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The Lifestyle Investor – Investing, Passive Income, Wealth

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

Copyright: © © 2022 Justin Donald

Latest Episodes:

232: Whole Life Insurance: The Secret Wealth Strategy of the Rich with Caleb Guilliams Apr 03, 2025

Show notes

Whole Life Insurance is widely misunderstood, yet for billionaires and family offices, it’s 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 foundation—one 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 Insurance—and 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, You’ll Learn:

1.) Why Whole Life Insurance isn’t an investment—and how the wealthy use it to build lasting financial security.

2.) The truth about Whole Life Insurance—the key benefits, hidden pitfalls, and the biggest misconceptions that trip people up.

3.) The costly mistakes people make when setting up a Whole Life policy—and 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 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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

231: From NFL to Financial Freedom: How Devon Kennard Built an 8-Figure Real Estate Portfolio Mar 27, 2025

Show notes

Most pro athletes go broke after retiring. Devon Kennard isn’t 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 portfolio—all 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, you’ll 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 NFL—including the red flags to look for when vetting deals.

3.) How Devon escaped the W-2 paycheck cycle and built passive income while still working—and 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 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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

230: From Entrepreneur to Investor – How to Build & Manage Wealth After an Exit with Dr. Tony Jacob Mar 20, 2025

Show notes

So you’ve sold your business—what’s 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 today’s episode, I’m sitting down with Dr. Tony Jacob—an 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.

We’re 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 you’re an entrepreneur preparing for an exit—or you’ve already sold and want to make smarter financial decisions—this episode is a must-listen.

In this episode, you’ll learn:

The biggest investing mistakes post-exit entrepreneurs make—and how to avoid them.

Why capital preservation is just as important as wealth creation—and 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 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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

229: Why the Wealthy Are Betting Big on Private Credit with Peter Sack Mar 13, 2025

Show notes

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/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 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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

228: M&A Expert Teaches You to Sell Your Business for Maximum Value with Chad Morissette Mar 06, 2025

Show notes

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/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 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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

227: The CEO’s Secret Weapon: How an EA Can Help You Buy Back Time & Scale Faster with Tricia Sciortino Feb 27, 2025

Show notes

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/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 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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

226: The Wealth Formula Hard Assets, Leverage & Passive Investing with Ben Reinberg Feb 20, 2025

Show notes

If you want to build long-term wealth and protect your money from market volatility, today’s 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, you’ll learn:

✅ The one real estate asset class that will have the biggest opportunities in 2025—and why most investors are overlooking it.

✅ How Ben turned a single deal into a 3X return—and the investing strategy he still swears by today.

✅ The 3 most powerful wealth levers you can use to scale your investments faster—with 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 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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

225: Build Wealth & Beat Inflation: Cashflow Ninja’s Alternative Investing Playbook with M.C. Laubscher Feb 13, 2025

Show notes

Are you stuck in the Wall Street mindset and looking for better ways to grow and protect your wealth?

In this episode, I’m 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 you’re 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, you’ll learn:

✅ Why family offices allocate up to 59% of their portfolios to alternative investments

✅ How to navigate inflation, market volatility, and tax threats with defensive strategies

✅ The power of inefficient markets and the asymmetric opportunities they offer

✅ How to create a “sleep-well-at-night” 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 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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

224: Unlock The Millionaire Mindset & Invest Like the Rich with Bronson Hill Feb 06, 2025

Show notes

Building wealth isn’t just about what you do—it’s about how you think. And the ultra-wealthy know that financial success starts in the mind.

That’s exactly what today’s 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, you’ll learn:

✅ The mindset shift that helped Bronson 20X his net worth—and the surprising reason most people stay broke.

✅ How 2,500 millionaires built their wealth—and the biggest investing mistakes to avoid.

✅ The investment strategy ultra-wealthy investors use to outperform the stock market.

✅ The hidden “Wealth-Worthiness” 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 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

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

223: The Biggest Investment Trends of 2025 (My Interview on Capability Amplifier) Jan 30, 2025

Show notes

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/223

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

See 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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