The Lifestyle Investor - Investing, Passive Income, Wealth

Have you ever been told that maxing out your 401(k) and diversifying into stocks and bonds is the safest path to wealth?

Today, I’m speaking with Dave Wolcott—entrepreneur, investor, and founder of Pantheon Investments—who breaks down how the wealthiest people really invest. After following the traditional financial advice and feeling stuck, Dave realized there was a better way to build wealth through alternative investments. He has since dedicated his career to helping people unlock the playbook that the top 1% use to grow and preserve their wealth.

In our chat, Dave dives into his personal story of leaving corporate America, discovering financial freedom through alternative assets, and creating a strategy that combines mindset, relationships, and investments. He also shares how he’s passing these lessons on to his children and clients to help them preserve generational wealth.

In this episode, you’ll learn:

✅ How the wealthiest people invest—and why they only allocate a small percentage to the stock market.

✅ Tax-free passive income through smart asset repositioning and alternative real estate investments that outperform typical 401(k)s and Wall Street options.

✅ Dave’s 5 Phases of Holistic Wealth—a step-by-step strategy to build, protect, and multiply wealth while maintaining a balanced and fulfilling life. You'll discover how to shift from active income to massive passive income streams, allowing you to create financial freedom.

Free Gift

Get a digital copy of Dave's book, "The Holistic Wealth Strategy – A Framework for Building Legacy Wealth & Unlimited Freedom to Live an Extraordinary Life". Visit LifestyleInvestor.com/206

Show Notes: LifestyleInvestor.com/206

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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Have you ever felt like you're checking all the boxes of success, yet still feel empty inside?

Today, I’m speaking with Isaac Stegman—coach, entrepreneur, and intentional father—who shares how he completely redefined his life and business. Despite building a 7-figure company, Isaac felt trapped, disconnected, and stuck on autopilot. It wasn’t until he took a hard look at his life and made key shifts that he found true purpose and fulfillment.

In our chat, Isaac dives deep into the personal growth and mindset shifts that helped him break free from the relentless hustle. He shares how he learned to silence the urge to constantly push harder—often at the expense of his family and well-being. Now, Isaac has found a way to thrive in business without sacrificing the things that matter most.

In this episode, you’ll learn:

✅ Isaac’s four P’s: Perspective, Purpose, Principles, and Priorities, and how to use these to maintain clarity, direction, and fulfillment in both your personal and professional and life.

✅ Simple exercises to help you identify what's truly important, cut through the noise, and better manage your time and energy.

✅ How a single moment with his son completely changed Isaac’s understanding of what it means to prioritize family and relationships over business.

Free Gift

Get Isaac's Redefining Success Resource Guide & Workbook. Visit LifestyleInvestor.com/205

Show Notes: LifestyleInvestor.com/205

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.

Today, I’m excited to welcome Geoff Woods back on the podcast to talk all about how you can leverage AI to unlock new levels of growth in your business, outpace the competition, and get more done in less time. 

Last time we had Geoff on the show, he was the Vice President at The ONE Thing, where he coached and advised companies with annual revenues from $10 million to $60 billion. He has since left that role (a decision that wasn’t easy) but is now making big waves in the world of AI. 

He’s now the author of The AI-Driven Leader, host of The AI-Driven Leader Podcast and the Founder of AI Leadership, where he empowers leaders to harness AI, escape operational overwhelm, and think strategically to accelerate growth. 

In this episode, you’ll learn:

✅ Geoff’s incredible journey from exiting his role at The ONE Thing to becoming the Chief Growth Officer at Jindal Steel & Power, where he helped skyrocket the company's market cap from $750 million to over $12 billion in just four years.

✅ Why so many people fail to harness AI effectively, dismissing it as a waste of time – and Geoff’s proven system to make AI think strategically for you, delivering mind-blowing results for your business. 

✅ Real-world case studies showcasing AI's processing power – and how you can harness AI as a strategic partner to tackle your company’s biggest challenges and achieve unprecedented levels of success.

Free Gift

Get Geoff's AI-Driven Leader Crash Course. Visit LifestyleInvestor.com/204

Show Notes: LifestyleInvestor.com/204

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.

Esports is one of the fastest-growing industries today and it's paving the way for the next generation of entertainment and high-return investments. 

