Rich Roll’s ‘crash course’ in entrepreneurship

Note: Transcripts are automatically generated from episode audio, and are not fully corrected for spelling, grammar, and formatting.

RICH ROLL: I’m excited to talk to you. I think this is going to be a little bit of a different kind of conversation than I’m used to having. The idea of somebody starting their own business was like a foreign language. It’s been an amazing experience and a crash course in entrepreneurship. To garner people’s attention, you’re best served by trafficking in contrarianism and platforming people with maybe not-so-great ideas. As somebody who is trying to operate from a place of integrity, it creates a conundrum.

JEFF BERMAN: What happened in your life that you found yourself on that farm in Hawaii thinking about putting a first podcast out?

ROLL: A lot happened.

BERMAN: Welcome to Masters of Scale. I’m Jeff Berman, your host, and I am sitting in the Los Angeles area in the iconic studios of the iconic Rich Roll. Rich, welcome to Masters of Scale.

ROLL: Thank you for having me, Jeff. This has been a long time in the making, and I’m excited to talk to you. I think this is going to be a little bit of a different kind of conversation than I’m used to having when I guest on podcasts.

BERMAN: Why is it going to be different?

ROLL: Well, most of my appearances tend to be in the wellness arena, by and large. I mean, it’s called Masters of Scale. It’s a business podcast. It might be the first quote-unquote business podcast that I’ve ever been on, so I’m curious to hear what you’re going to ask me.

Copy LinkFrom hobby podcast to thousand-episode platform

BERMAN: Let’s start with this. When you started, could you have imagined getting to a thousand episodes?

ROLL: No way. When I started, it was late 2012, and I still didn’t know anybody personally, other than myself, who was a listener of podcasts. I would create these playlists because I would go out all day on my bike, and it became like this parasocial friendship that I began to develop with certain podcast hosts. I had been so positively impacted by what I had experienced. Back then, it was a completely different thing. It was almost embarrassing to say you had a podcast. But when I figured out how to get a show up on iTunes and record an episode, I was doing it for fun. My wife and I were living at that time on an organic farm on the north shore of Kauai in the Hawaiian Islands, and I was starting to get island fever, and I wanted a creative project. It was just a fun thing to try, not knowing whether I would ever publish a second episode.

BERMAN: We’re sitting here in a gorgeous studio complex. You’ve got staff, you’ve got infrastructure, and you’re building out a network, which I want to get into. What are the biggest differences between those early days and now for you when you sit in the host chair and engage these conversations?

ROLL: The intention remains the same: sitting across from somebody who inspires me in any number of different ways and trying to engage in a conversation with them where I am creating an environment to get the best out of that person. I’m not a journalist. I’m not here to challenge people necessarily. I’m here to highlight the people that I think are worthy of attention, and that has been, from day one, consistent through all 1,000 episodes. I have a lot of affection for those early days, when the stakes were very low and it could be loose, free, and fun. I am a grateful beneficiary of the fact that this medium has become so mainstream and so popular. Today, because our information and entertainment landscape is so algorithmically driven, if you want to garner people’s attention, you’re best served by trafficking in contrarianism and platforming people with maybe not-so-great ideas and engaging in a lot of drama, a lot of nonsense. As somebody who is trying to operate from a place of integrity, it creates a conundrum. I don’t like that part of it. I still love it, though, and I’m still doing my best to operate from a place of integrity.

BERMAN: How are you balancing maintaining your integrity while differentiating your episode from all the others and not chasing the algorithm and the outrage machine for the clips?

ROLL: I try not to think about the algorithm at all. I know a lot of people who reverse-engineer their podcasts, and their questions are very specific to elicit a response so they can create a clip that will go viral. I don’t think it serves the show or the audience for me to think that way. But that means I have to be at peace with the fact that I’m not creating something that is necessarily going to travel as far as it could if I made those decisions. I think that every host brings something different, and I think my strength is trying to connect with the guest on an emotional level. I do a lot of preparation. I go into every interview very prepared, but like an athlete, you then set the preparation aside, and you have to be present for the experience, because if you’re caught up in your head, then you’re not actually going to be able to perform. So I try to engage it more like a dinner party conversation.

