Afleveringen
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What if you could tap into the exact investment strategies billionaires use to multiply their wealthâwithout being one?
In this episode, Iâm 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 worldâs largest network of ultra-wealthy investors.
Today, heâs sharing what heâs 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, youâll discover the exact strategies billionaires useâand how to apply them to grow your own wealth, no matter where you're starting.
In this episode, youâll learn:
1.) How Richard built the #1 investor club for billionairesâand the exact mental models heâs seen them use to spot better deals and scale with precision.
2.) What heâs learned from interviewing hundreds of billionaires and centi-millionairesâincluding 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/243
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 todayâs 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
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Most people are chasing a retirement plan theyâll never enjoy â or even want. Derek Coburn is here to show you a more meaningful path that doesnât 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 âunretirement,â and why fulfillment doesnât come from chasing a number⊠but from showing up with purpose.
He also shares the story behind his newly released book, Letâs 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, youâll learn:
1.) Why 1 in 3 retirees return to work â and how to design a life you never want to retire from instead.
2.) The hidden risks of 401(k)s â plus the tax strategies wealthy investors are using to protect their future income.
3.) The time machine exercise that redefined Derekâs relationship with time, money, and fatherhood â and how you can create special moments in your own life.
Show Notes: LifestyleInvestor.com/242
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Zijn er afleveringen die ontbreken?
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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, Iâm joined by Garrett Gunderson and Brad Weimert for a wide-ranging roundtable on building wealth in todayâs fast-changing world.
We dive into big topicsâfrom AIâs 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 dealsânot just by offering more money, but by understanding seller psychology and waiting for the right moment.
In this episode, youâll learn:
1.) How AI is Reshaping the Future of Education and Work
From publishing and teaching to legal and finance, discover where AI is replacing humansâand where itâs not.
2.) Why the Smartest Investors Are Going All-In on Private Markets
Learn 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 Market
Itâs not always about priceâsee how relationships, timing, and seller psychology can unlock the best opportunities.
Show Notes: LifestyleInvestor.com/241
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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I used to believe the key to success was working harder than everyone else.
And for a while, that served me. But over time, I started asking different questionsâlike what would it look like to build a life where work didnât come at the expense of family, faith, or freedom?
This episode is a little different, as Iâm the one being interviewed. Preston Brown, host of the Problems to Profit Podcast, pulls out the biggest lessons Iâve learned, from selling newspaper subscriptions in middle school to investing in private deals that create passive income and real-time freedom today.
We get into why I prioritize passive income over net worth, and how relationships and masterminds have opened the door to some of my biggest opportunities.
In this episode, youâll learn:
1.) How one passive income deal replaced my wifeâs incomeâand how that one move kickstarted our journey to financial freedom.
2.) My personal framework for allocating surplus income into deals that create long-term freedom.
3.) Why I created The Lifestyle Investor Mastermindâan exclusive community giving members access to the same deals and strategies used by the ultra-wealthy.
Show Notes: LifestyleInvestor.com/240
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Every founder dreams of the big exit. But few are prepared for what comes next.
Todayâs guest learned the hard way. Anastasia Koroleva sold her company for 9-figures, but instead of feeling free, everything got more complicated.
She lost her identity. Made costly investment mistakes. And her marriage broke under the weight of post-exit stress.
In this honest conversation, Anastasia opens up about the emotional aftermath of selling a business and the hidden challenges that come with sudden wealth.
Youâll learn why wealth often brings confusion instead of clarity, how overconfidence leads to poor investment decisions, and the patterns sheâs uncovered from interviewing hundreds of founders after theyâve successfully exited their business.
If you're building toward an exit â or learning how to invest after one â this is the conversation most people wish theyâd heard sooner.
In this episode, youâll learn:
â Why financial freedom doesnât always equal happinessâand the steps you can take to avoid feeling of emptiness post-exit.
â How to avoid common post-exit mistakes of investing in VC or angel investing without proper due diligence.
â The benefits of raising children who arenât entitled and teaching them about taking risks, the benefits of entrepreneurship and not being afraid to fail.
Show Notes: LifestyleInvestor.com/239
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Imagine that you're an entrepreneur who's already had an exit. You're working on a Master's degree at MIT's Entrepreneur Program, and then you get a call from a talent scout at Shark Tank.
Not only that, but that phone call landed you a million-dollar investment from the Sharks for your restaurant business (still one of the top five deals ever to this day) and a seven-figure exit a few years later.
