Years ago, Rich Roll hit rock bottom. Now, he's the voice of one of the most popular podcasts out there.
Years ago, Rich Roll hit rock bottom. Now, he's the voice of one of the most popular podcasts out there. (Photo: Beau Grealy)

Rich Roll Is the Oprah of Endurance Sports

Years ago, Rich Roll hit rock bottom. Now, he's the voice of one of the most popular podcasts out there.

As host of one of the most popular interview shows in the podcast universe, Rich Roll is known for his limitless empathy. That approach grew out of his long personal journey. A talented college swimmer, he developed an alcohol problem that later destroyed his first marriage and nearly derailed his career as a lawyer. He sobered up but became a miserable workaholic, until, at age 40, he went vegan and started endurance training. Soon he was a top finisher at the Ultraman, an infamous sufferfest in Hawaii. On his weekly show, Roll interviews everyone from elite athletes to spiritual leaders to bestselling authors, all in the interest of empowering the rest of us to make better decisions. In this episode, he shares his inspiring story and the many hard lessons learned.

Podcast Transcript

Editor’s Note: Transcriptions of episodes of the Outside Podcast are created with a mix of speech recognition software and human transcribers, and may contain some grammatical errors or slight deviations from the audio.




Outside Podcast Theme: From Outside Magazine and PRX, this is the Outside Podcast.

Michael Roberts (Host): Hey everyone, before we get started, I wanted to tell you about something on the horizon in 2020. For the second year in a row, we're hosting the Outside Experience, a curated weekend of adventure and inspiration. This time it will be on Chicago's Northerly Island, a park right on the shores of Lake Michigan. We'll have all the latest gear to check out, guided experiences, like rock climbing and group runs, a beach cleanup, craft beer, and even a podcast summit with hosts from some of our favorite shows . Whether you're a seasoned adventurer or just looking to try something new, mark your calendar for May 16 and 17 to join us in Chicago. It's going to be a great weekend.

[Music under intro]

Roberts: Just relax.

That is the big idea behind Outside Magazine’s current issue. And, to be honest, it’s the kind of improve-your-health message we tend to deliver every January. Just like a lot of other media outlets. At the start of the new year, people are looking for guidance on how to meet their lofty resolutions. We’re happy to deliver. Hey, we need it, too.

But while many past January issues have focused on fitness and athletic performance, this year we really wanted to help our readers chill out. Our goal was to provide remedies for the frenetic, angst-ridden state of being that we all seem to be experiencing these days. It seems that everyone is constantly overworked. We’re also bombarded by terrifying news about the climate. We’re pickled in angry politics.

We respond by rebooting our nutrition, ramping up our workouts, hacking our time to supercharge our productivity. And it’s not helping.

With that in mind, we wanted to create an issue offering alternative strategies that point in the opposite direction: away from all the striving, and towards relaxing.

From the moment we settled on this plan, we knew who we wanted to put on the cover: Rich Roll, the massively popular podcast host and vegan athlete who is an icon for radical life transformation. Here’s someone who has faced addition. Who boldly abandoned his career as a lawyer to chase his passion for endurance sports. Who found a purpose in his recovery. On his weekly show, Roll interview everyone from elite athletes to spiritual leaders to bestselling authors, all in the interest of humbly empowering the rest of us to make better decisions. The entrepreneur and life coach Jesse Itzler aptly said that Roll is “like the endurance-athlete version of Oprah”.

And so we sent frequent Outside contributor Peter Vigneron to Southern California to spend some time with Roll. he started by attending a live edition of the Rich Roll podcast, held in LA’s Wilshire Ebell Theatre, where Roll interviewed the environmentalist Paul Hawken. The most memorable moment of that evening actually came in Roll’s introduction, when he threw out a planned speech and instead read an email he’d gotten from one of his listeners:

[Cut to live tape from Rich Roll’s LA show]

