In this episode, Ken Rideout, a former Wall Street trader and current endurance athlete, shares his journey from a high-pressure career in finance to becoming a competitive ultra-marathoner. He discusses the mental toughness required to excel in both fields, the importance of “all-in” commitment, and how he applies the same discipline from his trading days to his athletic pursuits.
Topics: Finance, Endurance Sports, Mental Toughness, Career Transition, Discipline, Ultra-marathons
Early Career and Trading Floor Culture [00:00]
Ken Rideout: Back in like the late 90s, trading desk was like a locker room. It was very like alpha-driven, um, a lot of hazing and shit. But I mean, I was at the time boxing for the New York Athletic Club. I had played hockey. I mean, I was, I worked in a prison for four years. So these nerds were hazing me and one day I just cuffed the guy. I just slapped him across the face and almost knocked him out of his seat. And needless to say, they fired me. But I was covering these young guys at Enron and they told the senior traders what had happened. And one of the senior traders, who happened to be from Martha’s Vineyard outside of Boston, called me up, said, “Hey, I got a job.” I didn’t even know we had competitors. That’s how naive I was. I didn’t know there were other brokerage shops. I was there like two months and, um, I mean, I barely knew what a bid and an offer was. And, um, this other competitor offered me a job starting the next Monday.
Transitioning to the Podcast [00:55]
Shaan Puri: All right, we get right into this. Ken, uh, thanks for coming, man. I uh, do you know at all what you’re getting into or no?
Ken Rideout: Yeah, yeah. I heard uh Andrew Huberman on the show, my friend Andrew.
Shaan Puri: Good. Well, let me um, I’ll let you kind of do the intro, but I want to tell our audience what I know about you and why I think it’s cool that we have you. Basically, I was telling Sean, you’re, so we take pride in like finding people a little bit before they explode. You’re getting quite popular. You’re in the Wall Street Journal the other day, so things are happening for you. But you’re to me like, you’re like the next David Goggins in my mind. Like, you know, you’re kind of a freak athletically, but you’re also more so a freak mentally. And you talk about a lot of like just being tough. You got some crazy quotes that uh we’ll talk about later about how uh uh, you know, like you like running because it’s all about suffering and things like that. And so you said a lot of really interesting things. Sean and I are also huge combat sports fans, so I listened to the pod with Teddy Atlas that you’re on. And I know a bit about your background, and so I wanted to have you on to talk about that. Typically, we talk about business stuff. Huberman was a little bit of a, we had him on, that was a little non-business. You’re a little bit non-business, but you had like an interesting background where you worked on Wall Street, worked on, I worked at Enron, I think. You did a bunch of interesting stuff. And so that’s kind of why we had you on. What um, well, how do you give your introduction? What do you, what do you say you do?
Ken Rideout: Yeah, well, thank you for that introduction. Uh, when I hear people introduce me sometimes, I almost don’t feel like they’re talking about me because I, I think part of what makes me unique is I, I at times have, don’t have the highest opinion of myself and always feel like I, there’s I should be doing more. But, um, I think that the comparison to David Goggins is somewhat accurate, although it’s, it’s accurate. I can see why others would think that, but I don’t think that he’s soft at all. I think he’s probably maybe more, more aggressive and uh alpha than I am, I would say. I try to be, I don’t know. I think that the way I come across, you know, when I was on Rich Roll, he described me as being his, his initial impression of me prior to meeting me was that I was very aggressive and uh alpha and intimidating, and I don’t see myself that way. I see why other people would see that, but I think of myself as that, that alpha or aggressive exterior is almost like a defense mechanism because inside, I think I’m very emotional and sensitive and so much so that my way of protecting that sensitivity is to be so aggressive externally that it really takes someone unique and special to kind of see through it. Um, at least that’s my take from uh the the the the psychotherapy I’ve been involved in, but.
The “All-In” Mentality [01:33]
Shaan Puri: Well, the reason, and the reason we had you on, we typically, so it’s usually just Sean and I, or it’s like, we’ll have like billionaires and stuff on. So like these like wonderful people, but something that like I’ve been thinking a lot about lately and I’ve been talking to Sean about lately is just like toughness and like how it feels like good to get out there and work hard physically or to spar, do things like that, because even though we’re doing cool shit behind the computer, it’s still behind the computer and it feels good to live. And you say you’re not an alpha, but I think in the Wall Street Journal article you said, uh, “I’m the biggest male, I’m the biggest alpha male on the starting line. I’m ready to die to win.”
