From Prison Guard to Endurance Star: Ken Rideout on Mindset, Non-Negotiables & Self-Accountability

The heart and soul of this podcast is personal transformation—and today’s story of metamorphosis is one of the most compelling, improbable, and inspirational tales I have ever heard. Narrating this epic saga is Ken Rideout, a guy who has transcended a litany of seemingly insurmountable obstacles to become one of the world’s pre-eminent master athletes. Now 51, he smokes his running competitors like a bad habit—and is only beginning to hit his stride. It’s a land mine littered path that didn’t come easy. A rough and chaotic childhood, a battle with addiction, learning harsh truths as a prison guard right out of high school, and later losing colleagues on 9/11 are just a few of the many obstacles he’s faced and overcome. Nonetheless, and without any formal experience, he somehow made it to Wall Street and beyond—and has been stacking goals ever since. Ken’s latest goal? To be crowned masters champion in all the world’s most prestigious marathons. Crowned “World’s Best Marathoner Over 50” by the New York Times (in an article written by friend of the podcast Matt Futterman), it’s fair to say this former boxer is already well on his way to achieving that goal. Today we walk through Ken’s journey, covering his early years reared in chaos, his time spent as a prison guard, and how he hustled his way against all odds to get to Wall Street. We also dive into the opioid addiction that nearly cratered his life, his mid-life renaissance as an athlete, his inhuman drive, his unique professional approach to training, and the mindset tools he’s leveraged to create improbable success—all of which are layered with a rare and colorful humility. Watch: YouTube. Read: Show notes. Ken is truly one of a kind, and this one is packed with powerful lessons on discipline, self-accountability, and the importance of consistency. Get on board the rollercoaster—and prepare for a thrill. Peace + Plants, Rich Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Rich Roll?

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• 1:13Rich Roll?

  The Rich Roll Podcast.

• 1:18Rich Roll?

  I've run faster every year for 15 years since I'm 35. If you know me, you know I have a huge heart for Tales of Transformation. And today's rendition of this theme is just an absolute banger, courtesy of my guest, Ken Riedau. If you set some goals that are realistic and just progress towards those goals, you can just keep progressively getting better. We talk about his early years, the opioid addiction that nearly cratered his life. It's hard to talk about because it's mortifying. How he beat the odds to get to Wall Street. You're only limited by what you think. Like, if those people can do it, you can do this. And his midlife renaissance as one of the world's preeminent masters athletes, killing it post-50 and racking up titles at some of the planet's most prestigious

• 2:03Rich Roll?

  road races. I found his counsel to be both inspiring as well as highly actionable. And you're gonna wanna strap in because this one is a roller coaster ride. But first...

• 2:19Rich Roll?

  All right, let's do the show.

• 2:25Rich Roll?

  Right on, man. Good to finally meet you. It took a while to make this happen, but I'm so excited to talk to you.

• 2:31Ken Rideout?

  Oh, thank you for having me. I'm so incredibly honored and humbled.

• 2:35Rich Roll?

  Thanks for coming out. It's interesting because your name has come up so many times over the years through our mutual friend Rob, John Joseph, many others. And I think if memory serves me, maybe I'm misremembering, but I think at some point you might have been even living really close to me. Like, were you living out like in the Santa Monica Mountains at some point or in Topanga?

• 2:56Ken Rideout?

  Pacific Palisades in the Highlands.

• 2:58Rich Roll?

  You were there? Okay, I thought maybe you were even closer to me at some point, but I think maybe it was John Joseph. So you gotta get together with Ken. And, and my confession to you is like, I was like scared of you. I was like, this guy is so competitive. Like, if I go out with this guy, he's just gonna wanna throw down. It's gonna be like a thing. And I was like, I don't, you know, I'm a solo guy. I like to go out and do my workouts alone. And it's like, ah, maybe sometime. And then it just never happened. So I apologize for not getting together with you sooner.

• 3:26Ken Rideout?

  I'm sorry that I'm giving off that vibe. People have said that to me.

• 3:29Rich Roll?

  But that's my projection, you know?

• 3:31Ken Rideout?

  People have said that to me, and I can tell you honestly, when people wanna run or ride with me, like, I'm very respectful of everyone's abilities, right? My goal is not to say, hey, Ken, let's ride together. And then I'm gonna like smash up a mountain. Let me show you how strong I am. Like, that's what races are for. That's why I love races is like, I'm gonna empty the tank. I'm gonna try to kill myself. Not necessarily you, but if you get killed in the process, that's part of it. But when I'm training, I love the camaraderie. I love when people wanna do stuff with me. But you know, with running and cycling, if you ask me, can I ride with you today? Then you should expect to do what I'm doing. If I ask you, hey, you wanna come and ride with me? Then I should be expecting to ride at your pace or vice versa.

• 4:07Rich Roll?

  Yeah, it's tricky. I think that was back when you were really into Ironman. And as you know, when you're on a strict training regimen, every workout has a certain purpose. And I would just find that if I went and rode or went running with other people, I'm either going too fast or too slow. But I'm rarely doing what I'm supposed to be doing.

• 4:26Ken Rideout?

  Yeah.

• 4:26Rich Roll?

  And sometimes that's cool because it has to be fun and social and all of that. But you're not always kind of like following the, adhering to.

• 4:34Ken Rideout?

  Yeah, exactly. It's fun, but it's fun, but winning is much more fun.

• 4:38Rich Roll?

  Yeah, yeah, yeah, yeah.

• 4:39Ken Rideout?

  I love, I like to, when I was out here, I rode a ton with Rob Moore. I mean, we spent. I spend more time with him probably than my wife one on one. We just rode a lot. And in that part of it, I really enjoyed riding with other people, but running, you're right. Like, I need to just, I like running with people, but I also know that there's certain things I need to get done during the week.

• 4:58Rich Roll?

  Right. Well, whatever you're doing is rubbing off on Rob because that guy went from a good runner to now like winning races all over the place, like winning the Malibu half marathon. It's like, what is Ken telling Rob? Like, how is Rob leveling up like this?

• 5:13Ken Rideout?

  Hey, it's, everything that I do is available to anyone. You can see every workout I've ever done is on Strava for the last 10 plus years. There's no secret to it. It's just a ton of work and structured and focused work when it's time to recover, recover. And when it's time to train, but at the same time, people will be like, okay, what about recovery? I'm like, mm, yeah, I'm not the best at that. I run it every single day, every day.

• 5:35Rich Roll?

  Well, your whole thing before you got Mario involved as your coach was just basically running 10 miles a day.

• 5:42Ken Rideout?

  Hundred percent with a long run on the weekends for 10 weeks prior to a marathon. And I got down to like 233 doing that with no structure at all. On the long run, I just run hard.

• 5:51Rich Roll?

  That's crazy. And, and running hard every time? Heart rate monitor or any of that? Just going out, crushing it? See, this is why I didn't get together with you.

• 6:01Ken Rideout?

  I would never do that with, with other people. I would never go out and crush. Like, I enjoy the camaraderie and, but yeah, Rob is, Rob's a perfect example of just like, if you set some goals that are realistic and just progress towards those goals, you can just keep progressively getting better. And I've gotten, I've run faster every year for 15 years since I'm 35. And I still got a PR to run this year to like, keep the streak alive. But I think I can do it in Berlin in September.

• 6:28Rich Roll?

  Right. So just to set the stage, are you 51 now or 50? You're 51. So every year since you were 35, you've set at least one new PR.

• 6:39Ken Rideout?

  In the marathon or half?

• 6:40Rich Roll?

  Yeah. So in the half, your PR, I believe is like 110?

• 6:43Ken Rideout?

  110, yep.

• 6:44Rich Roll?

  Which you set in Nashville and 228 in the marathon at C I M.

• 6:48Ken Rideout?

  Correct.

• 6:48Rich Roll?

  Right?

• 6:48Ken Rideout?

  Yep.

• 6:49Rich Roll?

  And that was 2019? When was that?

• 6:52Ken Rideout?

  I, yeah, at the 2000, December of 2019. And then I've run 229 in London and I ran 230 at a few different races.

• 7:00Rich Roll?

  Right. And, and not for nothing, at the New York City Marathon, you were a little slower, 233, but you won the 50 to 54 age group.

• 7:06Ken Rideout?

  Forty, forty and over. I won the Masters.

• 7:10Rich Roll?

  You won, but you won the 50 to 54 by 16 minutes.

• 7:13Ken Rideout?

  Oh, yeah, yeah, yeah.

• 7:13Rich Roll?

  And then the overall Masters division for athletes over 40, and you were like the first guy over 50 to do that, right?

• 7:20Ken Rideout?

  Yeah, yeah. It's one of my most proudest achievements ever. I'm serious.

• 7:23Rich Roll?

  You're killing it as a Masters athlete. London, you got second in your age group, but the guy who beat you was in a different heat, right? So you weren't even able to know that this guy was running faster than you.

• 7:33Ken Rideout?

  Not just a different heat, he started in a completely different start area. So there's three start areas, they merged together around three or four miles. So everyone in the 50 to 54 age, world championship age group category, you had qualified, we had numbers on our front and back. They had gone out of their way to make sure you could see who you were racing. So, okay, I see everyone who's here, let's do this. We take off, by three miles, I can't even see them behind me. It's just me and the motorcycle. So I'm like, I got this, I'm gonna get into the... So now I merge, at three miles, I merge with the elite amateurs, the pros, et cetera, et cetera. So now there's, you know, there's 10 people up the road, three people behind me, it's scattered, but there's people. The kid who, the guy who beat me, he started in some random other start area and took it out at five minutes flat per mile.

• 8:16Ken Rideout?

  So he had like a 50 second lead on me at four miles, and he held that lead the whole time, unbeknownst to me. And when I was done, I was like, come on, man. It's, the thing that sucks is, I know he did it, he knows he did it, and we're the only two people in the world that care about this. But I'm like, you, dude, just race, stand next to me and let's like do this. Let's race head up. If I knew he was there, I would have either caught him or not finished. Cause I would, I didn't wanna finish, I wasn't looking for a finisher's medal. I was there to win the world title. I was very clear, like I knew what I wanted to do was just win that age group. And, um, you know, you don't get a lot of chance to be a world champion. And I was pretty disappointed.

• 8:50Rich Roll?

  Are you gonna be able to go mono a mono with that guy in some of these upcoming races?

• 8:54Ken Rideout?

  I'm not gonna do London this year, cause I'm gonna try to get the age group win in Berlin and Chicago and Tokyo between now and March, and then I'll go back to London. I'll find them some point, we'll, we'll race.

• 9:03Rich Roll?

  Right. So the idea is to be able to collect the Masters world title at all of these big marathons?

• 9:10Ken Rideout?

  Yes, the 50 and over.

• 9:11Rich Roll?

  That's the larger goal that you're going after? It's unbelievable, man, and we're gonna get into the training and the mindset and all of it, but you've got an unbelievable backstory, so do you mind stepping it back a little bit?

• 9:24Ken Rideout?

  No, I'm happy to.

• 9:24Rich Roll?

  Yeah, yeah, yeah, so your upbringing is pretty unique and I think there's a lot to be mined and discussed about like how those experiences, you know, kind of forged how you think about sports and mentality, et cetera, today.

• 9:39Ken Rideout?

  Yeah, when I was growing up, to me, all my heroes were athletes. And it was like my, my parents were divorced, so I lived with my mom and my stepfather. But when I would go, my dad would come and get me a couple of times a week to go play youth hockey. So I was like very competitive athlete as a kid, played with a bunch of guys that played in the NHL, Keith Kachuk, the Sacco brothers, Sean McGeick, like legitimate NHL superstars that were my peers, but then in high school, they just got better and I didn't. And I was like, man, what are we doing the same thing? How are they getting so much better? But that was my LA and those were my heroes. So that was, athletes were my heroes. So I was big, big into sports and, you know, going through life like that,

• 10:23Ken Rideout?

  it was two very different worlds. When I would go with my dad to play hockey and then when I would be home, we lived with my mother's, with my mother's mom and her brother, who was a lifelong heroin addict. So there was like completely unstable household, people, junkies around all the time. It was very uneasy.

• 10:42Rich Roll?

  Yeah, a lot of chaos. Your parents got divorced, so you had your dad, you had a stepdad, right? And, and kind of as I gather, sort of upper, lower class or lower, middle class type situation, basically like blue collar upbringing in, in Boston. You know, my only point of frame of reference for that is whatever I see in movies.

• 11:05Rich Roll?

  But I can, you know, I can imagine what that must have been like, like the, the chaos of that. And then you like, you know, what I've seen as somebody who's been in recovery for a long time is it's sort of that, you know, child of alcoholics, you have to, you're, you're driven to kind of create control amidst the chaos and sports was one thing that you could kind of have domain over. That could be like your thing.

• 11:28Ken Rideout?

  That's right. And I had such contempt for drug addicts and just like.

• 11:35Ken Rideout?

  unethical people and just like the behavior that was going on around me. I had no point of reference to know that these people were effed up, but I knew that I was not comfortable in this environment. I was, I knew I didn't belong there. To the point where my own family and people around me would be like, oh, you think you're better than us, you're arrogant. And I would, in my mind, I was like, yeah, I do. I don't, I'm not supposed to be here. I'm not living like this. This is constant chaos. Like, I don't want this. I want stability and like, I want, I want things in my life. I don't want to aspire to like, get approved for section eight. I don't want to aspire to get like, an extra hundred dollars in food stamps. You know what I mean? Like, my mother sending me to the store with food stamps was like, mortifying. All I wanted

• 12:15Ken Rideout?

  to do was fit in with the kids who had a stable family. And, and for reference, I mean, there was families in the neighborhood where the dad might have been a firefighter or a mailman, and the moms were homemakers. But to me, those were like, the highly successful families. So, in my house, it was like, what perk are we gonna like, get approved for this month? And it was just in my mind, I was like, and again, I had no point of reference, but I was like, come on, man. Don't we want to aspire for more than this? This is embarrassing. Like, I don't want anything for free. And I had a paper roll from as young as I could remember, like, getting up early, folding the newspapers, delivering them in the snow, just because I was like, I don't, I want to have things in my life.

• 12:56Rich Roll?

  Yeah, you gotta take care of your own shit, right?

• 12:58Ken Rideout?

  Exactly.

• 12:58Rich Roll?

  And, and were you able to seek out mentors and your coaches or teachers or anything like that? Like, how did you find parenting outside the house?

• 13:07Ken Rideout?

  Now, that's a good question. I don't necessarily remember having mentors per se, but it's funny, I was thinking about a story as I was driving over here, I was telling Rob, when we were, when I was about 10 years old, I may be getting the years off by a couple, but I was about 10 years old and my brother had mental health issues in hindsight, and then eventually became a heroin addict. But we were like, I was 10, let's say he was nine, and my mother had signed us up for our, for a sleepaway camp. But it was like, welfare camp. So, we go downtown Boston, and we get on the school bus, and it's like, you know, Boston was a very racist, segregated place. So, it was like, maybe there were like, 10 white kids and like, 50 black kids, which is fine. I'm just, I'm painting a picture for you. It was like, an inner-city, like, camp.

• 13:49Ken Rideout?

  So and it was intimidating. So we get there and I was like, I'm going to jail for two weeks. Like I I'm I'm nervous. It's very unsettling. So we get there. My brother's a maniac. So he takes off running in the in downtown. They can't find him. So the school bus leaves without him. So now I'm on my way to like prison camp. And I was telling Rob, I've got a sub sandwich that they bought me and a soda can wrapped in a tin foil, I guess for insulation. I don't know these things that you remember as a kid, right? So I get there and it was like high, like a lot of sports involved. It was like an all sports camp. That happened to be the theme for this this two weeks. So my mother eventually shows up like a day or two later and it's way up maybe in Maine. I don't even remember it was so, but I just remembered distinctly them showing up and calling me into the camp

• 14:33Ken Rideout?

  counselor's office and they're like, hey, your mom's here. I come in there. I'm like, oh, I don't want to be involved in this. Like, I just want to be left alone. I'm doing, I'm serving my sentence. Leave me alone. I'm doing my time. I'll stand on my head for two weeks.

• 14:45Rich Roll?

  It's supposed to be this uplifting, nourishing experience.

• 14:48Ken Rideout?

  No, but it was like a two week vacation for everyone's parents to get rid of their kids. That's what it felt like. So I get there. My mother's like, hey, listen, he doesn't want to be here. Your brother doesn't want to be here. You guys can all leave if you want. And I was like, nah, I'll stay. I'm do my time. I don't know why, even at a young age, I was like, I'm not quitting. I'm here. I'm already settled in. I've got all my stuff locked up under lock and key. I'm sleeping with the with the keys to my suitcase, to my hockey bag, which has my all my clothes with a lock on it and the keys are in my pillowcase because soon as I got there, one of the kids said, hey, let me get those Converse you had on. And I was telling Rob, I had like leather Converse from the Converse factory outlet that were defects. And so one of the kids was like, I want your sneakers. And

• 15:29Ken Rideout?

