The Lifestyle Investor - Investing, Passive Income, Wealth

Latest Episodes:

212: Failing His Way to a $100M+ After Quitting Wall Street with Jeremy Delk Nov 14, 2024

Show notes

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

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

211: How an 8-Figure Founder Hires World-Class Talent on a Budget with Kasim Aslam Nov 07, 2024

Show notes

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

Strategy Session

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

Connect with Justin Donald

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

210: Meet the M&A Expert Helping Entrepreneurs Exit for MILLIONS with Peter Worrell Oct 31, 2024

Show notes

“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

Strategy Session

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

Connect with Justin Donald

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

209: Why Most CPAs Are Failing You: Tax Strategies the Wealthy Use with Mark Kohler Oct 24, 2024

Show notes

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

Strategy Session

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

Connect with Justin Donald

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

208: What No One Tells You About Getting Rich with Erwin McManus Oct 17, 2024

Show notes

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

Strategy Session

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

Connect with Justin Donald

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

207: The Secret to Overcoming Adversity and Achieving Business Success with Carey Smolensky Oct 10, 2024

Show notes

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

Strategy Session

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

Connect with Justin Donald

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

206: How to Build Wealth Like the Top 1% with Dave Wolcott Oct 03, 2024

Show notes

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

Strategy Session

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

Connect with Justin Donald

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

205: How He Rebuilt His Life After Chasing Success with Isaac Stegman Sep 26, 2024

Show notes

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

Strategy Session

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

Connect with Justin Donald

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

204: Teach AI to Think Strategically & Scale Your Business with Geoff Woods Sep 19, 2024

Show notes

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

Strategy Session

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

Connect with Justin Donald

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

203: The Rise of Esports: A Lucrative Play for Investors with Marco Mereu Sep 12, 2024

Show notes

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

Strategy Session

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

Connect with Justin Donald

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

Our TOPPODCAST Picks

Follow Us

Stay Connected

The Lifestyle Investor – Investing, Passive Income, Wealth

Related Podcasts

Links

Stay Connected