. Well, today, it educates 20 million people around the world for free. My kids use it for fourth and sixth grade math every day. It is such a gift to the world. Sal Khan could be a billionaire, he could be a multi-billionaire if he wanted to. He runs a non-profit. And I think that journey that he took required that failure. And I find that time and again, like sometimes even if you know the danger is real, you have to go through it. It’s like the Robert Frost poem, you kind of just have to get through it. Now, it’s not fun or pleasant, and it may not always be necessary, but in many cases, sometimes it is.

BB: It’s so painful. I know what you’re saying is true. I don’t want it to be true because then it would just bankrupt the whole idea of the hero’s journey if the hero could just use an algorithm to figure out what trials and tribulations to skip. But even when I’m listening to some of the stories, I’m like, “Oh God, don’t do that. Don’t do that. Don’t do that, because did you not listen to two episodes back, when someone else did that?” The 51%, like when I was listening to the one on Chicken Salad Chick this morning. I’m like, “Wait, what do you mean, 51% to the investors? No, you don’t know them.”

GR: No, don’t give them 51%.” I say that all the time. I’m in these interviews in real-time like, “No, don’t give them 51%, what are you thinking?”

BB: I’m going to ask this question because you may be the only person in the world I can ask it of. I don’t know the answer to it, and it’s a controversial question. So I am often brought in to organizations to help with culture around too much fear, there needs to be more vulnerability, because there’s innovation and creativity deficits, but there’s a lot of fear in the culture. Is there anything, in your mind, about the founder mentality, that some of these folks are just going to stay rogue? I think about myself… The same passion that drives my creativity can create an intensity in meetings and stuff that I know is not productive, like… What am I asking? Clarify, podcaster of history.

GR: Well, I think what you’re saying is that there is an energy and a passion and a propulsiveness that often comes with being a founder, having that founder’s entrepreneurial mentality. Because there’s a difference, you’re right. A founder and being an entrepreneurial can be the same thing, but they can be different things too. And I think for those with that founder’s mentality, it often comes with other qualities and attributes that enable that person to be driven and to seek out new pathways and to be a fount of ideas. But with that passion and intensity also comes… It can make you a difficult person sometimes.

BB: Yeah, that’s what I’m asking.

GR: It can make you unpleasant sometimes, it can drive the people around you kind of crazy because of your demands and your expectations. And that really comes from the expectations that founders have of themselves, because ultimately I find with those kinds of people… And I am one of those people, and you are too… We judge ourselves more harshly than anybody could possibly judge us. You’ve talked about this, we are our own worst critics. Our inner monologue can be really poisonous sometimes, and to tamp that down or to address that requires a lot of work and effort and self-reflection, and it’s not easy. But I also think that it’s possible to kind of mitigate some of it by being open and honest with yourself and also accepting and asking for… Not just accepting, but asking for people to be honest and open with you.

GR: I have a wonderful, incredible relationship with my editor, Neva Grant on How I Built This. I’ve worked with Neva for 20 years. She’s the most incredible editor in audio journalism, okay? Neva and I fight like cats and dogs. Brené, if any of our listeners… If you heard our conversations, you might be shocked because we go at it over little lines of my introductions or arguments over certain edits, and it comes from a really devoted, dedicated place. We’re both so devoted and dedicated to the mission of what we do. And every once in a while, it’s happened where I just get really mad and Neva just gets really hurt or just kind of taken aback at the way I’m expressing an idea and I just stop and I have to say, “I am so sorry that I spoke to you in that tone.” Because I have so much respect for her, she is one of the most important collaborators I’ve ever had in my career. And the thing about her that is so wonderful is that she is very direct, and she will call me out.

GR: And she also protects me in the sense that by her calling me out, because we are at the same level, we’ve worked together for so long and I trust her so much that she absorbs a lot of that kind of intensity that could, in another circumstance, go to the other members of the team, which I wouldn’t… You don’t want to happen. And so I’m very lucky that there’s somebody… And I can give her feedback too that way. And so I think that for me, the way I have tried to mitigate it is by asking for that feedback and really working on myself, it’s very hard. There are some strategies that I use, I exercise every day. I’m not great at meditation, I wish I was better [chuckle] The one thing I’m always very conscious of in any interaction, even intense ones, is respect. I have so much respect for the people I work with, and respect has to be… I think intensity is okay, having that energy and that fire is okay, but as a founder, you need to… I need to constantly interrogate your approach, and ask yourself, “Is this fair to the people around me?”

BB: So that brings me to my last question before we get to our rapid fires. And I’m really curious about this, man, I just… I could ask you a million questions. I really do love this book and this podcast, it’s kind of an empathy machine a little bit, and also a self-compassion machine, if you’re trying to do something similar. What role do you think self-awareness plays in a successful entrepreneur?

GR: I think it’s hugely important.

BB: Yeah.

GR: Now, it can be a double-edged sword, right? Because sometimes those who are extremely self-aware and extremely conscious of their own limitations are sometimes people who are unwilling to take the kinds of risks you need to take because they’re so realistic, they’re so self-aware that they…

BB: [chuckle] Oh my God, this is so interesting.

GR: Right. That they actually don’t believe in the things that sometimes you have to believe like the impossible things to get through it. At the same time, the reverse of that is even more destructive, an un-flailing belief that you are right and everything is going to work out. I mean, that’s the story of this presidential administration. I mean, look at all the people in there. Right?

BB: Yeah.

GR: Those are the kinds of people operating in that White House.

BB: Yeah.

