The Lifestyle Investor - Investing, Passive Income, Wealth

One conversation can change the trajectory of your life. Whether you're building a business, growing your wealth, or navigating a major life transition, the people you surround yourself with often determine the opportunities available to you and the outcomes you create.

That's why I'm excited to welcome Chip Paucek to the podcast. Chip is a serial entrepreneur, co-founder and CEO of Pro Athlete Community (PAC), one of the world's largest private membership organizations for professional athletes. PAC was founded on the belief that professional sports should be a first chapter rather than a final destination, and provides athletes with the resources, community and relationships they need to thrive in business, leadership, investing, and life after the game. 

After building 2U from a startup into one of the largest online education companies in the world, which approached $1 billion in revenue, Chip set out to help athletes successfully navigate life after sports by creating a community focused on leadership, relationships, business growth, and personal development.

In our conversation, Chip shares the mission behind Pro Athlete Community, the challenges many athletes face after retiring from sports, and the systems they've created to connect athletes with world-class entrepreneurs, investors, and mentors.

In this episode, you’ll learn: 

✅ How one meaningful relationship can completely change the trajectory of your life and career. 

✅ How elite athletes apply grit, discipline, and resilience to succeed long after their playing careers end.

✅ The importance of trust, authenticity, and continuous learning as essential building blocks to create long-term success and fulfillment.

Show Notes: LifestyleInvestor.com/299

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.

LIL #007: Every Deal You See Has Already Been Rejected

The best private investments close before you ever hear about them. Here's why - and what to do about it.

Episode Summary

In this episode of The Lifestyle Investor Podcast, host Justin Donald breaks down why the best private deals never reach the open market - and what it really means when one does.

You'll learn why open-market deals are a warning sign, how advisors' hidden incentives shape the deals you see, and how to start building the kind of access that leads to truly invisible deal flow.

Question of the Day 🗣️

Where are you currently sourcing your investment opportunities - through an advisor, online platforms, a network, or somewhere else? Drop it in the comments. No wrong answers - just curious where everyone's starting from.

Key Take-aways

• The best private deals fill inside trusted networks before they're ever announced
• If a deal made it to the open market, ask why the insiders passed on it
• Your advisor's deal recommendations may be driven by commissions, not quality
• Access to deal flow is necessary but not sufficient - private doesn't mean good
• You make your money on the buy side by saying no to 90% of what you see

Timestamped Outline ⏱️

00:00 - Introduction and recap of the three shifts

00:35 - The best deals are invisible, and that's by design

01:20 - The uncomfortable truth about open market deals

01:49 - The hidden conflict in your advisor's deal flow

02:52 - What invisible deals actually are

03:27 - Mobile home parks and SFR before they were mainstream

04:02 - The real access problem: deals reserved for insiders

04:52 - Finding deals is about saying no to 90%

05:27 - Five bad deals pitched in one week

06:00 - Next week: the five filters for evaluating any deal

Links & Resources 🔗

• The Lifestyle Investor Lens (weekly newsletter) → https://lifestyleinvestor.com/newsletter

Connect & CTA 🎯

👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.

🎁 Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today. Subscribe so you don't miss the next issue: https://lifestyleinvestor.com/newsletter

Credits

Host: Justin Donald © 2026 Lifestyle Investor. All rights reserved.

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

Change is unavoidable, but how you respond to it can have a huge impact on the trajectory of your life. Whether you're navigating a career transition, facing rejection, or pursuing an ambitious goal, uncertainty often reveals who you become under pressure.

That's why I'm excited to welcome Justin Forsett to the podcast. Justin had a nine year career in the NFL and played for seven different teams before eventually breaking through as a Pro Bowl running back.

After football, he successfully transitioned into entrepreneurship as the founder and CEO of Hustle Clean, a fast-growing personal care brand now sold in major retailers across the country. He’s also developed into an amazing public speaker and mentor, teaching organizations and leaders about resilience, leadership, and overcoming adversity.

In our conversation, Justin shares the lessons he learned from being cut seven times, how he handled criticism and negative thoughts in his career, and what it takes to lead a business through uncertainty while staying true to his purpose.

In this episode, you’ll learn: 

✅ How Justin turned years of setbacks and uncertainty into a breakthrough NFL career and built a highly successful business.

