ALEX BLUMBERG: From Gimlet, I’m Alex Blumberg and this is Without Fail, the show where I talk with artists, athletes, entrepreneurs, visionaries of all kinds, about their successes and their failures, and what they’ve learned from both.





Back when I was first thinking about starting my own podcasting company, when the idea was just getting formed in my brain, I had no idea how to even begin. This was in very early 2014, before I’d met the person who would become my co-founder, Matt Lieber. Before I’d talked to any investors about helping fund me. I was still working at This American Life, still running Planet Money, and a friend told me about this podcast that she liked. It was called Professor Blastoff, shoutout to any Tig Notaro fans out there, and I noticed in the liner notes that it was made by a company. A company called Earwolf. At the time, I’d never seen that before. Most podcasts that I knew of, were made either, just by individuals, or were part of some branch of public radio somehow. There weren’t what you’d call, podcast production companies, or at least that’s what I thought. But here was this one called Earwolf that was already doing what I was just beginning to think about doing. And aside from Professor Blastoff it had a whole bunch of other podcasts that it produced — Comedy bang bang, How Did This Get Made.... I thought, I got to talk to these people. And so I sent a blind email through the contact portal on the Earwolf website.





ALEX BLUMBERG: So do you remember getting that -- do you remember getting that email?





JEFF ULLRICH: Of course! That email was one of the most exciting emails I had gotten in a long time, because I had thought you were contacting me in your capacity as a producer for This American Life.





ALEX BLUMBERG: Uh-huh.





JEFF ULLRICH: And I was like, "Oh, my goodness. You know, nobody ever pays attention to what we're doing here, and my heroes want to talk to me about this. Like, they're going to do a segment on podcasting, and maybe I'll be on it." Like, I started having these delusional fantasies about being, like, the centerpiece of a very important story on This American Life about this, like, emerging medium. And instead, you just wanted free advice.





ALEX BLUMBERG: [laughs] That's right. I wanted free advice.





ALEX BLUMBERG: Today on the show, I’m talking with the person who answered my blind email: the founder and CEO of Earwolf, Jeff Ullrich. Over the years since I sent that email he’s become a good friend, who’s provided lots and lots of free advice. And a quick warning before we get into it, there’s some mild swearing in this episode.





In many ways, Jeff is an original podcast pioneer. He was a podcast entrepreneur long before I was even thinking about starting a podcasting business. In fact, Gimlet might not have been successful, or even possible, without the early work Jeff did in building out the business model to support the podcasting industry. And Jeff was a pioneer in another way as well. In 2015, he sold Earwolf, for a reported 50 million dollars, the first major sale of a podcasting company. Of course there have been lots of sales since then — including my very own company, Gimlet, which we sold earlier this year. But Jeff’s sale came first. He was the one who made it official: podcasting was a real industry, with real money to be made.





Over the years, I’d gotten the story of Earwolf in dribs and drabs from Jeff, and I thought I knew it pretty well. But when we sat down together, and he told me the story in full, I realized there was a lot that I had no idea about. And that even though, in my head, I always owed a debt to him for what he’d built, I didn’t know the half of it.





One thing I’d never fully realized? How unlikely the whole thing was. The Jeff Ullrich who started Earwolf, he wasn’t a guy with a lot of audio experience, he didn’t have a Stanford MBA... Not even close.





JEFF ULLRICH: I was a failed single shingle business manager. I had been helping people, you know, manage their money, um, manage their lives. You know I wasn't working with people who had massive careers. I was working with, like, working actors and comedians. I was an alcoholic, like an active alcoholic. I was drinking a lot. And I would spend a lot of time drinking with my clients. And it wasn't going well. I wasn't enjoying it. I wasn't as good at it as I needed to be.





ALEX BLUMBERG: And when you say you were managing clients, just give me an example of, like -- what are you doing for that person?





JEFF ULLRICH: Um, it was less about money really at the end of the day, than it was managing responsibilities. So I worked with people who really needed help. And frankly, I don't mean this as a -- as a dig. I think a lot of adults never learned personal finance. They never learned how to manage and organize their lives.





ALEX BLUMBERG: Right.





JEFF ULLRICH: And so all of a sudden you find yourself at 42 and you haven't filed your taxes in six years.





ALEX BLUMBERG: Oh, my God.





JEFF ULLRICH: And you've got four outstanding parking tickets and they're going to put a boot on your car. And what's supposed to be your office is really like a room where you hoard paperwork.





JEFF ULLRICH: And so people would hire me -- and it would be like, "Okay, well we're going to take care of this, that and the other thing, and we're going to go meet with the accountant and we're going to set everything up online." A lot of this was taking people offline and putting them online and teaching them how to manage themselves digitally. All of that.





