Guy Raz talks with Jay Shetty about the risks of being an entrepreneur, the motivation behind every successful entrepreneurship, and finding the right co-founder who shares your ideals and beliefs.

Guy Raz is an acclaimed radio and podcast personality, described by The New York Times as “one of the most popular podcasters in history.” Perhaps his best-known show, How I Built This, features in-depth interviews with the world’s greatest innovators, entrepreneurs, and idealists, and the stories behind the movements they built. 

What We Discuss with Guy:

00:00 Intro
02:15 First thing Guy ever built as a kid
05:11 “Journalism gave me a psychological pass to talk to anybody” - Guy
10:13 The way we come across an idea is when we have a problem to solve
17:25 Motivation comes from solving a problem or fixing something
23:03 Chapter 3: Leave your safety zone, but do it safely
27:56 Risks taken and experiences gained while building a career
33:09 Master the skill to understand what you’re good at
37:04 Having a business partner is crucial when you almost want to give up
41:44 Give yourself time and opportunity to decide if the partnership is right for you
44:26 The common myths surrounding fundraising
50:20 Be an active listener to learn more information about the real story
53:50 The most outlandish story or pain out of 400 interviews done
59:55 What you’re missing out on when you think you’re not cut to be an entrepreneur
01:03:42 Guy on Fast Five

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There will come a time where you will want to give up, where you will run into a roadblock and you will say, is this worth fighting for?

It's better for me to just move on, give up.

But the person who you co-founded the company with will say, we got this, We can get through this.

And there will be other times where those roles are reversed, where you are the person with the optimism.

I have experienced that hundreds of times.

Hey everyone, welcome back to On Purpose, the number 1 health podcast in the world thanks to each and every single 1 of you that come back every week to listen, learn and grow.

Now today we have an extremely special guest because his ability to understand, assimilate and synthesize knowledge, insights and information about building successful businesses, about finding our calling and following that calling are just second to none.

Now I'm talking about none other than Guy Raz, the author of the new book, How I Built This, and the host of the NPR podcast of the same name.

He's a connoisseur of entrepreneurs, having interviewed hundreds of successful self-starters and researched what makes them successful.

For years, Guy was a foreign correspondent for NPR and was the youngest bureau chief ever at the age of just

I can't wait to speak with Guy today and share this conversation with all of you.

I remember just, I think it was a few months ago when we were just DMing on Instagram and you kindly invited me to do your live event for How I Built This, which was unbelievable and I'm so grateful for that opportunity.

But I've been more excited about today because I want to hear from you.

And so it was great when you reached out.

And I'm so glad that now we know each other.

And I want to actually start off with hopefully a different question than you get asked often.

And It's what was the first thing you ever built as a child how did your family friends parents respond to your first ever thing that you built.

I grew up in a a fairly traditional I'm not religious these days I have a lot of respect and immense respect for people who are religious and who are observant and practice religion.

But I grew up in a kind of an observant Jewish home as a kid.

My parents were immigrants and it was really important for especially my mom to keep traditions.

And so Friday nights were very important in my home as a kid.

That's the Friday the sundown, it's the Jewish Sabbath, and Saturday you kind of take a day of rest, foreshadowing I do that today but for different reasons.

And as a kid it was really important that our house was clean and bright and ready for the Sabbath.

It was just part of our tradition growing up.

And so I was expected to clean my room and tidy it up.

And every Friday afternoon after school I would spend hours building these elaborate villages out of Lincoln logs.

Lincoln logs – are you familiar with Lincoln logs?

It was a – they're still around, but it was a classic American toy.

Lincoln, Abraham Lincoln, you know, the myth was that he was born in a log cabin, which is kind of true.

And so they were these logs that had little grooves and niches in them and you could build these elaborate homes and structures out of them.

And I would build these villages in my bedroom as a kid for my dad when he would come home from work.

Who was not – my dad was not particularly observant.

It was my mom really who – but this was part of our tradition at home when I was a kid.

And so I would spend hours building these elaborate villages out of Lincoln logs and then eventually Legos.

Of course you don't think about that when you're 8 or 9 years old but it was a way for me to kind of express myself and also, you know, show my parents something I was proud of and then feel pride when they were excited about it.

I remember doing similar, I used to play a lot with Lego and Playmobil and some of this similar style of toys.

And I remember creating lots of villages and castles and boats.

And I actually miss it now that I'm talking to you

Yeah, I'm like, I want to go build a train track.

But Yeah, I need to go and get back into it.

And I feel when I go to places like, I don't know if you have that in the US, we have in the UK, we have Legoland, which is like...

Yeah, and whenever I go to those, I'm like, oh, this is so cool.

Like, there's just such a fascination towards building a city or a town out of something very small.

And I noticed recently also on Instagram, you posted an old Press Pass from your high school newspaper.

