Episode · Dec 3, 2025 · 1 hr 48 min
Pills, Pain & Fatherhood
with Ken Rideout
Ken Rideout is a former pharmaceutical sales rep and Wall Street trader who discusses his ongoing recovery from opioid addiction and the role of endurance sports in his life.
“The only thing that can give you peace is your own mind.”
Summary
Ken begins with the Gobi March, a self-supported six-day race across 155 miles of Mongolia that he entered with four weeks to prepare. He had never run with a pack or camped, started too fast, and lost ground to experienced racers. After repairing a broken pack and adjusting his pace, he caught up, helped a rival through the desert and won the final stage. The race gives them a way to discuss competition, recovery and why he keeps choosing difficult goals.
He then traces his addiction from Somerville through pharmaceutical sales and Wall Street, where income and status did not stop him from using opioids. He says he moved to London hoping to outrun addiction, but the drugs followed him. His adopted daughter from Ethiopia became a turning point: he wanted to be sober for his family, went through outpatient detox and began using running as both punishment and structure. With Mishka Shubaly, he talks about raising four children with Shelby, learning from endurance sports, and finding that lasting peace comes from his own mind, not money or race results.
Show notes
This time I’m the guest. My friend, co-conspirator, and writer Mishka Shubaly turns the mic on me.
We go deep into my past—from the years I spent hiding an opioid addiction and living a double life in pharmaceutical sales and later on Wall Street, to the moment I finally chose my family over my vices.
Mishka traces the full arc of my story: the lies I told myself, the fear of getting comfortable, and the role endurance sports played in rebuilding my identity through hard work. We talk about honesty, identity, and how running became the tool I used to leave my old self behind.
This episode is a raw, honest look at addiction, accountability, endurance, and the ongoing work of becoming the person you’re trying to be.
Ken Rideout Website: theothersideofhard.com YouTube: @ken_rideout Instagram: @ken_rideout X: x.com/KenRideout_
Transcript
Made from YouTube's automatic captions and lightly corrected, so a few words and names may be off. Click a time to play the video from there.
Mishka Shubaly
You ready, bro?
Ken Rideout
I'm ready.
Mishka Shubaly
Dude, it's so funny hanging [clears throat] out with you in person because we've been talking like three times a week for the last year and I feel like like I'm meeting the Easter Bunny. It's you're actually a real guy. the um it it you know there's so and there's so many good interesting ways into your story, but I feel and I do want to get to your sort of origin myth, but I feel like the best place to kick it off. The one story that sort of encapsulates all the crazy unbelievable things about you is the Gobi March.
I mean, that sounds like it was just a crucible of suffering where it tested you at every turn.
Ken Rideout
Yeah, I feel like the Gobi Desert, the Gobi March in the Gobi Desert in Mongolia was like a [gasps] I don't know if a culmination of my life is the right description, but it's definitely reflects on all areas of my life from like being beaten down, feeling disheartened, feeling top of the world, and everything in between. But, uh, even from the moment I signed up for that race, I was like in a moment of, I don't know, bravado.
I was like, "Dude, I'll kill everyone at that race." And I and I reached out to the race director. I had talked to a friend of mine called Scott Daroo who was the um CEO at Equinox and he told me he was doing this race and I don't even know why. It just I just blurted out like, "Dude, I'll kill everybody at that race." You know, it's kind of like [ __ ] talking, but at the same time, I was like, I bet I could win that.
I don't know why. I didn't know anything about it. You know, I had never run with a backpack. I had never gone camping. I'm I mean, you know me, I'm like I am not a camping guy. I am a big [ __ ] in a lot of ways. Uh but I grew up roughing it. I don't want to rough it anymore. I want to stay at the Four Seasons. I don't want to be sleeping in a tent. But if you tell me that there's a trophy for the person at the end who can suffer the most, I'll sleep on a bed of [ __ ] nails.
And when he told me I could do the when when when I told him that, he said, "Go ahead and try and get in. It's in 4 weeks." And um I reached out to the race director and they were like, "Yeah, happy to have you."
Mishka Shubaly
I got [clears throat] to There's so many things here. the I mean you have like a an incredibly um mind-blowing resume as but as a marathon runner and primarily like a road runner. What what possessed you to sign up for a race like this on four weeks? I mean that's no time to train.
Ken Rideout
No. Um, I don't know. It just sometimes I've thought about this a lot because there are other really hard ad hard hard events that I would like to or would have liked to have done or would like to in the future like um Leadville uh uh Bad Water. For some reason that race just spoke to me and I was like I I I think I can win. I I want to do it. I was looking for a challenge and I had at that point I had won four of the six world marathon majors and this race was in I think the Gobi race was in like [snorts] June if I'm not mistaken and then I was doing the world championships in Chicago in the marathon in October.
So, I signed up for the race with four weeks and I just started ordering equipment, backpacks, multiple backpacks, which are which weren't cheap. And just working through and finding one that worked because they would just chafe you like crazy. Running 20 miles with 20 lbs in that pack was not easy. And uh I very quickly realized like, oh my god, what have I gotten myself into? I want to say the race was in June. Um, but yeah, I just started training in June in in Nashville with these with towels and bottles of water packed into the into the backpack to simulate what I would be carrying cuz it was a self-supported 6day stage race over 155 miles.
So, some days were like 21 miles and the longest day was 50 miles. And um as soon as I walked onto the airplane in Nashville getting ready to head for Ulaanbaatar in Mongolia, my had like a m a mindset shift of like from gone going from nervous and apprehensive to like I'm ready to kill. Like I was just getting myself pumped up and which sounds crazy. I still had like, you know, a 20our flight to go or 20 hours worth of flights. And uh I just started thinking about all the things that could go right and tried to like not focus on the things that can go wrong.
And uh when I got into Ulaanbaatar, I get to the hotel, which was probably one of the nicer hotels, but wasn't nice by any standard that we're used to in the US. And uh they were like, "Oh, your room's not ready." It's like, you know, in the afternoon. I'm like, "What the hell?" They're like, "But we do have one room where the people didn't show up, the honeymoon suite." And I was like, "I'll take the honeymoon suite." And I get into the room and there's like all balloons and heart-shaped things all over the room.
Mishka Shubaly
And you've been awake for how many hours at this point?
Ken Rideout
Oh, I slept a little on the plane, but I've been on planes for 20 hours. I was like ready to go to bed.
Mishka Shubaly
Yeah. You You've had a ton of success as a marathoner just by going out there and hammering it, just by being, you know, the hardest working player on the ice basically. and the but I feel like Gobi March was a whole new level of the um an event for elite ultramarathoners, seasoned ultramarathoners from around the globe and you were for some reason you were just like I'm going to make this hardest thing my first one.
Ken Rideout
Yeah. I mean even when I got there we were doing the gear check. I I realized my backpack was heavier than everyone else is. I didn't know what the hell I was doing. everyone kind of knew each other and uh that was crazy. They bust us out into the middle of the desert on like a um Sunday morning or Saturday morning and the race started the next day. So, we slept in a tent the first night. It was like raining sideways and I was like, "What have I got myself into?" And then the first day I just, you know, I made every rookie mistake.
I went out super hard, but thinking there's no way anyone will be able to run this fast. And many of them did. Like two guys in particular, an Israeli guy and a um Swiss guy. And they every time I looked around, they were there.
Mishka Shubaly
Mhm.
Ken Rideout
I couldn't get rid of them. And I'm like, Jesus, these guys are good. Cuz I was running fast, like too fast for a for a 21 mile stage. And uh getting towards the end of the stage, it was we went up the side of a mountain and they busted out their poles and just started power hiking up. I didn't have poles. Again, didn't really know what I was doing. And uh they just slowly pulled away from me. And I was like, it was like in slow motion.
I was like, I can't believe that they got away from me and I can't do anything about it. And then maybe with a mile or two to go, a third guy passed me. So now I'm in fourth place and I'm like, oh my god, this is like I'm going to be lucky if I can even get in the top three. and uh got into camp that night and was completely demoralized. I was like, "What the hell am I doing here? I hate sleeping in this tent.
The you know, all the food that I had to eat for the week was in my backpack. So, it was like all freeze-dried food. So, I'm trying to be strategic with the calories and, you know, burning like up to 10,000 a day and I'm taking in like 2500. So, I'm like just hungry the whole time. And now I'm also mad anxious because I'm like I'm going to get killed every day here. So then the next day was 28 miles. So I had gone out way too hard the first day.
So the second day I was said to myself, okay, no matter what,
Mishka Shubaly
Let let me back you up here. The you told people you were going to win this race, too. The that's
That's an important thing that's at stake here is that you weren't just like, I'm going to go out and complete this incredibly hard race. You were like, I'm going to win this.
Where were you in your head in that in the last quarter of that last stage when like when people are dropping you, you know?
Ken Rideout
I was thinking, uh, this is embarrassing. And I had like sponsors that were involved. I was like, I'm going to have to give this money back. Like, I can't take money. I can't let someone fund my like adventure tourism.
Mishka Shubaly
Yeah.
Ken Rideout
And uh,
So the second day I was like, "All right, I'm just going to be more strategic and just like it's a long day. It's a long race and uh, I'm not going to be stupid this time." Like, I've learn Okay, I learned my lesson. Plus, I had just gone off the plane like less than 24 hours before we started running. So, it was just I just made a shitload of mistakes. So, on the second day, I was like, "Okay, I'm going to take my time." And the two guys again, the Swiss guy and the Israeli guy, they got a a decent lead on me, but not much.
And I wasn't even paying attention to them. And then slowly I was catching up to them. And before I knew it, I was like running next to them, but again, no conscious effort to like on pace, just maintaining a steady pace.
And slowly, I just pulled away from them. And then maybe with like 5 to 10 miles to go, I was turning back and I couldn't even see them. And I'm like, I must have a onem lead on these guys. So then I started hammering. And as I'm hammering uh with like five miles to go is literally like being we're in a desert. It's like a mirage, you know? I see like a a Bedawin camp up ahead, like a nomadic uh like campsite with yurts. I'm like, "Oh, that's got to be the campsite tonight." Cuz I knew one night, the second night we were there, we stayed in yurts.
So the third the third night cuz the first night we didn't race. So, you know, it was the the night before the race. So the second day of racing, we slept in these really cool yurts. So I kept seeing these villages and I'm like, "Yes, I'm here and I'm hammering and then I get there to be completely abandoned." I'd be like, "Shit, the markers, the the distances are off." Which come to find out that's like not uncommon in these kind of races. Not to mention, you have to follow these little tiny pink flags that you have to almost be on top of to see.
So, as you're running across like a crazy like like uh rolling meadows, theoretically you could be going to the extreme right and not realize, you know, the flags could go way out and then turn to the right. So, if you could see them, you could kind of bear vear off to the right and cut a little bit of the course. You weren't technically supposed to, but there would have been room for that, but you can't see the flags until you're on top of them. So, a lot of times like it would be run up the side of the mountain and then run right back down 100 yards to your left where you could have been like I could have avoided that entire ascent and descent and just ran over there.
Mishka Shubaly
Yeah.
Ken Rideout
But if you made a mistake, you would be completely off course. So,
I'm looking for the flags, looking at the villages and with a few miles to go, I fell down. I just got going fast downhill, lost my balance and my backpack, the strap ripped right off the backpack like where it attaches like down near your waist from the shoulder. It just blew out and I was like, "Holy [ __ ] I'm winning and now my backpack is ripped and it's ripped in a way where I'm like, I can't run like this for, you know, for the rest of the race.
I'm gonna have to get to the finish today and then I'll have to reassess." So, I hobbled in there and when I fell down, like I my elbow cut open real bad. I'm just like bleeding everywhere. But my adrenaline was pumping. So, I was like, "Man, I am [ __ ] sore." But I I I'm I'm much I'm I'm probably a lot more banged up than I think I am because I know that my adrenaline is pumping.
