How I Built This with Guy Raz - Gimlet Media: Alex Blumberg and Matt Lieber

Episode Date: October 21, 2019

Alex Blumberg made his early career by helping build two of the most successful shows in radio and podcasting: Planet Money and This American Life. In 2014, convinced that podcasts could make money, he walked away from the safe umbrella of public media to start a new media company with co-founder Matt Lieber. Every doubt, triumph and humiliation of building the business was documented on the podcast Startup, which included the back-and-forth over how the company got its name: Gimlet. Many more successful podcasts followed, and five years after launch, Gimlet sold to Spotify for roughly $200 million. PLUS in our postscript "How You Built That," after years of researching how women's shoes wreak havoc on the joints, Casey Kerrigan quit her job in medicine to start 3D printing more comfortable designs: Oesh Shoes. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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walking distance from so much of the city, made it feel less like a visit and more like we were actually living there. Plus, taking a trip is the perfect time to host your space on Airbnb. Your place with all of its personal touches and its amazing location could make someone else's vacation even better. Your home might be worth more than you think. Find out how much at Airbnb.ca.com. Really quick before we start the show, I want to remind you about an upcoming live recording of the podcast. It's happening in Denver on November 13th at the Paramount Theater. I'll be interviewing Kurt Richardson.

He's the creator of the Otterbox phone case. And if you haven't been one of our live shows before, they are super fun. There are a chance to see me and to meet other builders and fans of the show. It's all brought to you by American Express, and we'd love to see you there. So to get tickets, go to nprpresents.org, and I hope to see you in Denver. I had a dream. I was at some party, and Ted Cople was there. And it was like, Alex, how long are you going to stay at this job?

Don't you want to start something on your own? And I remember telling him like, no, Dad, I'm pretty happy. He's like, are you really? So then I woke up. And I told my wife about that dream. And I think that kicked it off. I just had to bite the bullet and quit. From NPR, it's how I built this.

A show about innovators, entrepreneurs, idealists, and the stories behind the movements they built. I'm Guy Raz, and on the show today, how two public radio producers turned podcast. into profit and a media company called Gimlet that sold for more than $200 million. So some of you may know that for most of my early career, I was a newsperson. I covered a bunch of wars. I was posted overseas. I was a host on NPR's evening news show. But then, in 2012, I left. I left to essentially relaunch a podcast. It was called the TED Radio Hour and I still host it.

And back then, that decision, believe it or not, was like going into the wilderness of journalism. Several of my colleagues were like, you're going to do a what? A podcast? And to be honest, I was a little embarrassed myself. I was leaving the prestigious world of news for the exile of podcasts. But of course, what eventually happened was precisely the opposite of exile. Podcasts exploded. Today, podcasts are a half a billion dollar industry.

And what was once considered an afterthought, even at a place like NPR, is now one of its most important sources of revenue. Now, back in 2014, one of my colleagues was watching this explosion really closely. His name is Alex Bloomberg. Alex is someone I've admired for a long, long time. He was a producer on This American Life, and then he went on to co-create one of my favorite shows, Planet Money. And Alex started to dream of an idea to build a production company like HBO except for audio for podcasts. But even then, the thought of making money off podcasts was still a fairly new proposition. Besides, like a lot of mature and stable organizations, NPR can be slow to innovate.

And Alex realized he couldn't launch this idea inside the company. So he left, which was a huge gamble. Lots of people in public radio thought he was not. nuts. He also knew nothing about how to run a business. Now, as many of you may know, Alex documented this journey on a podcast called Startup. In that show, he describes the emotional ups and downs of starting the business and how he eventually came to meet his co-founder, Matt Lieber. They decided to call their company Gimlet and went on to produce a bunch of podcasts, including Reply All and Homecoming. And then, in 2019, Matt and Alex sold the company

they founded to Spotify for around $200 million, which I think is fair to say is not a sum of money you often hear connected to public radio folks, unless they are major donors. Anyway, we'll hear from Matt Lieber a bit later in the show, but first to Alex, who grew up in Cincinnati. His dad was in advertising and his mom ran a public assistance program in the city. And even though it may not seem obvious given what they did. Alex says both of them were actually really entrepreneurial. Oh, yeah. They were entrepreneurial. And we never used that word. Yeah. I didn't learn that word at home. I probably learned that word in college. My mom was a social worker and she ran a public and employees assistance program, but I never heard her talk about it that way. And then my father,

he was always in advertising. My dad was always in advertising. And, And he, you know, he was a copywriter, and then he worked with a couple of different people of different agencies, and then he eventually started his own advertising agency. And then that agency, and then another one that became Wolf Bloomberg Crody. So he was the Bloomberg and the Wolf Bloomberg Crotie.

And, like, it grew pretty big. It grew, like, at a certain point, I think there were, like, 70, 80 people. Wow. And he never talked about it as, like. This is my business. Exciting. Like, we're building this business or anything like that.

If anything, he was embarrassed about it. Why? I don't think he valued it at all. I think all he wanted to do was be a poet really or like an academic or a great thinker of some kind but he had this successful business that seemed to kind of grow I guess just grow on its own

or grow organically I know I mean I remember asking him about this at one point because it was like later later later in the journey when Matt and I had started Gimlin we were like growing this company and it was like all I could think about and it was consuming every single sort of thought in my mind and one time later I asked him about that.

I was like, how did you feel about it when you were starting it? I never heard stories from you about it. And I think what he told me, he was like, I just never felt like I never felt like those were my people, the people I worked with. Did you sense or notice a change in your family's lifestyle, you know, having gone from your dad working for a company, your mom doing social work, to him running this pretty successful head agency? Oh, yeah. there was a moment where my dad's company was doing very well, and business was booming, and one of their clients was Procter & Gamble, and all of a sudden we had money, and it was fortunately right around the time that I was going to college. So they were able to pay for me and my sister to go to college. You went off to college. You went to Oberlin, and you studied political science, government.

Did you have a sense of what you wanted to do when you went to college? Did you think, I want to get it? into public service, like my mom, I want to do some kind of social work. Was that your plan, or did you think, want to get into journalism? Or did you not really know? I think I had a sense of, like, wanting to do something good in the world. Like, I remember I studied Russian because back when I was in college, Russia was still the evil empire, still communism. Right.

And I had this very sort of political feeling about, like, you know, there are people just like you and me, Mr. Reagan, and I'm going to learn their language and prove it to you. and I think one of the things I was a big consumer of narrative nonfiction from an early age. You know, we had magazines laying around the house, like we had the New Yorker and Harper's that was that kind of household. And like I picked them up early and really loved them. And then as I got older, I loved them more. But I never saw myself as doing that. That felt like the people who did that, the people who did journalism, those were the kids who were like sort of on the school paper.

and had, you know, majored in journalism and had, like, gotten internships when they were in college. And you weren't doing any of that? I wasn't doing any of that. I was, like, I tested well, and I took AP classes. Yeah. But I was not a motivated student. I was very comfortable with a high bee. So you graduate.

I guess you go back to Cincinnati? Well, no, I went to Russia, spent a year in Russia, then spent a summer in Cincinnati, and then moved to Chicago. And that's where I sort of picked up my post-collegiate life was in Chicago. And in Chicago, you were actually a teacher, right? I was. Yeah, I taught school at a private school for four years. I taught science. But it wasn't going to be the thing you were going to do. But it wasn't the thing I was going to do.

No, I didn't feel like it was the thing. Like at a certain point, sort of in my second or third year, I was like, I don't think this is really what I want to do. But like, honestly, I think really what happened was my girlfriend broke up with me. In Chicago. In Chicago. We'd been dating for many years, and we were in love. And it just really shook me. and when she was like, what are you going to do?