✅ Why mental toughness, resilience, and adaptability are critical for both athletes and entrepreneurs.

✅ How to create a life in alignment with your faith, family, business, and long-term purpose.

Show Notes: LifestyleInvestor.com/298

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

• Facebook
• YouTube
• Instagram
• LinkedIn
• Twitter

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

LIL #006: I Had Financial Freedom Before I Was a Millionaire

The size of the pile was never the point - here's what actually matters.

Episode Summary

In this episode of The Lifestyle Investor Podcast, host Justin Donald breaks down why cash flow - not net worth - is the real path to financial freedom. You'll learn the three numbers that actually determine your freedom, why your net worth is probably half what you think, and how mobile home parks built his family's financial foundation one park at a time.

Question of the Day

Do you know your survival number and your lifestyle number? If you've calculated them, drop them in the comments (or just share which one surprised you more). If you haven't - that's your homework this week.

Key Take-aways

• Financial freedom doesn't require millionaire status - it requires cash flow
• Know your three numbers: survival, lifestyle, and freedom
• Your net worth is likely inflated by unrealistic business valuations and ignored taxes
• The "accumulate and deplete" model is built on hope, not certainty
• Surplus income changes compounding math from 15-20% savings to 100%

Timestamped Outline

00:00 - Introduction - the third shift reshaping wealth

00:22 - The shift from net worth to cash flow

00:39 - Financial freedom before millionaire status

01:22 - Why net worth is the wrong target

01:35 - How most people inflate their net worth

02:02 - Taxes and lost write-offs after selling

02:37 - The accumulate-then-deplete model

03:23 - Your survival number and lifestyle number

04:01 - The Freedom Number explained

04:12 - Mobile home parks - from first park to surplus income

04:53 - Why surplus income changes everything

05:30 - From Netflix subscription to $1M in passive income

06:17 - Better business decisions through financial freedom

07:15 - Stop chasing net worth, start chasing cash flow

08:04 - What's coming next - finding deals that cash flow

Links & Resources

• Subscribe to The Lifestyle Investor Lens → https://lifestyleinvestor.com/newsletter

Connect & CTA

👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.

🎁 Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today. Subscribe so you don't miss the next issue: https://lifestyleinvestor.com/newsletter

Credits

Host: Justin Donald © 2026 Lifestyle Investor. All rights reserved.

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

Professional athletes earn more money than most people will see in a lifetime, but their wealth can vanish surprisingly fast without the right guidance, relationships, and mindset. Whether you're a professional athlete, entrepreneur, or investor, building wealth requires far more than simply earning a high income or a big payday.

That's why I'm excited to welcome Devin McCourty to the podcast. Devin was a 1st round pick who spent 13 seasons with the New England Patriots and won three Super Bowls during one of the greatest dynasties in NFL history. Since retiring from football, Devin has transitioned into broadcasting on NBC's Football Night in America, the #1 primetime show on television for the past 15 consecutive years.

Devin is also a student and speaker at PAC (Pro Athlete Community), where he provides mentorship and helps athletes make smarter financial decisions and prepare for the next chapter in their lives.

In this conversation, Devin shares tough money lessons from navigating a career in the NFL and the importance of surrounding yourself with trusted advisors. We discussed the leadership principles that helped him succeed both on and off the field, including parenting, youth sports, and how competition can help build resilience that lasts far beyond the game.

In this episode, you’ll learn: 

✅ The pressure that NFL athletes face after signing their first contract, and the myths about how much is spent frivolously. 

✅ How athletes and entrepreneurs can avoid costly investing mistakes by building the right team around them.

✅ Why failure, competition, and adversity are some of life's greatest teachers both in sports and business.

Show Notes: LifestyleInvestor.com/297

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

• Facebook
• YouTube
• Instagram
• LinkedIn
• Twitter

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

LIL #005: Your Advisor Collects Fees Whether You Win or Lose

Your advisor gets paid every year. Less than 5% of them actually earn it.

Episode Summary

In this episode of The Lifestyle Investor Podcast, host Justin Donald breaks down why the traditional financial advisor model is broken and what the ultra-wealthy use instead.

You'll learn why AUM fees create a structural conflict of interest, how a real family office works compared to a single advisor, and how $30,000 in annual tax savings can compound to over $13 million across 30 years.

