Callum Woodcock spent seven years dreaming about starting a company while working at JP Morgan.
He had zero investor connections, was searching for a perfect co-founder who didn’t exist, and kept reading entrepreneurship books instead of actually getting started.
In this episode of Founders With Nick, Callum reveals how he went from corporate paralysis to building a wine investment platform that’s solving problems the entire industry has ignored for decades, why most wine businesses accidentally become Ponzi schemes, and how his deepest insecurities became the driving force behind his success.
00:00 Introduction
02:00 Building in Barcelona and what this interview aims to uncover
06:24 Bootstrapping versus venture capital and the emotional cost
08:24 Breaking in without a network and the snowball effect of one contact
12:52 Just ask for help and ditch the self-reliance myth
18:12 How Cotri’s backing changed everything for credibility
24:19 The legal structure that lets clients keep their tax perks
25:33 Who WineFi is not for and why that matters
29:04 Deep ownership, identity and how workaholism shows up
35:49 Self-doubt, overthinking and who keeps him grounded
46:55 A real misstep with a post and what he learned from it
51:33 Finding community and levelling up through founder networks
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LinkedIn: https://www.linkedin.com/in/callumwoodcock/
Instagram: https://www.instagram.com/winefi_official/?hl=en
WineFi: https://winefi.co/