Mishka Shubaly
Yeah.
Ken Rideout
And I finished uh maybe like eight minutes ahead of the next guys. But I was down like maybe 12 minutes, give or take a few minutes, but I was still down to the Swiss guy at this point.
In a race that long, too, the, you know, in addition to hammering your body physically in every way, a huge part of it too is like managing your your own mental game.
Mishka Shubaly
Yeah. the um [clears throat] you know that's the second day sounds like a really mixed day. Oh yeah
That you were able to get out in front of them and you know and win this stage and then you ate [ __ ] and the you know you were able to sort of watch that lead evaporate in front of you. Um the where was your head at the end of this?
Ken Rideout
I was definitely like questioning all my decisions because I won but I mean I was completely and totally destroyed. I was never so tired. I was dehydrated, bleeding. I mean, I was just smashed. Smashed myself. Which you would think, okay, if that was a marathon, I'd be like, okay, I smashed myself, but now I'm going to go home and rest for a few days.
Mishka Shubaly
Mhm. [clears throat]
Ken Rideout
But we've got to go to bed in this in a yurt on the floor, and then we're going to get up and like the next day was like scaling a mountain, like almost like rock climbing to start the stage.
Mishka Shubaly
You sent me a clip when we were working on the book that [clears throat] you recorded of yourself after that second day.
Yeah. Did you ever share that clip with the outside world?
Ken Rideout
No.
Mishka Shubaly
That's the, you know, one of the things I love about you as um as an athlete, as a storyteller, as a you know, a fellow, you know, sort of sober soldier is that you're so raw and you're so vulnerable. And in that video, we see you at an entirely new level where just everything's been scraped away, man. Like you look like you're about to keel over.
Ken Rideout
Yeah. I think as you know when you go through all of the level all the different stages of uh life when you're an addict you realize that no one is unique. Everyone is the same at their core. It's just a matter of what people are comfortable letting you see. And when you realize that you're not special, you're not unique. I mean, we all want to feel special and unique, but when you share your stories, especially like going through addiction and recovery, you realize like that's part of the whole like premise of AA is going there and sharing your experiences and your struggles and you realize like we have a lot more in common than we do differences.
And um if I've been able to do anything well since getting sober is just being honest with my feelings and my experiences. And uh although I haven't shared that clip widely on the on the internet or on social media, it's still like I'm not I'm not embarrassed by it or or afraid to share it. It's just like I don't know. Sometimes you just don't need everyone to know everything.
Mishka Shubaly
Yeah. Every single detail. the, you know, you do make a great point there that like, um, I think one of the, you know, for me with my drinking, um, I think one of the reasons that I clung to it for as long as I did is because it did make me feel special.
Ken Rideout
Yeah.
Mishka Shubaly
And the and but the way in which it makes you feel special is you feel like you're the piece of [ __ ] at the center of the universe. And then um and then when I stopped drinking, I was like, I'm just a dude now. Yeah.
That like I felt like I lost my superpower. Um the you know do you feel in in some ways that like leaving pills behind and getting serious about your running was you pursuing another superpower like a a healthier way to be special?
Ken Rideout
That that's exactly right. I definitely wanted a like a purpose and when I was getting high I was like yeah I'm getting high and no one knows like I'm I'm like I've got them fooled. No one knows that I'm like high on drugs 24/7. And what I've come to realize is when you I don't know if you if you felt like this when you were going through that late in an addiction, most people feel like this is like you'd almost rather be dead than be doing the drugs, but not quite.
And it's like even now a lot of times I don't want to say a lot of times I ideate on suicide but when I do ideate on suicide what I've come to realize is that it's not that I want to kill myself it's I want to kill something about myself some behavior. So when and and I think this is relevant for a lot of people when you're ideulating or thinking about like [ __ ] I just can I keep I can't keep doing this. What you're really saying is like there's something about yourself that you have to change.
You have to kill some part of your behavior. And I get it frequently. And when I do though, I have the peace of mind of knowing it's not that I want to kill myself. I want to kill some of these behaviors. And a lot of times we get so stuck in our ways, even in the errors of our ways, that we'd rather stay in that shitty pattern, in that shitty behavior, then run the risk of changing it and doing something different. People are so afraid of change that they'd still suffer in the in the place that they're in versus taking a step beyond and trying to find a new place in life.
Mishka Shubaly
Yeah. I mean, that's one of the things that I found when I got sober is that I was comfortable um being a dirt bag and I was comfortable being hung over and feeling like the world was against me. And it's it's a marter thing to tackle that new feeling of I'm just a normal guy with normal problems and like I spilled my coffee on my lap. It's not the end of the world. It's just a thing that happens sometimes.
Ken Rideout
Yeah.
Mishka Shubaly
When, you know, I've told people about you, um, you know, since we've been working on this book together, and, you know, people are like, "What? He's, you know, he, this guy's in his 50s. He's still running 10 miles a day. Like, why is he out there killing himself?" But I get it. It makes perfect sense to me because as addicts, we we have these we have a shadow life, you know? We have like our our life as human beings and then we have our life as addicts as the opposite of human beings and they run parallel to each other.
And to me, I feel like you're that's the guy you're trying to kill.
Ken Rideout
Yeah. Every time I am running, that's right. I am killing myself. I'm killing part of myself. I'm killing the part of myself that says, "Take today off. You'll be okay." Cuz I know that one day leads to two and there's a new addiction. And the new addiction might be laziness. And I know that not being lazy and by being out there doing these things, it does make me feel special and it does make me unique because I'm out trying hard and and I would be lying if I didn't say I appreciate and enjoy the recognition of being someone who works hard and you know for 10 years I was like in my mind I was like a piece of [ __ ] who was hiding a drug addiction from the world.
And it's like that negative selft talk going to bed every night knowing I've got to get off these drugs every single night. It's with you everywhere you go. Whenever you have a happy moment, you're like, "Yeah, but I'm addicted to drugs. If I don't have drugs and I get [ __ ] sent to jail or I get trapped somewhere, I'm screwed. Like, I can't live without these pills, I'll be deathly sick."
Mishka Shubaly
Yeah. It's funny that I I do worry about you sometimes with the crazy [ __ ] that you do. One of the things I've never worried about is you getting lazy. It's It's funny for me to hear that that's something that still uh that still bothers you. But I feel like for you, the thing I enjoy about running is when you it's over and you get to stop.
Ken Rideout
Yeah, me too.
Yeah. Okay. But I feel like you also, you know, that you just love doing hard [ __ ] that you seem to really finishing hard [ __ ] I That's the funny thing is people are like, "Man, I wish I was into running." I'm like, "I'm not into running at all. It's just something that I do." And it's like, I don't know if I can't imagine a life where you don't do anything that makes you uncomfortable all day. the thought of waking up and not doing anything all day and having a day off or a lazy day, I'm like, "Yeah, that does sound nice." But I know with my mentality that if I just lounge around all day, what if I do the same thing the next day and I'm so afraid of like falling into that rut and like I said, everything good that's happened in my life, the fact that I'm sitting here with you is because I'm out here working hard.
People know me as a hard worker. That's it. That that's my like that's my uniqueness. Like we all have like this ability to have something different about ourselves while we're all the same at the core. It's like what you choose to do with your free time. Like do you play video games? Do you run? Do you abuse drugs? And it just so happens that I found the knack for running and led me to places like the Mongolia the Gobi Desert in Mongolia, which is crazy to say that I went to Mongolia.
And that's another part of the reason when I was talking to Scott Daru and he's like, "Oh, I'm doing the Gobi March in Mongolia." I'm like, "Dude, Mongolia sounds cool. I love traveling. I love exotic travel." I did a race last year in Kenya, but um let me I'll finish the story with uh about the race in Mongolia because uh
Mishka Shubaly
Yeah. Yeah. How do you how do you pick up the pieces after that second day where you've like you've spent all you have for this entire week on the second day?
Ken Rideout
Yeah. Well, I thought I did, but what I realize is you can do so much more than you than you think you can. Another thing that I always try to remind myself consciously of in these races is that I'm doing this by choice. There are like special forces operators and soldiers and people that are doing this [ __ ] against their will that are in like major conflicts all around the world. And I'm like, how dare anyone complain about doing a hard race that they paid to be a part of?
Like I'm not going to die. And if I do die, then there something was obviously wrong with me to begin with. if I can't handle this compared to what like early man was doing before all like electricity and all the other [ __ ] that we have. So I try to remind myself of that and uh so the next day my bag's all ripped up. I I ended up like kind of maggyvering it together like I had zip ties cut through it, taped it all together and uh I get going on the second day and it starts like scaling up a rock face.
Like I I was walking I was going scaling past one of the race organizers and I'm like how the [ __ ] did you guys get insurance for this race? Like someone's going to die and they were laughing. They were like that's why it's not in the US. And I was like good point. So I jump down, get down and the Swiss guy is gone. like he scaled the rock so fast. He was like a real adventure racer, a really nice guy, super humble, quiet, Hugo Reinhold.
And there was another guy, David Dano. David Danu from Israel, Dudu we called him. And um so he was with me as we got over this wall and he was really funny guy, little guy. And uh we're running. I'm like, and my bag blows apart. And I'm like, "Oh Dave, my bag's [ __ ] ripped again. Damn it." Oh, man. But when it ripped, it had like a little stub of a strap on the still on the end. So I tied them together and I couldn't believe it but it held.
So it held for like that that that third stage was like 24 miles and um the Swiss guy beat me by about 5 minutes and now I'm probably down 10 minutes to him but I'm still comfortably in second and we slept out in like hardcore. Every night the campsites were a little bit different. Like I said the second night of racing we were in yurts. The third night we were in freaking sand dunes. I mean sand everywhere obviously. And I have some really funny videos that I made where it's like you can see storms rolling in across the like, you know, just rolling fields and mountainous terrain.
It was just gorgeous. But it was intimidating. And you could see the storm rolling in. I'm like, "Okay, that storm's coming in and about to dump [ __ ] rain all over our campsite." And I was like, "Oh, there's a huge wind gust just came through. Look, it threw those three tents out into the desert. I'm talking big giant tents." And I'm like, is this thing going to pick me up while I'm in the tent and throw me across the desert? I was like I So I wouldn't go in it until the the squalls passed.
The trucks that were moving all the gear was stuck in the sand. It was [ __ ] crazy. I was like, I can't believe I'm here. Why am I doing this? And I was making a video saying, "Yeah, this is like one and done for me. I'm never doing this again."
Mishka Shubaly
And you're not even halfway through it at this point.
Ken Rideout
At this point, we've done three days, but we've got the 50 mile stage, then the next day is 26, and the last day is like six miles.
Mishka Shubaly
So I I I know too that like um you know in chasing the the world marathon masters um record uh you've had some spicy competition you know going headtohead with a lot of other like really serious competitors. Um was there more camaraderie out in the desert that like you needed each other or that or and also you guys are suffering alongside each other every day?
Ken Rideout
There was definitely more camaraderie than a regular race for sure because you're living with people for a week. And um the guys like I I genuinely liked everyone there. Really nice Irish guy. Killian Ryan who I'm still in touch with. Just one of the after like the second day or first day, I forget. He said to me, "Oh, these guys know you're a marathoner. They're going to wear they said they're going to slowly wear you down." And I was like, "You don't [ __ ] wear me down.
I'm killing everybody." And this is even and this is after I got blown out. And he was like thought it was the craziest thing. And I was like, even after getting beat up, I was still like had the same like bravado of like, no, I'm still coming back.
Mishka Shubaly
Yeah.