That's just scratching the surface of why I'm excited to introduce you to my friend Yuen Yung. Yuen is a serial entrepreneur, investor, and the Co-Founder of HalBar Partners, a niche private equity firm specializing in a relatively unknown but powerful asset class: Search Funds.
In our conversation, you'll hear the experience Yuen has gained from having several successful exists, why he believes that alternative investments and real estate offer better ROI and security than the public markets, and why his newest venture into search fundsâan asset class averaging a 35% IRRâcould be a game-changer for investors seeking higher multiples with the steady returns of private equity.
In this episode, youâll learn:
1.) Why traditional stock market investing with 60/40 portfolios feels outdatedâand why the ultra-wealthy are investing their money in alternative investments.
2.) What Search Funds are and why this niche asset class differs from the more common private equity and venture capital investment opportunitiesâand why most people have never heard of them.
3.) How Yuen earned a $1 million dollar investment on Shark Tank, despite initially turning down the opportunity and how he turned it into a 7-figure exit.
Show Notes: LifestyleInvestor.com/238
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Imagine signing a $10M contract, only to see $2M after taxes, fees, and cuts?
Thatâs the reality for most pro athletes. And for many, itâs just the beginning of financial missteps that can lead to bankruptcy just a few years after retiring.
Todayâs guest is Tom Zhengâa former NFL sports scientist turned investor. Heâs also the Co-Founder & CEO of The Players Company, a platform helping professional athletes build real wealth through education, access, and smart investments.
In this episode, Tom shares a behind-the-scenes look at how professional athletes are financially coached (or often misled), the growing role of private equity in sports, and how heâs guiding athletes toward smarter financial futures through education and access to exclusive investment opportunities.
Whether youâre a sports fan, investor, or entrepreneur, this episode is packed with lessons about leverage, legacy, and building financial intelligence.
In this episode, youâll learn:
1.) How Tom went from NFL sports science to investing in pro teams and building a player-owned private equity firm.
2.) The financial traps most pro athletes fall intoâand how The Players Company is solving them.
3.) Why investing in sports teams and NIL assets isnât just for billionaires anymoreâand what this means for everyday investors.
Show Notes: LifestyleInvestor.com/237
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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What if every decision you made was actually predetermined, shaped by a story your nervous system wrote years ago?
Well, the science suggests that our emotional programming starts in the womb.
Todayâs guest calls it the âghost in the machineâ and has spent 20+ years helping people rewrite it.
In this episode, Iâm talking with Joey KleinâFounder of Inner Matrix Systems and a globally recognized transformation expert. Joey has trained over 84,000 people, from Fortune 500 execs to pro athletes, to rewire the emotional and mental patterns quietly shaping their behavior. His work blends neuroscience, psychology, and mindfulness to create real, lasting change from the inside out.
Together, we explore how these subconscious imprints silently drive your decisionsâoften sabotaging success in business, relationships, and everyday life.
If you want to rewire your inner programming, get unstuck, and create meaningful success in every area of life, youâre going to love this episode.
In this episode, youâll learn:
â How a near-death experience at 19 launched Joey's journey into inner workâand why emotional mastery, not hustle, is the key to lasting success.
â What the âghost in the machineâ really isâand how subconscious emotional imprinting silently drives your decisions.
â How Joey helped a top Hollywood executive break through years of creative roadblocks by rewiring his internal belief system.
â Why your nervous system is just as trainable as your musclesâand how to strengthen it to access clarity, calm, and peak performance.
Show Notes: LifestyleInvestor.com/236
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Most people run from problems. Preston Brown builds businesses around them.
He believes every sale is simply a solution to a problemâand if you can solve enough of them, you can build real wealth without sacrificing your time, health, or freedom.
Preston is a prolific entrepreneur and systems thinker who automates, optimizes, and scales companies across real estate, lending, construction, and service industries. Heâs built a 9-figure portfolio of cash-flowing businesses by identifying everyday frustrations and turning them into opportunities through strong systems and self-managed teams.
In this episode, youâll learn how Preston structures his businesses so they donât depend on him to operate, how to spot hidden profit leaks in your operations, and how to turn recurring problems into scalable income streamsâall while freeing up your time to focus on what matters most.
In this episode, youâll learn:
1.) The â4 Flows of Capacityâ framework that fixes broken businesses fast
Most business owners donât know where theyâre bleeding time, money, or energy. Preston shares his simple but powerful systemâLeads, Sales, Delivery, Cashâand how identifying the weakest link in these flows can unlock exponential growth.
