The #1 SKILL Every SUCCESSFUL Entrepreneur MUST HAVE (Explained!)| Guy Raz & Lewis Howes

In this episode of the School of Greatness, host Lewis Howes interviews veteran journalist and podcast creator Guy Raz. The conversation explores the core skill that distinguishes great entrepreneurs: the ability to endure and learn from rejection. Through stories of founders like Calendly’s founder, Spanx’s Sara Blakely, and Mormon missionaries, they illustrate how repeated exposure to "no" builds a mental muscle that fuels persistence. They discuss whether entrepreneurship is driven by mission or money, emphasizing that purpose, community, and personal values outweigh financial gain for most founders. Guy shares personal failures—including missing a coveted NPR anchor role and pivoting to the TED Radio Hour—and how those setbacks redirected his career toward podcasting. The dialogue also touches on broader themes: the role of failure in personal growth, the psychological fear of losing loved ones, identity shifts during crises (e.g., pandemic, remote work), and the importance of curiosity, fatherhood, love, and truth as guiding principles. The episode concludes with a “Three Truths” segment where Guy distills his life lessons into fatherhood, love, and truth, and defines greatness as influencing others with kindness and responsibility.
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Failure and failing is crucial to growth. It's absolutely fundamentally crucial. It's like a part of you has to be defeated in order to be reborn in a stronger way.
I think you gotta have a dream.
The School of Greatness.
Really?
Yeah. Please welcome Lewis Howes.
Welcome back everyone to the School of Greatness podcast. Very excited about our guest today. He is the legendary Guy Raz in the House, the host of how I built this, which is one of my favorite shows all about entrepreneurship, building businesses. And you are, I feel like you're the face of public radio, but you can't really say that you're the face, but you're kind of like the voice of public radio for a lot of people who listen on NPR and into your podcast. So, so glad that you're here, man. You've had so much success over your career as a journalist and you do an amazing job of getting to the heart of what makes people ticked. So welcome to School of Greatness.
Thank you. Thank you so much for such a generous introduction and for welcoming me.
Of course. And I want to get into it about entrepreneurship because this is something you focus on a lot. I've got a big entrepreneurship audience as well. And before I ask more about you, I want to talk about just what you've learned with entrepreneurship. And this is going to be either a very vague, broad question or something that you know the answer to right away. And I'm curious, what is the one thing the main thing that you feel from all the interviews you've done that makes great entrepreneurs great?
There's a bunch of answers to that question and some of them are predictable like resilience or a strong sense of optimism, you know, the ability to get back up when you get knocked down and those are all true, like you have to have that. But the one thing, because not every person I've interviewed has go to college or is educated, they're not all book smart, they're not all charismatic, they're not, you know, they're different, they're like us, right? But the one thing that binds every person I interview is they all either have naturally or have learned to develop the ability to withstand rejection, to accept, to basically accept that lots of people are gonna say no, and keep kind of grinding through it.
It's one of the hardest things is to deal with rejection, deal with people judging you, deal with people saying that like this is bad, this is horrible, this isn't going to work. It's because you want that confirmation. We want confirmation when we're doing something of like, yes, you're amazing, go do it. But when everyone's saying no, and you can go through it, because at some point, great entrepreneurs are going to get people to say no.
Yes.
You've got to learn how to get through it.
I never met this guy, Topio Otana, a couple weeks ago, and he founded this company called Calendly. Have you ever used Calendly? It's really great.
I mean, everyone for podcast interviews, it's like all we do is schedule.
It's about that. Yeah. So he started this, I don't know, like six or seven years ago, and his first job while he was a college student was selling ADT home monitoring services door to door, right? So he's in Athens, Georgia, and he's this kid who's from Nigeria. He came to the US and he was 16. And he's going door to door in Athens, Georgia, knocking on doors, trying to sell people home monitoring systems. And I said to him, I said, didn't you ever get discouraged with all those doors slamming in your face? Didn't you get tired of hearing people saying, no soliciting? And he said, no, because I knew that there was a hit rate. And eventually one of those doors would open and the person would say yes, and I would make a commission on that sale. And that was more money than I ever had in my life. So it was fine. I mean, it's a similar story with Sarah Blakely who founded Spanx. She sold fax machines door to door. She describes it as torture, but it steeled her when it came time to starting her business. She had to find a textile manufacturer that was willing to make a prototype of these undergarments that no one had ever seen before. And all of these textile plants said no until one finally said yes. But she was ready for that process because She had gone through like rejection exposure therapy.
Exactly. Yeah. Like she had a PhD in rejection for I think it was six or seven years she was doing door to door.
Yeah.
And do you think it's harder for to get successful or to stay successful as entrepreneurs? Is it easier to like, okay, I made something work with this success or is it easier once you get there to maintain?
It's a great question. I mean, I haven't put a lot of thought into it, but here's what I would say. I think Getting to a place where you have found some success, it's sort of like finding lift. It's like when an airplane takes lift. And then you hit cruising altitude at 35,000 feet and there will be turbulence. But I think that in general, in my experience, I think once you have achieved some level of success, it's easier to build on that because people have seen you succeed in some fashion or form, like what I do, what you do. I mean, 25 years ago when I started out on radio before I was podcasting, I couldn't get on the air. Why would somebody give me a chance? I had no track record. No one knew who I was. Nobody knew if I was any good. And I sucked, by the way. That's how it is. You suck when you start. You suck and then you suck less and then a little less and a little less. But once I started to go on air, it was like that domino falls. And other people was like, oh yeah, oh yeah, yeah, you can do a story or sure, we'll take your pitch. And it's the same thing with, I think, with entrepreneurship, which is once you, it doesn't mean that you're gonna, if you start a building, like, is Kevin Systrom gonna be able to found another billion dollar Instagram? Probably not. I mean, but, Will he continue to be successful in any endeavor he does? Yeah, and he'll also have some failures, but he has that sort of, and most entrepreneurs who have achieved something, who've created something and built something, even things that have failed, they have that lift that keeps them flying.