Ken Rideout: Thank you. Thank you for pointing that out because there was context to that quote. I said, my, my exact quote was, “When I’m on the out, when I’m on the start line, when it’s time to go, 100%, I’m alpha. I will step on your neck to win. I want to kill you. I want to destroy everyone.” But the minute that race is over, I’m everyone’s best friend. If I see someone fall down in front of me, I will stop and help them. I’ve, I’ve in triathlons have asked people, “Yo man, you all right?” I’ll stop and help you. I’m not, I say step on your neck and kill you to win, but not really. Like, this is, this is my mental process that I have to go through to get to the dark place that I need to get to, to suffer to the extent that I need to suffer to get the most out of myself. Running, you know, I ran, uh, 36 hours ago, I ran the Tokyo Marathon in 2:29:19. And the day before that, the day before that, Outside Magazine wrote an article, “How 51-year-old Ken Rideout runs sub-2:30 marathons,” and I saw the headline and I literally had an anxiety attack. I’m like, “Oh my god, the pressure is on.” I mean, I’ve run sub-2:30 three or four times, but it ain’t easy. And I know that that last five or six miles, the suffering and the darkness that’s coming with that, I can’t, it’s, it’s literally, physically the hardest things that I’ve ever done. It’s like your everything in your body, it’d be like if you’re driving your car and every single warning bell is going off, the radiator’s overheating, the oil’s low, you’re going to run out of gas. And you literally are like, “I can stop and no one would care.” Or I can push myself and know that I didn’t have another effing ounce to give. And that’s, it sounds cliché, it might sound corny, but that’s my process. That’s where I have to go to get to where I’ve gone to, to the point where guys like you with this awesome podcast want to talk to me. Like, I’m, I’m a regular guy. I’m a dope. I, I don’t see myself as special with the exception of being willing to die to get the most out of myself physically on these particular days, at races.
The Tokyo Marathon and Mental Preparation [05:59]
Shaan Puri: And you, so you said you just ran, you just ran the the a marathon in Tokyo 36 hours ago. You’re here now. And I didn’t know much about you before Sam brought it up. Sam goes, “Oh, I really want to have this guy on. Are you, are you down with it?” And I thought, I’ve heard that name, but I don’t know, who is that? And I was like, “Oh, is that the Teddy Atlas podcast guy? Oh wait, what’s the story?” And I, as I started looking into it, to me, there was a few things that really stood out. So there’s the kind of the obvious headline that here’s a guy who’s over 50 years old and is basically flying through these marathons, running super fast speeds. I don’t know the exact records or what what not, but you’re one of the fastest, if not the fastest, correct? In your kind of in your bracket?
Ken Rideout: Over 50. Yep.
Shaan Puri: Yeah. And so that’s kind of remarkable. And I think that’s, you know, that’s the key thing I want to get to is like, that’s an extraordinary thing and that doesn’t just come out of nowhere. And so, uh, you talk about being able to go to that place at the last five miles, what happens pre-race? Where do you, where how do you flip that switch? What is your sort of like, um, uh, mental state of mind or your psyche? What do you do mentally to prep yourself before these races?