2.) Why Return on Time (ROT) is the new ROIâand how to design your business around it
Youâll learn how Preston optimizes for time freedom, not just profitâand how applying ROT, ROM (Return on Marketing), and ROE (Return on Emotion) has helped him build a business portfolio that supports his lifestyle, not consumes it.
3.) How he turned a $12M lawsuit into the best thing that ever happened to his company
When a shady developer put Prestonâs real estate empire at risk, he couldâve folded. Instead, he went public, led with integrity, and earned even more trust from banks and partnersâproving that doing the right thing when no oneâs looking is the ultimate business strategy.
Show Notes: LifestyleInvestor.com/235
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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If you're grinding through life just to someday 'retire,' you're doing it wrong.
Today, Iâm talking with Garrett Gundersonâa best-selling author, speaker, and financial disruptorâabout what it really takes to build freedom now, not 30 years down the road.
Garrettâs helped thousands of entrepreneurs grow their wealth without sacrificing their lifestyle. Heâs trained top financial professionals, revived the timeless wealth principles of the Rockefellers, and developed practical frameworks that simplify the money gameâso you can build wealth on your terms.
In this episode, we break down what Garrett calls The Trifectaâa proven system for becoming financially fit, reaching true independence, and unlocking a level of freedom that's only possible when you change the way you think, not just the way you invest.
In this episode, youâll learn:
â How to use whole life insurance, trusts, and asset protection to build generational wealth like the Rockefellers.
â Why true financial independence starts in your mindânot your bank account.
â Garrettâs Trifecta Framework for building wealth, protecting assets, and creating true freedom.
Show Notes: LifestyleInvestor.com/234
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Most people lose money in real estate syndications for one reason: they donât know how to properly vet a deal.
In this episode, I sit down with Hans Box to unpack the exact questions savvy investors should ask before wiring funds to a sponsor.
Hans is the Co-Founder of Box Wilson Equity, which has invested has invested $95MM+ in equity across various asset classes, including multifamily, self-storage, mobile home parks, distressed debt, office, and preferred equity. And heâs personally been involved in the acquisition, investment, and management of over $350MM in multifamily and self-storage assets.
Together, we break down how to assess risk, spot red flags in offering documents, and why alignment, transparency, and track record matter more than hype or projected returns.
Whether youâre considering your first deal or refining your due diligence process, this conversation will help you make smarter, safer investment decisions in the world of syndications.
In this episode, youâll learn:
1.) The #1 reason investors lose money in syndicationsâand how to avoid it by reverse-engineering a dealâs risk through the capital stack, pro forma, loan terms, and sensitivity analysis.
2.) Why âprojected returnsâ are a trapâand what smart investors look at instead, including sponsor alignment, track record, deal structure, and the questions that reveal the truth before you wire a dollar.
3.) The hidden red flags most investors miss inside the fine print, from manager replacement clauses to preferred equity termsâand how reading between the lines of the PPM could save you from disaster.
Show Notes: LifestyleInvestor.com/233
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Whole Life Insurance is widely misunderstood, yet for billionaires and family offices, itâs a powerful tool for long-term financial security.
While most people see life insurance as an expense, the wealthy use Whole Life Insurance as a financial foundationâone that offers liquidity, tax-free growth, and a guaranteed rate of return.
In this episode, Caleb Guilliams, founder of BetterWealth, joins me to break down the real benefits of Whole Life Insuranceâand how to use it the way the wealthy do.
We discuss why most policies are structured incorrectly, the biggest mistakes to avoid, and why banks and billionaires hold massive amounts of Whole Life Insurance as part of their asset allocation strategy.
In This Episode, Youâll Learn:
1.) Why Whole Life Insurance isnât an investmentâand how the wealthy use it to build lasting financial security.
2.) The truth about Whole Life Insuranceâthe key benefits, hidden pitfalls, and the biggest misconceptions that trip people up.
3.) The costly mistakes people make when setting up a Whole Life policyâand how to structure yours for maximum flexibility and returns.
Show Notes: LifestyleInvestor.com/232
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Most pro athletes go broke after retiring. Devon Kennard isnât one of them.
As an NFL linebacker turned real estate investor, Devon made the rare transition from W-2 income to building an 8-figure real estate portfolioâall while still playing in the league. Seeing how easily athletes could be replaced, he knew he needed a plan for financial independence before his playing days were over. While many players burn through their earnings, Devon took a different approach, learning to invest, creating passive income, and setting himself up for long-term wealth.
