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. 

#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]