Ken Rideout: Yeah, that’s a great question, and thank you for the opportunity to explain this because I think that it’s, um, important for people to understand when they look at this just on the surface, like you just described, like, “Wow, it’s extraordinary.” And, and by the way, when I hear it, it doesn’t even seem like you’re talking about me. So I, I, I don’t at times have the highest opinion of myself because of the struggles I’ve gone through with addiction. So as I’m telling you this, I’m super cautious that I, about coming across like a narcissist. I, I don’t want to come across like that. I want to be, I want to be very humble in how I describe this, but I’m going to be honest with the process prior to the race. I’ve spent before a race, and this one in particular, not no different than any other, I’ve spent 10 or 12 weeks like devoting all my physical energy or, or at least 90 minutes to two and a half hours a day of preparing for this for, let’s say, 12 weeks. When I get to Tokyo, the week before, I always go by myself. My wife, I have four young children. Even some of the local races, they don’t come to. Even when I think, “Oh, I’m going to win,” and you can see me win a race, like they’ve come to a few of them and it’s kind of uneventful for them. They come to expect me to win and I, in my mind, think they’re going to be so psyched when they see me win and then they’re like, “Okay, Dad, can we get out of here now and get a donut?” So, um, anyway, long-winded way to say, I have a very, um, very specific process that I have to go through in the days leading up. And again, I don’t want to sound like I’m like some elite professional runner, but this is how, this is what I do. This is the process. I have to get there. In the case of Tokyo, with a 14, 15-hour time change, I need to get there at least seven days early to get my body and my circadian rhythm on track with what I’m about to do because again, I’ve spent 12 weeks devoting so much energy to this. I don’t want to mess around when I get there. It’s very specific. I don’t make plans to go to dinner with people or very rarely, mainly because I’m a jerk. I know it. I’m very selfish. To me, again, I’m not a pro runner, but to me, this is my version of the Olympics and I am not there to mess around and have fun. It’s like, I’m, I’m on a work trip. So I get there and I just need to be alone by myself, think about what I want to do, try to stay positive. Uh, I’m a big believer in mindset and, and, and what you tell yourself is the truth. Reality doesn’t matter. Like, what other people think about you doesn’t matter. It’s the only thing that matters is what you think of yourself. And that goes into the same, that same thought process goes into preparing for this race. In my mind, I am a professional runner and I’m going to win the, you know, Olympic gold medal on Sunday. So I get there early, I go through my process and on race day, I’ve said this before in interviews, it’s like, I’m not, I’m nothing nice on race day. I don’t want to make friends. I don’t want to chit-chat. I don’t I’m a jerk. I know it. So I try to stay completely by myself. I don’t put my shit on other people, but I don’t want them putting theirs on me either. So I stay by myself. The race goes off, I know what’s coming. Some people are like, “How are the sights in Tokyo? What were the people like in the race?” I said, “I couldn’t tell you if we ran through the freaking Imperial Palace or not. All I know is the road in front of me and I get into like a tunnel vision where I can’t see any, I mean, I obviously, if I look around I could, but I don’t waste an ounce of energy. I don’t even try to look at my watch for, I don’t want to move any movement that isn’t completely necessary to get from A to B as quickly as possible. I’m trying to run the straightest line, I’m focusing. If people get too close to me, I’ll like kind of give them an arm like, “Dude, you’re getting too close.” Like I don’t want to trip. Someone at the start of the race in Tokyo, I was on right on the start line and two or three people right in front of me toppled and it was like they were caught in the whitewash, surfers just arms and legs flailing, elbows and knees smashing on the ground as people just trampled them at the front of a major marathon. It was crazy. So I don’t want them doing that to me, so I’m like, that’s what I meant about being a bit alpha at the start, but I don’t want to hurt anyone. I don’t want to affect anyone, but I don’t want to be effed with either.
The “Alpha” Mindset and Professionalism [11:02]
Shaan Puri: Did I see a, did I see a picture of of of you and Jason Calacanis over there?
Ken Rideout: Yeah, me and Jake, Jay Cal, yeah. It’s my dude.
Shaan Puri: How do you know him?
Ken Rideout: Kate, my friend Casey Neistat, who is, uh, do you know who he is? Guy, YouTube, um, guy, Casey. So I trained Casey last year for the New York Marathon. My friend Neve Schulman, who’s the host of Catfish on MTV, he connected us. So I trained Jason and uh, not Jason, uh, Casey and Neve for New York City Marathon. And then I heard Jason mentioning, um, running a marathon on on All-In and I just mentioned it in passing to Casey. Casey connected me. I saw Jason was in Tokyo. I sent him a text and then we ended up going to dinner one night and then a Tokyo food tour the next day. We went to like some super high-end sushi place and then a bakery. Jay Cal is like, he’s dialed. He knows where he wants to go. I know nothing. I was just like, “Just tell me where we’re going and I’ll be there. Just text me the address.” Um, that’s what I mean about the week before this.
Shaan Puri: You’re in the in-crowd. You’re you’re you’re hanging out with all the all the cool guys.
