Building lasting wealth isn’t just about making money—it’s about designing a system that creates freedom, flexibility, and long-term security. And today’s guest is a real estate entrepreneur who has mastered the art of turning land deals into a powerful cash-generating engine that fuels both lifestyle and legacy.

Jack Bosch is a seasoned real estate investor who has flipped over 4,000 land deals and helped hundreds of entrepreneurs build scalable, location-independent businesses. Alongside his wife Michelle, Jack has built land flipping into a high-leverage “cash machine” that funds long-term investments, passive income, and true lifestyle freedom.

If you’re looking for a practical framework to move beyond the earn-and-spend cycle and build income that supports life on your terms, this conversation delivers.

In this episode, you’ll learn:

✅ Why land flipping can be a simpler and more flexible entry point into real estate than traditional investments

✅ Jack’s method for finding deeply discounted land deals that can often be flipped in a very short period of time.

✅ How Jack’s Forever Cash framework turns active income into lasting passive income and wealth.

Show Notes: LifestyleInvestor.com/273

Tax Strategy Masterclass

If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax

Strategy Session

For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation

The Lifestyle Investor Insider

Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider

Rate & Review

If you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.

Connect with Justin Donald

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Jared Friedman, Partner, Y Combinator; Co-founder, Scribd

The Social Radars

Why Jared Left Scribd in 2015

The AI-powered Podcast Player