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The Lifestyle Investor - Investing, Passive Income, Wealth

The Lifestyle Investor - Investing, Passive Income, Wealth

325 episodes — Page 1 of 7

314: How to Avoid Losing Money in Multifamily Real Estate with Andrew Cushman

Nov 12, 202639 min

Lens #017 - If you don't understand THIS you don't understand investing

Nov 9, 20265 min

313: How Finding the Right People Builds a World-Class Community with Phoebe Mroczek

Nov 5, 202646 min

Lens #016 - What NOBODY tells you about Trump accounts (skip the $1,000)

Nov 2, 20266 min

312: The 5 Wealth Traps That Could Be Costing You Millions with Justin Donald & Dane Espegard

Oct 29, 20261h 20m

Lens #015 - Why the IPO is over (and where the money actually went)

Oct 26, 20264 min

Lens #014 - Why your savings are losing 10% a year (not 3 anymore)

Oct 20, 20265 min

311: The Hidden Cost of Poor Company Culture with Cathy Christen

Oct 20, 202638 min

310: From Living in a Van to $1.4M in Net Worth with Michael Alberse

Oct 5, 202639 min

309: The First Step to Making Your Business More Valuable and Sellable with Eric Rozenberg

Sep 24, 202633 min

308: What Two 9-Figure Exits Taught a Serial Entrepreneur About Investing with Ben Rubenstein

Sep 17, 202655 min

307: Why Asking for Help Is a Superpower for Success with Nathan Thomas

Sep 10, 202644 min

306: How Wealthy Families Use Whole Life Insurance as a Family Bank with Brock Fortner

Sep 3, 202641 min

305: The 3 Health Metrics Everyone Should Be Tracking To Improve Longevity with Dr. Ryan Williamson, M.D.

Aug 27, 202641 min

Lens #013 - Never Trust a Skinny Chef With Your Money

Aug 23, 20263 min

304: How to Escape From Living Paycheck-to-Paycheck and Build Lasting Wealth with Anthony O'Neal

Aug 20, 202643 min

Lens #012 - 40 Entrepreneurs, 1 Skill Everyone Was Missing

Aug 16, 20267 min

303: The Venture Capital Strategy That The Wealthiest Investors Use with Yotis Tonnelier

Aug 13, 202659 min

Lens #011 - 1,000 Lunches Built My Entire Investing Career

Aug 9, 20266 min

302: Why Creativity Is the Ultimate Wealth-Building Skill with Nick Nanton

Aug 6, 202640 min

Lens #010 - $100 Trillion Is Changing Hands - Here's How to Catch It

Aug 3, 20265 min

301: How to Build a Cash-Flowing Business That Doesn't Rely on You with Jay Bourgana

Jul 30, 202640 min

Lens #09: My Best Investment Surprised Everyone - It Wasn't a Deal

Jul 26, 20265 min

300: What 40 Years of Failure Taught Me About Success with Cameron Herold

Jul 23, 202649 min

Lens #08: 5 Filters That Help Me Say No to Almost Every Deal

Jul 19, 20266 min

299: How PAC Helps Professional Athletes Build Meaningful Legacies Beyond Sports with Chip Paucek

Jul 16, 202651 min

Lens #07: Every Deal You See Has Already Been Rejected

Jul 13, 20266 min

298: From NFL Underdog to Thriving Entrepreneur with Justin Forsett

Jul 9, 202650 min

Lens #06: I Had Financial Freedom Before I Was a Millionaire

Jul 6, 20268 min

297: What Devin McCourty Has Learned About Managing Money After 13 Years in the NFL

Jul 2, 202654 min

Lens #05: Your Advisor Collects Fees Whether You Win or Lose

Jun 29, 20268 min

296: Turning Setbacks and Failures Into a 9-Figure Exit with Joel Marion

Jun 25, 20261h 1m

Lens #04: How the Ultra-Wealthy Actually Invest Their Money

Jun 22, 20269 min

295: The Success Trap That Keeps Entrepreneurs Unfulfilled with Rich Christiansen

Jun 18, 202634 min

Lens #03: 1,000 Lunches Taught Me More Than My Finance Degree

Jun 15, 20268 min

294: How Vertical Integration Scaled This Real Estate Firm to $5 Billion AUM with Kip Sowden & Doug McKnight

Jun 11, 202641 min

Lens #02: Why Doing "All the Right Things" Keeps You Broke

Jun 8, 20267 min

293: The Invisible Riptide That Pulls Entrepreneurial Dads Away From Their Family with Jeff Zaugg

Jun 4, 202635 min

Lens #01: 3 Shifts the Ultra-Wealthy Already Made (And You Haven't)

May 31, 20267 min

292: The Firefighter Who Walked Away From Early Retirement And Chose Entrepreneurship with Jesse Flocken

May 28, 202641 min

291: The Power of Scheduling Think Time to Unlock Peak Performance with Talor Zamir

May 21, 202646 min

290: How Franchising Is a Faster Path to Cash-Flowing Business Ownership with Jon Ostenson

May 14, 202635 min

289: The Private Credit Strategy That Creates Predictable Cash Flow with Andrea Propp

May 7, 20261h 3m

288: The Real Reason Entrepreneurs Can’t Stay Focused with Behavioral Design Expert, Nir Eyal

Apr 30, 202648 min

287: Why High Achievers Sabotage Their Relationships (And How To Fix It) with Stefanos Sifandos

Apr 23, 202645 min

286: How Tiger 21 Helps Entrepreneurs Create and Preserve Their Wealth with Michael Sonnenfeldt

Apr 16, 202654 min

Ep 285285: Why Entrepreneurs Are Turning to Functional Medicine to Optimize Their Health with Regan Archibald