You don’t prepare for a dinner party. I don’t know, maybe some people do. Maybe some people who listen to Masters of Scale think that way. I don’t think that way. I try to be as present as possible, and I have in my mind a direction of where I want to take it and things that I want to know about, but I also have to let go and allow it to be what it wants to be. I’m trying to create an intimate environment where people drop their guard and feel comfortable sharing. I can’t expect them to open up and be vulnerable with me if I am not willing to do that myself, so I try to lead with some of that to create that environment.

Copy LinkWhen a show can change a guest’s life

BERMAN: If we go back, Rich, to somewhere between episodes one and 1,000, was there a moment, like an inflection point, where a guest came on the show and had that transformational experience, able to use it to launch forward, where something clicked for you and you said, “Oh, this is different. This is going to work in a different way than I ever imagined”?

ROLL: Yeah, I never would have imagined that would be a plausible trajectory for anybody, but I’ve had that experience multiple times. I was the first person to have David Goggins on a podcast, and maybe that was the first truly viral experience that I had. It was pretty early on, as I recall. David is somebody that I had known, not directly, but indirectly, because of my involvement in the ultra-endurance community. Everybody in the ultrarunning community knew who David was long before everybody else knew who David was. I’d been chasing him to come on the podcast for quite a while. He wasn’t interested, and then eventually he was, and he happened to be in LA. I went to his hotel, and we sat on the floor of this hotel room — this was before video — and recorded this audio conversation. It went nuts. Not that I’m taking responsibility for his trajectory or his career in any way. He’s a very gifted orator and obviously an extremely inspirational figure. But I’m proud of the fact that I found him first, kind of.

Then there are also people who are complete unknowns. I found a guy called Josh LaJaunie, who was living in the rural bayou of Southern Louisiana with a very heavy Cajun drawl, who had been extremely obese and had come from a community of people that didn’t have a relationship with eating healthy. Beautiful people, but just disconnected from the kind of things that I think about and talk about. He took it upon himself to figure out how to lose the weight, reinvented his life, and became a runner. He’s so endearing, and that episode really made an impact on the audience that then made an impact on him. He would go on to be on the cover of Runner’s World magazine, and he’s done all these cool and interesting things since. Those experiences mean the most to me. I mean, it’s super fun to go to Arnold Schwarzenegger’s office and have him pull out the Excalibur sword. It’s a life highlight. Who gets to do that? But when people ask me, “Who’s your favorite guest?” I don’t really have a good answer.

BERMAN: We were joking before we turned the microphones on. You said perhaps it’s Masters of Modest Scale.

ROLL: Yeah.

Copy LinkWhy build a network without chasing scale

BERMAN: And at the same time, you’ve built quite a show with quite a following and super well monetized, and to your point, the space has evolved dramatically. At the same time, you’re building more. You’re building out a network. Why?

ROLL: Good question. First, I would say that I’ve never considered myself a businessperson or an entrepreneur. I was raised in a very traditional family in Washington, DC. I was raised to be a safety seeker, to pick the traditional career path. The idea of somebody starting their own business was like a foreign language. So foreign that when I went to Stanford, at the beginning of this massive tech boom, I was completely oblivious to what was going on. Everyone was taking computer science classes, and I was reading literature and completely disinterested.

I didn’t set out to be an entrepreneur or a businessperson. The idea for the network grew out of noticing there were a lot of really good voices out there that weren’t operating their podcasts optimally and weren’t being remunerated in a way that I thought was fair. Since I’d been in this for a long time and made all the mistakes and had been at this network for a while and that network for a while, and had bad experiences at all of them, I had decided we were going to be independent. Over many years, we built up a team with infrastructure where we were able to handle brand relationships in a really favorable way. The infrastructure was such that we were in a position to modestly scale it.

