The Lifestyle Investor - Investing, Passive Income, Wealth

When your values aren’t clear, it’s easy to chase the wrong deals, hire the wrong people, and build a life and business that drains you.Today, I sit down with Robert Glazer—entrepreneur, bestselling author, and founder of Acceleration Partners—to explore how defining your personal core values can transform the way you lead, invest, and live.Robert built a $35M global company serving brands like Airbnb, Uber, and Adidas, but his greatest success came from understanding what he valued most, and aligning every decision around it.In his new book, The Compass Within, Robert reveals how your personal core values act as a decision-making compass for both business and life. We unpack how to use that same framework to hire the right people, choose the right investors, and build a life of freedom that truly aligns with who you are.In this episode, you’ll learn: 1.) Why really company culture starts with core values — and how defining what you stand for (and what you don’t) helps you attract the right people and repel the wrong ones.2.) What Robert learned from his own private-equity exit—how he structured the deal, picked the right partner, and avoided the mistakes most founders make.3.) How your personal values can help you invest smarter—filtering founders, partners, and deals that align with your principles, not just your profit goals.Show Notes: LifestyleInvestor.com/260Tax 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.

For most entrepreneurs, consuming alcohol is a normalized social ritual. From networking, entertaining clients, and celebrating successes to relaxing with our friends and family. But as you’ll hear from today’s guest, alcohol is really just “attractively packaged poison” for our bodies. Even one or two drinks a night can slowly erode productivity, focus, and decision-making, costing millions of dollars over an entrepreneur's lifetime.James Swanwick knows this firsthand. A former ESPN SportsCenter anchor, James walked away from alcohol in 2010 and saw instant improvements that transformed his life, health, and career trajectory.Today, he’s the founder of Project 90, a neuroscience-based coaching program with a 98% success rate in helping executives, entrepreneurs, and investors reduce or eliminate drinking in just 90 days. He’s also the author of Clear, a practical guide to quitting alcohol without AA, rehab, or willpower.In this episode, you’ll hear the shocking financial and personal costs of drinking—even in moderation—and why going alcohol-free gives high performers and entrepreneurs an ‘unfair’ competitive advantage. James also shares the science behind alcohol’s impact on the brain and body, and how eliminating or significantly reducing alcohol from your life can multiply your clarity, relationships, and wealth.In this episode, you’ll learn: 1.) Why having just one drink a day can quietly destroy your health, relationships, and wealth.2.) The neuroscience-backed framework with a staggering 98% success rate that James uses in Project 90 to help entrepreneurs and executives eliminate alcohol and unlock peak performance.3.) What James calls the “Lost Revenue Calculator” to demonstrate how much an entrepreneur who generates millions in revenue each year could benefit from an alcohol-free lifestyle.Show Notes: LifestyleInvestor.com/259Tax 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.

Too many professionals pursue prestige and big paydays, only to feel trapped in exhausting, unfulfilling careers. Nowhere is that more obvious than in Big Law, where young attorneys trade passion for paychecks—often at the cost of burnout, depression, and a life they never wanted.Bill Reid broke that mold. As a nationally recognized trial lawyer and co-founder of Reid Collins, he’s spent decades taking on corporate giants—banks, accounting firms, and institutions most people thought were untouchable. In his new book, Fighting Bullies: The Case for a Career in Plaintiffs’ Law, he reveals the truth behind Big Law’s broken model and shows why pursuing passion and purpose leads not only to success, but to freedom.What makes Bill’s story resonate far beyond the legal world is the life he’s designed along the way—one of wealth, health, impact, and experiences that his peers envy. His journey is proof that you don’t have to sacrifice your freedom to build real prosperity.In this episode, you’ll learn: 1.) Why Big Law traps so many young attorneys—and how to avoid falling into the same paycheck-driven path.2.) How AI is disrupting industries like law—automating tasks like document review and contracts, and forcing efficiency over billable hours.3.) Bill’s blueprint for an “epic life”—balancing high-stakes work, entrepreneurship, health, and unforgettable experiences with friends and family.Show Notes: LifestyleInvestor.com/258Tax 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.

