What Investors Actually Look For in Founders - Andrew Nash on Reputation, Risk & Building Again | Ep. 5

What separates founders who scale from the ones who stall? Andrew Nash has spent 40 years finding out. Serial founder, investor, and entrepreneur Andrew J. Nash has built and exited companies acquired by Apple, eBay, Deloitte, and Chowly. After selling Targetable in 2024, he moved back to Australia ready to step back - and then AI pulled him right back into the arena. Now he's building again: launching Austral Impact to strengthen the Australian startup ecosystem, developing Kemu (a vendor-agnostic AI orchestration platform), teaching as an Enterprise Professor at the University of Melbourne, and hosting his own podcast, Big Bets and Bad Calls. In this conversation, Justin and Andrew get honest about what a 40-year career of exits actually comes down to — and it's not the technology. It's the trust. What we cover: Why Andrew left retirement to build again — and what he saw in AI that others missed What Kemu is and why vendor-agnostic AI orchestration matters How Austral Impact is filling a critical gap in the Australian startup ecosystem What Andrew looks for in a founding team before writing a check Whether personal brand and reputation actually influence investment decisions The case for founder-led brands in B2B Big bets he's proud of — and bad calls he'll put on the record If you're a founder, investor, or operator building something that's meant to last — this one's for you. Episode Chapters: 00:00 — Introduction & How Justin and Andrew Met 01:00 — Andrew's 60-Second Career Pitch (The Forrest Gump Version) 03:00 — Why AI Pulled Him Out of Retirement 05:15 — Learn, Earn, Return: The Framework Behind Everything Andrew Does 08:00 — Austral Impact: Closing the Gap in the Australian Startup Ecosystem 09:30 — Why He Started Big Bets and Bad Calls (And What the Name Really Means) 20:30 — Kemu Deep Dive: Building the AI Orchestration Platform of the Future 34:00 — We're Only 1-2% Into the AI Revolution 40:30 — Is Reputation the Real Throughline Behind Andrew's Exits? 43:00 — Jockey Over Horse: How Andrew Evaluates Founders Before Investing 47:00 — Founder-Led Brand: Vanity Play or Business Necessity? 49:00 — The #1 Role of a Founder and What to Look for in a Team 52:00 — The Biggest Bet of His Life (Moving to the US in the 90s) 53:00 — Risk, Resilience, and Running Hard at It Connect with Andrew Nash: 🔗 LinkedIn: linkedin.com/in/andrewjnash 🎙️ Big Bets and Bad Calls: [URL] 🌐 Austral Impact: [URL] 🤖 Kemu: [URL] Return on Reputation is hosted by Justin Obey, founder of OBEY Creative. New episodes every week at the intersection of reputation, visibility, and business growth. 🔗 LinkedIn: [URL] 🌐 OBEY Creative: [URL] 📩 The Authority Brief: [URL] #PersonalBrand #FounderStory #Entrepreneurship #ReturnOnReputation #AndrewNash #AIStartups #FounderLedBrand #B2BMarketing #StartupPodcast #Reputation