Rich Roll: ...And I thought that it would be good to read this one, because the person who sent it to me happens to be here this evening. So bear with me. This is from Ron. Ron writes: Hi, Rich. I’m headed to LA tomorrow to join you for the live podcast event, and very excited for the experience. We met at the Conscious Capitalism CEO Summit coming on two years ago. We had lunch with a small group, and I shared with you afterwards that my sixteen-year-old son was in treatment for drug and alcohol addition. You said the greatest thing to me, and that was, “Wow. What I would have been able to have done with my life if I learned the recovery skills at sixteen versus forty.”’ Rough forty—it was actually thirty-one, but…  ‘And that comment gave me hope. I also started listening to your podcast on a regular basis, and it has been a part of my journey to be a better father, husband, and leader. I get to share that through my involvement as the founder and Board Chair of Conscious Capitalism, Kansas City, so thank you. Jumping back to this week, my son will actually be in the audience with me. He is now eighteen. He has been accepted to LMU in Los Angeles for fall of 2020. He is at LMU this week taking part in the dedication of their new Ions for Recovery Center in the student union and speaking on a panel sharing his story.

Right? And this is the part that got me.

So you were right. And I learned that recovery gives expansion and not contraction. Recovery gives expansion and not contraction. I appreciate you for being a light and inspiration for us to live better lives and create a better world with gratitude.

Ron? Ron Hill? Are you here? Can you stand up and wave? And your son, Alec. I can’t see the crowd but there you are. Beautiful.

[End tape of Rich Roll’s show]

Roberts: Two days after that event, Vigneron went to Roll’s home in the Santa Monica Mountains, where he lives with his wife, the vegan-cookbook author Julie Piett, and the youngest two of their four children. They sat down in Roll’s home recording studio to talk about his long journey.

He’d grown up in a suburb of Washington, D.C., where he attended an all-boys prep-school. He was extremely hard-working: a strong student and a top swimmer. He wasn’t the kind of kid who got into trouble. That changed, though, when he started getting recruited by college swim teams.

Roll: Part of the whole, like, recruiting trip thing, is you party. Right? And like, I hadn’t really been to parties in my life, but here I am, uh, going to house parties and going to bars and all that stuff. And that was really kind of my first real introduction to alcohol. And there was this one time: I was recruited to the University of Michigan. The coach at the time was John Ubanchek. Still my favorite coach. He's like the most amazing swim coach in the world. And Michigan was very much on the rise, and I have a personal family connection to the University of Michigan. My mom went to the University of Michigan, and my dad went to law school at the University of Michigan. Everybody in my family and extended family is from Michigan. They're all, they all bleed maize and blue. And my grandfather, who died before I was born, was captain of the University of Michigan swim team. I believe in 1928. If I’m not mistaken. He held an American record in the 150-meter-backstroke or yard backstroke, which is not an event anymore, but it was at the time, and an Olympic hopeful. He barely missed a birth. You know, he was like a peer of Johnny Weissmuller in that era of swimming. So this is the legacy with which I go on this recruiting trip to the University of Michigan.

And there was a dual meet that weekend, which I was able to watch. And then, following that, there was a house party. So I'm at this house party with all the swimmers, and there's a keg and it's a good time, you know, happening. And I remember being given a Big Gulp thing of beer to drink and drinking it. I've got this buzz on.

And one of the divers, Bruce Kimball, who was the second most famous diver in the world at that time behind Greg Louganis... whose father was the diving coach at the University of Michigan--Dick Kimball, legendary diving coach—Bruce also liked to party. And he pulled off, right in front of me, the greatest party trick I have ever seen to date.

Which is, he was holding a cup of beer—keg beer—and from being flat-footed, he jumped in the air and did a backflip holding this cup of beer. And landed. And did not spill one drop of this beer. And I just… my mind was blown. I could not believe it. And I just thought, ‘Whatever that guy has, I want it.’ I was all in. I was like, ‘If that guy can party like that, and do what he's done, I want to be a part of this community.’