College tuition is one of the biggest financial burdens families face. Sticker prices are outrageous, financial aid feels confusing, and many parents resign themselves to paying full price—or worse, watching their kids drown in student debt.What if you could legally and strategically cut tens of thousands of dollars off your child’s tuition bill every single year?That’s exactly what Seth Greene helps parents do. Seth is the founder of one of the first and top college financial aid negotiation firms in the U.S., a financial strategist, and co-host of the SharkPreneur podcast. His firm helps families save an average of $37,000–$70,000 per year per child on college education.In this episode, Seth breaks down the “gameable” formula that determines how much the government thinks you can afford, the biggest mistakes families make when applying for aid, and the powerful negotiation strategies that colleges don’t want you to know.By the end, you’ll walk away with actionable insights that could save you six figures per child—freeing up money to invest, grow, and build the lifestyle you really want.In this episode, you’ll learn: 1.) The single most important number in college financial aid—and how to legally “game” it to qualify for more free money.2.) The costly mistakes parents make when applying for aid (like misreporting assets or overvaluing a business)—and how to avoid them.3.) Why private schools can often be cheaper than state schools, and how to use multiple offers as leverage to negotiate more aid.Show Notes: LifestyleInvestor.com/257Tax 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.

Entrepreneurs are often caught in a nonstop race—chasing revenue, scaling businesses, and pushing harder every year. The result? Burnout, strained relationships, and the feeling that freedom is always out of reach.Pete Vargas knows that cycle firsthand. He’s built multiple 7- and 8-figure companies, filled arenas with his “stages” model, and partnered with names like Grant Cardone and Tony Robbins. But the constant hustle left him unhealthy and searching for a better way.In this episode, Pete shares the turning points that shaped his journey—from growing a youth group from 3 to 800 kids, to helping speakers land 25,000+ stages, to creating Wellspring, a mastermind for entrepreneurs who want to win in every area of life. And now, why he’s stepping away for a 90-day sabbatical to reset his faith, health, relationships, wealth, and business.In this episode, you’ll learn: 1.) The life-changing power of one message. Pete shares how a single talk moved his estranged father to seek reconciliation after years of abuse—and how it inspired his mission to help others use stages to impact millions.2.) How to turn crisis into record-breaking success. When COVID canceled his $5M live event, Pete pivoted to virtual and generated over $12M—setting the model leaders like Tony Robbins and Grant Cardone still use today.3.) Why slowing down is your greatest edge. After building multiple 7- and 8-figure companies, Pete is taking a 90-day sabbatical to reset his faith, health, and family—and shows how pressing pause can unlock your best ideas.Show Notes: LifestyleInvestor.com/256Tax 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.

Today, I’m joined by Chris Van Dusen—serial entrepreneur turned Senior Equity Partner at SoCo Capital. Chris built and sold multiple companies, including one of the world’s largest CBD brands, before stepping into the world of private equity and alternative investments.We break down the critical differences between building businesses and investing in them, why luck and timing matter more than people are willing to admit, and how successful family offices and billionaires are acquiring and allocating their wealth.Chris also shares insider lessons on venture capital, private equity, private credit, and even pro sports investing—and how entrepreneurs can apply the same playbook to build generational wealth and financial freedom.In this episode, you’ll learn: 1.) Why most entrepreneurs struggle as investors—and the mindset shift you must make to avoid costly mistakes.2.) The real wealth allocation strategies of billionaires and family offices—and how you can use the same playbook.3.) How to evaluate opportunities across venture, private equity, private credit, and alternative assets to build lasting financial freedom.Show Notes: LifestyleInvestor.com/255Tax 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.

Every entrepreneur dreams of the big exit, yet for many, the American Dream can quickly turn into the American Nightmare.Within five years, Alex Bean went from startup founder to selling Divvy for $2.5 billion to Bill.com—making enough money to never work another day in his life.But instead of fulfillment, he was blindsided by loneliness, loss of identity, strained relationships, and new family challenges money couldn’t fix. He realized what many successful entrepreneurs eventually face: wealth can be a blessing or a curse, depending on how you handle it.Out of this season came Alex’s mission-driven venture, Factory for Good—a company designed to help entrepreneurs and families use money as a force for good, protect their most important relationships, and build lasting wealth that doesn’t destroy the next generation.In this episode, you’ll learn: 1.) Why financial freedom without purpose often leads to loneliness, loss of identity, and broken relationships—and how to avoid it.2.) The Factory for Good framework for turning money, time, and energy into a legacy of impact rather than destruction.3.) Practical strategies Alex uses with his own family—like the “Happiness Audit,” the “Bank of Mom & Dad,” and relationship frameworks—that will change the way you think about wealth, parenting, and purpose.Show Notes: LifestyleInvestor.com/254Tax 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.