And do you think anyone could be a thriving, successful entrepreneur? I mean, like sustainably making money and having a business with customers? Do you think it's possible for anyone? Or some of us? Just not wired because when I was a kid growing up, I was never into baseball cards. I didn't do the lemonade stand thing. I, I never made any money. I was like an athlete and I didn't know the concept of here's a value, here's a skill, go sell it, try to get some money. I didn't know that concept until I was 25 and I needed to make money until it was a necessity and there was no other way. And 2008 happened, there was no jobs. And I was like, well, I got to figure out what I'm going to do to survive.
Yeah.
Is it a thing that people can learn or is it kind of you either got it or you don't?
I'm a 1000% believer that virtually every skill that entrepreneurs have are acquired. Now, there are some people, like Mark Cuban is a good example of just a freak of nature. Like when he was in his teens, he read a book called How to Retire at Age 35. Okay? He wanted to become a, like he was determined to become a millionaire by age 30. he went, he picked a college program where he could graduate in three years to save money. He instantly went to Dallas because he thought there were opportunities there. He got a job bartending at night because he knew it would stuff his pockets with tips. And in the daytime, he started selling computer software. I mean, he was a millionaire by age 30, like he, but he's a freak of nature, right? In that sense, I think most entrepreneurs acquire these skills over time. I mean, let's go back to rejection for a moment. So, some people are just naturally easier with it, right? Like, you remember, you probably knew that guy in high school who would just ask a hundred people out on dates and he wouldn't care if 99 of them said no because he knew that one would eventually say yes, right? Yeah. Now, I was not that kid. You might not have been that.
I was not that kid. I was terrified of girls.
I was terrified, right? I was terrified of people saying, no. It's sort of a weird kind of example, but the idea of going door to door to sell something or pitching people on your product, going to investors, it's really hard. It requires the ability to hear no and to keep fighting. And one of the insights that I gained that I learned from the show is just in this weird, it's like this weird thing that's happened, which is that I have ended up interviewing A significant number of Mormon entrepreneurs. Now, Mormons are a tiny percentage of the American population, like 2%. They have a pretty significantly high rate of entrepreneurship in their community and their culture and also business success. So, what is it that they're doing differently? Well, they're doing something very different than pretty much every other population in America.
They're like door-to-door salesman.
They send their 18 year olds to a country around the world and they say, go live somewhere for two years and get as many converts as you can. You're gonna have to knock on a thousand doors to get five, ten people to accept the Book of Mormon.
And you have to learn the new language and speak a different language out of your comfort zone.
Perfectly. And you've got to pay your own way. And by the way, you have to be polite and gracious and friendly. You can't be like, why are you slamming the door in my face? Like you are a Mormon missionary. You're representing the church. you've got to be really polite and friendly and kind. So those kids go abroad for two years, they come back to the US, Utah, wherever, they start college, they're way more equipped than your average 21-year-old to start their lives and also to start a business. And it's a story that I've heard from David Nieman, the founder of JetBlue. It's a story, you know, I've heard from Joel Clark, the founder of Kodiak Cakes, the protein powder pancakes. He got back from his mission in Australia and he started this company, this business. He had no fear of going door to door to sell pancake mix. And so, I'm not suggesting that everybody become a Mormon. I'm saying that, what I'm saying is that it's a really interesting kind of case study. I don't think the church deliberately setting its young people up to be entrepreneurs, but it's setting them up to be independent. and so that's a learned skill. Mormons are not preternaturally more gifted in rejection of the ability to withstand rejection. They just had two years of it, so they're better at it. And I think all of us can kind of replicate that in a sense.
Yeah, I don't know if you've read the book Influenced by Cialdini or if you've studied any of his work, but it's essentially how to influence people and a lot of people use it in business and marketing for their sales pages and things like that. sites like Amazon use the strategies. One might be social proof, one is likeability, testimonials, all that different type of stuff. And I have a lot of Mormon friends as well who are in the entrepreneurial world and they just all seem to be successful. I'm like, I don't know, it's amazing. But it's like they all kind of follow these principles where, like you just said, it's like they're all very kind and people want to do business with kind people. They listen well. you know, so you always feel like you're the most interesting person in the room when they're just asking questions and listening. They are, you know, they usually come with a gift, like they'll give you, even if it's a book, it's like they're giving you a gift where you want to reciprocate the law of reciprocity. And it's like they're following these natural ways of like building connection and building anticipation and desire that just translates into their life in business in a beautiful way. So Yeah, I agree. And I think if everyone went door-to-door for a month, you would probably gain a lot of wisdom. But imagine having to learn a new language and go door-to-door for two years without your friends. You don't speak to your friends and family for I think six months at a time or something like that. Yep.
You were out of your comfort zone. Totally. And by the way, when I was a kid, and you know, this is in the, you know, in the 80s, like school fundraisers were going door-to-door to sell chocolate bars. Now, of course, they don't allow that anymore because of safety reasons, even though on every objective standard, the United States is a much safer country today than it was in the 1980s. But in the '80s, my parents were like, yeah, go sell your chocolate bars. And I would just walk around the neighborhood and knock on doors. And now I think it'd be a little bit harder. But kids were kind of exposed to that more than they are today. I feel like when I was a kid, not to say that it was better when I was younger, It's just to say that these are things that you can do, you can instill in yourself and in the people you know.
