Brad Feld has spent over 40 years building companies, mentoring founders, and investing in the startup ecosystem. He’s the co-founder of Techstars, a prolific venture capitalist, and the author of nine books.

In this episode, Brad opens up about the mental reset that came with turning 60, why he stopped chasing “more,” and what led him to dust off a book draft about mentorship that had been sitting on the shelf. We go deep into his new book Give First, his belief in non-transactional generosity, and why he thinks founders should lead from curiosity, not ego.

Brad also shares what went wrong at Techstars, what it taught him about founder empathy, and how he thinks about legacy in a world where everything is temporary.

Where to find Brad:

Timestamps:
(00:00) Why Brad chose to go into hibernation
(03:36) How stepping back gave him a 9-to-5 for the first time
(06:58) Returning to code and reading 3 books a week
(08:05) The four things Brad actually loves
(10:11) Not striving, not optimizing: a new mindset for a new decade
(13:14) The messy journey of writing Give First
(15:08) Feedback that reshaped the book
(17:34) Techstars’ awkward teenage years
(19:59) Coming out of hibernation, temporarily
(23:32) Alter egos: Brad the Book Salesman, Vlad, and Spike
(29:14) The pain of watching Techstars struggle publicly
(34:30) How founder empathy deepened after Techstars’ turbulence
(36:28) What Give First really means and what it does not
(38:49) Positive-sum, multi-turn thinking
(41:34) Why tennis is the perfect metaphor for long-term success
(45:00) Give First as the startup community engine
(48:21) Mentorship without expectations
(50:07) Socratic questioning and the five whys
(54:00) Diagnosing startup fundraising problems
(56:32) Being open to randomness
(58:57) The power of short assignments and low-stakes access
(01:04:28) Why Brad keeps writing: to learn
(01:07:14) What he wishes he knew earlier
(01:10:34) Advice for founders stepping into leadership
(01:12:38) Mortality, meaning, and option value

In this episode, you’ll learn:

How Give First evolved from a Techstars mantra into a movement
The difference between mentorship and advice
Why and how being a giver pays off
How to set boundaries while still being responsive
What makes founder relationships thrive or break
Why being open to randomness can change everything
How to navigate difficult company phases with empathy
What Brad believes really matters in the third act of life

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