Navigating Entrepreneurship: Art Galleries and Real Estate Challenges

This chapter explores the compelling journey of a former prosecutor who ventured into the art world as an entrepreneur, managing multiple galleries. It highlights the challenges faced during the 2008 financial crisis and the unique interplay between art and real estate investments.

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Why does this veteran real estate investor say that early retirement and financial freedom are a bad idea? Why does he think renting, NOT buying a house, makes more sense for most Americans in 2025? And what’s the one mistake that lost him hundreds of thousands of dollars even after being an experienced investor for decades? Jonathan Greene, one of our favorite repeat guests, is back on the show to share.

Jonathan’s father, a serial real estate investor, taught him everything about rental properties early on. Together, they walked potential properties, snuck into foreclosed homes, reviewed the profits and figures line by line, and even dealt with evictions together. This equipped Jonathan with the skills to not only build generational wealth for his family but also financial freedom for himself. However, once he achieved it, Jonathan realized that early financial freedom wasn’t worth it. But why?

This episode looks into the mind of one of the most experienced investors in the entire industry. Jonathan shares why he still decided to work even after building a real estate portfolio, the investment he made that cost him severely, why he’s moving his money into a more “passive” investment, the reason renting makes MORE sense than buying in 2025, and what a beginner should do RIGHT NOW to start investing in real estate.

In This Episode We Cover:

The reason Jonathan says early retirement/financial freedom is a mistake

One thing every beginner to real estate investing should be doing right now

Jonathan’s huge loss and the lessons he learned about pricing yourself too high

Renting vs. buying and the obvious choice for most Americans in 2025

What to teach your kids about real estate investing and generational wealth

And So Much More!

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Buy, Rehab, Rent, Refinance, Repeat