Why is it so hard for us to learn about how to manage rejection? If that's the main skill, the number one key to success for a lot of these people is the ability to overcome rejection. Why is it so hard for us as humans to deal with that?
Well, there's a really famous professor at Harvard named Ron Heifetz. He teaches a course on leadership and he has this concept where he basically, He looks at successful and highly effective leaders. And basically what they do is they're able to kind of step out of their own bodies and stand on a proverbial balcony and look down at themselves in the situation they're in. Like Barack Obama is a really good example of this. He can just remove himself from a situation and just look and assess the whole situation. And it's almost like you've hired an outside consultant to tell you what you're doing wrong. Most of us don't do that. It's very hard to do that. It requires a lot of practice and training. I don't do that, you know. And, you know, I think we tend to hope that the product or the idea or the concept that we're talking about will be validated by the people we know or even people we don't know because we believe in it. And I think for most of us, our passion and our belief and our connection and commitment to that can be fairly easily shattered if enough people are like, this sucks or this is stupid. But what I think this kind of rejection slash going to the balcony technique does is it enables you to take the long view and to say, no, you know, I mean, here's a great example. Tristan Walker, one of my favorite entrepreneurs I ever interviewed, he started this company called Bevel. Okay? Now, here's the thing that most white men don't know. Most white men who shave go and buy a razor. You get the Gillette five blade or.
Six blade or eight— Justin Mares: Mach 3, Mach 7, whatever.
Dr. Justin: and you like it because it has five blades and shaves your skin and it actually shaves under your skin. Well, if you have curly hair and many African-American men do, that's not actually good for your skin. And so shaving is really, as Tristan explained, It's very traumatic, especially when young black men start to shave because they-.
You- break out, you get bumps.
Razor bumps and scars. And there are no products that have spoken or have really been developed for young black men. And so he set out to build a razor. It's called the Bevel. And he didn't want it to be like this razor that you found at the bottom of the ethnic aisle. He wanted it to be like an iPhone. He wanted it to be a beautiful razor and a beautiful box that was right there next to Gillette and whatever else and was as premium. And, you know, he had a lot of people saying, there's no market for this or, you know, even though he knew that African-Americans spend more on beauty products proportionally than almost any community in America. He really, and what he said to me was, you know, I said, how did you, how were you able to keep going when you kept hearing no? When you, when, when there were people who were saying, you know, this is, this is going nowhere. And he said, I kept going because I knew that if I couldn't make this work, nobody could make this work. And it was never going to see the light of day. But I also knew that it had to see the light of day because I needed it for me. And I knew a lot of other men needed it for them too. And it's just such an inspiring idea, you know?
Yeah, I love this idea of, you know, the great entrepreneurs who find a problem for themselves or for someone close to them that they're like, okay, this doesn't work for me anymore. This doesn't work for this situation. And I need to find a better solution. this. That's where the idea usually spawns from. Do you think the greatest entrepreneurs are more focused on money or on the mission?
Look, I think without question, it's the mission. Okay, without question. And there's nothing wrong with pursuit of money. I mean, it's perfectly fine. And it's the engine of capitalism in a free market. But, you know, At a certain point, what I've found with the people I've interviewed is that money is really, at a certain point, there really isn't much more that it's really not going to improve your life much more. Stuart Butterfield, the founder of Slack, has a great explanation for what it means to be wealthy. You can go to a restaurant, order anything you want. You can basically go on vacation or wherever you want, and you're not worried about debt. And those three factors, basically his argument is once those are taken care of, you are essentially wealthy. I mean, you are an and there really isn't much else that's going to improve your, you know, your life or your anxiety or your feeling of security. And I think that most entrepreneurs, certainly the vast majority that I've interviewed, are 100,000% motivated by mission. I mean, here's And here's actually the best piece of evidence for that. A lot of founders will eventually exit and sell their companies, right? And I think a lot of people imagine that, okay, you have a company and then you sell it and then you've got $100 million and then you're going to go lie on a beach in the Caribbean and sip piña coladas all day, right? The reality is if you did that, you would eventually become very depressed. you would actually just begin to die, right, and wither. And most of the people I've interviewed, they want to work until the very end, until even when they have enough money for three generations behind them. Because it isn't about the money. It's about a sense of purpose. It's about camaraderie. It's about community and a mission. You know, I mean, this might be weird for some of your viewers and listeners to hear, but I used to be a foreign correspondent. I covered the Iraq War. I covered the Afghan Wars. I covered Israel-Palestine. That's what I did before, you know, this is 15, 20 years ago. And I spent a lot of time in Iraq, 2003, 2004, 2005. And every time I would ask, you know, soldiers, what is it that, like, why are you here? Why'd you sign up for this? You know? And they'd say, oh, you know, to serve our country and blah, blah, blah. I said, no, but why are you here? What is keeping you here? Because you know this war is problematic and it can't just be about the flag, it can't just be about, because you know, part of you knows that what you do here isn't necessarily gonna be reckoning, you know, people in the US are, they don't even know what's going on here. What is it? And you get the same answer time and again. It's to protect the guy on the left and the guy on the right. I'm here. to make sure nobody shoots him and nobody shoots him. That's, that's, it's, it's about connection, camaraderie, mission, purpose. And it's the same thing with business.
So you think what motivates people most is the connection of the idea or the product or the service to the people you're working with or your customers or media?
