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Chapter 1: What life experiences shaped Ken Rideout's journey?
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Chapter 2: How does Ken define winning and success?
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All right, welcome back to the show, everybody. So I got to tell you something. My son sent me this man's book and his story, and I instantly, I knew I had seen him before. I said, I want him on the show. He's like a renaissance man. His story's bananas.
Chapter 3: What are the common misconceptions about personal limitations?
So today is going to be a ride, you guys. And I have to tell you something. Think of a picture of this. We're both Boston boys when we were little boys. Both grew up around a lot of dysfunction. I thought I saw like kind of a brother in him.
Yeah.
Kind of drugs and alcohol everywhere in his family. And then he's got this crazy life. Like he becomes this kind of Wall Street trader guy, Cantor Fitzgerald. Then he becomes an opiate addict, right? So there's that part of the story. Then he starts doing like marathons and ultra marathons. This guy's the fastest dude in the world, over 50 years old, running marathons.
He's completed the Gobi March. It was a 155-mile crazy race. And then he's like connected all over the world.
Not just completed, I won it.
Well, he won it. Thank you.
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Chapter 4: How did one decision transform Ken's life?
Not only did he complete it, he won it. And we were talking about this off camera too, about how he did that. So today it's going to be interesting. If you kind of want to remake your life a little bit later, he's remade his life multiple times. So this is for you. If you're overcoming some sort of thing in your life that's holding you back, it's for you.
And if you're young and you want advice from someone who's lived a full, complete life in his early 50s, Ken Rideout's your guy. His book is The Other Side of Hard, and this is going to be a great conversation today. Welcome to the show.
Thanks for having me. I appreciate it.
Yeah, I want to make sure you do give you credit. You did win the race.
Let's make sure that we do that. I'm teasing you.
No, no, it's awesome. So I got to, I have like, I don't do this in most interviews. I have probably like 60 questions and we're probably only going to get to about 10 of them because there's so many different things I could ask you. But I want to, the first thing is this, like when I think of you, I think of like, all right, probably mental toughness is probably the first thing that I think of.
How does somebody know, like you're talking about this hard thing.
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Chapter 5: What role does effort play in achieving goals?
How does somebody know I should quit or I should keep going? Like in a race, in life, after a business? Because not all quitting is bad. So I kind of want to go the antithesis of what's in the book. Someone's listening today, they're thinking of quitting a relationship, quitting a business. How do you know what's quitting and what is pushing through what's hard?
Great question. And to summarize, I would say, don't quit. I mean, there is a difference between quitting and knowing when to throw in the towel when you're like losing in business or, or, or a relationship in particular, right? You're in a relationship. Like you should know, like, all right. But there's a difference between having some intelligence and
pushing through and persevering when things are hard because nothing in your life that you've, that you'll, that's worth attaining is going to be easy. None of the success you've had has been easy. It's not easy being in shape. It's one of the things that's nice about showing up in shape. Like we were just talking about when you walk in and they're like, okay, this guy's in shape.
They know about 10 things about me already that at least I have grit, determination, delayed gratification and all the things that go with it.
Chapter 6: How can someone rebuild their identity after setbacks?
But I can tell you that when you quit, when you, You know when you're quitting, and I can tell you from experience, when you quit, the sting of quitting will last with you for the rest of your life. The first time I qualified for the Ironman in Hawaii on NBC Sports, it was so hard to qualify.
Only 2,000 people out of hundreds of thousands try to qualify, and it's the best of the best, and everyone's good. And I got there and I was so happy just to be there. For me, at 40 years old, it was like qualifying for the Olympics. But you qualify in your age group, so it's all relative. And I get there and it just got hard when I got off the bike.