It was almost like this permission to drink, in a way that I felt prior to that was not okay. Suddenly it felt like it was okay. Like this is... yeah. Like, look at this guy and what he's done with his life. Now, for those that don't know, fast-forward to what you know happened in the not-too-distant future of Bruce Kimball, which was that he, um, he was drunk. And he plowed into, I believe... I don't want to get this wrong, I may have this a little bit wrong... but I believe he plowed into a group of people drunk driving. Killed somebody. Went to prison. Basically, he was an alcoholic who suffered very dire consequences as a result of being an alcoholic. So what I thought was cool ultimately turned out to be something very dark. And I had to experience my own version of that later on.

Roberts: But Rich didn’t go to Michigan. He chose Stanford, which was another powerhouse for swimmers. It was a big change for a kid from the east coast, and Rich made the swim team as a walk-on.

Roll: I arrived on that campus and just fell in love with everything about it. It was so different from growing up in Washington, and there was an openness to it, and it seemed like everybody that I've met had something unique and cool about them. It was just such an incredibly dynamic and supportive environment. And I thrived in it. You know, I felt like I could be myself.

I was doing well academically, and I showed up ready to go. Like, I showed up in shape for swimming, because I realized I'm walking onto this team, and I'm going to be training with Pablo Miralis and John Moffett and Jeff Kostoff. I mean, these were the absolute legends of the time. And if I expect to be of any value to this team, I've got to earn my spot and I can't mess around. So my first meet, it was against Texas.

We were number one, they were number two. Uh, and I almost won the 200 butterfly in my very first dual meet against Billy Stapleton, who would kind of famously go on to be Lance Armstrong's agent. It was a very positive, auspicious start for this young walk-on freshmen. Who by the way had suffered a cracked rib like the week before, because I was drunk at a football game. So the cracks in the… it was a foreshadowing of what would soon, you know, come to pass.

Roberts: By the spring of his freshman year, Rich was drinking four of five nights a week. But he didn’t think he had a problem: this was college, and he felt like he was just having fun. Still, he did start to notice that when everyone would be heading home, he was the guy staying out.

Over time, he says the drinking eroded his ambition and his self confidence. His swimming career peaked when he was a freshman. He got slower the next year, and in the spring of his junior year, he quit the team.

After that, Rich says he wandered pretty much aimlessly for a long time. He graduated Stanford, and he went to law school, mostly because he didn’t know what else to do. He even got engaged, but the marriage ended during the honeymoon: a huge sign that something was very wrong with his life.

Around the same time, he had moved to Los Angeles to work for an entertainment law firm, and proceeded to get arrested twice in two months for drunk driving. The second time proved to be an important turning point.

Roll: So the second DUI that I got, I got pulled over. It was like two or three in the morning. Driving the wrong way down a one-way street in Beverly Hills. Get pulled over. Blood alcohol tested. .27, I think. Arresting officer confiscates my wallet, sees my business card in my wallet. Realizes that he knows my boss. Calls my boss, who is a prominent litigator in Los Angeles who had done a lot of work for the LAPD and the Beverly Hills police department over the years. Says I picked up one of your boys. So Monday morning, I'm, you know, I go to jail for the night, but I get outta jail. And I'm just going to show up at work. Pretend like nothing happened. [Laughs] You know, even though my license has been suspended, this is two DUIs in a row. Like, I'm living in a dreamland. ‘Cause basically I'm going to jail, and I'm pretending like everything's fine.

Boss calls me in. Says, I got an interesting phone call over the weekend. Like, I don't want to get involved in your personal life, but it sounds like, you know, your shit's upside down dude. Like, and I can't have that. We were preparing for a trial at the time, where I was going to second chair this trial. It was a very intense work period. So he's like, I need you to call this lawyer. This is going to be your guy. And, you know, just solve it. Like, I don't want to hear about it.

Of course, this lawyer was extremely expensive. He's like, you know, high powered. You know, a criminal lawyer in Los Angeles. His name is Charlie. And Charlie just gave it to me straight. He's like: You're a drunk. You're going to jail. You know, I'm not a miracle worker here.

