Despite outward success, Brad Feld struggled with depression, exhaustion, and feelings of emptiness. For years, he hid these challenges while relentlessly pushing forward as an entrepreneur. It wasn’t until his 40s, after seeking therapy and confronting his mental health, that Brad realized success wasn’t just about building companies, but about managing the emotional toll of entrepreneurship. 

Today, as the co-founder of Techstars and Foundry Group, he leads with a harmonious approach to work and life. In this episode, Brad joins Ilana to share the lessons he learned from early failures, why every successful founder faces ‘near-death moments’, and the mental health practices that helped him find joy again.

Brad Feld is a venture capitalist, entrepreneur, and co-founder of Techstars, one of the world’s leading startup accelerators. He is also the co-founder of two venture capital firms, Foundry Group and Mobius Venture Capital.

In this episode, Ilana and Brad discuss:

(00:00) Introduction

(01:07) Growing Up in Dallas and Discovering Computers

(07:29) MIT Years and Early Startup Failures

(14:17) Why Every Startup Faces a Near-Death Experience

(16:54) Battling Fear, Shame, and Depression in His Twenties

(26:52) Breaking Down at 47 Despite “Having It All”

(29:05) Brad’s Practical Steps for Rediscovering Joy

(41:54) The Random Day Experiment and Birth of Techstars

(52:47) Writing Venture Deals, Startup Communities, and Give First

(59:26) Coming Out of “Hibernation” to Write His Last Non-Fiction

(1:13:39) Work-Life Balance vs. Work-Life Harmony

Brad Feld is a venture capitalist, entrepreneur, and co-founder of Techstars, one of the world’s leading startup accelerators. He is also the co-founder of two venture capital firms, Foundry Group and Mobius Venture Capital. Brad is the author of nine books, including Venture Deals, Startup Communities, and Give First. Through his books, investments, and philosophy of “give first,” Brad has become a mentor to thousands of entrepreneurs navigating the brutal highs and lows of building a business.

Connect with Brad: 

Brad’s Website: feld.com Brad’s LinkedIn: linkedin.com/in/bfeld 

Resources Mentioned

Brad’s Book, Give First: The Power of Mentorship: https://www.amazon.com/dp/1646871324  Brad’s Book, Startup Communities: Building an Entrepreneurial Ecosystem in Your City: https://www.amazon.com/dp/1118441540  Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist by Brad Feld and Jason Mendelson: https://www.amazon.com/dp/1118443616  Reboot: Leadership and the Art of Growing Up by Jerry Colonna: https://www.amazon.com/dp/0062749536