Question of the Day 🗣️

What's the biggest challenge you're facing right now when it comes to your tax strategy or finding the right financial team? Drop it in the comments.

Key Take-aways

• Less than 5% of money managers outperform a basic index fund over 15 years
• The AUM fee model pays your advisor whether they win or lose for you
• A family office coordinates specialists across tax, legal, estate, and deal flow
• The gap between a CPA who files taxes and one who minimizes them is massive
• $30K in annual tax savings compounds to $13M+ over 30 years

Timestamped Outline ⏱️

00:00 - Introduction and recap of shift one

00:13 - Shift two: from investment advisor to family office

00:44 - How your advisor actually gets paid

01:06 - The structural conflict of interest in AUM fees

01:31 - Less than 5% of managers beat the S&P 500

02:36 - What a family office actually is

03:42 - Why it costs $4M-$14M per year to run one

04:07 - Tax strategy: compliance vs. minimization

04:48 - The CPA litmus test

05:34 - How $30K in tax savings becomes $13 million

06:10 - Accessing the family office model without being a billionaire

07:44 - Next week: the third shift

Links & Resources 🔗

• The Lifestyle Investor Lens (weekly newsletter) → https://lifestyleinvestor.com/newsletter

Connect & CTA 🎯

👉 Enjoyed this? Subscribe & leave a review on Apple Podcasts.

🎁 Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today. Subscribe so you don't miss the next issue: https://lifestyleinvestor.com/newsletter

Credits

Host: Justin Donald © 2026 Lifestyle Investor. All rights reserved.

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

Success has an interesting way of moving the goalposts. You land a book deal, the business starts to take off, money starts flowing, you sell the business for life-changing wealth, and yet somehow struggle to keep the calendar open for what matters most. 

For many entrepreneurs, the pursuit of wealth and freedom slowly turns into a new set of obligations, responsibilities, and pressures that can be just as demanding as the life they were trying to escape.

That's why I'm excited to introduce you to my friend Joel Marion. Joel is a serial entrepreneur, 6-time bestselling author, direct-response marketing expert, and co-founder of BioTrust, a company that he helped scale to a 9-figure exit before his 40th birthday. Today, he mentors entrepreneurs and is launching Sound & Soul, a business focused on creating intimate live music experiences that bring people together through connection and shared memories.

In this conversation, Joel shares his unlikely journey from substitute teacher to entrepreneur with a huge exit, the lessons he learned from years of setbacks, and why some of his biggest breakthroughs came after his greatest disappointments.

In this episode, you’ll learn: 

✅ How Joel turned a failed book launch and a season of substitute teaching into the foundation for a business that generated millions in profit.

✅ Why one of Joel's most painful business setbacks taught him more about success, leadership, and fulfillment than any of his biggest wins.

✅ How Joel's definition of wealth evolved from chasing financial freedom to prioritizing time, relationships, and memorable experiences.

Show Notes: LifestyleInvestor.com/296

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

• Facebook
• YouTube
• Instagram
• LinkedIn
• Twitter

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

LIL #004: How the Ultra-Wealthy Actually Invest Their Money

The stock market isn't their strategy. It's their holding tank. Here's what the data reveals.

Episode Summary

In this episode of The Lifestyle Investor Podcast, host Justin Donald breaks down how the wealthiest families in the world actually allocate their portfolios, using data from Goldman Sachs, JP Morgan, and UBS. You'll learn why the ultra-wealthy borrow against stocks instead of selling them, where real wealth is created in inefficient markets, and why the "safe" 60/40 portfolio had one of its worst years in a century.

Question of the Day

What percentage of your portfolio is currently in the stock market vs. alternative investments? Drop a number below - no judgment, just curious where everyone's starting from.

