
S1E187 - Matthew Stafford: What's Keeping You Up at Night? Building Wealth Through Give-First Relationships: How To Grow a Global Network by Being Helpful Without Expectation
Published: December 29, 2025
Duration: 1:01:21
Matthew Stafford is a venture capitalist, angel investor, and co-founder of Nine Others—a global entrepreneur network spanning 5,000 founders across 50 cities—who transformed from school dropout to successful investor by proving that authentic, give-first relationships create more wealth than transactional networking.
3:00 - Matthew explains the Nine Others concept: monthly dinners for 10 people where founders share their biggest challenge by answering "What's keeping you up at night?" The community has run for 14 years and inspired his new book of the same title.
7:20 - School dropout story: Matthew shares the uncomfortable reality of dropping out after weeks at c...