Brad Feld isn’t just a name in venture capital; he’s one of the architects behind the startup ecosystem as we know it. From launching Techstars to mentoring hundreds of founders and fund managers, his legacy is rooted in building, not boasting.

Here’s a glimpse of what you’ll learn:

00:48 Introduction to Driving Alpha
01:38 Brad Feld's Journey and Achievements
03:38 Reflections on Life and Career
05:51 The Future of Foundry Group
08:02 Mentorship and Its Impact
10:52 Influential Mentors in Brad's Life
15:17 The SoftBank Connection
23:29 Star Wars vs. Star Trek
27:58 Analog Analog and Investment Insights
30:31 The Evolution of Ticketing Platforms
30:51 AI in Customer Support
31:31 Personal Coding Journey
32:14 Comparing AI Models: Claude vs. OpenAI
35:09 Investment Dynamics in Tech
36:17 The Economics of Ride-Sharing
38:17 The Future of AI-Powered Tools
41:30 Challenges in Venture Capital
54:22 Reflections on Venture Capital

In this episode,

Brad joins Steve Brotman of Alpha Partners for a wide-ranging conversation on investing through downturns, the rise of AI-powered tooling, and what it truly means to give first. Brad explains how his thinking evolved across three decades, from early wins to long-tail fund management, and how he's now channeling his energy into mentorship, writing, and second-order impact.

He opens up about his “third third” philosophy of life, lessons from working with SoftBank in the dot-com era, and why today’s founders can’t afford to chase hype. Brad also shares his hands-on experience using tools like Cursor and Claude, drawing unexpected parallels between AI and the early internet. This is more than a look back; it’s a roadmap for what’s ahead.

Want more of Brad’s wisdom? Grab his latest book: Give First: The Power of Mentorship, a must-read for founders, fund managers, and anyone shaping the future of innovation.

From Techstars to AI trends: Brad Feld of Foundry VC on building enduring legacies