Brad Feld — The Art of Unplugging, Carving Your Own Path, and Riding the Entrepreneurial Rollercoaster (#448)

Illustration via 99designs

Brad, they can’t kill you and they can’t eat you. Suit up.

— Len Fassler

Brad Feld (@bfeld) is the author of two new books: The Startup Community Way and the second edition of Startup Communities. He has been an early-stage investor and entrepreneur since 1987. Prior to co-founding Foundry Group, he co-founded Mobius Venture Capital and, prior to that, founded Intensity Ventures. Brad is also a co-founder of Techstars. Brad is a writer and speaker on the topics of venture capital investing and entrepreneurship. He’s written a number of books as part of the Startup Revolution series and writes the blogs Feld Thoughts and Venture Deals.

Brad holds bachelor of science and master of science degrees in management science from the Massachusetts Institute of Technology. Brad is also an art collector and long-distance runner. He has completed 25 marathons as part of his mission to finish a marathon in each of the 50 states.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform. 

Brought to you by Laird Superfood, Theragun, and Thrive Market. More on all three below. 

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

#448: Brad Feld — The Art of Unplugging, Carving Your Own Path, and Riding the Entrepreneurial Rollercoaster

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


Want to hear the episode I did with mutual friend Jerry Colonna (the coach with the spider tattoo)? Listen to our conversation in which we discuss being complicit in creating the conditions in life we don’t really want, nagging self-doubt, finding time for self-discovery, confronting the difficulty most of us have with saying “no,” acknowledging compassion from a distance, journaling, guilt versus remorse, and much more.

#373: Jerry Colonna — The Coach with the Spider Tattoo


  • Connect with Brad Feld:

Feld Thoughts | Brad at Twitter | Startup Community Way at Twitter | LinkedIn


  • Brad shares details of his first off-grid vacation and the genesis of how it came to be. [06:08]
  • In what ways did Brad’s first time off the grid help him, and how does he use shorter increments now to similar effect? Is there a pattern to this practice? [20:05]
  • “They can’t kill you and they can’t eat you.” [26:31]
  • Brad relays his long relationship with depression and anxiety, and explains why he only began speaking publicly about it in 2013. [33:57]
  • How mutual friend (and former guest) Jerry Colonna helped Brad approach and cope with his depressive episodes. [44:50]
  • Revisiting a Jerry Colonna classic: “How are you complicit in creating the conditions you say you don’t want?” [55:35]
  • Brad’s observations of Jerry’s group therapy sessions. [58:59]
  • How did Brad choose his therapist when he got back on the horse and decided to get back in that game? [1:01:57]
  • How does Brad advise someone with an engineering-oriented mind to find a therapist? [1:07:11]
  • The role of a therapist versus that of a coach. [1:08:41]
  • Why does Brad have an obsession with the number three? [1:13:06]
  • Pattern interrupts and life dinners. [1:16:55]
  • As someone who’s managed to sustain a relationship for 30 years, what has Brad learned about communication — particularly when it comes to conflict resolution? [1:21:42]
  • While some couples swear by taking notes as a way to facilitate communication and planning, Brad explains why it doesn’t really work in the relationship he shares with his wife. [1:27:52]
  • How often does brad partake of a digital Sabbath — going without phones or email from Friday night to Sunday morning? [1:32:06]
  • Boredom can be such a glorious luxury. [1:36:15]
  • Favorite books, a rare TV show, and a startup community. [1:37:45]
  • What prompted Brad’s move to Colorado from Boston, and what’s kept him there for 25 years? Are there any downsides to living there? [1:50:40]
  • What is complexity theory, and how does Brad apply it to his own life? [2:04:36]
  • What happens when startup communities create something where nothing previously existed. [2:14:00]
  • Final thoughts and what Brad’s three billboards might say. [2:21:44]


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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9 Replies to “Brad Feld — The Art of Unplugging, Carving Your Own Path, and Riding the Entrepreneurial Rollercoaster (#448)”

  1. I’ve only just this spring started listening to podcasts regularly (Dhru Purohit was my gateway drug). The combo of exploring new info and insights as I do a daily early morning 4-mile walk has been a way to offset these exceedingly stressful and contentious times in which we find ourselves.
    As a person who has volunteered on the frontlines of animal welfare and rescue, frankly I’ve been traumatized by what I’ve seen (the capacity for human neglect and cruelty), still as a rule I do not believe others are responsible for anticipating or avoiding any “triggers” I might have as a result. However I’ll admit that hearing your casual reference to “putting a cat in a pillowcase and smashing it against a tree” felt like a gut punch this morning. While I’ve not (yet) knowingly come across that particular act of sadism, once you voiced it, I realized it was something that likely is done.
    With apologies to Brad Feld, I couldn’t listen to the rest of the podcast and switched to music instead.
    As an influencer and thought leader, I’d ask you, Tim, to be more deliberate about what sort of imagery and energy you choose to generate and perpetuate via your platform.

    1. Tim- I love your podcast and have listened for years. This episode is a very thoughtful and deep conversation but I cannot help but notice how much the new intra-episode ads take away from the moment.

    2. Sabine,

      Jesus, that’s a horrid image. As a fellow animal advocate and cat guardian, I was horrified to read this and I can understand your horror.

      I would agree with you completely and that is why the last time I listened to this podcast I turned it off – since Tim Ferris and Mary Karr began speaking about hunting animals.
      What? Outrageous and grotesque. But then I realized, this isn’t someone who’s claiming enlightenment or spiritual maturity or even kindness – so I’ve had to venture into other pastures, listening to those who embrace a peaceful planet and reverence for animals and the earth herself.

  2. My wife and I listened to this show together, and we loved it. Tim, you have grown so much as an interviewer, and it shines in this episode. Well done!

  3. A plethora of wonderful resources in the show notes, I particularly enjoyed being directed to Topophilia.

  4. Your podcast has been such a great resource for direct steps and inspiration. Last year I was cleaning boats in MN and listening to your podcast and now I live in Breck and have started my own outdoor kettlebell/yoga flow class that I love so much and am in the process of starting a keto protein bar company with a friend I met teaching cross country skiing! I also wanted to share with you guys my friend’s Wim Hof breathing method [Moderator: promotional content removed.]. I appreciate you guys filling up my head with inspiring and useful conversations that make me feel like I’ve had free access to the best mentors around- you’re the best. ♥

  5. There are a lot of book rec’s (especially in the sci-fi genre) made in this podcast. From those, and the fact that Rothfuss has been mentioned in the past, I think anyone that enjoys those worlds should give the Red Rising series by Pierce Brown a look. I can’t recommend his books highly enough.