Success in business and investing often gets framed as tactics, strategy, or sheer hustle. But according to David Bayer—renowned mindset and performance coach, transformational speaker, and founder of the Powerful Living Experience—the real driver isn’t what you do, it’s the state of mind you operate from.David has guided thousands of entrepreneurs and leaders through his coaching programs, live events, and his book A Changed Mind, helping them rewire limiting beliefs, heal past trauma, and unlock exponential growth. His work blends neuroscience, psychology, spirituality, and business strategy into practical tools that create real transformation.In this episode, he breaks down his framework for Mindset 2.0—a shift from simply recognizing limiting beliefs to actually rewiring them at the neurological level. He explains why your thoughts create the states you live in, how to move from “primal” states of stress into “powerful” states of clarity, and why the quality of your inner game determines the quality of your results. David also reveals his deceptively simple but life-changing formula: Desire + Non-Resistance = Desired Result. Instead of pushing harder or grinding longer, the path to wealth, peace, and fulfillment comes from removing the resistance built into your thinking.If you’ve been stuck in stress, chasing success but feeling misaligned, this conversation will show you how to rewire your beliefs, unlock energy, and create results that flow with far less effort. In this episode, you’ll learn:  1.) How to rewire limiting beliefs with Mindset 2.0 — and why shifting from “primal” states into “powerful” states changes the way you think, feel, and make decisions.2.) The simple formula to achieve anything in life — David’s proven framework for turning desire into results without relying on hustle or grind.3.) Why your reactions reveal your beliefs — and how frustration in business (or life) is never caused by the circumstance itself, but by what you believe underneath it.Show Notes: LifestyleInvestor.com/253Tax 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.

Building and selling a company is hard—but managing wealth afterward is a completely different challenge.Jay Jacobs knows this firsthand. An OG member of The Lifestyle Investor Mastermind, and my very first Private Client, Jay founded RAPID Manufacturing in 2001 and grew it over 17 years into the world’s largest prototype sheet metal manufacturer and the second-largest prototype CNC machining business. RAPID’s success was fueled by leveraging modern technology—and after selling the company for 9-figures, Jay launched Paperless Parts to give other manufacturers access to the same kinds of tools. Today, Paperless Parts is the #1 quoting and estimating software in manufacturing, with $25M ARR.But even with all that success, Jay faced a new reality after his exit: the skills that made him a world-class entrepreneur weren’t the same ones he needed to protect and grow his wealth.As an entrepreneur, he was used to taking calculated risks, moving fast, and having full control over outcomes. As an investor, the rules were different—success meant slowing down, saying “no” more often than “yes,” and trusting others to be good stewards of his capital. The optimism and risk tolerance that served him in business could quickly become liabilities in investing.In this conversation, he shares how he made that transition—building a passive income stream to replace his paycheck, creating guardrails to avoid costly mistakes, and designing a life filled with impact, travel, and passion projects. You’ll hear the mindset changes that guide his decisions, the relationships that open up high-quality deal flow, and the lessons that can help you avoid the costly mistakes that wipe out fortunes.In this episode, you’ll learn: 1.) Why the skills that build a company aren’t the same ones that grow and protect wealth—and how to make the shift from entrepreneur to investor.2.) The strategy behind Jay’s leap from a 9-figure exit to building a $25M ARR industry leader in manufacturing software.3.) The lifestyle design strategies Jay uses to turn passions into profitable ventures and create unforgettable life experiences.Show Notes: LifestyleInvestor.com/252Tax 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.

He was dying. They thought he wouldn’t survive. So they stole his $1B company.Adel Sayegh built a billion-dollar business from nothing—pioneering security tag technology, facial recognition, and GPS tracking. But while he lay on his deathbed battling pancreatic cancer, the people he trusted most betrayed him.They drained his accounts, forged documents, and used his assets to rack up debt. The result? A complete collapse of the empire he spent decades building.In this raw, emotional episode, Adel shares the true story of how he lost everything—and why he wouldn’t trade the experience for anything. From surviving terminal illness to finding unshakable peace through his faith, this is one of the most unbelievable stories ever told on the podcast.In this episode, you’ll learn: 1.) Why Adel chose forgiveness over prosecution—even after being betrayed by his most trusted team members.2.) The hard-earned lessons from bootstrapping a billion-dollar company from his garage—and why he wouldn’t take the same approach today.3.) How faith—and unexplainable miracles—helped Adel survive terminal cancer and discover a greater purpose.Show Notes: LifestyleInvestor.com/251Tax 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.

