The Amanda Dake Podcast
What does it look like when someone successful finally admits they're living at a 6? James Friel had the career — the titles, the bonuses, the offer to run global marketing from London. And he said no. James Friel is the founder of J Street Financial and a serial entrepreneur who has built everything from digital consultancies to ghost kitchens to financial advisory firms. But before all of that, he was a high-performing corporate executive who looked like he had it all — and felt the quiet pull to do something more. In this conversation, James unpacks the entrepreneurial mindset behind some of the biggest career pivots of his life: why he turned down a CMO track, what his grandfather's question — "What if your ladder's leaning against the wrong wall?" — actually cost him to answer, and how he learned to make decisions with confidence rather than regret. This is a how it started, how it's going conversation — and James gets specific about both. In this episode: ➡️ The first sale James ever made (he was 8 years old) ➡️ Why high-achievers stay stuck at a 6 — comfortable, but not fulfilled ➡️ Turning down London, a promotion, and a CMO runway ➡️ What personal development really looks like for serious founders ➡️ The difference between a bookkeeper and a true financial co-pilot ➡️ Warren Buffett, Annie Duke, and the cost of second-guessing your decisions ➡️ How J Street Financial helps entrepreneurs move from rearview-mirror thinking to windshield clarity Connect with James Friel: 🌐 Free Financial Health Check: https://www.jstreetfinancial.com ☑️ https://www.linkedin.com/in/jamespfriel 📧 james@jstreetfinancial.com Timestamps: 00:00 — Introduction: James Friel, Serial Entrepreneur & Founder of J Street Financial 03:00 — His Grandfather's Question: "What If Your Ladder's Leaning Against the Wrong Wall?" 07:27 — The Defining Moment: Turning Down London & the CMO Track 11:15 — What Happens When You Bet on Yourself (and Everyone Thinks You're Crazy) 16:19 — Living on the Edge: Why Comfort Is the Enemy of Growth 23:50 — Connecting the Dots: Lessons from Roses, Ghost Kitchens & Every Venture In Between 29:00 — J Street Financial: From Rearview Mirror to Windshield Want to know your number? Take the 2-minute assessment at https://amanda-pyaik3fu.scoreapp.com
25 episodios
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