I got onto the run, it was hard, and I just quit like a dead dog loser. My wife was standing there recording the minute I quit.
she's recording yay go and i'm like cut i'm like i can't do it i'm too tired and she was literally like what are you crazy really just keep walking and i was like i was part of me was embarrassed i wasn't doing well so in my mind again this is where you need mental toughness my mind was telling me it's okay you're not gonna win like come back again another time but meanwhile my wife has like put up with all my selfish training for years she's like this is it after this
You did it. You reached your goal. We're done with this. So I also knew this was probably the last chance. She would let me go back and do it again because of the disaster that I created for myself. But that sting of quitting on that day in Hawaii, I get emotional thinking about it now. I'm so ashamed of myself. My wife would say, who are you embarrassed in front of? Myself.
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Chapter 7: What strategies help in knowing when to push through or quit?
And the only opinion of me that matters and that should matter is my own. Because if I don't think highly of myself, why would my wife think highly of me and respect me? And I really... Some of this stuff sounds corny and cliche. I get it. But if you don't think highly of yourself, trust me, no one else will either. You have to be your own biggest advocate.
Let me ask you that. By the way, it's not corny from you. Here's why. Because you've actually done crazy things in your life. I'm being serious. There's a lot of people online or that have books that they say, maybe I'm even one of them, say a bunch of motivational stuff or whatever. But you've lived this. Yeah. I'm picturing you in the 143rd mile in this Gobi Challenge. I'm picturing this.
I'm picturing you trying to overcome this addiction. I'm picturing you where several of your friends are blown up in the World Trade Center on 9-11. Make your life's bananas.
Chapter 8: What advice does Ken have for those feeling stuck in life?
So let's stay on this thing about, because I'm a big believer, most of your life you're going to get what you believe you're worth and you deserve, this identity thing. And you talk a lot about identity in the book. And you and I both come from an upbringing. In fact, I'm talking to you today. I think it's a blessing. Today, as we're recording this, it actually would have been my dad's birthday.
And he was a central person in my life. There was addiction there, as you know, and some other stuff. But I think it's hard for people when you weren't raised being poured into You're great. I love you. You're incredible. You can do it. Or you don't come from winners. So most people listening to this or watching it relate to that to some degree what you and I grew up with a little bit.
And you somehow powered through this where you were not only – in his upbringing, if you read this book, you guys, not only was it not successful – It was, they were pounding into you the reverse that you were great most of the time. Yeah. And doing harm to you. Even your mom, you know, and many times, God bless her, but even your mom. How does somebody begin to, this is a hard question.
I'm giving you all the hard stuff today since it's the title of the book. How does someone start to change their identity? They're listening or watching like, I don't feel good about me. Yeah.
Well, I will say from my earliest childhood memory, I didn't feel like I belonged in this like house of horrors that I was living in. Right. I was constantly they beat the shit out of me all the time. There were always people doing drugs, fighting. It was violent. It was anxiety ridden because even as a kid, I remember thinking like, how am I related to these people? I'm not supposed to be here.
And It's crazy. Like if someone believed in reincarnation, they'd be like, oh yeah, he's reincarnated and came from a normal situation and now he's dealing with this. So growing up, I always knew the right thing to do. Like I didn't have any rules. I could come and go as I pleased. Like my parents weren't like, get in before the lights come down.
Like I could stay out all night and do whatever I wanted, but I never did those things. I was like a good kid. I got along with the principal of the school. Like I was the quarterback of the high school football team. I just instinctively wanted a better life for myself. And I was like pretty happy with myself and not arrogant, but I was confident.
And as you've seen in the book, then I get into New York and we'll get to it. And I get addicted to drugs and all of those positive things that I thought about myself were like stripped away. And I was like, really had a negative self opinion of myself to the point where I would ideate on suicide where my addiction was so bad.
I was like, if I don't get sober, I'm not living like this anymore, because I'm not a loser. But my behavior is that of a loser. And to your point about the book about giving advice, right? My book isn't a how to I'm not telling people do this to that I matter of fact, I say to a lot of people don't do what I did. Like I was a drug addict. I thought money was the answer. I got rich.
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