The Lifestyle Investor - Investing, Passive Income, Wealth

Jenny Wood, author of 'Wild Courage' and a former Google executive, shares her journey from corporate success to personal fulfillment. She challenges the notion that negative traits like selfishness and manipulation are weaknesses, framing them instead as tools for influence and growth. Jenny reveals nine unconventional traits that embody Wild Courage and discusses the importance of mindset shifts in overcoming fear. Her insights offer a fresh perspective on leadership, showing how embracing audacity can unlock opportunities and lead to a more fulfilling life.

Roy H. Williams, the "Wizard of Ads," has spent 40 years helping brands like 1-800-GOT-JUNK achieve billion-dollar growth through authentic storytelling. He reveals that the key to powerful advertisements is reflecting the true identity of the founder or brand. Discussing emotional marketing, he emphasizes that identity—not logic—drives buying decisions. Williams shares how to embed authenticity in your marketing and identifies four fundamental human desires that should be incorporated into your ads for true connection.

Matt Earl Beesley is a Hollywood director known for his work on classics like Braveheart and Christmas Vacation. In this conversation, he shares his inspiring journey from an intern to a successful director, emphasizing the power of collaboration over ego. He also dives into his passion project in Texas, which explores themes of immigration and family dynamics. Beesley reflects on meaningful storytelling and the mindset shifts learned from industry legends, offering sage advice for pursuing one's craft while maintaining a fulfilling life.

Brett Swarts, Founder and CEO of Capital Gains Tax Solutions, shares his expertise in deferring taxes on appreciated assets. He reveals how the Deferred Sales Trust can enable investors to cash out without incurring capital gains taxes, unlocking financial freedom. The discussion highlights the limitations of 1031 exchanges and advocates for a flexible, strategic approach to tax mitigation. Brett empowers listeners with actionable insights to enhance wealth via effective tax strategies and investment planning.

You set out to build wealth, then realized your family was getting the leftovers.But it doesn’t have to be either-or, you can thrive in both.Today, I’m talking with Chad Willardson—wealth advisor to 8 & 9-figure founders, serial entrepreneur, bestselling author, and father of five—who’s figured out how to scale his wealth and stay fully present for his family. He runs a successful wealth advisory firm, owns multiple businesses, travels by private jet, and still makes it to his kids’ games.In this conversation, Chad reveals the exact frameworks he uses to buy back time, build lasting wealth, and prioritize what matters most—insights he expands on in his upcoming book, Fully Invested: Why Work-Life Balance Is a Total Lie.You’ll learn how he structures investments, leverages debt without stress, and designs a calendar around his life, not just his work.In this episode, you’ll learn: 1.) The habits and systems Chad uses to prioritize family without sacrificing growth2.) The “buy, borrow, die” strategy that Chad uses to grow his wealth tax-free3.) The real cost (and benefit) of buying a private jet4.) The “Right Brain / Left Brain” executive assistant system that saved his time and sanityShow Notes: LifestyleInvestor.com/244Tax Strategy MasterclassIf 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/taxStrategy 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Richard Wilson, founder of Family Office Club and Billionaires.com, shares insights gained from analyzing over 1,000 billionaire strategies. He reveals the mental models used by the ultra-wealthy to spot lucrative deals and emphasizes the importance of niche investing. The conversation explores leveraging AI for better investment returns and the role of family values in creating a lasting legacy. Wilson also highlights the power of community engagement and mastermind groups to enhance financial growth and accountability.

Most people are chasing a retirement plan they’ll never enjoy – or even want. Derek Coburn is here to show you a more meaningful path that doesn’t require you to escape your life to start enjoying it.Derek is a best-selling author, founder of the Cadre mastermind, and a former financial advisor to ultra-wealthy clients. After 20+ years in the industry, he sold his firm, walked away from the grind, and redefined what true financial freedom looks like. In this episode, Derek breaks down why the traditional model of retirement is outdated, inefficient, and in some cases, dangerously misleading. We explore smarter tax strategies the wealthy use to future-proof their income, the rising wave of “unretirement,” and why fulfillment doesn’t come from chasing a number… but from showing up with purpose. He also shares the story behind his newly released book, Let’s Retire Retirement, and reveals the $50,000 mindset shift that transformed how he shows up as a father, a leader, and a man of faith. In this episode, you’ll learn:  1.) Why 1 in 3 retirees return to work – and how to design a life you never want to retire from instead. 2.) The hidden risks of 401(k)s – plus the tax strategies wealthy investors are using to protect their future income. 3.) The time machine exercise that redefined Derek’s relationship with time, money, and fatherhood – and how you can create special moments in your own life.Show Notes: LifestyleInvestor.com/242Tax Strategy MasterclassIf 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/taxStrategy 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this engaging discussion, Brad Weimert, an entrepreneur specializing in wealth building, and Garrett Gunderson, a wealth strategist challenging traditional finance, dive into the evolving landscape of investing. They explore AI's impact on industries, highlighting where it replaces jobs and where it doesn't. The duo explains why ultra-wealthy investors are increasingly attracted to private markets over public ones. They share clever strategies for winning real estate deals by understanding seller psychology, proving that timing and relationships often outweigh mere price.

I used to believe the key to success was working harder than everyone else.And for a while, that served me. But over time, I started asking different questions—like what would it look like to build a life where work didn’t come at the expense of family, faith, or freedom?This episode is a little different, as I’m the one being interviewed. Preston Brown, host of the Problems to Profit Podcast, pulls out the biggest lessons I’ve learned, from selling newspaper subscriptions in middle school to investing in private deals that create passive income and real-time freedom today.We get into why I prioritize passive income over net worth, and how relationships and masterminds have opened the door to some of my biggest opportunities.In this episode, you’ll learn: 1.) How one passive income deal replaced my wife’s income—and how that one move kickstarted our journey to financial freedom.2.) My personal framework for allocating surplus income into deals that create long-term freedom.3.) Why I created The Lifestyle Investor Mastermind—an exclusive community giving members access to the same deals and strategies used by the ultra-wealthy.Show Notes: LifestyleInvestor.com/240Tax Strategy MasterclassIf 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/taxStrategy 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/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf 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 DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Anastasia Koroleva, a four-time exiting entrepreneur and host of The Exit Paradox, shares her journey following a lucrative business sale. She candidly discusses the identity crisis and costly investment mistakes that can follow financial success. Anastasia emphasizes why financial freedom doesn’t guarantee happiness and the importance of cultivating intentional relationships. She also highlights the value of teaching children about financial independence and the need for community support during life transitions. A must-listen for aspiring founders!