  I was like, yeah, no, I don't have my sneakers. So then I put them in the bag, lock the lock the bag, take the pillows, take the keys, put them in the pillowcase. So when they came and said, you're out, you're getting an early release. I was like, nah, I'll just do my time here. And I end up winning like camper of the year, every single award you could win there because I think that in hindsight, the leaders must have recognized like, oh, this kid has like something

• 15:54Rich Roll?

  Yeah.

• 15:55Ken Rideout?

  different than the other people here.

• 15:57Rich Roll?

  Like the birth of commitment, discipline, dedication, seeing it through, and then being rewarded for that, probably cemented some kind of neural pathway for you. Like, oh, this is how you make your way forward.

• 16:09Ken Rideout?

  Yeah, I was like, all I can do is like Represent myself the way I want people to view me and, and, you know, and, and we'll get into it later. So then having to deal with my own addiction issues made, just like brought everything full circle of like, man.

• 16:26Rich Roll?

  But being back in high school and then realizing the NHL is probably not your path. Like where, where's your head at in terms of like, what, what, what do you think you're going to do with your life?

• 16:36Ken Rideout?

  Yeah, it was, it was around this time where I like really lost my way is when I went to college. I played football and hockey at Framingham State and I, um, the week before I graduated high school, the week after I graduated high school, I started my first like full-time summer job as a guard in a maximum security prison. And, um, one of the coaches that I had played against in high school, kind of sought me out after the game and said, what are you going to do for work? He just, he knew my dad and he said, um, I've got a job for you at the prison. And I was like, oh, cool, man. I'm going to be cutting grass and stuff like maintenance. I showed up there and they hand me like basically police uniforms and they give us like a half a day of classroom training. Like look for this, they put a knife here, this, I mean, it was like, this is like.

• 17:19Rich Roll?

  That's insane. A half day of training to be a prison guard?

• 17:22Ken Rideout?

  There's so much information coming. I'm like, holy, I thought we were cutting grass when I got here. Now we're like guards in a prison. I mean, I had known when I was a kid, my stepfather got sent to prison, which was fucking mortifying as like, you know, fifth, sixth grader, he was like, oh, uh, he's going to prison. I'm like.

• 17:40Rich Roll?

  What'd he do?

• 17:41Ken Rideout?

  Like theft, uh, petty theft and like crap. Like I think credit card scams. But I was just like, man, come on, why is this happening to me? Like you guys can't behave yourself. I'm, I'm going to be out of here soon. Like I was just mortified. This is in like fifth or sixth grade roughly. So then around eighth, maybe ninth grade, he gets out of, he gets out of prison and we, he was, we, he's a nice enough guy. He's just, he is what he is. I'm not going to like go scorched earth on him. He's, he's nice enough. He was doing the best he could with, I mean, my mother was crazy. So having, everyone was in a bad situation. But so he gets out of prison and like, hey, he's got a new job. And I'm like, okay, cool. I could care less. Uh, he's a janitor. All right, cool. At your high school.

• 18:26Ken Rideout?

  I was like, come on, stop, stop. I was like, please tell me that this is a, you're joking with me, right? And they're like, nope. And I was literally like. The good news is, you couldn't do anything more embarrassing to me. Right. Did you get bullied for that? I never really got bullied because I wasn't like a pushover. But I certainly like would imagine that even if it wasn't true that people were shit talking me behind my back. But I, but there was a part of me too that was like, I can't control the actions of other people. I had had a brother who had gotten to a fight every, been kicked out of every school, gotten into fights, wasn't an athlete. It was just like a bad kid, which was always constantly haunting me. So this was just another like, this was just another drop in the bucket of like, come on, man.

• 19:09Ken Rideout?

  Which is part of the reason why I was like, I gotta get out of here. So you take this job as a prison guard? So I start working in the prison, walk in there the first day and this big Irish gangster from the streets who I knew from the projects comes running, picks me up on his shoulder, he's running around with me in the prison yard. And I was thinking like, dude, come on, man, put me down, the other guards are watching. I didn't care about the inmates. I was like, I don't want the guards to think I'm like fraternizing with the inmates first day. But it was almost his way of saying like, no, no, no, I'm letting everyone know you're with us, like that we know you. So like, this is a dangerous place. People should know that you know people here. It's just like being an inmate. If you go to prison, it's very segregated. If you don't know the people in your race as being a street person, you're gonna have a problem. Cause they're, they're all gonna wanna have a problem with you.

• 19:52Ken Rideout?

  Right. Like they're gonna protect you as opposed to the other way around. I mean. You know, were you seventeen, eighteen years old? I was eighteen, just out of high school. I mean, I looked like I was probably thirteen. It was, it was crazy. It, it, it wasn't as crazy in reality as it sounds now as we sit here talking in Malibu. But at the time. Right. You know, I was, I grew up with most of these people. I mean, these were the bad people, but I, I knew a lot of them. So when I got there, it was kinda like, hey, what's up? You know, like. And what was the day to day experience of working there like? It was the opposite of what you think of with like a Shawshank Redemption. It was a very hostile, intimidating place.

• 20:34Ken Rideout?

  If the prison, if an inmate had a problem with you, they'd punch you right in the face. They wouldn't hesitate. They, they demanded respect within reason and you know, the same that I would demand from them is like you'd show mutual respect. And it's always like, imagine being a substitute teacher at a high school full of fresh little kids and they're always testing you. And they're doing things that you can't really, you're not gonna really like come down hard on them. But it's kinda like, we're getting close to like the line here of where. And you can't back down. No. And you being this young kid.

• 21:02Rich Roll?

  Going face to face with guys, you know, hardened criminals, guys much older than you.

• 21:07Ken Rideout?

  But I always tell people, just because you're in jail, being stupid doesn't make you tough. There's tough people, there will be, there's tough people in Malibu, there's tough people in the private schools, public schools, prisons. Tough is tough. And that's the one thing I've learned over the years in, in terms of like, kind of vacillating between these different worlds is that tough is tough. You mess with the wrong person, you're gonna have a long day ahead of you. So, but yeah, the inmates, they weren't necessarily all tough, but they were all pretty crazy.

• 21:34Rich Roll?

  Yeah. Did you end up in violent altercations there at all?

• 21:38Ken Rideout?

  Oh, yeah, multiple times. I got hit over the head with a pillowcase that had a weight in it once, fractured my skull. I got, an inmate said, if you didn't have that badge on, I'd punch you right in your face. I said, oh, really? And I went to take the badge off and he punched me right in the face before I even put my hands on it.

• 21:51Rich Roll?

  Oh, my God. How long did you work there?

• 21:54Ken Rideout?

  Uh, three summers, three or four summers.

• 21:57Rich Roll?

  Yeah.

• 21:57Ken Rideout?

  But there was one incident where I was working there with a friend of mine called Brendan Daly. He eventually became a singer called Spooky Daly. And he's a director and producer now, real, very successful. But him and I were working in the like modular building, which does the main building, which is has like cells, like you would think. And then there's like modular buildings, which were more like dormitories. So inmate came in and some of the other inmates were teasing him. Again, this is like, it's not like a movie. It's like a high school full of jerks and they're bullying kids. It's just like that. You know, there's like, there's sexual things going on, but people don't realize that if you have a hundred guys, the chances are that there's some like, there's some gay guys in there that are voluntarily like, having relationships with people. It's not this like, full of sexual predators per se.

• 22:41Ken Rideout?

  There is, but it's not that overt. So kid comes in, so they're teasing him and telling him they're gonna get him and stuff. And, and he's new. And they send him down to the warden's, the warden's office, the warden of the dormitory. So the guy is superintendent of the dorms. And he calls me and Brendan down. And we're like the like dopey summer help that the other guys, so that they hired all these college kids, so that the full-time guys could take summer vacations and they wouldn't be short-staffed. So they call us down and we get on there and that poor kid, he's like, you know, he's a little bit older than me, a little bit bigger than me and my friend Brendan. And, um, He's in a position now where he's not gonna tell on them. Cause you're not gonna be a rat, like that's gonna change the trajectory of your time. You're gonna go to protective custody.

• 23:24Ken Rideout?

  But he also is now in with the superintendent, like. Everyone's gonna be watching how this whole thing plays out, so he's realizing shit, I gotta do something. So to save face, he picks something up off the desk and half ass says to the guy, I'll bash your head in with this. So that he says to me and Brandon, get this guy out of here. So we handcuff him and he's struggling and I'm like talking to him, I'm like dude, will you cut the shit? Like dude, stop, like let's make this easy. And he's like, now he's like, we're on him and it's just like a movie. He's like, oh fuck you, don't hold me back, like I'm like, come on. So we get down to isolation, the superintendent of the whole prison comes down and they're all standing in isolation. They put him in the cell and they're like, okay, take your clothes off, strip search. You always strip search anyone every time, anytime they move from buildings and um.

• 24:09Ken Rideout?

  He says, I'm not taking my clothes off. And the guy says to me, Ken, get in there and strip his clothes off. And now we're like down in a dungeon in this like 50s era like bunker. And I'm like, oh my God, I can't believe this is happening. I'm in a cage match. I go in, they close the door and I'm like, take your clothes off. And he stood there for a second, I said, this is your last warning, cause now I'm just like gonna go attack mode. And he just finally takes his clothes off and I was like, oh, thank you, Jesus. And I got out of there.

• 24:35Rich Roll?

  Right, cause no one's coming in unless something goes down.

• 24:38Ken Rideout?

  No, this kid's getting a beating. Either I'm gonna beat him or they're all gonna come in and beat him up. But he's gonna like, if he's getting the better of me, they're gonna get him. But still, I don't, I'm still a normal person, I don't wanna be in a death match in a prison. But I use that story as an anecdote for life because when. You think about things that are scary or intimidating, like training with someone or running a race that you're nervous about. Or any situation in life you're nervous about, especially with running. I'm like, I always tell people this, no one's gonna punch you in the face. No one's gonna hurt you if you're not, if you can't take anymore, you can just stop whenever you want. So when you think about that in relation to being in really intimidating situations. Running to me is like, come on, man. This is just, this is easy work.

• 25:22Rich Roll?

  Yeah, I know you've said, you've said in the past that when you were starting to really get into running, you kind of looked around and you saw a bunch of skinny guys. And you're like, you know, I was a prison guard. Like, how hard can this be? Like, I can, I can out tough these guys, right? But just because they're skinny doesn't mean they're not mentally tough.

• 25:40Ken Rideout?

  Well, listen, I say to all the time.

• 25:41Rich Roll?

  Because you don't have to box.

• 25:42Ken Rideout?

  I say to people all the time, like, look at these guys are like running dweebs. But I count myself in that group. And I mean it with affection. I don't mean it literally. But, but it doesn't matter what the reality is. It's what I tell myself. So I tell myself, these guys are soft. They're wimps. That's not the truth. I, I, I use, I'm a rational person. I know that this, like I just said, there's tough people everywhere. The nerdiest looking guy might jujitsu your ass into submission in three seconds. But that doesn't matter. What matters is the story that I'm telling myself. And I'm telling myself, I'm 10 times tougher than everyone. And until someone proves otherwise, I think I can win the New York Marathon, the whole thing. You know, like, I go in with the attitude.

• 26:21Rich Roll?

  Where does that like confidence, that brashness come from? Is that just built into you? Did that, is that born out of all of these experiences that you had as a young person?

• 26:30Ken Rideout?

  I think so, because at the core of me, I'm like, super, super anxious, insecure, nervous, just like anyone. I have all the similar insecurities, if not more so, that I, I wouldn't say I'm overcompensating because I'm not trying to run from that. I know that that insecurity and that fear is there and I.

• 26:51Rich Roll?

  It's a tactic to, to overcome that insecurity.

• 26:54Ken Rideout?

  Yeah, and I try to keep the fear in, in, in check. But I never try to deny it because I tell people all the time, like, someone, at one point, every single, the best fighters in the world, at some point, they walked into a gym for the first time and was scared shitless. If you walk into a boxing gym or a, or a fighting gym and you don't have experience and you're not scared or nervous, like, that's not normal. And anyone who says anything different, I think, is lying. Well, they're crazy. So I think it's important, an important element of my training and racing and the stuff I do with endurance is to acknowledge that, yeah, I'm scared. I'm, I'm nervous and I, I may just be nervous and disappointing myself, but I'm nervous and I'm scared. And, and, but those feelings let me know that it's time to like, get.

• 27:39Ken Rideout?

  Dark.

• 27:40Rich Roll?

  Yeah. Dig deep, even when it's the turkey trot.

• 27:44Ken Rideout?

  A hundred percent. Turkey trot coming for your neck.

• 27:47Rich Roll?

  Yeah.

• 27:47Ken Rideout?

  I'm elbowing forearm shivering people on the start.

• 27:51Rich Roll?

  Oh my God. But the prison guard thing was always intended to be a summer job, right? It wasn't like this is going to be my career path. Like you had already gotten into college and were planning on.

• 28:01Ken Rideout?

  I was in college, but to give you context, like I had no guidance. I filled out that's application to Framingham State because it was one of those applications where you fill out the circle with the pencil. You know, you fill in the like, put the circle next to the letter of your name. It was like, you know, you had to write like a two-page essay. It was not, it was just path of least resistance. And I literally chose sociology because the kids that I was playing football with said, this is the easiest major. And I tell you this, not, I'm not proud of this. I'm embarrassed. I'm ashamed of myself, but I just didn't, I didn't know what I didn't know. If I could go back and do this all over again, I would have 100% gone to either Naval Academy or West Point. No question. That was where I should have gone.

• 28:41Rich Roll?

  Well, you didn't have anyone at home to guide you through this.

• 28:43Ken Rideout?

  Exactly. So when I got to Framingham State, when I first got the job in the prison, it was almost like discussed for a minute amongst my family like, oh, this could be, you could just get your degree and segue right into like a probation officer job or some kind of like counselor job in the prison. And after a week of working there, I was like, are you crazy? Never mind the inmates, the guards I was working with were 10 times worse. They were like, they were terrorists. I mean, I was having fistfights with, with other guards after work, grown men. It was, it was horrible.

• 29:12Rich Roll?

  Wow. That's intense, man.

• 29:21Rich Roll?

  But it's not surprising you somehow found your way to Wall Street, right?

• 29:25Ken Rideout?

  Like that's, yeah, so.

• 29:28Rich Roll?

  By hook or by crook, not by, you know, academic pedigree.

• 29:32Ken Rideout?

  No, and that's, to be honest with you, I am like, can be very self-deprecating and I'm aware of all my weaknesses and the mistakes I've made, but there are things that I've been proud of that I've accomplished along the way. And one of those things is, um, going to New York and seeing that there was opportunity, that kids were working in finance and, and make, and making money and being successful. And I was like, same thing with running. I was like, these kids can do it. They, they have fancier degrees and someone told them about this earlier, but if I can just get onto a trade-in desk and get my foot in the door, I can kill these guys. I can out hustle these guys. I know I can. And when I say it now, it seems crazy because it almost seems delusional at the time. I had a sociology degree in Framingham State. I was working with guys who had Ivy League undergrad,

• 30:15Ken Rideout?

  Ivy League MBA, and now all of a sudden, we were on the same trading desk. But I'll step back and like, kind of explain to you when I, how I got to New York and segue into that. So I got my first job as like pharmaceutical sales job. It was awful. But I lived in New York and I-

• 30:30Rich Roll?

  Gosh, and everybody needs that thing that gets them to New York. Once you're there, like you're, the window of possibility opens up.

• 30:38Ken Rideout?

  So I get to New York and I'm doing pharmaceutical sales and pharmaceutical sales is the biggest racket ever. When I tell you I probably worked 30 minutes a day, that would be aggressive. It was, it wasn't good for me. I need structure and, and it was like you're left to your own devices and I would, I hated it.

• 30:53Rich Roll?

  You had to drop in on doctors' offices-

• 30:54Ken Rideout?

  Exactly.

• 30:55Rich Roll?

  Giving the samples and all that kind of stuff.

• 30:57Ken Rideout?

  So it just became an exercise in like dropping the samples, getting the signatures and taking off. Like I just had no guy, I had no direction. I, I knew I didn't want to do this. So I was working out at the gym and playing in a men's league, hockey league in Chelsea Piers. And one of the kids who I happened to just play with on a pickup team was an inter-dealer broker. So he was brokering institutional trades between the banks. It was kind of like the bottom rung of the like prestige ladder in finance. Like inter-dealer broker is kind of like the bottom rung in terms of prestige. But you could make a lot of money, millions and millions. There were people getting fabulously wealthy doing it. But it was, I always told people this was a job. It wasn't a career. You're only as good as the relationships that you have with certain traders that were at banks.

• 31:40Ken Rideout?