Ken Rideout: Brother, again, when I think about my friends like Andrew Huberman and David Sinclair and Joe Rogan, I think, “I can’t believe these guys are my friends.” I’m, I, I feel like the luckiest person in the world and I’m so humbled and honored that guys like you want to talk to me. It’s just mind-blowing, but it comes back to this point of I don’t have anything that anyone listening to this show doesn’t have. I promise you, I’m not a good athlete. I played Division III sports. I was just a hustler. And when I found running as a way of getting over an addiction issue with opioid opioids, I just decided I was done being mediocre and we’ll get into the career stuff and I’ll tell you how I did applied the same practice to my career in finance. But at the end of the day, you know, not again, not to sound cliché, but if you’re not all-in, there’s just too many competitors out there that are going to eat your lunch if you don’t bring your A-game every day. But when you do dedicate your 100% effort to one particular goal, it’s very hard to beat the guy who wants to die to win. And that’s kind of what I applied to running and and and it’s attracted these other kind of people that recognize that I am like serious about the things that I get involved in.
Career and Financial Success [13:12]
Shaan Puri: Well, the thing that you’re interesting is the you just have an interesting life. Did I read, did you used to work at Enron?
Ken Rideout: No, good question. I, I, I was working in finance. My very first job, if you want me to kind of walk through my career, I don’t want to like jump around. I started in, I moved to New York right after I graduated college. I had a pharmaceutical sales job for a few months, but when I moved to New York, I saw all these younger guys my age working in finance and making a ton of money. And I was like, I was making like $36,000 and my like rent and student loans came to more than my take-home pay. I was basically like living on borrowed time in New York, living in a shitty walk-up. And, um, long story short, I was playing a pickup ice hockey at Chelsea Piers and a French Canadian kid, uh, who played minor league hockey, asked me if I wanted a job as a, um, like a trading assistant on a, on an inter-dealer brokerage desk brokering, uh, electricity trades between the utilities and Enron was one of those clients. And the way it worked was the junior guys at Enron would trade like next-day power, which was like the commission was like literally like $5. But if you didn’t do that as a service for these accounts, they weren’t going to trade the like big ticket items with you. So, long story short, I was doing that. The guys on the trading desk, you know, back in like late 90s, trading desk was like a locker room. It was very like alpha-driven, um, a lot of hazing and shit. But I mean, I was at the time boxing for the New York Athletic Club. I had played hockey. I mean, I was, I worked in a prison for four years. So these nerds were hazing me and one day I just cuffed the guy. I just slapped him across the face and almost knocked him out of his seat. And needless to say, they fired me. But I was covering these young guys at Enron and they told the senior traders what had happened. And one of the senior traders, who happened to be from Martha’s Vineyard outside of Boston, called me up, said, “Hey, I got a job.” I didn’t even know we had competitors. That’s how naive I was. I didn’t know there were other brokerage shops. I was there like two months and, um, I mean, I barely knew what a bid and an offer was. And, um, this other competitor offered me a job starting the next Monday. I was making 40 grand, they offered me a job at 80 grand. I mean, to me that was more money than anyone I knew made. So I was like, and and the other thing is this guy’s hazing me. I had a huge black eye from a fight at the New York Athletic Club. Like I was not like a punk that you could just like, I, I didn’t strike you come across as like, “Hey, bully me, I’m a big sissy.” Like I was a guy, you know, so when he did it, I was like, “You got the wrong guy, dude.” And I cracked him. And needless to say, he almost started crying because I was like, “When you leave this office, I’m going to beat the crap out of you.” And he’s like, “I’m not, I’m not going to leave.” I go, “You’re going to have to sleep here because when you come outside, you’re getting beaten.” And they were like, “Okay, Ken, you got to go before we call the cops.” And again, I had no safety net. I couldn’t call home and ask for money. There was like, I worked in the prison, my stepdad and brother were inmates in the prison. No one was looking to help me in my finance career in New York. To them, I was like an anomaly. You know, I was already like the richest person they knew just by having a job in New York City. So, um, yeah, it was nerve-wracking and, uh, so that’s how my career started and the guys at Enron were just like good customers of my clients that like literally changed my life.
The “All-In” Philosophy [16:22]
Shaan Puri: But it it worked out all right. I mean, I think at at the end of your career, I mean, you were killing it.
