What Founders Get Wrong About Success ft. Harry | Funds and Founders

In this episode of Funds and Founders, we sit down with Harry Morton, the founder of Lower Street and host of Moneywise, to uncover the emotional reality behind wealth, success, and the often-overlooked emptiness that follows an exit. Harry’s company produces podcasts for some of the world’s top brands. But his journey started with waiting tables at Buckingham Palace while bootstrapping his agency from zero. From sound engineering to building a multimillion-dollar podcast business, Harry shares his honest take on: - How to build a real podcast brand in an oversaturated space - What billionaires and millionaires really feel after success - The biggest mistake founders make after an exit - Why 70% of second startups fail — and how to avoid the trap - What founders should know before starting a podcast - The power of differentiation and authenticity in podcasting If you’ve ever wondered how to use podcasting strategically, or what success actually feels like once you’ve achieved it, this episode is a must-watch. 🔗 Connect with Harry Morton Website: https://lowerstreet.co LinkedIn: https://www.linkedin.com/in/harrymorton/ About the host: I’m Abhinav Sinha, host of “Funds & Founders”, a podcast for Austin entrepreneurs navigating early-stage startups. I explore the highs, lows, and breakthrough moments of local founders through candid conversations. I also sit down with VCs to uncover how they evaluate early-stage companies and share practical insights. I create an intimate space for guests to share authentic stories, inspiring aspiring founders along their journey. Contact me here, LinkedIn: https://www.linkedin.com/in/abhinavbsinha/ Newsletter: https://newsletter.fundsandfounder.com/ 0:00 - Trailer 0:40 - Intro 1:47 - The Hidden Truth About High Net-Worth Founders 5:19 - The Dark Side of Entrepreneurship Nobody Talks About 8:02 - Redefining Success: Why a Chill Life Might Be Better Than a Billion-Dollar Company 12:55 - From Idea to First Client: The Real Startup Timeline 15:36 - Moving from Small Clients to Enterprise Deals 16:44 - Building a Face for Enterprise Podcasts 18:12 - Why Big Brands Are Turning Into Media Companies 20:28 - Rethinking Podcast Sponsorships 22:34 - The Harsh Reality of Podcast Growth 26:34 - Getting Real with Guests Without Alienating Them 29:07 - Should SaaS Founders Start a Podcast? 35:17 - Why 80/20 Episodes Perform Better 37:16 - Evergreen vs. Topical Content: What Works Better? 38:23 - What’s Missing in the Podcasting Industry 42:56 - The Future of Podcast Distribution & Authentic Content