All of it. I think it's, it's like a Maslow's hierarchy, you know, all of it. And, and it's, it's the people you work around. I mean, how many times have you, have you encountered somebody who is very successful and then they left their job or they retired and then they don't have that daily interaction. They don't have, you know, this happens.
In sports a lot where you're, you know, as a former athlete, you, you see a lot of guys get depressed after they retire, and they might have been an All-Star an All-Pro bowler or whatever it may be, a Super Bowl champion made $10 million contract. But then within a couple of years, they're very depressed. They talk about missing the brotherhood or the locker room because of the camaraderie and the connection. And when you don't, when you have connection for so long and then you go in isolation, it becomes very lonely. Yeah, I'm sure that's that.
I'm, there's no doubt in my mind. I mean, just, I just watched that Michael Jordan documentary a couple months ago on ESPN. It's so, so beautiful and you know, seeing some of those old Chicago Bulls players, you know, the sort of the lesser knowns, not the Pippen's and the Jordans, but the lesser knowns. And yeah, I mean, you know, they're not, no one's hounding them for autographs. They're not getting on planes. They're not, I mean, some of that I'm sure they don't miss, but some of it is, it's being part of a team, you know, being part of.
Something bigger than yourself.
Yeah.
I'm curious, what do you think, Entrepreneurs are afraid of more fear of failure or fear of success?
I think that most of the people that I've interviewed, and I would take a sort of go on a limb and say most of us, I think are more afraid of failure, which is actually not a good thing. Because failure is especially manageable failure is something we all have to experience and embrace. I think that that We all in our minds have this idea of what it means to be successful. And the reality is that success is not, it's not an endpoint. It's not like you do something and then you wake up and you say, you blow the trumpet and say, I'm successful and that's it. It's like exercise, you know? Like I exercise every day. I don't love exercising every day. It's not that fun. But I can't just, like my kids will say, daddy, you're healthy, why? Why? Why? I'm like, you can't just like get to a point and say, all right, I'm healthy, I'm done. 'Cause then you start to decline the next day. And I think it's a sort of a similar concept, which is, you know, success is a constant process and a constant journey. You know, I think by nature most of us are more oriented toward succeeding and most of us fear failure.
Mm-.
But of course, that creates a whole other series of issues. You know, one of the things that I love about how I built this is, the people I talk to is, and I've said this on the show, I think failure is just infinitely more interesting than success. You know, we get a lot of, you know, you get a lot of pictures, and I'm sure you get these too from people who are like, hey, Mike, client, they were the Forbes 20 under 20, they were this, they were this, they were this, they were the Nobel Prize, you know, whatever, like all these accolades. And that's great, you know, like I'm totally down with that, but I want to learn from somebody who's like, here's where I screwed up. I'm gonna tell you what a dumb idiot I was.
Right.
Because that's when we learn. And I think that, and that's really where people are at their most generous when they're really kind of talking about their failures. And it allows us to kind of get a window into their soul that we need to have. to help us when we are struggling with failure.
What would you say is your greatest failure then?
Well, I'll start by saying almost every day being in this profession, there's some failure, right? Whether it's people not wanting to be on the show or whatever. I mean, obviously now it's gotten much easier as I've grown, but my dream, my real dream in life when I was a younger reporter was to be the main anchor, news anchor on NPR. I wanted to be the guy telling the news on All Things Considered or Morning Edition, you know, because I thought that was important. Like when I came to NPR as a, you know, as a younger man when I was 22, my parents didn't know what it was, you know, but I wanted, I think part of us, some of us are motivated by wanting to make our parents proud or whatever it might be. And so that was really what I thought I wanted to do. And I ticked all the boxes, you know, I was a foreign correspondent. I covered wars. I went to CNN and I was on television for two years covering Israel, Palestine. I covered the Pentagon.
You risked your life for this job.
Right. I got the weekend job. I did a fellowship at Harvard. I ticked all the boxes. I was the weekend anchor for the news program, the weekend host.
But I worked- you-'re so close, the weekend anchor.
So close. So close. But I wasn't chosen, you know, and that was a real blow for me. That happened in 2008. 11. And I thought, you know, maybe it was time for me to find a new career. I mean, maybe I wasn't cut out for this, you know?
Really?
Yeah, I mean, look, it was very, very hard because I really wanted that. And the reality is that in the news business, there are managers and programmers and executives, and they have their own vision. And it's a perfectly reasonable vision. And I wasn't part of that vision. And it was a time in my life where I really, was trying to figure out what to do with it. And just very luckily, TED, as in the TED conference people, had approached NPR and wanted to collaborate on the show. And I heard about it and I raised my hand and I said, I'll do that. And so I kind of left the news world in 2012, entirely left it. And that was a failure. And, you know, that was like, I mean, I still have emails from, you know, really prestigious colleagues in Washington, DC when I used to live there, who were like, you,'re going to do a what? A podcast? What is that? Who listens to that? Wow. Why would you give up hosting the weekend news program?
You're so close to the main show, yeah.
Oh, they would say, you have a massive audience and we did. We had 3 million people listening on the weekends on the radio. Now that's changed a lot. Obviously, the radio audience has been in decline. But so I kind of, I was kind of in the wilderness in 2012. You know, I kind of went into exile. And I didn't really know if Ted Radio Hour was going to be successful. I didn't know.
And this was launching as a podcast.
Yeah.
Yeah, because I started in January 2013, so you started in 2012.
The show launched in March of 2013, Ted Radio. Well, it was a relaunch of the show, really.