Like, you know, look at this on paper, like, this is what you've given me to work with? Like, you're going to go to jail, dude. And that really scared me. Really, really scared me. Because it was like the veneers of denial were starting to, you know, fall away. And I was starting to get a picture of the truth of how I was living. And then, this really remarkable thing happened. Which is, the file—the court file for my first DUI—got lost. And I was never prosecuted for that.

So that just disappeared and went away out of the blue. Charlie's like, ‘You don't understand, I've been practicing law for forty years. I've never seen that happen once.’ So I go to court for the second one, and I get probation, and basically, you know, my license is stripped, you know, I've got--there's things I have to do, and I've got to go to, you know, AA, and get court [inaudible] and all that. But like, I didn't have to go to jail.

It was this gift that should never have happened. And that's when I realized like, you know, I'm being looked out for. Like something else is going on. Because that doesn't make any sense whatsoever.

Now, that doesn't mean that I was struck sober and never drank again. Like I had a very inelegant, you know, nonlinear relationship with recovery for a period of months after that. But ultimately, you know, I reached that point that you hear with other people in recovery that, that, that point of no return where you wake up and you finally have the willingness to do whatever it takes. And, and that's when I ended up in a rehab in Oregon.

Roberts: Roll was thirty-one years old when he went to rehab. Initially, he expected to stay at the center for just a couple weeks. That’s not what happened.

Roll: And when I got there, I just realized, like… when the fog started to clear, I just realized the gravity of my situation and how, how horribly wrong, you know, I had, I had gone. And I never wanted to be in this place again. And I really developed the willingness to just do whatever it was going to take to create a foundation of sobriety so that I could, you know, basically reinvent myself.

When I started telling the truth and being honest about how I was actually living, they were like, you have a case of alcoholism we typically only see in lifelong drinkers, like 65-year-old dudes. And you know, if you don't figure this out, you're gonna die. You know, it's like this is not a joke. And we think, we know you want to get back into the world and blah, blah, blah. And it's your choice, but we really think you should stay longer. And I just said, I'll stay as long as you think I should. And I ended up staying a hundred days.

[music begins]

Roberts: Roll describes his early years of recovery like a mission to fix everything he had broken while he’d been drinking. He went about this with a lot of intensity. But he also ignored other key aspects of a healthy and fulfilling life.

Roll: And when I got sober, my goal was to repair all the wreckage that I created as a result of my drinking and using. Like, I had... the fall from grace was so precipitous. Like I had been this person with all this potential and I squandered it. And there was so much shame about that. And I was like, I really was intent upon becoming a productive member of society. You know, somebody who, who could earn another person's respect and who could show up on time and like do all this stuff. And that involved repairing the relationship with my family and with friends and all of that. And, you know, I was very dedicated to that, and I was successful in that. So between thirty one and thirty nine, I had bridged that gap. And you know, successful as a lawyer, you know, in good with my friends and family again. Uh, and kind of had gotten all the stuff, like I was driving a sports car and like, you know, building this house and it just all looked really groovy.

But what I hadn't done was enough of the inside work to come to terms with the fact that I was chasing somebody else's life. Even though in rehab I was introduced to these spiritual principles about how to live, and I had grabbed onto those and had made progress, I had figured out a way to no longer use drugs and alcohol and to kind of expand my horizons on the possibilities for my life. I was still very much, you know, in the amateur leagues of understanding how to apply those principles to my life and in a fundamental and tactile way. And I was pursuing this career out of ego and fear and insecurity, not because it was my passion for what I wanted my life to look like. And so what happened was the pain of that experience caught up to me in the same way that the pain of my drinking and using ultimately did.

And it culminated in this evening, shortly before my fortieth birthday, when I was walking up a simple flight of stairs after a long day of work and had tightness in my chest and was out of breath. Like I couldn't walk up a simple flight of stairs without taking a break.

And that realization, like, that was another breaking of the denial  I still thought of myself as the Stanford swimmer, but I was carrying around fifty pounds extra around the midsection. You know, I didn't really look in the—you know—if I was honest with myself, I was so far away from that human being because during this, that, that eight, nine year period, I was like a workaholic.

