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/221

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

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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/220

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

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What if you could reclaim hours of your day just by getting digitally organized? In this episode, I’m talking with Shawn Lemon, Founder of The Digital Organizer, to uncover the systems and strategies that help entrepreneurs, executives, and busy professionals regain control of their digital lives.

From simplifying email management and file organization to choosing the right project management tools, Shawn reveals how a streamlined digital workspace can lead to less stress, more productivity, and a better quality of life. He shares insights from his time at Apple, lessons learned from working with top-tier clients (including his father-in-law, Michael Hyatt), and his approach to building systems that are easy to manage and scale.

Whether you’re drowning in emails, struggling to manage passwords, or just tired of wasting time searching for files, this episode is packed with actionable tips and resources to help you create order from chaos.

In this episode, you’ll learn:

✅ The exact tools Shawn recommends for email, password, and project management—and why some popular options should be avoided.

✅ How to eliminate the headache of juggling files across platforms like iCloud, Dropbox, and Google Drive by consolidating everything into one organized system—saving you time and stress.

✅ How a streamlined digital workspace can free up your time, reduce stress, and improve your productivity.

Free Gift

Get Shawn's File Organization Guide. Visit LifestyleInvestor.com/219

Show Notes: LifestyleInvestor.com/219

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

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Rate & Review

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Think your ideas aren’t worth protecting? Think again.

In this episode, I’m sitting down with Kary Oberbrunner—entrepreneur, bestselling author, and CEO of Instant IP™—to uncover why your Intellectual Property (IP) is your most valuable asset. Kary’s helped thousands of entrepreneurs safeguard their ideas and turn them into multiple streams of income using tools like blockchain and smart contracts.

His latest book, You Are an IP Company, is a wake-up call for anyone who wants to monetize their creativity, protect their business from competitors, and unlock hidden income streams.

Whether you’re a creator, entrepreneur, or investor, this conversation will change the way you think about what you’ve built—and why protecting it is essential for growth and success.

In this episode, you’ll learn:

✅ How some of the biggest brands in the world turn their Intellectual Property into their greatest competitive advantage

✅ Why your IP is your most valuable asset—and how failing to protect it could cost you everything.

✅ Why it’s never been easier (or more affordable) to protect your ideas.

Free Gift

Get 10% off Kary's Instant IP™ program. As a bonus, you'll also get access to his course, You Are an IP Company, which is valued at over $2,000. Visit LifestyleInvestor.com/218

Show Notes: LifestyleInvestor.com/218

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

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Did you know less than 1% of companies are publicly traded? While most investors obsess over stocks, the ultra-wealthy are quietly building fortunes in the other 99%. Today, we’re unlocking their playbook.

In this episode, I’m talking with Christopher Zook, Founder of CAZ Investments and co-author of “The Holy Grail of Investing,” which he co-authored with Tony Robbins, to explore how the wealthiest individuals invest differently. From private equity and real estate to professional sports ownership, Christopher reveals the strategies they use to create cash flow, reduce risk, and build lasting wealth.

We break down why private markets consistently outperform public markets, the power of true diversification beyond stocks and bonds, and how to align your investments for maximum upside with minimal risk. Plus, Christopher shares game-changing insights into new legislation that could make these opportunities accessible to more investors than ever.

If you’re ready to rethink your approach to investing, this episode is packed with actionable insights.

In this episode, you’ll learn:

✅ How new rules around accredited investors are opening up private markets to more people, including the ability to invest 401(k) and 403(b) plans in private opportunities.

✅ Why GP Stakes are one of the hottest private equity trends of the past decade, how he became a first mover in the space, and why this investment offers a stronger risk-reward balance and reliable cash flow.

✅ How big family offices and high-net-worth investors think about capital allocation, risk management, and building generational wealth away from the volatility of public markets.

✅ How Christopher is entering the rapidly expanding world of sports investments, why it’s poised for massive growth, and what it means for investors looking to capitalize on this emerging trend. 

