Leap Academy with Ilana Golan
Episode 126: Techstars Co-Founder, Brad Feld: How to Find Meaning While Achieving Success
Release Date: September 23, 2025

Episode Overview

In this poignant and insightful episode, Ilana Golan sits down with Brad Feld—trailblazer in the startup world, co-founder of Techstars, Foundry Group, Mobius Venture Capital, author, and mentor. They candidly explore the untold emotional truths behind entrepreneurial success, Brad’s journey with mental health, the philosophy of "Give First," the perils and powers of mentorship, and finding meaning beyond achievements. Listeners are equipped with concrete lessons and stories on how to leap careers, create impact, and most importantly, cultivate a life of meaning and harmony.

Key Discussion Points & Insights

1. Early Entrepreneurial Roots and First Failures

• Brad’s Introduction to Technology:
  Brad’s fascination with computers began at age 12 (1977), nurtured by a supportive environment and his uncle Charlie Feld, an influential CIO.

  • “My introduction to computers were through Charlie. The very first time I sat in front of a computer was in a data center in downtown Dallas that Frito Lay had, in front of a green screen terminal connected to some mainframe computer.” (03:11)

• Entrepreneurial Spark in Texas & MIT:
  Early exposure to real business through a husband-and-wife software company (Petcom), earning both hourly wages and royalties.

  • “I got checks in the mail…one month I got a little bit over $10,000, which was a mind-blowing amount of money for a freshman in college in 1983/84.” (08:35)

• First Startups and Failures:

  • Martingale Software: aimed to make early Mac software similar to Excel, but Microsoft beat them to market.
  • Another company: built cephalographic analysis software—discovered the pain of building for a market that didn’t exist.
  • On failure: “The emotional experience of going through this thing and then having to be done with it, that was powerful.” (13:45)
  • “Every company I’ve ever been involved in had a near death experience.” (16:02)

2. The Process of Building & Failing in Startups

• Experiments and Hypotheses:
  • “The way a business is, it’s just a hypothesis. You run an experiment…most of the experiments fail.” (17:26)
  • “Even in the things that didn’t work…the struggles were a real challenge for me…as I’ve gotten older, I understand that it’s just part of the experience.” (18:41)

3. Mental Health, Depression, and Emotional Struggles

• Deep Dive into Anxiety and Depression:
  Brad discusses openly his lifelong anxiety, periods of severe depression, and the intersections of personal struggles with professional life.

  • “For me, depression is total and complete absence of joy. It’s not that I can’t function, but there’s just no joy in anything.” (24:39)
  • “I was very functional…I would just lay on the couch and stare at the ceiling. For me, depression is total and complete absence of joy.” (24:56)
  • “You can be very functional as a business person… and you can be really miserable.” (26:27)

• The Power of Community, Mentorship, and Therapy:

  • Brad’s journey through therapy, understanding his own anxiety/OCD, and his eventual openness about it, inspired by others (Jerry Colonna, Dave Morin, Paul English).
  • “One of the things at that point…you can be very functional as a business person, as a founder, as a CEO, as a leader, and you can be really miserable.” (26:27)
  • On sharing: “If I don’t talk about this, I’m actually hurting myself…let it out.” (37:54)

4. Achievement vs. Meaning

• The False Summit of External Success:

  • “I don’t need any more money. I don’t need any more success. My business was successful. I got very, very depressed.” (00:35)
  • “The worst situation is not necessarily a bad career…It’s many times the good career that isn’t yours.” (28:35)

• The Journey to Self-Understanding:

  • “I had to work through understanding what actually mattered to me in the context of all the things that up to the age of 47, I had been doing, but that I had never really understood why they mattered.” (28:43)
  • Brad’s “Digital Sabbath,” stopping drinking, getting proper rest – practical measures along his journey toward meaning.
  • “I just didn’t want to feel this way, so I wanted to get to the root cause.” (29:59)

5. Mentorship, Give First Philosophy, and Building Techstars

• Origins of “Give First” and Random Day:

  • “My goal was two things. One, learn one thing for me and two, figure out one way to help the person so that every meeting I was in, the person would have one thing to be leaving the meeting to be helpful with.” (44:21)
  • Birth of Techstars came out of these “Random Day” meetings (44:09–47:24).