Like I wasn't, I was eating, you know, I was just a junk food junkie and take out food in the law firm and not exercising and just working this seventy, eighty hour weeks and all that kind of stuff in pursuit of this other person's life. And so the existential crisis kind of collided with this realization about my poor health. And that was the perfect brew. Like, you know, this collision of ingredients that created this second moment of reckoning.

And I think, because I had experienced that, um, by, by going to rehab and realizing how much my life had changed by making one simple decision, I had enough self awareness to realize, you know, on that staircase, that I was being revisited by very opportunity. And that if I grabbed onto it, perhaps I could make another, you know, big change. Like, this is another bottom, but it's also another opportunity. And, and I did that. And that's really kind of what set in motion, everything that's followed.

[Music gets louder]

Roberts: We’ll be right back.


Roberts: The first big change Roll made after his second moment of reckoning was to overhaul his diet. With the enthusiastic support of his wife, Julie Piatt, who he’d married just a couple years into his recovery, he became a vegan.

He also began exercising again: swimming and running. It wasn’t anything crazy—at least not at first. But he was reclaiming his fitness quickly and feeling good. Soon, he was running five or six miles at a time. And then, very unexpectedly, on what was supposed to be another routine run, he just… kept going.

Roll: …On these trails, and I was just going to run for forty-five minutes, or an hour, and I just... I had one of those moments that every runner is familiar with, where you kind of drop into this flow state and you feel bulletproof and like you can run forever, and you know, each mile you feel stronger than the one before. And I'd never experienced that before. Um, and just decided to go with it, and ultimately ended up writing like 24 miles and you know, four hours of [inaudible]. The trail is like the craziest thing. Like, the last thing I thought would happen, and, and another, you know, kind of moment of... you know, realizing that maybe my life could look differently. Like either these lifestyle changes I've made are more profound than I anticipated or—and, or—I've unlocked this potential or this gene that was dormant, or that I didn't even know that I had. And if my journey has been about anything, it's about trusting those whispers and, and being willing to have faith and invest in those little signals that are just so faint and yet potentially life altering and meaningful.

Roberts: The whispers in this case were clearly telling him to start training harder, and with more focus… which he did. He also signed up for his first triathlon… it didn’t go so well. He started throwing up during the swim and wasn’t able to finish. And yet… he enjoyed it. So he hired a coach and began hunting around for another event to enter. He wanted something really, really hard.

What he found was Ultra Man, which is essentially a double-length Iron Man around the big island of Hawaii.

Roll: ...This race that very few people know about that had been around for a very long time. And it was really more of a spiritual Odyssey than an athletic event. Every year, Jane Bakos, the director of this race, would handpick 35 people from all over the world to participate. Not necessarily the best athletes, but people she felt like could benefit the most from having this kind of experience. It's a self-supported race. You bring your own crew over this three-day period. You circumnavigate this entire island. It's a race, and it's a world championship, and there are athletes that are vying for that title. But ultimately the greater goal is that every single person—athlete and crew member—be transformed as a result of going on this collective three-day caravan. And that really connected with me. And I was like, that's what I'm looking for.

Like, that is the experience that I'm missing in my life. And I want to feel like, what would I want to, I want to feel what it would feel like to embark upon something so difficult. Like it bent my mind that people could actually do this double Iron Man thing. It was insane. But once I got comfortable with that, it was like, this is not about a race. This is about broadening your perspective on who you are, and connecting with yourself in a really profound way.

Roberts: Before he could compete, Roll ahd to get accepted into the event. His only credential was… not finishing a much shorter triathlon. But he called the Ultra Man Race Directory anyway, and told her his story. She didn’t say no. Though she didn’t say yes, either. She said maybe. WHich was all the encouragement Roll needed.

So he had a coach, a training plan, and a goal. His biggest challenge? Roll was still a lawyer.