So we launched about the same time in a space when, and this was before there was a million podcasts like there is now, I think we hit a million podcasts on Apple. recently, and I think there was not even 100,000 shows or something, and it was something that you couldn't even find. It was like you had to go to an app on iTunes and plug in your phone. Yeah, it was. Yeah, we were getting on when no one was listening, essentially. There was a couple of that big people before us, Joe Rogan's and some other tech podcasts, but it wasn't a big thing yet.
Yeah.
So you said, I'm gonna leave NPR, the biggest show that there is in this space, and go launch this little podcast thing with Ted.
Well, I mean, I launched it. I was launching within NPR, so it was.
Okay, got you.
Got you. But I left the news side of NPR, which was the most important part of NPR, right?
Is the thing that everyone knows about. And that's whatever.
And, like, if you're a journalist, that was what you wanted to do. you know, and I- It's like the.
Highest level of respect and highest ability.
Highest respect and it was Washington DC and it's, you know, all these things and here I am doing this podcast and like, you know, it's like the backwater of NPR at that time, you know? Of course, now the tables have turned a little bit but that was really an enormous failure. But here's the thing, as with almost every failure I've had, It has happened for a reason. It's like a hidden blessing. It's like if that didn't happen and I pursued that path, I don't know how happy I would be doing the news, especially today. I think the news is just really hard. It's a hard time in our country. News is really important. I have a lot of respect and admiration for my colleagues who do that, but that failure really kind of saved me.
It's interesting you say this is the more I hear about this and think about it, I reflect back on all my challenging times, adversity times, whether it be personal life, relationships, career, business, sports, and just like injuries and asking why did this happen in the time, but always when I think forward and I give myself hindsight now a year out from that moment, something always good seems to happen if I lean into the moment, if I embrace if I find the higher purpose and meaning, if I take the next step. I'm curious, so 2012-13 you were looked as like a failure, but it's given you so much because you leaned into that. Do you feel like you need to fail more then in order to take it to another level and you need to be criticized more, judged more, looked down upon from colleagues? Is there things that we need to be keep doing? to embrace failure?
I mean, look, I think nobody wants to be looked down upon and judged. And because it's hard, right? It weighs on you after all.
It's not fun.
I think we all crave, we all want to do something that people appreciate and enjoy. Criticism is really important. I think giving criticism is hard. And I don't think a lot of people are good at it, you know, most especially in the era of social media. Like, criticism is really actually abuse. right? But constructive criticism is great and super helpful. I mean, I think that for the most part, we all really need to understand that failure and failing is crucial to growth. It's absolutely fundamentally crucial. a part of you has to be defeated in order to be reborn in a stronger way. You know, this is a concept in nature, you know, that we have to withstand strenuous and difficult things. And they may not be physically strenuous or physically difficult, but emotionally, you know, and I think that there's really something to that. I mean, the other side of it is that I don't know if we constantly need to seek out failures just for the sake of failing, but I do think that there's something really powerful about failing and about figuring out how to harness that energy into fuel inside of you to just push you. It's really hard. It's taken me four decades of my life to be able to develop this, but to use it to kind of fuel just a real desire to make it, to succeed, you know? In some people, it's manifested as anger, which can also be destructive. But I think that if there's a way to kind of harness that energy to drive your passion, you know, it's not a great example. But Michael, going back to Michael Jordan again, you know, his famous Hall of Fame speech, right? Where he talks about all these slights throughout his career, which is crazy because I mean come on. He's the greatest basketball player of all time. Does he really have to complain about slights? But you know, he says, oh, Dean's coach Smith didn't start me or this coach didn't pick me or that player said this. He's like, it was just another log in the fire. You remember that speech? Yeah, of course.
Another log in the fire. Now, that's similar to Tom Brady. Like Tom Brady kind of lives with it. I was one, you know, I was in draft in the first few rounds. I wasn't a starter. I was all these things where he still kind of lives with that fire 20 years later in this season.
And, and, but the thing about Tom Brady and even Michael Jordan, I mean, is that they also benefited from luck, right? I mean, Tom Brady's case, the guys before him got injured. And, and of course, he had to have that luck in order to, and he had to embrace that and, and capture that luck and then kind of rise to the occasion, which he did. But I under, I understand that. I mean, I understand that kind of, you know, that feeling of being an underdog and kind of motivating you to push forward. And I think if it's done right, it can be healthy. It can also be unhealthy if it's not done right. You know, I think, and while I have so much admiration for Michael Jordan, that Hall of Fame speech is, you know, it's a little bit problematic because, you know, at that point in his career, he's got to stand up and say, I'm the greatest, you know, he knows he's the greatest of all time and everybody in that room did, too, you know, and be gracious.
Yeah. I'm curious, what's the biggest fear you still haven't conquered yourself?
It's sort of hard to pinpoint a specific thing because like, would I ever go bungee jumping or parachute out of an airplane?
More like an internal fear. Not a fear of heights or spiders type, but a psychological fear, let's say.
I mean, I covered wars. I covered five wars and was in several really scary situations. As a reporter, for some reason, I never really experienced, I mean, I was often nervous and scared, but never kind of scared in a debilitating way. Like I could make it through. It wasn't pleasant. I think when I really got scared was after I had children. And I realized that for the rest of my life, I will always be worried about them. I will always, you know, my son, my oldest son who's now 11, Six weeks after he was born, we were in Florida and we took him to visit friends and someone held him and he got sick. He had a temperature, a fever, which is really bad if you're under three months old. Especially if it's meningitis because meningitis will kill a baby really quickly. We took him to a hospital in Florida and they instantly, before they do anything, they give babies antibiotics. If they're under three months, they just give them antibiotics just in case it's meningitis. They gave him antibiotics and we're waiting there and then like an hour later, an administrator from the hospital walks into the room and my wife is a lawyer and she knew that something was up. They had given him an adult dosage of antibiotics. Dr. No way. A 180 pound adult.