In fact, the Esports market was valued at $2.1 billion in 2023, and is expected to reach $7.5 billion by the end of 2030. 

That’s why I’m excited to be talking with today’s guest, Marco Mereu. Marco is the Founder and CEO of M80, a competitive gaming organization he established in 2022. Prior to this, he co-founded XSET in 2020 and served as its COO. His career in Esports also includes a role as Senior Vice President of Content Distribution at Super League Gaming and General Manager of Framerate, a company he founded and later sold. 

In this episode, you’ll learn:

✅ The story of how Marco left a stable career as a lawyer to build one of the most successful and popular esports brands in North America in under two years. His story is a testament to the power of following your passion and redefining success on your own terms.

✅ Investment opportunities in the booming Esports market, including sponsorships, media rights, digital goods, and more.

✅ How Esports is revolutionizing entertainment, turning gameplay into a dynamic, profitable investment frontier with millions of fans and untapped potential.

Free Gift

Get 50% off M80 merch and a one-page PDF that breaks down the esports industry. Visit LifestyleInvestor.com/203

Show Notes: LifestyleInvestor.com/203

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.

Today’s guest is Sean Kelly, an entrepreneur and founder and host of the Digital Social Hour, a podcast with 11 million followers. 

In our conversation, Sean takes us through his rise to becoming a millionaire by the age of 24. He gives us a behind-the-scenes look at how he struck gold during the NFT craze, including the jaw-dropping moment he pulled in $2.4 million in just 18 minutes on a single deal. 

But it’s not all smooth sailing. Sean opens up about the highs and lows of building wealth. He shares some hard-hitting stories about how the market crash in crypto nearly wiped him out and how that experience reshaped his approach to diversification, including the different asset classes he’s now focusing on to hedge his bets.

In this episode, you’ll learn:

✅ Sean’s story of earning $2.4 million in just 18 minutes during the NFT boom and selling his agency for $2.5 million at 60% profit margins. 

✅ The importance of knowing your financial freedom number – the amount of money you need to live comfortably without financial worry and how to use this crucial calculation to build the lifestyle you want.

✅ How the ultra-wealthy diversify their investments across different asset classes, like real estate, stocks, and crypto, to protect their wealth and weather market fluctuations.

Free Gift

Podcasting AMA with Sean. Visit LifestyleInvestor.com/202

Show Notes: LifestyleInvestor.com/202

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.

Today, I’m talking with Nicholas Kusmich. Nicholas is the founder of H2H Media Group, a consulting and META advertising agency which has generated over $600 million in revenue since 2007! 

Nic helps entrepreneurs predictably scale their revenue and time by easily getting more clients with marketing that doesn't suck. He’s known for delivering the highest returns on investment in the industry and is responsible for over 10 billion ad impressions and over 55 million leads. 

He works with A-List clients including the world’s most recognized thought leaders, New York Times best-selling authors, and the top Inc. 500 companies, creating advertising campaigns that actually convert.

In this episode, you’ll learn:

✅ How to eliminate your competition and dominate any industry by creating a “category of ONE” business.

✅ The "Contextual Congruence" process that combines direct response marketing with social behavior – and how to use it to transform your marketing efforts and dramatically boost ROI.

✅ The #1 reason most entrepreneurs fail to implement ideas – and a simple strategy Nic uses to take action and turn ideas into reality. 

Free Gift

Get a free copy of Nic's book Give: The Ultimate Guide To Using Facebook Advertising to Generate More Leads, More Clients, and Massive ROI. Visit LifestyleInvestor.com/201

Show Notes: LifestyleInvestor.com/201

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.

Today, I’m thrilled to be speaking with Will Duke, a successful entrepreneur turned investor and a valued member of the Lifestyle Investor Mastermind. Will shares his incredible journey from running two businesses to selling them for significant exits, all while transitioning into a successful investor. What makes his story unique is his thoughtful and patient approach to investing—focusing on building a solid foundation before diving into deals.

We explore the lessons Will learned from exiting his companies, his insights on how to approach private investments with caution, and the importance of continuous education. Will’s journey is a masterclass in how to strategically grow wealth through smart investing, while avoiding the common pitfalls that many fall into.

In this episode, you’ll learn:

✅ The exact vetting process Will uses to minimize risk and maximize returns, ensuring each investment aligns with his risk tolerance and long-term goals.