Roll: Um, I’m working, trying to make a living, training for this race, and now, this is… Now, the idea of like the digital nomad is so widely accepted. Um, but this was a period of time where the internet was still pretty new, like, using it for much else other than email was not really that functional. Um, so the notion that this lawyer is going to have to pull over off his bike and handle a conference call, like, in the middle of the day, you know, you're thinking like, everybody's in suits and their offices. Like, if they could see me now. And I'm trying to play it off like I'm in an office… it was a shell game for a while. You know, I was living this double life. Like I was pursuing this one area, but also trying to hold myself out as this, like, person who's in the office all day long.

...Have all my stuff in my truck and you know, I would, I would just go wash myself off and in gas station bathrooms and you know, have changes of clothes, and have all my training gear with me. So I literally was like camping sort of all the time.

Roberts: Roll was eventually accepted into the 2008 Ultra Man, and he stunned everyone at the event, including himself, by finishing in 11th place overall… and third among Americans.

Convinced he could do even better, he signed up again in 2009.

But while out on a training ride on his bike in the Southern California hills that spring, he crashed. Badly. Smashing his head and face so hard that even today, he can’t feel his lower lip. He still has scars on his face. Roll doesn’t remember much from the accident, but he does recall being in the emergency room with his wife and wondering if he should quit.

[Music begins]

Roll: That really made me question the wisdom in what I was doing. Like, I've got kids. I'm a lawyer. Like, what are you doing, man? You know, like crack your head wide open, for what? you know, and you know, it was, uh, it was, uh, it was a moment in which I really had to get clear on truly what it was that I wanted to do. And Julie said to me, as I was laying in that bed: ‘If this was it, and it was all done, like, would you do it again? Is this—do you regret it? Like, what do you want your life to be?’ And I was like, I know this is what I want to do. She's like, good. Then do it. It wasn't that I had answered all the questions that I had for myself, but I felt like my compass was being calibrated somehow. Not in the sense that this was going to be a vocation, but, but there was something about what I was trying to do and what I was pursuing that just felt in alignment. Like I felt like this is the direction I need to go in and I have, I can't see past two weeks from now in terms of where this is going to lead me. I just feel convicted that, that the answers that I seek are going to be discovered and revealed by continuing to pull on this thread rather than reverting back to what I know.

Roberts: In his next Ultra Man, Roll finished the first day leading the field by ten minutes. Then, on day two, he crashed his bike again and lost any chance at a podium finish. He struggled on through a lot of pain, and he ended up finishing sixth, beating his time from the year before by two hours.

Roll:  And that was incredible because… the challenge of crashing and having to pick yourself back up is really what reveals character. Like, that's the test. Executing a race at the highest level and having everything go your way isn't exactly the learning experience that I was looking for, that I needed. To me, it was a perfect race, because I had crashed, I didn't want to finish the race, and my ego was shattered and all of that. And I still had to pick it up and finish it. And like I learned more about myself as a result of that than I ever could if everything had gone my way. So, you know, I love everything about how that ended up. Uh, but it still left me thinking, like, I have capacities that I didn't realize that I had.

Roberts: Pushing the limits of those capacities led Roll to partner with endurance athlete Jason Lester to take on something they dubbed the “Epic Five.” It had them doing five Iron Mans on five Hawaiian islands in under a week.

It was another inspiring, life-changing experience. Meanwhile, though, real life matters--things like the responsibilities of earning money and taking care of your home and your family--they were becoming increasingly difficult to manage at the same time. The only reason Roll was able to do it, he says, was because of the strength and dedication of his wife. Even during later years, when they were on the verge of losing everything, Julie’s faith in what they were doing never faltered.

Roll: We went through, uh, an extended dark night of the soul. Julie calls it our, uh, our dismantling. We went through many years of not being able to pay our mortgage. We had our trash bans taken away because I couldn't pay the sixty bucks, or eighty bucks, or whatever it was. Just putting food on the table was a struggle. Uh, we had cars repossessed. It was really challenging, and really humiliating, and there were plenty of times where I thought I was insane. How could I, you know, like, I was this person who was in this place and now I've gone through all of this and now here I am and this is what we're dealing with? Like, I must really be insane. Or what is fundamentally wrong with me? And Julie would be like, no, everything is the way it's supposed to be. And we are, we are burning in the fires because we're being prepared for something else. And I was like, you're insane.