ALEX BLUMBERG: So you're doing that. You're taking these people who are sort of whose financial lives anyway are something of a mess, and you're coming in and trying to put them into order. But at the same time you said you were an alcoholic, and you're ...





JEFF ULLRICH: Yes.





ALEX BLUMBERG: ... drinking a lot, and you'd go out drink with your clients. Like ...





JEFF ULLRICH: It doesn't match, does it?





ALEX BLUMBERG: No.





JEFF ULLRICH: Well, so I was -- I was high-functioning, what they call high-functioning. And I was really good at a lot of things, including being a high-functioning alcoholic. I was -- I was great at budgeting and I was great at doing what I said I was going to do. And these are things that aren't typically associated with alcoholism, but I was good at it. But having said that, I did not excel at what I was doing because I had a problem, you know? It got in my way and it prevented me from recruiting the types of clients that were going to help me build my business. I remember being out at a karaoke thing on a Monday night at, like, midnight, and I was shitfaced, and I could barely even sing the words to the -- it was an Avril Lavigne song, I'll never forget that. And like, Drew Carey was with us, and he was like, you know, kind of a big deal. And I couldn't even sing the words to the song. I remember the next morning, like, waking up. I had come home, I was blackout drunk, and I had written myself an email basically saying like, "You can't do this anymore." saying that, you know like, "I'm never going to be able to get a client like Drew Carey if I'm sloppy like that.





ALEX BLUMBERG: Mm-hmm.





JEFF ULLRICH: And I didn't remember any of that until I woke up and I read the email to myself. And so I was good at servicing the clients I had, because they had fairly low expectations.





ALEX BLUMBERG: And how many of them -- how many of them were -- had their own problems with alcohol, do you think?





JEFF ULLRICH: Several.





ALEX BLUMBERG: Yeah.





JEFF ULLRICH: At the end of the day if you're gonna be a successful alcoholic, you're gonna spend years building scaffolding -- alcoholic scaffolding -- around everything.





ALEX BLUMBERG: Uh-huh.





JEFF ULLRICH: And part of that is really subtle to people who aren't the schemer, you know? It's like you make friends with people who go to bottomless mimosa Sunday brunches every Sunday, because that's what they do, because then that's an opportunity to go drink where no one's going to pin it on you. You know what I mean? You're not the one driving the choice to go drink alcohol at 11 am on a Sunday.





ALEX BLUMBERG: Mm-hmm.





JEFF ULLRICH: And so for me, if I'm helping other alcoholics who maybe aren't as high-functioning or at least in the way that they want my help, then I kind of look like a shining star in that scenario.





ALEX BLUMBERG: Right.





ALEX BLUMBERG: While Jeff was doing all of this -- drinking too much, getting paid by the hour to bring order to the lives of not very well known actors and comedians, and generally feeling disappointed with himself -- he started listening to podcasts. Including some of the ones I was making at the time: This American Life, Planet Money. As well as others like, WTF with Marc Maron.





And all this listening gave him an idea. He should start his own podcast. A podcast in which he’d talk to people on the business side of entertainment, people like accountants and booking agents. He would make a show that people like his clients, and potential clients, would want to listen to, and maybe it would help him drum up business.





And around this time an opportunity arose. There was a comedian named Scott Aukerman who hosted his own podcast, called Comedy Death Ray Radio. Scott Aukerman needed a fill-in host for a taping one day, and he reached out to one of Jeff’s clients, a comedian named Jerry Minor.





JEFF ULLRICH: So Jerry Minor was a friend and a client, and he was trying to help me launch my podcast because he knew a bunch of people. And he was going to guest host for -- for Scott. So he's like, "You should come with me and you can talk to the people who do the podcasts there and you can try and learn about it."





ALEX BLUMBERG: So you were doing what I was doing.





JEFF ULLRICH: Yeah!





[CROSSTALK]





JEFF ULLRICH: I was -- I was you.





ALEX BLUMBERG: Okay. You're like, "This guy has a podcast. I'll ask him how to do it."





JEFF ULLRICH: Yeah.





ALEX BLUMBERG: Okay.





JEFF ULLRICH: I'll ask him. Well, Scott wasn't even there. The whole point was that Jerry had to sub for him because he was out of town. But the engineer was there, a guy named Stu. And I don't remember what Stu and I talked about outside of one thing, which is that he told me the show had been downloaded a million times in the first nine months. They had no website. They had no, like, kind of marketing presence outside of an occasional feature in the iTunes podcasting section. And I just kind of became an opportunist at that point. I.. to me -- and you'll probably laugh at me now, because you know as well as anyone, like, a million downloads in nine months is not something to start a business on. But at the time, I was like, "Oh, my goodness. So many people are finding this and doing this, even though it's really hard."