This was a... oh my goodness.
This is a 10 pound baby.
Oh my goodness.
So they, I mean, we got in an ambulance and they rushed us to Children's Hospital in Fort Lauderdale and we were there for four days just to monitor him.
Oh my God.
And they told us nothing. They were freaking out that we would sue them. So they buttoned up and they told, and me, I mean, we didn't know what was gonna happen. Could there be renal failure? I mean, it ended up okay. Ultimately, he's fine. But that was terrifying. And that never leaves, you know? When I travel and I'm away from my kids, you know, I have these irrational fears. And I think that it's just kind of part and parcel of being a parent and something that, for me at least, is something I don't think I'll ever conquer.
Well, maybe you're not supposed to conquer that fully. I don't know as a parent, I'm not a parent yet, so I don't know what that would feel like. But maybe you should always have a sense of checking in and making sure that they're healthy and happy and otherwise you're neglecting your kids. I don't know.
I check in with them every day. So, yeah.
Is there anything in your career or with your business or your shows or your books that you feel like you haven't overcome yet? Because you built this massive podcast empire. you're so well respected in the space. I mean, is there anything that you haven't overcome in that space?
I mean, look, I mean, there's lots of things. And I guess for me, the question is, what is it that I want to overcome? You know, as with anything, as with any business, as with any concept, you know, how I built this, there's always a, there's always the danger that people just won't be interested in it anymore. That it, you know, and I actually had that feeling when the pandemic started. I thought, oh my God, because right after the pandemic started, we saw a.
Drop off in our audience. So do we.
I think everyone saw a drop, right? And I said to my team and to my wife, I said, Is this economy going to mean that people are not going to be interested in entrepreneurship? Is this a tone-deaf conversation to be having? And I was really interrogating what I believed. Now, of course, it's been okay. It's worked out and our audience has grown significantly since then. But I will say that I don't take that for granted. I'm constantly trying to interrogate what we do because I know that eventually, there may not be interest. At the same time, I probably could, if I made other choices in life, be even bigger or make more money or do more deals, and there's a trade-off for those things. And for me, the trade-off is less time with my kids and my family. That's just incredibly valuable time. And so, I think that one of the things that I probably will not overcome is just scaling what I do even bigger because I need to have a manageable life. You know, I need it to be, and for me, it's like my number one priority and the source of my identity is being a dad. It's not being the host of how I built this.
Really? That's interesting. So do you feel like you'll say no to certain big opportunities potentially if it's taking too much time away from being a father for a six to 12 month window? Or would you maybe take on some of those opportunities?
Nope. no. And I've said, I've said no to some of them, you know?
Big, big deals.
Yeah. But, I mean, look, you know, I mean, I, I feel very fortunate, and I feel like I get to do, like, like what you do. Like, I get to do what I love. You know, I love what I do. It's so I get, I get to talk to interesting people and learn from them and take, take those ideas and lessons and apply them to my life, and that's, I that's worth a lot. It's worth a lot.
Yeah. What's missing in your life?
I think what's missing in my. Well, right now, what's missing in my life, of course, is connection.
Right.
With fam, with, with, with people in my immediate family. I, you know, we're, we're lucky because it's the four of us, my wife and my two children, so we get to be together. But I, I think that. If there was anything missing from my life, it would be, I'll just say it at the risk of offending some listeners and viewers, but it's not just what's missing in my life, it's what's missing, I think, in the lives of a lot of us, which is, I'm really sad about the state of affairs in our country. I'm really upset about it. I think that our country is better than this. I think that we have really destructive and cruel leaders and people in the White House who are just mean. They're just cruel. And that distresses me. I lived overseas for eight years and people around the world really were inspired by America and about and by the ideals that we have and we talk about. And so much of that has really been kind of called into question in the last four years. And much of that has to do with the behavior of the current occupant of the White House. So that's what I'm missing. I'm missing better leaders for a country. And I'm hoping that, hoping we'll have that.
Yeah, it's been really challenging for me. I'm such a, in-person connection type of guy where I just want to be around people. And so, it's, you know, it's a challenge to completely, you have to shift your identity in a time like this to say, okay, because if you say, I'm a people person, I'm around people, you're always going to be suffering or struggling if you're not having what you want. So, I almost need to mentally shift my identity and say, I am with me and my girlfriend and we're just not going to see people or it's going to be with the distance or it's, It's just not going to be the same way and I need to be okay with it. Otherwise, I will suffer by holding on to this identity that I no longer have in this moment. And hopefully we can go back at some point and I can re-enter that identity that I loved.
Louis, you are an extrovert.
Extreme extrovert. And I love people. I love to just sit around and listen to people, hang with people, play sports with people. Love it. And, to not have that is like taking away oxygen in my lungs. And so it's very challenging when you're used to having something and you don't have it in general. And so we've got to constantly shift, otherwise we'll be miserable and unhappy.
Right.
So I've had to learn how to enjoy, as opposed to going to workout classes or the gym, I'm like a distance runner now, which I never wanted to be because I didn't like distance running, but I'm like enjoying the process of the struggle, the pain and like, okay, what can I gain from this? And I'm enjoying isolation more and being alone and what can I gain from this as opposed to this is killing me and this is, it's not fun, but it's, you gotta do it.
Right.
