The Lifestyle Investor - Investing, Passive Income, Wealth

Hosted by Justin Donald

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Nov 2026

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Entrepreneur Magazine calls Justin Donald “The Warren Buffett of Lifestyle Investing.” Imagine being able to earn passive income, long-term equity, and achieve financial freedom while gaining total freedom from your business or a job. That’s what Lifestyle Investing is all about. Justin Donald has mastered the low-risk cash flow investment principles he shares with entrepreneurs around the world. His alternative investing principles center on creating passive income and significant wealth while liberating yourself from a day-to-day job so you never run out of money. His innovative mindset principles and 10 commandments of Lifestyle Investing have released scores of entrepreneurs from the “golden handcuffs” that came with running life-consuming enterprises. This show focuses on showing today’s entrepreneurs and business executives how to think and invest to limit risk, maximize repeatable returns, and achieve retirement goals through his proven passive income cash flow strategies. Justin’s principles enable you to move from an “earned income” career to support your lifestyle with passive cash flow investments including real estate, operating companies, debt, equity, and franchises that give you the absolute freedom to live the life you truly desire. Interviews with top thought leaders, such as, John Lee Dumas, Ryan Levesque, Hal Elrod, Jon Vroman, Mike Koenigs, Phillip Stutts, Rob Dial, John Ruhlin, Brad Johnson, Robert Glazer, Mike Michalowicz, Geoff Woods, Steve Sims, and many more! For more information, visit https://justindonald.com ]]>

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November 9, 20265 min

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

Someone builds a $20 million business, sells it, and inside 7 years most of that money is gone. It happens constantly, and it isn't because they got unlucky. It's because making money and keeping money are completely different skills, and almost nobody who is great at the first one ever bothers learning the other three. This is my adaptation of Robert Kiyosaki's Cashflow Quadrant, reworked into the four money games I think every entrepreneur is actually playing whether they realize it or not. In this video I break down: → Make. Earning income and building the business, which is the quadrant most founders are already exceptional at and mistakenly assume will carry them through the rest → Manage. What you actually keep after taxes, expenses and capital allocation, and why entrepreneurs who make a million and spend 1.2 million have a management problem rather than an income problem → Multiply. Deploying capital into things that compound without you, and why founders who can force outcomes through sheer will tend to be the worst investors in the room → Matter. What the surplus is for, the quadrant almost nobody reaches, and why waiting until you have $100 million to ask the question is the wrong order I also cover the shift that changed this for me, which was giving up on being great at all four and building teams around the three I was never going to be naturally good at. A fractional CFO for managing. People who had actually made money in private equity and real estate for multiplying. And time spent around people playing the giving game at a level I'd never seen, like David Weekley, who has given away half of everything for 35 years. You don't need to master all four. You need to be aware of all four and intentional about each one. 👉 Subscribe to The Lifestyle Investor Lens: https://lifestyleinvestor.com/lens Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today. Nothing here is financial advice. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

November 5, 202646 min

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

Behind almost every great success story are people who helped make it possible. Mentors who offered guidance, friends who provided encouragement, and communities that opened doors to new opportunities. But success isn't just about what you accomplish. It's also about the people you surround yourself with and the relationships that make the journey worthwhile. Today's guest is Phoebe Mroczek, a longtime friend and the marketing mastermind behind what we've been building at Lifestyle Investor. Phoebe is an entrepreneur, marketing strategist, and podcaster who has helped us transform how we connect with our audience, grow our community, and share the message of financial freedom with more people. Phoebe's journey is especially meaningful to me because I've had the privilege of knowing her long before she joined our team. After surviving a life-threatening accident that left her struggling with memory loss and cognitive challenges, she developed a completely different perspective on life, purpose, and what it means to make an impact. In our conversation, Phoebe shares some of the biggest lessons from her personal journey, including a recent darkness retreat that challenged her relationship with peace and uncertainty. We also talk about the evolution of Lifestyle Investor, what makes a truly exceptional community, the importance of surrounding yourself with people who share your values, and why the most meaningful success comes from building a life centered around the things that matter most. In this episode, you’ll learn: ✅ How Phoebe's near-fatal accident transformed her perspective on adversity and finding purpose in difficult experiences. ✅ Why building a successful community requires prioritizing the right people over rapid growth. ✅ How authentic marketing and shared values can create deeper connections and a more meaningful impact. Show Notes: LifestyleInvestor.com/313 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