I'm very rational, and she has shown me time and time again the limits of that operating system and the expansiveness that can be experienced when you let go of that and allow yourself to live more in integrity with your inspiration and your intuition, which is a very difficult, delicate, ephemeral thing to do. But I really do have to see, like, I would not be doing any of these things if left to my own devices. And it was really her strength that that gave me the permission to continue to move in this direction.

Roberts: From alcoholic, workaholic, to plant-powered endurance hero who’s willing to risk it all to pursue an enlightened path. It sounds like a helluva book. Which it was. Roll published Finding Ultra in the spring of 2012.

The thing is, though, the book wasn’t actually his idea. It came from another former swimmer at Stanford who was early in his own addiction recovery when he read a short blurb about Roll in the alumni magazine. He reached out to Roll because he was looking for people to talk to. People who would understand him.

They had regular conversations for months, until, at one point, the guy says: Hey, your story is amazing. You should write a book. As it happened, this person also knew the agent of Dean Karnazes, the superstar ultrarunner whose book about his transformation had been a break-out hit.

It sounds like another lucky moment in the saga of Rich Roll. But as he sees it, it’s also a result of his enduring commitment to addiction recovery.

Roll: And I look at it as... a function of putting sobriety first. You know, like, my only goal was to be of service to this person who was newly sober, you know, and everything good in my life has come as an outgrowth of putting service first, and recovery first, and just letting, like sort of allowing whatever else is going to come, come.

Roberts: Roll also credits recovery for teaching him how to understand and tell his own story—and to listen and interpret other people’s stories. These are valuable skills when you’re writing a memoir… or when you go on to create a podcast.

Roll: What you learn in the secret society rooms of recovery that we're not allowed to talk about, uh, you develop a huge capacity for empathy, and you learn how to be vulnerable. You learn how to tell the truth and you learn to listen. And you get practiced in telling your story. You sit, and you listen to other people share their story, and you learn from their courage and their vulnerability, and their emotional journey. And then it's your turn to go do that. And over the years you get better and the story starts to teach you what's important about it. Um, and what is that impactful and helpful to other people. So, I learned how to share my story in those rooms. I learned to be vulnerable. I learned to, uh, be comfortable expressing my truth and my emotions and my weaknesses and failures and the like. All of that comes from recovery. And I think it's interesting that a lot of successful podcast hosts are in recovery. That's not a mistake. Because you learn the craft of storytelling, and you learn how to emotionally connect with other people. And, um, and I think that's... that's how I learned how to get up in front of people on stage and how I learned to be a good host, and learn how to be a good listener when I have guests.

Roberts: On the day Finding Ultra came out, Roll ceremoniously did not renew his bar membership. He was done being a lawyer, and all in on this new life of pursuing his passion. It wasn’t as glorious as you might think.

Roll: Hence ushered in a very long, extended period of time in which the phone did not ring. Which ushered in a financial hardship for many years. A lot of uncertainty about what life would look like, and doubt. And it made me think... I'm just full of shit. Like, I just wrote this book, and I talk about all these spiritual principles, and how you have to do the inside work, and trust your heart, and follow that, and all of that. And I'm like, you are so full of shit, man. Look at your life. It's a disaster right now. You're not an example for anything.

We were on the precipice of losing our house. Like, you know, the material world was kind of collapsing on top of me. And there's this narrative out in the world, or on the internet, like, oh, Rich writes this book, and starts this thing, and it's all gravy. And like, oh, it was a New York Times best seller. It was not a New York times bestseller. It did okay. And it found a little audience. But it wasn't like this book that then just captured the fascination of the world. It wasn't like that at all.

Roberts: Roll was thrown a lifeline by a wealthy friend, who invited him and his family to stay on a property he owned in Hawaii, where he was establishing an organic farm. The friend asked Roll to help him develop some community pieces for the project.

They lived in yurts. It was an adventure of sorts, but one that soon gave Roll a case of island fever. In the wake of the book, he was eager to figure out his next thing—and hungry for another creative outlet.