And she was like, I'm going to move to New York and I'm going to go to film school. And I was like, wait, that's not fair. We weren't supposed to be actually pursuing our dreams here. You're going to actually pursue your dream. And then I was like, oh, my God, and now you're going to go to film school. And then you're going to become a famous director. And then your name is going to be in the marquee,

and I'm going to be supervising recess. And it shook me. And it shook me. And it shook me into realizing. And I was like, well, wait, why is that wrong? I thought I liked a supervisor. revising recess and then I realized like no I want to I have something else that's my ambition but you didn't know what it was I didn't I knew what it was at that point because she was she was

transformative in two ways the other way that she was transformative is she was from New York and so she knew people in New York media and so through a friend of one of her friends he was like best friends with one of the editors at Harper's magazine and I was like wait There are people at Harper's Magazine who are friends with the people I'm friends with. Like that seems crazy. You know, like they felt so far away out of, you know, like completely beyond my reach. And then here this guy was. And so I had spent a summer in Brooklyn interning at Harper's Magazine for free.

This is like 1996. Something like it. 1994. 94, okay. 94, yeah. And so I knew that I'd wanted to do that. I'd been really captured by that experience. So I was like, okay, well, that's my dream.

I should start pursuing it. So what did you do at that point? I dabbled. I did a bunch of things. I dabbled in grad school for a little bit. I went to a year at grad school in Chicago. But basically, after she broke out with me, I was 30 years old. I didn't know what I was going to do with my life. And I was like looking around for stuff to do. And I found out about this American life is what happened.

As a listener? I knew about it as a listener. And I knew that it was coming out of Chicago. and it was like the incredibly hip new thing. And a guy who had worked at Harper's Magazine, who had been this incredibly intimidating editor there, who I was really enthralled with, but scared of. This guy, Paul Tuff.

He was working with This American Life in the early days. And so through him, I got introduced to Ira, I believe. And I was able to get a job as the administrative assistant at This American Life. So you are in your early 30s. Just been dumped. Just been dumped. You're an administrative assistant at this American life. Living the dream.

Yeah, was anyone worried about you? Did anyone feel like, God, you know, like, were your parents sort of like wondering, like, does Alex have any direction or what, I don't know what's going on in his life? The time around medical school is running out here, son. Yeah. Were you worried or not really? Oh, I was really worried. I was really worried.

I was very aware of, like, how I presented. Like, I was like a loser, you know? I was like 30 years old. I'd just been dumped, and I didn't have a career, and I was an administrative assistant. But it felt like I'd spent the entire previous decade just not doing anything, just like waiting because I was afraid. And I thought, like, that would keep me safe. And then the safe thing had just resulted in intense heartbreak. And there's no excuse that out not to do the scary thing.

So it felt for the first time in my life, I felt like I was like where I should be. and being the administrative assistant at This American Life, it was like Ira and three producers, and they were trying to get out an hour of highly produced radio every single week. And they were just like completely up to their necks in work. And so there was lots and lots of stuff for me to do. And was Ira teaching you how to make radio? Yeah.

I mean, he was. I don't think it wasn't like he was sitting down and like, he was like, come here, administrative assistant. I don't teach you how to make radio. but it was just such, it was like the second year of this American life's existence. It had already become something

of a thing in the world. It was like, you know, very well known. It was on a lot of radio stations and it was on the rise and Ira was just running. Yeah. And never stopped. He would get there early in the morning

and he would leave late at night and everybody would, and including me. And so like, he had no choice but to teach me. How did you get your first story onto the show? Ira came to me and was like,

the 10-year anniversary of Harold Washington's death is coming up. And he was like, I'm wondering if we should do something for it. Here's this book. Read it and see if you think there's a story there. And so he gave me this book called Fire on the Prairie by Gary Rivlin, which was all about Mayor Washington. Mayor Washington was the first black mayor of Chicago, and he'd been this sort of like incredibly charismatic leader who just sort of like just tipped off this entire,

you know, the sort of hailstorm of racist backlash inside in Chicago. So we started producing it together And I just like would identify all these people from the book And then we would go and interview them And I'd sort of try to help them come up with this with the questions And I remember that like the show came out on a Friday And on Wednesday We had nothing written

Nothing produced, nothing cut Wow And then he just dove in and just wrote An entire hour long documentary in three days Wow It's crazy He stayed up all night I'd never see anything like it

Yeah I remember that I think it's called Harold. It's called Harold. Yeah, I remember that episode. It's a classic This American Life. That was the first thing you produced. Yes. That's one way of looking at it.

But it was so exciting. Yeah. Being there. It was so exciting. And it was all that I'd wanted. And so the thing that motivated me was like, I need to take this is what I want to do. I want to do this. And by hook or crook, I'm going to learn how to do it.

But I mean, I'm going to learn how to do it. But, I mean, I'm going to do it. Obviously, you started to do more and more and more stuff for the show over the next couple of years. So, yeah, over time, I, like, I became sort of like one of the more experienced seasoned producers at This American Life. And that meant doing my own shows, doing my own stories, as well as producing other people's stories. And then there was a couple of years of that, just making stories that just felt really exciting. Okay, Alex, I want to just pause for a sec, because Matt Lieber is next to you. and he's been waiting here patiently.

Yes. Sorry, I'm digesting. I'm digesting everything Alex just said. I've never heard you to tell all those stories together. Oh, yeah. Can I just, I just want to do like a split screen here for a sec. Because while Alex, while you were working at This American Life, Matt, you were in college, I guess, around that time. And I read that you, you were like a big fan of radio.

Yeah. So do you actually remember listening to This American Life at that time? Yeah. Like it was like literally I was in the car turning the dial and then I heard an episode of this American life and I was and I stopped because I was like this doesn't sound like anything else. Yeah. Which is funny because now like a significant portion of the most popular podcast on earth are this sound. But at the time it was really weird. It was unusual. Yeah. And I guess we should just back up for a sec to say that you you grew up in Massachusetts just outside of Boston. When you went to college to Bowden College in Maine, did you also get involved in college radio? Well, I had done some radio. So when I was in college, I interned at the local public radio station.

So I was doing my college radio at Bowden, which was WBOR. And then I spent the summer interning at WBUR, which was the NPR station. And when I graduated college, I was kind of trying to figure. I had applied to be an intern at This American Life, and I spent like a week on my application. You had to, like, write an essay. You had to critique a story. You had to pitch a couple stories.

Yeah. I had all this, like, I thought, like, I have all this radio experience. Sure. Yeah. I sent in the package. And I didn't even get rejected. I just got nothing. Nothing.

Like, I just didn't get a response. Because Alex, because Alex threw it in the garbage. He was in Chicago. Alex must have been on the other end. He was on the other end. What year was this? 2001. Do you remember his application, Alex?

No. It was that memorable. Thank God. I was not in charge of the intern applications at that point. All right. So you don't get the internship. So instead, I guess, just out of college, you moved to New York to try to get a job in radio. Yes, that's right.

I moved to New York on September 1st, 2001. Wow. With the idea that I would get into radio. but not knowing anyone. But I figured if I wanted to be in radio and media, like New York would be a place to go. And I had a friend who had a room open and his apartment.

And then on the morning of September 11th, 2001, I was on my way into a job interview in downtown Manhattan at a staffing firm. It was the kind of place where they would put you and you would be a receptionist at like an insurance company. Yeah, a temp agency. Temp agency, exactly. And on my way to the subway, so this was 9-11, and on my way to the subway, like the second plane hit the second tower.