ALEX BLUMBERG: Yeah.





JEFF ULLRICH: 2010, it was -- it was really difficult to listen to a podcast.





ALEX BLUMBERG: Right.





JEFF ULLRICH: Maybe you had an iPod. You probably didn't have a smartphone.





ALEX BLUMBERG: Right.





JEFF ULLRICH: And everything was really, really difficult. Early days. So in my mind there was a lot of people who went through a lot of effort to make sure they could listen to this podcast. And that told me that there was something special happening. And I started doing my research.





ALEX BLUMBERG: Jeff got his friend Jerry Minor to introduce him to Scott, and after meeting him once, they decided to meet again in March of 2010, in Jeff’s apartment — Scott and Jeff and Jerry and Stu, the engineer.





And originally, this meeting was supposed to be narrow in focus, how could they build up Scott’s podcast? But in the weeks leading up to this meeting, Jeff had been thinking about a much bigger, grander idea. An idea he sprung on Scott for the first time during this meeting.





JEFF ULLRICH: I presented him with the world's worst presentation. I still have it. It's so terrible. It was 15 pages, terrible design, not well-organized, but it was me saying, "Let's not just do this for you. Let's create a network. Let's do this for a hundred comedians. Nobody wants to learn Pro Tools. Nobody wants to build their own website. Nobody wants to sell their own t-shirts or ads. Let's just make it really easy for people to show up and have fun with their friends and make some money."





ALEX BLUMBERG: In other words, let's make this a real business together.





JEFF ULLRICH: Yes And at the time it was gonna be me and Jerry and Scott. Jerry is going to put in, like, $40,000. I was going to run it. Scott was going to be Chief Creative Officer. And we were going to do it together. And then Jerry decided that it was too risky, or I don't know, it wasn't for him. And so Scott and I wound up having an emergency meeting on a Sunday night. And I had my, like, 50-pound Compaq laptop with, like, the world's largest charger. And I started just running the numbers in a spreadsheet, and I was like, "I think we can get away with $30 grand. Darlene, my wife, had about $22,000 in her Roth IRA. And so I was like, "We can afford $24,000. If you can put in six, let's do this. We don't -- we don't need a third partner." And Scott was like, "Okay, let's do it." And then the next day he's like, "Uh, my business manager says I can only afford $3,000." [laughter] So I had to go back to Darlene. And, like, beg her to let me scrounge up $3,000 more. Um, and we did it. And so we put in 27 and he put in three, and I gave him 15 percent of the company in exchange for being the Chief Creative Officer for free for the rest of his life, or as long as Earwolf existed. So we had 30 grand. And off we went.





ALEX BLUMBERG: Um, how were you feeling?





JEFF ULLRICH: I was feeling really excited and really optimistic. I saw so much room to run. And it was exciting, you know? It was new and nobody really cared about what we were doing or had a lot of faith that it mattered.





ALEX BLUMBERG: Uh-huh.





JEFF ULLRICH: The stakes were low publicly, but they were really high for me, because, like, I'm an alcoholic that was you know I started the business 19 months before I got sober. So I was on the -- the last legs of 16 years of drinking, and didn't know it at the time. So everything was just kind of crazy and exciting and new, and I would hire people and they'd be like, "Well, I don't know if I'm qualified. Like, I don't know anything about podcasting." And I was like, "I don't know anything about podcasting." You know, everything we do is something that's never been done before today. So if you can embrace that environment then we're good.





ALEX BLUMBERG: Do you remember the first dollar you made?





JEFF ULLRICH: Yeah. It was very, very early days. Scott was going to Chicago to do a live podcast for the Just For Laughs Comedy Festival, and they had offered him, like, a flight and a dollar per ticket at the door or something. And he was gonna say yes, and we had just started working together. And I was like forget it. Send them to me. And I negotiated a deal to pay for me and Scott and the engineer to all go there, all expenses paid, plus half of the door. And then I produced a second show the next night outside of the festival. It was at, like, a Phish cover band place called the Kinetic Playground. And we sold out in, like, an hour. We sold a hundred seats -- for 30 bucks apiece, and we sold 100 standing room only for 20 bucks apiece. And I rented the place out for 300 bucks. So I made, like, four months of operating expenses in that one night by adding that show, and then we record it and we sold it for three bucks a pop on our website. So we made even more money.





ALEX BLUMBERG: So -- and also it strikes me, like, you said that you sold the podcast on your website. So you weren't at this point putting up podcasts and selling ads on them yet.





JEFF ULLRICH: No, the ad stuff came -- came later.





JEFF ULLRICH: We, we got by on donations, merch and live shows. And selling live shows as premium content ...





