How This Millionaire Investor Became the World’s Fastest Marathoner Over 50

Opinions expressed by Entrepreneur contributors are their own.

Ken Rideout was a hard-charging, money-minting Wall Street player until a series of financial crises and opioid addiction almost ruined him. But rather than succumb to the demons of drug abuse and economic ruin, Rideout rode out the storm.

“Every time I’ve been in the depths of hell, I’ve turned it into a strength,” he says.

Rideout is now a successful investor and the world’s fastest marathon runner over 50. On the latest episode of One Day with Jon Bier, I talked to him about how he turned his life around, the importance of a never-quit mindset, and his five essential tips and tactics for living your best life.q

‘Showing up is so important’

Rideout has won countless races, including the 50-and-over division at the New York City and Boston Marathon. Recently, he placed first in the Gobi March, a grueling 7-day, 155-mile footrace in Central Mongolia.

But he says half the battle is just showing up.

“If I didn’t have the balls to go there and get on the start line, I would’ve never known that I could do this, and it has become like a crowning achievement for me,” he says of the Gobi race. “But guess what doesn’t happen? If I don’t go there, no one cares because I don’t win. I don’t know what I can do.”

Rideout emphasizes the importance of consistently showing up and putting in the hard work, whether it’s for training, pursuing new experiences, or facing challenges.

“Showing up doesn’t just mean on race day. The race itself is a beauty contest,” he explains. “The hard work has been done months in advance, in the rain, in the snow, in the dark.”

Related: I Ran a Marathon Without Training. Here’s What I Learned and How It Made Me a Better Entrepreneur.

‘Do things outside your comfort zone’

Rideout is all about pushing new boundaries.

“One thing that I’ve always done that’s been a huge strength is I will try anything,” he says. “I’m down to try just about anything.”

He tells the story of talking to his wife a few weeks before the Goby marathon after he was having second thoughts.

“I told her, ‘I think I can win, but do I really wanna go sleep in the desert for six days? I’m not a camper. I like staying in posh hotels. But she told me, ‘You are always talking about doing things outside of your comfort zone. You talk all this shit online. You should take your own advice.’ And as soon as she said it, I was like, it’s on. I’m doing it.”

‘Thrive in a routine’

Rideout credits a disciplined daily routine with helping him stay motivated and accountable for his fitness goals. He says establishing consistent habits makes it automatic.

“I missed my calling not going into the military when I had the chance,” he says.

His typical weekday routine consists of taking the kids to school (he has 4), and running for 90 minutes at around 8:30 a.m. He breaks for a shower and gets work done, and at about 4 p.m., he lifts weights for 30 minutes. Then, he takes his kids to Jui Jitsu and has a family dinner.

He says, “For people who might be struggling with motivation in certain areas, I can tell you that when you do something enough, eventually, it just becomes automatic.”

Related: The Power Of Routines

‘Learn from failures’

Rideout shares how quitting during an Ironman in Kona, Hawaii, in 2012, was his biggest bomb as an athlete, but it also changed his mindset.

” I quit. I just stopped on the run, just gave up like a big baby,” he recalls. “I was so disgusted with myself that it basically transformed my whole journey. I told my wife, ‘I will never feel this way again. I would rather be dead. I don’t wanna live like this. I don’t wanna live with this feeling. When I think about quitting that race after getting there and then disrespecting the race and all the people doing it in a weird way, it makes me feel like less than zero…I promise you I will f$%king die before I quit.”

‘Endurance is key.’

How does a former opioid addict in his 50s manage to outrace clean and mean athletes in their 20s? Rideout says it’s all about endurance.

“As you get older, you get mentally tougher. You have things more in perspective,” he explains. “When you’re younger, you’re doing so much. There are a lot of distractions and it’s great. But once you come to the realization that the clock’s running, then you start really focusing and optimizing for the things that are important to you right now.

“I still don’t think I’m a very good runner. I’m just trying harder than people.”