TOMS Founder Blake Mycoskie — Fear{less} with Tim Ferriss (#551)

“Fear really was a motivator and has been in many different chapters in TOMS. Not because I was afraid of failing as a business, but failing other humans is a much heavier burden to wear.”

— Blake Mycoskie

Welcome to another episode of The Tim Ferriss Show, where it is my job to deconstruct world-class performers to tease out the routines, habits, et cetera that you can apply to your own life.

You’ll get plenty of that in this special episode, which features my interview with Blake Mycoskie from my 2017 TV Show Fear{less}. The “less” is in parentheses because the objective is to teach you to fear less, not to be fearless.

Fear{less} features in-depth, long-form conversations with top performers, focusing on how they’ve overcome fears and made hard decisions, embracing discomfort and thinking big.

It was produced by Wild West Productions, and I worked with them to make both the video and audio available to you for free, my dear listeners. You can find the video of this episode on, and eventually you’ll be able to see all episodes for free at

Spearheaded by actor/producer and past podcast guest Vince Vaughn, Wild West Productions has produced a string of hit movies including The Internship, Couples Retreat, Four Christmases, and The Break-Up.

In 2020, Wild West produced the comedy The Opening Act, starring Jimmy O. Yang and Cedric The Entertainer. In addition to Fear{less}, their television credits include Undeniable with Joe Buck, ESPN’s 30 for 30 episode about the ’85 Bears, and the Netflix animated show F is for Family.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Amazon Musicor on your favorite podcast platform. You can watch the interview on YouTube here.

The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#551: TOMS Founder Blake Mycoskie — Fear{less} with Tim Ferriss

This episode is brought to you by 5-Bullet Friday, my very own email newsletter that every Friday features five bullet points highlighting cool things I’ve found that week, including apps, books, documentaries, gadgets, albums, articles, TV shows, new hacks or tricks, and—of course—all sorts of weird stuff I’ve dug up from around the world.

It’s free, it’s always going to be free, and you can subscribe now at

What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear another episode with Blake Mycoskie? Listen to our 2020 conversation in which we discussed the Hoffman Process, Blake’s experiences with plant medicine, conscious uncoupling, Madefor—his new business that helps people learn and sustain positive habits and practices that have the greatest impact on their lives, and much more.

#446: Blake Mycoskie — TOMS, The Hoffman Process, Conscious Uncoupling, and Psychedelics
  • Connect with Blake Mycoskie:

Website | Twitter | Facebook | Instagram


  • What is Butter Busters, and how did it help inspire Blake’s entrepreneurial vision at an early age? [07:52]
  • What backup career was Blake’s time at SMU preparing him for if his professional tennis aspirations didn’t work out? [11:05]
  • Blake’s favorite philosophers and their works. [13:12]
  • Blake details his journaling habit and how it started. [14:10]
  • The origin story of Blake’s first business on the SMU campus, and the sneaky ruse he borrowed from Ben Franklin to drum up customers. [16:43]
  • It turns out running a full-time business while trying to go to school full-time is hard. So what happened next? [21:05]
  • How did reality TV change Blake’s life and teach him a valuable, but costly lesson about business? [22:05]
  • What did Blake do to cope with the depression he experienced after this first big business failure, and how did this roll him into his next venture? [26:00]
  • The TOMS origin story: how it came about when Blake was trying to take a vacation from business. [29:00]
  • How did TOMS get its first burst of real publicity, and in what way did this quickly turn into a good news/bad news situation? [35:48]
  • Shoebags vs. shoeboxes from a retail standpoint. [42:49]
  • What is Blake’s greatest fear in business? What does failure look like to him? [47:08]
  • Books Blake can’t live without. [49:45]
  • If Blake lost everything today, what would he be most thankful for? [53:14]
  • Why the calendar is king in the Mycoskie household. [54:06]
  • What Blake’s billboard would say and parting thoughts. [57:35]


“Fear really was a motivator and has been in many different chapters in TOMS. Not because I was afraid of failing as a business, but failing other humans is a much heavier burden to wear.”
— Blake Mycoskie

“The calendar is king.”
— Blake Mycoskie

“Carpe diem. That is the mantra that has served me so well. … If I do that, then I’m giving the most I can to what I’ve been given.
— Blake Mycoskie

“A fortune can be made out of literally your kitchen and a typewriter.”
— Blake Mycoskie

“If there’s one thing that can help get your life on a more positive path, journaling is it.”
— Blake Mycoskie

“I think Indiana Jones is the best job.”
— Blake Mycoskie


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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One Reply to “TOMS Founder Blake Mycoskie — Fear{less} with Tim Ferriss (#551)”

  1. Hi, I’m a new listener to your podcasts, just subscribed to your newsletter and VERY impressed by the breadth of topics you cover. Would you be interested in having a guest interview with Gautam Jain (teacher of Vedanta philosophy, based in NJ) who shows how to apply ancient Indian spiritual wisdom in modern life, particularly to improve productivity? He is an awesome speaker who has addressed elite organizations and institutions around the world, such as Goldman Sachs, YPO-WPO (the world’s largest CEO group), IBM, AT&T, Columbia, Princeton, and MIT. He has also been featured on ABC and PBS.