Episodes
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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
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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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What 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.
Connect with Justin Donald
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Episodes manquant?
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What if hiring top talent for your business was easier than you thought?
Today, I'm talking with my friend and Lifestyle Investor Alum Kasim Aslam, who, after selling his Google Ads agency for 8-figures, set his sights on a new mission: helping entrepreneurs scale by connecting them with top-tier executive assistants from emerging markets.
In this episode, he reveals how tapping into international talent has transformed his business—and how it can transform yours, too.
He breaks down the process of hiring from countries like Argentina and Colombia, where executive assistants can offer more than just admin support—they can become the backbone of your operations.
In This Episode You’ll Learn:
✅ The Talent Advantage: Why Kasim believes top executive assistants from emerging markets are the secret weapon for small businesses looking to scale sustainably.
✅ Beyond Outsourcing: Kasim’s unique approach to finding and developing team members who don’t just assist but become critical assets to your business.
✅ Building Your Talent Pipeline: How to create a hiring system that’s designed to grow your business and free up your time—all while making a global impact.
Free Gift
To get access to Kasim's full Delegation Library for Entrepreneurs, which includes 80+ task ideas you can delegate to your assistant today! Visit LifestyleInvestor.com/211
Show Notes: LifestyleInvestor.com/211
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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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“We're going to ask the investor community to prove that they deserve the opportunity to invest in your beautiful business.”
That’s a quote from today’s guest, Peter Worrell—a mergers & acquisition expert with over 4 decades of experience helping entrepreneur owner-managers achieve successful capital gain events by maximizing the enterprise value of their businesses.
Pete’s here today to address one of the biggest challenges that entrepreneurs face...
How can you maximize the value of your business and secure the best possible exit?
Most entrepreneurs rush into selling and leave millions on the table—without even realizing it. But Pete's approach has helped countless entrepreneurs sell their companies for life-changing wealth—often far beyond what they ever dreamed possible.
00:00 Intro
02:00 Why Boosting Enterprise Value is Essential for Every Entrepreneur
05:23 The Right Time to Tell Your Team You’re Selling Your Business
07:45 The Best Time to Start Preparing Your Business for Exit
08:50 How to Make Investors Compete for a Stake in Your Business
10:25 How to Level the Playing Field in Investor Negotiations
13:00 Choosing the Right Advisors to Maximize Your Business Value
18:26 Why High Margins, Not Just Revenue, Attract Top Investors
24:14 Why Your Company’s Future Vision Drives Higher Valuation
30:45 Attracting the Right Fit Investors—Not Just Any Buyer
34:00 Take Investor Calls on Your Terms, Not Theirs
37:02 The Enterprise Value Book
Free Gift
To get a free copy of Peter's book, Enterprise Value: How the Best Owner-Managers Build Their Fortune, Capture Their Company's Gains, and Create Their Legacy, visit LifestyleInvestor.com/210
Show Notes: LifestyleInvestor.com/210
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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Most people see the tax code as a maze of restrictions, but what if it’s actually a roadmap to wealth?
Today’s guest, Mark Kohler, known as “America’s #1 Small Business Tax Lawyer” reveals how the tax code is packed with hidden opportunities, waiting to be uncovered—if you know where to dig.
While most CPAs are simply filing forms, Mark shows you how proactive tax strategy can turn the government into your wealth-building partner. If you’re tired of missing out on hidden tax opportunities, this conversation will give you a whole new perspective on how to maximize your wealth.
In this episode, you’ll learn:
✅ The overlooked tax-saving strategies that can free up thousands to reinvest—and why the IRS isn’t out to get you. In fact, they can actually be your ally in building wealth.
✅ Why most CPAs aren’t strategizing for you — and how to find one who will.
✅ Why Mark loves to invest in short-term rentals and industrial properties as his go-tos for cash flow and tax benefits – and how he’s using real estate profits to diversify into alt assets like crypto.
Free Gift
Get Justin's special report, 24 Questions to Ask When Vetting a CPA. Visit LifestyleInvestor.com/209
Show Notes: LifestyleInvestor.com/209
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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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We all chase success. But sometimes, even after achieving everything we set out to, something feels off. I’ve seen it happen time and again: high-achieving entrepreneurs who look around one day and think, Is this all there is?
Today’s guest, Erwin McManus, knows exactly how that story goes. Erwin is the founder and lead pastor of Mosaic, an artist, and author with over one million book sales who’s worked with everyone from the NFL and the Pentagon, helping them perform at the highest level while living a balanced life.
In our conversation, Erwin shares what these elite performers do to rise to the top. But more importantly, he talks about why so many still end up miserable and trapped despite their achievements. And he’s sharing his best advice to help you avoid that trap.
Plus, he gives a sneak peek into his latest book, Seven Frequencies of Communication, where he breaks down how to become a world-class communicator who leads with influence and intention.
In this episode, you’ll learn:
✅ How Erwin transformed his life from struggling to afford college and living below the poverty line to becoming an internationally renowned speaker and consultant for powerhouse organizations like the NFL and the Pentagon.
✅ The habits, mental frameworks, and decision-making strategies that separate the top 1% from everyone else, and how you can apply them to your life and business.
✅ Strategies for creating wealth while staying true to your values and purpose and building a life that’s financially rewarding but also deeply fulfilling.
Free Gift
Get Erwin's The Communicator's Tool Kit. Visit LifestyleInvestor.com/208
Show Notes: LifestyleInvestor.com/208
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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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In this episode, I’m talking with my good friend, Carey Smolensky – an entrepreneur, event producer, musician, author, and someone who truly lives life on his terms. Carey has spent over four decades building a boutique production company, and has worked with high-profile clients like Cutco and Tony Robbins Platinum Partners. What’s incredible about Carey is how he’s navigated challenges, both personal and professional, while continuing to thrive.