I would get calls from podcasters who’d been doing it for a while and had built up significant audiences, but they were baffled about how to monetize their show because the options were either, well, I negotiate my own deals, or I’m going to have to hire somebody and then manage a business. But the podcast is one thing of many that they’re doing. They don’t want to run a small business. So the only option left was to sign up at one of these networks where they’re a line item on a spreadsheet, and they’re going to get lousy CPMs, and they’re going to have to do ad reads for companies they don’t believe in, and they’re not going to have very much agency over the kind of brand landscape that they’re dealing with.

None of those were good options. We’d figured out a different way to go to CMOs directly and work out complex annual deals, and we had been really successful at that. So my idea was, let’s make this available to a few select voices that I think are worthy of this offering because they’re trying to put something out there, and we’re in a position to be able to not only help them but help them get paid what I think they should be getting paid. And that’s how it began, and it’s been an amazing experience and a crash course in entrepreneurship. I still am not involved in the super day-to-day. I’m more like the person who helps find the right podcasters to bring into the network. You’re sitting in this studio that we constructed, a 10,000-square-foot studio. There’s a 60-seat movie theater. We have six studios here, and we work with podcasters who aren’t just in Los Angeles. They’re all over the place. All of our hosts are people who I share a sensibility with. They’re doing something different than me, but I think it’s complementary, and they’re trying to do it against the incentives of the algorithm. We’re trying to find a way to reward them for that rather than punish them for it.

BERMAN: There must be thousands, if not millions, of podcasters who would want to be part of your network. You’ve got 10 or so. How do you decide? How can you tell when someone is not just the right talent, but it’s the right format for the network?

ROLL: I would say we’re still figuring that out. Intuitively, I know if somebody’s going to be a fit. I think it’s about finding the right person who understands the value proposition first and foremost, and those tend to be people who have been podcasting for a while. So they’ve had the negative experiences, or they’ve had the frustrations of trying to do it on their own, and they’re the ones who are so grateful to have the support, and they understand the work behind the scenes that goes into trying to make sure that all of these pieces fit. When you have somebody who’s new, sometimes there are expectations and entitlements that are out of balance with reality. So we’ve had some fits and starts that haven’t worked out, and we’ve learned along the way. We’re not in a hurry. We’re not trying to enlist hundreds of hosts. We’re trying to be very boutique and hands-on right now. But we just made a big hire, and this year we are going to start trying to scale up a little bit more.

Copy LinkRethinking podcast ads as long-term partnerships

BERMAN: It strikes me, listening to you talk about this, Rich, that you’re taking multiple approaches that run very much counter to the moment. You’re not chasing the algorithm. You are really producing with integrity. You’re not chasing scale for the sake of scale. You’re being very intentional about who you bring onto the network and which shows. So much of media broadly and podcasting specifically is driven by CPM, cost per thousand impressions. It’s really transactional, maybe month to month or quarter to quarter. You’re doing yearlong sponsorship deals or multiyear sponsorship deals more in the vein of the NFL or the NBA than how media is typically bought and sold. What is it about you that helps you see how to do things differently from the way the rest of the industry seems to be going?

ROLL: First of all, I want to make sure everybody understands it’s not just me. I have partners in this business who understand business better than me. One of those partners is Jonathan Retseck, who runs RXR Sports in New York City. So Voicing Change Media is basically a joint venture with RXR. I was represented by them as a client, and they would handle my speaking engagements and brand relationships outside of the podcast. Then they took on handling the podcast. So they come from a sports management perspective, not an advertising perspective, and those things are very different.

Together, we have come up with some interesting and innovative ways to work with brands that are very different from the typical way it’s done in podcasting, to your point. CPM, size of audience — like, OK, you have this many people in your audience, that means we’ll give you this CPM, and you’ll get paid that — and it is extremely transactional. You just do the read, and you move on, and you never think about it again. What happens is there often isn’t brand fit with the host, and so a lot of that direct marketing doesn’t work, which means there’s a lot of churn. The advertisers back out, and then the show has to always be onboarding new advertisers because the life cycle is very short.