And so you've been a journalist and a reporter and a interviewer for a very long time.

Do you remember the first story you ever covered?

Again, I grew up having to go to Hebrew school.

You start off something that you do and then some people kind of, but it was really an important thing when I was a kid.

And I was the reporter for the Hebrew school newsletter.

So it was about some – it was like some – 1 of the classes did a performance and sang songs and I wrote about that.

I was a journalist kind of a – a journalist.

I was interested in journalism from a very young age.

And I don't say that to sound like some kind of precocious kid, it's not that I was precocious.

What it was, Jay, was that I am, have always been, as a kid I was, I still am, even though I do these very public jobs now, I am, and I think you have a lot of this too, I'm super introverted and actually quite shy.

I'm not the kind of person that can easily go into a room and just start shaking hands.

You know, it's a very American characteristic, by the way, the charisma, which is something that I can find and have found over time as I've had to do public things but it doesn't come naturally to me.

What journalism gave me was a pass, was this kind of psychological pass in my mind to talk to anybody.

You know, naturally, I'm not the kind of person that would just go up and say, hey, I'm Guy Raz.

But when I had a notepad in my hand, and this was going back all the way to high school, I could.

I felt like as a high school kid, I could go up to other kids in high school and ask them questions because it was for the newspaper.

And so I was doing a job on behalf of something bigger than me.

It was this idea that it was like it opened a world to me that I couldn't access without that notepad, that safety net.

That is such a brilliant way of thinking about it.

I feel like when I told you about how my parents forced me to go to public speaking classes, it wasn't that after I finished the classes, I was just happy being a public speaker.

It was not until I actually discovered the Bhagavad Gita and the Vedas and the spiritual texts that I studied, that I felt like I was speaking about something more than me and beyond me and far more fascinating and interesting than I was.

And so then I had the confidence to share it because I felt I'd come across this treasure mine of wisdom, and I had to share that wisdom with the world.

And so I can identify very closely with that.

I mean, it's this thing that it's Like, there's no explanation to it, because why did I feel empowered with a notepad and then eventually a microphone in my hand?

I mean, it just, something in my brain clicked, and it enabled me to feel safe and comfortable approaching people and having conversations and not being worried about being judged because I was gathering information.

And that was a strong gravitational pull for me.

It's what attracted me initially to this profession.

So yeah, I mean, I've got my high school press pass still to this day, I just happen to have it, but it really is what I eventually would do with my life.

Yeah, you've encouraged me to go dig up some old things from my life.

For anyone who's listening and watching right now, I'm talking to Guy Raz, How I Built This, The Unexpected Paths to Success from the World's Most Inspiring Entrepreneurs.

We've got the link in the description, so you can go and grab a copy anytime while we're listening, while you're listening.

Guy, what I'm fascinated by, and I was saying this to you earlier, I think you've done a phenomenal job of breaking down the entrepreneur journey.

I mean, you've done so many interviews with so many incredible people, and I can't imagine how you'd even start to write this book.

But I do want to honestly say that I thought everything from the titles to the chapters to the structure was just wonderful to see.

And I'm honestly, and I'm not joking at all, I'm thinking about pursuing a new business venture and I'm going to follow your book while I do that.

And I can't wait to tell you how it goes.

But 1 of the first things I wanted to talk to you about is a question I get asked a lot.

And it's about this ideas of like, how do I know if this is the thing I should be doing?

And I think we hear this a lot, and I'm sure you hear it a million times, and people are like, well, what do I start with?

Like, how do I know if this is what I love?

And you start off the book by telling people to be open to ideas.

Tell us about how someone finds the answer to that question.

Probably the question that people ask the most, I'm sure you get this question the most of almost any question, which is how do I know?

The answer is you don't always know right away, right?

And the reality is that most of the time, the way we come across an idea is because we have a problem ourselves, a problem we need to solve for ourselves.

As we begin to interrogate how to solve that problem for ourselves, it starts to crystallize in our mind that maybe that problem is a problem other people have and could solve other people's problems.

So a great example of this is my friend Tristan Walker who was on How I Built This.

Tristan is an entrepreneur, a brilliant entrepreneur, and he is a black man and He knew and knows that razors were not designed for most black men because most black men have curly hair and when they shave oftentimes the hair and their beard grows back into their skin.

And most razors in the United States and sold around the world by Gillette and other companies have 4 or 5 blades that are designed to cut the hair under the skin.

The problem is when it grows out, it grows back into the skin, especially for men with very curly hair, and it affects mainly men of color.

And he knew that this was a problem for him, And he knew it was a problem for his friends, but nobody was addressing this problem.

And in his mind, he thought, why isn't there a beautiful product, as good as a Gillette razor, as beautifully packaged, available in the same aisle where Gillette razors are available?