ALEX BLUMBERG: Uh-huh.





JEFF ULLRICH: For, you know, I don't know, a year. So that -- that trip to Chicago was the first money that we ever made.





ALEX BLUMBERG: And -- and are you -- like, if that had been me, like, I was so, I remember the first dollars that we made feeling so thrilling, because I'd never experienced that before. But you were a businessman for your whole life. So was it -- did you have the same thrill?





JEFF ULLRICH: Yeah. No, it's different. It -- it feels like a superpower when you realize that you can take, like, an idea and a set of resources and organize that in a way where, you know, people will give you more money than it costs you to do it. That's a very thrilling thing to discover.





ALEX BLUMBERG: Yeah.





JEFF ULLRICH: And even if you know that it's possible and that people do it every day throughout the world, doing it yourself for that first time is -- is truly thrilling.





ALEX BLUMBERG: Coming up, Jeff goes from those first few thrilling dollars to many, many... slightly less thrilling dollars. That’s after the break.





[BREAK 1]





ALEX BLUMBERG: Welcome back to Without Fail and my conversation with Earwolf founder and podcasting pioneer Jeff Ullrich.





To build their network, Jeff and Scott needed shows. They already had Comedy Death Ray Radio... which they eventually renamed Comedy Bang Bang... but they needed more... So they started pitching people who they thought would make good hosts and taking pitches from people who approached them with ideas. And little by little they built out their stable of shows, podcasts like How Did This Get Made… where host Paul Scheer and a group of regulars listen to and make fun of some of the worst movies ever made.





PAUL SCHEER ARCHIVAL: What’s up people of the world? This is Paul Scheer. You might know me from human giant or FX’s the league, I play andre on that show. And there’s one thing you may not know about me, and that is, I love shitty, crappy movies.…[dip]





ALEX BLUMBERG: There was a podcast called Sklarbro Country...hosted by two comedians who are also brothers, Randy and Jason Sklar.





SKLARBRO COUNTY ARCHIVAL: Remember we had an idea we got really high, like, right after college and we had an idea to sell pringles individually?

Mhm.

Individually wrapped.

Individually wrapped Pringles. That was a bad idea.

That was a terrible idea.





ALEX BLUMBERG: And there was the show that I first discovered, Professor Blastoff…





PROFESSOR BLASTOFF ARCHIVAL: There’s the id, superego, and ego.

So explain every…

Well the id is the primal, I want to have sex, I want to eat that.

Kyle!

I’m sorry

Is that how you get into sex? [laughs]





ALEX BLUMBERG: These podcasts attracted fans, Earwolf’s audience continued to grow. But most of the shows, you could download for free, and not everyone was buying t-shirts, or going to live events, or donating money. And Jeff’s plan had always been to go beyond that as a revenue source. His plan had always been to start advertising on Earwolf’s shows… so he started looking around for a way to make that happen.





JEFF ULLRICH: our first kind of quote unquote "real" advertiser was LegalZoom. They had never done a podcast before. They had done radio stuff. They're considered direct response advertisers which, in the world of advertising is not quite as exciting as a brand or awareness advertiser would be, because if you don't deliver, they're gonna stop advertising with you. you know, there are links that you have to send people to.





ALEX BLUMBERG: Right. A direct response advertiser is like -- it’s anytime you hear a promo code, you know, that's a direct response advertiser. And anytime you just hear it's like, you know, "Ford. We, you know, like, we're -- we're moving things forward," or whatever it is, that's sort of like a brand advertiser. Like, Ford isn't advertising on podcasts necessarily because they want to give you an offer code to buy -- to buy a car. so the direct response advertisers are the ones that are sort of like, you gotta perform basically for them, otherwise they won't -- they won't come back.





JEFF ULLRICH: Yeah. And so generally, people don't like that because it's more variable and it's challenging, and if you don't have the metrics to prove that it works then the money goes away.





ALEX BLUMBERG: Right.





JEFF ULLRICH: But for us, that was a really great, uh, opportunity. And so LegalZoom signed on to a three-month deal . And it was bad. I mean, that first month I thought they were gonna ask for the money back. And I was -- I was really upset and concerned …





ALEX BLUMBERG: Because, like, nobody was clicking on the offer code, basically.