What we’ve done is much more like how a manager or an agent would think about representation for a professional athlete. Sure, we do some ads where it’s just the ad read. That’s fine. But many of our partnerships are what we call 360 deals, meaning the podcast ad buy is just one portion of a larger deal, more like an ambassador deal. So, for example, I have a few brand partnerships where they agree that they’re going to run this many ads over the course of a year on the show, but also I’m committed to doing this many travel days for them and appearances and speaking engagements and events, et cetera, or photo shoots or whatnot. And those are exclusive categories. So if I’m representing one brand in that category, I can’t do anything with a competitor brand. So it comes with a larger degree of investment of time, but what happens is that you end up with a real relationship that’s meaningful. The audience knows it’s meaningful, and it converts much more significantly for the brand.

Our philosophy and our approach is to always be thinking ahead around what the brand needs. I think there are a lot of creators in the digital space and podcasters who have a sense of entitlement, like, “My audience is this size. You should pay me this much money.” Instead, we’re like, “How can we help this brand?” What is the problem that this brand is having that we can solve? And trying to solve it in advance of them realizing they even have it, because that way you become an indispensable brand partner. There’s no churn, and the relationship is a two-way street. I think too many creators in the digital space don’t respect that or don’t think about that. They’re just thinking about, “What is this brand going to give me?” when it should be the other way around. They should be thinking about how they’re uniquely positioned to serve that brand.

Copy LinkHow addiction and recovery reshaped his path

BERMAN: I appreciate that your legion of fans are probably pretty familiar with your personal story. I’d like to spend a minute on how we ended up here. You and I both went to law school. I’m barely still a lawyer. You’re not practicing. What happened in your life that led you to that farm in Hawaii, thinking about putting a first podcast out?

ROLL: A lot happened. I was raised pretty traditionally in a very education-first, achievement-oriented household, and so I was sort of indoctrinated into this philosophy of life that happiness is a product of climbing the corporate ladder and crafting a safe and secure career for yourself where you were well paid and could be a respected member of society. So I was pretty good at playing that game. But things started to crack pretty early, in that I developed an affinity for alcohol that took me down some dark alleyways. I was essentially a functioning alcoholic for maybe 10 years and a really bad alcoholic for five years. Ultimately, I got sober at 31, but it really broke me. I ended up in a treatment center in Oregon, where I spent 100 days and was introduced to new tools for living. I think that was the first time I began to question what I was doing with my life, because I never really had before. I was just on the track, you know?

BERMAN: How did you end up there? How did you end up in the 100-day rehab?

ROLL: I started drinking in college, and it was a pretty party-permissive environment: work hard, play hard. But from the get-go, it was pretty noticeable that I had a different relationship with alcohol than everyone else. I was the last guy to leave the party. If the keg was tapped out, I was the guy looking for the half-empties. I was the guy who ended up doing something stupid that everyone wanted to joke about the next day. And that’s all fun and games when you’re 21 years old.

Then I moved to New York City, and I was learning how to become a professional alcoholic there, because that is the best place to do that. And I had a great time. I was somebody who was living my life in dissonance with my spirit, but I was unaware of that. I was just going along my way, but something was wrong, and that relationship with alcohol continued to deepen and worsen. The consequences for my behavior started to get more and more significant, to the point where I was living a double life, thinking no one knew what I was doing, but of course they did. I ended up getting in trouble with the law. I ended up having difficulty holding down a job. I got two DUIs in a period of about six or eight weeks. Shortly after I’d moved to Los Angeles, I was facing jail time, and I was on the precipice of getting fired from my law firm job.

My parents finally said, “We can’t talk to you anymore. We’re here for you if and when you’re ready to get help, but you have a big problem, and we’re not available to be codependent in this situation any longer.” I didn’t have one singular rock-bottom moment, but I did have a marriage that went sideways and ended on the honeymoon. I had a series of pretty traumatic events, for me in my privileged life, that ultimately made me realize I can’t keep living this way, but I don’t know how to live. Finally, I was so broken that I was willing to raise my hand and ask for help, and that’s how I ended up in a treatment center.

BERMAN: What happened in the 100 days there?

ROLL: The first thing that happened was that I was honest about what I was doing for the first time with someone else. I started sharing stories and things that I was doing. I remember my counselor pulled me aside and said, “You have a case of alcoholism that we typically only see in veteran drinkers, people who are in their 60s and who’ve been doing this for a long time.” And I was 31 at the time. He said, “People like you die, and if you don’t get it, it’s not going to work out for you.”