And That was the genesis of the Bevel razor, which is now part of the Procter & Gamble company, 1 of the biggest multinationals in the world.

They bought the company and Tristan is the CEO.

It's a great example of a problem that he needed to solve and that solved a problem for millions of men whose day-to-day routine was – in many cases, it was not just painful but it was also psychologically painful because of the scarring that occurred and just the physical pain of dealing with that.

And that is how you begin to come up with ideas.

You begin by interrogating your own problems, the things that bother you or that need to be improved.

Jay, how many times have you been somewhere, and I know anyone listening to this has experienced this, you're waiting in line somewhere for a coffee, or you're at a restaurant, or you're in a shop, and you think to yourself, God, they could do X so much better if they did it like this way.

Or man, you know, if they just tweaked that, then the outcome would be so much better for the customer.

That's when you start to kind of connect the dots and say, wait a minute, maybe I can do that.

You know, Howard Schultz loved coffee and he loved this 1 little coffee place called Starbucks in Seattle, but guess what?

They didn't sell coffee, they only sold coffee beans.

They sold great coffee beans, but you had to go brew it at home.

And so when he bought this little shop, he decided to turn it into something much, much bigger, which today is, I think, the second biggest food company in the world.

And it was all because he saw a problem that needed to be solved.

I think that's such a great place to start for anyone who's listening or watching right now because it's something you experience.

It's not something you have to think about, you don't have to do a brainstorm, you don't have to get a pen and paper out, you don't have to be reading lots of books, it's it's something that we do almost intuitively.

I think my biggest problem that I would love to solve right now is me and my wife never know what to watch on any of the streaming platforms And I spend every night like flicking through, like, do we want to watch this show?

And it's, we spend the whole night and I'm not coming up with a solution for this, but it is interesting that that would be a great starting place.

If I wanted to, because it's something that caused me a lot of pain on a daily basis.

I'm sure it causes a lot of people a lot of pain on a daily basis, at least friends that I know.

And therefore it would be a good thing to start on.

This is a huge challenge, discoverability, with not just with video content, but with audio content too and so many people are trying to figure out how to solve this problem because I think for most of us, we go by recommendations from friends.

You know, In my case, watching things is really challenging, Jay, because I am sort of a weirdo when it comes to watch, like, I don't like anything violent.

I don't love things, I mean, I'm personally very open to the world and to ideas, but I've got 2 little kids, so it's hard to watch things with a lot of sexual content or violence, or not only because they're around, but I don't really wanna see that.

I can't, like I appreciate Quentin Tarantino is a genius, but it's hard for me to watch his movies because they're so violent, even though they're sort of cartoonish violence.

Breaking Bad, I stopped watching it after 3 or 4 episodes.

It was too violent, even though it's amazing.

Like, I have a really hard time figuring out what to watch.

I end up watching like, you know, like a Wes Anderson movie or something that's fairly innocuous, you know?

I think the closest I've got to a solution is I really trust votes on IMDb.

So I believe that if anything is above 8 on IMDb, it's going to be epic and it always fits.

And if anything's above 7 on IMDb, it's usually a good watch.

If it's a 6, I'm setting myself up for a bit of disappointment at the end of the night.

And if it's anything lower than a 6, it is going to be the biggest waste of my time.

But I love your answer of starting with a problem.

It stops you from worrying about like, will this be successful?

You know, all the things that with the people you spoke to, and obviously, they all went from a problem point of view with a couple of examples that you've so beautifully shared with us and so many more in the book How many people were really?

Thinking or vocalizing or verbalizing their focus on the result How many people started with anything to do with the result?

I mean, the reality is that in virtually every case, for virtually every entrepreneur I've interviewed, they had a vision and an idea, and that vision and idea became something slightly or extremely different from how it started out.

I mean, you know, 1 of my favorite stories is the story of slack, right?

I have never interviewed anybody who is purely motivated by money.

Because if you're purely motivated by money, you're probably better off going into finance or getting a job as a lawyer because you will eventually make good money.

Being an entrepreneur is super risky in terms of going for the gold.

I mean yes, you can make a lot of money But virtually everybody I've interviewed is motivated by a problem and solving a problem and trying to fix something and or build something.

And the best evidence for that is the vast majority of people who sell their businesses after 10 or 15 years go and start something else or continue to work for the company that bought them out.

Because it's not the gold they're chasing.

I've interviewed people who have sold their businesses and then were kind of pushed out of the companies and they became very, very miserable because they lost that connection to the people around them, right?

So in terms of like thinking of an idea and it becoming something entirely different, I mean 1 of the best examples of this is Slack.

I mean this is a product now that is used By so many people, especially in the pandemic era, right?

Slack began as a multiplayer, massive multiplayer online game.

Stuart Butterfield wanted to create a game, a video game.

He is a gamer, he's a friend of mine, he's a wonderful person and he loves games.