JEFF ULLRICH: Nobody -- nobody was doing -- right. Nobody was putting in the offer code . And so I was like, "Well, my whole hypothesis that these rabid fans who are so dedicated to the shows and the hosts, that they're going to support the advertisers is flawed. It's wrong. And I can't build a real business around just donations and t-shirt sales. It's never gonna happen." So it was a rough couple of months. I was worried I wasn't going to have a test case to sell to other advertise -- you know what I mean? Like, it just spirals into like, "Oh, my goodness. This is gonna end everything, this one three-month experiment." So they canceled, they were like, "It's not working. Sorry, we can't come back." And then, three months after it ended, they called me up and they're like, "You're not going to believe this, but we have more conversions on the code in the three months after the ads ran than we did during the three months that the ads ran. And we want in. And that phone call changed everything, all of the things that I had hypothesized, that I put in my pathetic presentation to Scott, were starting to sound like maybe they could come true.





ALEX BLUMBERG: There are a few reasons why the LegalZoom ads ultimately worked after failing at first, things that Jeff only put together after the fact. One, people listen to podcasts on demand. So they weren’t necessarily downloading the episodes and hearing those ads the minute the podcasts posted. And two, people don’t act on ads the first time they hear them. It takes repetition. A person has to hear an ad close to a dozen times before they think “Oh you know what? I actually am about to start a business. And don’t feel like hiring a lawyer for thousands of dollars. Maybe I should just use LegalZoom.” Not only that, but the hosts gradually got better at reading the ads, which made the ads more convincing. This was the kind of stuff Jeff was learning over time. Applying it back to the business, and helping it grow. And grow it did.





JEFF ULLRICH: the first year we had 19 grand in revenue. The second year ...It was like, $19,000, $276,000, a million, $2.4-million, $8-million.





ALEX BLUMBERG: Wow! $2.4 to $8 is pretty amazing.





JEFF ULLRICH: Yeah. We -- we basically grew, like, 200 percent a year, five years in a row.





ALEX BLUMBERG: So -- at the -- and so at the time I called, I think you were already -- you were into the millions in revenue stage of the -- of the business.





JEFF ULLRICH: Yes.





ALEX BLUMBERG: You were -- you were up and running. You had -- things were working. You had it down.





JEFF ULLRICH: Yeah, we were -- we were a machine at that point.





ALEX BLUMBERG: Right. And so that was -- that was -- so that was somewhere in 2014. In 2015 ...





JEFF ULLRICH: And mid -- Midroll was a year -- a year old at that point, too.





ALEX BLUMBERG: Midroll. This is a key part of Jeff’s story. It was a second company that Jeff launched, on the side, while he was still running Earwolf. So, by this point, Jeff had gotten sober, and he felt ready to take on what seemed like this huge business opportunity, something that kept happening to him as he was running Earwolf. He would be wooing an advertiser to come on one of Earwolf’s shows, Comedy Bang Bang or How Did This Get Made -- and the advertiser would say to him, hey, can you also help me advertise on some other show, a show that isn’t part of Earwolf’s network?





JEFF ULLRICH: it was like I had the same conversation four different times with four different people, which was like, "Well, I need you to bring, like, your level of service and professionalism and data to all of what I'm buying. Can you do that?"





ALEX BLUMBERG: The advertisers are asking you this,





JEFF ULLRICH: Yeah, the advertisers are, like, begging me to sell them other people's stuff. You guys have the best reporting, your ad reads are the best, the results are the best, the service is the best. Um, like, I -- if I have to deal with 50 more -- 50 comedians who don't know what they're doing individually, I'm going to kill myself. You know, like I can't -- I can't do this anymore. I can't advertise on podcasts anymore. And I said, "I really think that this is gonna be a big business, and that I can do it." And I went to my wife Darlene and I said, "Look, I've been sitting on this idea for nine months at this point." And we had had at that point, an eight-month-old daughter, and I had been working, you know, 18-hour days, seven days a week. I am not even a year sober. And she, for the first and only time in our marriage, she said "You know what? I forbid you from doing that." She's like, "There's no way you can add more. You can't start another company. You're struggling to, you know, make the one you're running work. And it's hard for you, and it's hard for us." And then I did what I've only done once and haven't since, which was I ignored her. And I basically started spending time that otherwise I would have spent on Earwolf on Midroll. . And, you know, I did it myself. I didn't have any employees And we went from there. We launched on April 1st, 2013, was our first episode of a podcast we sold ads on that wasn't an Earwolf show. We did $532,000 in revenue in the first quarter of operation, and we ended up doing $2-million in the first nine months.





ALEX BLUMBERG: Midroll financially, was a much bigger success than Earwolf had been. Because not only did it serve the growing number of advertisers who wanted in on podcasting, it also served the booming number of people out there who wanted to start their own podcasts. Like me. Midroll solved a huge problem for someone like me, just starting a podcasting company: it gave me a built-in business model. All I had to do was make the podcast and get people to listen to it. For a small cut, Midroll would sell the ads and bring in the revenue for us. And for the first year of Gimlet, we did use Midroll, before we built out our own sales team.





