Ken Rideout

Quitting is harder than suffering

Ken Rideout frames elite endurance as a deliberate choice to keep pushing when every signal says stop, comparing the body's distress to a car with every warning light on. The point: you can stop and no one cares, or push and know you left nothing behind.

“And I know that that last 5 or 6 miles, the suffering and the darkness that's coming with that, I can't— it's, it's literally the physically the hardest things that I've ever done is like you, everything in your body would be like if you're driving your car and every single warning bell is going off, the radiator's overheating, the oil's low, you're gonna run outta gas. And you literally are like, I can stop and no one would care. Or I can push myself and know that I didn't have another effing ounce to give.”

Reality doesn't matter, only what you tell yourself does

Rideout's pre-race mindset rule: what other people think of you and even objective reality are irrelevant; the only thing that matters is the narrative you hold about yourself. He convinces himself he is a pro runner going for Olympic gold.

“I'm a big believer in mindset and what you tell yourself is the truth. Reality doesn't matter. Like what other people think about you doesn't matter. It's the only thing that matters is what you think of yourself.”

It's hard to beat the guy who wants to die to win

Rideout argues that in any competitive field there are too many rivals to win at half-effort, but once you go fully all-in on one goal, you become nearly impossible to beat. He applied this from running to his finance career.

“if you're not all in, there's just too many competitors out there that are gonna eat your lunch if you don't bring your A-game every day. But when you do dedicate your 100% effort to one particular goal, it's very hard to beat the guy who wants to die to win.”

Steal thisPick one goal and go genuinely all-in; effort alone beats most of the field.

He slapped a hazing coworker and it doubled his salary

Hazed on a late-90s NYC trading desk, Rideout slapped a colleague and got fired. But the junior Enron traders he covered told the senior traders, and a competitor offered him a job the next Monday at double the pay.

“But I was covering these young guys at Enron and they told the senior traders what had happened. And one of the senior traders who happened to be from Martha's Vineyard outside of Boston called me up, said, hey, I got a job. I didn't even know we had competitors. That's how naive I was. I didn't know there were other brokerage shops.”

From $80K to $2M a year within two years on the desk

After moving to an inter-dealer brokerage covering electricity trades, Rideout says he went from $80K to roughly $2M a year within two years, flying the Concorde between New York and London running commodity sales and trading at Cantor Fitzgerald.

“but within 2 years I was making like $2 million a year doing things that to me were like, I didn't even know what we were trading. I just knew people and I had relationships and they were just doing trades with me. I was living in London. I was running, uh, I ran sales and trading, commodity sales and trading at Cantor Fitzgerald out of London and Hong Kong.”

New products carry fat commissions until buyers wise up

Rideout's read on why he made so much in credit derivatives: when a product is brand new, commissions stay large because customers haven't yet realized how much they're paying annually. The edge erodes as the market matures.

“And at the time, when a product is new, the commissions tend to be big until people realize how much they're paying on an annual, monthly, or annual basis.”

Steal thisGet into a new product category early while pricing is still loose and margins are fat.

$262K in commissions in a single day as a one-man show

While a 10-15 person credit default swap desk celebrated making $250K in commissions in one busy day, Rideout tallied that he alone had done $262,000 in commissions, keeping 50-60% of it.

“dude, we had a huge day. We made $250,000 in commissions between like 10, 15 guys. So I said, hold on, let me see. And I start tallying up things. I go, oh dude, I, I was a one-man show. I said, I did, uh, $262,000 in total commissions. And I think I was keeping like either 50 or 60% of that. In one day.”

A functioning opioid addict for a decade before getting sober

Introduced to Percocet after minor ankle surgery, Rideout describes a 10-year opioid addiction where the drugs gave him confidence to mask imposter syndrome. He got clean through an outpatient detox right before adopting his daughter from Ethiopia.

“And I had a minor surgery on my ankle and I was introduced to Percocet. And the minute I took those Percocets and the opioids, I was like, oh, I have all the confidence in the world. No one can stop me. And thus began like a 10-year odyssey of being high 24/7”

Quitting Ironman taught him the emptiness of not giving 100%

In his first Hawaii Ironman, Rideout quit during the marathon, telling himself every story he needed to justify stopping, then cried walking back. The shame taught him the pain of quitting and that emptiness drove his all-in philosophy.

“And the run got hard and I just quit. I just stopped. I was like, oh, I'm, I'm dying. This isn't my day. I've like, I, I just told myself every story that I needed to tell myself to justify quitting. It's been a long year of training. You made it here. That's the big thing. And as I walked back to transition, literally like crying to myself, like crying, like real tears, like it just, it's so shameful because I knew I didn't have to quit.”

Do the one thing more than anyone and you'll be the best at it

Rideout's all-in rule: set aside the rare virtuoso outliers, and whoever simply practices a skill more than everyone around them will become the best in the room. He attributes his running results to running more miles than others, not talent.

“If you do something more than anyone else, I'm pretty sure you'll become the best in the world at it. If you wanna be the best piano player, there's gonna be people that are just virtuosos. So let's take out the outliers. But if you wanna be a piano player and, and, and there's 20 other people in your class, I promise you that if you train more than them and practice more than them, you'll be the best.”

Steal thisOutwork the field on one specific skill; volume of reps beats most natural talent.

Worked free for 3 months, then grew a fund from $2B to $5B

Lacking asset-management experience, Rideout offered to run business development for a friend's $2B firm free for three months. Over two years he helped grow assets from $2B to $5B and raised $35M then $150M discretionary funds after banks laughed them out of the room.

“And I said, okay, I'll work for free for 3 months just to see if it works. And again, every time I've been willing to take a bet on myself, it's worked out.”

Steal thisOffer to work free on commission-only terms to get into a room you're not yet qualified for.

Money alleviates stress but adds stressors you didn't know existed

Having made and lost money several times, Rideout pushes back on the idea that wealth equals happiness: when Enron collapsed his income dropped fast against a $10-12K mortgage, and at his richest he became a drug addict. Money removes some stress and creates new kinds.

“So money can alleviate a lot of stress, but it can also add stress that you didn't know, stressors that you didn't even know existed. And yes, it's easier to have money than to not have money. But if your only goal in life is to make money, I would say be careful what you wish for.”

What he has that some billionaires don't: enough

Citing the Harvard longevity study that relationships matter most, Rideout says the gift of his new life is the ability to cut out people he doesn't respect. The one thing he has that some billionaires lack is a sense of 'enough.'

“I don't need— the thing that I have that some billionaires don't have is enough. I have enough. I have everything I need.”