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.com

About 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-podcast

00:00 Introduction to Rich Thompson and Dreamliner Luxury Coaches

03:01 The Logistics of Live Event Transportation

06:02 Transitioning from Banking to Entrepreneurship

08:54 Lessons from 20 Years in Lending

11:55 What Sets Dreamliner Apart from Rental Services

15:02 The Importance of Professional Drivers

18:09 The Unique Experience of Bus Travel

20:55 The Art of Custom Bus Building

24:03 Caprice Capital: Supporting Founders Differently

28:17 Innovative Financing Solutions for Entrepreneurs

30:52 The Importance of Alignment in Business

32:54 Evaluating Founders: The People Factor

35:57 Building a Supportive Company Culture

39:13 Learning from Mistakes and Bad Hires

40:24 The Balance of Optimism and Realism in Business

45:33 Navigating Outside Capital: Terms vs. Relationships

50:28 Advice for Aspiring Founders: Go All In