But what was an easy solution for me and lots of podcasters, wasn’t so easy for Jeff. Because even though podcasting was taking off, and getting more and more popular, it was still fairly niche. And this is the weird cognitive dissonance that comes with early success. The bigger you get, the more you realize how little you still are in the grand scheme of things.





JEFF ULLRICH: I think that for, like, three years, I was the only person trying to convince everybody in the world that podcasting was important, and that it was real, and that you should invest in it, and you should do one, and you should advertise on them, and you should buy the t-shirts. You know what I mean?





ALEX BLUMBERG: Yeah.





JEFF ULLRICH: And it was relentless. It was a -- it was a rough road. A lot of time on the road, a lot of time on the phone, just banging the drum over and over. Please believe me. Look, here's my data, here's my information, here's my inspiration. Trust me. You know, your boss will think this is a good idea when it's all said and done. There's a lot of like, "But my boss won't believe this."





ALEX BLUMBERG: When you're talking to, like, account managers at, like, various brands.





JEFF ULLRICH: Yeah, low-level people at major agencies in New York where, you know, I'm not talking to anyone who's more than, like, 24 years old, A lot of that, you know? And so I got a lot of nos. You know, like, I'm pouring my heart out in proposals to people and I'm getting ghosted.





ALEX BLUMBERG: Yeah.





JEFF ULLRICH: It was hard times. and I think it took a toll on me that I'm frankly still paying the price for. You know like, to even use the word "fatigue" is -- is an understatement. And half of that time or more, I was -- I was drinking or trying to not drink. I weighed probably 225 pounds. Like, right now I'm 170. I didn't exercise. I didn't sleep. I ate like shit. I smoked two packs a day. I could not have been any unhealthier, really. I mean, outside of doing, like, hard drugs which I didn't do, luckily.





And it had hit that critical mass where there was more incoming. You know, I had to say no to more than I said yes to. But getting to that point was so exhausting and so difficult that I was struggling.





ALEX BLUMBERG: He was struggling so much that he did something fairly unusual. He took a sabbatical. He said to his team, I need to get away, and he took off, for 5 weeks. He visited friends in Colorado spent a week by himself, driving through Wyoming and Idaho. Spent a lot of time, he says, staring at the Tetons. His hope was that his time away would give him the hard reset he desperately needed.





JEFF ULLRICH: I got back from my break and -- I'll never forget this. It was the day after Memorial Day. 2014. And somebody who worked for me, I had a 9:00 am meeting with her on the books. And she doesn't show up. And she didn't -- her phone went straight to voicemail. She didn't respond to email or text. And I didn't hear from her until 9:40. And then also, I had walked in the studio that morning and it stunk like rotten fish. And we had this brand new expensive studio, and I had a huge client coming in, a talent that I was trying to convince to do a show with us that day. And I'm like, "I can't bring her here with this rotten fish smell." And I said to the studio manager who was sitting right there, and she's, like, typing away on her computer, and I'm like, "Do you smell that?" And she's like not -- she doesn't look up from her computer. She's like, "Yeah, I smell that." And I'm like, "Well, what are we gonna do about it?" And she just kind of shrugged her shoulders. She's like, "Yeah, I don't know." And I was, like, standing outside of my office, and I just knew. I was like, "I got to quit. I'm done." Like, five weeks away from this and I'm -- I'm 10 minutes in and I want to kill two people already. So I'm done. Like, this is not something where a day off is gonna fix it. A vacation isn't gonna fix it. Like, I need to be a non-employee, you know? I need to get out of this.





ALEX BLUMBERG: I just want to tease apart, like, sort of what went into that -- into that decision, because, like, there was all the time that you'd put in, and all the work that you had spent, and sort of like there's just this sort of like the lingering exhaustion of all of that. But then there's also this idea of, like, coming back and, like, just -- just, like, how...it doesn't sound like enough to quit, basically. The story that you told it's like, okay so somebody was late. The studio stunk. Wait, what? Why did you want to quit?





JEFF ULLRICH: Yeah. No, it -- it was -- it was this sense that it was never gonna get better. That I cared too much -- unreasonably much, and that I didn't know how to make everybody else care as much as I did. And the truth is is that all this is bullshit, you know? I had, like, a ton of great people who cared so much, who did great work. Um. But it was hard, you know? I did feel like the buck stopped with me on everything.





ALEX BLUMBERG: Right. I guess it's sort of the classic conundrum which is, [deep breath] you are an all-in kind of guy. I think you have to be. Like, you were all-in on this. You were working whatever, you know, more than 12 hours a day or 15 hours a day, seven days a week. And, and in the beginning, that's the fuel, that's the thing that's growing it. But at a certain point you have to be able to modulate the amount to which you care or something. And it's -- and it sounds like you were trying to modulate the amount of your investment, like, your psychic sort of investment in the company. But no matter how much you dialed back your sort of on-paper duties, you couldn't dial back the amount that you actually cared.





