Brad Feld is a renowned venture capitalist, entrepreneur, and author, best known as co-founder of Techstars and the Foundry Group. He has been at the center of startup investing for decades, shaping conversations around mentorship, Startup Communities, and the 'give before you get' philosophy.

Brad has written nine books, including Venture Deals, Startup Communities, Startup Boards, and his most recent work Give First, which explores the power of mentorship and long-term relationships in the startup world. The conversation covers his key mentors, from Uncle Charlie Feld to his personal 'Yoda' Len Fassler, and how these relationships shaped his approach to business and life.

The discussion explores how The Hitchhiker's Guide to the Galaxy influenced his entrepreneurial philosophy, the evolution from his 2012 book Startup Communities to his latest work, and how Adam Grant's Give and Take provided academic validation for his mentorship philosophy. Brad also shares insights about his recent 'hibernation' from public life and his return to promote Give First.

Heroes and Early Influences Shape Entrepreneurial Philosophy

Brad's heroes include Zaphod Beeblebrox from The Hitchhiker's Guide to the Galaxy, whose philosophy 'the best way to fly is to throw yourself at the ground and miss' became central to Brad's approach to creating companies.

Albert Einstein, Warren Buffett, and Charlie Munger represent his admiration for independent thinkers who 'just did their own thing their way' and held true to their values consistently over time.

Contemporary heroes include Paula Johnson (Wellesley College), Lucy Sanders (National Center for Women in IT), and Wendy Lee, all focused on supporting entrepreneurship and public service.

Uncle Charlie Opens the Door to Technology and Business

At age 12, Uncle Charlie Feld (head of data processing at Frito-Lay) introduced Brad to computers by handing him A Programming Language (APL) - 'a black book with red covers' - in the company's underground data center.

Charlie regularly brought teenage Brad to high-level meetings with Digital Equipment Corp and Lotus, letting him 'sit at the table' rather than 'sit in the corner and be quiet.'

The mentorship evolved into peer relationship when Brad's business became larger than Charlie's Feld Group, demonstrating 'the magic trick of mentorship' where mentor and mentee become peers.

Len Fassler: The Master Class in Authentic Leadership

Len Fassler acquired Brad's company Feld Technologies after a lunch meeting, saying 'I learned enough in the first 30 minutes about you to know that I want you to be part of my company' - Brad.

Len's investment philosophy became Brad's template: 'Be willing to take risks on people, but make your judgment quickly' based on interest in the product and wanting to partner with the person.

Len exemplified fighting 'to the bitter end' regardless of circumstances, teaching Brad to separate commitment from control and to 'just get up and do the work' no matter how difficult.

The relationship was characterized by 'lovely' authenticity - Len was 'comfortable in his own skin' and 'didn't try to be somebody else,' inspiring others to walk their own path.

From 'Give Before You Get' to Academic Validation

Startup Communities (2012) introduced the phrase 'startup community' and included one paragraph on 'give before you get' as an afterthought that became foundational to Brad's philosophy.

Adam Grant's Give and Take provided academic research six months later, showing 'the most successful people are givers' and 'the least successful people are givers,' with different characteristics separating them.

The philosophy evolved from 'give before you get' to Give First when Greg Cochran at Techstars started using #givefirst on Twitter due to character limitations.

Give First took years to complete, with Brad hibernating from public life for two years before returning specifically to promote the book about mentorship and long-term relationships.

The Interconnected World of Reading, Writing, and Creating

Brad processes ideas through reading and writing rather than talking or listening, which he describes as 'idea reinforcement' that solidifies existing thoughts.

Writing books helps Brad 'understand better an idea and work out the idea' rather than for money, platform, or ego - though Venture Deals has been 'hugely successful.'

Books create 'a different layer of connection' between people, with Brad actively seeking relationships with other authors and book lovers through his platform.

Brad logs all reading on Goodreads with a personal system: '5 stars if I finished a book, 4 stars if I started skimming, 3 stars if I didn't finish' because he thinks traditional star systems are useless.