• The Power of Mentorship:

  • “The most influential mentors on me behaved that way where they weren’t being directive…supportive, but it was in the presence of the problem…I was facing and giving data to help me think through and come up with my own solution.” (41:59)
  • “Not telling people the answer, but of giving them stories from your own experience that they could either decide to do something with or to totally ignore.” (38:57)

• Expanding the Model:

  • Techstars' expansion and openness to sharing the model (“Give First” in action):
    “We didn’t have an ask of those other people. We didn’t say, ‘we’ll tell you how to do it if you give us this’…relations were already developed.” (50:44)

6. Writing That Gives Back

• Book Motivation:
  • “Venture Deals”: to demystify and decode opaque term sheets for founders.
  • “Startup Communities”: to democratize startup ecosystems, empower founders outside Silicon Valley.
  • “Give First”: synthesizes decades of lived values, pulling together lessons from mentors and personal experience.
  • “I wanted to somehow pull that together in a book that wasn’t a memoir…if this can be impactful on some people, that’s rewarding of itself.” (67:44)

7. Finding Harmony, Not Balance

• On “Work-Life Balance”:
  • “Amy and I decided a long time ago to delete the word balance from our vocabulary…balance means things are actually in balance. That is never the way life works…” (75:54)
  • “We’re gonna go for harmony…when it’s not harmonious, it’s a signal to me to sort of step back and pay attention.” (76:38)
  • “Search for harmony, not for balance…really listen and understand what’s not in harmony.” (78:34)

8. Aging, Regret, and Active Living

• On Regret:

  • “I don’t regret anything that I failed at. I don’t regret any failures…my only real regrets are situations where I was passive avoidant.” (71:20)
  • “The interesting thing about active avoidance versus passive avoidance is…I’m gonna choose where I’m gonna put my energy on the things that I actually think I can have impact on…” (74:37)

• Letting Go of Relevance:

  • “Are people still going to care about me?…there’s a great peacefulness in saying I don’t care…getting to that place was really hard.” (75:13)

Notable Quotes & Memorable Moments

• On Failure:

  • “Every company I’ve ever been involved in had a near death experience. A bunch of them died. And all the successful ones had at least one near death experience. Really, like that moment where you’re like, this thing is over.” (16:02)

• On Depression:

  • “For me, depression is total and complete absence of joy…It’s not that I can’t function, but there’s just no joy in anything.” (24:56)
  • “Whatever the negative emotion is…is so extreme that you almost can’t stand it. The cliche of the entrepreneur at 3 o'clock in the morning…is the nice version of that. We kind of make heroes out of that behavior, yet it’s actually really not. It’s terrifying.” (34:50)

• On Mentorship:

  • “The most influential mentors on me…weren’t being directive…supportive in the presence of the problem I was facing and giving data to help me think through and come up with my own solution.” (41:59)

• On Give First Philosophy:

  • “If you do it and you do it well and you do it in a way that’s accessible to others and you don’t try to control where it goes, the things that come around are wild and wonderful.” (60:37)

• On Harmony:

  • “We’re gonna go for harmony. And harmony is such a useful, wonderful word. I don’t need balance in my day…I just want most of the time it to be harmonious.” (76:38)

Timestamps for Key Segments

• Brad’s Childhood, MIT, and First Ventures – (02:27–13:37)
• How Failure Shaped Entrepreneurial Mindset – (13:45–18:41)
• Mental Health, Therapy, and Shame – (19:09–29:59)
• Finding Meaning Beyond Achievement – (28:35–34:13)
• Embracing Vulnerability and Sharing Depression – (34:50–41:59)
• The Give First Mentality & Techstars Creation – (44:09–54:19)
• Writing with Purpose and the Impact of Books – (55:01–61:34)
• Regret, Avoidance, and Aging – (70:29–75:13)
• Work-Life Harmony vs. Balance – (75:54–78:34)

Closing Advice

• For Listeners Leaping Careers or Seeking Meaning:
  • Search for harmony, not balance.
  • Be intentional—avoid passive avoidance.
  • Share your struggles; mentorship is about stories, not prescriptions.
  • Focus on impact that’s meaningful for you, not on external validation.

Reach Brad:

• Email: brad@feld.com (“Just give me context—for example, that you heard me on Ilana’s podcast.”)

Read & Share:

• Brad’s books are available on Amazon and other online booksellers; “If you like the book, tell your friends, leave a review…If you don’t like it, just throw it away.” (80:00)

This summary captures the heartfelt journey and hard-earned wisdom Brad Feld shares—an essential listen for entrepreneurs, leaders, and anyone looking to redefine success and live a more meaningful life.