And the subway shut down. And so I didn't go in to Manhattan that day. And on the way back from, as I was going back to my apartment, I saw this guy in a park in downtown Brooklyn hitting golf balls. He was just hitting a pitching wedge. And there was a whole crowd of people all around the park looking. up at the smoke coming from both the towers. And this guy just kept hitting golf balls. And so I was like, it was surreal. It was just surreal. Yeah. And so I ran home. I got my minidisc recorder and I interviewed the guy. And he was from, he was a Trinidadian guy. And I was just like, how can you be, like,

aren't you upset? Like, why aren't you home with your family? Like, why are you hitting golf balls? And he was like, he was just basically like, no, man. Like, this is America. And in a America, you know, everything's going to be all right. Wow. And you actually turned that into a radio story, I think. Yeah. It aired on Weekend Edition, which was an NPR show, and, you know, millions of people listened to it.

And that was like my first, that was the first piece I ever got on a radio show. You would actually go on to spend the next several years working at a couple of different public radio stations in New York and in Boston. And I guess like around 2010, you make a big change. Like you decide to go to business school. Yep. So what happened? What changed?

Well, I had done all these jobs in radio. And I think I spent like a year, a year and a half actually working at MTV Radio. My job was to interview celebrities on red carpets and then cut up sound bites and send them to local music or DJs. But most of that decade I spent producing journalism. news, culture, and also music at a number of public radio shows. And I happened to be on three shows in succession that were canceled. And that made me doubt whether there was going to be enough like stability and opportunity for me. And I remember at the time, my parents were always a bit bewildered by why I was working in radio. My dad particularly was confused, not by my interest in

media, but public radio? Right. And I remember what he would ask me. He's like, he's like, hey, maybe, have you ever thought about television? It's like, because I think you could make a better living in television, which he was correct about. And it was at a time, it was just a really hard time in media period in New York. So this was 2008. There was lots of layoffs happening.

The beginning of the internet as a disintermediation of publishers was happening. So if you were in legacy media, you were looking around realizing that your business model was collapsing. Yeah. And people were beginning to get laid off from like newspapers. And there was this rise of digital. And I remember reading an article in New York magazine about how like media was no longer going to run New York. There were all these new startups and they were like technology and product startups. And that was where the future was.

and there were these people who were entrepreneurs who were like crazy optimistic about what the world they could build is. And also I was in journalism, so people are just generally, like journalists are skeptical by nature and I thought like, I kind of want to be on the other side of this.

And so that was when I decided to leave. So you went to business school with the idea of like, I don't know, going into consulting or starting a business or something like that? No, I went to business school as like a last... It's like a lifeline. Yeah, it was a lifeline. I began to understand by that point

that some of the biggest changes in our world are driven by business. And if you understood how markets function and how business operates, that's like a tool set that you could do a lot with. All right, I'm going to go back to you, Alex, and we'll come back to you, Matt, in a bit. So, Alex, you're working on this American life and really become a part of the ensemble.

I think anyone who remembers that show in the 2000s remembers your name, hearing your name all the time. And then in 2008 there was a pretty significant kind of moment where you produced an episode of the show called The Giant Pool of Money. And you did that with Adam Davidson, who was also a public radio reporter at the time. How did that happen? How did that come about? Yeah. You know what, it was somebody at This American Life had bought a house. And I had asked her like, well, wait, how did you have enough money for the down payment? And she was like, oh, we didn't have a down payment.

We just, they just gave us the loan without a down payment. I was like, really? I was like, I didn't know that happened. And she was like, oh, yeah. And so then that started me like, it was like, that's crazy. And then there's all this credit card debt out there. And everybody I knew had huge credit card bills. And so I was just like, sort of like, I was just like casually looking at this, the story of debt in America.

What's going on? And then the more I got into it, the more I got into it, the more I, I sort of like started to understand the macroeconomics of it and how it, what that had to do with the Chinese central bank. And I was friends with Adam Davidson this whole time. And Adam Davidson was a, correspondent at NPR. And he was the business and economics correspondent at NPR. And so we had been kicking around this idea of doing something on like housing debt. So we reported this whole story of like the global financial system and how it had sort of led to these conditions where people were barring massive amounts of money without anybody checking to see whether they could pay it back or not. And it

explained this thing that was happening all around and explained it in a way that had like characters and people that you could hear and hear those stories and it was funny and yeah i think adam and i both knew it like we both knew while we were making that like we're on to something here like it felt like this very powerful thing yeah that episode the giant pool of money um would go on to win like every award and it was a huge huge piece of journalism that year um it got a lot of attention and i guess the two of you decided, hey, why don't we, why don't we start something around money? Why don't we do, why don't we create something bigger, which led to the creation of planet money. Yeah. And Adam sort of said to you, I need you to join me to make this happen. And the two of you

had to kind of build a company within a, like a mini company within a company, right? I mean, or like an ensemble cast, like this American life. Yeah, yeah. We had, we came in and we were like, okay, we're going to do this, we're going to do this, like, it was daily at the beginning. It was this daily podcast. And me and Adam were like the ones in charge of it, and we'd never been in charge of anything before. We had to go to management training, learned a lot about ourselves. That is, and that was sort of the experience where I sort of learned like, okay, I can be a boss. While you, the two of you were kind of ramping up Planet Money and as it kind of hit cruising altitude and became a really successful podcast and radio feature on some of the NPR shows,

Did you, did you, I mean, you're now in your early 40s. Were you married at that point? Did you have kids? Yes. Early on, right in the very sort of beginning of Planet Money, our first child was born, my son, and then our daughter was born, you know, less than two years later. So, yeah, it was sort of a busy time. We were starting Planet Money, and I was, like, starting a family at the same time,

trying to balance it all. Eventually, Adam, he decides to take a leave, to write a book, and sort of starts to move on from the show. You are still there. At what point did you start to think, maybe, I don't know, maybe I should move on? Well, I think it was a gradual thing. I think a couple things happened over the course of Planet Money.

One, we did this project called the T-shirt Project, which was Adam's idea, which was like, I think he came in one day and was like, I think we should follow a T-shirt around the world as it gets made. Like cotton-field to the store? Yeah, exactly. We start with the farmers who make the cotton, And then it gets spun into the yarn and gets woven into fabric and then cut and sewn into t-shirts and then it gets shipped back.

And we'll tell the whole story. And it happens all over the world in all these different countries. And we'll meet the people and we'll actually make a shirt. And then we just started thinking about it. It was just like the super exciting idea. So we, you know, I think it took like another year or year and a half before we actually did it. And it was this huge hit. It was like it became this thing that our listeners went along with.

We started talking about it. We would prepare all these stories about it. And then we sent all these reporters all around. And you sold a lot of T-shirts, right? And we sold a ton of T-shirts. We sold, like, 20,000 T-shirts. Wow. We made, like, almost $600,000.

Which was not, like, profit for you guys, right? That was just NPR's money. Yeah, that was just NPR's money. But it was also, like, and that's what we used to fund the trips and everything like that. Like, we knew that that was going to... We were hoping to earn back what we spent on, like, doing this crazy project, but we made that back and more. Yeah. And we were doing these, like, live events where, like, there'd be huge...

theaters would show up and see us talk, and people were like asked us to sign autographs, which never had never happened to me before in all my years of radio journalism. And so it just felt like there was something going on here. And it felt like there's money to be made. And it felt like there's a big opportunity, you know, to like, if we can tell, if we can start a podcast, the super popular podcast about business and economics, then you can start a podcast about anything. And it just felt like we should do that. We should do more.