During his long hours of endurance training, Roll had listened to hours upon hours of podcasts, and fallen in love with the medium. Now, he thought: Maybe I could do something.

Roll: And when I looked at the hellspace, there was some interesting stuff, but I felt like there was a lot of opportunity there. Because there just wasn’t that much. You know. And, we were in Kuai, we were with my sons, who had all this musical equipment and microphones. I spent a day going online trying to figure out how you start a podcast. And once I solved that, I just turned the microphone on and my wife and I started talking. And that was it, you know? And it was fun. I thought, let's do that again tomorrow.

Roberts: From the outset, Roll knew what kind of show he wanted to create. It would be one focused on his guests, not himself. Also: he didn’t want to host a podcast that was only for athletes.

Roll: I was very clear from episode one, like, this is not going to be about me, and it's not going to be about triathlon. You know, this is not going to be a training podcast. Like, I've grown to a certain point, and there's so much growth to be had. I want to continue to grow. And I want to bring on people who can help do that, that I can do that with, who can teach me. And who are those people? And how can I create what I would have liked to have discovered 10, 15 years earlier, when I was trying to figure out who I wanted to be. And I felt like I couldn't be anything other than what other people's expectations for me were. What if I could create a curriculum that could empower people to make better decisions about the trajectory of their lives? And that was really the kind of subtext or philosophy that has, you know, kind of empowered the whole thing.

Roberts: Another one of his guiding principles is to avoid labels. Roll isn’t totally comfortable with the idea that he’s part of the wellness or self-help industries. He says he’s really just following his curiosity. His hope is to share conversations that help people to make real, lasting changes.

Roll: I'm trying to, I'm trying to catalyze people into action, right? And I think there is... there is something to be said for people that read lots of self help books and think that they're changing their lives. But they're not actually implementing any of that advice. They're just reading it, and then they have a self awareness like, Oh, this person said this. Isn't that amazing? And it's like they're just, they're not making any changes in how they're living. So, um, I am aware of that, but I'm constantly talking about action. You know, what are the actions that you're taking? It's not how you feel about things. It's not, you know, the idea that you have about them. It's like, it all boils down to like, what are you doing?

Roberts: After launching his podcast, Rich Roll didn’t take a break for seven years. Every week, he faithfully uploaded a new episode. As someone who works in podcasting, I can tell you: that is insane. Roll finally recognized this, which is why he just took a month off. He unplugged for all of December, though he did pre-record a number of episodes beforehand, so his podcast kept rolling while he was gone.

Roll: I think for many years I've been burning on... I've been sort of fueled by this unsustainable fuel source of, of like fear and desperation. Because... because, you know, that dark night of the soul and that dismantling, was so, um, traumatic. Yeah, traumatic. It left me with a PTSD. And now, like, everything's working. And, and like, it's all awesome. Um, but I feel like I've got to double down. I've gotta work hard. I worked hard cause like it was so hard before that I just don't want to miss this opportunity.

And it's taken me a while to realize that like, I don't have to burn so hot, you know, like I have done. And that if I want to keep doing this, I really need to take a break. And I, I haven't taken a vacation in seven years. And I feel like I really need to do that. So I'm going to go completely off radar for an entire month so that I can come back in the new year.

[Music gets louder]

Roberts: That was Rich Roll. He shared his story with Outside’s Peter Vigneron.

This episode was produced by me, Michael Roberts, with music by Robbie Carver.

It was brought to you by LL Bean, maker of industry-leading down-tech jackets that will keep you warm and dry for hours during a perfect winter day outdoors. Find all their innovative outerwear at LL Bean: Be an outsider.

We’ll be back next week, with an episode about people chasing the Aurora Borealis.

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Outside’s longstanding literary storytelling tradition comes to life in audio with features that will both entertain and inform listeners. We launched in March 2016 with our first series, Science of Survival, and have since expanded our show to offer a range of story formats, including reports from our correspondents in the field and interviews with the biggest figures in sports, adventure, and the outdoors.