  That eventually those guys went to hedge funds or asset managers. So there was constant turnover. So I got onto the trading desk. This is actually a funny story. I got onto a trading desk as like the assistant. And I was the assistant, so I was covering young guys at Enron doing like next day power trades, which were kind of like a necessity for the senior traders to do the bigger trades with your senior brokers. So the junior people were talking to junior people at Enron. The trade was like made $10 in commission. But it was a necessary evil for the electricity traders that the next day power had to flow. So they had to trade that, balance their books. And then if you did a good job there, they would reward the senior people with their like real trading. So I was doing that and there were like two or three guys there just hazing me,

• 32:24Ken Rideout?

  which was a whole new experience to me. I was like, these guys are hazing me like I'm a dweeb, like I'm a nerd, like they're just, they're, they're, they're being abusive towards me. I was like, I can't believe I'm allowing this to happen. Like at some point.

• 32:35Rich Roll?

  Little do they know, like you are a prison guard, right?

• 32:37Ken Rideout?

  I was boxing for the New York Athletic Club. I had a black eye every other day. They know, but they just like, it's just typical finance, bro, bullshit. And they were like terrorizing me. And one day the guy threw a dry eraser at me and I just slapped him in the face. And I was like, we're not doing this anymore. You got the wrong guy. And they were like, uh, you're fired. I was like, oh my God. I had, when I say I had no money, I was literally making like 40 grand, but by the time I paid my rent, my student loans, everything, I was like negative. So, this is, this is so funny. I called from a payphone, mind you, this is in like 96. I called the kids at Enron and I was like, dude, I just got fired. I'm gonna tell you what happened. Coincidentally, the senior trader at Enron, who was like the Gordon Gekko of commodities at the

• 33:21Ken Rideout?

  time, was from Martha's Vineyard. And he, he heard the story and was like, give me that kid's number. So he calls me and he says, hey, I heard what happened. Call this guy at, I didn't even know we had competitors in what I was doing. But one of the competitors got in touch with me and was like, this was, let's say a Thursday. He's like, can you stop Monday? And I was like, start what? He's like, well, you come work here on Monday. I was like, okay. I was making 40 grand. The guy goes, we'll pay you, uh, how's 80 grand? I was like, 80 grand? That was more money than my dad made. I was like, I'm rich.

• 33:52Rich Roll?

  Was it like, oh, that, that there was something about you slapping that guy that appealed to him? Like, oh, yeah, yeah. This guy's a gunner. We need this guy on our team?

• 34:00Ken Rideout?

  Yeah. He was like, what happened? And I told him and he was like, standby. So then, then when I got there, he, they, he told the guy who hired me, like, that's my broker. So he starts calling me and saying, buy this, sell that to the guys on the desk. It's like, it's like Bud Fox in Wall Street when Gordon Gekko starts giving him orders.

• 34:18Rich Roll?

  Yeah, I'm thinking about that. I'm thinking about the Jordan Belfort origin story.

• 34:21Ken Rideout?

  That's exactly what it was. All of a sudden, when I tell you I was making 40 grand, within two or three months, they're like, your new salary is 125. Now, keep in mind, they keep raising it, but I'm probably making like three or four million dollars for the trading desk.

• 34:33Rich Roll?

  Yeah.

• 34:33Ken Rideout?

  But I just don't know enough to even know what to ask for. To me, it was like, I think they made a mistake. Hundred twenty-five grand. Do they know I'm an idiot? Like, they're crazy. So I started just grinding away. And then eventually, the guy who hired me there went to, he went to Cantor Fitzgerald to run their electricity business and said, hey, come here, come work here. And I said, I have a contract. You signed it. You know, I can't leave. Like, we have a real contract. And he's like, okay, go to London for a few months and then come back. And so I did. And while I was in London, nine eleven happened, and all those people that I would have worked with were on the top floor of the World Trade Center. But then you went to Cantor after that? No, no, I, so I went to Cantor. So you were employed by Cantor when nine eleven happened?

• 35:17Ken Rideout?

  And I was going back and forth between London and New York. I was going, I was about to leave for the airport to go back to New York to work for a few days. And nine eleven happens. Wow. Yeah, it was crazy. So obviously, you knew a lot of those people. Oh, a ton. I mean, I worked there a few days a week. I was flying back. I mean, this is how crazy it was. Two years before, I was making forty grand. Now I'm flying the Concorde back and forth from London to New York. It was, and every time I would be like, I'm living someone else's fantasy. Yeah, that's unbelievable. What do the guys back home think?

• 35:48Ken Rideout?

  I think initially, people were like, it's, it's, it's almost like a natural instinct to be like, F that guy. He thinks he's better than us. It's like crabs in a bucket. No one wants to like, they want you to succeed, but not really. It's like if you're half-ass succeeding, if it's very visible, like you're playing in the NHL, they're all like, your biggest fans, they'll kill someone for you. But if you're kind of just pulling away financially, there's that crabs in the bucket thing of like, they don't really want to see you succeed too much. Yeah, you're not all that. Exactly. And I would say that that has dissipated immensely since I started doing the podcast with Teddy, but we can get into that in a minute. But yeah, when I was doing all this stuff, it was fun. And of course, you know,

• 36:29Ken Rideout?

  I wanted to like, share the wealth with everyone. I was always been, you know, maybe overly generous. And I would always have friends fly down to Boston, fly down to New York. We'd go to fights, we'd go to sporting events. It was just, in hindsight, it was all a bit too much too soon. And that, and, and around that time was when I was like, really suffering from like, fraud complex or imposter syndrome. And was like, super uncomfortable just with the way. Things were going, I always, I say like the fear of having money and losing it was 10 times worse than never having money. That anxiety around not making mistakes once I had had some financial success, just,

• 37:10Ken Rideout?

  it was overbearing and that environment, working in finance in, at that level was incredibly, incredibly stressful. Like I said, the relationships that you maintained dictated essentially your compensation and trying to maintain those relationships and, you know, be a good person without being like a, you know, a complete ass kisser or, or, you know, like just constantly living and dying with these interactions with other men and women was, it was just a lot of emotional stress that I wasn't prepared to deal with.

• 37:43Rich Roll?

  Right, being so young and really being inexperienced in the workplace to get thrown into that pressure cooker with the imposter syndrome and diluting yourself with the belief that the, the money is going to take care of all of those feelings, right? And so what happens? You end up compensating in other unhealthy ways.

• 38:03Ken Rideout?

  That's exactly right.

• 38:04Rich Roll?

  Yeah, I want to get into that, but, but, but before I forget, I did want to ask about what it was like to return to New York City after 9/11, being a Cantor employee. I mean, it must've just been devastating.

• 38:18Ken Rideout?

  It was devastating, but again, the people, it wasn't like you had these relationships with people that were like lifelong friends or family. It was like we were almost like mercenaries together. It was, it was, it was, it's hard to explain if you've never been on a trading desk, there were some people that you really like and there's some other people you really dislike. And that's the one thing that I don't miss is having conflict with people. Since I've worked for myself and segued into the stuff that I'm doing now that we can get into later, it's like I've never felt more at peace and, and, and never had less conflict with people. And it took a while to come to that realization that that was what was going on, but you know, like being, going through rehab and recovery, you kind of like realize these things

• 39:03Ken Rideout?

  that you had never considered before, but going back to New York after 9/11 happened was, yeah, it was traumatic, but I, You know, I think some people who had some loose affiliation or knew people that were there, they, they, they, it hit them a lot harder and they, and they, and they held on to that trauma probably more than I did. Whereas I was like, it is what it is. Like, thank God I wasn't here. This is awful, but I can't let it consume me. It's, this is, you know, like the ups and downs of life. But it was, yeah, it was, it was difficult. I mean, we were in the building in, in London and, and on open calls to the New York, like to New York. We had like an open line of communication. There wasn't video, but you

• 39:46Ken Rideout?

  had an open line. There was a guy sitting next to me, his brother and his dad were in the building. This whole thing played out in slow motion. It wasn't like, oh my God, the building's down. It was like, oh shit, someone hit the buildings with, what is that, a Cessna? Then the second one hits you like, oh my God, I hope they can get out of there. But never like, oh my God, this is, this is about to get ugly. And then when the buildings fell down, then it was like, wheels off.

• 40:09Rich Roll?

  Yeah.

• 40:10Ken Rideout?

  Chaos.

• 40:11Rich Roll?

  So you come back to New York?

• 40:13Ken Rideout?

  Yes, I come back to New York, back and forth. But I mean, we were in, once that happened, like there was no real office in New York for six to 12 months. So I was in London, working around the clock, trying to cover.

• 40:23Rich Roll?

  And are you with your wife already at this point?

• 40:25Ken Rideout?

  No, no, I was, um, single at this point, thank God, because I still had a lot of mistakes to make and a lot of pain, a lot of mistakes to make.

• 40:33Rich Roll?

  Well, let's get to that.

• 40:34Ken Rideout?

  And pain to go through.

• 40:35Rich Roll?

  The imposter syndrome, too much money, too young, you know, of course, drugs are gonna enter the picture.

• 40:42Ken Rideout?

  Yeah. And, um, you know, probably in college, as soon as I lost that like, um, connection to sports, I kinda lost a little bit of my identity there and, and everything kinda went downhill. My relationship with my dad, which was good as a child, but in hindsight, I think it was, the sports was as much for him as it was for me. You know, he, they had, my parents had me when they were 19 and 20, my dad being 20. So I tell people all the time, man, when I was 20, my dad was 40. I'm 51 now. My oldest is 13. Like if I had a 20 year old kid in the house, like, I'm a monster. I'm like, I need everything a certain way. If I had a 21 year old kid in there wreaking havoc, I'd be like, dude, what are you doing? Like, you have to be in at 10pm.

• 41:22Rich Roll?

  Yeah.

• 41:22Ken Rideout?

  Everyone has to be.

• 41:23Rich Roll?

  It puts it all in perspective a little bit. Yeah. You can have a little more compassion.

• 41:27Ken Rideout?

  So I think when I started playing hockey, like a lot of that, and I started playing sports, a lot of that stuff started to like, I didn't realize that it was. An emotional baggage for me that all of a sudden I was like, man, is that where all my value was tied up in the fact that I was playing sports and it gave him an outlet to go and watch? Maybe it did, maybe it didn't. I don't wanna like go scorched earth on him per se, but you know, it was like it's massively affected the way I interact with my own kids with sports. I have my own outlets. I don't need them to be, I don't need to live vicariously through them. I want them to be great and I want them to be happy. And yes, I'd love them to be Olympians and professional athletes, but I'm planning for them to have a career in like, you know, being a good person, doing something reasonable.

• 42:11Ken Rideout?

  But yeah, so when all that stuff happened and my life started to change and I was now working in finance, high-paced, high-paced environment. It's important to note that, and people say this all the time, that like money doesn't make you happy. I know people who have never had money or want more would say, oh, this guy's crazy. But I'm telling you, as someone who's had, lost and made money, I did not feel one ounce happier than I do today than I've ever done. Like, there's no correlation for me. You have different stressors. There's different things that cause me anxiety and cause me to like not be as peaceful as I can be that comes with, that came with money. And all I can tell you is if you're a happy person, you'll be happy with money.

• 42:56Ken Rideout?

  If you're an unhappy person, you'll be unhappy with money. You'll just be unhappy about different things. And all I can tell you is I was incredibly poor and then, I don't wanna say fabulously wealthy, but I had enough money to do anything I wanted and I was not any more peaceful with myself. Matter of fact, I became fucking addicted to drugs. And yeah, it's hard, like it's hard to talk about because it's mortifying. Like I look, you know, for the longest time I would've said, these people are losers. Get your shit together, stop being such a loser. And then in the, in the background, I was like justifying my own horrible behavior. And I think when you go through that, it's hard to realize at the time what you're doing.

• 43:38Ken Rideout?

  It's only in hindsight and reflection and going through therapy and, um, you know, recovery to a certain extent that you start to look back at these things and like, why was I doing that? Like, when you're in it, when you're kind of in the storm, it's hard to like have clarity.

• 43:55Rich Roll?

  Yeah.

• 43:56Ken Rideout?

  And, and, and recognize.

• 43:57Rich Roll?

  Of course, because you want to be able to continue to pursue it. So you tell yourself a certain story about your relationship to the thing. And you having your brother who's a heroin addict, I'm sure every fiber in your being was, you know, I'm not going to be like him. And whatever you were doing, I mean, what was it? Coke? Like, what was the thing?

• 44:16Ken Rideout?

  No, to be honest, I mean, I did do coke, but it was never, that was never a problem because after I did coke for like three or four days, I'd be like suicidal where I'm like, I can't believe I did that again. I just wasted a day of my life.

• 44:26Rich Roll?

  You did just slip in, like, I would do it for three or four days.

• 44:28Ken Rideout?

  No, no.

• 44:29Rich Roll?

  Yeah, it wasn't that bad. It wasn't a big problem.

• 44:30Ken Rideout?

  Like every weekend for a couple of years.

• 44:33Rich Roll?

  Yeah.

• 44:34Ken Rideout?

  But I realized quickly, like, if I don't have a drink, I would never think, let's get some cocaine. As soon as I had a drink, I was like, that's the best idea of that all day.

• 44:41Rich Roll?

  Well, the alcohol opens the door.

• 44:43Ken Rideout?

  But that to me, the, the, the high and low, that the low was so low that it was easy to eventually be like, all right, I've kind of outgrown this. But the opioids was the drug of choice. That's where I found.

• 44:53Rich Roll?

  And did that start with, after a surgery?

• 44:55Ken Rideout?

  Yeah. Yeah. I had a small surgery on an ankle. I don't even remember what it was about, something with an ankle tendon, but he gave me like seven Vicodin. And I was like off to the races. As soon as I took it, I was like, holy shit, I feel awesome. I, I had surgery on my shoulder recently and they gave me, um, the woman made a video, the nurse, they were super friendly. I had, they were going to give me a nerve blocker before the surgery and I, and they were like, we're going to use an ultrasound guided needle. And they had given me a PRP injection two weeks before to see if it would help. And they used ultrasound guided needle. And when I heard, and he's like, yeah, just so we can see the needle and get it on the nerve with the PRP. And it hurt on a scale of one to 10, it was a 20. I almost fainted. I was like, that's the most painful thing that's ever happened. I'm never, so when they said, we're going to give you a nerve

• 45:40Ken Rideout?

  blocker with this ultrasound needle, I'm like, I can't, guys, I can't, I'd rather not have the nerve blocker. And they're like, oh, let us give you something in your IV. So they give me the drug in the IV, which I thought maybe like Xanax or something. And all of a sudden I was like talking to the woman, I'm like, oh my God, I feel unbelievable. What is this? And she's like, oh, that's fentanyl. And I'm like, I've never been so high, leave me here. And I, she was videotaping me to send to my wife. I said, I've never been so happy, leave me here for an hour before the surgery. That's all I can describe to you is if you look at that video, that's how I felt when I tried the drugs. I was like, I found, this is awesome. And then initially it starts out like, you know, a couple of evenings a week. You know, I'm just gonna watch TV, take a Vicodin, I'm gonna be good. Then that leads to like, I feel like shit the next morning.

• 46:25Ken Rideout?

  I wonder if I take one in the morning, if it will like kind of take the edge off, get me through the day. And that went from like, this all happened in the course of like two weeks to like, I'm taking them like breakfast, lunch, dinner. And then every day, as soon as I get up, boom. And then I would do that for a few months. And then I would be like, okay, I'm done with this. I'm gonna like white knuckle this and go through withdrawals on my own in silence. Cause I would never admit to being such a loser. And I would just suffer through these withdrawals, being sick. And it just became a cycle for years of on, off, on, off. And I'm very resourceful, so anywhere I went, when I was in London, I had, there was a doctor that did doctor calls.

• 47:07Ken Rideout?

  And he was alcoholic and I knew he was, and I just knew if I gave him 200 in cash, he would give me a prescription for anything. And it was like literally the worst thing that ever happened because that's what kept me in business while I was in London. Otherwise I, I didn't, I didn't know enough people to have strong connects there. So I would have been eventually just gone through the withdrawals, had enough. I don't know if you've, if you've experienced this, but after like 60, 90 days without substance, it's very easy for your brain to get like reprogrammed to like, you don't even miss it anymore. And then one day you're just like, I wonder, you know what would be a good idea? It'd be fun to just get high one time. Right. It wasn't that bad. Yeah. And that one time will lead to like a six month odyssey. And then I'd be like, I can't believe I've done this again. Right. That narrative around just keeps spinning around.

• 47:52Ken Rideout?

  And on. And I was a functioning addict, so no one knew except me. And it was just, I think the- You think no one knew? That's a good question. I bet some people knew. No one has ever said to me, I knew you were doing something, ever. But your moods had to be erratic. I was so aware that I was on drugs that I was like, did my best to keep it in the control, but I was a monster when I was on the trading desk. I tell people all the time, I hated who I was. It was an aggressive, aggressive place. It was like an open outcry market, meaning if you all say, hey, I got a 10 bid, and someone's like, I'm at 20, and then someone jumps up and is like, sold at 10. If two people do that at the same time, it's like, who gets the trade? All of a sudden, there's people screaming at each other, and the customer's on everyone's phone. So you have two phones in your ears,

• 48:36Ken Rideout?

  you're screaming all these orders. And what if we both scream, you're done? And then they're like, ah, guys, let me know who did it. And now it's like, fuck you, fuck you, I'll kill you. You know, and it was like, and I just was like, okay, I'm gonna be the biggest bully amongst the bullies, or the biggest lion in the jungle.

