Matthew Stafford: The 5 Influential People Who Shaped Entrepreneur & Investor Matthew’s Life | People Are Everything

S03-E03 People Are Everything with Matthew Stafford

Entrepreneur, investor, and Nine Others co-founder Matthew Stafford joins Julia Duthie on People Are Everything to share the 5 most influential people who shaped his life and career.

From Margaret Thatcher’s enterprising Britain, to Richard Branson’s fearless entrepreneurship, a teacher who took a chance, the investor Chris Sacca’s philosophy of being “default helpful”, and value investor Guy Spier’s wisdom on goodwill and handwritten letters — Matthew reflects on the mindsets and people that defined each decade of his journey.

Along the way, he recalls early connections with startups like Citymapper, Uber, and What3Words, why building networks is about generosity, and how life events reshaped his perspective on money, patience, and impact.

Episode Highlights

Margaret Thatcher (1980s) – Inspired Matthew’s early view of enterprise and business, watching his farming family experience the shift from high taxes to entrepreneurial opportunity.

Richard Branson (1990s) – A poster child for risk-taking and adventure; Matthew modelled early hustles (videotaping The Simpsons, selling t-shirts) on Branson’s fearless approach.

Brendan Hodgson (2000s) – Durham University teacher who took a chance on Matthew despite poor A-levels, reigniting his love of maths and teaching him the creativity of problem-solving.

Chris Sacca (2010s) – Investor who inspired Matthew’s “default helpful” philosophy; the idea that generosity and connection build long-term success in startups and investment.

Guy Spier (2020s) – Value investor and author of The Education of a Value Investor, who reinforced Matthew’s practice of handwritten thank-you letters and the idea of goodwill compounding.

Nine Others community – Founded in 2011, small curated dinners where founders share challenges; has grown into a worldwide movement.

Startups connected to Nine Others –

• Citymapper: Asmat’s focus on user experience over Google Maps.
• Uber: Matthew met early team in London, saw the “magical” product before global domination.
• What3Words: Worked with founder Chris Sheldrick in early days, now life-saving tech. – Matthew opens up about his son’s serious illness and how it reshaped his perspective on life, long-term thinking, and the importance of impact.
• Both Julia and Matthew bond over the lost art of thank-you notes as a legacy more lasting than digital communication.

👉 Matthew’s book Find Your Nine Others (Amazon) captures stories and lessons from a decade of dinners that helped founders worldwide connect, collaborate, and grow.

Matthew Nine Others - https://9others.com/

Matthew LinedIn - https://www.linkedin.com/in/staffordvc/

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