Rob Finlay is a Wall Street Journal bestselling author, serial entrepreneur, and commercial real estate investor who has built and sold four companies and started over 15 ventures. As a father of four, sought-after speaker, and mentor, Rob is known for his forward-thinking solutions, strategic insights, and dedication to education. His latest book, Hey Dad: Everything You Should Have Learned But Didn’t, hit the WSJ bestseller list in its first week. Rob’s journey is a masterclass in resilience, reinvention, and building businesses that solve real problems.

On this episode we talk about:

– Rob’s first entrepreneurial leap—mortgaging everything at 29 to start his first company while supporting a young family

– The emotional rollercoaster of entrepreneurship, from failures to the surprising challenges of a successful exit

– Why “passive income” is often a myth and the real work required to build and sustain a business

– The difference between true entrepreneurs and “wantrepreneurs”—and why sweat equity beats throwing money at problems

– How Rob built multiple businesses by focusing on a single niche (commercial real estate) and evolving solutions for the same customer base

– The power of prioritization, constraint, and solving your own problems as a founder

– Trends and opportunities in commercial real estate, especially in the current high-interest rate environment

– The two levers for making money in real estate: optimizing the asset and mastering the debt

– Why Rob wrote Hey Dad, the lessons he wants to pass on to his kids, and the surprising overlap between business and parenting

– The realities of traditional publishing, book marketing, and why writing a book is more about impact than income

Top 3 Takeaways

1. Solve Real Problems in a Niche: Sustainable success comes from deeply understanding your customer and evolving your solutions as their needs change—not chasing every new trend.

2. Sweat Equity Beats Easy Money: Throwing money at problems rarely works; the real magic happens when you’re forced to get creative and build systems from the ground up.

3. Legacy is More Than Money: The lessons you pass on—about resilience, networking, and being a good human—matter as much as financial success.

Notable Quotes

– “Your business is what defines you. When you sell it, you have to redefine yourself—and that’s a whole new challenge.”

– “Passive income is a pipe dream for most people. The real work is in building the business, not just throwing money at it.”

– “If you’re not going to do a good job—if you don’t really care—find something else. Don’t just write a book to write a book.”

Connect with Rob Finlay:

– Website: robfinlay.com

– Instagram: https://www.instagram.com/robjfinlay/

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