JEFF ULLRICH: That's true. I had become the podcast guy. I spent three years as, like, the card-carrying member of, you know, join my cult of podcasts. And the idea of not being that per -- like, who was I then? You know what I mean? And I really struggled with being on the sidelines uh, and having the vision, but not being involved in the execution. But at the same time, like, I wasn't -- I was no longer capable of doing the execution because I was so burnt out. So I was in a conflict that was not gonna get resolved.





ALEX BLUMBERG: How do you resolve an unresolvable conflict? That’s coming up after the break.





[BREAK 2]





ALEX BLUMBERG: Welcome back to Without Fail and my conversation with Jeff Ullrich.





In early 2015, Gimlet was just a couple months old, but by then, Jeff had been running Earwolf for almost half a decade. Half a decade of non-stop work, not really taking care of himself at all, barely seeing his wife Darlene or their young daughter. And he was just getting more and more miserable and frustrated at work.





JEFF ULLRICH: Everything just felt like I needed to stop. I needed to start taking care of myself. I needed to be a better dad. I had been an absentee father for two-and-a-half years. It was -- it was time.





ALEX BLUMBERG: I remember you telling me, and I don't know how much this was, like, real or, to make a point or, like -- or if it's something that you're -- I remember you telling me, like, you were literally worried that you might die if you kept working.





JEFF ULLRICH: Yeah.





ALEX BLUMBERG: Was that true?





JEFF ULLRICH: Yeah, it was, it's true.





ALEX BLUMBERG: Why were you -- why were you worried that you would die?





JEFF ULLRICH: My lifestyle had just become so unhealthy, and I had become so stressed, just all the time, and I didn't know how to deal with it. And, like, my -- my own father was an entrepreneur. And he drank some -- he's not an alcoholic, but you know, like, he drank and he smoked and he didn't eat well and he didn't exercise and he didn't sleep and he was stressed all the time, and he had a stroke at 44 years old. So I had that as a model of how this could all play out if I wasn't careful.





ALEX BLUMBERG: Mhm.





JEFF ULLRICH: I just knew that, like, I was -- I was setting myself up where, like, I was gonna get the divorce papers from my body sooner rather than later if I didn't do something about it. And ultimately, Darlene is -- is smarter than me in almost everything, and she knows me better than I know myself. And she just looked at me and she's like, "You know, if you own one share of this company, you're gonna care too much about it. And I really think that you should consider , taking it seriously and selling, because, you know, this is like your first love. In terms of, like, entrepreneurially, you know? This is like your first real business that you started and built. You're gonna sell it. You're not gonna be a part of it, and it's gonna be like ... It's gonna take you a couple of years to get over it. And, you know, when do you want to start the next chapter of your life? You know, do you want it to be when you're 50? Or do you want to be when you're 42?





ALEX BLUMBERG: In other words, sell now, so you’ll have time to get over it, move on, and maybe do something else with your life while you’re still young.





And the time was right for selling. In part because of Jeff’s efforts, podcasting was starting to get attention. He was bringing in big money. So, Jeff started considering the idea of hiring a banker, and running a process to sell. But when he started discussing this idea with his friends, a lot of them tried to talk him out of it.





JEFF ULLRICH: I talked to some smart people -- including you -- before committing to going down that path. And nobody thought it was a good idea. And someone who was really smart was, like, trying to use the ego. He said, "Do you know how rare it is to be essentially like a media mogul these days? No one builds a business without someone else's money. And you have an opportunity to build, like, a billion-dollar business that no one else can tell you how to run. And in the media world that's, like, unheard of. But you know, another big consideration was my mom was 62. She was a deputy at the Cook County Sheriff's Department. She, you know, was trained in, like, lock-up and riot gear, and she was gonna have to work 10 more years before she could retire.





ALEX BLUMBERG: Right.





JEFF ULLRICH: And if I sold then, then she could retire right away. And I thought to myself, "You know, how do I tell my mom that I rolled the dice on building something bigger. And then, you know, there's some sort of global recession and I got to grind it out for 10 more years. And sorry, but, you, you have to keep working.





ALEX BLUMBERG: And so, Jeff decided to do it. in late 2014, he officially hired a banker and told him, go and see if there are any buyers out there. Which is the way these kinds of things usually work. But there were definitely some non-standard parts to the process Jeff wanted to run. So usually, acquisitions like this include a stipulation that the founder has to stay with the company, for a little bit of time at least, to oversee the transition. But Jeff’s whole point here was to remove himself entirely. If he was in even a little bit, it would be too consuming. So he told his banker: make it clear to potential buyers that the founder won’t be sticking around. And the process worked. In July of 2015, E.W. Scripps, a media conglomerate out of Ohio, bought Jeff’s company for $50 million.