We should do more Planet Monies. You wanted to start more shows. I wanted to start more shows. I wanted to figure out a way to do it with NPR. Because podcasting started to really gain traction, right? Yeah. I started TED Radio Hour in 2013, and we were one of the early shows that really got a big audience. I mean, people were starting to talk about podcasting around that time as a viable business.

Podcasting, just like the numbers were just growing. And then there was people out there who were making it, who were making a business of it independently. Like Roman Mars, who had launched the podcast 99% Invisible, was very inspiring to me. Like, he was out there on his own, and he had done it. He'd been doing it for like a couple years prior to me leaving to lunch Gimlet. And he had like a small staff and he had like advertisers. And I remember asking him early on like questions about like how, you know, where do you get your advertisers? How does it work?

And it was just working really well for him, you know. Was there excitement when you talked about this at NPR? Was there excitement? Were people like, yeah, this is great? I don't, in some places there was. But it was like, I also knew that it was important to me that it wasn't going to be a nonprofit. And the reason was, if you have a large global news outfit

with people all around the world, there might not be a viable business model for you. And you might need, to make that work, you might need foundation money and stuff like that. You might need to just like go. that route. You might not be able to actually just turn a profit. But with Planet Money, I was like, no, you can turn a profit on Planet Money. That's like advertisers want to be in that show. The audience is big enough. It can be profitable. And if it can, it should be. It doesn't make sense to force it into a structure that it doesn't need. And also, I felt like I was creating a lot of value. Yeah. And I wanted to have ownership of that value. If I was going to take this risk, I wanted to be able to be rewarded for it. So as you were kind of thinking about this idea, did you have a clear idea of what it was going to be? Or did you think like, okay, we're going to have, we're going to spin this out, we're going to create all kinds of new shows.

They're going to be this, this, this, and this, and we'll need a team this size, or was it more abstract? Definitely more abstract. It was like sort of like, we'll need to make the planet money of cars and the planet money of the Internet and the planet money of, you know, whatever else, you know. And my plan in the very beginning, before I met mad and before I actually had actually talked to any investors or anything, was like, I just need somebody to give me a bunch of money and then I can hire some people and we can start making stuff. So at that point, I mean, this is 2013? This is 2013, 2014, yeah. I mean, was the challenge you were running into at NPR that they were a nonprofit organization and they just could not figure out how to make this work? Or was it more like, yeah, we're just...

No one really wanted to make a decision. Nobody wanted to kind of pull the trigger or no one really thought that there were legs to this. Or was it like a combination of those things? A lot all the above. I think I was a risky venture. You know, like there's not that many places that are set up to like take that kind of risk. Even though I didn't feel like a risk, even though I felt like, well, I know how to do this. And like, obviously I've done it before.

But like, no, that's not true. I've done it inside institutions whose contributions I was way undervaluing, you know? If you're NPR, that's a lot of risk to take to just be like, yeah, I'm going to give you this money to try to start something that, like, I have no idea if you'll succeed or fail. And there's not that many institutions set up to do that. To do that, yeah. I was frustrated, though. I was frustrated. I was frustrated at the inability to, like, I felt like we were sitting on gold.

I felt like we, they recognized the editorial gold, but I felt like we were sitting on financial gold with Planet Money. And people love it. And it's brand new and it's different. and they're consuming it in a different way, and it just feels like, you know, that you're getting these, like, teeny tiny ad rates and, like, nobody knows what it is yet. And it just felt like we were just this giant

and that nobody knew about us. Yeah. Do you remember the point in your mind where you thought, I'm going to leave, you've worked for organizations your entire life? You've never run a business. You've never gone out on your own. You've got, like, a family.

You're 47. How did you get to a point where you thought, I am going to do this and I will leave my safe, stable, comfortable job if I have to? Because that's a pretty big leap. I don't know this is exactly the moment, but this was a moment. I mean, it's never just one moment. But here is a moment that I remember. I had a dream. I was at some party and Ted Cople was there. And Ted Cople somehow knew who I was. And he came up. to me at the party and he was like, Alex, how long are you going to stay at this job? How long are you going to do that? Don't you want to start something on your own? And I remember telling him like, no, Ted, I'm pretty happy. He's like, are you really? So then I woke up. And I told my wife about that dream. And I think that kicked it off. Yeah. I just had to bite the bullet and quit.

When we come back in just a moment, how Alex learns that it's a lot easier to make a podcast than to make a podcast company and how he documents almost every humiliating moment of that process on the show startup. Stay with us, I'm Guy Raz, and you're listening to How I Built This from NPR. Hey, welcome back to How I Built This. I'm Guy Raz. So it's 2014, and Alex Bloomberg is going to walk away not from one, but from two, plumb jobs in public radio. And he's going to do this to start a podcast company,

something that at this point was not an entirely proven concept. So he decides to lay out his case on a podcast, which he calls startup. Here's a clip of it. I love podcasts. It seemed like someone should come up with money to invest in making new shows like these and come up with a theory about how those shows could be profitable. I kept waiting for someone to do that.

And then came this thought, a thought that's gotten a lot of people into a lot of trouble. The thought, well, I could do that. And did you think you were going to do this by yourself? Was it the plan at the beginning? Yes. I thought that was what I was going to do. Basically, I was on my own. Millions of people listened to this American life and Planet Money at NPR, and I didn't have any personal brand.

And so my big fear was like, I figured. I figured I'd be able to, like, get a podcast together. I just didn't know how anybody was going to know about us. Yeah. So I had to do something that was going to attract attention to what we were doing. And I figured, like, okay, a guy recording himself trying to start a company, that'll be good. It was like a marketing ploy. Doing an audio diary of, like, making this company.

Yeah. Are you meeting someone with money? This is my wife, Nazanine, early one morning a couple months ago, stopping me as I was on my way out the door to do something. I had never done before. Meet a guy who works at a venture capital firm and try to get them to give me money. Did you in your mind have a sense of how much time you had before you could no longer just survive off Nazanin's income?

No, I didn't. By that point, she was working at MSNBC, so she was making a lot more than you make in public radio. But it wasn't long. Like, we didn't have a ton of savings, and I didn't have a job. Yeah. I had a couple, I had maybe like, I don't know, three, four months, five months.

That was it. Max. And, I mean, you were like in your apartment, you had, I think, two kids at this point, right? Yeah. And you just started out talking into your microphone. Yeah, I started anything I was doing. I would mic myself doing it. Any meetings I had set up, I would tell the people ahead of time, like, and, you know, I'm starting a podcasting company.

And, like, funny thing, I'm also making a podcast about it. Ha, ha, ha. I'm going to come out with microphone. And for the most part, they were into it. Like, it was like, you know, it got me in the door in a certain way. It was like, it was unusual. Yeah. You know, like, if you're a VC, you've seen 75 gizzillion people pitch you a different kind of, like, food delivery app or something, you know.

But you probably haven't seen people come with a full head gear and boom mic recording it. So if nothing else, it was a novelty. All right. So you leave Planet Money in March of 2014. and would you go like just have meetings with people who had money? Would you just try to set up meeting after meeting? Yeah, I would set up meeting after meeting. I would reach out to everybody that I knew who'd been involved.

And you just meet somebody and then they introduce you to somebody else and they introduce you to somebody else and it's all like a, you know, but ultimately became very clear like nobody was going to invest. I could only tell half the story. I could only tell the story of like, here's the kind of things that I've made and here's, and I'm going to just keep doing that. And that wasn't a business. That wasn't a business.

