#88 Matthew Stafford - From School Dropout to Venture Capital

In this episode, Simon Cockram sits down with Matthew Stafford to explore the power of networks, the journey into venture capital, and what really makes founders and businesses succeed. Matthew shares how, despite leaving school with poor grades, he hustled through early jobs, discovered tech during the Y2K boom, and eventually transformed his career with a computer science degree at Durham University—proving it’s never too late to reinvent yourself. His path through consulting, an MBA, and into early-stage investing reveals valuable lessons about grit, persistence, and taking chances.

We dive into the creation of Nine Others, Matthew’s global network of curated dinners that have brought entrepreneurs together in over 50 cities since 2011. He explains why a “give-first” mindset, safe spaces, and accountability are key to meaningful connections, and why playing the long game in relationships beats short-term transactions.

From pitching basics to the reality of venture capital, Matthew breaks down what separates successful founders from those who fail, including the idea of “with or without you” energy. He also shares insights from his investments, including Unplugged’s digital detox cabins, and reflects on why the best opportunities often look obscure before they become obvious.

Chapters 00:00 – Why networking matters (from a reluctant networker)

04:00 – Business school lesson: “your network is your net worth” (reframed)

08:00 – Nine Others origin: small, curated dinners since 2011

12:00 – Give-first mindset: be helpful, connect, share generously

16:00 – Play the long game: relationships over transactions

20:00 – Designing safer rooms: rules, vulnerability, real challenges

24:00 – From investor dinners to founder circles: the aha moment

28:00 – Scaling to 50+ cities: community before “startup hubs”

32:00 – Common founder problems: money, people, communication

36:00 – Funding options and targeting the right investors

40:00 – Great pitch basics: keep it short, simple, get the meeting

44:00 – Relationship-first investing: truth, timelines, and trust

48:00 – School results, early jobs & first hustles

52:00 – John Lewis to Y2K: landing RBS IT role

56:00 – Learning tech on the job; consulting at Bank of New York

01:00:00 – Back to uni at 27: Durham CS degree, transformation

01:04:00 – Post-degree restlessness; MBA and discovering venture capital

01:08:00 – First early-stage investor role; portfolio math and exits

01:12:00 – Picking winners: grit, “with/without you” energy, Tesla lens; Unplugged case; wrap-up & contact info