Free Gift

 Get Christopher's report, "GP Stakes: A New Path to Private Equity." Visit LifestyleInvestor.com/217

Show Notes: LifestyleInvestor.com/217

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

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Ever wonder how the wealthiest families invest their money? Spoiler alert: It’s nothing like the 60/40 stock-to-bond strategy you’ve been told to follow.

In this episode, Scott Ford pulls back the curtain on how the rich strategically grow and protect their wealth, revealing why 45%-59% of their portfolios are allocated to alternative investments.

Not only is Scott a Lifestyle Investor Mastermind member, but he’s also the founder of The Way2Wealth, a holistic financial framework that empowers you to protect, grow, and enjoy your wealth. With 30+ years in wealth management, Scott has mastered the art of creating sustainable strategies that work for everyday investors and the ultra-wealthy alike.

His mission is to spread education about finances and give people the tools that they need to reach financial independence through financial wisdom.

In this episode, Scott shares how the 1% approach wealth differently and how you can apply those same principles to achieve financial freedom for yourself.

In this episode, you’ll learn:

✅ Scott’s "All Season Investing" strategy: A simple, actionable framework for navigating market cycles and achieving long-term growth.

✅ The infinite banking concept – and how to use it as a strategic tool to store wealth, maintain liquidity, and fund future opportunities.

✅ The 2 most important questions you should ask financial advisors before trusting them with your money—and how to avoid common pitfalls in the industry.

Free Gift

 Get Scott's All Seasons Investing whitepaper. Visit LifestyleInvestor.com/216

Show Notes: LifestyleInvestor.com/216

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

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Rate & Review

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What do you do when the dream life you’ve worked so hard for starts to feel empty? Christian Ray Flores went from global stardom as a musician to rediscovering purpose through service, family, and faith. His journey isn’t just inspiring—it’s a roadmap for anyone chasing a life that truly matters.

Christian was living the dream—millions of fans, sold-out arenas, and chart-topping hits. But behind the glitz, he felt a void that success couldn’t fill. In this episode, Christian shares how he walked away from fame to pursue a more meaningful life. He takes us through his journey of redefining success, investing in holistic growth, and using his experiences to coach high achievers around the world.

Whether you're an entrepreneur, investor, or simply seeking a life of greater impact, Christian’s story will challenge and inspire you to live life on your terms.

In this episode, you’ll learn:

✅ How Christian became one of Russia’s biggest pop stars—and why he walked away.

✅ Why so many high achievers feel unfulfilled—and how to break free.

✅ Life-changing lessons from coaching Olympic athletes, entrepreneurs, fashion designers, artists, and Russian mafia members.

Free Gift

 Get free access to the Xponential Life Scorecard, visit LifestyleInvestor.com/214

Show Notes: LifestyleInvestor.com/214

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

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This week’s episode is deeply special to me and many of you who knew or were impacted by the late John Ruhlin. John was not just a master at his craft—he was a master at life, relationships, and giving. His unexpected passing has left a void in the hearts of those who knew him, but his legacy lives on through the countless lives he touched and his revolutionary work in the art of gift giving.

This conversation originally aired in May 2021 and remains one of the most important episodes I’ve ever recorded. John was one of my closest friends—someone I’ve known since we were 18 years old. Over decades of friendship, he continually lifted me up, connected me with incredible people, and exemplified what it means to lead with a giving heart. His company, Giftology, has transformed businesses and relationships alike, and his book has become a must-read for anyone looking to make a lasting impact.

In this tribute episode, you’ll hear John’s heart, his wisdom, and his genuine perspective on life and relationships. You’ll laugh with us, reflect on his insights, and hopefully feel inspired to carry forward his legacy of giving. John’s business partner and close friend, Rod, has pledged to continue running Giftology for the next 18 years to support John’s wife, Lindsey, and their four beautiful daughters, Reagan, Blakeley, Saylor, and Layton.