Key Takeaways

• The wealthiest families hold over half their net worth in alternatives, not public equities
• Borrowing at 4-5% to invest at 12-15% is how the ultra-wealthy compound without selling
• Efficient markets offer no edge for retail investors - inefficient markets are where wealth is created
• One group of Austin centi-millionaires collectively holds just 5% in stocks
• Concentrate to make money, diversify to keep it - not the other way around

Timestamped Outline

00:00 - Introduction - the shift from public to private markets

00:28 - Why wealthy families keep money in stocks (not the reason you think)

00:52 - The arbitrage game - borrowing at 4-5% to invest at 12-15%

01:38 - Stacking returns - stocks, whole life policies, and compounding leverage

01:57 - The stock market as a holding tank, not a strategy

02:15 - Efficient markets vs. inefficient markets

03:02 - Where the real opportunity lives - private businesses and real estate

04:01 - What the ultra-wealthy actually invest in (family office data)

05:42 - The Austin centi-millionaire group that holds just 5% in stocks

06:46 - Why the 60/40 portfolio era is over

07:26 - Concentration to make money, diversification to keep it

09:00 - The shift from public to private - and what's coming next

Links & Resources

• Flash Boys by Michael Lewis (recommended read on retail investor disadvantage)
• The Lifestyle Investor Lens (weekly newsletter) - https://lifestyleinvestor.com/newsletter

Connect & CTA

Enjoyed this? Subscribe and leave a review on Apple Podcasts.

Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today: https://lifestyleinvestor.com/newsletter

Credits

Host: Justin Donald © 2026 Lifestyle Investor. All rights reserved.

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

Financial success is often described as the finish line, but reaching it doesn't always bring the fulfillment people expect. For many entrepreneurs, that ambition in the pursuit of more often comes at the expense of the relationships, values, and sense of purpose that matter most.

That's why I'm excited to welcome Rich Christiansen back on the podcast. Rich has founded or co-founded more than 50 companies throughout his career and has become a leading voice on values-based decision making, family legacy, and creating a life of true wealth. Through his work with entrepreneurs, executives, and family offices, Rich helps high-achievers live in alignment, dismantle limiting beliefs, ignite their passions and create a fulfilling life.

In this conversation, Rich shares a different perspective on what it means to be truly wealthy. Drawing from decades of entrepreneurial experience, including his work with a billionaire who broke down in tears after realizing he had damaged many of his closest relationships, Rich explains why fulfillment, peace, and meaningful connections are often the missing ingredients in a life that looks successful from the outside.

In this episode, you’ll learn: 

✅ Rich's framework for defining true wealth, building deeper relationships, and creating a life of flow instead of force.

✅ How to identify your true inner circle and strengthen your most important relationships.

Show Notes: LifestyleInvestor.com/295

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

• Facebook
• YouTube
• Instagram
• LinkedIn
• Twitter

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

LIL #003: 1,000 Lunches Taught Me More Than My Finance Degree

One weekly habit, 20 years, 1,000+ conversations - and a deal network no textbook could build.

Episode Summary

In this episode of The Lifestyle Investor Podcast, host Justin Donald breaks down the single habit that built his entire investment network - one lunch at a time, every week, for two decades.

You'll learn how a hands-on finance degree shaped his investing lens, why watching smart people follow the "right" playbook and never get ahead changed his trajectory, and how financial freedom removes fear from every decision.

Question of the Day

What's one relationship or conversation that fundamentally changed how you think about money or investing? Drop it in the comments.

Key Takeaways

• One consistent weekly habit compounded into 1,000+ high-caliber investor conversations
• Watching diligent people follow the textbook and never get ahead rewired his strategy
• Financial freedom changes every decision you make for your business and family
• The Lifestyle Investor Community's real value is the collective wisdom, not one person
• COVID turned weekly lunches into a virtual Investment Happy Hour that scaled everything

Timestamped Outline

00:00 - Introduction and recap of previous issues

01:08 - The one habit that changed everything

01:29 - 1,000 lunches in 20 years

02:11 - A finance degree with real practitioner training

02:46 - Watching people do the "right things" and never get ahead

03:28 - What the ultra-wealthy actually know

04:09 - Why this was always about family first

04:52 - Financial freedom changes every decision you make

05:43 - Building the Lifestyle Investor Community

06:11 - How COVID created something unexpected

06:49 - The community itself is the asset

07:20 - What's ahead for the Lifestyle Investor Lens

Links & Resources

• The Lifestyle Investor by Justin Donald - https://lifestyleinvestor.com/newsletter

Connect & CTA

Subscribe and leave a review on Apple Podcasts.

Every week, The Lifestyle Investor Lens breaks down what's changing in the world of wealth, what the wealthy are doing differently, and how to build passive income that funds your life today: https://lifestyleinvestor.com/newsletter

Credits

Host: Justin Donald © 2026 Lifestyle Investor. All rights reserved.

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