Episodes

  • 254: Why a $2.5B Exit Didn’t Lead to Happiness with Alex Bean

    254: Why a $2.5B Exit Didn’t Lead to Happiness with Alex Bean
    Sep 4 2025
    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.
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    51 mins
  • 253: Rewire Your Mind: The Simple Formula for Wealth & Freedom with David Bayer

    253: Rewire Your Mind: The Simple Formula for Wealth & Freedom with David Bayer
    Aug 28 2025
    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.
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    46 mins
  • 252: How to Protect and Grow Wealth After Selling Your Business with Jay Jacobs

    252: How to Protect and Grow Wealth After Selling Your Business with Jay Jacobs
    Aug 21 2025
    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.
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    53 mins
  • 251: They Stole His $1B Company While He Was on His Deathbed with Adel Sayegh

    251: They Stole His $1B Company While He Was on His Deathbed with Adel Sayegh
    Aug 14 2025
    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.
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    41 mins
  • 250: Redefining Success as a Husband & Father with Jon Vroman and Hal Elrod

    250: Redefining Success as a Husband & Father with Jon Vroman and Hal Elrod
    Aug 7 2025
    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.
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    1 hr and 29 mins
  • 249: The Proven Membership Strategy for Predictable Profits with Stu McLaren

    249: The Proven Membership Strategy for Predictable Profits with Stu McLaren
    Jul 31 2025
    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.
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    42 mins
  • 248: How to Lead With Wild Courage (Even If You’re Afraid) with Jenny Wood

    248: How to Lead With Wild Courage (Even If You’re Afraid) with Jenny Wood
    Jul 24 2025
    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.
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    55 mins
  • 247: The Ad Copywriter Behind Billion Dollar Brands with Roy H. Williams

    247: The Ad Copywriter Behind Billion Dollar Brands with Roy H. Williams
    Jul 17 2025
    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.
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    1 hr and 7 mins