Ken Rideout
So then after that day, after that night in the desert, the fourth day was the 50 mile stage and that's where like [ __ ] blew apart. So that's where like I broke the race open and uh we took off again. Me, the Swiss guy, and the Israeli guy and I was just feeling good. But I had like one headphone in that I had been like um squirreling away, you know, saving the battery on it to get your phone with you.
So I was listening to music on one AirPod
And I just ran over next to him and I was feeling real good and I said, "Hey Dave, yeah, did I ever tell you I never get tired." And he's like, "What? What?" I go, "I feel [ __ ] great. I could do this all day. I'm going to pick it up when we get a little bit further." And I swear within like a mile I looked back and he was walking and I was like, "Oh, I must I must have like mind effed him.
Mishka Shubaly
You broke him." Yeah.
Ken Rideout
So then it was just me and the Swiss guy and he was real I mean super stoic guy. Nice guy but like very few words. So I was almost forcing conversation on him at times cuz we're running and then they were like on the big on the steep inclines. We're walking together then we're running and it was like hey let's walk let's walk for a minute. Okay. You know there was we were together alone in the desert. The checkpoints are like maybe every 5 to 10 miles.
So you'd get water as much as you wanted to carry, but again, you have to carry it. So, you know, you would try to be strategic. And um we get about 35 miles in. We hit a last checkpoint and they surprised us. It was the only checkpoint during the race that had Coca-Cola and and Coca-Cola in a race to me is like crack. I was like, "Give me that [ __ ] Coke. I'm going to drink as much as I can. Sugar and caffeine and you haven't had anything.
There's no coffee or anything."
Mishka Shubaly
Y
Ken Rideout
And uh I came out of there feeling great. He came out of there feeling shitty. So, we were He was like, I'm going to walk for a second. I'm like, all right, I'll walk with you. Now, he's we're racing, but at the same time, I'm like, I don't want to like just run away from the guy. Now, I want to be by myself for 15 miles. I want to win. It's a weird feeling.
Mishka Shubaly
Yeah.
Ken Rideout
And he was like clearly suffering. So, I was like, I'm not going to desert him. Um, so slowly he just deteriorated quickly and then eventually was like, I got to sit down. And I'm like, dude, we're in the desert. You like you can't sit down here. So, I'm like trying to shield him from the sun. And I'm giving him like I'm pouring my water on his head. But he was a champ. I said, "Let me carry your backpack. Let's just get to the next checkpoint and you'll be good.
You get in the shade. They got water and ice and all that shit." And he was like, "No, you can't carry anything for me. I don't want to be I I'm going to keep racing no matter what happens."
Mishka Shubaly
Well, we got to set the stage here, too, because didn't somebody die doing this?
Ken Rideout
Yeah. A few years prior. Yep.
Mishka Shubaly
Yeah.
Ken Rideout
And they couldn't even get the guy out with the truck. They had to get him out with a camel. And it was a younger guy, too, wasn't it?
Yep. The sand dunes were treacherous. I've got great videos of those, too. I mean, hands and knees crawling up the sand dunes.
Mishka Shubaly
Yeah, that's I mean, that's the thing is that, you know, people accuse me of trying to kill myself when I go out to run 5 miles in Phoenix with my dog. You know, the that's that's one thing. This is complete. I mean, you are literally risking your life. And also, you're in this weird relationship with this guy who's who was a stranger until a couple days before. And now you guys are each other's lifelines. And also, that's your competition.
Ken Rideout
So, I'm helping him and and and doing all the right things cuz I like I say, I want to like win or die trying, but I don't want anyone else to die and I don't want anyone else to get hurt. Not at the cost of winning a stupid race that no one cares about. I know no one cares about this except me, but I care about it. Like, I you know what I mean? It's like I'm I'm not I'm not completely oblivious to [ __ ] life that like oh my god like it's not the Olympics, you know.
Um but anyway, I was helping him and eventually some support vehicles came by and we probably wasted an hour like sitting walking slow so people are gaining on us but we can't see them. We're so far ahead of everyone but still I'm like I mean second like I could put some time on everyone and lock this race up. And I'm like, you know, I hadn't even considered that I could win it up until this point cuz I was like, I'm never going to catch that guy.
Like after the third day when he killed me, I was like, Jesus, this guy's never going to stop. And um the support vehicles came by like a, you know, a Ford Raptor came ripping by and they were like, "Oh." And I was just like, "Man, where are you guys? Dude, someone's going to die out here. Like, you guys got to be checking periodically."
Mishka Shubaly
Yeah. Yeah.
Ken Rideout
I put my head down at this point now. I had been resting a long time because we had been walking and sitting and uh I just smashed the last 10 miles of the 50-mi stage and put 90 minutes on the next competitor and um you know that's race started let's say on a Wednesday morning. We didn't race on Thursday because not everyone not everyone finished in 24 hours. So some people like finished on Thursday morning. So, we don't race again till Friday, which sounds cool that you get a little rest, but I'm like, I don't want to [ __ ] spend another day in this campsite.
Like, I'm hungry. I've got like freeze-dried food that's salty as hell. All I can think is the crazy thing is I'm like practically killing myself in this race and all I can think about is like, man, the sodium content in this food is really high. Which shows you like the addict mindset of just like that's what you're worried about?
Mishka Shubaly
It's it's so silly like where our brains go, you know, that like you're out there like in these dunes that are like literally like eating you alive, but the the hardest thing for you was the camping aspect of it.
Ken Rideout
Definitely. Definitely. And the funny thing is the campsites at night were beautiful. And on the after the 50 milei stage, we got to this campsite. It was stunning. It was like a green field. It looked like Scotland. Parts of Mongolia were so unique. There were desert sand dunes that could be Saudi Arabia. There were like Scottishl looking highlands with like streams and tons of sheep. And then the fifth day, the 26 mile day, we went through mountainous terrain that literally looked like Switzerland. Pine trees, like stunning, gorgeous, dense forest up and down like mountainous.
And um the funny thing is the the creek would look so crystal clear. I was like, I'm getting in that damn creek cuz now you know you're dirty. They and they they asked you like, don't use the water that we provide to wash your clothes. You know, you got one set of clothes. I was like, "Fuck that. I'm washing my clothes every day." I put I had a little bottle of like hand soap and I'd rinse it all over me and have an Italian guy dump a bucket of water on me and then I'd hang the clothes up to dry and had a dry set of camp clothes.
But I went and sat in that creek in that creek and I was like, "Damn, what the hell's up with my legs?" I was like busting out in a hive. It was like instantly getting in the dirty ass water. Must have been like had like animal waste and [ __ ] in it. So I'm like, "Oh man, something's up with this creek." So, I go back to my tent and I'm like chilling in there on in the shade and I see like 20 people strip off their clothes and jump in the creek.
I'm like, "Yo, something's up with that creek." And they all come out and they all have like rashes all over them. It was hilarious. But there was a lot of good laughs with that. There was a group of Italian guys who weren't necessarily trying to win, but they were super cool guys like um journalists and uh one of their sons was volunteering. So the so the race staff would travel in their own caravan and the competitors had what we had for food and then the race support crew they had their own stuff probably in the buses and stuff and I was like convinced that these Italian guys had one of the one of their adult sons was working in the thing.
I'm like this guy has got to be like carrying food for them. One night I'm sitting there and they're like oh Ken you want a piece of parmesan cheese? I'm like you guys brought a [ __ ] cheese wheel with you and he's like oh yeah some put some olive oil on it. He had like a bottle of olive oil. I'm like, "You guys are carrying a bottle of olive oil and a [ __ ] a wheel of cheese." And they were like, "Oh, we got everything." But I'm convinced that there was no way.
But they were like such funny guys.
Mishka Shubaly
How good did it taste in that moment?
Ken Rideout
Oh my god.
Mishka Shubaly
I was like, I've been in races where they where you get like cubed potatoes. And I'm like, "What is this? This is magical. This is the best thing I've ever tasted."
Ken Rideout
It was mixed. It was really good. But I was like, "It's like a potato chip." I'm like, "I can't eat just one." I'm like, I'm like a cokehead. I'm like, as soon as those guys turn around, I'm going to eat the whole wheel of cheese. And I was like, what is wrong with me? But when we finished, they had pizza there. And like I pro, no, no [ __ ] I probably ate two in gigantic pizzas. I And it was crazy. But um so so starting on the 26 mile stage, I'm in a lead and uh I had the leader bib and uh we take off on the on the last real stage, 26 milesi.
And again, me and the Swiss guy are just alone off the front. And it's funny, the opening of the stage, we're running across this huge like pasture and there's wild horses and it's raining and it was just it was crazy. I was like, "Wow, this is like how magical is this?" Like I could be sitting in an office somewhere. Instead, I'm running across the like plains of Mongolia with wild horses.
Mishka Shubaly
Yeah.
Ken Rideout
And uh and then you can just see the mountains in the distance and all I could think was like, "Fuck, we're going to those mountains and we're going over them." And sure enough, that's what we did. And then the funny thing is with like a mile to go. So we're walking up the steeps and then we're running the descents. Again, not saying much and we get to the last descent with a few miles to go and this guy uh Reinhold, he just uh Reinhold Hugo was his name, not Hugo Reinhold.
Reinhold was his first name. He just took off like a bat out of hell. And if you've ever run with like real technical runners, even crosscountry runners, they are sick on the descents. It's like mountain biking. If you ever go mountain biking with someone who's good, like I went mountain biking in Aspen once with Lance Armstrong, and obviously he's a sick cyclist, but I was in good shape, too. So on the on the climbs, we're riding together, but he's strong, but he's obviously not Lance Armstrong to France Lance Armstrong.
He's like the other 50-year-old guy on a mountain bike, so we're good. We get to the descents, dude. It's like I'm on a tricycle and he's on a motorcycle. I'm like, how is he going that fast? It's like he's surfing the bike right down the mountain and I'm like tippy toeing down. Same thing with the running. This kid started blitzing down this descent where I'm like, "How is he staying on his feet? I'm running as fast as I can and I feel like at any moment I'm going to smash all my teeth out."
Mishka Shubaly
Running downhill is it's a very specific skill and like I had a couple people sort of teach me how to do it and then I call my sister and she lives in Idaho. There's no um
Ken Rideout
And she broke her leg cuz of you.
Mishka Shubaly
No. Now she kicks my ass whenever we're running down hills. It's like she she learned that skill and then just like took off with it.
Ken Rideout
It's like same thing with mountain biking. It's a skill. You have to know like technically what to do. But um he got away from me. But the road it finished along the side of a beautiful road next to this like flowing like rapid river. Not white waters, but it was flowing. And when we get to the end, it's probably 70 yards across and there's a rope tied to a Ford Raptor and a tree. And you have to hold the rope. And I'm like, "Oh, you don't have to pull the [ __ ] rope." Like, I don't need a rope.
That's for like That's for the other I let go of that rope. I almost got washed down the river. I was like holding on to the rope for life. And the water was probably like waste deep. But of course, when I'm in it, I'm like, "Oh, I'm already in this freaking flowing water. Let me just So I, you know, hold my backpack over my head. I dunk myself and the finish line's right there." So he had put like a minute on me. So I came in at that point.
I was like, "All right, I won. This this the last day was 6 miles, but I had 90 minutes on him." And uh
Mishka Shubaly
Did you did you ever like take a minute during the race to to sort of like take a take a breath and like relax and be like I've got it tied up now or it looks
Ken Rideout
After that last long day. What's the the night before the six mile stage? I kind of felt like that but not completely. And Killian said to me, the Killian Ryan Irish kid, he says, "Uh, yo, six miles tomorrow. You got this locked up. You're going to let someone else win this stage or you going to go?" I was like, I would rather die than let someone win anything. And I would never want someone to let me win. We're racing. And me and that Swiss guy got into a drag race and he could run.