So my girlfriend's in Mexico right now because of her visa, because it's very hard to renew her work visa right now. So she's there for a month. I'm supposed to go visit her, but I may not because of Corona and it's like, I may not see her for three months. I don't know. That's not fun to do a FaceTime relationship. We've all got a, I think identity is a big thing. We got to constantly be willing to shift it if we want to be happy. And you being this identity of like, okay, I'm the weekend guy and I want to be the morning guy, but you shifted your identity into trying something else and you were able to create incredible results that impacted people with this new identity. And I think that's something that's really inspiring that you've done. what do you think has been some of the keys to the podcasting world is a world that so many people are trying to get into now. It is an entrepreneurial business in itself, people that have podcasts. I've built my entire business off of the podcast and I have books and I have events and courses and membership and all these different things. But it wouldn't have happened without a show and an audience that said, we want more. What do you think has been your success to building this platform, especially when it wasn't big, and then when you launched how I built this, and how did you continue to rise after the kind of dip in the early pandemic?
One of the things that I would say I agree with you, that there is an entrepreneurial, real entrepreneurial sort of element to podcasting. And in some ways is why I wrote this book. How I built this because I wanted to kind of offer a roadmap for people who want to build a business or are thinking about it or just want to be inspired by the stories of people who've done it. And I think that, you know, in our case, really what we're doing is, is, I mean, it's very similar to what you're doing, right? It's a simple conversation. It's a single narrative. And we're basically telling a story over the course of that hour. And it's designed, really deliberately designed to, to kind of send a to signal to the people listening that this person is not that different from you. You know, the only difference is that they put on the cape, they went into the phone box and put on the cape, you know? Right.
That's what- They went for it.
They went for it. And that's what I want people... I want this show, I want how I built this to inspire people to think that way. Because I actually, I really believe, and you know, again, one of the sort of motivating factors behind writing a book was, Like, I believe in entrepreneurship. I think it's an incredibly fulfilling way to live your life. You are in control more or less of your own destiny, right? And you're your own boss. And you're also often employing people and providing a good living for other people. I mean, it's actually a great way to live your life. And most of the time, when I think of somebody who listens to the show, I'm not thinking of people who are scaling mega-billion-dollar companies. I'm thinking of somebody who's got an Etsy shop, or somebody who's running an HVAC company, a small business that is doing something for the community or is meaningful to people or is employing people. That to me is what it's all about. And I think that with our show, what we really did was, especially after the pandemic was, we just followed our community. Our community was freaking out. Our community was saying, holy, what is happening and are we gonna survive this? Is my business gonna survive this? And so, pretty soon after we all went remote and my whole team started working from home, I said to them, look, we've got to meet our listeners where they are. Let's go on video. Let's do a live video chat. Let's bring on our old guests and just ask them how they're coping with the situation. Let's just build a community. And we just slapped it together on Facebook Live and now, you know, five months later, it's a show. It's how I built this resilience series. which we do twice a week. We've had, you know, just amazing people. We've had, you know, Stuart Butterfield from Slack and other people. We had Brian Chesky of Airbnb and he was really candid, you know, he was like, this has been the hardest thing I've ever had to deal with. I had to lay off 2,000 people. Oh, you know, it's been our thing home. Yeah.
No one's traveling. No one's. Yeah.
Their business went down 80%.
Wow.
In the first month, you know, of the pandemic. So, but it's been an awesome opportunity for our community and our listeners to kind of gather around and say, I'm not alone. You know, I've got, I'm watching this person and they may be at a different level. They're going through something similar to what I'm going. Yeah.
Yeah. What do you think is the hardest stage of entrepreneurship? The the kind of idea conception stage because everyone says, oh, I had the same idea five years ago. Is it the launching of the idea? Is it the, okay, now it's out there. How do we grow and scale it? Or how do we maintain the success? What do you think is?
Yeah. I mean, the easiest part about coming up with a business idea is coming up with the idea.
So there's a ton of, Great ideas.
It's the easiest part because you're at home and you might be talking to a friend and you're like, dude, I had this idea and you're like, it's gonna be amazing and everyone's gonna drink it. It's gonna be available at Walmart and at Target and we'll have these awesome logo and we'll have events and we'll go to the beach and we'll give it away and that's the easiest part of the business. The hard part is the next day when you actually start writing the business plan. and then you go into like try to seek out some funding.
Find a manufacturer, try to find a.
Manufacturer and then a distribution network. You know, there's a great African proverb. It is, it's something like the only way to eat an elephant is one small bite at a time. And this applies to a business. The only way to create and then sustain a business is to tackle one problem at a time. you do one and then you jump to the next lily pad and then you jump to the next one. And I think that's really true. I mean, and you know, that again, you know, with the book, I'm trying to basically put together all of the mistakes that were made along that journey to say, hey, every mistake has been made a million times a day. The same thing you're doing is already somebody already made that mistake and they figured out how to solve it. Here's the answer in the book. But really, it's this idea that you break it down one step at a time and it's hard. Building a business every step of the way is hard. Right now, you look at a company like Zocdoc, it's valued at $4 billion. You talk to Oliver Curaz, it's just as hard today than when it was valued at $1,000,000. It's really hard. I mean, bigger company, bigger problems. It's very successful, but they've kind of had to pivot because of COVID and focus on telemedicine. So I think that it sort of goes back to what I said earlier, which is you don't just reach a destination and blow the trumpet. It's a constant process of keeping that airplane at 35,000 feet.
