The Lifestyle Investor - Investing, Passive Income, Wealth

Private credit has been around for centuries, but in recent years, it has surged in popularity—especially among the world’s 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, I’m 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 you’re looking to diversify your portfolio and invest like the ultra-wealthy, this episode is a must-listen.In this episode, you’ll learn:✅ Why family offices are increasing their allocation to private credit.✅ How private credit offers equity-like returns with lower risk.✅ The impact of rising interest rates on private lending—and why banks are failing to keep up.✅ How Chicago Atlantic structures private credit deals, including high-yield lending & equity kickers.Show Notes: LifestyleInvestor.com/229Tax Strategy MasterclassIf you're interested in learning more about Tax Strategy and how YOU can apply 28 of the best, most effective strategies right away, check out our BRAND NEW Tax Strategy Masterclass: www.lifestyleinvestor.com/taxStrategy Session For a limited time, my team is hosting free, personalized consultation calls to learn more about your goals and determine which of our courses or masterminds will get you to the next level. To book your free session, visit LifestyleInvestor.com/consultationThe Lifestyle Investor InsiderJoin The Lifestyle Investor Insider, our brand new AI - curated newsletter - FREE for all podcast listeners for a limited time: www.lifestyleinvestor.com/insiderRate & ReviewIf you enjoyed today’s episode of The Lifestyle Investor, hit the subscribe button on Apple Podcasts, Spotify, or wherever you listen, so future episodes are automatically downloaded directly to your device. You can also help by providing an honest rating & review.Connect with Justin DonaldFacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Too many 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 strategy—and today, we’re diving deep on how to get it right.I’m 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 companies—meaning 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 company’s true value, and how to ensure you’re not leaving money on the table when it’s time to exit.Whether you’re years away from selling or already fielding offers, this episode will help you secure the best deal possible.In this episode, you’ll learn:✅ The #1 reason most founders regret their exit—and how to avoid it.✅ Why your company is probably worth less than you think—and how to change that.✅ The key factors buyers look for when valuing a business (it’s not just revenue).✅ Why working with an M&A advisor can mean millions more in your pocket.Show Notes: LifestyleInvestor.com/228Tax 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.

If you don’t have an assistant, you ARE the assistant.That’s the reality for most entrepreneurs—stuck handling emails, booking travel, and drowning in admin work instead of focusing on what actually grows the business.In this episode, I’m sitting down with Tricia Sciortino, CEO of BELAY—a 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.We’re talking all about how hiring the right executive assistant isn’t an expense—it’s 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 CEO—so she knows firsthand the impact of smart delegation. Before that, she was Michael Hyatt’s original EA, playing a key role in helping him scale what is now Full Focus, a multimillion-dollar leadership training company. She’s had a front-row seat to how top entrepreneurs leverage assistants to maximize productivity and growth—and today, she’s pulling back the curtain to share those insights with us.In this episode, you’ll learn:✅ Why NOT hiring an EA is actually costing you more—and how it’s limiting your business growth.✅ How AI is transforming the role of executive assistants—and how to use it to streamline operations, boost productivity, and scale faster.✅ 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/227Tax 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.

In this discussion, Ben Reinberg, founder of a $500 million commercial real estate firm, shares his expert insights on building wealth through hard assets. He reveals the overlooked real estate asset class poised for significant opportunities in 2025. Ben recounts how he achieved a 3X return on investment and emphasizes leveraging relationships as a key strategy for success. Additionally, he highlights the power of passive investing and provides a blueprint from his book, illustrating how to thrive during economic challenges.

M.C. Laubscher, founder of Cashflow Ninja and author of "Get Wealthy for Sure," shares his expertise on alternative investments and financial freedom. He discusses why wealthy investors are shifting toward alternatives, revealing that family offices allocate up to 59% of their portfolios to these assets. Listeners learn essential strategies to shield wealth from inflation and taxes while navigating market volatility. M.C. emphasizes the importance of understanding different financial strategies, urging a fresh perspective on investing beyond traditional frameworks.

Bronson Hill, a former medical sales professional turned passive income investor, shares his incredible financial journey after interviewing over 2,500 millionaires. He reveals that building wealth begins with a mindset shift and the importance of surrounding oneself with successful people. Bronson discusses the hidden investment strategies the ultra-wealthy utilize, emphasizing alternative assets over traditional stocks. He also highlights common financial pitfalls and explains how to leverage inflation for financial independence.