And I end up beating him by like a couple of minutes. But it it came up and over a mountain and then down into this like Mongolian village and ended in this huge like temple like a like a wheel or like a walled city but not huge. And I just running in there I was like, "Oh my god, I did it. Thank god." crossed the finish line, ate like two pizzas, and then we got into the van for like a 6-hour journey back to Ulaanbaatar, which was harder than the race at that point.
I was like, I can't be around these. And there was I had no problem with the people, but I was like, I have got to be alone. I need some like time to decompress
And went back to a hotel. And uh that's when I finally was like, I laid down. I was like, I did it. Thank god.
Ken Rideout
This, you know, this is one of the things that blows my mind about your story is you do this thing again and again where you you bite off more than you can chew and then you chew it and you chew it faster than anybody else. and the and then the next day you get up and do it again. Like where does that energy come from? Where does that drive come from?
Yeah. No, that's a good question. I've been a me I was a mediocre loser for so long that when I got sober and started running and doing triathlons, especially with my buddy Rob Mo who's out there producing this, I was just like, "Oh my god, I found my people. I found people that have the same mentality as me that are like, "Yeah, it's cool to have hobbies and not everyone has to go there and try to win. I get it." But I never had a participant mindset.
I always had like a competitive mindset. I'm not here to like take part. I'm here to win, you know, to or or try to win. And I don't profess to be like the best at anything, but I'm going to try as hard as I can, and you will have to kill me to beat me. And that's maybe sounds hyperbolic, but it's the only way that I know how to like get [ __ ] done in my life. I have to like go 100%. I don't have any natural gifts.
It's not like I can just show up and be like, "Well, let me just [ __ ] around and win." No, it's like I have to like be dialed in and focus. I was talking about this with Rob more this morning about running races. I wish I could show up and just run a race and have fun. Like, yeah, I'm going to jump into this race next weekend. I'm like, "Oh, no, no. When When's the race? I need 10 weeks notice." Mhm.
It's a 5K. I don't care. Turkey try. I'm [ __ ] coming to win.
Mishka Shubaly
Yeah.
Ken Rideout
But, you know, growing up in uh when growing up in Boston, I just um I just was so into sports. I think, you know, I think my father wanted me to be a good athlete. And I hate to think that that still has any effect on me, but I just that was such a big part of my life. It was how I got validation as a kid. And I'm sure that there's an element of that that still takes part. But now I'm not really doing it for others.
I'm doing it for myself. Like I take a lot of pride in it. But you know, as a kid, that was the source of that that that was my way of like winning my father's attention kind of. And I, you know, my mother, we lived with my mother and um they they were divorced and lived town over, but my mother's side of the family was like more like drug addicts and and just shitty shitty situation. And my father was just by himself, so he could create whatever environment he wanted.
So he, you know, he always emphasized sports. And so to me, I was just like, "Oh, I I relate much more to sports than drug addicts." Which is ironic that I would end up being a drug addict. Although, albeit like, you know, financially successful drug addict. That was like my uh only saving grace. I was like, "Well, at least I can. I'm not robbing and stealing."
Mishka Shubaly
It does sound like you were a drug addict at a very competitive level.
Ken Rideout
I was the best drug addict. I could get like prescription painkillers anywhere. I one time went into a pharmacy in LA and convinced the pharmacist to give me 30 Percocets without a prescription, nothing. I was just like, "Oh, I lost my prescription bowl." And the guy was like, "Yeah, okay, here. 30 Percocet." I would go to Hawaii on a vacation, call a doctor to the to the hotel room and convince him to write me a prescription for Percocet.
And when I lived in London, I had a doctor over there who was like, you know, an alcoholic. And I could tell he was like, I gave him cash. He'd write prescription for anything I asked him for,
Which was like a big part of my undoing because when I moved to London, I was new to add to to my addiction. And I figured when I get to London, I wouldn't have access to the same people and the same doctors. But it didn't take me much effort at all to find the new connect over there. And I was like deeper in it than ever before. But um yeah, back back to the childhood when I when I when I stopped playing hockey and stopped playing sports, that's when like my life really like came not came undone but became a little bit less manageable and that's when I started drinking more and started doing coke in college and uh drinking and doing coke and then you know pills here and there with my buddies like I had been aware of pills but never really abused them and then moved when I moved to New So, I stopped drinking for a while, which allowed me to
Stop doing Coke. Cuz I never like was sober and thinking like, "Let's do some Coke." But it was always once I had like one or two beers that I was like, I'm definitely not doing drugs tonight. One or two beers later, I'd be like, "Call the guy right now."
Mishka Shubaly
Yeah.
Ken Rideout
We don't have any money. [ __ ] it. When he comes and we'll just take it.
Mishka Shubaly
Yeah.
In my sober life, it's like
Sobriety is the thing that makes all other things possible. And in my using life, it was a couple of beers that made all other drugs possible. You know that it like as soon as you get into it, you're into it. You know, and sometimes it ends four days later. Sometimes it ends 10, you know, 10 years later. So, one of one of the books that I did, you know, before working on this book with you was with my friend Mark Lanegan, and he's, you know, uh, he was, you know, incredibly gifted and like tortured, uh, soul.
And every time he spoke about his mother, it was like a shadow, you know, passed over his grave. And I feel like it's the same way with you. Do you feel like it was the pain of your childhood that drove you to to seek escape in in pills?
Ken Rideout
Yeah, I think that Yeah, I think that your early formidable years and the people you're around and the experiences you have kind of form your like the core of your personality and um as a as a child I was like identified as an athlete and and that was what I had that was what was mine when when when college sports ended that was almost all taken away and I was like I didn't really have an identity
And when I took the drugs especially opioids. I could be anything that I wanted. Nothing phased me. It was like just imagine if artificially you could feel the way you feel like when you get to the first day of vacation and you like check into some sick resort in like Bora Bora and you're in the overwater house and you jump into the water and you're there for 10 days. That feeling of like this is awesome. You could have that feeling anytime you want. Oh, you just got [ __ ] can from your job.
Take some pills. You'll feel awesome. The problem is when you're artificially spiking your dopamine and serotonin, all the other [ __ ] and in your brain,
When you get off those drugs for the longest time, nothing can replace that feeling. Like nothing makes you happy like that. Even being at the resort and actually being in the experiences that you envision as like the ultimate, nothing, it all pales in comparison. And that feeling sucks. So for anyone listening that's thinking about doing drug, don't do it to yourself. It's like don't even like tempt yourself. It's it sucks and it's like something that never like really leaves me and that part of it sucks and I hate that I feel that and know that and that's one of the biggest things that I struggle with is knowing that there is a great source of happiness for you but it it's it's temporary and it's only going to like if you're in a hole you can get out of the hole but when you get back in there it's going to be deeper.
Mishka Shubaly
Yeah. for I don't know four or five months when I was living in Brooklyn when I was using a lot I got into hydromorphone which is basically pharmaceutical heroin and the if I had to describe how it felt in one word I would say love
It felt like it felt like being in love and it felt like being loved and the and still having not used that [ __ ] in I don't know uh more than 15 years maybe 20 years I still I have dreams about at some like that [ __ ] has it maintains power over us regardless of how deep you know we get into sobriety.
Do you like me live in fear of relapsing
Ken Rideout
Constantly? And I and and again I'm not like the perfect um recovery story like I can't I can't say to you like oh this is the last time I use drugs because over the last like 10 or 15 years I've probably used drugs three or four times where I'm just like I I I need a break. They break usually initially when I got sober the break might last for like a week. Now I mean most you know in recent the the the time in between using it's it gets stretched out further and further and the time using is shorter and shorter where it might be like I'm just going to take pills one time.
Whereas before we'd be like, "Okay, I'm just gonna get a week's worth." Which sounds crazy, but
Mishka Shubaly
Yeah.
Ken Rideout
You know, now with kids and stuff, it's like in a family and when they did my children are old enough that they're like, "What the hell's going on over here?" Like I feel like I have a flashing red light above my head if I even like, you know, did any kind of substances. So, it's it's just at the end of the day, it's not worth it. It's just a temporary fix. And you have to realize that the only answer to your problems is you. you're the only person that can fix this in the long run.
And and but you can do it. I mean, in early January of 23, I went to a place called on-site workshops that was like a a 4-day trauma healing center. Basically, just four days of intense four or five days of intense psychotherapy therapy, like one-on-one days [clears throat] in a row.
That was like a complete game changer for me. It put so many things into perspective and helped me understand more about myself and my situation and and my relationships and uh that to me was like a big game changer.
Mishka Shubaly
You you said that you're not the perfect recovery story and I would counter that you are the perfect recovery story because you're open and honest about it and and the the narratives that we experience in books and TV and movies and stuff like it's rarely you know it's like I had an epiphany when I was 17 that I was an alcoholic and sure enough a short 15 years later I quit drinking.
You know that like and that's kind of how it works and I I mean that's one of the things I really admire about you is that you are so open and honest that it hasn't been a straight line for you and I think that's mimemetic of the experience that most of us have um you know with getting sober is that you know we're like oh I I can't live another day like this and then you live another 10 years like it you know the um so I I know from the work that we did together on the book that life in Somerville was pretty rugged.
You went from that the sort of um you know the alpha and omega from like poverty in Somerville to making it big in New York. Can you break that down? Like what how bad was it in Somerville and what what did it look like going from that to like when you were at the top in New York and how what kind of emotional journey did you take through that?
Ken Rideout
Yeah. You know, when you're going through childhood and in that in those circumstances, you don't think it's unique. Like that's all you know. It's like that's why I think about my own children and being little sponges and absorbing things as we go because they don't know anything different. They only know what I show them as as little kids. So, I didn't know any different, but I knew that it wasn't right. And I knew that like when we'd go through different towns and you'd see other houses, I'd be like, I want to live in a house like that.
I don't want to live in this triple decker in Somerville with heroin addicts downstairs and like people fighting in the yard. Um, so when I got out of Framingham State and and went to New York, I I moved to New York only because I got a pharmaceutical sales job and that was the route that that was available. That was the territory that was available in New York City, which was kind of crazy because you made the same amount of money whether you lived in Maine or New York City.
And like New York City rent was crazy. So I had a pharmaceutical sales job for about probably 6 months. I was the worst drug salesman in the world. It was like working from home before work from home was a thing. So, I would just I was so lazy. I would never get up and go to work. I'd work like a couple days a week, few hours a day. I had boxes from the floor to the ceiling in my in my little studio apartment of like pharmaceutical drug samples that I was supposed to drop off at doctor's office.
It it was crazy and I didn't really want to do that job. But very quickly when I got to New York and I was going to the gym, I was working in a place called the Vertical Club. It was like the Studio 54 of gyms. It was like neon signs, like you know, porn stars. It was crazy. It was like, you know, people were probably doing coke in there. It was a really wacky place, but it was a high-end joint and a big gym and there were a lot of people.
And I saw all the kids in there that like young guys that were making big money in finance. And I was like, Jesus, these guys seem like dopes. How are they making so much money? And uh I was playing in a men's hockey league at Chelsea Piers with a guy uh Mike Peltier who unfortunately died in 9/11 uh working at Cantor Fitzgerald. He had said to me he was working at a place called Euro Brokers. I think that's where it was. And they needed a trading assistant.
So he um he was like, "Yeah, you should come down and do this." And and sure enough, they were like, "Okay, yeah, you're hired. Come do this." And I didn't know anything about finance. I didn't know bids and offers. Like I when I say nothing, I didn't take a finance class. I knew nothing. But I knew how to talk to people.
And um I I enjoyed the job, but the people I was working with was such dicks. They were the worst people I've ever been around. Like I hated every single one of them except Peltier, who was like the cool French Canadian kid. And um and they hated me. I I don't know why. I don't know if they resent I don't know why they hated me, but they hated me. They were like bullying me and hazing me. you know, there was a big whiteboard where you would write the prices of different commodities on it like, you know, 20 bid for this.