There’s a big difference between building wealth and being healthy enough to enjoy it. And too often, entrepreneurs focus so heavily on growing their businesses that they unintentionally sacrifice their health and overall well-being in the process.Regan Archibald is the founder of Ageless Future and a pioneer in functional and regenerative medicine. Over the past two decades, he has worked with high-performing entrepreneurs, executives, and athletes to help optimize their health using cutting-edge medical innovations. His work focuses on identifying the root causes of health issues and helping people reclaim their energy, clarity, and vitality.In our conversation, Regan pulls back the curtain on what’s happening at the forefront of longevity and functional medicine. From breakthroughs in regenerative therapies to the growing role of peptides and personalized protocols, he explains how these innovations are helping people not just recover from injury and illness, but operate at a higher level than they thought possible.If you want to enjoy the wealth and legacy you’ve created, this episode will challenge the way you think about health, longevity, and investing in your future.In this episode, you’ll learn: ✅Why investing in your health may deliver the greatest ROI of any investment you can make.✅ How regenerative medicine, peptides, and stem cells are transforming the future of longevity.✅ Why optimizing your brain, heart, and muscle health today can dramatically impact the quality of your life in the next phase of life.Show Notes: LifestyleInvestor.com/285Tax 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.

Apr 9, 202639 min

Ep 284284: How to Elevate Your Gifting Strategy and Strengthen Business Relationships with John Israel

One of the most overlooked ways to build lasting business relationships isn’t a marketing tactic or networking event; it’s with thoughtful and intentional gifting. When done well, the right gift can create memorable experiences and strengthen relationships in ways that a generic Christmas card or gift simply can’t.John Israel is the founder of Mr. Thank You. Despite building a very successful career at Cutco, he found himself overworked, unhappy, and deeply unfulfilled. That realization sparked a bold experiment: writing five handwritten thank-you notes every single day for an entire year. What began as a personal commitment to live out the value of gratitude ultimately evolved into a global movement that helps leaders and organizations leverage appreciation and gratitude as a powerful competitive advantage.In our conversation, John shares the surprising lessons he learned from writing over 1,800 thank-you notes in one year, including how gratitude can strengthen relationships and create opportunities that money alone can’t buy. You’ll also hear how simple acts of appreciation can transform the way you lead your team, serve your clients, and build meaningful connections, both in business and in life.If you’re looking for a simple but powerful way to stand out in a crowded marketplace, this episode will challenge you to rethink how gratitude shows up in your daily habits.In this episode, you’ll learn: ✅ How leveling up your gifting game to creatively and intentionally express gratitude can become a powerful competitive advantage in business and leadership.✅ How intentional gifting can turn thoughtful ideas into unforgettable memories and create lifelong partnerships and relationships.✅ John’s Rapid Relatability Formula for building deeper connections with clients, staff, and business partners.Show Notes: LifestyleInvestor.com/284Tax 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.

Apr 2, 202633 min

Ep 283283: Why Relationships Are the Greatest Investment for Entrepreneurs with MastermindTalks Founder, Jayson Gaignard

The best asset that most entrepreneurs overlook is relationships. It’s an investment that compounds over time, and when you surround yourself with curious, like-minded people who have your back, they help you take bigger swings, and shape your personal and business trajectory in meaningful ways.For over a decade, Jayson Gaignard has been building one of the most thoughtfully curated entrepreneurial communities in the world. As the founder of MastermindTalks, he created a community and live event experience that many of today’s most respected entrepreneurs and thought leaders look forward to year after year. His philosophy is simple: relationships compound faster than capital.In our conversation, Jayson shares how investing in relationships transformed his trajectory both financially and personally. You’ll hear why he believes most masterminds miss the mark, how truly curated rooms create deeper trust and connection, and what it takes to build authentic relationships that last.Even if the price tag for the peer groups and masterminds that you want to join is too hefty, here’s one piece of advice that we both agreed on: a great way to get your network started is to build your own. And Jayson is living proof that it can be highly successful.In this episode, you’ll learn: ✅ Why relationships are the most effective and safest investment you can make, especially during downturns and uncertainty.✅ The difference between transactional networking and transformational relationships and why you need to excel at both of them.✅ How to intentionally curate your peer group so it accelerates your growth, resilience, and long-term success.Show Notes: LifestyleInvestor.com/283Tax 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.

Mar 26, 202652 min

Ep 282282: From a 9-Figure Exit to Inspiring the Next Generation of Entrepreneurs with Scott Lingle

Building a successful career in the corporate world and reaching the pinnacle isn’t easy. Walking away from that success, with four kids and looming college bills, to bet on yourself is even harder. Most people never make that leap. Fewer still build companies that exit for eight or nine figures while pursuing a life of freedom, faith, and long-term impact. That’s exactly what today’s guest did.After two decades at UnitedHealthcare, Scott Lingle made a pivot into entrepreneurship later in life, launched multiple healthcare tech companies, and had two exits — including one for nine figures in 2024. But what makes Scott’s story compelling isn’t just the financial outcome. It’s how he built businesses that didn’t depend on him, positioning him to shift from wealth creation to legacy and impact.In our conversation, we dive into his pivot toward impact, from launching High School Hustle to mentoring the next generation of entrepreneurs, and how his faith was a compass that shaped his decisions along the way.In this episode, you’ll learn: ✅ The leadership decision that allowed him to scale without sacrificing his time and sanity.✅ How finding a way to replace yourself as the top salesperson leads to exponential business growth and unlocks financial freedom.✅ Why Scott believes that using the 3% rule to invest in your personal development is the best money you’ll ever spend.Show Notes: LifestyleInvestor.com/282Tax 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.

Mar 19, 202636 min