Ok, this episode is a little different than usual. Instead of interviewing a guest, I got to sit down with two of my closest friends—Jon Vroman and Hal Elrod—for the 500th episode of the Front Row Dads podcast.This wasn’t a business conversation. It was personal. We talked about fatherhood, faith, marriage, brotherhood, and how this community has completely changed the way we show up for our families.I opened up about my health struggles with mold toxicity, how it forced me to slow down, and the surprising gift that came out of it. We also talked about the hard-earned lessons that helped us re-prioritize our marriages, restructure our calendars, and redefine what success really looks like.I’ve been part of Front Row Dads from the very beginning, and it’s no exaggeration to say that it’s the most impactful community I’ve ever been part of. If you’ve ever wrestled with being present at home while building something meaningful in the world—this episode is for you.And if you want to learn even more about fatherhood, marriage, and how to level up your game at home, visit FrontRowDads.com to learn more. In this episode, you’ll learn: 1.) Why saying family comes first isn’t enough—and how to build a life that actually reflects it2.) The hidden habits and vices that hold men back—and why brotherhood is essential for breakthrough3.) How to lead your kids by example and pass on the values that matter mostShow Notes: LifestyleInvestor.com/250Tax 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.

What if you could stop chasing one-time sales and build a business that pays you again and again—predictably, reliably, and without the hustle? That’s exactly what today’s guest, Stu McLaren, has helped thousands of entrepreneurs achieve.As the co-founder of Membership.io and creator of The Membership Experience™, Stu is one of the world’s leading membership experts. He’s spent the last 16+ years helping entrepreneurs turn what they know and love into thriving membership businesses that generate recurring revenue and real freedom. And now he’s packed everything he’s learned into a new book called Predictable Profits.In our conversation, Stu breaks down what actually works when it comes to memberships—what keeps people around, what makes them leave, and how to build something that lasts. No fluff, no hype—just real strategies that actually move the needle.In this episode, you’ll learn: 1.) Why the membership model is the ultimate path to predictable profits—and how it can boost your business valuation, create lifestyle freedom, and unlock compounding revenue over time.2.) The success path framework that will give your members clarity and direction—so they avoid overwhelm, stay engaged longer, and actually get results.3.) How to 3x the lifetime value of your members by optimizing their first 30 days with one simple onboarding strategy.Show Notes: LifestyleInvestor.com/249Tax 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.

What if the very traits you've been taught to hide—like being selfish, nosy, or even manipulative—are actually your greatest unfair advantage?That’s the bold idea Jenny Wood explores in Wild Courage—a framework she developed after nearly two decades at Google, where she rose through the ranks, led billion-dollar business units, and launched initiatives that reached over 50,000 employees across 100+ countries.Eventually, success on paper wasn’t enough. Jenny felt burned out and boxed in—stuck between achievement and alignment. That turning point led her to redefine what real courage looks like in business and life.In this episode, she unpacks the 9 traits society often labels as “too much” or “too aggressive”—and shows how to reclaim them as strategic tools for influence, opportunity, and a life you actually want. Whether you’re looking to land the promotion, launch your business, or stop playing small, this conversation will challenge everything you thought you knew about confidence, leadership, and courage.In this episode, you’ll learn: 1.) The wild subway story that changed Jenny’s life—and the mindset shift that helped her take bold action in the face of fear.2.) Discover the 9 unconventional traits that define Wild Courage—and how they unlock greater influence, freedom, and business growth.3.) Why “manipulative” might be your most powerful leadership trait—and how to use it to build trust, influence, and high-leverage relationships.4.) Why replacing your salary may be the wrong goal—and how to build confidence, earn through passive income, and design a life that truly aligns with what matters most.Show Notes: LifestyleInvestor.com/248Tax 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.

Want to know the biggest reason your marketing isn’t working? It doesn’t reflect you.Most ads are generic. They could work for any business. But the best ads only work for one—because they’re built around the true personality of the founder or brand. They’re specific, not because of the product, but because of who’s behind it. That’s what makes them powerful. That’s what makes them real. That’s the heart of relational marketing— which is what today’s episode is all about.I’m joined by Roy H. Williams—better known as the “Wizard of Ads”—who has helped iconic companies like 1-800-GOT-JUNK craft ads that fueled billion-dollar growth. Over the past 40 years, Roy has advised hundreds of founders, showing them how to grow through story, truth, and personality, instead of gimmicks, hype, or shallow tactics.If you want to write ads that break through the noise and actually connect with your buyers, this episode will change the way you think about marketing forever.In this episode, you’ll learn: 1.) How Roy helped grow 1-800-GOT-JUNK from $97M to $1B—by leading with truth and identity, not data or demographics.2.) Why identity—not logic—drives every buying decision, and how your brand can tap into who your customers really are in order to better serve them.3.) What makes a company truly remarkable—and the one question Roy uses to test if your marketing actually makes people care.4.) The 4 things every human is secretly looking for—and how to build them into your ads so people don’t just notice you… they trust you.Show Notes: LifestyleInvestor.com/247Tax 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.