And you're writing it down and I'm like, I can't keep up with this. I don't even know bids and offers. They're screaming at me all the time. And uh after like a few months, it might have been a few weeks, the I was talking to some young guys at Enron doing like some small like petty trades that had to be done every day. So, I had some kind of not clients, but relationships with these kids at Enron who were like my peers. They were on the trading side.
We were on the broker side. We were institutional broker. And the guy threw an eraser at me one day and I was like, "Oh, [ __ ] this guy. I hated him." And I slapped him across the I wish I could remember what his name was. I don't know. He was sitting next to Peltier. And only
Mishka Shubaly
Sure he remembers it.
Ken Rideout
Oh, only the three of us saw it. And uh sorry, someone else must have seen it because they fired me right on the spot. And um it was like kind of everyone heard it. And and then he was like, "What the fuck?" And I'm like, I'm going to kill you. Come outside right now. And long story short, they were like, Ken, you're fired. And I was like, oh my god. And every time this has happened in my career where I think something is catastrophic, it ends up becoming like a huge turning point like the addiction.
I was like, this is the worst thing that's ever happened to me. And I ended up by turning my life around created this story or opportunity to like share this comeback story with people and tell you like look at what I was able to do from where I started to where I finished. And I was making like 40 grand a year, which you know in New York City wasn't much. And um within two or three days the guys at Enron heard what happened. They told the big boss at Enron what happened and then people like loved it.
It took on a life of its own. And the next thing you know, 2 days later, I had a job making 80 grand at a competitor, which at the time I didn't even know we had competitors. And so now I'm like covering the biggest trader in the world at Enron. I'm doing trades like crazy. They're within a month or two they're like, "Your new salary is 125,000 and I'm getting bonuses of 50 grand." I mean, I'm like I'm now I'm rich and like very quickly. And around that time is when I had like a minor ankle surgery.
Got some Percocet. Took those Percocet and all the anxiety and you know going from no money to a lot of money was like created this like imposttor syndrome of fraud complex in me and I just felt super insecure about having the money. I was so afraid of like losing it. I felt like I didn't belong and at any moment they were going to realize I'm not supposed to be here. And in my mind I was like where else am I ever going to be able to make this much money?
I'm like almost prisoner to it. And when I took the Percocets, I was like, "Oh, I'm comfortable with all this. I'm cool with the chaos and I'm cool with the uncertainty." And unfortunately, they allowed me to function perfectly with confidence in work. And I my career just took off. And very quickly, I was hired by Caneritz to go to London and run European and Asian commodity sales and trading. And the only reason I went to London is because I had a contract with a competitor in New York.
So when the contract was up like a year later, they were like, "Then you go back to New York and you can run the New York desk or that would that was the that was the plan." And that was 9 then 9/11 happened like a few months after I got to London. So the whole office obviously got wiped out in uh 9/11. So, you know, being there during that was just absolute chaos and craziness and um you know, but I was I mean I could have very easily been in the building on 9/11 like so many of my friends including Mike Pel Mike Peltier who was there.
Um but yeah, and then and then I got to London and just started like jamming. But my a lot of my success in in that finance world was based on like emotional intelligence. It wasn't like no one was calling me for trade ideas. It was more about having good relationships with people and being likable and being trustworthy and like you know all the traits that you want to portray about yourself. You want to be like an honest person with integrity. And I know that there's a lot of people that your personality when you have a big personality like I tend to have is not going to mesh with everyone.
It's not going to not everyone's going to like you, which is fine. But the one thing I always prided myself on was my reputation of at least being a person of high integrity and character. Like I'm not I I've never been accused of wronging someone financially. I've never been involved in any litigation. And I'm like I'm just I just like always hustled and tried to do the right thing and and represent people with honesty and uh I haven't always treated myself with as much character integrity as I've treated my business.
But um going from Boston and and and being like you know poor to going to New York and having like s financial success was it was a roller coaster. And it sounds like everything you know on the surface again like the things that you think are detrimental end up becoming your biggest strengths and the things that you think are the greatest things ever can sometimes become like a thorn in your side. And having all the having making a lot of money really quickly like created so much anxiety in me that when I experienced those opioids I was like this is the feeling.
This allows me to be comfortable with everything. And it took a long time to like break that cycle. But having gone from those having been able to go from those two worlds, um it was crazy. On one hand, I could be completely comfortable after working in the you know, when I got out of high school, I worked in the prison as a guard for um several years while I went to college to be able to go from like walking around in the yard with like hardened criminals like black, white, you know, all different ethnicities to, you know, dealing with Wall Street CEOs and corporate leaders and corporate titans.
I've if I've done anything well, it's being able to move in between those worlds and and and and fit in emotionally at least. And that's again if that's if there's anything that I've done well, it's that ability to like kind of be a chameleon and like fake it till you make it and figure things out on the fly. From everything from the way you dress to the way people talk. I mean, when I went to New York, I look like a freaking mess. I had like a finan like a green suit that my grandmother bought me.
I mean, I thought it was the coolest thing ever, but it was like, you know, probably the kind of suit that like the British would call like a wedding suit, like a fun suit. It certainly wasn't like a business suit. I looked like a damn fool. I had like a brown brown belt and black shoes. Um, but I quickly quickly assimilated and recognized like what was what. And it's funny when I started making money and and when I went to London was when I really had a lot of money.
And I would go to like the Armani uh store on uh whatever the street is near Harrods and I would uh freaking buy a new Armani suit every couple of months. Like the best of the best again thinking that was what that was what I needed. That's what would make me happy. And uh as it turns out, it didn't do anything to change anything about me. I just look back at it and feel like a goddamn fool that I was like showing up like the sharpest dressed guy on a trading desk.
Like where who was I doing that for? or it was no one like for myself like my own vanity and it was like silly. Now I'm like can I just can I get away with wearing a black t-shirt and like khaki pants to this place cuz that's what I want to wear with jeans and sneakers. That was quite the experience and like I said there were a lot of examples there of things that I thought were going to be great that ended up becoming an a real thorn in my side and things that I thought were going to like derail my life ended up becoming like major positive turning points and a blessing in disguise.
Ken Rideout
There's uh there's so many things I want to talk, you know, talk to you about. The you and I both know a a ton of other like high-erforming athletic dudes who aren't interesting.
Mishka Shubaly
They they grind and they like and they win races and stuff, but there's there's just not a lot of like story there. And one of the things that's um most interesting to me is the ways in which I got you wrong when I first met you because the that [ __ ] Boston accent, bro. It like that makes me feel like I'm about to get jumped. And um and you know with your with your racing record, your performance record, having been a a Wall Street trader for as long as you did, you know, being such a successful guy, the I am surprised at every turn by how much heart you have and there's no better way to describe or there's no better way into the the level of emotional intelligence you have um than to talk about your kids.
Oh yeah. Because I know that just from hanging out with you, from being friends with you, from working on this book with you, that it's not running that's your north star, it's your kids.
Ken Rideout
Yeah. Yeah. You know, with the kids, I know how painful my own childhood was as a result of the people I was around. So, I've tried to like create a loving environment, but still tough like but still like emphasizing toughness, like tough love. So, I'm affectionate with them, but I can also be tough with them. And uh you know, at times it's like a real contradiction cuz I'll be like telling them, "Oh, come here, buddy. I love you." And then they'll do something like, you know, leave the house and mess.
I'll be like, "Who left this effing kitchen like this? Do you think that I should pick up for everybody or should everyone do their own or should one guy, me, do the work of six people? We all live in this house together." And I was like, he's five, but my kids are uh, you know, you always think your kids are going to be when I have kids, they're going to be they're going to be into this sport and they're going to do this and you realize that like it's like a box of chocolates.
You just get you never know which ones you're going to get. I have some that are tough and into sports, some that are um super emotional and like don't have any interest in physical contact whatsoever. like any physical, you know, combat sports,
The [clears throat] little one loves, you know, jiu-jitsu and wrestling and
But they all have their own uh they all have their own unique um personality and you just learn to foster the things that they're into, not what you're into. cuz I realized that as a child I was like doing mainly the things that you know mainly my dad wanted to do which you know I convinced myself at the time I wanted to do and maybe I did but I also know they were like where he got a lot of his validation and I was always hyper aware of not living vicariously through my children.
My kids don't have to be good athletes for me to feel good about myself and you see it all the time in kids sports. I do with this with the teams that they're on and some of the dads that are so into it. I will say where we live in in Nashville, just outside of Nashville in Vwood, the people are pretty good. There's not a lot of crazies. You know, occasionally you'll play some other teams and the parents will be way too involved. And I'm like, dude, chill.
The kids who are going to be really good, they'll let you know. You You don't have to tell anyone your kids the next LeBron James. He'll be [ __ ] Duncan in seventh grade. Like, you please like take a break. Let the kid relax a little bit. But, you know, you got the kids that want to play sports every day, and that's great. and and you know, you hope that they find something whether it's sports or not that they're passionate about. And that's all I've tried to emphasize with the kids is like you don't have to play sports, but you have to do something.
You can play guitar, you can take sewing lessons. The little one summer went to jiu-jitsu for a week, wrestling for a week, and sewing camp for a week. Only boy there, he did not care. He was like, the other kids were teasing him. He's like, "Dad, when I have my own clothing line, I'm not making anything for them. He's crazy.
Mishka Shubaly
That's awesome. Do you live in fear that one of them might go down the road that you did?
Ken Rideout
You know what? I've never even really thought about that. No, I don't because I don't think that they are I don't think that any of them there's I mean, look at I could do a lot of things differently with them, but at the end of the day, they live in a house full of love. They know that they're loved and supported. They know their dad's a freaking nut and can like go crazy about things, but at the end of the day, they know like I care about them like to a fault.
And um I don't think that there any of them are lacking like love or looking for validation anywhere else. I I genuinely don't. I could be wrong, but I don't I I've never worried about them
With drinking and drugs. I mean, I of course I worry like, geez, I hope none of them are into that. You know, it's like
Mishka Shubaly
Yeah.
Ken Rideout
It's like sexuality. You can't tell someone what you want to be. I can't be like, I hope all the boys marry girls and will that upon them. What if one of them likes dudes? Like
Yeah. You know, I hope that they find whatever they're happy, whatever they're into. Cool. I just I think when you're in it, you realize like you can't control what you can't control. When it comes to per people, they're they're [ __ ] people. They don't they don't belong to me.
Mishka Shubaly
Yeah.
Ken Rideout
They're their own people. And I'm just trying to like, you know, as they're little, they're like sponges. And as they get older, the sponge gets more and more expanded. And you just hope that those initial expansions and experiences are positive. So that the core of their experiences are positive and they have something good to build on and then the rest of it is all, you know, bonus. But that's that's all you can do when you I don't know. It's it's thinking about having kids and then having them is like night and day.
It's not what I expected.
Yeah. And I knew I know that that was like a driving force from you from very early on. Like you knew you were going to be a dad and that that was super important to yourself and to your understanding of yourself. Yeah, that's all I wanted to do was be a dad and like give kids a life that I didn't have. I didn't want to live vicariously through them. I just wanted to like I don't think it was show myself or show the world, but I just wanted to like prove to someone that I know what you're supposed to do and what you guys are doing is not right.
Mishka Shubaly
Yeah. Yeah. This is on a different level obviously, but the when I went through a really like rough, really dark patch during COVID, there were days where I was like, I I know that I can't do anything else and do anything for myself today. I I know that I can't be productive, that I can't do I can't go running, but I can make sure that my cat has a good day. And and that was one of the things that like that got me through is to look out for another being to, you know, to express care for another being.