There's challenges every year and you have to find the solution to those challenges constantly. Just because you've solved one problem of the initial idea doesn't mean there aren't a dozen other problems that come every single year that you need to reinvent how to solve and make a better solution too. So this is the risk of being an entrepreneur is the amount of problems that you need to solve and investment and money and time and energy into this one idea. But the reward can be very high because you paid the price for that risk if it works out. So that's the benefit and the cost, I guess. Your book is really exciting. I'm excited for this to be out into the world. It's called How I Built this, the Unexpected Paths to Success from the World's Most Inspiring Entrepreneurs. So people can go get that right now. They can pick it up. They can pre-order it. They can get it. It's all over the place. You're on Instagram, Guy Raz, Twitter as well. Is there anywhere else? And how I built this podcast is amazing. It's one of my favorite. I actually don't listen to many podcasts myself, but I listen to yours. Thank you. And I think it's very inspiring, well produced, the music, you do a great job in narrating and interviewing. So it's where I get a lot of my guest prep for the interviews I do because we have a lot of same people on our shows. And you've got the book, you've got everything there. Is there anything else I'm missing about how we can support you the most?
That's awesome. I mean, if anybody wants to buy the book or pre-order before the 30th of September, I will send you a signed bookplate, which I'll find on my website, guyraz.com, G-U-Y-R-A-Z.com, or howibuiltthis.com, and yeah, I mean, I'm in all those places, Instagram, guy.raz, Twitter, @guyraz, Amazing. I do my best to engage with people.
You're engaging on social media?
As much as possible. Not too much. Not too much.
But make sure you guys, if you enjoyed this, make sure I've got a couple questions for you to finish this off. But if you guys enjoy this, make sure to pick up a copy of the book. And also take a screenshot of this and post it on your Instagram story or post it on Twitter and tag Guy as well. Let him know.
And I will like that.
There you go.
I will.
Hopefully respond to you there. I got a couple questions left for you, Guy. One is called the Three Truths. I asked everyone at the end. So, imagine you've accomplished all of your dreams and you've lived as long as you want to live, but eventually you've got to shut the lights off to this life. You've overcome all the challenges and fears that have come your way. You've embraced them to learn and develop the new skills. and for whatever reason, hypothetically, you've got to take all of your body of work with you to the next place. So all of your recordings and books and audios and anything you've ever done, speeches, videos, they're all with you in the next place so no one has access to your content anymore. However, you've got a piece of paper and a pen before you shut the lights off on your life and you get to write down three things you know to be true from your existence, from your experience, from your life, three lessons you would leave behind and this is all we have to remember you by. What would you say are your three truths?
Fatherhood, love and truth.
Why fatherhood number one?
Because it's a hard thing to talk about because of course not everybody is a parent and not everybody has the opportunity to be a parent. And so I'm I try to be sensitive when I'm talking about it, but for me, it opened my eyes to the world again. I remember when my first son started talking and he would look at the stars and he would say, How long would it take us to get there? And I just thought, man, my mind is blown. That little kid just asked me a question that I haven't thought about since I was maybe five. It just reawakens your For me, it reawakened my sense of awe and it actually enabled me to do what I do today because I do what I do well because I'm a curious person and I'm a curious person because I choose to be. This is not a gift that I was given. This is not a special super talent. This is not something I have that other people don't. I choose to be curious. Anybody can choose that. having children helped me choose that.
That's beautiful. Yeah. I'm not a father yet, but I hope to one day become one. And I know there's gonna be a lot of beautiful things that come with that. So exciting stuff. Fatherhood, love and truth. What would you say is your truth?
My truth is, is sort of the North Star of, of what I try to be. I mean, look, all of us have and live different versions, slightly different versions of who we are. Right? And the best version of who I am, like, the best person that I am is the person I'm on how I built this. Like, that is the person that is authentically who I am, but at my best. And I don't always. I can't always be my best. Sometimes I'm in traffic and I'm frustrated. Sometimes somebody cuts me off and I honk my horn sometimes. you know, I'm about to get in a parking spot and somebody grabs it, you know, all the things that happened to all of us. But I really think of that version of me as the truest version of me and also what I aspire to be, you know? Because we can't always, we're not always kind, we're not always generous, we're not always forgiving, we're not always compassionate. But I think all we can do is try. to live that way and to be true to the values that we aspire to or that we, the way we sort of self define. And for me, when I think of truth, I think of it as an aspirational, like this is sort of an aspirational pursuit.
Yeah, it's beautiful. I want to acknowledge you, Guy, for for constantly showing up. You've been showing up for decades trying to serve people at the highest level from, you know, as a reporting on wars to now reporting on business and entrepreneurship and the human spirit. And I think you've set an amazing example in a bar for people on how to live a good life and how to do a job well and to constantly be curious. So I'm grateful for you. You're a big inspiration to so many, including myself. And my final question is, what's your definition of greatness?
My definition of greatness is making sure that the people that you have the power to influence inhabit and live on this planet with kindness and a sense of responsibility. And in my case, the only thing, the only job I have to do in life, it's not to make great shows, It's not to be a well-known podcaster, you know, it's none of those things. I have one purpose. It is to, as best I can, instill as many of the values that I think are important that I hold dear to instill those values in my children. And that if they grow up and they are kind and responsible and Good humans, like that is, I've done my job. That's it.
There you go. Guy, thank you so much for being here, man. Appreciate it. Make sure you guys go get the book. Check out the show. You're a legend. If you want more greatness in your life, then you gotta check out this video right here.
If you're walking in the direction of greatness, you walk in the direction of excellence, you're going to be uncomfortable. If you want to be an Olympic athlete, you got to get up early in the morning, you got to work out, you got to be uncomfortable for years. For years, periods of time.
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