Want to know where the smart money is going in 2025? Over $80 trillion is set to move from Baby Boomers to Millennials in the coming years, creating once-in-a-lifetime opportunities for those ready to capitalize. This week, the tables are turned—I’m the guest on Mike Koenigs’ podcast, Capability Amplifier, and we’re talking all about the biggest investment trends of 2025.We dive deep into overlooked opportunities like private credit, Web3 gaming, and the transformative potential of Bitcoin and AI. We also explore emerging trends such as border town real estate fueled by on-shoring, minority ownership in pro sports, and the untapped potential of distressed assets.I also share some of my biggest investing mistakes and how those experiences shaped the Lifestyle Investor philosophy that I teach today.If you're looking for high-value investment insights and a fresh perspective on wealth-building, this is an episode you don’t want to miss.In this episode, you’ll learn: ✅ The biggest investment opportunities for 2025—where smart money is going and how to capitalize on the largest wealth transfer in history.✅ How to spot “invisible deals”—and why the best investments aren’t found in the mainstream but through off-market opportunities few people know about.✅ Why Bitcoin, AI, and private credit are reshaping wealth creation—and how to position yourself ahead of the curve before the masses catch on.Show Notes: LifestyleInvestor.com/223Tax 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.

In this engaging discussion, Mike Koenigs, a serial entrepreneur and AI expert, unveils how entrepreneurs can harness AI to turbocharge their business growth. He shares innovative strategies for content creation, leveraging tools like Opus.pro for social media success. Mike also delves into AI's impact on brand development, including personalized music creation, and offers insights on redefining freedom through purpose over profit. His practical tips aim to empower listeners to integrate AI into their wealth-building strategies effectively.

Most entrepreneurs believe growth requires sacrificing everything else. Jonathan Goodman proves you can scale a business without giving up your freedom.He’s built multiple companies, written 12 books (including The Obvious Choice), and scaled coaching businesses to 7-figures—all while spending half the year living abroad with his family.How? By mastering the art of incentives, knowing when to not scale, and investing in cash-flowing assets that work harder than he does.In today’s episode, we break down the wealth-building strategies Jonathan used to scale a business to $35M+ in revenue.We explore why most investments fail to beat the returns generated by a well-run business, a leveraged personal brand, or an asymmetric bet like Bitcoin.Jonathan also shares how he structures his businesses to maximize freedom and avoid the common pitfalls of scaling.If you’re looking for a playbook on building wealth, designing a business that doesn’t take over your life, and making sure your money works for you—not the other way around—this episode has the answers.In this episode, you’ll learn:✅ Jonathan’s “whales and minnows” framework for eliminating 80% of your workload—why most entrepreneurs waste time on tasks that don’t move the needle, and how Jonathan ensures every hour works for him.✅ The “eight-four rule” of seasonal living—how Jonathan avoids burnout and stays at peak performance by alternating between intense work sprints and extended time off.✅ How to design scalable compensation systems that turn employees into partners—the secret to building a team that’s as invested in success as you are, without micromanaging.Show Notes: LifestyleInvestor.com/221Tax 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.

Ever feel like the tax system is stacked against you? In this episode, I’m talking with cost segregation expert Wes Mabry to uncover one of the most underutilized and powerful tax strategies available to real estate investors – a proven method to accelerate depreciation, defer taxes, and increase cash flow.Wes is the Founder of 1245 Consulting and one of the country’s leading authorities on cost segregation. For over 17 years, Wes and his team have helped investors—from small-time landlords to ultra-high-net-worth individuals—save over $2 billion in taxes.In our conversation, Wes breaks down cost segregation step-by-step: what it is, how it works, why it’s so powerful, and the types of properties that benefit the most. He shares insights on everything from accelerating depreciation on assets like flooring and gas lines to why car washes and mobile home parks offer some of the best opportunities.You’ll also learn about bonus depreciation, strategies to handle recapture taxes, and smart moves like retroactive studies and 1031 exchanges.In this episode, you’ll learn:✅ How cost segregation accelerates depreciation by breaking down property components like landscaping, gas lines, and specialized flooring—helping you offset income without cutting into cash flow.✅ Why asset classes like car washes and mobile home parks are tax goldmines, offering bigger savings than options like condos, self-storage or warehouses.✅ How retroactive cost segregation can help you reclaim missed tax benefits and significantly reduce your taxable income.Show Notes: LifestyleInvestor.com/220Tax 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.