• 48:53Rich Roll?

  It's such an insane way to make a living.

• 48:55Ken Rideout?

  Insane. And there's people still doing that right now. I'm sure there's people listening to this.

• 48:58Rich Roll?

  In 2022, like, isn't there a more efficient way to take care of this kind of business?

• 49:03Ken Rideout?

  There are so many, dude, there's so many protocols on top of that. That's so that's, so that's like an open outcry commodities trading. Bond trading, you'd be like, okay, I'm a 10 bid. Okay, I'm at 20. Now these two people are engaged in a negotiation, no one else can get involved. So you would tell your client, hey, they're 10 at 20 right now, buy those at 20. I'm like, they're engaged, I can't wait, I gotta wait till they're done. So you're like, sitting there quietly, and this guy says, like, last look at 10. And I'm like, mine at 20. And someone will be like, you son of a bitch, I was gonna buy those, I was spoofing them, saying my last look at 10. There was just different, different protocols and different products. There was parts of it that were fun and exciting, but doing that every day, 24/7, it was, it was too much for me. I just.

• 49:49Rich Roll?

  You need a boost.

• 49:50Ken Rideout?

  I, when I think back on it, I have such bad thoughts, bad feelings. It was not a good lifestyle for me.

• 49:58Rich Roll?

  So how'd you, how'd you eventually get off that merry-go-round?

• 50:01Ken Rideout?

  Probably when, I mean, really, the final time was when, when I was in London, I went to NA and just like, did the whole thing, went through meetings and had some good time under my belt. I met my wife, we got engaged, and then I started to like, fall off the wagon again. And then really, when we started to have kids and adopted my daughter, that was when I liked the last time where I was like, okay, this is like.

• 50:25Rich Roll?

  So it went on for a while.

• 50:26Ken Rideout?

  Oh, a long time. Yeah. Yeah. And I'm believing it's, it's a huge source of embarrassment. But it's like, I, what am I gonna do? What, who's gonna be helped by me? Keeping this secret to myself, if I can help someone to by sharing this story and saying, you know, I think like you said, I see Ken, I don't want to run with him, he's so intimidating. People have this impression of me from my online persona that I don't even realize I'm giving off. And people tell you, people say to me, you're inspiring and motivating. And I'm like, I don't know what I'm doing. I'm just like posting random thoughts in like my, my day to day activities, which include keeping myself busy by exercising and spending time with my kids.

• 51:08Ken Rideout?

  So there's a lot of like mixed emotions with it because yeah, it was a lot, I wasted a lot of time. And if, and if I just accept that and, and let it fester, it's not therapeutic to me. And, and if I can help someone by saying, hey, listen, this is what I did. If you know, like, maybe they know someone who's going through that and their comment might set the person on the right track.

• 51:29Rich Roll?

  Oh, sure.

• 51:30Ken Rideout?

  Or maybe someone hears this and goes, you're right, dude, there's so much life to be lived. And it look, I mean, I started getting competitive at thirty, at thirty-five. And at fifty, I won my first marathon.

• 51:43Rich Roll?

  Right.

• 51:43Ken Rideout?

  I know it sounds crazy to people, but I'm like, it's like rehab, it's like being sober. If you don't take the first step, you're never gonna know what's at the top of the mountain. And if you think climbing the mountain, just you're, you're getting up there just so you can have that view and be like, I did it. I won a marathon. No, the climbing is the hard part. When you get to the top, there'll be another mountain in the distance. I promise you, if you win Olympic gold, you'll want to win another one.

• 52:10Rich Roll?

  Well, listen, shame can't survive the light. You know, you said you're embarrassed by this. There's nothing to be embarrassed about, but the more that you share it, the less embarrassing it is. And that shame dissipates because it is in service to others. You know how many millions of people are walking around popping opioids and don't want people to know about it? I mean, untold, hundreds of thousands of people.

• 52:34Ken Rideout?

  It's crazy. And the one thing, the one thing that happened that helped me massively was, um, I was introduced to a drug called Vivitrol. And Vivitrol is a, um, an extended release.

• 52:45Rich Roll?

  Like a blocker.

• 52:46Ken Rideout?

  Injection of an opioid blocker. It's an intramuscular injection once a month. And when you take that, you can't get high, it blocks, blocks the receptors. And I know, cause I tried and you can't.

• 52:59Rich Roll?

  Like a good addict, you're like, I could do an end run around this.

• 53:03Ken Rideout?

  I'm the best at this. I know how to beat this. But really that like drug changed, changed everything for me. Cause as long as you can, the difficult thing with the drug is you have to be sober for a week before you can get it. And you know, withdrawing from opioids, that first week, it A for everyone. I think that's as hard, if not harder than winning a marathon. If you can get through that, if you can have the worst illness, if you can have COVID for a week and know that you can get, make it go away just by taking another pill. And suffer through it, knowing that there's like something at the, that there's, it will get better, that your chemicals. I always had a rational view of it as like, I know that I have fucked up my brain chemicals by doing this. And it's going to take a while for them to reset in the way that I feel suicidal right now.

• 53:45Ken Rideout?

  This is going to dissipate. I know it will. I have blind faith. That faith gets tested when you wake up at three in the morning, sweating through the frigging sheets mattress. And then you're like 10 minutes later, you're freezing cold. It's just like, you're like, please God, make it stop. And you know, oh, you can make it stop whenever you're ready. That to me is like.

• 54:05Rich Roll?

  It's a brain fuck.

• 54:07Ken Rideout?

  Dude, that's what makes these drugs so scary and dangerous. And I think that it's like, in hindsight, it was so easy to just go in and get a prescription for drug, for painkillers. It was just, it's, it's, it's almost to the point where it's embarrassing. There should be more education around doctors saying like, yo, you can't prescribe this shit willy nilly to people. If someone needs pain medicine refills after the first like 30 days after surgery, like maybe reevaluate what's going on with them. Cause I had a massive shoulder surgery and it was like, a few days were incredibly painful, but eventually you're like, all right, now it's just uncomfortable. But it's not like, I need fentanyl.

• 54:44Rich Roll?

  Yeah. Yeah. Well, I think it is better. I hope it's better. I think doctors are, you know, they're, they have a better sense of this now than they did even a couple of years ago, but you know, there's millions of people addicted to these things, so.

• 54:58Ken Rideout?

  Millions.

• 54:58Rich Roll?

  Huge problem.

• 54:59Ken Rideout?

  Yeah, it's a big problem and it's unfortunately, I wish I never, I wish I had never even tried these drugs because I would be more than happy to not know what I don't know. Knowing that it's there is like.

• 55:10Rich Roll?

  Yeah, but you can look back on it as part of what made you who you are too. And now it puts you in a position where you're sitting on a microphone a couple of times a week, right? And you can share about this stuff and it's powerful because I think people out there, because so many people are out there suffering, it gives them hope that there is a possibility. Like not only did you get sober, you kind of completely recalibrated your life and you're doing things that, you know, I'm sure on some level, you probably didn't even believe that you were capable of.

• 55:40Ken Rideout?

  I can't believe I'm sitting here talking to you with such an honor like I, and I know it sounds crazy, but the fact that I'm like in these social circles with my friend Rob Moore and guys like John Joseph and I'm friendly with Joe Rogan, it doesn't even seem real to me. It's a, but at the same time, I'm like, there's another part of me that's like, yeah, of course I am because I'm trying to be a good person and do the right thing. I was telling Rob, someone sent me a message on DM and said, how did you build this network? And I was like, dude, if you think you're networking, you're already strike one, two and three. Who the fuck is networking? You're collecting relationships like assets? I said, I just, I'm just being myself. I couldn't tell you how I have relationships with certain people because I, I'm not trying to consciously collect relationships.

• 56:25Ken Rideout?

  And that, that to me is like, that word is awful. And LinkedIn, the same thing. People send a message on, LinkedIn is a perfect example. I have to, I have to say this because when people send a request to you on LinkedIn, it implies that we know each other. Cause if I am looking for a contact at AstraZeneca and I see, oh, Rich, you're connected with the CEO. Can you connect me with this dude? We're friends and I, and you're like, I don't even know that guy. I saw him one time at a coffee shop. I'm like, then why are you connected with him in a professional like LinkedIn? It drives me crazy. So when people send me messages, let's connect. I'm like, if you don't send a note that tells me why, like a random like.

• 57:03Rich Roll?

  Let's set up a call. Let me know what your week looks like. I'm like, I don't know you.

• 57:08Ken Rideout?

  Dude, a guy the other day sent me a DM and said, hey dude, I'm sure you get a lot of DMs. Here's my number. Give me a call real quick. I want to ask you something. I was like, I literally said, I was like, I have four kids, a wife and six jobs. I'm happy to respond to you on the DM, but like, I don't have time to talk to half my friends. I apologize, but I'm not gonna call you. Like it's, I try to be polite to people.

• 57:28Rich Roll?

  Right, but you responded.

• 57:30Ken Rideout?

  Yeah, yeah, I try to respond to everyone.

• 57:32Rich Roll?

  I don't even respond to that. It's preposterous.

• 57:42Rich Roll?

  Where does the rebirth into athleticism start to enter the picture here?

• 57:47Ken Rideout?

  Yeah, so, so when I, right around the time I started to really like take my sobriety serious and realize like that I was responsible for other people, I bought a bike. I was running and boxing for the New York Athletic Club and I literally had some like pain in my knees, something innocuous. And I was like, I'm gonna get a bike. I see all these people riding bikes. It looks like fun. And I bought a bike, literally I was like, mid-range bike, rode it for like two weeks, brought it back. I was like, give me the best bike in the house. I was like hook, line and sinker. I had everything. First ride, I had cut-off t-shirt, gym shorts. I did have bike shoes, but within like two weeks, I looked like I was ready to go on the tour. I was just all in.

• 58:27Rich Roll?

  You're that kind of guy, though. I'm not surprised. You're the guy, you're the guys who you've been riding five minutes, but you got the top of the line shit across the board.

• 58:37Ken Rideout?

  Yes, and that part of it, I always tell people when they show up with really nice bikes, I'm like, you better be fucking good riding that bike, because people are gonna come for that ass when they see you on your cul-de-sac with campy everything. I'm like, so I wouldn't say I had like the fancy European bike, but I had like, you know, the best specialized or felt bike. But I loved it. I rode this.

• 58:56Rich Roll?

  And you're doing the Central Park Loop and the kind of group ride that happens in the morning or the evening there?

• 59:02Ken Rideout?

  Yes, I didn't do a ton of group riding. I just didn't, I wasn't a huge fan of that like tight formation.

• 59:09Rich Roll?

  You're putting your life on the line.

• 59:10Ken Rideout?

  Hundred percent. You can get really hurt.

• 59:13Rich Roll?

  Cruising around rollerbladers and stuff like that. I mean, it's like, it's a derby, you know? People are going down constantly.

• 59:21Ken Rideout?

  Yeah, I've had multiple surgeries as a result of bike crashes. I crashed on Topanga Canyon. I was with, I thought I was with Rob, but I was with another friend coming down to Topanga. Screaming down and I looked back and it was just one of those things where you ever look back and then you look back around you're like, oh my God, I'm like, I lost my bearings. And now I'm not going to make this turn right on Topanga in this steep part. And I went down on my face, skidded, I literally stopped underneath the bumper of an oncoming car. Dude, fire trucks, I went in an ambulance, it was, my ankle was, bone was like, all the skin was gone, my ankle bone was exposed, my head was busted open.

• 59:57Rich Roll?

  Yeah, for people that don't know, I mean, Topanga, it has some pretty steep sections when you're, when you're descending it and there's no, there's really no shoulder for most of it. And it's pretty busy depending upon time of day.

• 1:00:08Ken Rideout?

  And I, and, and the funny thing is, soon as I jumped up, I'm burned up everywhere, my back, everything is, all my clothes are ripped off, like, for the most part, and I'm just bleeding everywhere, including my head. So I jump up and my, my, my partner, my business partner who was with me is the nicest guy, but he's like, very, um, he's not timid, but he's like, not as aggressive as me. So he's like, oh my God, oh my God. And I'm like, dude, how bad is my back? It's killing me. He's like, it's bad, it's bad. And that kind of snapped me out of it because I was like, dude, lie to me. Tell me it's not that bad, even if it is. So anyway, then the ambulance, fire trucks, everything came and, and took me out of there. But that was, um, yeah, I've had some serious wipeouts on my bike and my wife be like, why do you keep doing this? I'm like, that wasn't an anomaly, that's never gonna happen again.

• 1:00:51Rich Roll?

  But it all starts in New York City, riding in the park.

• 1:00:55Ken Rideout?

  And, and riding and running and I entered a duathlon in Central Park, like a two mile run, 12 mile bike, two mile run. And let's say I came in like 20th overall and very quickly I was like, oh my God, I didn't even know what I was doing, I bet you I can win this. And of course, my wife, who I was dating at the time was like, you really think so? She was kind of like, you know, somewhat interested, but not like obsessed with it like I was. And sure enough, I started to do little races, the North, North, North Fork Sprint Triathlon and doing little things here and there, picking up tons of tidbits here and there. But keep in mind, I didn't even know how to swim when I started in triathlon.

• 1:01:28Rich Roll?

  And you're how old at this point?

• 1:01:30Ken Rideout?

  I want to say early to mid thirties and I uh maybe maybe around thirty yeah around thirty to thirty five and um I I went to the New York Athletic Club where I was a member and I would I did not I knew how to swim if I fell off a boat you know I could go water skiing I but I wasn't a competitive swimmer so when I'd see guys like you swimming I'd be like oh how is this guy so much faster than me it would drive me crazy because it was so much technique because I was like I have good fitness how are they swimming circles around me even the guys who were in terrible shape

• 1:02:00Rich Roll?

  I got stories about swimming at the New York Athletic Club

• 1:02:03Ken Rideout?

  Yeah strange place

• 1:02:04Rich Roll?

  Back in the day

• 1:02:06Ken Rideout?

  So I would stand

• 1:02:06Rich Roll?

  It was a weird place

• 1:02:08Ken Rideout?

  Yeah very but I would stand there and um I'd see someone like you or Olympic swimmers like I mean you name it I I've seen everyone there Michael Phelps everyone and I would see someone who looked good and I'm like hey buddy do me a favor will you watch me swim down and back and tell me what I'm doing wrong most people if you ask for help are like yeah all right go for it and you know you pick up a tidbit here and there then you see the guy the next day I'm like hey what about when I'm doing this do I like am I doing this right so when people will send me DMs and be like how do I do this how do I do that I'm like brother if you really want to do this you don't need to ask anyone else everything's available you can find YouTube you like if you really want to do it you don't need me to tell you you need to just do it get in the pool and

• 1:02:49Ken Rideout?

  start swimming it's like running I just started running I didn't have a game plan I was running ten miles a day and I started to recognize that I have good fitness I bet I can win some raises but back to the swim and I I was just trying so hard and I think that the people who were the regular swimmers there at the time that I was swimming like they respected it they were like oh this guy wants to get better and then people want to help you if you want to help yourselves just like rehab or or recovery if you if you see someone who's trying hard and looks like they need help but they're putting in the work and not asking for anything people started to try to help me and and and very quickly I got strong enough in the swim that I could at least

• 1:03:30Ken Rideout?

  Not be blown out the back. So when I got on the bike in a non-drafting race, I could make up some work and then do work on the run. And, um, but really, I wish I, if I could swim a little bit better and we can progress into it. But I eventually came in like sixth or seventh at Ironman Wisconsin overall, same at Ironman 70.3 in Hano in Kona, the half Ironman. Um, and, and every time I was like, oh, all the time I lost in the swim is the difference between winning the overall and losing.

• 1:03:59Rich Roll?

  Right. Swimming's tough though, because if you don't learn it at a young age, you can get up to a certain point, but there's just a certain, it's like learning a language when you're young, you know, it just becomes so much harder when you're older.

• 1:04:10Ken Rideout?

  And the guys who are just, they have that technique. It's like the fitness is almost secondary. If you have that efficient, smooth technique in the pool, it's beautiful. And you can do countless hours of work without damaging your body.

• 1:04:22Rich Roll?

  Well, it's all about efficiency and making the water work for you. And people that don't kind of have that level of technique are fighting the water all the time. So they're expending, not only are they going way slower, they're expending twice the amount of energy. And in an Ironman, you just want to be in contact with, you know, the group or whatever. So it's about holding back as much as it is anything else. So when you're getting out of the water, you're fighting to be part of that. And you're, you're like tapped to some level. And those guys are like, I'm good to go on the bike now, you know?

• 1:04:54Ken Rideout?