And uh I honestly think that that being a good dad is the hardest, most important job that any man can take on.
Ken Rideout
So hard.
Mishka Shubaly
And you have four kids, dude.
Ken Rideout
So hard.
It is. It is the hardest job you'll ever love. But man, being a dad is not It's not easy. It doesn't come easy to me. I see some people that make it look effortless. [clears throat]
And uh it's just I don't know if it's because I'm getting older or my running habit, but it's just I am freaking destroyed all the time. Like I'm definitely getting my money's worth out of every single day.
Yeah. Um, but yeah, and then when I met my wife, to your point, when I met my wife, I told her that I definitely want to adopt some kids because I felt like the way that I grew up, I I wish that someone had taken me out of that situation at different periods of my life. And I knew that maybe I can be the person that changes someone else's life for the better. But, you know, you never know if what you're doing long term is the right thing.
Like we adopted a daughter from Ethiopia. Like I don't know. Is that the right thing? When people are like, "Oh, what you did for her?" I'm like, "Did I do anything for her? Maybe she did something for me. Maybe I was selfish. Maybe she was going to be the next queen of Ethiopia and I took her to the US to like live in Brentwood."
Mishka Shubaly
Yeah.
Ken Rideout
I you know, you you don't know when you're doing those things. You only know. My wife was on the same page with me when I told her all these things. So, we started the adoption process and we were just looking into like possibilities like could you adopt domestically, internationally? I wanted to adopt from a place where we could make a difference, you know, where where it was like, you know, I've always said that if you're born in the United States, like you can do anything you want.
Like we've had presidents that have like, you know, come from like not the like upper class and um so I knew being born in this country, using myself as an example, like you could be anything you want. You can do anything you want. Some countries, you know, you're born into an, you know, orphaned at a young age. You might not even survive. And when you go and see the orphanages in some of these countries, you're like, damn. And um so we had ended up adopting my daughter from Ethiopia in 2010.
And that was uh that was a huge transformative moment for me cuz when we were got the notice, you know, a couple months before we could go pick her up, I I I was like, I have to get sober. I can't keep doing this. I was on Subutex, you know, trying to withdraw from opioids, but I have been on Subutex for like several years, which you're supposed to be on it for a week or two. And um to me, getting off the Subutex, which is kind of like Suboxone, methadone, all those like detox drugs from opioids was like getting off that was harder than getting off the opioids.
Like cold turkey off the opioids would have been harder than stopping the subutex. It stays in your system for a long time. It's designed that way. It's why you're only supposed to be on it for a week or two. And I went to an outpatient detox and it was just hell on earth, man. I was I had to check in every morning. They'd give me my daily drugs like rolin to stay awake, Xanax to go to sleep, blood pressure medicine. It was crazy. And I needed everything.
I was so sick.
And that's really when I started running. And I just started running every day during that detox. I had been working out and like kind of running here and there. Even through my addiction, I'd run a little bit and I ran the Boston Marathon once in like 2005. I think I ran like a 330 marathon, but with, you know, which, okay, for some people is good, but I would eventually run an hour faster, more than an hour faster, just for context, like so yeah, I could run.
I was athletic. I would I would work out, but I could never like get the most out of myself. And and when I would finish at 3:30, I would be like on death's door, like barely able to walk and just like
So so I had been
Exercising but not like training like I wanted to I wanted to be good. And when I got went to the outpatient detox during that week, I started running as a form of penance both as like recreation and penance. Like I was like, I'm going to [ __ ] punish myself for what I've done. And I just felt so shitty. I was like, I'm going to die. if I keep pushing myself like this, I'm literally gonna die. But there was a part of me that's like, "Good.
[ __ ] it. That part of you needs to die." And uh, you know, I've told you this story before, but it was like four or five nights into this detox. It was kind of like the movie um, Flight with Denzel Washington. He's like crashed the plane drinking and driving. He goes, he's going to testify in court that he was sober and he's been sober for like three months. And the night before the trial, the door is open into his adjoining hotel room and it's the mini bar in there's full and he drinks the whole thing, calls the drug deal and he goes down to testify and he's like, "I did it all.
I was drunk. I was drinking and using cocaine when the accident happened and he goes to jail." And it was kind of like one of those moments where he was he was right there. He was home free.
Mishka Shubaly
Yeah.
Ken Rideout
And I was so close to being completely detoxed. Once I had a week under my belt, they would give me a shot of Vivitrol that was an opioid blocker that would prevent you from getting high. No matter what you did, you couldn't get high.
Mishka Shubaly
Mhm.
Ken Rideout
And [clears throat] I know cuz I tried and it just it was nothing. It was a waste of money. Like you wouldn't get get.
So with and I was almost there. I was like four nights into it and I woke up to go to the bathroom and I must have just blacked out while I was taking a piss. Woke up covered in piss. My wife is screaming, "What the [ __ ] is going on?" on and I'm come to him I'm like and just in like moment of like weakness or strength was like here's what's going on cuz she didn't know any of it and I was literally looking at her looking at the balcony.
We lived on like the 34th floor of this beautiful high-rise building and I was like I'm [ __ ] jumping off the balcony and that's when I was like why do I have to kill myself to fix this? Why don't I just fix the things that are ailing me instead of like I'm almost there. And then I just told her and tried to like make it sound optimistic like the good news is that's the bad news. The good news is I'm almost sober and I end up making it obviously.
Mishka Shubaly
And I I think when like the lay person at home thinks about, you know, sort of sobriety and epiphany and recovery and stuff that um they always imagine it to be sort of, you know, like a a rosecolored lightning bolt from God. and they don't realize that so many of those epiphanies involve waking up in your own piss. That's a hard lesson to take. The um
Ken Rideout
Especially when you know you did it to yourself.
Mishka Shubaly
Yeah, absolutely. And that's something that you know that's something that we have to carry with ourselves. You know the and like ultimately you you kind of have to forgive yourself but also you can't forget it.
Ken Rideout
That's right.
Mishka Shubaly
Yeah. One of the things to me that that also sets your story apart from other sobriety and recovery narratives is that you didn't quit using pills because you were going to jail. You didn't quit using pills because you had killed somebody drunk driving. You quit pills because you had because of a child you had never met.
Ken Rideout
Yep.
Mishka Shubaly
Break that down for me.
Ken Rideout
Not just a child I never met. I also quit for my wife and I knew it was not fair to marry this woman and not be able to give her the life she wanted. And I knew I couldn't do all those things that I needed to do while I was whacked out on pills. Like it just wasn't sustainable. And yeah, like I said, I was it was like I have to get I don't want I can't live like this anymore and I don't want to kill myself, but I don't know any other way out.
So, I'm going to try the last thing that I know how to do, which is get sober. And um as painful it was, I did it. But it's definitely one of when I think about the racing and running, it's like one of the things that I'm most proud of in my life because know it sucks that I'm proud of getting sober. Like there's a part of me that's like what a [ __ ] loser. But I can tell you that I know a lot of people that can't do that.
And I know a lot of people that haven't woken up the next day and haven't made it to the point where I'm going to get sober because they did it. They they took so much that they died. Many many people that I know have died and you know when you're talking about life and death and things that are like that kind of that level of like emot cuz you're not just physically suffering you know through these physical withdrawals the emotional toll is so so heavy and like I said I'm embarrassed that I put myself in that position but like what the [ __ ] I was there I had no choice but now to get out of it.
It doesn't change the fact that I still did it. You know, it's like when I see someone who's gotten sober from heroin or opioids, I think of like when you see someone who, you know, last year they were huge overweight and obese. The next time you see them, they look like a bodybuilder. You're like, "Dude, what the [ __ ] you? Look at what you did. So proud of you." I think getting sober is like that kind of feeling like, "Yeah, I shouldn't have got myself that out of shape, but I fixed it and I'm back." That's kind of like the feeling.
It's like mixed. It's like I shouldn't have been in there in the first place, but look what I was able to do. and then to be able to come and win these races. And I think that that's what's so important about not just my stories, but about all the stories that are told like on this show is like they comeback stories. It's like trying to provide people listening with inspiration or motivation to say like look at what this guy did. People should look at me and be like, if that [ __ ] idiot did those things, I can do that cuz there is nothing special going on here.
It's all up here. Everything is mental. I have no physical gifts. I mean, I'm not I mean I'm in shape because I work out twice a day every day. But I mean, that's available to anyone. And um honestly, I I genuinely believe like if I can do this, anyone can do this. Cuz there was a time when I didn't think that I could do anything of value. All I would do is do drugs and I had a good personality or good enough to make money on Wall Street and support my habit and live a comfortable life and fool if not everyone else at least fool myself into thinking that I was acceptable and my behavior was acceptable which it wasn't.
Mishka Shubaly
You know, I I feel similar way about my own sobriety where it's like the, you know, it's it's like, oh, we finally house broke the dog, you know, of like that's that's a bare minimum of what you want a dog to do is like not [ __ ] in the house, you know, the and it's and it took me forever to do it and then I finally did it and I I do feel a little sort of guilty and weird to get praised for it because it's like that that's the bare minimum, you know, but um but I know that we're wrong and you know, Like I know that it isn't the addictions that made us special.
What made us special was being able to finally put it behind us. Um do you do you have that like crystallized moment where it was just it it all became clear to you or was it was it an agonizing thing where you were like I I I got to quit. I'm going to quit tomorrow.
Ken Rideout
Well, I did that for 10 years. I knew from the beginning I was like I can't keep doing this. I'll quit Monday.
Yeah. or I'm going to start weaning myself off. Wean myself for one day. The next day I'd be like, "Fuck all this. I only took two a day. I only took two at a time four times yesterday. I'll just take five this morning."
Mishka Shubaly
I can't tell you how many times I rewarded myself for staying sober for 3 days, going out and having a drink.
Ken Rideout
Exactly. So dumb
For years. But then there were moments um where I can remember, especially when we moved to California. I had been sober a few years and I remember just driving on the PCH and thinking like, "Fuck, man. I'm sober. I don't I don't I'm not prisoner to any drugs and just feeling like I love my life." There's, you know, there's still moments like that, but I don't know. I've got to do a better job of managing my stress and emotions because it'll be like I'll wake up and feel like, man, everything's good.
And then I'll like run down a checklist to make sure everything's good. Like, are all the kids good? And I think about each one of them. What does this one have going on? If one has something going on, I have something going on. And it's like that's something that I really wrestle with. You know that expression like you're only as happy as the saddest child. Like that
[ __ ] phrase replays in my head all day every day.
Mishka Shubaly
Yeah.
Ken Rideout
Cuz I worry so much about them like from a emotional standpoint like are they okay? Is anyone like suffering with anything? you know, and it's I think it's also not just a burden on me, but a burden on them cuz it's it like that worry isn't serving anyone. Like you can't worry. I had um recently spoke to this Damon West and he said uh something about he he he was talking to um a a priest or a pastor about um praying and he was like, "If you're going to pray, don't worry.
If you're going to worry, don't pray."
Mishka Shubaly
Yeah. Worry is like the opposite of prayer. Yeah. You know, because prayer is like, I hope this good thing happens and worry is I fear this bad thing is going to happen.
Ken Rideout
That's right.
Mishka Shubaly
And and then it can just sort of like fill up your entire life.
Ken Rideout
I have to ask you a couple of tough questions, too, because I think that one of the questions that I have gotten saddled with, you know, a million times is people are like, "Oh, you just went from one addiction to another."
Mishka Shubaly
What's your response to that criticism? Do you feel like you've gone from one addiction to another?
Ken Rideout
Definitely like to a certain extent. Yes. But I also realized that one addiction had me wanting to kill myself and the other addiction allowed me to meet you, host this podcast, uh have a sponsorship deal with Reebok and Ran Apparel and Momentous and all the other great brands that I work with that I'm like
Mishka Shubaly
And your kids and your wife and your family and your beautiful house and your wonderful dogs.
