Can entrepreneurship actually be taught — or do you just have to go get punched in the mouth?

It's an old jab: those who can't do, teach. David Hasler is the awkward counterexample. He spent fifteen years in finance leadership, running the org for Walmart's $125B U.S. grocery business (and later Health & Wellness), led a treasury project that saved store operations over $1B — and then chose to go teach founders how to raise fifty grand. 🎓

He's now Kentucky's 2022 Startup Coach of the Year, 2023 Startup Mentor of the Year, a lecturer in entrepreneurship, and the guy who built the Startup Ecosystem Roadmap that maps the founder's journey from "is there a there-there?" all the way to IPO.

In this conversation, David makes the case that education doesn't replace the arena — it reduces uncertainty before you walk into it. 🗺️

What we get into:

🔥 Whether entrepreneurship education is ever just snake oil — and how to spot real content vs. feel-good platitudes
📈 What actually transfers from Fortune 1 finance to a pre-seed startup, and what he had to unlearn
🧭 The Startup Ecosystem Map and the Three Key Questions that keep new founders from drowning in information overload
🤝 "Finding your Jeff" — why the visionary needs the integrator, and what Henry Ford owed James Couzens
💸 Why founders are chronically financially illiterate, and how a simple model beats a beautiful pitch deck
🌎 Kentucky vs. the coasts vs. Denmark — how regional risk profiles and collaboration models change what's possible
🏗️ Building culture on purpose in the early days, before it builds itself
🤖 How AI is compressing the entrepreneurship classroom — and why case studies should be dissected, not admired
🏘️ Collaboration over competition, and how regions stop exporting their own "economic refugees"

Whether you're building something, teaching someone who is, or trying to grow the ecosystem around you — this one's for you. ⚡

Connect with David: https://www.linkedin.com/in/dhasler/

Reach out for a copy of the Startup Ecosystem Map: coffeechaoscashflow@gmail.com

Coffee, Chaos, & Cashflow. Season 5.