When COVID shut down his entire industry for 15 months, Carey pivoted, launching a new business that not only survived but flourished. He took that adversity and turned it into the best financial year his company had ever seen. In our conversation, Carey shares how he did it, and what lessons you can apply to your own life and business.
Carey also talks about the importance of family, building meaningful relationships, and living a life of passion and purpose.
Whether it’s diving with bull sharks or producing global events, Carey’s zest for life will inspire you to live more fully and take action toward your own financial freedom.
In this episode, you’ll learn:
✅ How Carey pivoted his business during the pandemic and built a new income stream that led to his best financial year yet.
✅ The key to building long-term client relationships, and why Carey treats every client like a VIP.
✅ How Carey balances his high-energy work life with family time and why it’s important to “do life” with the right people.
Free Gift
Get Carey's blueprint for Finding Your Passion. Visit LifestyleInvestor.com/207
Show Notes: LifestyleInvestor.com/207
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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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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
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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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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.
Connect with Justin Donald
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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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.
Connect with Justin Donald
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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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.
Connect with Justin Donald
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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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.
Connect with Justin Donald
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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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
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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.
Connect with Justin Donald
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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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.
Connect with Justin Donald
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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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.
Connect with Justin Donald
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Today, I’m excited to be talking with Anne Beiler. Anne is the Founder of Auntie Anne’s, the world’s largest hand-rolled soft pretzel franchise (which she sold in 2005).
During today’s conversation, Anne shares her personal story and opens up about the series of tragic life events that left her broken, traumatized, and in a deep depression. Leaning on faith and family, she channeled that devastating pain into a bigger purpose that led to the birth of Auntie Anne’s, which she grew from a single stand into a beloved international franchise with 900+ locations.
You’ll also hear how Anne dealt with identity-crisis after selling Auntie Anne’s in 2005. A testament to her creativity and resilience, she shifted her focus to inspiring others. She now helps people face their demons and become a force for good in their businesses and communities through her speaking, books, and personal development courses.
In today’s episode, you’ll learn:
✅ Anne’s journey of growing Auntie Anne’s from a single soft-pretzel market stand into an international franchise with stores in all 50 US states.
✅ The mindset that helped Anne to overcome devastating pain and trauma, and turn them into foundations for honesty, love, kindness, and a life of service.
✅ Auntie Anne’s formula of three P’s (Purpose, Product, People) for success that any brand or franchise can use to grow their business.
Free Gift
Get a digital copy of Anne's book, Overcome and Lead. Visit LifestyleInvestor.com/196
Show Notes: LifestyleInvestor.com/196
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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Adam Jason is a Partner at Legacy Group, an investment firm in Latin America focusing on top-tier businesses and high-net-worth accredited investors seeking exceptional returns. Adam has a background in advising Fortune 500 companies and investment banks and has represented them in public and private offerings exceeding $10 billion.
In our conversation, you’ll hear Adam’s remarkable journey from Big Law to scaling Green Coffee Company to become the #1 coffee producer in Colombia’s fiercely competitive market. What’s truly remarkable is they have embraced eco-friendly practices and prioritized worker welfare in an industry where this is far from typical. This not only fueled their growth but also helped them create an appealing story that resonates with coffee lovers worldwide.
Adam shares the strategies behind developing and scaling the Green Coffee Company brand, which has successfully competed against giants like Starbucks and Nestle. Plus, you’ll learn how he leverages coffee and agriculture to diversify income through coffee byproducts.
In today’s episode, you’ll learn:
✅ How Green Coffee Company became the largest coffee producer in Colombia with 400 full-time and 2500 part-time workers, and the strategies that allowed them to be profitable for three years straight and attract $80 million in investments.
✅ Why the wealthiest are putting part of their portfolios into agriculture, a sector that offers opportunities for diversification and, in some cases, outperforms real estate.
✅ How Adam and GCC are shaking up the coffee industry in Colombia by setting new standards for worker rights, challenging giants like Starbucks with eco-friendly practices, and creating a compelling brand story that resonates with coffee lovers everywhere.
Free Gift
Get Access to Discount Codes for GCC's First Juan Valdez Coffee. Visit LifestyleInvestor.com/195
Show Notes: LifestyleInvestor.com/195
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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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Kip Sowden is the CEO and Chairman of RREAF Holdings who has over 37 years of experience in commercial real estate. Kip has been involved in the financing of over $8 billion in commercial real estate loans and has brokered the sale of over $10 billion in commercial real estate transactions.
He has also acquired, developed, and renovated over 5 billion in commercial real estate including retail, office, multi-family, and hospitality throughout the Southwestern and the Southeastern United States. During our conversation, Kip shares the strategic thinking behind RREAF Holdings' approach, which focuses on delivering substantial value to investors while minimizing their risk exposure.
We discuss why RREAF specifically targets middle America, a strategy that has proven beneficial in tapping into markets with high growth potential yet often overlooked by major players. Kip also highlights their favorite US markets for building and how RREAF’s commitment to vertical integration has significantly boosted the efficiency of their operations.
In this episode, you’ll learn:
✅ How RREAF's focus on challenging development projects and commercial acquisitions has revolutionized the real estate landscape and boosted their assets from $100 million to $4.5 billion.
✅ RREAF's unique approach that allows retail equity investors to participate in temporary sponsor loans to different LLCs, yielding returns over 12% and providing unparalleled value for both investors and institutional partners.
✅ Kip's favorite markets for investment and why RREAF targets middle America for residential, leisure, and vacation properties.
Free Gift
Get Kip's free 2024 Market Overview Report. Visit LifestyleInvestor.com/194
Show Notes: LifestyleInvestor.com/194
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
FacebookYouTubeInstagramLinkedInTwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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