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Simplicity Wins: Inside the Mind of a Professional Investor w/ Matthew Stafford
Matthew Stafford, professional investor and co-founder of Nine Others, argues that simplicity wins. He shares how starting on the Venture Capitalist side sharpened his founder's empathy, the early signals he listens for, and how one dinner became a global peer network. We unpack the pre-boom London fundraising scene, practical ways to cut noise from your pitch, and the community mechanics that actually move founders forward.
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Episode Resources
- Nine Others - Official Website (co-founded by Matthew Stafford) (https://9others.com/)
- “What’s Keeping You Up at Night?” by Matthew Stafford & Katie Lewis (https://a.co/d/hMhyJBI)
- Overview of Matt & STAFFORD VC (https://www.stafford.vc/?pvs=143)
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When Core Values Beat Venture Capital: Building a Bootstrapped Business w/ Jesse Mecham of YNAB
Jesse Mecham, former accountant and creator of You Need A Budget, argues that your real money problem is worry, not math. He shares how a tiny spreadsheet he built to fix one household cash crunch became a calm, profitable business, and what he learned from building his software and methodology: YNAB (You Need A Budget) at night while working full time, botched early hires, and the moment he stopped playing small. We unpack the myths around raising money, co founders, and five year plans, how to grow slowly on purpose without feeling behind, and practical ways to feel in control of your money again. Along the way, Jesse shows how changing your relationship with money can reshape how you think about risk, work, and the life you are building.
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Episode Resources
You Need A Budget (YNAB) - Jesse’s budgeting software and methodology that he created. (https://www.ynab.com)
True Alignment: Linking Company Culture with Customer Needs for Extraordinary Results, by Edgar Papke. (https://www.truealignment.com/true-alignment/)
“Antifragile: Things That Gain from Disorder” by Nassim Nicholas Taleb. This book speaks about how systems and people can benefit from volatility and stress.(https://a.co/d/hWw7TJW)
“Titan: The Life of John D. Rockefeller, Sr.” by Ron Chernow. (https://a.co/d/gUs7qXn)
“Washington: A Life” by Ron Chernow. (https://a.co/d/bzkS3F0)
“Goals! ” by Brian Tracy. This book is a classic goal-setting and personal development book. (https://a.co/d/9wnWUi4)
“Rich Dad Poor Dad” by Robert Kiyosaki. A Personal finance book. (https://a.co/d/aSFlfOq)
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Leveraging Accelerators to Build & Scale Your Startup w/ Tom Griffiths of Gale Payments
In today’s episode I talk with Tom Griffiths, co-founder of Gale Payments, as we uncover the realities of startup life and accelerators. Tom shares his journey through multiple ventures, including lessons learned from building without customers, balancing speed with craft, and why accelerators like Techstars were crucial for his company’s growth. He dives deep into the power of networks, the importance of traction when applying, and how founders can overcome common pitfalls. Whether you’re considering an accelerator or just curious about the startup process, this episode is packed full of valuable insights anyone can learn from. --- Episode Resources Check out what Tom and his co-founder are building at Gale Payments (https://www.withgale.com) The Underdog Founder by Adrezio de la Cruz (https://a.co/d/gD2GnaI) The Founder University "Pre-Accelerator" Course by Jason Calacanis (https://www.founder.university)
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