#881: Tales of Overcoming The Odds, and How to Turn Losses Into Wins — Tim McGraw, Terry Crews, Dax Shepard, and More

September 4, 2026

AI Summary

5 min read

When a Missed Layup, a Wood Album, and a Failed Movie All Turned Into Wins

In 1986, Terry Crews was a high school senior, the starting center on a basketball team picked to go all the way to the state championship. With five seconds left in the district final, he intercepted a pass, drove the length of the court, and went for the winning layup. The ball rolled around the rim and fell off. His team lost. His coach blamed him. The local paper named him. For days, he sat in shame on his bed, replaying the moment. Then a different voice surfaced: I took the shot. When everything was on the line, I took the shot. That reframe — not "I failed" but "I went for it" — became the organizing principle of his life. "If I win or if I fail," he later told Tim Ferriss, "it's going to be on my terms."

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What you'll learn

1 (00:02) **Episode Introduction** - Tim Ferriss introduces a compilation episode about overcoming mistakes and failure, featuring highlights from multiple guests.
2 (01:08) **BJ Miller: Riding a Motorcycle as a Triple Amputee** - The palliative care physician and triple amputee explains the years-long quest to ride a motorcycle.
3 (05:18) **Terry Crews: The Missed Layup That Reframed His Life** - The actor and former NFL player recounts a high school basketball failure that became a defining lesson.
4 (13:32) **Ad Break: iCogni** - Tim Ferriss recommends iCogni for protecting personal information from scammers and identity thieves.
5 (15:00) **Ad Break: Gusto** - Tim Ferriss promotes Gusto, an online payroll and benefits software for small businesses.
6 (16:17) **Tim McGraw: The "Wood" Album and Rebuilding on His Terms** - The country music star shares how his failed debut album taught him to take charge of his career.
7 (21:35) **Tim McGraw: Legal Battles and the "Monkey on the Dog"** - McGraw describes his darkest career period and how he rebuilt momentum.

+ Full timestamped outline available in the app

Show Notes

This is a special episode about overcoming mistakes and failure. What do you do when your work is rejected, when the big bet fails, or when the path ahead suddenly disappears? As you’ll hear in this episode, setbacks can often present opportunities, if you know how to look for them.

This episode is brought to you by:

Helix Sleep premium mattresses: HelixSleep.com/Tim (20% off any purchase)
Gusto simple and easy payroll, HR, and benefits platform used by 400,000+ businesses: Gusto.com/Tim
Incogni, which removes your personal data from the web, helping shield you from fraud, scams, and identity theft: Incogni.com/Tim (use code TIM at checkout and get 60% off an annual plan)

In this episode:

BJ Miller, a triple amputee, on his years-long quest to ride a motorcycle.
Terry Crews on missing a season-ending shot—and the mindset shift that stayed with him for life.
Tim McGraw on his debut album flopping and betting his career on next steps.
Jessica Lahey on being told her first book was “unpublishable” and turning brutal feedback into a New York Times bestseller.
Dax Shepard on the collapse of an identity and career he thought he wanted—and the unexpected much better life it made possible.
Cathy Lanier on becoming a teenage single mother, passing her GED by a single point, and beginning an unlikely climb.
Janna Levin on the liberating realization that life is not a smooth path interrupted by obstacles—life is the obstacles.
Boyd Varty on using the mindset of a lion tracker to move through uncertainty and the paralysis of not knowing what comes next.

Dr. BJ Miller is a triple amputee, longtime palliative-care physician, cofounder of virtual palliative-care service Mettle Health, and coauthor of A Beginner’s Guide to the End.

Terry Crews is an actor, artist, author, television host, and former NFL player best known as Terry Jeffords on the