Ken Rideout
Oh my dogs, bane of my existence.
Mishka Shubaly
That dude, that has been like the most heartwarming narrative arc for me getting to know you is like when you adopted Ruby and then seeing your your sort of internal demeanor towards dogs change radically.
Ken Rideout
Yeah.
Mishka Shubaly
Like it's like she just wormed her way into your heart and now you're stuck.
Ken Rideout
Yep. No, I know. It's like the dogs are like uh catch 22. like I love them some of the time and then some of the time I'm like these effing dogs if they don't stop barking. But um yeah, I know about the addiction is like no I'm I'm definitely aware of that and I don't I I don't try to um you know belittle the point um or or or minimize the the effects it has on others. You know, it's like definitely something that I think about.
But again, one addiction had me wanting to kill myself and the other addiction had me feeling like, all right, I just got to like keep it in perspective and you know, it's doesn't have to be done, but it does. But, you know, I try not to let it control or get in the way of anything else. So, I manage it the best that I can, but of all the addictions I've had, it's been the one that's served me the most.
Mishka Shubaly
Yeah. Yeah. The um one of the things that I really love and appreciate about my relationship with my dog is that um well, two things. Number one, she wants to run every single day. And number two, as as good communication as I have with her, there's no way for me to explain to her like, "Oh, we're not going for a run today cuz daddy has a tummy ache." You know, there's just there's no way to explain it to her. And the and I, you know, I made a contract with her when I took her in as a dog that like I'm going to take care of you.
Ken Rideout
Yeah.
Mishka Shubaly
Um, you run 10 miles every day, which is bananas. How? And you've done it for 5 years now.
Ken Rideout
More.
Mishka Shubaly
How? And you don't have a dog dragging you out to run every single day.
How do you motivate?
Ken Rideout
I'm my own dog.
Mishka Shubaly
You are. You are.
Ken Rideout
I again, back to all the things that running has given me. It's like that's my way of kind of feeling special. It's like, hey, this is what I do. Like everyone has their thing. I'm not really good at anything else and this is like the thing that I'm good at. And it's like my craft. It would be like someone who's good at music and you're like, "You haven't played the piano today? You're awesome." And it's like I know I'm not awesome in in relatively speaking when I'm thinking about Olympians or marathon real like marathon champions, but you know to the uh 50year-old guys over 50 like yeah, I'm I'm good at this.
And um it's a both a source of pride and a source of responsibility. I I I have to be foster my uh my gifts and and and not doing that. I don't know feel like almost like to a certain extent irresponsible
Like I I it's it's given me so much to to not run if I'm capable of running. I mean look, if you're injured, you're injured. Luckily, I haven't been injured to the point where it's prevented me from running. But, I mean, today as an example, it was it is so hot here. It's so humid and Rob ran with me and I was like, it was one of the hardest runs. And it's funny because, you know, I've done like, you know, I ran the marathon at 540 pace for 26 miles.
And I've done workouts where it's like 20 miles at like sub, you know, five sub6 minute miles, but it's the one that's like 820 pace for 10 miles and it's 95° and, you know, 80% humidity and I'm like, I can't believe I finished.
Mishka Shubaly
Yeah.
Ken Rideout
The whole way you're like, I'm going to die.
Mishka Shubaly
Yeah. It it killed me to not go with you guys this morning, but I knew that uh I knew that I'd slow you down. I knew that you guys would be running too fast for me and I knew that um yeah it would kill me. You you know you're a couple years older than me but you would still grind me into the dirt.
Ken Rideout
You would have hated I hated it. It was uh it was a brutal one.
Mishka Shubaly
The But you know the other thing is that you're an accomplished triathlete. I um I you know I try to avoid swimming whenever possible. I have a bike that I haven't ridden I haven't like set foot on in five years. All you know I've run every day this week except for today. Um when did you figure out that running
Ken Rideout
The day is not
Mishka Shubaly
I know. I know. I just I I those words left my mouth and I was like god damn it
Treadmill.
I would never run on a treadmill dude.
Ken Rideout
I mean I've only run on the treadmill like three I have like a $15,000 woodway treadmill. I've run on it like four times in five years.
Mishka Shubaly
I would never do that. the um but there's there was there had to have been some point where you figured out I I'm not a cyclist. I'm not a swimmer. I'm not a triathlete. I'm a runner.
Ken Rideout
No,
Mishka Shubaly
No,
Ken Rideout
No. I was loving triathlon and that's how I met Rob Moore. We had done Hawaii a couple times together. I think we both have gone three times. Um when I got into triathlon, I had I didn't have a bike. I never knew how to swim. I mean, not really swim. I could [ __ ] save myself if I was water skiing, but I wasn't like swimming laps. And um I was running and I had a an IT band issue in my knee and my knee was killing me and I bought a bike and some guys in the office that I was working in on the trading desk were into cycling and I went out cycling with them and they were telling me how great they were and we did a few laps of Central Park.
I had on like a sleeveless t-shirt, no helmet. I didn't know anything and I was like either these guys aren't very good or I'm like decent cyclist. And I was like within a week I had like the best bike at the shop, the all the matching kit like the NASCAR looking suit with all the sponsors on it. I looked like a real spaz and I just started training. I went to the New York Athletic Club, jumped into the pool and just started asking people for advice.
And at the New York Athletic Club had some of the best swimmers in the world. Like guys who were former Olympians working on Wall Street would swim there after work. And I would just jump in and be like, "Hey buddy, can you watch me swim down there and back and give me some advice?" And after a couple days, couple weeks, people were like, "Hey, what's up, man?" When you keep, it's like anything. If you saw someone at a writing workshop that was just there cuz they wanted to get better with no just for themselves, you'd be like, "Oh, hey, here's something you should consider." And you almost want to help them.
And I started to get decent at swimming, did some small triathlon, started to have some like decent success, and immediately was like, what's the best best triathlon in the world to do? Like the world marathon majors. Like I didn't want to run in small marathons. I wanted to run the best ones. And um you know, obviously it was Hawaii, right? That's the one that's on NBC Sports. Everyone's like, "Oh [ __ ] the Hawaii Iron Man." I'm like, "That's the one." You know, and it's funny.
I was telling Rob, man, it's so hot out today. But remember when we did Hawaii? Every single time you do it, you get off the bike around 12, between 12:00 and 2:00 p.m. in Hawaii and start running a marathon in the middle of the day and it's scorching. You run through the natural energy lab and it's all lava and it's just like a commercial like freaking shopping. It looks like a commercial parking lot, but it's all lava. And you just run out and back and it's just no wind and it's it's scorching hot.
And um I wanted to do that race so badly. And in 2012 I qualified and I went there. My wife came. I think we had two kids at the time and they were staying on a Ali'i Drive in a beautiful house. And as I'm running up like 3 miles into the race. I'm just like telling my wife like, "Cut, stop filming me. I I can't go on." And she's like, "What?" And I'm like, "I'm not going to finish. I'm I'm destroyed. I can't do it." And she was like, "Are you crazy?" And I'm like, "Yeah, I'm just going to go back and get my bike.
I've had it." And literally I was walking back like practically crying and like what the [ __ ] have I just done? And that decision right there is what like drove me to really focus on running and triathlon. I would go on to like I went back the next year did like a 939 which was you know decent. And I came in like fifth overall at Wisconsin Iron Man and like finished really high up in some other races. won my age group at the at a bunch of half iron mans and um went back.
But that feeling that I felt when I quit voluntarily quit was like a feeling that I can't describe. It was the worst feeling in the world. Like a feeling where I was like, "No, I'd rather drop dead on the raceourse than feel like this voluntarily. I just have to empty the tank." And then I would in 13 I went back and did 939. And then in like 15 or 16, I went back again. I was in the best shape ever. And like three weeks before I got pneumonia, like serious pneumonia, like in bed for a week.
And I was like, you know what? [ __ ] it. I've already qualified. I'm going to go. And sure enough, I went out there, did terribly. Got onto the run and was like barely able to run a mile at a time and finished in like 11 hours, but right before the sun went down, which was a moral victory. But man, I crossed the finish line there and I was like, I'm going to drop dead. Like I felt terrible, but I would never have given up.
I would have been like keep walking and been finishing with like a glow stick around my neck at night. But these are lessons that you learn and like, you know, thank God for all the endurance sports events that I did because they taught me so many different lessons. Same thing in Mongolia, like you just learn a little bit about yourself every day. And like I said, I don't know how people go through life with never having that level of discomfort where you're like, "Oh my god, is my body going to let me keep going here?" Like, and then you do it and you're like, "Holy [ __ ] I'm I'm tougher than I thought and my body can take a lot more than I thought." And you realize how much of this [ __ ] is mental and you can apply that to anything.
Studying, writing, it's just about getting focused and getting dialed in. And you can like will yourself to do a lot of things.
Mishka Shubaly
What compels us as human beings to tackle hard stuff, to do difficult things, to do you're the guy who does all the insane things like the why do you do it and what what does it do for you?
Ken Rideout
That's a good question because to me everything that that represents happens in the actual struggle of trying to finish whatever the task at hand is because like Mongolia, you would think, "Holy [ __ ] I won.
I'm going to go celebrate. I'm going to be so happy." I was happy for about a day and then I was like, "What's next?" Had I not won, I would still be agonizing over it and it would be like haunting me. So, what I've come to realize is that what you're really looking for is the lessons learned along the way. And it's like sometimes it's not necessarily a conscious thing, but it's like the preparation in the struggle. It's like gives me purpose. It gives me some like um it gives me structure to my day.
Like when I don't have something that I'm working towards and I'm just running to run, the runs suck. It's like I'm not motivating. I never like get out and feel like, "Oh, I feel great today. I'm going to run hard." When I'm in training for something, I'll be like, "Oh, I'm I'm on one today. I'm cooking." And and what I've come to realize is that the the the high that you're looking for is the struggle. It's like climbing the mountain is the victory. It's not standing on the top and being like, "I did it.
Of course you [ __ ] did it. You started. You shouldn't be surprised. is like spiking the football. Like, I scored a touchdown. I'm so surprised. Let me jump in the crowd. Like, no, you're paid to score touchdowns. You're a running back. Like, that's how I kind of feel about these things. It's like, yeah, you finished. Of course, you did. Like, if you didn't, you would have learned like, oh [ __ ] I was this. Things can happen along the way, and that's what you prepare for.
But, I don't know. There's a part of me that's like on one hand, it's it's like training training like you could never win and racing like you can never lose.
Mishka Shubaly
Mhm. [clears throat] the there is you know so much duality with training and racing you know the um I feel like um you know reaching the ascent of uh the reaching the peak of a mountain
It's about the ego
And the ascent is about humility
Ken Rideout
Yes
Mishka Shubaly
You know and so in order to be successful we sort of have to balance both of those you know to to say that like uh yeah I can do this I'm I'm hot [ __ ] I'm number one and also I'm I'm a humble student. I'm here to learn. I know that I know nothing that any of these people can beat me if I make mistakes. You
Ken Rideout
Well, that's the point about the Gobi Desert is like, yeah, the the bulk of what I enjoy telling people about are like the things that went wrong and the things that were hard. I never feel like, let me just focus on the day that I won the race and when I won and how awesome I was. And I realized that no one cares. No one cares if you come in for a second. My wife cares and my kids care like that. Did you win? Cool. And then within two seconds, they're like, "On to the next one." When the kids were young, they came and saw me win a couple races in California, like the Malibu Half Marathon and stuff.
And I'm thinking like, you know, they're still little. I'm like, "I won. My kids are going to want to come up on the medal stand with me and be like, you know, like I'm the [ __ ] conquering hero." And they're like, "Dad, can we go get donuts now? Like, do we have to wait for the awards ceremony?" I'm like, "I won. You don't want to wait for the awards ceremony?" They're like, "No." So, there's been many times where we've left early and been like, "Can you just send me the award?