November 2, 20266 min

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

That's the part of the Trump accounts nobody is talking about, and it's why the free $1,000 is the least interesting thing about them. Here's the math. Fund one to the $5,000 annual cap through the growth period at a 10% return and your kid has roughly $225,000 by 18. Then you stop. Never add another dollar. That balance keeps compounding for another 42 years and crosses $12 million by 60, from money you finished contributing before they could legally buy a drink. Most people are going to take the $1,000, park it, and never think about it again. That's the expensive version of this. In this video I break down: → The contribution rules, including why the $1,000 federal seed for kids born 2025 through 2028 sits on top of the $5,000 cap instead of eating into it → The business owner angle: routing $2,500 a year through your company, deductible to the business and excluded from your income, so half the contribution comes from pre-tax dollars → The Roth conversion almost nobody is discussing, and why deferral alone has never been the finish line for me → How a college kid with little income converts slices at 0%, walking the balance into tax-free territory a piece at a time → Why teaching it matters more than funding it, because your kid controls this account at 18 and a quarter million landing on someone who has never thought about compounding is a risk rather than a gift One honest caveat before you build a plan on this. It's brand-new legislation and Washington rewrites these things, so build on the principle rather than the fine print. CHAPTERS: 00:00 The $12 million nobody mentions 01:00 What $5,000 a year actually turns into 02:30 The contribution rules and the business owner angle 04:00 Deferral versus elimination, and the Roth conversion 06:00 Why teaching it matters more than funding it 07:30 Assume the rules change, build on the principle 👉 Subscribe to The Lifestyle Investor Lens: https://lifestyleinvestor.com/lens Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today. Nothing here is financial or tax advice. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

October 29, 20261 hr 20 min

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

You can have a great CPA, a trusted wealth manager, and an experienced attorney, and still be making costly mistakes with your wealth. The problem isn't necessarily the people you've hired. It's that each advisor may be doing a great job individually, while nobody is making sure they're all working together. And those gaps can quietly cost you millions in missed tax savings, poor investment decisions, unnecessary risks, and estate planning mistakes. That's why today's episode is a little different. I'm sharing a recent live training I hosted with Dane Espegard, our Head of Membership at Lifestyle Investor, where I break down the five wealth traps that even successful entrepreneurs and investors often overlook. I'll show you how the wealthiest families approach managing and protecting their money, why having multiple financial advisors doesn't necessarily mean you have a coordinated wealth strategy, and how to identify the gaps that could be holding you back. You'll also discover why I believe financial freedom is far more important than net worth, and how to start thinking about your wealth the way a family office does, without needing a billion-dollar fortune. Ready to Build Wealth That Buys You Freedom? Join the Lifestyle Investor Mastermind to access exclusive investment opportunities, advanced tax strategies, and a trusted network of like-minded investors. Learn more and request an invitation: https://lifestyleinvestor.com/mastermind/ In this episode, you’ll learn: ✅ The five hidden wealth traps that could be quietly costing you millions, even if you're already working with top financial advisors. ✅ Why traditional wealth management may be leaving you exposed, and what the wealthiest families understand about taxes, investments, asset protection, and generational wealth that others overlook. ✅ How to uncover the biggest gaps in your financial strategy using a simple 25-point scorecard, and why fixing them could be more valuable than finding your next great investment. Show Notes: LifestyleInvestor.com/312 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