Today, we’re switching things up. This episode isn’t about money. It’s about meaning. And someone who knows a lot about that subject is Matt Earl Beesley, who turned a childhood love of film into a decades-long directing career—and is now channeling that experience into a passion project with a powerful message, all while building a life and career on his terms.Matt Earl is a Hollywood director whose credits include Braveheart, National Lampoon’s Christmas Vacation, CSI: Miami, Criminal Minds, Bosch, The Closer, and Chicago Fire, just to name a few. He’s worked side-by-side with legends like Clint Eastwood and Steven Spielberg. But beneath the glamorous résumé is a down-to-earth family man who chose passion over prestige and lifestyle over burnout.In this conversation, Matt Earl shares how he broke into one of the most competitive industries in the world, the mindset that carried him from minimum wage intern to top-tier director, and why collaboration—not ego—is the secret weapon of success.He also opens up about his new film project set in Texas—one that blends family, integrity, and the emotional complexity of immigration. If you’ve ever wondered whether you can pursue your craft, make a difference, and still live life on your terms—this episode is your inspiration.In this episode, you’ll learn: 1.) The secret to getting your foot in the door—even when everyone tells you your dream is impossible.2.) The mindset shift Matt Earl learned from Clint Eastwood that transformed his approach to leadership and creativity.3.) Why now might be the best time to invest in indie films—and how Matt Earl’s new movie gives investors a shot at doing good and doing well.Show Notes: LifestyleInvestor.com/246Tax 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.

What if you could cash out of any asset—without paying capital gains tax—and use the full value to create lasting financial freedom?That’s exactly what Brett Swarts helps high-net-worth entrepreneurs and investors do every day—using the Deferred Sales Trust (which is what today’s episode is all about).Brett is the Founder and CEO of Capital Gains Tax Solutions, a firm that’s closed over $500 million in Deferred Sales Trust and commercial real estate transactions. As a DST Trustee and expert in capital gains tax deferral, Brett equips clients and advisors with proven strategies to defer millions in taxes on the sale of highly appreciated assets.While 1031 exchanges and Delaware Statutory Trusts serve a purpose, they often come with rigid rules, long lock-up periods, and limited flexibility. The Deferred Sales Trust, on the other hand, unlocks what most investors really want: tax deferral, liquidity, diversification, and the freedom to reinvest in nearly any asset.Whether you're selling real estate, a business, crypto, or any other asset, this conversation could save you millions in taxes, so you won’t want to miss it. In this episode, you’ll learn: 1.) How the Deferred Sales Trust works—and how it lets you legally defer capital gains, income, and estate taxes.2.) The hidden downsides of 1031 exchanges and Delaware Trusts—and why many investors are moving to a more flexible strategy.3.) How to reset your depreciation schedule after a sale to boost cash flow and reduce future taxes—without the pressure of like-kind rules.Show Notes: LifestyleInvestor.com/245Tax 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.

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.

What if you could tap into the exact investment strategies billionaires use to multiply their wealth—without being one?In this episode, I’m joined by Richard Wilson, founder of the Family Office Club and Billionaires.com. Over the last 18 years, Richard has analyzed over 1,000 billionaire strategies, advised more than 250 family offices, and built the world’s largest network of ultra-wealthy investors.Today, he’s sharing what he’s learned from nearly two decades studying how the ultra-wealthy think, invest, and structure deals. From mental models and niche investing to AI-powered tools and negotiation tactics, you’ll discover the exact strategies billionaires use—and how to apply them to grow your own wealth, no matter where you're starting.In this episode, you’ll learn: 1.) How Richard built the #1 investor club for billionaires—and the exact mental models he’s seen them use to spot better deals and scale with precision.2.) What he’s learned from interviewing hundreds of billionaires and centi-millionaires—including insights from Tony Robbins, Mark Cuban, Kevin Harrington, and many others.3.) How to leverage AI to amplify your investment returns, streamline deal sourcing, and gain a competitive edge.Show Notes: LifestyleInvestor.com/243Tax 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.

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.

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 WorkFrom 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 MarketsLearn 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 MarketIt’s not always about price—see how relationships, timing, and seller psychology can unlock the best opportunities.Show Notes: LifestyleInvestor.com/241Tax 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.