#156 Rich Thomson: From Banker to Founder of Dreamliner Luxury Coaches and Caprice Capital

Rich Thomson is the Founder and CEO of Dreamliner Luxury Coaches and Caprice Capital Partners. He spent 20 years in banking and lending at GE Capital, Citibank, and Brightwood Capital before making a pivotal decision: to stop financing other people's companies and start building his own.In this episode, Rich shares what it actually takes to run two very different businesses at the same time, a luxury transportation company serving music tours, NFL, NBA, PGA, and NASCAR, and an alternative lending firm that has deployed over $700 million into founder-owned companies. He talks about why founders often misunderstand what private equity is really selling, and what a better capital partnership looks like.We also get into the human side of Rich's journey: the hardest lessons from year one of Dreamliner, how he hires people he can trust to run things without him, and why someone with his background still feels the pull to build rather than just invest.If you are a professional who has spent years working for others and is wondering whether to bet on yourself, this conversation is for you.About Rich Thomson🚌 Founder and CEO of Dreamliner Luxury Coaches and Caprice Capital Partners- 💼 https://www.linkedin.com/in/richthomson- 🌐 https://dreamlinercoaches.com- 🌐 https://capricecapital.comAbout Federico Ramallo ✨👨‍💻🌎🚀 Software Engineering Manager | 🛠 Founder of DensityLabs.io & PreVetted.ai | 🤝 Connecting 🇺🇸 U.S. teams with top nearshore 🌎 LATAM engineers- 💼 https://www.linkedin.com/in/framallo/- 🌐 https://densitylabs.io- ✅ https://prevetted.ai🎙 PreVetted Podcast 🎧📡- 🎯 https://prevetted.ai/podcast- 🐦 https://x.com/PrevettedPod- 🔗 https://www.linkedin.com/company/prevetted-podcast00:00 Introduction to Rich Thompson and Dreamliner Luxury Coaches03:01 The Logistics of Live Event Transportation06:02 Transitioning from Banking to Entrepreneurship08:54 Lessons from 20 Years in Lending11:55 What Sets Dreamliner Apart from Rental Services15:02 The Importance of Professional Drivers18:09 The Unique Experience of Bus Travel20:55 The Art of Custom Bus Building24:03 Caprice Capital: Supporting Founders Differently28:17 Innovative Financing Solutions for Entrepreneurs30:52 The Importance of Alignment in Business32:54 Evaluating Founders: The People Factor35:57 Building a Supportive Company Culture39:13 Learning from Mistakes and Bad Hires40:24 The Balance of Optimism and Realism in Business45:33 Navigating Outside Capital: Terms vs. Relationships50:28 Advice for Aspiring Founders: Go All In