October 26, 20264 min

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

Ten years ago the goal was always the same. Build the company, ring the bell, take it public. That was the entire endgame and everyone organized around it. Today most of the companies people actually want to own are avoiding the public markets completely. Uber stayed private for 9 years. Airbnb for 11. Stripe is worth over $95 billion and still hasn't listed. OpenAI is still private. If you're waiting on IPO liquidity to deploy capital, you're waiting on something that's happening less and less every year. In this one I break down where that money went instead, and why the secondary market has grown into the trillions while most retail investors have never heard of it. Founders and early investors still need liquidity long before an exit, so they sell already-issued shares to someone else, and the buyer gets Series C or D upside with a better risk profile than early-stage. The biggest institutions in the world are already there. Blackstone, Goldman, Berkshire. In certain niches like defense tech, the largest buyer is the government itself, which tells you plenty about where capital is actually flowing. I also share numbers from a secondaries-focused fund I'm involved with. 50% gross IRR over roughly five years, 14 out of 14 investments returning positive, exposure to 5 unicorns. Everyone is fighting over the next seed round while the less crowded opportunity sits one stage later. CHAPTERS: 00:00 The playbook changed and nobody announced it 01:00 Why companies stay private for 10 years now 02:30 How a secondary transaction actually works 04:00 Who's buying, and why the institutions moved first 05:30 What this changes about where you put capital 👉 Subscribe to The Lifestyle Investor Lens: https://lifestyleinvestor.com/lens Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today. Nothing here is financial advice. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

October 20, 20265 min

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

The government reports a number every month and most people treat it as the truth. 2.8%, 3%, whatever it happens to be that quarter. Meanwhile the dollar itself is losing value at a completely different rate, and the gap between those two figures is where your savings are going. In this one I break down the difference between inflation and debasement, and why only one of them tells you what your money is actually worth. Gold near $4,900, Bitcoin at $72,000, silver at $77. Those moves are telling you something about the dollar that the reported figures are not. I also walk through the three categories I think about. Cash and bonds, which lose to debasement every year. Productive assets like stocks, real estate and crypto, which can keep pace. And leveraged positions on specific trends, which can outpace it with more risk attached. Most people sit almost entirely in the first category and call it saving. When debt grows faster than GDP, printing becomes the easiest way to service it regardless of who's in office, and that pressure lands in asset prices. CHAPTERS: 00:00 Inflation and debasement are not the same word 00:50 What the reported number actually measures 02:10 What 10% a year costs you sitting in cash 03:30 The three categories your money can sit in 05:10 Why more printing is coming, and your decision 👉 Subscribe to The Lifestyle Investor Lens: https://lifestyleinvestor.com/lens Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today. Nothing here is financial advice. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

October 20, 202638 min

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

Growing a business is one thing. Building a business that can sustain that growth without everything falling apart is another. As companies grow, the challenges change. Decisions pile up, priorities get confused, talented employees become frustrated, and founders often find themselves working harder than ever just to keep everything moving. That's why I'm excited to welcome my longtime friend Cathy Christen to the podcast. Cathy is the founder and CEO of Elevated You, a leadership and culture strategist, and has spent more than 20 years building businesses, developing leaders, and helping entrepreneurs create stronger teams and company cultures. She's also the author of The SCALE Advantage, which explores the five essential pillars of building a high-performing company to help businesses grow without sacrificing the people who make that growth possible. In our conversation, Cathy shares how a conversation we had more than 20 years ago completely changed her approach to entrepreneurship and helped her escape the workaholic lifestyle she'd created. We also discuss the lessons we've learned from hiring the wrong people, the challenges of keeping teams aligned as businesses grow, and why the human side of business may become even more valuable as AI continues to transform the workplace. In this episode, you’ll learn: ✅ How Cathy’s SCALE framework helps entrepreneurs build stronger teams, improve accountability, and create sustainable growth. ✅ The hidden financial costs of poor company culture , including lost talent, wasted time, and the leadership mistakes that can quietly destroy an otherwise successful business. ✅ Why great employees, better systems, and new technology aren't enough to scale successfully , and what it takes to create a team that can execute without your constant involvement. Show Notes: LifestyleInvestor.com/311 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