And your pitch was, I want to make, like, the HBO of audio. Yeah. I want to make really high-quality shows. It's going to be ad-supported. Maybe we'll sell stuff. Podcasts are here. Everyone. Yeah.

No, I feel like I would go out and I would be all pumped up and I'd be practicing. I'd go over my pitch and I'd go out and do it and then I'd fly out somewhere. And then I was one of, like, I don't know, three, four meetings that day. And I was just one idea out of a million ideas. and other people were pitching ideas that had proprietary software or, you know, like scientific breakthroughs, and they'd been like part of a lab at Stanford, and I was pitching a podcasting company. And I hadn't worked in a for-profit company since I was a bagger at a grocery store at school in high school. And I remember calling my wife.

I think we actually recorded one of these conversations when I called my wife after one of these things. I think it actually ended up being in a startup episode. Oh. How are you feeling? I'm feeling the same way I felt the last time I was out here. I'm sitting there talking

to this guy and I'm describing something that feels like the biggest thing I've ever done. Like a scale beyond my wildest imaginings. Something that I can't even tell if I

could pull off. And it's totally not big enough. Like it seems small. to him. But even when I was at the depths of my depression and feeling small and stupid and like, what the hell have I done, the fact that I was able to talk about it on tape, I knew it was good tape. So the more I failed as a wannabe entrepreneur, the more I was succeeding as a radio documentary producer. And so there was something weirdly comforting about that. Like, at least all this work won't be for nothing. At least I'll have some document.

Yeah, I mean, startup really was fascinating to listen to. And these like now iconic moments, like I think a lot of startup fans will remember that moment when you're trying to pitch Gimlet to the investor, Chris Saka. So I'm making a network of digital podcasts that we will monitor that that will, that will, that is going to meet. Sorry. So what's it going to take to do it? So it'll take a million and a half dollars, I think. Take out the I think. Yeah.

I was so naive. And it was like that meeting that really showed me how naive I was. All the questions he asked, I had no idea how to answer. What's the exit? I was like, what's the exit? What does that even mean? He was like, well, you know, I give you money. You build the company.

Then how am I going to get my money back? What's your exit? you're going to sell to? And no idea. Didn't have even occurred to me. Yeah. And when people said, yeah, I'll offer you a little bit of money here or there, how did you even know, like, what percentage to give them? How did you even know how to accept the terms on the term sheet? Did you, were you consulting with a lawyer? Did you just, because those things are complicated. Nobody was offering me money until, I literally nobody, I don't think anybody offered money until Matt and I teamed up. I think when I was,

was doing it by myself. I didn't even get to that point. So you come to this conclusion that you need a partner, probably somebody with some experience in business, or maybe at least an MBA. When did you meet Matt? I met Matt over the summer of 2014, I believe. And we were introduced by a mutual friend in public radio. And the story that I heard was that sort of like there's another guy running. it all around town with sort of the same story, talking about how there's a business to be built in audio. And he was sort of often his world doing the same thing that I was doing.

And so we finally met. Matt, when you met, Alex, what were you doing in the summer of 2014? I had done my MBA and then become a management consultant at Boston Consulting Group, which meant that I would go and work inside of large companies. and help them develop growth strategies or solve problems or things like that. But then I began to think about digital audio, and I was listening to a lot of podcasts at the time. And I thought every time a new medium comes about, new media companies get built.

This is true across the last 100 years of history. And I thought someone will build a defining media company around on-demand digital audio. and like, why not me? And I told a lot of people about this. Not that I was starting a company, because Alex was much further advanced than I was, but just like, that would be exciting. Like, I think someone's going to do that,

and I think it would be really fun. And I told my friend Graham, who had been a mentor to me back in my radio career, and he said, oh, you should meet this other guy, Alex. What did you think about him when you first met? Did you think, this is it? This is, like, a slam dunk? I'm in.

Or was it not quite that clear? I mean, this is the thing about, like, I felt like I already knew him because I had listened to his stories. This is the thing about audio. Like when you live, and I'm sure you've experienced this guy, which is when you meet people, they walk up to you, like, they're your friend, right? And everything he was saying about, like, I'm excited about audio and I think it's underestimated and I want to do a business around that. I was basically, I just sat there and shook my head and said, yes, and I think this is how the business could work. and I think it could be really big. And that sounds exciting.

And I basically said, let me know how I can help. Yeah. It's a funny moment because really what I was looking for was a co-founder. But I didn't know my co-founder yet. And so there's like some sort of weird dating thing that has to happen. And as we started to talk more about like what would be helpful, I think you suggested like, why don't we do a business plan? Right.

I think I just started working on it, basically like nights and weekends and sending you things. and what kinds of shows we would create, which was along the lines of what you were doing, but also how they would get distributed, who the partners would be. And I was doing that not because I was, like, trying out to be your co-founder, actually. That's the crazy thing.

And I was doing a lot of work. You're doing so much work. But I was, the thing, for me, it was like, it was fun. And I would wake up in the morning, just excited to do it. Yeah, and I would get up in the morning, and there were early in the morning, and there would be, like,

multi-page business plan that Matt had somehow produced. And I was like, oh my God, this is, you know, amazing. And making a case that investors could actually get behind. But did you, Alex, did you pretty much from the beginning when Matt started to kind of help you out and just give you free advice, did you think, okay, I think this is the guy? Or were you not quite there yet? I wasn't quite there yet because I think we didn't know each other at all. Yeah. We had met like three times. Did we only meet three times when we...

No, no. I mean, by the time we signed, we'd met more than three times. By the time we actually signed an agreement. But like, I think around the business plan era, right, right, yeah. We came over, we had an initial meeting sort of at my house where Matt brought over some beers and we drank beers and talked about like what was happening.

Just a couple startup brosks drinking bruskeys, hatching plans. I did a bunch of, I did some reference checking. So I started calling around to people who had worked with Alex. You did? Yeah. I didn't know this. Oh, yeah.

And it still shocks me that you didn't do that for me. But, of course, like at the time, you didn't have a clue. Now you would never hire someone without, like, blind reference checks, right? So I called a couple people who'd work with him, and they're pretty consistent, which is he's a brilliant, brilliant editor, like, incredibly supportive. And then I had lunch with Adam, Davidson, your partner. Oh, wow. Adam is a very direct person, and he was also like, yeah, Alex is also, like, tenacious and, you know, doesn't back down and is really stubborn. And actually, all that turned out to be true.

Like, the four words to describe Alex aren't those. Brilliant storyteller, stubborn control freak. And I was like, those are some of the qualities you want to have in starting in the early stage. And what about you, Alex? I mean, Matt, you didn't know him at all. You just knew that he had some experience that was in public radio and he had a business degree. I had concerns about how we didn't know each other. And I was worried about that.

And we're pretty different people. I'm trying to think of what our first major conflict, though, was. Oh, I remember very clearly because I think this is before we agreed to partner. This is going to sound very diabolical. but I was like, we have to have a fight so that we see how each other are going to conduct ourselves in a situation with conflict. And I kind of forced it.

It was like 9 p.m. We'd both put our kids to bed and then I came over your apartment. And I think it was about, it was our eternal fight, which was you were saying, we're just going to make a bunch of podcasts. Like, that's what we're going to do. And I was saying, first of all, we're going to make more than a couple of podcasts. We're going to build a company and an organization and a culture.

And it's going to end up being really big. And it's going to be way more work than we're doing now. And it's going to be incredibly hard. And I think you're underestimating that. Because for you, you think you're just going to be able to do the same thing you did at Planet Money, but do it a couple more times. And actually, the thing we're doing is completely different. So when you guys finally did decide a partner, how did it come about?