  No, that's exactly right. And inevitably what would happen is I'd get on the bike and start trying to make it all up in the first like 40 miles. And by the time I got off the bike, I was like, I'm on death's door.

• 1:05:04Rich Roll?

  And you're doing this without any coaching or really any program? Like you're just going out, I'm going to run 10 miles every day. Like that's not exactly like the best strategy for getting these goals done, right? Are you going online and saying, well, here's how you prepare for an Ironman? You should look like this. Or are you just trying to do it your, do it the Ken way?

• 1:05:23Ken Rideout?

  I, a combination of both, but I would argue that with the running, the 10 miles a day, I'd argue that that does work. How many people are actually going to do that? If you do that, like that's all I did. And I, and I started running really fast.

• 1:05:34Rich Roll?

  No days off?

• 1:05:36Ken Rideout?

  The only time, when I lived out here, the only time I would take a day off was to be to do like a 50 to 100 mile bike ride with Rob Moore. So I'd do my long run on Saturday and a long bike ride on Sunday. Typically, or vice versa, but with the Ironman, I eventually hired Jimmy Ricatello, who's the head ref at Ironman. And a really nice guy, and he helped me really get ready. He was a legend. Yeah. So in 2012, so I'm doing all these little races and I'm getting better and I'm learning things here and there and I'm trying to pick up things from everyone. And in 2012, I qualified for Kona at Ironman New York. And to me, I had achieved like a dream that I didn't have it for years. But when I saw Ironman on TV, I was like, that is unbelievable. Wow, that looks so compelling.

• 1:06:20Ken Rideout?

  Impossible to do, but wow, if those people can do it, why can't I? Why not me? And, you know, I had always had the kind of an attitude of like, I don't know that I can do that, what these other people are doing. And that was really the first time where I was like, no, dude, you're only limited by what you think. Like, if those people can do it, you can do this. And I convinced myself I could do it and I did. And I qualified with a roll down spot in New York, you know, so. For those who don't know, there's a certain amount of age group spots at each Ironman race and Ironman New York, because it was the inaugural race, they had a couple of extra spots. And, and, and let's say there's 10 spots and, and if someone of the 10 doesn't take their spot, it rolls to the next, to the 11th place finisher in that age group.

• 1:07:00Ken Rideout?

  So I got a roll down spot in New York and I qualified and I was like, yes, we're going to Hawaii. I had two little kids. My, they were babies and me and my wife and we went and rented a house on Alihi Drive. I was like, I'm going to the Olympics. It was. I was like, man, I did it. I was on a high and I get there and it's just like you would imagine the like, my equivalent of the Olympic Village. It was like all the like triathlon nerds, myself included, were all like, everyone's running around happy to be there. You know, it's like such a. Such a culty place.

• 1:07:28Rich Roll?

  And everyone's crazy fit.

• 1:07:30Ken Rideout?

  Crazy.

• 1:07:30Rich Roll?

  Everywhere you look, you're like, wow, that guy looks a lot fitter than I look.

• 1:07:34Ken Rideout?

  Compression, soaks, veins everywhere. So we get there and, you know, same thing, swim, I suffer through it, get on the bike, start working way too hard, full of irrational exuberance. And sure enough, I get off the bike and I'm like, oh my God, I'm crippled. I can barely move. And my wife's at like mile three on a Lehi drive and I'm like hobbling, running down. And I mean, I feel terrible. And I see her and she's videotaping and it's almost like with tears in my eyes. I'm giving her the like throat cut sign, like cut, cut, you know, like a director, like, don't, don't film me. And as soon as I got there, I'm like, I can't do it. I'm just gonna like, I'm stepping off. I'm just, I'm gonna walk back to the transition area. I'm just not in a, I'm not in a good spot physically.

• 1:08:15Ken Rideout?

  And I almost had this mentality of like, like, almost like a professional, like, well, if I'm not gonna be in the money, like, I told myself every bullshit story under the sun to justify quitting. Well, I'm not, I'm not gonna be in the top of my age group. I'm not gonna do this. I'm not gonna like, I basically was just a quitter. I just packed it in like a, like a, oh, I'm so disgusted. Even in hindsight, thinking about it now makes me mad. But I did, I just quit and I, and I had no excuse other than I was hurting. And I was, it was such a letdown. I went from the highest high in terms of like my personal like satisfaction with myself to like, really depressed.

• 1:08:55Ken Rideout?

  Like, oh man, I am, I just felt so ashamed isn't the right word, but it was almost like a level of shame internally. And, and my wife had been super supportive of me training for this, cause you know, it takes like a ton of time.

• 1:09:06Rich Roll?

  Unbelievable amount of time.

• 1:09:07Ken Rideout?

  I got two babies. She's like, what are you doing?

• 1:09:09Rich Roll?

  Right. Like after this, we're done, right?

• 1:09:11Ken Rideout?

  Yeah, exactly. And I was like, yeah, we had like a deal. She had like written up a contract, like, you agree that I'll support you.

• 1:09:18Rich Roll?

  She wrote a contract?

• 1:09:20Ken Rideout?

  I think she wrote it for the second one. Good for her. Yeah, she was like, but my, my wife is like, when it comes to like being a good partner and um, and a mom, she's world class. She's the world record holder. She's as good as anyone I've ever seen. She's, she knows, she's, she's awesome. Mm-hmm. And she was supportive, just like I was her fifth child, which is like what it feels like most of the time. Cause uh, you know, she's the one that has like the rational brain when I get irrational and emotional. So I said afterwards, we're sitting there and I'm like so depressed, I might even have been crying and I was, she was, and I was like, I just, I know I can do better than that. She's like, if you, if it's that important, do it next year, just do it again. You know, now you have to qualify again. It's not just like, oh, just sign up next year.

• 1:10:02Ken Rideout?

  So I was like, really? And she was like, if that, if it's that important, you do it. And I was like, I'm gonna, I'm gonna do everything in my power to win. And um, I qualified at Ironman, either Whistler or Wisconsin, Whistler. And um, went back and did like a nine thirty-nine and I was so proud of myself. I was like, you know, that's a respectable time. Yeah. I would have liked to have been under nine thirty, but I was like, yes, I did it. And um, yeah, she supported everything through that and uh. And then she said, uh, let me draw your attention to section six, clause A. Yeah, yep, pretty much. And then I uh, and then, you know, like any um addict, I couldn't stop this uh,

• 1:10:43Ken Rideout?

  addiction to endurance sports and triathlon. And I did go back to Kona one more time in two thousand and sixteen, when I moved out here, I qualified at Wisconsin, which is the one that I almost, I could have won that if I had swam. I did, we had had our fourth child and I just was like, I'm not even gonna swim. I'm not gonna swim. To save five minutes is gonna take me like two hours, you know, three times a week. I'm just, I'll just take the one ten, which is what I swam. And then I rode like a four fifty-eight and ran a three fifteen and finished like seventh overall, one my age group and maybe sixth. And I went back to Kona in 16 and I was like, oh, I'm gonna get him. I'm gonna like win my age group or be in the money in 16. And I got pneumonia like three weeks before the race and um went back and walked the entire marathon.

• 1:11:26Ken Rideout?

  But after having quit in 13 and then gone back there, I was like, I know I'm not coming back here. So I got on the run and I was just suffering. I was like, that's okay, I'll just walk. I'm not gonna like disrespect myself or the race. And I just walked and I made it like a click under 11. Right or either right over under 11 hours, but right before the sun went down. I was like, oh, thank God, I'm racing the sun.

• 1:11:47Rich Roll?

  Yeah, yeah.

• 1:11:47Ken Rideout?

  But uh, yeah, and it was around that time that I started to just do more running just because of the lack of time.

• 1:11:53Rich Roll?

  Yeah.

• 1:11:54Ken Rideout?

  And that's when I started the 10 miles every day around 2016.

• 1:11:57Rich Roll?

  Right. And you did that for quite a while and started racking up wins before hiring Mario Frayole to coach you, right? And he's the one who kind of took you from the 233 range to the 228.

• 1:12:10Ken Rideout?

  Yep. And I started, um, that's when I started doing the 10 miles a day and just like getting better through volume. And I won the first race that I won that was like, I thought, oh, man, I might be, I might be pretty good at this. I won the Malibu half marathon, which is cool that Rob has won it now. Cause I won it like, I won it two or three times and the one time I didn't win it. Uh, an Eritrean former Olympian, 5K Olympian from Eritrea, who's a guy who now coaches, I think, cross country. Cal Berkeley, he beat me by a couple of minutes.

• 1:12:41Rich Roll?

  Uh huh.

• 1:12:42Ken Rideout?

  And uh, the funny thing is right before the race started, I had won it the year before in like 117, which isn't very fast. But you can only beat the people who are there. So that guy stand there and as soon as I see him warming up, my wife and kids never come to races, but they came to this one. And I see the guy warming up and I'm like, oh, for Christ sakes, this is the year that the African pro shows up.

• 1:13:01Rich Roll?

  Right.

• 1:13:02Ken Rideout?

  Dang it. So the kid, he stand there, he was a coach and there was a, uh, maybe like a 20 something year old kid standing with him. And the, the younger kid says to him like, yeah, you see the time that won here last year was terrible. Like you're gonna definitely win this. And I'm standing right behind him with number one on it. And I go, hey, all I can do is beat the people who show up. Let's see how it goes today. Now they both were like legitimate runners. This kid ran at Cal Berkeley.

• 1:13:24Rich Roll?

  Yeah.

• 1:13:25Ken Rideout?

  And uh, but I was like, yo, not at the start line. I'm like on edge, like I'm like, I'm not the one to clown. So I was like, uh, yo, we'll see, we'll see how, we'll see how fast you are when we start. Now I'm basically saying like, I'm gonna kill you.

• 1:13:38Rich Roll?

  Uh huh.

• 1:13:39Ken Rideout?

  And it takes off and they are like running five minute flat and they're off. And I'm like, damn it, I want to kill this kid. The Olympian, he didn't say anything. He was just, I mean, he was on another level. I couldn't have beat him on my best day. But as we, at that turnaround, I was like a minute down to the, um, to the young guy. And as I like just ran right past him. And, uh, I forget what he said at the beginning. He said something like, oh, I don't even have a singlet on. I have a T-shirt or something like me, almost already making excuses. So after he finished, I was like, hey, man, good race. Next time wear the right attire and you might've had me. But I couldn't help myself but to get one shot in him. I'm like, yeah, okay, you got a T-shirt on that. Slow you down.

• 1:14:16Rich Roll?

  Oh my God.

• 1:14:17Ken Rideout?

  But I was like, man, this guy doesn't know. He's like standing in front of me, like talking crap about me. I was like, man, come on, I'm too insecure to let that go.

• 1:14:24Rich Roll?

  See, this is why I didn't go out and train with you.

• 1:14:30Rich Roll?

  I'm interested in, in what you learned working with Riccatello and with Mario. Because I think what's interesting about your story is you got really far just on grit and determination and persistence, like here's what I'm doing, in kind of a bullheaded way, like, you know, I don't need to really look and see what else anybody's doing. I'm just, I know me and I can figure this out. But in order to really level up and achieve your goals, you did reach that point where you're like, hey, I need to bring somebody in, right? So, so, and I think there's a lot of people who are, who are watching or listening to this, who can relate to that. Like I can't afford a coach or, you know, I have a job and like I just go out and do what I can do every day.

• 1:15:10Rich Roll?

  So I think it would be cool to, to share a little bit about like what you've learned through those relationships that could be helpful to the amateur athletes out there.

• 1:15:19Ken Rideout?

  I would say this, like if you're spending time and effort doing this stuff, I would argue that you can't afford not to have a coach. Because everyone has so much time and money and effort invested into their results, if it, if it's something important to them. If you're just doing weekend races and trying to finish, like maybe you don't need a coach. But if you want to be competitive, even if it's with yourself.

• 1:15:36Rich Roll?

  Your approach, you're an amateur, but you, you train like a professional and you treat it like any professional athlete would.

• 1:15:42Ken Rideout?

  Oh, if my wife tells me like, what are you doing? We're going ski, we were in Aspen, we're skiing. I'm like, yeah, I gotta work first. She's like, what do you mean? I'm well, this is my job. Like I, this is part of who I am. Like I, I need this to feel, I need this to start my day. And, um, I would say about a coach is like if it's really important to you and it could be just you racing yourself, maybe you want to break 330, whatever it is, if you've, if you think that, you know, you, you've invested this kind of time and effort to hire a coach, I mean, a coach isn't super expensive and there's tons of online assets, but one of the things that I found in working with real coaches and guys who are very knowledgeable, especially like Jimmy Ricatello, when it comes to triathlon and cycling, I mean, his son is like now a pro tour rider, I think he might even be on a pro tour team in Europe, but he was,

• 1:16:25Ken Rideout?

  he gave me, Jimmy gave me my introduction to like real structure and real accountability more than anything. It's like you could, I could look at online plans, but if there's no one kind of monitoring it, even if it's just, not that I was trying to impress someone, but just knowing that

• 1:16:41Rich Roll?

  He's gonna look at it.

• 1:16:42Ken Rideout?

  I viewed

• 1:16:43Rich Roll?

  You don't want to let him down.

• 1:16:44Ken Rideout?

  I viewed Mario and Jimmy and I talked to Mario all the time, Jimmy, I haven't, I talked occasionally, but not since I'm not doing triathlon, much less, but when I talked to Mario, I tell him, dude, we're partners, we're teammates, like I'm representing you when I'm out there, I believe this, I believe I only have one teammate in running, it's me and you, you know, with Mario, and I'm like, you write the formula, you write the prescription and I'm gonna take the medicine. So he gives structure and like you said, I was running 10 miles a day and when I got to 233, I couldn't break through, I, I went back to CIM and ran like 235, well, but you know, running a 110 in the first half probably wasn't very conducive to running fast for the second half, considering that was like

• 1:17:25Ken Rideout?

  three minutes faster than my half marathon PR, the year after I ran 228, I was like, oh, I bet I can run 226, so I ran a 110 first half and like it blew myself out of the water with three or four miles to go. But when it comes to the running with Mario, it's like he writes the plan and I follow it like a, like a roadmap, meaning if there's traffic in one, on one direction, I might take a slightly different, but ultimately I'm trying to get to the same place. So the coaching is like a rough outline, it's not an exact science. Like today, there was a track workout, but obviously I was, got in late, didn't sleep great, so I said, I'm gonna do that tomorrow on the beach and I just make changes here and there, but it's literally like those kind of things, we don't even have to talk about because he'll, he sees everything that I'm doing in real time and everyone can, I

• 1:18:10Ken Rideout?

  post everything on Strava. And, and part of that is for accountability too, it's like This is what I do and I get a lot out of it. That accountability like provides me with structure and and a sense of accomplishment to start the day. It's like the military guy who was given the commencement address and he said, start the day by making your bed. You have one win already. That's how I view the run is. If nothing else happens today, I've taken care of my most important asset, my mental and physical health. It's more important to me than everything. It has to be. I can't be my best self with my children, my wife, and I'm useless to anyone if I'm not healthy.

• 1:18:51Ken Rideout?

  And part of this exercise every day in this 10 mile therapy is as much mental health as it is physical. It makes me feel good. It is my antidepressant. When I go through periods of not being able to do it, like when I had the shoulder surgery, like I had a few days of like real depression. Like, I don't want to say suicidal thoughts, but certainly like suicidal ideation of like, would I be better off just not doing this? Like, do I want to be here? And I know when I say it, it sounds irrational and I reflect on it. It sounds crazy, but I can't deny that these are the thoughts that enter my head when I'm not holding myself accountable and maybe it's a blessing, maybe it's a curse, but this is just the reality of my life.

• 1:19:35Ken Rideout?

  Is I just maybe from the mistakes I've made and the things that I've been through, like this is just what I need. And I'm not opposed to hearing like professional takes on like, you should try this, this, this. I'm not close minded, but right now that's my state of mind is I need this.

• 1:19:52Rich Roll?

  Yeah. In hearing you share that, I certainly relate to that deeply. But at the same time, I also can't help but think like you're holding on to it so tightly, right? Like on some level, like is it self flatulation? Like, like you're doing penance? Like you're punishing yourself because there's a sense of undeservedness or you're not worthy until or unless you get that in. And there's got to be moments when those priorities come into conflict, when you know, your workout is at odds with, you know, something that you know, you need to do with your kids and you have to make those decisions around where you're going to invest your time and your energy.

• 1:20:33Ken Rideout?

  When there's real conflict, I will say like I will, I'll make the amendments and adjustments on the fly. Like if someone had an eight o'clock Little League game and it was like, You know, there's so many kids we divide in Congress, but if there is one that we all have to be at, like I'll go to the game and then maybe I'll run home or I'll do something, but I'll always like

• 1:20:51Rich Roll?

  Find a way to work it in.

• 1:20:52Ken Rideout?

  I try to find that balance, but you're not far off there in that. In your assessment there, there's definitely like some things that I know that I need to address. I don't profess to be, have all the answers or to be doing everything right. I know that there's things I need to improve on.