In this conversation, Devon breaks down how he navigated the world of investing while maintaining a demanding career in professional sports. He shares the biggest financial mistakes athletes (and high-income earners) make, why most people are underestimating their risk of being replaced, and how he built a diversified investment strategy that generates cash flow without requiring his constant attention.
Devon also explains the mindset shifts that helped him overcome financial setbacks and why learning from other people's mistakes is the fastest way to accelerate wealth.
In this episode, youâll learn:
1.) The biggest money traps that cause pro athletes and high-income earners to go broke, and the simple shifts that can keep you financially free for life.
2.) The 4 real estate strategies that helped Devon build an 8-figure portfolio while playing in the NFLâincluding the red flags to look for when vetting deals.
3.) How Devon escaped the W-2 paycheck cycle and built passive income while still workingâand why waiting too long to start could be your biggest financial mistake.
Show Notes: LifestyleInvestor.com/231
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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So youâve sold your businessâwhatâs your next step?
Most entrepreneurs spend years building their businesses, but when they finally exit, they struggle to transition from managing staff and emails to all the investing opportunities they now have.
In todayâs episode, Iâm sitting down with Dr. Tony Jacobâan entrepreneur who scaled and exited the largest private optometry roll-up in Texas history. After his exit, Tony faced the challenge of shifting from business owner to capital allocator, learning firsthand the risks of rushing into investments, the importance of patience, and how to structure a family office for long-term wealth preservation.
Weâre diving into how to avoid the common pitfalls of post-exit investing, how to build a bulletproof asset allocation strategy, and the growing role of Bitcoin in family office portfolios.
If youâre an entrepreneur preparing for an exitâor youâve already sold and want to make smarter financial decisionsâthis episode is a must-listen.
In this episode, youâll learn:
The biggest investing mistakes post-exit entrepreneurs makeâand how to avoid them.Why capital preservation is just as important as wealth creationâand how to structure your portfolio to last generations.Why Bitcoin is becoming a strategic asset for family offices and institutional investors.Show Notes: LifestyleInvestor.com/230
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Private credit has been around for centuries, but in recent years, it has surged in popularityâespecially among the worldâs wealthiest investors. Family offices and institutional investors are shifting away from traditional fixed income and embracing private credit for higher returns, stronger downside protection, and better diversification.
Today, Iâm sitting down with Peter Sack, co-founder and partner at Chicago Atlantic, one of the largest private credit firms in the U.S. Chicago Atlantic has deployed over $2 billion in cannabis private credit alone, with additional investments in venture debt, digital infrastructure, and lower middle-market lending.
In this conversation, Peter breaks down why private credit is booming, how it compares to traditional fixed income, and where the best opportunities exist today. If youâre looking to diversify your portfolio and invest like the ultra-wealthy, this episode is a must-listen.
In this episode, youâll learn:
â Why family offices are increasing their allocation to private credit.
â How private credit offers equity-like returns with lower risk.
â The impact of rising interest rates on private lendingâand why banks are failing to keep up.
â How Chicago Atlantic structures private credit deals, including high-yield lending & equity kickers.
Show Notes: LifestyleInvestor.com/229
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Too many business owners wake up the day after selling their company with one regret: 'I could have gotten more.' The difference between an average exit and a life-changing one comes down to strategyâand today, weâre diving deep on how to get it right.
Iâm sitting down with Chad Morissette, an M&A expert who has advised on hundreds of business sales and helped founders maximize their exits. Unlike many advisors, Chad and his entire team have personally built and sold their own companiesâmeaning they actually understand what it takes to position a business for an optimal sale.
In this conversation, Chad breaks down the most common mistakes sellers make, the factors that determine a companyâs true value, and how to ensure youâre not leaving money on the table when itâs time to exit.
Whether youâre years away from selling or already fielding offers, this episode will help you secure the best deal possible.
In this episode, youâll learn:
â The #1 reason most founders regret their exitâand how to avoid it.
â Why your company is probably worth less than you thinkâand how to change that.
â The key factors buyers look for when valuing a business (itâs not just revenue).
â Why working with an M&A advisor can mean millions more in your pocket.
Show Notes: LifestyleInvestor.com/228
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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If you donât have an assistant, you ARE the assistant.
Thatâs the reality for most entrepreneursâstuck handling emails, booking travel, and drowning in admin work instead of focusing on what actually grows the business.
In this episode, Iâm sitting down with Tricia Sciortino, CEO of BELAYâa staffing agency that specializes in hiring top-tier virtual executive assistants, bookkeepers, and other remote talent to help business owners buy back their time and scale faster.