Well, Alex did it as part of startup. So the final thing to discuss, which we had put on the agenda for last time, where we see this relationship going. Yeah, checking in on it. Looking back, I think you only felt comfortable having that conversation because you had the microphone. And then that began a negotiation, basically, about what the partnership was going to be. And I think Alex, originally, you offered like 10 to 15% ownership, something like that, right? No. No. Way lower.

No. I think it was in, I think I said in the range of 1 to 10. I'm key to the success of the company. And I want to feel that that is reflected in the cap table, I guess. There's a subtext to the I am key to the success of this company, which is you are not. You meaning me. And Matt was. You were somewhat offended by this, justifiably, I would say.

I can't imagine doing this for the numbers that you're talking about. I just can't imagine doing it. Because if it's 90-10, I'm like, now it's a job. And in a job, I'm not going to like, and then you're the boss. I'm just not interested in that. And I don't think that will make the company succeed. So you guys play out this negotiation in the podcast. Eventually, Matt, you come back.

You say, let's split it. Then you say, okay, about 53-47. Alex goes back. You talk to your wife. Your wife is saying, no, it's too high. Finally, you agree on a 60-40 split. This is all out there for everyone to hear. This is public.

All public. And that was great. Everybody was happy with that. I was. Were you? Yeah. I was excited to just get started building the company. and I felt that it was being able to get through that negotiation and get to an agreement.

It solidified our relationship. And Alex, that entire time you were going back and forth with Matt, like, how confident were you about this idea that this company was even going to work? You know what? I think on some level I knew it would work. I'm not a big risk taker, not a serial entrepreneur. it just felt so clear to me. But of course I didn't know

it was going to work, right? So of course you actually have anxieties. And eventually I admitted to myself the possibility that like, oh, this could not work out. But it was by that point, we were like four years into it and it was definitely going to work out. Like it was already growing. And it was like, it's funny.

And, you know, I looked when we eventually sold the company to Spotify, people were posting in Slack Channel all these very, very first pictures of the very, very first office in the very, very first months of that first office. And at the time, I'd been so proud of that office, and I couldn't believe that, like, look, we have an office and we got people to give us money, and it's all working.

And then I looked back, and I was, and for the first time I saw it through the eyes of a non-true believer. I saw it from the outside. And I was like, oh, my God, you quit your good job to do this, to, like, show up in this dusty office with no infrastructure, and, like, you guys made your own studio, and, like, what were you possibly thinking? And all these people came along with you.

Like it felt like looking from in hindsight, I somehow accessed all the doubts. And of course, on the startup podcast, you described all about that first office in Brooklyn and the people you hired and working with Matt. And you also talk about how early on you changed the name of the company to Gimlet. Because I guess one of your potential investors thought your first name was just dumb. like American public What was it again? The American Podcasting Corporation. The American Podcasting Corporation.

It's a genius name because it was like a callback to the original big media companies that were started in the original era of like of radio. American Broadcasting Company, Columbia Broadcasting. Yes, exactly. Yeah. So did you like the name Gimlet at the beginning?

No, I didn't. And it wasn't just investors who hated the name American Broadcasting Corporation. It was also Matt. You hated the name, too. I hated the name, and I insisted on a new name. And then there's a consulting company whose job it is to create names for new companies and new products. And they ran us through a process that lended us on Gimlet.

And I think what you didn't like, and I think part of the reason you didn't like it was maybe you didn't like the name. But I think more of the reason was you didn't like the idea that there were some experts that we were going to go consult in such a corporate fashion. who would give us our name. Yeah, it felt like... Fony. It felt inauthentic, yeah. I don't know. This is interesting.

Like, I think Matt and I, one of the other big fight we always had was just around your gut, like, and how you make decisions. And I'd spent like 12 to 15 years making decisions with my gut. Like, that was the way you do it when you're making a story for this American life.

And I was taking that with me into starting a company. And so, like, the fact that a branding company had come up with our name, it just felt like, it just felt wrong. But, of course, it wasn't wrong. It ended up being totally fine. So as you guys roll through 2014, your first big, I guess, acquisition or partnership was Reply All, which was a show that was a slightly different version of that show, but it existed. How did you guys convince those guys, PJ? and Alex to bring their show to Gimlet.

They were hungry to do something. It was a side project. They had day jobs. We had to convince them that it was okay to leave their good jobs and join a shaky startup. But it was exciting. I think a lot of people were feeling the way that I had felt, which was that, like, there was more happening here

than public radio has the infrastructure to accommodate right now. And startup put us on the map, reply, I'll put us on the map. people knew about us, people were coming to us and just being like, oh my God, I hurt, I just put some startup, can you still invest? Yeah, and I guess people were actually investing. You initially managed to raise about a million and a half dollars. But I mean, even with a million and a half dollars, that wasn't really going to be enough, right? Like, could you scale up with that? Could you actually like start hiring a lot more people?

Well, when we raised the first million and a half dollars of financing, our plan was that that would take us through to profitability and then we would fund our growth through profits. Right. We always built the company so that we could either be profitable or get to profitability based on the amount of cash we had in the bank. And we were always over-optimistic in our projections. You thought that that seed round was going to be the only round of money that you had to raise. Yep. Every round we thought was going to be the last round. Was it just the reality of the business was that you actually could not raise the amount of money you needed to raise? It just the money wasn't coming in instantly from advertisers or whatever?

No, it was a combination of we decided to grow faster than we originally had. So we decided to launch more shows which required hiring more people than we originally had planned to in the original plan. And the reason we decided to go faster was we saw that like podcasting as a trend and as like a cultural moment was really crystallizing. And we didn't, we wanted to make sure we stayed at the forefront of it. So we wanted to launch more. And so that's why we ended up raising more to grow faster. And also just like we had like in the beginning like we had so many hits, you know, like startup was a hit and Replyau was a hit and mystery show and Crime Town and what's Matt's not. saying is like he built an entire infrastructure at Gimlet. He built a sales team and he built

the sales marketing team and we built and built a finance operation and a people ops operation. And all those things were working in concert and he hired really good people to like lead those and build those. And we were monetizing. I mean the business, so you say the business is working well, but I have to imagine it's a media company. And I can't imagine that you were making more money than you were spending. You had to spend more money to grow. this business and did that worry you or did you guys both say we're just we're not going to make we're just not going to make a whole lot of money in the first couple years we actually did make

more money than we brought in like in our second year of operations we generated profits on an accrual basis because the way the podcast work is you launch a podcast and when you launch it it has an audience of zero but you have to pay the people to make the podcast and that they're going to work for you for a few months before you're able to launch. And then once the podcast launches, you have an audience of, you know, tens of thousands or maybe hundreds of thousands of people, if you're lucky. And then over the course of a year, the audience grows and there's a size of an audience where you multiply by the size of audience times the number of episodes you produce, times, you know, how well you're able to monetize through advertising. And then it becomes a profitable

entity. So each podcast is like a little business inside the big company and you have to invest in them before they become profitable. And we always understood that. Were you just being inundated with pitches? Hey, I've got this idea. I want to do this show. And I'm assuming you were. And how did you filter out? Like, how did you deal with that incoming? That was hard. That was one of the things that was really hard. It was like sort of like everybody at the pitch and like, okay, we've set it up to make more podcasts. And then it's like, okay, which ones are we going to launch? How are we going to launch them?

Who's going to do them? And then everybody in the world is like, I want to do this podcast. I want to do that podcast. And what do we do? How do you do this over and over and over again with a bunch of different people in a bunch of different topic areas? And how do you not make it the same thing over and over again? Like how do you not make it actually the planet money of blah, blah, blah?