• 1:21:09Rich Roll?

  I think there's a gift in there if you're willing to explore it. Like I'm not a professional. I don't know what it's about. I mean, perhaps it has something to do with, you know, a sense of like guilt, like you have this amazing life and this is just the payment that you have to make on a daily basis to earn or deserve like the life that you have. Like, you know, I don't know. And there's certainly nothing wrong with being competitive and hard driving and, you know, you're accomplishing all of these things and then you share it so openly with people and that's of service. And so I don't mean to malign any of it. I just think it's interesting and curious. And I think there is like, you know, some, some kind of like growth opportunity for you there.

• 1:21:50Ken Rideout?

  You're not maligning me and I don't feel at all uncomfortable. I think part of the benefit of doing something like this is being able to share my truth and my reality with people and hoping that somehow I can improve the quality of my own life through sharing my stories. And you're a hundred percent right. I know that this isn't necessarily like the greatest success story in history. I know that there's things that I could and should be doing better. And it's a constant struggle, but compared to where I've been and what I've been through, right now, this is what's keeping me on like the path I'm on. But I would fully agree with you that there is like work to be done here that I don't, I shouldn't have to feel like I have to do this and

• 1:22:34Rich Roll?

  Right. Like what happens if suddenly something happens and you can't do this? Like how are you going to be okay with yourself? How are you going to find meaning and purpose and be happy and productive?

• 1:22:44Ken Rideout?

  Be an ultra swimmer?

• 1:22:45Rich Roll?

  Yeah.

• 1:22:46Ken Rideout?

  Find another challenge.

• 1:22:50Rich Roll?

  And that brings up the, that kind of other piece here. And you mentioned it earlier, like this addiction to endurance sports. And I know as somebody who's in recovery, like I get it a lot. Like, oh, you just, you transferred one addiction for the other. And I don't know how you answer that question. I'm sure it gets thrown in your direction. Like, you know, I have to Think about that. And I think on some level, I have to recognize that there's truth in that. Like, I want to say, no, you don't understand addiction was trying to destroy my life. These efforts make my life better. They're completely different, but of course, there's similarities and overlap. And if I'm not rigorous, that relationship can get out of whack. And the other things, the other buckets in my life that are important will suffer.

• 1:23:35Rich Roll?

  And so I'm always like trying to like, you know, maintain like a healthy relationship with all of these things. And I'm not always successful at that, but like, how do you think about that? As somebody who's in recovery and is so driven and so ambitious in these goals that you're seeking, you know, at age 51?

• 1:23:55Ken Rideout?

  You hit the nail right on the head. And as you're saying that, I'm reflecting on my own decisions and wondering if, if in fact that there's a lot more deep work that needs to be done. And this endurance stuff in essence is prolonging me from having to do the other work that I need to do to kind of deal with the psychological and emotional issues that I have. Because I don't, like I said, I don't profess to have all the answers, but, and yeah, I, I've convinced myself that this is the best. This is, it's all going right. But in my mind, I know that there's things that can be better, for sure. And I think that really the person who probably takes the most amount of shit for this is probably my wife.

• 1:24:37Ken Rideout?

  Because, and it's, you know, it makes me emotional to even think about because she is my biggest advocate and supporter. And at times, she's getting the worst of me. And it's, you know, something that for sure, these, again, these conversations are all part of the process and part of the therapy. And I hope that if someone's listening to this and relates to anything and that they're getting that like, life isn't Instagram. Like this is, that's just a small.

• 1:25:06Ken Rideout?

  Snapshot of like a reality and you know, I think that more so than anyone is my wife probably recognizes that is like, yo, this, there's a lot of things you can be doing better.

• 1:25:16Rich Roll?

  Hmm. The good news is endurance sports is a pretty great vehicle for personal growth and all that time spent alone in reflection with an elevated heart rate. I just know for myself is critical to my own mental health, but also gives me that ability to kind of like free associate and, and get a little bit more objective on the things that I'm running away from because it can be, you know, an out of whack relationship with endurance sports. That teacher then becomes the escape hatch, right? Like you can use it to run away from a bunch of stuff and you know, shroud yourself, you know, with a, with a victory lap or whatever and say, this is great and I love it. But when you're really honest

• 1:26:01Rich Roll?

  with yourself, you're like, yeah, but it's easier for me to go out and crush it than it is to deal with this other thing that I really don't want to deal with.

• 1:26:08Ken Rideout?

  I will tell you that.

• 1:26:08Rich Roll?

  And that's true of all of us because growth never ends, right? There's always more layers.

• 1:26:13Ken Rideout?

  I'll say this, that, um, yeah, that's the, uh, you know, you, you hit on so many important topics, but on one hand, like the endurance sports and the relationships I've built have basically given me the life I have. Like I can't stress to the listeners enough, like you have to surround yourself with people that you admire and respect. And this finding endurance sports and having success there was a way for me to connect with like-minded people that have changed my life. My best friends in the world are from endurance sports. I, I have so many deep relationship with people that I love that I wouldn't know from doing that if I hadn't been involved in this. But you're right, there is a certain level of, um, escape by, by almost putting off work that I know needs to be done, but

• 1:26:58Ken Rideout?

  I'm using the, the endurance as like a bit of an escape or a, or a distraction from things that need to be addressed. So. Like I said, this all part of the therapy for me is sharing these stories and being so open and honest, even at like my own detriment. If my wife will be like, I can't believe you shared all that. I'm like, who even cares? I'm like, hopefully someone gets something out of it. But you know, in recovery, they'll tell you, you're only as sick as the secrets.

• 1:27:23Rich Roll?

  Right. And I appreciate the honesty. Yeah. And you got four kids at home, right? And you're, you're, you got a daughter who you adopted from Ethiopia, and then you got four boy, three boys, right?

• 1:27:36Ken Rideout?

  Yeah, we adopted my daughter. She was four months old, newborn baby in Addis Ababa. When we, when my wife and I initially got married, like my wife, I married my wife because I knew that she wanted the same things I wanted. And I knew that she would give me the family and the household that I didn't have as a kid, that I so desperately desired. A safe, stable house with loving parents. It was just my idea of, you know, heaven. I was like, this is what life is. And, you know, I will say this, and I say to people all the time, like marriages and relationships take work. It's, it's, you start out dating

• 1:28:18Ken Rideout?

  your best friend, and then you introduce children into the mix. It's like, you are dating someone, your best friends, you're doing all this cool stuff. And then all of a sudden, you're running a deadly serious business together. Someone's got to get up with the kids. Someone's got to feed the kids. Who's going to go food shopping? And all of a sudden, it's like, yo, I can't stand you. You're the worst team player ever. I don't have that. My wife is the best business partner ever. And I might be one of the worst because I just, I'm so, I have so many things going on. But I knew this was her dream job. She wanted to be a wife and a mom, and she's the best at it. And when we first got married, we were like, okay, let's start a family right away, which we were both down with. I think I was 37, she was 34. We got married, we adopted my daughter at

• 1:29:03Ken Rideout?

  I wanna say I was about forty and she was thirty seven. And we're trying to have kids and you know, it's interesting because you spend your whole life hoping someone doesn't get pregnant. And now you're like, alright, it's go time. We're definitely gonna get pregnant right away. One year, two years, three, uh, one in vitro, two in vitro, seven in vitro cycles, three miscarriages. My poor wife, it was like everything she ever wanted and it wasn't happening. In my mind, I'm like, it's gonna happen, don't worry about it. I really believed it would happen, but she was inconsolable at times like. But we, when I first met her, I had told her, I wanna adopt kids, as many as I can afford. Because having been through what I had been through and then the life of chaos and anxiety

• 1:29:47Ken Rideout?

  that I had as a kid, I was never comfortable, never. I never felt on Christmas I'd be concerned about something. It would just, there was always something like uneasy going on at this friggin' nut house that I lived in. So when I met my wife, I said, if I can change someone's life, I desperately feel like it's my obligation to make a difference for someone, as many as I can afford. And she was like, I wanna adopt kids too. So the minute we got married, we started the adoption process. A lot of times people are like, oh, did you adopt because you couldn't have kids? No, we adopted, we, we, we've tried to adopt many more. We've been like, adoption is such a dirty business. But um, we started the process and sure enough, we get a call one day that we, we were approved for um, two.

• 1:30:28Ken Rideout?

  And we got a call, say, hey, we have a newborn daughter, um, she, um, youngest we've ever seen at the orphanage in uh, Owasa and just south of Addis Ababa. And they, you know, when you do that, they give you a health report and all this stuff. And I just remember thinking, they sent the picture? And they're like, okay, we're gonna give you the health report. And I said, I don't need a health report. And they're like, no, no, you gotta make sure she's. I said, if you had a baby and she had something wrong with her, what are you gonna do? Like, that's your baby. I was like, as soon as you told, I was like, I don't, and she didn't, she, she was severely malnourished, had jardia, was like, super malnourished and, and, and like distended belly, weighed like seven pounds, I think at four months, really small. And um, so we go over there to get her. And my wife lived there for two months with custody of her.

• 1:31:12Ken Rideout?

  It was crazy, because at the time when we were there, I was like, this is so hard. We get into the hotel, into the guest house, and uh, in Addis Ababa. And they had big hotels, but they didn't want us to stay here, because they didn't want too much attention on these white families adopting black kids and, you know, like, they just didn't want. They didn't want to draw attention to the fact that we were there two months with this newborn baby. For whatever reason, so they say stay in this guest house and it to say it was rough would be an understatement. Every night the lights would go out, they'd fire up this big diesel truck engine that was mounted on a block of cement in the courtyard to fire up the lights. We get in there and I go to lay on the bed now, long flight through Germany into Ethiopia.

• 1:31:53Ken Rideout?

  And I lay down in the bed, I'm like, what the hell? Our bed is missing a mattress, there's just a box spring. And I go down, now keep in mind, she's there for two months and we just got there and I'm like, oh my god. I'm thinking, I'm so happy I'm leaving in a week, this is so rough. And I got on, I'm like, hey, the mattress, it doesn't have a mattress, it's just a box spring. And they're like, no, no, that's what you have. And they gave us like an egg crate thing like you put in college. Right. So, but my wife, to her credit, she was like, ah, it's fine, we're gonna be fine. I go, it's two months, you're gonna sleep on a hardwood floor for two months? This is crazy, we gotta figure something out. But just shows you like the different mentality. So we go and get custody of her and even this is funny, we go down to see them in the orphanage in this village in Owasa and they say, hey,

• 1:32:36Ken Rideout?

  here, okay, we'll meet the baby, we're gonna go back to this nice resort that was beautiful on a lake in Owasa and they said tomorrow we're gonna do sightseeing and stuff. I said, the babies are at the orphanage, right? And they're like, yeah. And I said, why the hell would I want to go sightseeing when I can spend time with my new daughter? I'm like, I'll sit in that room all day, so and then, and then of course, all the people we were with, super nice people but not very aggressive and they were like, thank god you said that. I'm like, I can't believe all these people thought the same thing, but no one was gonna say anything, we're just gonna let someone else dictate the day. So we go, we do that, we go back up to Addis and we go to court on the last day I'm there before I have to go back to work. So I was there for a week and then I went back a month later for another week and my wife was there continuously with custody.

• 1:33:17Ken Rideout?

  You had the option of leaving her in the orphanage, going home and then coming back when the process was done. But I was saying like, if I had a baby and someone said, I'm gonna send your baby to Ethiopia for two months, I'd be like, no. So, we get in front of the judge, the Muslim woman and the lawyer said, don't say anything to the judge, just let her do her thing. And I was like, okay, cool. And I said, by the way, when are the babies coming? They're like, ah, next week. I said, but after today, they're ours, right? Like, it's, it's all. He's like, yeah, yeah, but we got to organize a car. I said, I'll pay for a car tomorrow to take everyone up, whatever it costs. And they're like, nah, we can't do that. And I'm like, why? And they're like, well, it's just not the way it goes. So, and she, and my daughter was sick and there was doctor and artist that could see her.

• 1:33:59Ken Rideout?

  So the judge says, um, okay, yep, it's all done. And I said, ah, judge, excuse me. Uh, and I told her, I said, the babies are down there. They said that they can bring them to us, but they're not going to bring them till next week till like they have like, organized something else. I said, I'm happy to pay all the costs to get all the babies brought up. And the judge looked at the lawyer and goes, have all those babies brought up tomorrow. When we came out, the people that went through the process with her, my wife always says, it was like they wanted to have a parade for me. They were like, oh my God, thank God you spoke up. But I only tell that story because it's like, it's, it's like a metaphor for life is like, at some point you don't be afraid to like speak up and ask the questions and the worst thing someone could say is no. And then you're in the same position you're in right now.

• 1:34:41Ken Rideout?

  So, um, yeah, we adopted her. I, I came home when, and when I, when we were in that resort, we were down in this beautiful resort for ourselves, hanging out. When I went back to New York, my wife's like, oh, I don't feel that good. I think I might be pregnant. And I'm like, nah. It's, we've tried so many times, like, so she's like, well, bring a pregnancy. This is how far along where I said, I'm not even going to spend the money on those stupid things. It's a waste of money. If you're pregnant, we'll find out in nine months. So anyway, I brought the test in. Sure enough, she was pregnant. But again, we'd been pregnant multiple times. And sure enough, she came home two months later on, like a week before Christmas and was pregnant with our son, who happened to be due on my daughter's first birthday. And he came like three weeks early. And, um, then every two years, for the next four years, we got, we must have that same fertility window.

• 1:35:24Ken Rideout?

  All the kids' birthdays are within like five weeks. And are your kids into all this stuff that you do? From Instagram, it looks like you put them through your, through their paces a little bit, but they're into it. I don't know if all of them are, but. Again, it's not, I'm not consciously trying to build a, um, a narrative on, on Instagram, but I post the pictures that I find entertaining, which happen to be sports. But they're, they have a very healthy relationship with sports. They all play like, one plays Little League, one plays lacrosse. Um, the youngest one inevitably is like just so good at everything. He's so aggressive. He's also the one that comes into me and like, dad, can you give me a mohawk? And I'm like. Can he have a mohawk? And she's like, I mean, he can, they can get a like a buzz cut for the summer. And I was like, all right, come on, buddy. And I'd shave his head and I accidentally

• 1:36:09Ken Rideout?

  put the guide on like zero. And now his head is shaved down to the skin with a mohawk. And he's like, I love it. You know, he's also the one that when his tooth is loose, instead of like dealing with it and like hoping it falls out, he just comes over like, Dad, can you pull my tooth out?

• 1:36:22Rich Roll?

  Mm hmm.

• 1:36:23Ken Rideout?

  And I'm always like, I mean, they're all

• 1:36:24Rich Roll?

  Yeah, that's a chip off the old block situation.

• 1:36:27Ken Rideout?

  In this kid, but he is the nicest, most comfortable in his own skin. And the challenging part of being a parent is they're all so wildly different and they all need different, totally different relationships and approaches with me. My oldest son, he really needs my attention. He needs to feel, he needs positive reinforcement. The little one, I could be like, oh, come on, poopy pants. Don't strike out this time to start the game. And he'll laugh it off. Be like, I'm not striking out. If I said that to the older one, it would be like, what are you doing? You're gonna damage him for life. So that part of it's been, um, that's, I think, one of the most challenging things about being a parent is recognizing that they're all so different and they're never what you expect them to be, you know?

• 1:37:08Rich Roll?

  They, uh, they don't come, uh, from you. They come through you.

• 1:37:13Ken Rideout?

  Hundred percent.

• 1:37:13Rich Roll?

  And you realize, I've got, I've got for myself. And you just realize that, of course, nurture is super important, but they kind of are who they are when they come out. And you put the guardrails up and you try to point them in the right direction and, you know, push them from behind and all of that. But you can't make them something they're not from day one.

• 1:37:32Ken Rideout?

  Hundred percent. And the one thing I will say is like, the people who know your character better than anyone are your kids. I'm 100% authentic in myself in front of my kids, for better or worse. And I think about it all the time when I make mistakes or I do something good. I'm like, they're never gonna forget these first experiences. And it's like, especially when I do something wrong, it weighs on me like, I get down on myself if I'm not being perfect with them and I make a lot of mistakes. You know, it's hard because I I tend to talk to them like they're my friends, you know. So we're watching sports or something and I curse and the crazy thing is they don't curse, but I'm like talking to them like I talk to my guy friends and my wife be like, dude,

• 1:38:14Ken Rideout?

  what are you doing? I'm like, oh, I forget that I've got to like watch how I how I the words I use in front of them and it's but to their credit and to my wife's credit, they never ever emulate that bad behavior. I think that they take stock of it and they're aware of it, like they use a lot of bad words and I say to them.

• 1:38:32Rich Roll?

  We're not gonna be like that.

• 1:38:33Ken Rideout?

  I say to them.

• 1:38:34Rich Roll?

  Every kid wants to move a little bit in a different direction.

• 1:38:37Ken Rideout?