If you feel moved to honor John’s legacy, consider exploring the incredible work his team continues to do at giftologygroup.com. Supporting their work not only carries forward John’s mission but directly supports his family. For more details, you can visit giftologygroup.com/rwa.

Thank you for listening to this heartfelt tribute. John was truly one of a kind, and I’m honored to share his story, his message, and his legacy with you.

PLEASE SUPPORT JOHN'S FAMILY

Honor John’s legacy and support his family by making a donation. Every little amount helps and will go directly towards taking care of his wife Lindsay, and their four daughters (Reagan, Blakely, Saylor, & Layton – age 4 to 14). CLICK HERE to make a donation.

REFERRALS WITHOUT ASKING

John’s mission was to bring greater generosity to the world while lifting up coachable business leaders to places they never thought possible. Whether you’re an executive of a Fortune 100 company, an owner, a startup, or a solo-professional conquering your industry – GIFT∙OLOGY changes relationships forever. And relationships take you places that traditional marketing can’t. So, if you want to honor john and his work, a great place to start is by checking out Referrals Without Asking – a free resource that will allow you to turn your contacts into endless referral partners. CLICK HERE to get the guide.

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

Imagine knowing in your 20s what you know now—how much further ahead would you be? That’s exactly what today’s guests, Nick and Molly Pastermack, are helping ambitious investors under 35 achieve.

Nick and Molly are serial entrepreneurs, mentors, and leaders of the Lifestyle Investor Foundations Mastermind—a group we started to equip young adults with the tools, strategies, and connections they need to fast-track their success.

From humble beginnings as college cheerleaders to building over two dozen businesses, their story is one of grit, growth, and unwavering vision. They’ve navigated industries from real estate to wellness, all while raising two incredible children and mentoring hundreds of aspiring leaders. Their mission? To equip young professionals with the skills that truly matter—financial freedom, optimal health, emotional intelligence, and business growth.

If you’re a parent, this episode provides an inspiring look at what’s possible for the next generation. Nick and Molly are creating a ripple effect for families who want to see their children thrive—helping young people make smarter choices, achieve financial independence, and lead meaningful lives.

In this episode, you’ll learn:

✅ How Nick and Molly Pastermack turned early failures into stepping stones for building over two dozen businesses across diverse industries—and the lessons they want young professionals to take away.

✅ The 4 pillars of success they teach in the Lifestyle Investor Foundations Mastermind—financial freedom, optimal health, emotional intelligence, and business growth—and why these areas are crucial for achieving lasting success.

✅ Actionable strategies parents can use to empower their children to think bigger, act boldly, and make smarter financial decisions, even if they’re just starting their wealth-building journey.

Free Gift

 To get the The Lifestyle Investor Foundations Live Event video replay, visit https://lifestyleinvestor.com/foundations

Show Notes: LifestyleInvestor.com/213

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

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

What does it take to rebound from crushing losses, build multiple successful companies, and turn setbacks into strategic investments? 

In today’s episode, I sit down with Jeremy Delk, founder of Delk Enterprises, who has mastered the art of “failing forward” to build a diverse portfolio of profitable ventures.

Starting as a Wall Street trader who earned and lost millions by age 20, Jeremy’s journey is nothing short of extraordinary. He shares his path from trading chaos to strategic exits, including the highs and lows of investing in early-stage companies, the lessons learned from losing big on a Ponzi scheme, and how global travel opened his perspective on business and life.

In this episode, you’ll learn:

✅ Jeremy’s incredible story of making millions at 19, losing it all in four days, and building a powerhouse VC fund across multiple industries.

✅ Strategies for building teams and systems that allow you to lead without micromanaging. 

✅ Jeremy’s tips for exiting at the perfect time, what makes a company worth betting on, and how to avoid the common traps that catch many entrepreneurs when they try to shift from founder to investor.

Free Gift

Get The 10 Commandments of a Lifestyle Investor. Visit LifestyleInvestor.com/212

Show Notes: LifestyleInvestor.com/212

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.

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