Brad Feld On The Emotional Operating System of Great Leaders and Giving First
Brad Feld, co-founder of Techstars and Foundry Group, joins Michael to unpack the philosophy behind his book Give First—but this isn’t a standard VC retrospective. It’s a raw, thoughtful conversation about the operational and emotional systems behind generosity, mentorship, identity, and meaning. Brad shares stories from the early Boulder startup days, what most people misunderstand about giving, how to mentor without directing, and why trust is the foundation of everything that matters. Along the way, he reflects on what writing books has taught him, how he approaches emotional intelligence, and what happens when the second floor of your building literally collapses during peak holiday season.
Get Brad's new book, Give First.
00:00 — Cold open: “Something new is fucked up in my world every day”
02:00 — The Yoda t-shirt story + the mythology of Brad Feld
04:00 — “Give First” vs. “Pay it Forward”: philosophy, not obligation
07:00 — Why giving isn’t altruism — and how it works in complex systems
10:00 — Positive-sum vs. zero-sum: tennis, trust, and long games
13:00 — Does giving create outcomes, or just energy?
16:00 — Why Brad writes books: longform thinking as meaning-making
20:00 — Searching for meaning through mentorship and reflection
23:00 — “I hate the phrase pattern recognition” — mentorship done right
28:00 — The power dynamic between founders and mentors
32:00 — Management through commitment, not control
35:00 — Agile as an operating system for accountability
38:00 — Emotional intelligence and the role of executive coaches
41:00 — Mentor vs. coach vs. therapist vs. advisor
45:00 — Trust as the foundation of all high-leverage relationships
47:30 — Wild story: when the second floor of Sphero’s building collapsed
52:00 — “They can’t kill you and they can’t eat you” – Len Fassler’s advice
55:00 — Closing thoughts on being the Bill Murray of venture capital
