3 & Out - Ken Rideout's story, Will Lamar crash out, Could McDonald call offensive plays

Big show today—met Ken Rideout at the Super Bowl and knew he was my kind of guest: Boston tough, finance shark turned opioid addict turned world-class over‑50 marathoner with a wild, honest story and a new book, The Other Side of Hard, out March 10; we’ll hit his journey, then a quick mailbag, and I’m taking a short family breather before we ramp into combine season.

You went from a rough Boston upbringing to Wall Street money to elite endurance—how did that happen so fast?

I grew up blue‑collar in Somerville, worked as a prison guard right out of high school, played college hockey and football, then stumbled into a junior trading job after men’s league hockey; I got fired for slapping a guy who was hazing me, doubled my pay by Monday on a rival desk, rose fast, moved to London to run commodities—and a surgery lit a ten‑year opioid spiral that I hid while functioning at a high level.

What finally forced the change?

Right before my wife and I traveled to Ethiopia to adopt our daughter, I tried an outpatient detox, blacked out in the bathroom, and finally told her the truth; seven brutal days later I took Vivitrol, started running ten miles a day through withdrawals, and traded using drugs for chasing hard things.

You and Reggie Miller became trail buddies in LA—what’s he like?

He’s a cardio machine and a better human, the guy grinding alone at dawn who later wrote a beautiful blurb for my book without blinking.

Boston seems to breed grit and people skills—did that shape you?

I learned to do hard things while scared, got a thick skin in a neighborhood where money was tight and teasing was constant, and prison work taught me to read people fast because everyone’s gaming you; the mob was background noise as a kid, the real education was survival.

How real was the drug culture in finance?

I was an institutional trader, never told anyone I was high, and drifted through days on Percocet, Vicodin, and fentanyl while London trading floors ran on chaos and coke; today you see two extremes—wellness diehards and guys still burning it down.

Once sober, how did you go from triathlons to winning big running races?

I did Kona three times, moved to LA, my wife called out the selfish time suck, so I went all‑in on running and started winning, from Malibu to a televised Pasadena half, then a 2:30 win at Myrtle Beach the day before I turned fifty, and later swept my age group at majors like Boston, New York, Chicago, and Tokyo.

Did you leave finance cleanly or juggle both?

I kept working while stacking daily tens, then pivoted to raising capital independently for funds and health startups and built a brand business managing partnerships for top scientists like Andrew Huberman and David Sinclair, which let me align work with what I love.

Do you really run ten miles every day, no matter what?

Every day, logged on Strava—about four thousand miles a year—outside in anything from ice storms to desert heat; mid‑forties is perfect racing weather, and heat beats you up far more than cold.

Tell me about the Mongolia ultra—your first one—and how you won it.

I jumped into the Gobi March with a month to prepare, carried a self‑supported pack, bonked on day one, won day two with a ripped strap and a bloody arm, scavenged food as folks dropped, then on the fifty‑mile stage I shared water with the leader until med support arrived and still gapped the field by a huge margin to win overall; days hit around a hundred, nights were freezing, tents flew, and I washed clothes with bottle water, then jogged easy the next day to flush out the legs before a long flight.

Your story is fuel for anyone trying to change; set up the book and where you are now.

Everything You Want Is on the Other Side of Hard is for people eyeing a reset—sobriety, career, family, or a physical goal—and my message is simple: you don’t need special talent, just stubborn will; I coach high school cross‑country, feel cheered on by my Nashville community every morning, and after my wife beat breast cancer, the daily run means even more.

Appreciate you—shout to Jamie Horowitz for the connect; I’m lacing up after this, and if I’m in Nashville I’ll hunt you down for a jog.

Thanks for the platform; I’ll send a signed copy, and you’ve always got a couch here—even if I’m the worst golfer on a great course.

Mailbag quick hits: that 2008 Steelers defense was nasty and often overlooked, Big Dom in Philly is part fixer, part intel hub, and all trust; Lamar isn’t Russell—he’s a better passer, just keep him healthy and trim the hits; Mike Macdonald can’t call both sides—the bandwidth isn’t human; trading Puka only makes sense for a monster haul because elite is elite; eighth graders with NFL coaches still lose to varsity because the trenches decide everything; Darnold vs Hurts going forward hinges on Jalen’s legs—if he won’t run, his ceiling dips; odd Super Bowl winners exist, but Doug is my outlier pick more than Arians; last year’s Eagles edge this year’s Seahawks on depth and line play; and in the booth the coordinator calls it, a lieutenant feeds personnel, QC tracks tendencies, and the head coach nudges situations.

That’s a wrap—I’m off for a short reset, back around combine week; thanks for riding with us.