Ken Rideout: Yeah, so, so when that happened, I mean, when from the minute that happened, within two years, I was making like, I mean, not again, not sound like a narcissist and I don’t have a lot of money. I’m not a rich guy, but within two years I was making like $2 million a year doing things that to me were like, I didn’t even know what we were trading. I just knew people and I had relationships and they were just doing trades with me. I was living in London. I was running, uh, I ran 36 hours ago, I ran the Tokyo Marathon in 2:29:19 and the day before that, the day before that, Outside Magazine wrote an article, “How 51-year-old Ken Rideout runs sub-2:30 marathons,” and I saw the headline and I literally had an anxiety attack. I’m like, “Oh my god, the pressure is on.” I mean, I’ve run sub-2:30 three or four times, but it ain’t easy. And I know that that last five or six miles, the suffering and the darkness that’s coming with that, I can’t, it’s, it’s literally, physically the hardest things that I’ve ever done. It’s like your everything in your body, it’d be like if you’re driving your car and every single warning bell is going off, the radiator’s overheating, the oil’s low, you’re going to run out of gas. And you literally are like, “I can stop and no one would care.” Or I can push myself and know that I didn’t have another effing ounce to give. And that’s, it sounds cliché, it might sound corny, but that’s my process. That’s where I have to go to get to where I’ve gone to, to the point where guys like you with this awesome podcast want to talk to me. Like, I’m, I’m a regular guy. I’m a dope. I, I don’t see myself as special with the exception of being willing to die to get the most out of myself physically on these particular days, at races.
The Transition to Endurance Sports [17:17]
Shaan Puri: You’re an interesting guy and we appreciate you coming on. You’re uh, I’ve been following you now, I think since 2020 whenever you joined Teddy Atlas, uh, because I I I listen to that a ton and I know Sean has too. And so we appreciate you coming on. You’re uh, you’re different. You’re built different. You’re a different guy and we appreciate that. We like those types of people.
Ken Rideout: Well, I I want to say again, thank you so much. I really hope that I didn’t come across as uh too alpha or cocky. I just tried to be more than anything, I tried to just be honest, man. It’s like the the the world and the internet is so big. If you if you embellish or bullshit about something, there’ll be someone coming out of the bushes like, “That didn’t happen and this didn’t happen.” Because I know a lot of my stuff sounds sensational and crazy, but I’m like, I think if anything, at times I’m downplaying some of the stuff because I know it’s how crazy it sounds. But, um, yeah, anyway, I I do feel very humbled and honored to be here.
Shaan Puri: This is a place where cockiness and alphaness is actually appreciated. So, so even if you did, that would be uh, you know, right at home here. We just like when people are the way they are and not trying to manage. It’s at home because we, by the way, we don’t get a lot of cockiness or alpha, Sean. That’s why we like it. Yeah, we enjoy it. It’s a it’s a good change. You know, we’re a business podcast for the most part, entrepreneurship and uh you know, we’re we’re a bunch of people with carpal tunnel syndrome, you know, it’s it’s not a bunch of alpha males coming on the pod typically. Uh so so you know, I think there was some good stuff here for for mental strength, toughness, adversity, you know, basically uh what I think is the most important thing, which is the little managing the little voice in your head. And um that little voice in your head, you know, that’s who you you go through life with and I think that um you’re a great example of what happens when you really like, you know, work on that. And so, so thanks for coming on, Ken. I really appreciate it.
Ken Rideout: I would say this before I leave, like that voice in your head is not little. That voice in your head is all all powerful. The most powerful, right? It’s the voice in my head is the one that tells me to get high when I know I shouldn’t. The voice in the head, the little voice tells me to go run when it’s pissing rain or freezing cold and snowing. So that voice in your head shouldn’t be little, it should be big and it should be like screaming from a megaphone that you’re the best and you can do anything you want to do. And to your point, if you have a bunch of carpal tunnel guys here that like might consider themselves nerds and like intellects, good, because the one thing that you can control is your physical actions. Anyone can do what I’ve done. I promise you, I’m not special. I wish I had the intellect as some of these carpal tunnel guys because that’s the one thing I don’t have and that’s where I’m trying to overcompensate by being so physical that maybe my intellectual shortcomings can be overcome through physical intimidation and uh alphaness. But anyway, I say that in jest, but honestly, everything that I have is available to anyone. I’m just literally, the only thing I’m doing different than most people is physically is trying harder.