Like how do we actually make them feel new and different? And that was hard. That was the thing to figure out. I remember we had a conversation, Alex, I think it was probably like 2016. And I think at that point you said, you know, I'm almost at the point where I'm making as much money and income as I made at NPR. I think it was around 2016. And I thought, man, that is just such a risk. Like, this guy's in his late 40s.

He's got two kids. And like, he's just getting to that point after two years of a slog. And wow, you know. And I don't know if you guys ever experienced this, but being on the outside and, you know, me sort of being connected to the public radio world and the radio world, I had a lot of conversations with people who are so skeptical who said, you know, that thing is just not going to work. It can't work because they're not going to be able to be as profitable as they say and their investors are, you know, they're not going to make a return and blah, blah, blah. Did you guys ever hear any of that nays saying? Or were you sort of shielded from that? we heard it secondhand.

Yeah, nobody never would say it to our face. No one said it to your face. Nobody face said us. But I think that we had both come out of this amazing institution of public media. And what we learned there informs our success. And a lot of the people who were early employees and built the company came out of that same system. But I think in some places we were viewed as a threat. And I think some people's.

natural reaction to a threat is to, nay say it as a form of self-comfort, I guess. And then there were some who were like, it's going to change everything. You're going to bring in money and you're going to ruin it. I think there's a lot of people. I think there's a lot of fear

that, like, we were opening a Pandora's box. Did you ignore that criticism? Or did sometimes, did it, like, make you feel bad? It fueled me. Matt is fueled. What part of it fueled you? When we first started the company, when we were out pitching to raise money, we pitched the company to probably three of the biggest public radio stations.

And none of them invested. And one of the pitches was the most insulting, condescending response we ever got from any investor ever. And that actually did fuel me. Right. Because I was like, we are going to show you. Do you remember what they said? They said, you haven't, you don't understand how risky this is. You haven't evaluated the risks. The quality of your presentation deck is beneath you. Wow. And the price that you've put on the company is expensive, bordering on outrageous. Bordering on insulting. And I was so mad. And I remember, and you were just kind of like, yeah, you were just disappointed. You're like, oh, that's what happens.

Yeah. But for me, that made me just want to prove everybody wrong. But meanwhile, I mean, you were growing. And, I mean, over time, you, I think you wound up raising like, I think, like, $27 million by 2017. And around that time, you had like around 100 employees, right? Yeah, over 100. Over 100. As you started to hire more and more people, especially people coming from public radio,

that's a challenging group of people to oversee. Okay, that's not, we're not talking about like software engineers or, you know, computer programmers. Who are super easy. Well, not comparatively easier, right? Where they cover sales teams or they're coming in and like, this is a group of highly intelligent, highly creative people with a million different ideas and not easy to manage. So I have to imagine that you guys ran into some challenges there. challenges? Yeah. Yes. Yes, we did. One of the things that I started to realize very late this year was that the hard thing about any media business is that there is a thing at the center

of any project that you're launching, of any show you're trying to launch, and that thing is a mystery. And the mystery is, will people listen to this or not? And there's no way to quantify why people will listen to things. There's no way to predict whether people will listen to things. It's unknowable. And dealing with that mystery, that's what every creative person is doing. And yeah, that presents a real hard management challenge. On the one hand, you have to manage the anxiety that comes with knowing that.

So people who somehow have figured out that mystery and are like doing successful shows, they know on some level that they don't know why what they're doing is working. working. And so you have to manage their anxiety about that. And then for the people who are launching something that isn't working, you can't tell them why, because you need them to have like figured out the essential mystery and they haven't figured it out. And so you have to just be like, you haven't figured out. I'm sorry. And it took us forever to figure. It took me forever to understand that. Because you had to, I mean, you're a business with a P&L and you've got to be profitable, which means that some shows that don't work have to be killed.

And some of those shows are done by people that you've known that are friends, which means that you are going to lose friends. Yeah. And I hired almost all my friends at the beginning, because all my friends were in the business. Did you have sleepless nights? I mean, we heard your anxiety when you were starting this company in the podcast. did you have even more anxiety after you started to gain traction and you started to see some success? Or did your anxiety mostly go away?

Oh, the opposite. The more successful we got, I think the more anxious I became. It became harder and harder to sleep. I would wake up in the middle of the nights and I really had never really done before. And I think it was about just the more successful we get, the more the bigger the stakes are, higher the stakes are. the more people that are that are depending on you. And you just have to contend with like, you can't make everybody happy.

And I love making people happy. It's like one of my essential character flaws. How about you, Matt? Did you have more anxiety as you started to actually see success with the company? Yeah, I think I did. and oftentimes like the moments of on the outside where it looked most successful inside it felt like the biggest mess and inside it felt like it was going to fall apart and that's and that's really hard to live through it and then and learning that actually that is the common experience of starting a company helps a little bit

as our coach says, because we go to a leadership coach says, like, just because you feel like shit doesn't mean you are shit. So we had an episode about Yelp. And Yelp was offered like half a billion dollars by Google a couple years after its launch. And Jeremy Stoppulman said, no, we're going to keep going. And Yelp today is valued it, you know, over a billion dollars and et cetera, et cetera. And of course, you guys were. approached or you began conversations with Spotify to acquire Gimlet.

They made an offer reportedly more than $230 million, a really big offer. I would have taken the money personally, but I'm just wondering, was there any part of you that thought, let's not take this, let's just keep going and build this into a billion dollar company? There was a small part, maybe. Not a big part. Nope. Not really. I don't know why Alex is making that up. No.

Nope. Nope. No, because we were, the company was going very well at the time. Actually, we were, we had the most momentum we'd ever had as a company. This was in the fall of 2018. Our audiences were growing faster than they had in years. We had come out of the summer and all of a sudden, like, there was more and more interested from advertisers in spending money on our podcasts. And we had a hit television show that we had produced for Amazon called Homecoming, starring Julia Roberts.

And so if you were around New York City at the time, like you couldn't turn around without seeing a 50-foot billboard with Julia Roberts' face on it, starring in Homecoming, which was based on our podcast. But there were a couple things that we just weren't. there were two like basically industry level challenges that we were confronting along with every other podcast company. And one was audiences are still having a really hard time discovering new podcasts. Like if you ask people how they find out a new podcast, they would typically say like word of mouth, like a friend told me or I found out about it from another podcast. But discovery is really hard. And then we weren't getting data that we could share back with our editorial teams about how, um, the shows were performing, who was listening to them,

and that kind of inhibited the monetization as well. And so we thought that for podcasting to become, like as an industry to become, to realize its full potential, those two things had to be addressed, and we couldn't do those alone. And Spotify, which is the world's largest music streaming platform, could do that together with us. Yeah. It wasn't even so much the money.

It was more like the, we felt, like we could achieve so much more by joining forces than we could independently. And a company like Spotify, that's their business. You know, they have this huge built-in audience that's already listening to audio. And it felt like that's, that's a great synergy is the word I'm thinking. I can't think of an, I can't think of a, I'm going to say synergy. You would have been, you would have been totally ridiculed to Planet Money if you said synergy. You would have been shamed in public radio if you use that word. I'm probably not the first person that said that word in this podcast, am I? So it makes total sense, right? Because Spotify's a giant, right? And full disclosure,

as you know, I did a podcast with Spotify. They paid a lot of money for Gimba, because its last valuation before the sale was like $55 million. And now you found yourselves very quickly. I mean, I know it was a long slog, but five years with a lot of money. And now you're presumably committed to working with Spotify for a few more years. Yeah. What do you think? I mean, are you going to, I don't know, you're going to buy, you know, 10 Teslas and a mansion and a house in the Hamptons? What are you going to do with your life and your wealth?

