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November 6, 2025 50 mins

Far too many investors seek out advice and chase ROI without realizing how much bias and hidden costs are influencing their decisions. Pay-to-play is very common in the mastermind space, but there is one community that has a different set of rules.

I’ve been a member of many mastermind groups over the years, and that’s why I want to highlight what sets the Lifestyle Investor communities apart from the rest. What started as a handful of friends talking shop and sharing deals over a glass of wine has become one of the fastest-growing investment communities in the world.

Today, I’m joined by Ryan Casey, Chief Operating Officer of The Lifestyle Investor, to pull back the curtain on how our communities have evolved into a global ecosystem with world-class due diligence, exclusive deal flow, and unforgettable live event experiences around the world.

You’ll hear how we’ve redefined the way people build wealth. From eliminating bias in investing and spending upwards of $300k/year on vetting and due diligence, to creating programs like our Foundations group for young adults, the Open Community for new investors, and even a financial literacy book for kids.

Whether you’re just starting your wealth journey or scaling into financial freedom, this episode shows how to build a life designed around freedom, purpose, and the people you love.


In this episode, you’ll learn: 


1.) How we’ve built an investment ecosystem that is the opposite of a “pay-to-play” group and helps our members avoid costly mistakes with industry leading experts and strategies.


2.) The difference between our four communities—Lifestyle Investor, Tribe of Investors, Foundations, and the Open Community—and how to know which one’s right for you.


3.) How we’re empowering families to build wealth across generations through mentorship, education, and actionable investment frameworks.


Show Notes: LifestyleInvestor.com/263


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


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