I was able to hear that. In my mind, I was doing a spin-dry. This was bad, but I had things to do. I had to get back to my law firm job. But when they said, “You should stick around,” I was like, “I’ll do it. I never want to come back here again. I have an opportunity to completely wipe the slate clean and figure some things out about myself, so I don’t have to come back here again.”

It was the recognition that my best thinking, thinking I’m this smart guy, I got into all these schools, I can do all these things, had landed me in what is ostensibly an asylum for the temporarily insane. That was very humbling. So I got humbled, and I was able not only to ask for help, but to receive it.

Interestingly, as a lawyer, maybe you’ll be interested in this. You might want to cut it out because it’s kind of an aside, but I don’t think I’ve ever told this story on a podcast. Exclusive. First time I’m telling this. Before I went to that treatment center, I had been looking for another job, and I had interviewed at a couple of law firms. Akin Gump was opening an office in Los Angeles, and I interviewed with Akin Gump, and they gave me an offer. Then I went to rehab after they gave me the offer, and I had told them that I was going there.

So I’m in treatment. I’d been there long enough that I had a clear mind, and I said to my counselor, “Listen, I got this problem. I got a job offer from this other law firm, and I told them that I was going. They don’t know that I’m in this treatment center. What should I do?”

BERMAN: Wow.

ROLL: And they said, “Well, you’ve got to call and tell them.” That was terrifying. Of course they’re going to rescind the job offer. So I had the counselor sit with me while I picked up the phone and called them, and I said, “I know you offered me this job, but here’s the situation.”

The guy, a lawyer named David Allen, said, “I’m going to have to get back to you.” I said, “Okay.” They got back to me, and miraculously they were like, “You still have a job here.” And I was like, “Wow, okay.” Then they said, “But we’re assigning you to this partner who’s also in the program.” So I did a call with him, and then they said, “We need you to get working on this case right now. We know you’re in treatment, but we’re going to ship you all these files and documents, and you’ve got to start working. We need you to get going on this.” And my counselor was like, “No way.”

BERMAN: Right. This is not part of the program call.

ROLL: Yeah, this is not going to work. And I had to call them and say, “I’m sorry, but I can’t do that. I’ve got to get this sobriety thing sorted out.” So the job went away then. But it was a sliding-doors moment, you know. I could have ended up as a lawyer. I was in DC recently, and I was riding a bike around, and I rode by that Akin Gump office, and I was like, “Oh my God. I could have been living a completely different life.”

But I was introduced to these new tools for living and these spiritual principles, and I returned to Los Angeles and made sobriety my No. 1 priority. I returned to the law firm where I was working, but really my job was creating a solid foundation of sobriety, and I immersed myself in the recovery community of Los Angeles.

Copy LinkWhy Rich Roll left law behind

BERMAN: I’m struck by how out of integrity you were at the time and how much integrity is central to your life and your work now. How did you continue on the journey to integrity, leave the law, and end up on that organic farm in Hawaii?

ROLL: It took a very long time. I think if you Google me, it might sound like I got sober, then started running ultramarathons, and had a podcast. It was not like that at all. I went back and worked at that law firm. I committed myself to knowing I couldn’t stay there. Emerging from treatment, I knew this law firm life was not for me. I’d been jamming a square peg into a round hole forever. I didn’t even know who I was. I’d just been living my life reactively based upon a program, and I needed to figure out who I was, who I wanted to be, and what was important to me.

These were questions I never asked myself until I got sober. And I didn’t have immediate solutions to those problems, and I needed to pay the bills, so I stayed at this law firm for a while. Ultimately, I left because I just couldn’t even type a confirmation letter anymore. Some might say it was burnout, but I think it was really just, “I’m so out of integrity being here.” Not that there’s anything wrong with being a lawyer in a law firm. It just wasn’t what I was supposed to be doing, and I knew that to my core.