  But I always tell them, I'm like, listen, using bad words just shows that you have a bad command of the language and you're lazy. And they're like, but you do it. I said, yes, and I'm not perfect and these are the things I'm doing wrong. This is laziness. You shouldn't use those words. If you're really smart, you wouldn't use those words. You'd have other words to use instead. So I'm aware I'm aware of all my shortcomings.

• 1:38:58Rich Roll?

  It's gotta be, I mean, you're an intense dude and you're out like training like a maniac and you're winning these races. So, you know, on one level, like the kids see that, they see, you know, hard work leads to results. They see the success. I'm sure they, you know, admire and respect you for that. The flip side of that, of course, is also that it's like it's intimidating. Like, oh, if I don't, if I can't achieve like that, then, you know, you know, why even try?

• 1:39:28Ken Rideout?

  Yes, and and I would say that that is the case with my daughter. She is like not the most athletic person in the world and she'll say to me like, I hate that we have a sports family. And I'm like, tense, you don't even have to be good. The only thing that we ask for is effort. You don't have to do sports. You can do swimming. You can be an artist. You want to take sewing classes, be a designer. You can do anything, but you have to do something and you have to have some passion and we'll keep trying things until you find something you're passionate about. But just going through life and not having interest is like not cool. It'd be one thing if you were incredibly studious and wanted to get straight A's, but it's kind of like you don't like school, you don't want to play, like, we have to find something. And I and I realize it's part of like a trial and error and that I think is. My own challenge as a parent is trying to accommodate the different needs of each kid.

• 1:40:13Ken Rideout?

  And they're so, like I said, they're so wildly different. And I definitely don't want to put my expectations for myself in my Yeah, on, I don't want to project anything onto them. I'm so aware of like all my own flaws. Like it's my worst fear is that I could do this to them. What I, to carry some of the damage that I'm carrying. So it's like this constant struggle of like trying to do what I think I need to do for me and then also be a good role model and demonstrate to them how to do all the right things.

• 1:40:44Rich Roll?

  Sure. Yeah, it's rough. And no matter what you do, they'll, they'll tell you how, how you did it wrong later.

• 1:40:50Ken Rideout?

  Oh, 100%, 100%.

• 1:40:53Rich Roll?

  It's rigged, my brother. It's rigged that way.

• 1:40:56Ken Rideout?

  Well, the real, one of the, one of the challenging things really has been to having an Ethiopian daughter and like trying to get her to connect and be proud of her roots. And it's like, and listen, I, I'm very straightforward. I'm like, I, I'm not trying, this is hard, that's hard. I don't want to be those guys at all. It's everything's so hard, but I would say it's very, very challenging. I know for her, she struggles with being different. It's not, it's not easy for her. And that like, oh, breaks my heart because I see her struggling with it and, and I'm not doing, like I want her to identify with other Ethiopians and other black girls. But it's like, how do you do that without looking like an idiot of like, hey, can we be friends? So my daughter can have a black friend. Like I, you know what I mean?

• 1:41:38Ken Rideout?

  It's like this finding that fine line of like introducing her to the right environment. So she can have exposure to other people. We live in a very like homogenous majority white area. And I'm aware of this. It was, it was more so in, in Palisades than it is in Nashville. But that to me has been one of the biggest challenges, like not that, it's not that it's like top of mind every day with between the, between her and I or the, or my wife and us. But it's, it's, it's there. And I'm like, I don't want to let this, I don't want to let it fester. I want to like have her from the jump, be proud of who she is. And I think that she struggles with that, you know, it's like she'll say to me like, I don't mind that the people know, um, adopted. I just don't want them to know I'm Ethiopian. And I'm like, why?

• 1:42:21Ken Rideout?

  And she's like, well, because, um, you know, I think she views like Ethiopia as like an undeveloped, like third world country. And she's like, doesn't want to be associated with that. But it's, you know, these are the musings of a 12 year old girl. So that, that part of it presents like a set of challenges that. Have been difficult for me. If it's something that I can suffer through, I'm good. But if it's something that takes emotion and intellect and really at times painful like emotional processes, like it's very.

• 1:42:49Rich Roll?

  Well, it's a completely different skill set because everything that makes you successful as an athlete is useless in trying to solve this problem. You can't will it to be any different. And there's no sort of laundry list of items that you can check or hard work that you can put in to alleviate that pain or, you know, show her the way forward. Like that's a journey that she has to go on for herself.

• 1:43:16Ken Rideout?

  Yeah.

• 1:43:16Rich Roll?

  On some level.

• 1:43:17Ken Rideout?

  Yeah.

• 1:43:17Rich Roll?

  And it's hard to be feel to like tap into that. I mean, it's as a sober person, you understand the concept of powerlessness. Like there are things you can do, but ultimately it's her experience.

• 1:43:29Ken Rideout?

  Yep.

• 1:43:29Rich Roll?

  You know, that she has to have. And there's really nothing you can do to to control that.

• 1:43:36Ken Rideout?

  That's right.

• 1:43:36Rich Roll?

  That's a hard thing as a parent, right? When you see your kid in pain, you want to solve the pain. You want to fix it. You want to make it go away. And sometimes you gotta sit with it.

• 1:43:47Ken Rideout?

  Yeah.

• 1:43:48Rich Roll?

  Cause it doesn't work that way.

• 1:43:49Ken Rideout?

  I'd say the same similar situation with my wife is like she'll tell me what's something that's bothering her. I'll be like, I'm gonna fix this right now. She'll be like, I don't need it fixed.

• 1:43:56Rich Roll?

  Yeah.

• 1:43:56Ken Rideout?

  And it sounds crazy, but that's.

• 1:43:58Rich Roll?

  You to listen and hear me. Yeah.

• 1:43:59Ken Rideout?

  It sounds cliche, but like as soon as she starts going like, this is what happened. I'm gonna fix it right now. And she's like, dude, I don't need it fixed. I just want you to listen to me. And I'm like, yeah, but what is that gonna accomplish? We need to fix this. It's just like different, you know, men are from Mars, women are from Venus.

• 1:44:14Rich Roll?

  Sure, sure, sure.

• 1:44:15Ken Rideout?

  Been so real for me than having a daughter, especially like, you know, a diverse family and the challenges that go with it. I mean, I love every second of it. I'm just, I'm kind of outlining some of the challenges, but I would be remiss if I didn't say, I feel like the luckiest person in the world. Like I get emotional thinking about it, especially when people say to me like, oh, what you did for her is unbelievable. It's crazy. And I, I know why they say it, but I wish people would recognize too is like, you need to understand that maybe she did more for me than I did for her. And maybe she was destined to be the next Empress of Ethiopia. What did I do the right thing taking her out of there? Like who, who knows? But I made a decision that for all of us. So it's hard for me.

• 1:45:01Ken Rideout?

  To think about it in those terms, I, I, does that make sense?

• 1:45:04Rich Roll?

  Yeah, for sure.

• 1:45:06Ken Rideout?

  It's, it's, it's sometimes that, oh, that comment always brings up like such emotions. I mean, when people tell me that, cause I'm like, I'm not gonna like, I'm not gonna lecture someone or tell them why they're like, why they might be off base there, but I internalize it like, ah, am I doing the right thing? Like, was this selfish, was this selfishly motivated? Or was?

• 1:45:27Rich Roll?

  But just the fact that you're asking yourself that question tells me that you're a conscious dad, you know, cause there's a lot of people that don't have that level of self-reflection or don't engage in that kind of internal dialogue. And it's that, that process of questioning your decisions, even when to an outsider, it looks like obviously you did the right thing. The fact that you still are like, did I, did I not? I don't know. I mean, I think that's the engine of a good parent when you're always like evaluating whether you're doing something right or wrong, because there's so much gray.

• 1:46:00Ken Rideout?

  Yep.

• 1:46:01Rich Roll?

  And we don't know, you know, and we can read all the books and whatever, but like, when you're in those moments and those, you know, challenges present themselves, we're all just doing the best that we can. And sometimes we get it right and sometimes we don't. And often we don't know for years whether we made the right decision or not.

• 1:46:18Ken Rideout?

  That's right. And as we're talking through all these different challenges of life, and I hope I'm doing a good job of kind of highlighting, like the race results speak for themselves. Anyone can see that. But I hope that I'm representing to people that like, life isn't, Instagram isn't real life. That's just a small snapshot into like what I want to share in, as a still image. But really, I hope that what comes through in this interview is that like, no one is special, no one's unique, meaning we are all dealing with internal struggles. And I hope that, you know, by, by sharing some of these things, it, it, it lets people know like, no matter what you've been through or what you're going through. You can still get better. You can today, every day, you get a chance to start over.

• 1:47:03Ken Rideout?

  And it it's easy to say this stuff and it sounds cliche, but the running is a perfect reflection of that. It's like I always post on Mondays, like, let's go, it's Monday, let's start this week. But then when someone says it back to me, I'm like, hey, it's Monday, let's go. I'm like, every fucking day is Monday and every day is Saturday. It's the same thing over and over. But when someone says it to me, it has different context. But I'm trying to motivate and to tell people like, let's go. No matter what's going on internally, the one constant and the one thing you can control is what you do today. So what I've been trying to do through the running is use that as a coping mechanism to a certain extent with all these different, all this internal noise that can get loud in my head at times. And and and I don't want to like use drugs to combat it. And this for me has been the outlet that's helped.

• 1:47:48Ken Rideout?

  But I I would say to your earlier point and probably to my wife's like point for the last 20 years is like, what I really need to do and what I've like committed to do with her is like, I really need to like talk to someone on a regular basis and get comfortable with that. If the running wasn't there, can I still have the same inner peace? And that's to me is hopefully what like people take away from this is that that's the running is just a piece. And and I don't want to belittle my accomplishments, but I say, anyone can do this. Anyone can just go out, set a goal and and set about doing it in a workman like fashion. It's just, there's no substitute for hard work. You know, the expression, work works. This stuff that I did, like you were saying, like, you just ran 10 miles a day.

• 1:48:30Ken Rideout?

  Like, I literally went from like a 320 marathon to a 233 marathon from running 10 miles a day with no structure, no real training plan, just knowing that, huh, the more I run, the stronger I get at any distance.

• 1:48:43Rich Roll?

  You're also pretty humble about the whole thing, like you're in check with your humility. Like, you always say, like, I'm no great athlete, like, I got into this late and I still don't really know what I'm doing and all that kind of stuff. And I think that's really. Powerful because your accomplishments are so obvious in this regard. And you know, to your point of like, the internal struggles and the battles that like, we all have and we all share, you know, it might be appropriate as we kind of start to wind this thing down, to share a little bit more about those mindset tools or mantras or practices that you've developed that have been effective or might be a catalyst for the person who's still on the couch or looking for that way forward on a new trajectory.

• 1:49:27Rich Roll?

  Because you know, you've, you've, you've made such radical changes in your life, like, you know, how do you communicate that to somebody who's on the precipice of making that breakthrough to kind of, you know, give him the wind in the sails, so to speak?

• 1:49:42Ken Rideout?

  The one thing that I will say, I heard your interviews with David Goggins, I mean, I've heard a lot of your interviews, but one of the things that he said that really resonated with me that always comes back to my, to top of my head is that like, this is what I do. This is just what I do. When I get up to run, it's funny because as you build some like mental toughness and callous your mind a little bit to the reality that like this is every day. It's like, you know, like when you're going through recovery, it's like, how the fuck am I gonna not drink for two weeks? Like, you don't have to. You only have to not drink for the next hour and then we'll deal with the next hour. That's the running is like, you just have to set a real goal. And if nothing else, and I think

• 1:50:26Ken Rideout?

  it's almost easier later, later in life, because I've made so many mistakes in my life and we all have, but today you can start doing the right thing right now. Set a goal. It doesn't, I always wanna be mindful of people's abilities and capabilities and say, you don't have to run 10 miles a day, but if you've never run, maybe you're gonna start walking one mile a day minimum and set realistic goals. Like, okay, I don't care like how out of shape you are. That's not that ambitious. If you, if you have something wrong with you, that's a different story. But if you're healthy, Start with walking a mile. Maybe it's running a 5K if you're capable of that or a 10K. But be dependable to yourself. You, it's shocking what, how much that can help you in other areas of your life when you're dependable to yourself.

• 1:51:07Ken Rideout?

  When you know, I know that when the, if the shit hits the fan here, I know I can count on myself to do the right thing when the chips are down. Left to my own devices when things are fluffy and cool and it's easy to make mistakes. But if the chips are down and there's like something incredibly important happening, like I know I can count on myself because I have nothing else, I've proven that to myself and I have to, you have to believe it yourself. So back to my point about David Goggins with this is what we do. When I wake up, it never, ever enters my mind and I, I'm so far removed from having a debate with myself of if I'm gonna run, that I know it might be hard for some people to hear, but like there's never an inkling of doubt of like, I'm not doing this. I'm tired, I'm going back to bed. I just think, is it raining? Oh, it's raining, damn it, this is gonna suck.

• 1:51:52Ken Rideout?

  I hate running in the rain, but I'm doing it. And I mean, even when I had the shoulder surgery, it was like a blizzard outside. And I was like, dude, it's, you can't even see outside. It's like a whiteout, what are you doing? I'm like, I gotta do this. She's like, we have a fucking woodway treadmill, go in the basement. I'm like, I, I feel like, I don't mind running on the treadmill sometimes, but I was like. Isn't that how you fucked up your shoulder or your knee or something like that? Yes, yes. I had a damaged shoulder for years. It was just like, you know, it bothered me, but not terribly. I fell down and it like wrenched behind me. I mean, I fell so awkwardly as I was like turning around a corner, the people in the guard shack and like where we live must have been like, what is this guy doing? There were no cars, no nothing. And I, I just tore everything, labrum, rotator cuff.

• 1:52:35Ken Rideout?

  And I just, I had gone and the guy was like, oh, you need everything fixed. And I was like, all right, we'll do it in April after the Boston Marathon. And after like a week or so of trying to get through this, I just called him. I was like, dude, I can't take it anymore. I, I come in tomorrow. And he was like, you know, it was a Friday, he said, come in Tuesday. And I went in Tuesday and got it done. But to my point about the mindset thing is like, you, if you can just prove to yourself that you can do this, get up and run every day for 10 days, see if you can get 10 days. Cause if you get 10. 20 sounds good, too.

• 1:53:02Rich Roll?

  Hmm.

• 1:53:02Ken Rideout?

  And then the next thing you know, someone was like, we've got a, um, I work with a, a brand called Rowan, a clothing brand. They have a, um, a five, 5K, 30 day 5K challenge. He's like, yeah, we're doing this. Do you want to do it? I was like, yeah, I've been doing it for like five years. I'm gonna, I'll one up you. I'll do 15K.

• 1:53:19Rich Roll?

  Yeah. That's just a subset of what I'm already doing every day and have been forever.

• 1:53:24Ken Rideout?

  Yeah. But, but I think that even that as a starter for some people is like, I know Goggins puts up challenges all the time and, uh, he's someone that I respect his mindset and I also respect his humility in that like he doesn't profess to know everything, but he knows what he does know. And that's kind of how I feel about the running is like, I know what I know. I'm not the best, but I know that you're gonna get my best when I show up. We're, we're, we're going. Like you're gonna have to kill me to beat me if, if it comes down to like my choice. I'm gonna empty the tank and, um, but I, I think that with the mindset stuff is you have to prove to yourself that you can do it because I haven't, like you said, I have nothing special. I'm, I'm every man. I'm, I'm an average athlete at best. I played division three football and hockey. I was like jack of all trades, master of none.

• 1:54:08Ken Rideout?

  I was just willing to do whatever I had to do to stick around and be on the team. If they needed me to fight, I'll be like, okay, I'll fight.

• 1:54:15Rich Roll?

  But your advantage or your superpower is your mental game. Like I hear somebody who, who really understands the idea of non-negotiables. Like you're able to commit to something and follow through with action, you know? So it's not about VO2 max or anything like that.

• 1:54:34Ken Rideout?

  I couldn't tell you any of those metrics.

• 1:54:35Rich Roll?

  It's just about like, do you ever wear a heart rate monitor, by the way? Like, okay.

• 1:54:39Ken Rideout?

  Sometimes my watch measures it.

• 1:54:41Rich Roll?

  Yeah.

• 1:54:41Ken Rideout?

  I'll put it on Strava and people will be like, dude, heart rate of, I don't know, 185, blah, blah, blah. I'm like, oh, that was my heart rate? I didn't even, I didn't even know.

• 1:54:48Rich Roll?

  Mario doesn't make you strap one on once in a while?

• 1:54:51Ken Rideout?

  That's the best thing about Mario. He knows who he's dealing with.

• 1:54:53Rich Roll?

  Yeah, okay. But the point being like, that's, that's, that's really like the engine behind all of this is like that mental discipline, right? And that's a muscle just like anything else. That's something you can train, just like you can train your running or your cycling or what have you.

• 1:55:08Ken Rideout?