Yes. No. No, go. It is life-changing for us, both. Yeah. And someone asked me recently, oh, how are you? And I said, well, I'm really rich, and it turns out money doesn't make you happen. But it does make you safe.

Yeah. And so I feel an incredible amount of safety, knowing that I'm going to be able to put my kids through college, and I don't have to worry about that. And, you know, we've never owned a home, and now my wife and I are. going to buy a home. It is a life-changing thing. Yeah, I think right after it happened, I kept thinking, like, this feels like a big deal.

I don't understand why I still feel the exact same way. Like, it feels like an event that should just sort of give you a whole new outlook or something, and it didn't. It takes away this huge hum of anxiety that was always in the back of my mind about, like, money and the future. And that hum is gone,

And that's nice. But it sort of takes away nothing else, you know, which is surprising. I would have thought it would have thought it would feel different der. We, we, my wife's parents came from another country to this country and were as refugees and worked all night cleaning offices to pay for her to like live in America. And so I think when this happened, it was just like, like it was winning the lottery for them. And then we were able to pay off their mortgage and renovate their house

and have them come and visit our kids more often. And it's been just an incredible blessing. Do you feel like what happened to you, the outcome, and the story of Gimlet happened because you're super smart and talented and worked really hard or because you got lucky? I think it's mostly luck, but not in the obvious way. Like, I think for me it was the luck of being born into the family I was born into at the time that I was. So I had the luck of being in a family where my parents sent me, like, paid for my college.

And then we're in a position to financially support me so I could do unpaid internships producing radio because that was my passion. then they also sent me to business school. And that is like an extreme level of privilege. And then the other forms of luck are having met Alex when I did and having really good timing on the idea of starting a podcast, an audio podcast company in 2014. I definitely don't think I'm like smarter or more talented than your average entrepreneur. Yeah. It's funny. I think both things are true though. I think there's probably a lot of people who could have tried to start this company and it wouldn't have been successful. So I think there's something, we brought something to it. I'm proud of that.

I am proud of that. But I think that's the part that's easy to tell and most easy to overemphasize as you're looking back and especially as you're looking back. And I think it's important to remember that that's like a tiny part of it. Yeah. Both of you guys have the potential to be on the other side of the table. from where you guys were, right? The investors. You both can be investors now for other startups. And the other side to it is you both can give away a lot of money too. So do you, do either of those or both of those things appeal to you? I don't know about investing. Like, maybe. I don't know. Like, I'm still trying to figure out like what, what this all means.

Right. It seems only supporting that I would do that since so many people trusted us and it worked out for. us and for them. So it feels like I should sort of pay it forward in that way. Yeah. Matt? Yes. I will do both. Yeah, I've made a couple of angel investments and... You have. Oh, yeah. I've been told me. Wow. No. Interesting. And it's fun. Do you even cut Alex into that? Wow. Didn't even tip me in. It's hoarding all the deal flow himself. Do you want to be? We should talk about it. That's Matt Lieber and Alex Bloomberg, co-founders of Gimlet. And by the way, Eighth and final season of startup launched a few months after our conversation, and in it, you can hear many more details about the past few years at the company, including some very

serious money problems they got into last year and how they got out of them. Also, some great fly-on-the-wall moments from the Spotify acquisition, and a kind of surreal scene where Alex and Nazanin are having it another sleepless night, and for whatever reason, they find themselves hunched over a screen scrolling, I kid you not, through pictures of the royal family. And please do stick around because in just a moment, we're going to hear from you about the things you're building. But Oscar winner Regina King has been acting for more than three decades. But she says it's just in the last few years that she's really coming to her own. Being a mother had a lot to do with getting me to that space.

Regina King on her Hollywood Long Game. Next time on It's Been a Minute from NPR. Hey, thanks so much for sticking around because it's time now for how you built that. And this story starts back in the late 1990s when Casey Kerrigan was working at a rehabilitation hospital in Boston. I was seeing a lot of patients with knee arthritis. Especially women in their 50s and 60s. And what we found is that high heels affected pretty much in the whole body. She found that high heels don't just affect knees, but hips, feet, lower back, pretty much everything.

Now, Casey's specialty is physical medicine, so she started to do some research. And she soon realized that high heels are not the only enemy. Women's shoes in general have all sorts of problems. Too narrow of a toe box, too narrow of a forefoot, a lack of true spring in the soul. And some of Casey's younger patients would say, yeah, I know these shoes are bad for me, but I want my feet to look great and fashionable. But gosh, do we really want to be walking around in shoes that are doing this? I mean, let's walk around and choose that are going to be the easiest on our joints.

So at this point, around 2009, Casey decides to quit her very safe, very good paying job at the University of Virginia Medical School. And she sets out to design a kinder shoe for women. When I left, I thought, ah, you know, this shouldn't be too hard. just need to make a soul that's flat and springy and that accommodated the natural anatomy of a woman's foot. How hard could that be? Actually, pretty hard. For starters, no shoe factory in the world seemed set up to make the kind of shoe Casey had in mind, which was wide in the toe, totally flat on the bottom with a super springy soul.

Nothing in the design is like meant to just be pretty or everything's functionally based. So using computer-assisted design software, Casey taught herself how to make those first shoes. But remember, she couldn't find a manufacturer to make them. So she and her husband took their savings. They bought an old warehouse, and they built it with all kinds of equipment. I bought this big filament winder to make these carbon fiber springs. I bought a water jet saw. Then there's ancillary things like you need a, like a, shoot, what do you call it?

By the way, this is all happening when Casey is all. already in her late 40s. Oh, chiller, that's it. So you need a water chiller. She'd been a medical doctor, then a tenured professor, and suddenly, she's making shoes. I never thought, yeah, I'd ever be a cobbler, right? In about 2011, Casey's first shoe was ready to sell.

It was kind of a heavy, chunky leather sneaker. You know, these were like orthopedic-looking shoes. I've got to be honest. Not really attractive because they had real thick, souls. But a few years later, Casey found a better material for the souls, rubber pellets, the same stuff they make those super bouncy balls out of. And at roughly the same time, 3D printing was becoming cheaper. And I thought, hmm, wait a minute. If we 3D print it, I can basically create the soul that I could only imagine ever making, you know, with traditional

manufacturing. So now Casey could make thinner and more flexible souls for all kinds of new designs, like a tennis shoe and a ballet flat and even a platform sandal with a fluorescent blue bottom. And it's comfortable. That's the thing, is when you step on our souls, it's spring. I mean, women, they'll smile because they've never experienced it before. Casey calls the shoes Osh, which is an anagram for the word shoe. Both she and her husband run the company out of Charlottesville in Virginia.

Last year, just selling from their website, they made about three-quarters of a million dollars. If you want to find out more about O'S Shoes or hear previous episodes, head to our podcast page, how I built this.npr.org. And of course, if you want to tell us your story, go to build.npr.org. And thanks so much for listening to the show this week. You can subscribe at Apple Podcasts or wherever you get your podcasts. And while you're there, please do give us a review. You can also write to us at hibt at npr.org. And if you want to send a tweet, it's at How I Built This or at Guy Raz.

Our show is produced this week by James Dela Hussi with music composed by Rumtin Arablui. Thanks also to Candice Lim, Julia Carney, Sanaz Meshkampur, Neva Grant, and Jeff Rogers. Our intern is Sequoia Carrillo. I'm Guy Raz, and you've been listening to How I Built This.