What if generosity—not hustle—is your greatest competitive advantage?

Brad Feld—co-founder of Foundry Group, Mobius Venture Capital, and startup accelerator Techstars—joins Barry to explore the transformative philosophy of “Give First,” a mindset that’s reshaped how founders, investors, and mentors build lasting companies and vibrant startup ecosystems. Brad has spent over three decades cultivating startup communities by putting people before profit and helping others without expecting anything in return.

In this episode, he shares the mindset shifts that fueled Techstars’ global influence, how mentorship evolves from hierarchy to peer learning, and why sustainable success stems from playing the long game. A conversation full of clarity, candor, and challenge—for anyone rethinking what it means to lead, contribute, and create.

Key Takeaways

• Generosity Fuels Growth: Giving without expectation of return builds stronger relationships, ecosystems, and companies.
• Mentorship is a Two-Way Street: The most impactful mentoring happens when both sides learn, grow, and give.
• Play the Long Game: Positive-sum, multi-turn thinking creates more meaningful and lasting impact than transactional wins.
• Know Yourself First: Deep self-awareness—not external success metrics—is the foundation of better leadership.

Additional Insights

• Redefine Success on Your Own Terms: Society pushes for more—money, power, status—but real fulfillment comes from understanding what truly matters to you.
• Build a Network of Givers: Shared values transcend geography. A global community built on generosity leads to collective resilience.
• Let Go of the Need for Control: Great mentors—and leaders—create space for co-creation, not dictation.
• Disconnect to Reconnect: Time away from constant input helps surface your clearest thinking and truest desires.

Episode Highlights:

00:00 – Episode Recap

Brad Feld reframes mentorship as a shift from a one-way hierarchy to a peer-based relationship.

01:48 – Barry Introduces Brad Feld

Barry introduces Brad's influential work on startup communities and his philosophy of "Give First."

03:12 – Startup Community Origins

Brad shares how the idea of startup communities became a global movement—challenging the belief that tech startups must be in Silicon Valley.

12:54 – The Give First Philosophy

Brad explains why generosity, long-term thinking, and non-transactional relationships are foundational to resilient startup ecosystems.

21:33 – Mentorship as Mutual Growth

A powerful story with mentor Len Fast reveals how Brad came to see mentorship as co-learning rather than knowledge transfer.

27:27 – Knowing Yourself

Brad emphasizes how self-awareness and personal growth are essential to leadership, especially in a world driven by reactive norms.

34:48 – Creating Space for What Matters

A candid discussion on disconnecting from external pressures, valuing inner reflection, and how time off helped Brad refocus on his values.

41:47 – Redesigning Relationships

Brad shares how he and his wife created structure and rules to prioritize their relationship—offering insight into the intersection of discipline and intimacy.

45:41 – Final Reflections

Brad closes with a message on leading through generosity, not transactions—and why playing the long game builds stronger companies and communities.

Episode Resources

Brad Feld on LinkedIn: Brad Feld

Foundry Group on LinkedIn: Foundry Group

Foundry Group website: foundrygroup.com

Techstars website: techstars.com