October 5, 202639 min

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

Generating passive income and generational wealth isn't always about finding the next big investment or coming up with a million-dollar business idea. In most cases, it's about making a series of intentional decisions with your money, building surplus income, and consistently putting it to work. That's what makes Michael Alberse's story so inspiring. Michael went from living in a self-built van while working as an Account Manager at Google to growing his net worth to $1.4M, creating multiple income streams that generate thousands of dollars in passive income every month. And most recently, Michael founded Trailmix Wealth, which helps everyday people build real wealth while enjoying the journey. Michael's journey is especially meaningful to me because reading The Lifestyle Investor was the launchpad that changed how he thought about investing. He eventually became one of the first members of our Foundations program and the first to make the jump into Tribe of Investors. In our conversation, Michael shares how he aggressively saved and invested early in his career, turned his Google Ads expertise into a cash-flowing business, and started building a diversified portfolio outside of the stock market. We also unpack some of his biggest wins and mistakes as an investor, the importance of learning from people further ahead of you, and why he's ultimately building wealth around the life he wants to live. In this episode, you’ll learn: ✅ How creating surplus income and consistently reinvesting it can accelerate your path to financial freedom. ✅ Why Michael built a cash-flowing business that now requires only a few hours of his time each month. ✅ What Michael's biggest wins and losses in private investments taught him about deal structure and due diligence. Show Notes: LifestyleInvestor.com/310 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

September 24, 202633 min

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

Entrepreneurship can provide incredible wealth and freedom, but not if you've created a company that can't function without you. When every important decision, client relationship, and responsibility runs through you, then you've essentially traded one job for another while limiting the value of the business you've worked so hard to build. That's why I'm excited to have Eric Rozenberg on the podcast. Eric is an entrepreneur, author, speaker, and consultant who has spent nearly three decades building, scaling, and exiting businesses in the meetings and events industry. Along the way, he's learned firsthand what happens when entrepreneurs try to do everything themselves and what it takes to build a company that creates freedom instead of consuming your life. Eric's experience is particularly interesting as AI transforms how businesses operate while making genuine human relationships and face-to-face connections even more valuable. In our conversation, Eric shares his journey from corporate life to entrepreneurship, why people often choose misery over the uncertainty of change, and how AI could make in-person communities and events even more important. In this episode, you’ll learn: ✅ Why reducing your involvement in the business can increase its value while giving you more freedom. ✅ How defining a compelling 10-year vision can help you make difficult decisions and stay aligned during the inevitable ups and downs of entrepreneurship. ✅ How asking yourself “Should I be the one doing this?” can help you delegate more effectively and build a business that doesn't depend on you. Show Notes: LifestyleInvestor.com/309 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .

September 17, 202654 min

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

Building a successful company can create generational wealth. But once you've had a big exit, figuring out how to invest that money without taking unnecessary risks can be more challenging than many people would think. That’s why I'm excited to have Ben Rubenstein on the podcast. Ben is a serial entrepreneur, investor, and the founder and Principal of SetPoint Capital, an asset-backed private credit platform and technology company. He’s had multiple 9-figure exits after co-founding Yodle, which sold for $342 million, and Opcity, which sold for $210 million. Today, Ben brings his experience as both an operator and investor to building technology and investment strategies across real estate, fintech, and private credit. In this conversation, we discuss the lessons Ben learned from scaling and exiting multiple companies and why he believes great businesses are built around customers rather than ideas. We also talk about what separates safer forms of private credit from the risks making headlines today, and how his experience on both sides of the table has shaped how he thinks about investing his own wealth. In this episode, you’ll learn: ✅ Why Ben uses a barbell approach to investing that combines safer cash-flow investments with concentrated opportunities where he has a competitive advantage. ✅ How asset-backed lending, aligned incentives, and new technology can create additional layers of protection for private credit investors. ✅ Why deep due diligence becomes even more important as investors move beyond traditional stocks and bonds into alternative investments. Show Notes: LifestyleInvestor.com/308 Tax Strategy Masterclass If you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/tax Strategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultation The Lifestyle Investor Insider Join The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insider Rate & Review If 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 Donald Facebook YouTube Instagram LinkedIn Twitter See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info .