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Founder Mode – Episode 19 – The Founder’s Unfair Advantage with Chris Winfield

by Rozelle Picazo

Episode 19: Visibility isn’t a vibe—it’s a system. In this episode, Jason and Kevin sit down with Chris Winfield, creator, connector, and coach, to break down how founders can build an unfair advantage in an AI-saturated world. Chris shares his 80/20 rule for AI usage, why content strategy is non-negotiable in 2025, and how personal connection still beats automation. Learn how to become the go-to expert in your niche, simplify your message like Steve Jobs, and avoid falling into the “Slopbot” trap of over-AI’d content.

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Founder Mode – Episode 28 –  Health Is a Team Sport

Thursday, October 9, 2025

Founder Mode – Episode 28 – Health Is a Team Sport

EPISODE 28: Jason and Kevin dig into why health isn’t a solo sport—and how founders can extend their “work span” by prioritizing community, shared rituals, and better device hygiene. They cover replacing PR-chasing with longevity metrics, carving out weekly “sensorless” time to reset attention, and using an AI “board of directors” to stress-test health decisions...
Founder Mode – Episode 27 – From AI Prototype to Production with Ankur Goyal

Thursday, October 2, 2025

Founder Mode – Episode 27 – From AI Prototype to Production with Ankur Goyal

EPISODE 27: Ankur Goyal joins Founder Mode to show how real teams get from AI prototype to production: build a two-click loop from user complaint to eval, treat observability as a driver of quality, and design iteration environments that connect production logs back to tests. Ankur explains why LLMs behave more like databases than CPUs,...
Founder Mode – Episode 26 – How Not to Run a Startup with Bobby Evans

Thursday, September 25, 2025

Founder Mode – Episode 26 – How Not to Run a Startup with Bobby Evans

EPISODE 26: Bobby Evans goes inversion-first on startup failure modes—from overhiring and bonus wars to vanity metrics, misaligned influencers, and shipping the wrong features. We dig into crypto betting’s realities, why credibility and payouts matter more than hype, the cost of public financialization, and how to protect thinking time, delegate, and avoid perfectionism that delays...
Founder Mode – Episode 23 – From Stonks to AI for Everyone with John Hancock

Thursday, September 4, 2025

Founder Mode – Episode 23 – From Stonks to AI for Everyone with John Hancock

EPISODE 23: In this episode of Founder Mode, John Hancock joins us to break down the gap between startup hype and reality. From building Stonks—the largest angel syndication platform on AngelList—to walking away when the mission no longer fit, John shares what he’s learned about fundraising, pivots, and rebuilding with first principles. He introduces Validate,...

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