I can't hang around."
Mishka Shubaly
I um I have to I have to ask you some of these like devilish questions that um I had I had a great conversation with your coach, Mario Foli, uh the other day.
Ken Rideout
It's the best.
Mishka Shubaly
And uh yeah, great dude. Um, and you know, we were talking about you and your train the role that he played in your life as a coach and um, you know, he said one of the things that he had to do was um, not to get you to work harder, but to go easier on yourself, to like to let up, to um, to allow yourself to feel happy, to feel grateful when you met your goals and stuff like that. And he told one story about I forget which marathon it was, but he told you that your mistake as a marathoner is that you were going out too hot, too hard, and then blowing up and not running the strongest second half that you could.
And he said that um at one race he was like, "All right, I'm going to be at the halfway mark at one at 114. If I see you come through there before 114, I'm going to turn around and go home." the you got to slow down or you're going to trash the second half of your race. And he was like sure enough like you know 11407 and Ken comes rolling through the So the question is this the How old are you now?
Ken Rideout
54.
Mishka Shubaly
54 physiology dictates that you can't keep getting faster that at some point you will have to slow down. You will have to like change gears and stuff. the you're such a smart dude. You have there's such a vast spectrum of stuff that you can do. You're so emotionally intelligent. What does the future hold for you?
Ken Rideout
That's a good question. I'm enjoying for one doing the podcast and talking to interesting people including you. I am I love speaking to people and telling sharing my story about like the highs and the lows and kind of providing motivation or inspiration of like I said earlier like if I can do this imagine what all you people can do cuz I guarantee you there are much more athletic people in the crowd and it doesn't have to be sports it could be anything like it took me you know I won the world championships at the age group world championships at 51 or 52 year 52 years old like you can do anything that you put your mind to.
And uh I'm testament to that. And you know, for my most formidable years from like through my entire 30s, I was like high on drugs and you know, didn't start trying till late 30s to like get my [ __ ] together. So I I really enjoy sharing the story, talking to people. Um I don't know. I've still got some physical challenges in me and and I don't think that at this point it would be I would be it would be difficult for me to run faster than I've ever run.
But that race Mario was talking about I think it was the Chicago race and when I won the world championships and I went through there and when I saw him I was like well there's a whole cool story about how I got how I won. But when I saw him I was just feeling good and I was like dude I'm on I'm on a good one. I feel good like I'm coming through. You know, sometimes you get through the halfway point, you're like, "Oh my god, I can't do this again." And other times you're like, "Okay, perfect.
I still got plenty in the tank." Um, and I came through and saw him and I was like, "I'm feeling good." And he was like very optimistic and encouraging like, "Just keep doing what you're doing."
Mishka Shubaly
Yeah. Yeah.
Ken Rideout
But in that race in particular, I I had started, this was in um I had run the World Championships right when I turned 50 in London. And um I thought I had won the World Champion the age group World Championships cuz no one in my age group had run past me. But as it turns out, a guy in my age group had started in a different section, which I don't think he should have done, but it is what it is. And he was up when when the three sections of the race mer they start in three distinct sections throughout London, and then they all merged together around three miles.
He had started in like a different section, which he technically shouldn't have, but he did. So, he knew he was in the race with me, but and I knew all the other people in the race with me, but I didn't realize he was in the race. So when we merged, he was just up the road from me like a minute, but I didn't know that cuz I couldn't see him cuz there were a few people up there. And um when I finished, I was like, "Yes, I won." And then I was like, "Oh my god, I came in second by less than a minute." So then I was like hellbent on winning.
And two years later, it was in Chicago. So at that race again I was started standing on the front of the start line just like bullied my way up to the front and I was there and everyone had their race numbers on the front and the back identifying their age group so you could know who you're racing in this race within a race and um 3 miles in roughly uh a guy who ended up being an Australian guy. I didn't know him at the time. I knew that there was one guy who the year before when I didn't run at the Worlds had run like 225, a Belgian guy named Tom and he was real good and he ran 225s three minutes faster than I've ever run.
Like I'm I'm I I I can't do that. I just know I can't. And um so I was like, man, if these guys do everything right, I'm I'm screwed. But you know, you never know what the race cost was like, what were the conditions, was it freezing cold as opposed to really hot, which makes a huge difference in performance. So, I was like, "Okay, let's go. I'm going to like win or die trying." And uh this Australian guy who I had no idea who he was just ripped past me at 3 miles going so fast that I was like, "There's even if I wanted to, I couldn't go with that guy.
He's flying." And he had also run, as it turns out, 225 that year. So, he takes off and then around 10 or 12 miles, the Belgian guy Tom rolls up on me and he's like, "Hey, let's go, Ken." And I was like, "Hey, what's up, man? Hey, there's another dude up the road in our age group. go get him. I wasn't encouraging him to like go crazy hard. I was just being a good sport. But I think what it did was made him work super hard to try to catch that guy.
And then around 20 miles I 21 miles, I see him on the side of the road stretching his hamstring. And I'm like, "Oh [ __ ] I'm back in this."
Mishka Shubaly
Mhm.
Ken Rideout
Sure enough, with like 2 miles to go, I see in an out and back section, I see the guy who passed me early running towards me going the other way. It's like a half a mile hit, but he's running fast. He wasn't struggling. At least I didn't think he was. And I just slowly started closing air on him. And and the crazy thing is the anxiety level goes up so much because I'm like, "Oh my god, I'm at the I'm I'm at the limit." Like if we get into a sprint, I can't sprint.
I'm going as fast as I can go. And I slowly eased up on him. And like with any racing strategy, like when you pass someone, you want to like pass them like you mean it.
And you know, really demoralized them. And I just ran past them as hard as I could, which wasn't very hard. relatively speaking and uh he couldn't respond and I glanced back with like as we were making the right turn in the Chicago Marathon there's a right and then a left within the last like half quarter mile and I glanced over and I like had a big enough gap and I'm like oh my god I'm going to win but I still wasn't 100% that no one else was in front of me I I thought that I understood but I did that in Chicago too
So I crossed the finish line and uh I saw a bunch of buddies there some running agents and and friends and they were Like and I was like, "Pull up the results. Tell me where am I in my age group?" And they're like, "Oh, it says you're number one." And I was like, "Fucking yes." Oh, I'm so relieved. And that like walking back to the hotel was like the best I felt after a race ever. I was like practically jogging back to the hotel like, "Yes, I did it." And I got my phone from the uh you know, morning clothes bags and I called Shelby and I'm like, "I won." And she's like, "Oh, congrats." And I'm like, "No, no, I won.
This was the World Championships. Like I won like I finally did it." And she's like, "Oh my god, I didn't even realize it. Like, why didn't you say anything?" I'm like, "I thought I did. I don't know. I just was like in my own little bubble training for this." But then she was like, "Oh my god, how happy are you?" And I was just feeling like I'm just so [ __ ] relieved that I that I did it. It's not even I'm happy, but I'm more like I just feel like I can breathe again.
Like I did it. I had a goal. I did it. And it's again like the happiness spiked and then dropped off just like a drug addiction. just like I did it and cool. I mean, I was happy. I'm still happy about it, but it's not like didn't change me. It's like same thing with money. People think if I had money, I'd be so happy. And I'm always like, I don't know about that, dude. I've had money and been broke. And uh money didn't change one being broke and being have money didn't change my state of mind at all.
Not even a little bit.
Mishka Shubaly
Yeah.
Ken Rideout
It allowed me to do certain things, but it didn't change who I was. when I sit alone or when I lay in bed at night, I don't have to worry about, you know, something that needs to be repaired or kids, you know, wearing new shoes.
Mishka Shubaly
Mhm.
Ken Rideout
But it's that that's not what life is about. You show me a miserable guy, I you give him money, I'll show you a miserable guy, a rich a miserable rich guy.
Mishka Shubaly
Yeah.
Ken Rideout
100%. Because there's plenty of people that are super happy, you know, living in a trailer. And and I always wonder, you know, you see a farmer in like Ethiopia and I'm like, is he winning or am I winning? This guy is like singing over there, happy as can be.
Mishka Shubaly
Yep.
Ken Rideout
And it's like uh I try to remind myself of those those thoughts frequently of like what what is winning? Cuz to me, winning is being happy. Being at peace, not even happy, just being at peace with yourself. And I find that to be like one of the greatest challenges is like finding peace. Getting to a place where you're like comfortable with everything. No one needs anything.
Mishka Shubaly
Mhm. [clears throat]
Ken Rideout
We always want [ __ ] But one of the things that I always say to people is like, you know, like using a watch as an example. I want this like uh super duper watch or whatever. And having had nice stuff. I'm like, I promise you that when you get whatever you want materially, you'll feel great for a week or two. Even with a watch, you'll wear that watch. trying think everyone's looking at your watch and then you'll realize no one gives a [ __ ] about this watch and you're still the same person you are.
You were you can you know it's like a drug addict moving across the country like I moved to London thinking I was going to outrun my addiction but guess what came with me? Me.
Mishka Shubaly
Yeah.
Ken Rideout
And that's the person who put me in this position. So no amount of material possessions can like give you peace. The only thing that can give you peace is your own mind. And this is what this is what all the running and competing and all these things are a big part of is like we're all just trying to find purpose, identity, and peace and just purpose in life. And um I don't know that all the running is the answer, but it's certainly better than the life I was living.
And that was a disaster. And I had plenty of money and I was miserable.
Mishka Shubaly
Yeah. Yeah. I uh I feel like we got it. I feel like this is a good place to get out with you um you know with what you just went through. But uh I want to I want to tag on two things. One is the first thing is I got to tell you I love you so much. I have so much respect and admiration for you like this this journey that we've taken together writing this book. It's just been it's been so rewarding and I can't wait for this book to drop.
And the other thing is I just want to like steal a line from Mario. you know, the line that he gave to you when you were halfway through winning the world marathon majors and to just tell you, you're on the right track, man. Just keep going.
Ken Rideout
Yeah, man. Well, thank you. It's been awesome writing the book with you when you're wizard when it comes to writing. When I see the pages when we've that you've written sometimes I'm like, "That's me. That sounds like me." And even Chubby was like, "Wow, it sounds like you wrote this." And I'm like,
"Yeah, it's like that's what a master uh writer does." So, thank you for uh being part of the journey. It's been awesome working with you and thanks for doing this. It's been uh it's been great and I hope people, like I said, realize that like this the the the fight is not over until you win or quit. And uh it's much more fun winning than quitting because I've done and I've done them both. So, keep going. Boom. All right, guys. I hope you enjoyed that conversation as much as I did.
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You can learn more about me, this podcast and also find links to purchase my upcoming memoir at the other sideofhart.com. My new book is called everything you want is on the other side of hard and it comes out March 10th available everywhere you buy books or again go into the otherofhart.com. There's multiple links there where you can find all the retailers carrying the book. Thanks a lot for being with us and we'll see you next
Key takeaways
- A race result fades quickly, but preparation and difficult work can give structure to daily life.
- Changing a destructive pattern may mean changing the behavior underneath it instead of trying to escape to a new place.
- A parent can support each child's interests without asking that child to repeat the parent's life.
- Honesty about addiction and setbacks can make recovery stories more useful to other people.
- Money can widen your choices without giving you peace or changing who you are.
- In an endurance race, helping a competitor can matter more than protecting a lead.
Nowhere to Hide
A weekly letter from Ken Rideout about doing the uncomfortable part, and the reasons we use to avoid it.
It starts with 3 Days, 3 Hard Things: one short story from Ken and one hard thing to do, every day for three days. Then one letter a week.
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