241: How the Wealthy Invest Differently: Private Markets, AI Disruption, and Negotiating Better Terms with Brad Weimert & Garrett Gunderson

What happens when you sit down with two brilliant friends to talk money, markets, and mindset? You get a raw, unfiltered conversation that challenges conventional thinking and rewires how you approach wealth and opportunity.

In this episode, I’m joined by Garrett Gunderson and Brad Weimert for a wide-ranging roundtable on building wealth in today’s fast-changing world.

We dive into big topics—from AI’s disruption of legal, banking, and finance, to why the smartest money is moving further away from Wall Street, to how top investors are getting early access to emerging tech and private deals. 

We also talk real estate, sharing personal stories on how to win deals—not just by offering more money, but by understanding seller psychology and waiting for the right moment.

In this episode, you’ll learn: 

1.) How AI is Reshaping the Future of Education and Work

From publishing and teaching to legal and finance, discover where AI is replacing humans—and where it’s not.

2.) Why the Smartest Investors Are Going All-In on Private Markets

Learn how the ultra-wealthy vet early-stage companies and why public markets are no longer the best path to wealth.

3.) The Secret to Winning Real Estate Deals in Any Market

It’s not always about price—see how relationships, timing, and seller psychology can unlock the best opportunities.

Show Notes: LifestyleInvestor.com/241

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