Weâre talking all about how hiring the right executive assistant isnât an expenseâitâs the key to unlocking your next level of growth.
Tricia started as the first-ever virtual assistant at BELAY and worked her way up to CEOâso she knows firsthand the impact of smart delegation. Before that, she was Michael Hyattâs original EA, playing a key role in helping him scale what is now Full Focus, a multimillion-dollar leadership training company. Sheâs had a front-row seat to how top entrepreneurs leverage assistants to maximize productivity and growthâand today, sheâs pulling back the curtain to share those insights with us.
In this episode, youâll learn:
â Why NOT hiring an EA is actually costing you moreâand how itâs limiting your business growth.
â How AI is transforming the role of executive assistantsâand how to use it to streamline operations, boost productivity, and scale faster.
â A step-by-step framework to start delegating today, so you can focus on high-value activities and stop being your own assistant.
Show Notes: LifestyleInvestor.com/227
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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If you want to build long-term wealth and protect your money from market volatility, todayâs guest has the tools to show you how to do it by using hard assets and smart investing strategies.
Ben Reinberg, is one of the leading experts in commercial real estate and the founder of Alliance Consolidated Group, a firm he built from scratch to become a $500M empire that has managed billions in transactions across medical offices, industrial, and multifamily real estate. In his newest book, Hard Assets and Hard Money for Hard Times, he lays the blueprint for building a hard asset empire.
With over 30 years of experience, Ben explains why real estate is the best vehicle for building wealth, how to invest passively by focusing on your niche, and why leveraging relationships is the key to long-term success.
Whether you're an experienced investor or just starting out, this episode is packed with invaluable insights that can help you grow and protect your wealth.
In this episode, youâll learn:
â The one real estate asset class that will have the biggest opportunities in 2025âand why most investors are overlooking it.
â How Ben turned a single deal into a 3X returnâand the investing strategy he still swears by today.
â The 3 most powerful wealth levers you can use to scale your investments fasterâwith less of your own money.
Show Notes: LifestyleInvestor.com/226
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Are you stuck in the Wall Street mindset and looking for better ways to grow and protect your wealth?
In this episode, Iâm sitting down with M.C. Laubscher, founder of Cashflow Ninja and author of Get Wealthy for Sure: The #1 Financial Strategy for Business Owners to Multiply Wealth Predictably. M.C. is an expert in alternative investments, teaching entrepreneurs how to think outside the traditional financial box to create lasting financial freedom.
We dive into why alternative investments outperform traditional options, how to shield your wealth from inflation and taxes, and why understanding the difference between saving, investing, speculating, and gambling is critical to your financial success.
Whether youâre new to alternative investing or a seasoned investor looking to refine your strategy, this conversation is packed with insights to help you thrive in uncertain markets.
In this episode, youâll learn:
â Why family offices allocate up to 59% of their portfolios to alternative investments
â How to navigate inflation, market volatility, and tax threats with defensive strategies
â The power of inefficient markets and the asymmetric opportunities they offer
â How to create a âsleep-well-at-nightâ cash strategy while still capitalizing on investment opportunities
Show Notes: LifestyleInvestor.com/225
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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Building wealth isnât just about what you doâitâs about how you think. And the ultra-wealthy know that financial success starts in the mind.
Thatâs exactly what todayâs guest, Bronson Hill, discovered after interviewing over 2,500 millionaires. Through those conversations, he uncovered the habits, mindsets, and investment strategies that separate everyday earners from those who achieve true financial freedom.
A former medical sales professional, Bronson walked away from a high-paying career to pursue passive income, scaling his wealth 20X in just a few years. Bronson is a general partner in 2,500 multifamily units worth over $250M, and has personally raised over $45M for real estate and private equity deals.
In this episode, we dive deep into the psychology of wealth, why who you surround yourself with determines your financial future, and the hidden investment strategies the ultra-wealthy use to build lasting fortunes.
In this episode, youâll learn:
â The mindset shift that helped Bronson 20X his net worthâand the surprising reason most people stay broke.
â How 2,500 millionaires built their wealthâand the biggest investing mistakes to avoid.
â The investment strategy ultra-wealthy investors use to outperform the stock market.
â The hidden âWealth-Worthinessâ belief that silently holds most people back from financial freedom.
Show Notes: LifestyleInvestor.com/224
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 todayâs 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
FacebookYouTubeInstagramLinkedInTwitterSee 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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