I was on the precipice of turning 40, and I had a health scare. That kind of collided with the existential crisis that I was having, and I had an experience not unlike hitting bottom with alcoholism, where I realized I needed to make some lifestyle changes. That really accelerated the trajectory of rethinking my relationship with career and profession.

BERMAN: As I understand it, you committed to an Ultraman competition before you started training. Do I have that right?

ROLL: Not quite that.

BERMAN: Okay.

ROLL: I had started exercising again because I changed my diet, and I felt revitalized. I’d basically been eating fast food and Chinese food at the law firm and had gained a bunch of weight. I started taking care of myself, and I had this resurgence of energy. I went back to the pool, and my wife got me a bike for my birthday, and I started doing a little bit of running. I’m 40 now, so what do you do when you’re 40? You’re like, “I’m going to do an Ironman.” This is the most trite, clichéd thing possible.

But I was enjoying feeling connected to my body again. I had been a swimmer at Stanford. I’m a lifelong athlete, and I had really disconnected from that part of myself. So I was recapturing that just for the joy of it. But then I was like, “Oh, I like this. Maybe I will do an Ironman.” I’d done a little short race here and there. I didn’t realize all the Ironmans sell out a year in advance, and I came across an article about this race called Ultraman, which is a double Ironman, a three-day race. Something about it spoke to me. It felt more like a spiritual odyssey than a competition, and really that’s what I was on.

I was on a spiritual odyssey, seeking answers. I was asking myself questions that I didn’t have answers to yet. Training for endurance events really was a way of processing all of that, and this race represented a way of going deeper into that exploration. So yeah, I signed up for Ultraman before. I know, and to this day I’ve never done an Ironman. I just went right to the super-long stuff.

Copy LinkWhat it takes to stay in integrity

BERMAN: Curious, Rich, as you sit here 15 or so years into this podcast journey and building this business, and showing up in the world as you do for so many people, how do you stay in integrity?

ROLL: It’s a lot of work.

BERMAN: It’s a lot of work.

ROLL: It doesn’t come naturally. I learned early in recovery there’s an aphorism in AA: You can’t transmit something you haven’t got. And I think about that a lot. There are a lot of people pontificating on the internet. They’re trying to transmit something they don’t actually have, and that’s why it falls flat. Because the resonance of your voice is a function of how fully you’re living it yourself.

Integrity for me means that I’m living my life in alignment mentally, spiritually, physically, and interpersonally. How are my relationships? How am I feeling about the decisions that I’m making? Am I taking care of myself? Am I taking care of the people I care about? Integrity is multifaceted. And I think on any given day, I’m probably out of integrity in some way. You can’t be in perfect integrity or alignment with everything simultaneously. But from a global perspective, are you in the right place doing what you’re supposed to be doing? That’s really a function of your relationship with your intuition.

I think a lot of people mistake what they want to do for their intuition because they’re not integrated. They’re too disconnected from one aspect of themselves, either their body or their mind or their spirit, to differentiate what they want from what their intuition, their heart intelligence, is telling them. And that connection doesn’t always come naturally, and the modern world is always trying to distract us from it or erode it or incentivize us to act in opposition to it. So it’s something you’re always toggling, I suppose. But it’s important to me.

I think there are a lot of charlatans out there who are very much out of alignment, and they have large profiles and wield a tremendous amount of influence. But I believe in people, and I think people’s antennas are getting more and more finely honed to who’s worthy of their attention and who isn’t. As we mature into this complex media environment that we all live in, there’s a need for people you can trust, people who are operating from a place of integrity, who might not be the biggest, but are the people that, when you really want to know what to pay attention to, what not to pay attention to, who’s telling you the truth and who isn’t, become very valuable.

That’s something I’m always thinking about. To me, that’s the ultimate commodity, and it can be so easily squandered. I think people trade their trust and their integrity for pennies on the dollar all the time, and I don’t understand it. I play the long game, and that means maybe you’re not the shiniest object. But over the long haul, I know that when I’m scrolling online, I’m looking for the person I can trust, even if my dopamine is getting hijacked by somebody I don’t trust.

BERMAN: What a perfect place to wrap, Rich.

Thanks for being on Masters of Scale.

ROLL: Thank you. Appreciate it.