✅ Tax-optimization strategies that have saved Will millions during exits and investment deals. 

✅ How to determine whether your business is ripe for exit, structuring the exit for maximum profitability, and the often-overlooked challenges of transitioning from an entrepreneur to investor.

Show Notes: LifestyleInvestor.com/200

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.

Today, I’m excited to welcome Brad Weimert back on the show. In addition to being a long-time friend, Brad is an entrepreneur, real estate investor, adventurer, and the founder of Easy Pay Direct—the go-to merchant account provider for high volume eCommerce companies looking to accept credit cards safely and securely, without interruption. 

Brad also hosts the “Beyond A Million” podcast, where he interviews 7, 8, and 9-figure entrepreneurs to uncover the tactics and strategies behind their success.

In Brad’s first appearance on the podcast, we talked a lot about his entrepreneurial journey and scaling Easy Pay Direct. Today, we’re diving into real estate investing strategies and how Brad turned a recent real estate venture into a multimillion-dollar exit.

In this episode, you’ll learn:

✅ How Brad is “future-proofing” his real estate investments by leveraging new zoning laws and spotting early trends in the booming Austin market.

✅ The strategic advantage of owning your office space — and how Brad's unique approach to real estate can give you flexibility, leverage, and a significant return on investment.

✅ Find out how Brad leverages content marketing and turned the “Beyond a Million” podcast into a high-impact client acquisition tool for his business, Easy Pay Direct.

Show Notes: LifestyleInvestor.com/199

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.

Today’s episode is a little different. As many of you know, I’m a member of Front Row Dads – a group started by Jon Vroman, as a way to help men level up as husband’s and father’s. As a part of their podcast member takeover series, I was asked to interview a Dad of my choosing. I wanted to pick someone I admire and respect in both business and life, so I decided to interview my good friend, Brad Johnson. While this interview will be released on the Front Row Dads podcast, I couldn’t help but think our audience would appreciate listening to it as well. 

For context, Brad is the co-founder of Triad Partners, a business that partners with the top 1% of independent financial advisors, coaching them on how to achieve unlimited growth, freedom, and joy in business and life. Or as they have coined it, “Doing Business. Doing Life.” 

Brad and I first met years ago at a Front Row Dads event, and he’s been a great influence on me both personally and professionally ever since. In fact, he’s the reason this podcast exists. He’s the guy who talked me into starting The Lifestyle Investor podcast 5 years ago. 

In this episode, we both get pretty personal as we dive into our non-negotiable core values, practical tips for entrepreneurs chasing the mythical “work-life balance,” and the top lessons we’ve learned to successfully grow a business without sacrificing family, health, or happiness.

In today’s episode, you’ll learn:

✅ How to build a team that wants to do business and do life together – AND a culture that attracts great talent in the process! 

✅ Work-life balance is a myth – find out why work-life integration is the secret to making your business serve your life, not become your life.

✅ Brad’s #1 piece of advice to become a better spouse – and why you should do THIS as early as possible in your marriage to avoid falling into a doom loop.

Show Notes: LifestyleInvestor.com/198

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.

Today, I’m joined by Mark Podolsky, (a.k.a. The Land Geek.) Mark is the author of "Dirt Rich" and the founder of Frontier Properties – a highly successful land investing company. 

Since 2001, Mark has been a full-time land investor, completing over 6,000 land deals with an impressive average ROI of over 300% on cash flips and more than 1,000% on deals sold with financing terms.

Mark is passionate about helping others achieve financial freedom through land investing. He provides valuable insights and actionable strategies through his educational platform, "The Land Geek," where he teaches people how to buy and sell land effectively. His mission is to show that it’s possible to build significant wealth while maintaining a balanced, fulfilling life.

In this episode, you’ll learn:

✅ The story behind how Mark turned $3,000 (and zero real estate experience) into $90,000 by buying up raw land for pennies on the dollar and selling it online. This allowed him to quit his job and go all-in on land investing.  

✅ Mark’s step-by-step strategy for buying land at 25% of its value and selling it for massive profits, even with little upfront capital.

✅ The financing model that allows mark to make passive income – without the headaches. No renters, no rehabs, no renovations, no rodents!

Free Gift

Get a copy of Mark's book, Dirt Rich. Visit LifestyleInvestor.com/197

Show Notes: LifestyleInvestor.com/197

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

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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.