But Scripps had a stipulation of their own. Because Jeff wasn’t coming along as part of the deal, they didn’t want him out there potentially starting a new company that would compete with them. And so, they made Jeff sign a noncompete clause -- he was forbidden from having anything to do with podcasting for FIVE years. He couldn’t host a podcast, he couldn’t start a company involved in podcasting, he couldn’t do any consulting on podcasts. In effect, he had to exile himself completely from the industry that he had helped build.





ALEX BLUMBERG: I remember thinking, hearing you talk about it, and it -- it seemed like it felt like pretty cold turkey. Like all of a sudden, this is your life, this is the thing you're thinking about for a long time, it's the thing that had been your identity. And now, once the sale closes, you are by law forbidden from engaging in it for five years.





JEFF ULLRICH: Yeah, yeah. It's weird, right?





ALEX BLUMBERG: Was it?





JEFF ULLRICH: [laughs] So it was a huge relief to be in a position where I couldn't even -- so I had gone from having four calls a day with people who are like, "Can you tell me about how to start my podcast?" Like, you know, pick your brain stuff. To, "Sorry, I can't. I could be sued for, tens of millions of dollars if I give you advice on how to start your podcast." And it was liberating to be able to blame a contract to disassociate myself from something that, as much as I loved and as much as I had invested myself in it, I knew it was over, you know? It was over for me.





ALEX BLUMBERG: But it was still complicated. Right around the time Jeff was officially recusing himself from the podcast conversation, I was entering it. Every week a new article would appear about how podcasts were the hot new medium, and it seemed like every week my co-founder Matt and I were on the phone with a new reporter talking about how we were at the dawn of a new golden age in audio. And it wasn’t just us, everyone in the industry was getting quoted, was getting interviewed. Except, of course, the guy who’d help start it all … Jeff.





JEFF ULLRICH: I did a really good job of building a business and operating business and growing it. I did a terrible job of doing press and promoting that business. I was not out on a circuit. I wasn't doing interviews. People weren't writing profiles of me in Fast Company. We built this really successful, profitable business largely in anonymity as it related to the rest of the world.





ALEX BLUMBERG: Right.





JEFF ULLRICH: And when it came time to sell, I had created an environment where I wasn't part of the sale. So the people who bought my company made sure that they told the story that was about the story moving forward. It wasn't about the founder guy who was not gonna stick around.





ALEX BLUMBERG: Right.





JEFF ULLRICH: And so we went from five years of anonymity to this big moment where all of a sudden we were the first major exit in the history of the podcasting industry. And I was responsible for a lot of making that happen, and none of that story got told. And that kind of stuff really bothered me for a very short period of time.





ALEX BLUMBERG: As Jeff got written out of the history of podcasting, it bothered me too. I knew Jeff’s story. I knew how important he was to starting this whole podcasting thing. And I knew how important he was to me, as I was starting Gimlet.





ALEX BLUMBERG: you were doing this for the first time. And you were going through this whole thing by yourself. You didn't have investors. And you didn't have you. Like, I had you. And you had done this all before. so I had you to call all the way through. And that was really meaningful to me. And -- and I just wanted to say publicly, like, thank you very much.





JEFF ULLRICH: Well, you're very kind, Alex. And you always make me feel good and appreciated and a part of things. And I really appreciate that. So ...





ALEX BLUMBERG: I'm not being kind. It's true. It's true. You -- you set a big part of this thing in motion. And I'm sure you're proud of it, but but, you know that, right?





JEFF ULLRICH: I have a really hard time accessing pride. So...





ALEX BLUMBERG: That's probably a good thing.





JEFF ULLRICH: You know, in way I'm like a crazy person, you know? I don't receive compliments or anything that looks or sounds like a compliment very well. And at the same time, I don't want to be forgotten.





ALEX BLUMBERG: It’s taken a while, but what Jeff’s wife Darlene said did in fact happen. Jeff is over his first love. The pain of separation has been replaced by fond memories. And he has moved on. He’s working on something new. It’s a non-profit designed to protect everyone’s access to free and fair elections all over the country. It’s called the Voting Rights Association. And if you’re interested in learning more, you can go to freefairvote.org.





Without Fail is hosted by me and produced by Molly Messick and Rob Szypko. It is edited by me and Devon Taylor.





Music and mixing by Bobby Lord.





If you like Without Fail, make sure to follow us. You can get every episode for free through Spotify, or wherever you get your podcasts. Thanks for listening.



