And he brought a team together, he had already had a successful business called Flickr that he sold to Yahoo, so he had a track record, he got investors, He brought this amazing team, they built this amazing game, and it wasn't successful.

Nobody wanted to play it, even though it was a beautiful game, it was way ahead of its time, and this is 2012.

But what they realized very late in the game was that they actually built something entirely different, which was an internal communications network that allowed the software developers and the sales reps and the development people and the back-end people and the business people to communicate, just an internal.

But a friend of Stuart's from outside of the company saw it and he was like, this is amazing, can we use it for my company?

He's like, yeah, sure, here it is, here you go.

They did not realize that the revolutionary thing they were making was that.

But once they realized that they built something completely different that was really useful, That was the revolutionary product.

So sometimes the idea sneaks up on you, and you have to kind of go through the other stages to get there.

You know, we just did a story about, and I can talk on and on about these stories.

We did this story about the largest Mexican-American paleo food company in America called Siete Foods.

Started several years ago by a brother and sister from Laredo, Texas, Miguel and Veronica Garza.

They really started this out because they built a CrossFit gym in Laredo, Texas.

The family ran it and the CrossFit gym basically ran out of money in the end.

But, Miguel's sister Veronica used to make tortillas for the customers of the CrossFit gym out of cassava flour and almond flour because if you do CrossFit, there's a good chance you're eating a paleo diet, you're not eating grains.

But you're in Laredo, Texas, which is like 1 of the capitals of Tex-Mex food.

And if you love Mexican food, you're gonna eat wheat and corn and beans, Well, she was going to these CrossFitters at their CrossFit gym and saying, hey, do you wanna have a paleo tortilla?

So it began as a CrossFit gym, which eventually morphed into a food business.

I had no idea about that, and I love that brand.

Me and my wife love their sauces and their dips and their chips and like- They're incredible.

And we love them too when we don't want to eat grains or exactly what you're saying, like paleo diets.

I had no idea that was their story and I love how I love how you've shared that point about the pivot and the discovery of a product is not how you expect it.

1 of my favorite chapter titles that you have in here, Which in and of itself answers the question, but I really want to dive deep into it.

It's chapter 3 and it's called, Leave Your Safety Zone, but Do It Safely.

I just thought that that was just told perfectly because whether it's in being in my own journey or when I'm speaking to people.

And again, the number 1 question is, well, when do I know to quit my job?

Like, should I quit my job and go all in?

Is it because I'm not all in that it's not working?

Or when do you know that, you know, now it's time to bootstrap and get stuck in?

And when you wrote that chapter, leave your safety zone but do it safely.

I I wanted to understand how does someone practice that?

How does someone bring that into reality?

Because I think at 1 point or another, Everyone gets to, okay, I know what my problem I'm trying to solve is.

I've started the process, we've started to create something.

But now it needs momentum, it needs money, it needs investment, it needs whatever else it needs.

How do you leave your safety zone but do it safely.

You know there's a myth about entrepreneurs that they're all these kind of kamikazes that they jump out of an airplane with no parachute and the reality is that's just not true.

The vast majority of entrepreneurs as you know Jay mitigate their their risks.

You didn't just 1 day wake up and start making videos based on the teachings and learnings that you had assimilated as a younger man.

You didn't just go off and start doing that.

You were working for a bigger company and you were making content for the company and through that experience, that content was recognized by somebody else, then you got a job at the Huffington Post, you built an audience, and then you had the confidence to go out on your own, because you knew by that point you had amassed this experience and you had built a platform on which to stand.

This idea of leaving your safety zone, but doing it safely, comes from Jim Cook, who is the founder of Boston Beer Company, the company that makes Samuel Adams beer.

And Jim Cook was a, he had a very safe job, he had a career at Boston Consulting Group, but he wasn't happy.

He wanted to do something else with his life.

And he thought about creating a great American craft beer.

This was in the early 80s when American beer, I mean, Monty Python was making jokes about American beer at the time, right?

I mean, today it's crazy to think about because American craft beer is the envy of the world and beloved in Europe.

But at the time, in the early 80s, it wasn't.

So he started to experiment and research this idea on the side.

But he kept his job, and he kept his job for a long time.

And he kept working on this side project for a long time as well until he started to dip first 1 toe and then 2 toes and then 5 toes and then the whole foot and then a leg and then eventually he became comfortable and confident enough and it saved some money from his job that he gave himself the permission to leap and to take the leap and to try it, always knowing by the way that he could go back to his old job if it didn't work.

Now, that doesn't mean that it's an excuse not to try hard.

It just means that there are ways to take risks and to take the leap, but to do it in a way that if it all falls apart, it's not going to be catastrophic.

There's a fetish around failure, especially in Silicon Valley.

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Guy Raz ON: Safely Quitting Your Job & Building the Business of Your Dreams