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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
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
- YouTube
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
View all episodes
By Justin Donald
4.9
282282 ratings
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
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
- YouTube
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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