GR: So to me, there has to be kind of the ideal place, is a balance between healthy self-awareness, but also an ability to have faith that you actually… It’s sort of like doing push-ups. Once I get to push up 24, I’m thinking, “I’m never doing another push-up.” But you can kind of will yourself to get to 25 and then collapse for a few seconds, before you have to go back to it. And that’s the thing, I do think that we all have to be self-aware and have a realistic ability to kind of step on the balcony and look down at the dance floor, we among them, among those dancers. But also have the faith to say, “You know what? I got this, I can do this and I’m going to do it.”

BB: God… You know what’s coming up for me when you say this? Are you familiar with the Stockdale Paradox?

GR: Yes, I am. Yeah.

BB: Yeah. So Admiral Stockdale said, “It’s the combination of being kind of brutally realistic about the facts, and then also never giving up that faith.” So we call it in our organization, gritty faith and gritty facts. But I never thought about that around self-awareness, but you’re right, you have to be able to see the dancers, but you can’t ever stop believing that you can pull that twirl off. Right?

GR: Right. Right. Right.

BB: Dang. So glad I asked you that. That was really good. I’m going to use that in everything. Okay. You ready for the rapid fire?

GR: I’m ready.

BB: Okay. Fill in the blank. Vulnerability is…

GR: Essential.

BB: Two. What is something people often get wrong about you?

GR: That I’m more interesting than I am.


GR: No, that’s a thing, that’s right. Yes, yes. That’s right.

BB: Is that true? Okay.

GR: That I am more interesting that I am. Yes. They think I’m more interesting than I am.

BB: Okay. I don’t buy it, but okay. Three, what is one piece of leadership advice that you’ve been given that’s so remarkable, you need to share it with us or so crappy that you need to warn us?

GR: The most important piece of leadership advice that I have received has been that great leaders simply enable the people who work with them to do the best work possible. And so for me, what it means to be a great leader is to be a great cheerleader, it really does. I spend a lot of my time being a cheerleader for the people who I work with.

BB: What is one stereotype or myth of leadership that we just need to let go of collectively?

GR: That it should be done by white men.

BB: Amen, brother. Okay. What is your best leadership quality?

GR: Empathy.

BB: What’s the hard leadership lesson that you have to keep learning, and unlearning, and relearning?

GR: That details actually do matter, and as tedious as some of those details are, and as much as I want to avoid them, I have to sometimes, or maybe more than sometimes, get in the weeds too.

BB: That’s so hard. Okay. What’s one thing you’re really excited about right now?

GR: I’m really excited about making more kids shows, which we plan to do in the next few months.

BB: Love that. Tell me one thing that you’re deeply grateful for right now.

GR: My wife. Always. Not now, not yesterday, always. I’m really lucky.

BB: Hannah, huh?

GR: She’s my best friend. Yeah. And my kids too, of course, but… [chuckle]

BB: Yeah. Okay, so you gave us five songs that you wouldn’t want to live without. So “Mia” is by…

GR: By Bad Bunny and Drake, featuring Drake. Yes.

BB: “Pray For Me” by…

GR: Kendrick Lamar and The Weekend.

BB: “Life and How to Live It”?


BB: “The National Anthem” by…

GR: Radiohead.

BB: And “Maps” by…

GR: The Yeah Yeah Yeahs.

BB: In one sentence, what does this mini mix tape tell me about you?

GR: I’m connected to all of these songs, not necessarily because of the songs, and whether they’re great or not, but because all of these songs remind me of a time and a place that was meaningful and that brings meaning to my life. And when I think of those songs, I think of those experiences and they make me happy.

BB: I love that. Well, thank you for this amazing book and the podcast, How I Built This. I hope you keep building incredible things. I love that you’re doing stuff for kids because there’s an intimacy and a different kind of neural pathway thing that happens with audio versus the screens, which can suck us in and numb us out, I think in a different way, so I’m really grateful for your work. And thank you for spending time with us on the Dare to Lead podcast.

GR: Thank you so much Brené.


BB: God, just such a great conversation. Is there anything better than listening to real stories about how just regular people like you and me, came together and built something that is meaningful and something that lasts and something that does good. I just… I go back to this thing that stories are just data with a soul and they make us so much better. And I think for me, not only do they make us better, I think the most instructional lessons that I’ve learned in my life have come through the transformative power of story. And this is Guy Raz’s sweet spot for sure. If you want to follow Guy, you can find him on Twitter @guyraz, G-U-Y-R-A-Z, same on Instagram guy.raz, and then Facebook and NPRGuyRaz. And speaking of great storytelling, I want to hook you up with the latest podcast on Unlocking Us, where I interview Gabby Rivera, the first Latina to write for the Marvel comics series and author of an amazing debut novel called Juliet Takes A Breath, which will actually take your breath away.

GR: I appreciate you listening to the Dare to Lead podcast. I just… Oh, I love learning, and I love learning with y’all, and I love being curious, and I love how many smart, caring, generous, vulnerable, real people there are in the world who we can learn from. So I’m just feeling very grateful. Y’all stay awkward, brave and kind. I will see you next week. And again, thank you so much for being on this journey with us. It’s just, it’s fun I feel very lucky. Dare to Lead is a Spotify original from Parcast. It’s hosted by me, Brené Brown. It’s produced by Max Cutler, Kristen Acevedo, Carleigh Madden, by Weird Lucy Productions. And the sound design is by Kristen Acevedo. Music is by The Suffers, the song that you’re hearing that’s just so great, Take Me To The Good Times.


© 2020 Brené Brown Education and Research Group, LLC. All rights reserved.

Brown, B. (Host). (2020, November 11). Brené with Guy Raz on How I Built This. [Audio podcast episode]. In Dare to Lead with Brené Brown. Parcast Network.

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