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.