  A hundred percent. I wish that that was the one thing that people take away from this is that this guy like I think of myself as just a dopey guy who's made a shitload of mistakes like anyone else. Same insecurity, the same fear. The difference is, I'm not letting that control me anymore. Fear is such a powerful emotion. When I moved to New York City, I mean, when I was in high school, it was like, my kids asked me the other day, Dad, did you ever get in a fight when you were a kid? I was like, did we get into a fight? I probably had two hundred fights in school and to think about it is insane. Cause there hasn't probably been three fights in my kid's school in like the last ten years. But it's just such a different world. But the point is like, everyone is of, everyone feels nervous about those kind of interactions. But the minute that people think you're too nervous to do it is the minute that they'll always wanna have a problem with you, like classic bully shit.

• 1:55:53Ken Rideout?

  So in high school, I realized, I'm so afraid of this and this is an ever-present danger of growing up in this kind of like inner city, like blue collar thing. It's like, there's a lot of people dealing with a lot of shit and it's like, you don't wanna be the target of someone else's shit. Like half the kids I was in elementary school with were then in the prison. So it was like, you know, you're with these kids who have, you know, some of them have very difficult households and situations. So you're in this dangerous situation. I was just like attacked it from a very practical standpoint in that I just went to the Somerville Boxing Club. Where literally like John Ruiz, the heavyweight champion of the world was in there training. A boxing gym is like the most intimidating, but also the most welcoming place in the world. Anyone that has the guts to come in and wants to train, let's go.

• 1:56:34Ken Rideout?

  If you prove that you can come back after getting punched in the face, you're good. Cause that's the ultimate test is when you get hit back. Holy shit, do I wanna do this? This isn't fun. I can't see. I think my nose is broken and that doesn't take much. So I started boxing in high school and scared to death every time. Like I said to you, when I pulled in here, I was like, had that anxiety feeling of like, oh shit, I'm gonna spar with this guy who's a killer. And it's just similar emotions. The point is that emotion, whether it's tied to fear or telling your story to someone or a big meeting in work or a speaking gig. The emotions are the same. If you can learn to deal with those emotions and harness that, everyone feels them the same, but the people who are successful learn to harness

• 1:57:18Ken Rideout?

  that and use it as their own tool, whether it's get them more ready or get them to perform at a higher level. And you see it all the time. You don't think that Tom Brady's scared to death in the fourth quarter when they're trailing in the Super Bowl. You know, the difference is he's feeling the nerves, but he's like, let's go. He's using his like.

• 1:57:33Rich Roll?

  Right. You have a strategy to channel that into something productive as opposed to letting it capsize you.

• 1:57:40Ken Rideout?

  And the boxing for me was my outlet that I was scared every time I went, every fight, every sparring session, but I kept going because I don't want to be controlled by fear. And it served me in a lot of ways in life, including dealing with addiction. Because when I was like, you know, when you're about to go through withdrawals and entering into this like uphill battle at this recovery, you're like, I don't want to do it. Let me just put it off for a week. And that's, if you have these tools, you're equipped to deal with all these different challenges. And look, it doesn't make you immune to mistakes. You're gonna make mistakes, but hopefully if you have these mental tools, and I think you can continue, like you said, increase the strength of that mental tool, that is mindset, by setting realistic goals for yourself and working towards them. Maybe it's like

• 1:58:24Ken Rideout?

  I said, a mile a day, two miles a day. But the boxing was a good analogy for me in that I just kept doing it and kept dealing because nothing else seemed even remotely scary to me as getting in a fight. And, you know, boxing for the New York Athletic Club, even as an adult, I was like, man, why am I doing this? This is so scary, but I'm doing it anyway.

• 1:58:42Rich Roll?

  And now you got a podcast about it.

• 1:58:44Ken Rideout?

  It's dream come true. Get to talk about boxing with the best like boxing minds in the world. It's almost too good to be true. The fight with Teddy Alice.

• 1:58:51Rich Roll?

  Yeah, yeah, yeah. How did that come about?

• 1:58:53Ken Rideout?

  Again, all things good in my life that have happened have come through endurance sports. When I moved to LA, literally like this, a week or two later, Rob Moore called me, got my number from someone in New York. I didn't know him. And he's like, hey, you just moved out here. I just moved out here. We're both into triathlon. And I was racing for a team called Everyman Jack, my friend Rich Viola's brand. They have like a very strict policy. It's a very competitive team and they never let anyone on in the middle of the season, but the guy, I got along really well with Rich. I said, hey, I got a new guy for us, Rob Moore. And he was like, okay, he can be on the team. And you know, it was probably like, for some people would be like, oh, yes, I've been picked up by the Celtics. If you're in triathlon, that was a good team. Someone on that team one year won every single, a member of that team won every single North

• 1:59:36Ken Rideout?

  American Ironman for the overall amateur title for like a year or two. So Rob and I started training together extensively. Rob was in PR, in corporate PR in New York, moved out to LA, was doing some freelance stuff. And I just, one day I said to him, why don't you do some PR for some fighters? He'd be good at it. And you know, it's a long story, but basically I introduced him to a kid named Mike Lee, who was from Notre Dame. Yeah, I've had Mike on the podcast. Oh, yeah, that's right. I'm sorry. Yeah, Mike is my, is my friend. I love, he's such a nice guy. So Rob started working with Mike. Mike's dad introduced Rob to Teddy. And Teddy had been on ESPN for years and they stopped using him for the broadcast. He had a falling out related to the Jeff Horn, Pacquiao fight in, in Australia where Teddy just was like,

• 2:00:20Ken Rideout?

  this is not right. This, and called out a bunch of injustices. And the promoters and the network did not like it. And they started using him less. He was introduced to Rob and to Rob's credit, he was like, you should have a podcast. We should have you on social media. And, and Rob said, you maybe you should try my friend Ken as a co-host for the, for the fight. And you talk about nerves, man. I would have rather gotten a fight than do that first episode. I was so bad, but I wanted it so bad. And we recorded an episode, it was like two and a half hours. And, and now we've just gotten to such a natural cadence. And like Teddy is like, I mean, I hesitate to say a father figure because he's only like a few years older than me, but just, I love him. He's, he's the most authentic person, but he's also no nonsense. You, you, you can't have half-assed relationships with

• 2:01:05Ken Rideout?

  wholehearted people. Like, if you're friends with Teddy, you're friends with him.

• 2:01:11Ken Rideout?

  All in, there's no tolerance for like, small mistakes or transgressions with regards to that friendship. And the accountability that it, that it requires is, you know, there's, it's hard not to have immense respect for a guy like this. He's just, you know, at times you're like, dude, I, I, sorry, I missed that. And it's like, no, no, no, there's no, there's no accidents. Why did you do this or that? And I'm like, but at the same time, he's the most generous, kind, loving person in the world. When we started working together, I just thought, oh, Teddy's in boxing. He has access to everything. Hey Teddy, can I get tickets to the Canelo Jacobs fight? Instead of saying like, I don't have a relationship with that promoter. And now knowing what I know now, like, just would never ask anyone for anything and beholden to anyone and especially in boxing.

• 2:01:55Ken Rideout?

  Instead of just saying he didn't have that relationship, he went out and bought the tickets from a broker and gave them to me. And, and I was just like, when I found out, I was like, oh my God, I'm so embarrassed. But this is what I love about him. It's like, he'll be hard on you if, if, if he thinks that you've like messed up. But if you need something, he'll help you bury a dead body. He's, that's the kind of guy he is, but he expects the same from you in return. So in that regard, it's been a, um, it's been an incredibly rewarding relationship for me and Rob. And the, and the three of us work so closely together every week. And it's funny because people will, they, it's funny when people talk to me about the show and they, you know, they're like, hey, can you talk to the producer and do this? I'm like, you're, you're talking to him. There's only three of us. Everything you see is like a three man.

• 2:02:38Rich Roll?

  The assumption there's a huge operation behind the scenes. Yeah. But I, I didn't know that Rob just cold called you though, and that's how it happened.

• 2:02:44Ken Rideout?

  Oh, when we moved to LA? Oh yeah, cold called me. And as a matter of fact, the first time he called me, like, I mean, you kind of see what my personality is like. I called the kid who introduces and I'm like, dude, what the F is wrong with you? You gave a stranger my phone number and now the guy wants to train with me. And I was like, oh dude, thanks for introducing me. This is like one of my best friends now. Now, I mean, I love this kid. I would do anything for him. He's been one of my biggest allies in my life. I, I would not be able to do half the shit I've done without Rob Moore. He's my man.

• 2:03:10Rich Roll?

  I agree with all of that. We should probably say, because his name's come up like 100 times, he's sitting right over there. For people that are listening or watching are like, who is this Rob Moore guy? Rob is the podcast kingmaker. He's the producer behind your show, your partner. He's also partners with Andrew Huberman and is the guy behind the curtain who kind of makes the whole Huberman Lab thing work, which is unbelievable because that show has ascended to, you know, the highest ranks of, you know, popular culture and everybody's embracing neuroscience and everything Andrew has to say about that, which is really great. And, you know, kudos to you, Rob, for everything that you've built. And, you know, I appreciate your friendship. And, you know, we don't have an official relationship, but Rob has always brought amazing guests to the show, including yourself.

• 2:03:54Ken Rideout?

  I was just gonna say, you realize, you realize what you're doing now, right?

• 2:03:57Rich Roll?

  What?

• 2:03:57Ken Rideout?

  Every person who thinks they can be a guest on your show is gonna be like, hey, Rob, you want another?

• 2:04:01Rich Roll?

  Now, Rob's gonna be like, you gotta cut that out of the podcast.

• 2:04:04Ken Rideout?

  But, uh,

• 2:04:05Rich Roll?

  We can if you want, but I wanted to share a little public love for Rob, that's all.

• 2:04:09Ken Rideout?

  And to, to your point is like, I had done some work with David Sinclair in, in Boston. I had raised some money for his life.

• 2:04:18Rich Roll?

  I saw him the other day.

• 2:04:19Ken Rideout?

  Yeah, I saw you at Life Itself. So I interviewed with Lance. I trained with Lance a few times.

• 2:04:23Rich Roll?

  Yeah.

• 2:04:23Ken Rideout?

  I have a friendly, very friendly relationship, rival relationship with Lance. He might not know that we're rivals, but I'm gonna kick his ass every time I see him. But we've done some running and riding together. And that Life Itself thing looked good, but I saw David there. But I raised some, I helped David as, in my professional career, I now work as, I did work as a placement agent slash banker in helping, initially I was helping private equity and venture funds raise assets from institutional investors. And then I started working on private placements, so like for brands and startup companies, but more, more things aligned with like sports, health and wellness. And I had done some work with David and then connected David and Rob. And then Rob started working with David and like all of a sudden.

• 2:05:08Rich Roll?

  You're the point of connection between those two on that too, right?

• 2:05:09Ken Rideout?

  Yeah. And that's what I mean about Rob is like, he's been transformational. The relationship I've had with Rob has been like so mutually beneficial. It's been just incredible. And but, but I think that again, it goes back to the point of finding like-minded people and connecting through whatever activity, maybe you're a free climber or a mountaineer or something. But if you connect with the people that Are doing things that you're interested and you respect them. It's like, I just, if there's anything that I've done right in my life, it's, it's, it's finding endurance sports and then connecting with like-minded people. And again,

• 2:05:41Rich Roll?

  Not on LinkedIn.

• 2:05:42Ken Rideout?

  No, again, about the networking. If you're consciously, if you consciously think you're networking, you're not. Those are just genuine, organic relationships. But anyway, yeah, Rob started working with David and did the PR on his book and was just massively successful. And all of a sudden, David and Andrew, I mean, Andrew's a superstar and he's a very good friend. I love him. But like to see what Rob has been able to help these guys do. And Rob's the kingmaker in the podcast world. He's, I don't do anything without talking to Rob first.

• 2:06:13Rich Roll?

  That's it right there. Well, awesome to talk to you, man. I, I, I trust that like, is Berlin the next race that you've been ready for right now?

• 2:06:23Ken Rideout?

  Berlin, September 25th.

• 2:06:24Rich Roll?

  When is that? September?

• 2:06:25Ken Rideout?

  And two weeks later, I'll do Chicago. See if I can do a quick turnaround.

• 2:06:28Rich Roll?

  Make any predictions on Berlin, Chicago, double?

• 2:06:30Ken Rideout?

  You know what? I, I, I believe that if you speak your truth and, and aren't afraid to like say even ambitious goals, like, hey, hold me accountable. Like, I think that I could run 226 there. I think that 225, I wouldn't be like, oh my God, what happened? Did I cut the course? 225 on a, on the right day? When I ran 110 in Nashville, if I feel like that on a marathon course, especially like a fast course, like, I don't think that that's unrealistic at all. And yeah, I would love to be able to set a new PR in the marathon this year at 51. And then, like I said, two weeks later, I'll do Chicago. I have much lower expectations there. I just want to win my age group. And then in March, I'll do the final marathon major in Tokyo.

• 2:07:14Rich Roll?

  Wow. Wow.

• 2:07:16Ken Rideout?

  Seems crazy to me because when I started running, I was like, I just wanted to finish the marathon or qualify for Boston. And now to look on my bookshelves when I have a Zoom call or something and see hardware from Boston, New York, London. I'm like, it's so funny because the stuff, you want to win this stuff and then you have it and you're like, next, that stuff. It's like I said with the mountain, like you get there and you're like, I climbed Everest. I wonder if I can climb every highest peak in whatever the next challenge is. I wish that there was, that I would do a better job of appreciating like the process more than I do. And Each accomplishment a little bit longer as opposed to like, all right, what's next?

• 2:07:53Rich Roll?

  Well, build that into your non-negotiables.

• 2:07:55Ken Rideout?

  You're right.

• 2:07:56Rich Roll?

  You know?

• 2:07:57Ken Rideout?

  No, you're right. You brought up some really good points that I've got a lot of things to reflect.

• 2:08:01Rich Roll?

  It wasn't my intention, man. I'm just here to have fun with you.

• 2:08:03Ken Rideout?

  I'm having a great time.

• 2:08:04Rich Roll?

  I'm inspired by everything that you're doing, man. I think it's super cool. I'm so glad we have this opportunity to sit down together. For people that are watching or listening, check out Ken's stuff on Strava. He's for real. You can see the paces that he's throwing down. He's not fucking around, I'm telling you right now. And we'll be cheering for you, my brother, and come back and share some more with me sometime. This is super fun.

• 2:08:28Ken Rideout?

  Next time I come back, I've got some crazy prison stories that are gonna make your head spin.

• 2:08:31Rich Roll?

  Yeah, all right. We'll just do, we'll just do three hours of prison stories.

• 2:08:36Ken Rideout?

  There is no shortage. Thank you for having me, man. I honestly, I really appreciate it. Congratulations on all your success. It's, I love it. I love seeing people like, make a career out of doing things that are actually helpful and make them happy. And I'm sure you don't feel like you're working.

• 2:08:52Rich Roll?

  It can feel like work. It's still, you know, it's still work. You want it, you want it to be, it's like you prepare for it like you prepare for a race. Like you want to create the environment for the best experience and that doesn't happen, you know, without some effort, but mostly joy. You know, and, and it's such a privilege to be able to meet people like yourself and

• 2:09:09Ken Rideout?

  It certainly comes through.

• 2:09:10Rich Roll?

  So, yeah.

• 2:09:11Ken Rideout?

  Certainly reflects in the show, man. It's awesome. Thank you again for having me. I appreciate you.

• 2:09:16Rich Roll?

  Cool. Peace.

• 2:09:17Ken Rideout?

  Peace.

• 2:09:22Rich Roll?

  That's it for today. Thank you for listening. I truly hope you enjoyed the conversation. To learn more about today's guests, including links and resources related to everything discussed today, visit the episode page at richroll.com where you can find the entire podcast archive, as well as podcast merch, my books, Finding Ultra, Voicing Change, and The Plant Power Way, as well as The Plant Power Meal Planner at meals.richroll.com.

• 2:09:53Rich Roll?

  If you'd like to support the podcast, the easiest and most impactful thing you can do is to subscribe to the show on Apple Podcasts, on Spotify, and on YouTube, and leave a review and/or comment. Supporting the sponsors who support the show is also important and appreciated. And sharing the show or your favorite episode with friends or on social media is, of course, awesome and very helpful. And finally, for podcast updates, special offers on books, the meal planner, and other subjects, please subscribe to our newsletter, which you can find on the footer of any page at richroll.com. Today's show was produced and engineered by Jason Camiolo, with additional audio engineering

• 2:10:35Rich Roll?

  by Cale Curtis. The video edition of the podcast was created by Blake Curtis, with assistance by our creative director, Dan Drake. Portraits by Davy Greenberg and Grayson Wilder. Graphic and social media assets courtesy of Jessica Miranda, Daniel Solis, Dan Drake, and A.J. Akpodiate. Thank you Georgia Whaley for copywriting and website management. And of course, our theme music was created by Tyler Pyatt, Trapper Pyatt, and Harry Mathis. Appreciate the love, love the support. See you back here soon. Peace. Plants.