Moneywise

Latest Episodes:

A $2.5B Exit and The Risks Nobody Talks About Dec 04, 2024

Show notes

What happens when wealth pushes your relationships to the limit?

Navigating life after a massive financial windfall isn’t easy—it can transform your life, your marriage, and your happiness in unexpected ways.

Our guest, Chuck, shares his story of selling his company for $2.5 billion and the emotional and relational challenges that followed. His perspective is shaped not only by his own journey but also by a family history of building and losing fortunes.

Chuck’s background is as bold as it gets. By 28, he was making $800K a year in sales, but he risked it all to build a company from scratch. That gamble paid off, with his business growing to hundreds of millions in revenue before selling in a deal that changed his life forever. However, the wealth brought its own struggles—unexpected divides in his marriage, a sense of purpose lost, and lessons about how money can either enhance or destroy a family.

This is Moneywise, a podcast where hosts Sam Parr and Harry Morton are joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits.

Who is Sam Parr?

Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022.

Check out Sam’s Companies:

Hampton

Sam’s List

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Chuck's Early Success and Business Journey (03:31)

Building and Scaling the Business (04:39)

The Emotional Rollercoaster Post-Exit (06:14)

Financial Responsibility and Spending Philosophy (09:37)

Generational Wealth and Family Dynamics (12:45)

Entrepreneurial Spirit and Taking Risks (16:25)

The Role of a Supportive Partner (18:15)

Taking Risks Together (18:48)

Emotional Decisions Over Financial Ones (19:42)

Reflecting on Happiness and Money (23:20)

Balancing Wealth and Family (27:30)

Chuck's Spending Habits (28:27)

Advice to Younger Self (31:28)

This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

Sold For $80 Million - Then Hit Rock Bottom Nov 26, 2024

Show notes

What happens when the big exit doesn’t fill the void?

Josh Payne thought selling his company for $80 million would be the defining moment of his life. Instead, it sent him into one of the darkest periods he’d ever experienced.

Josh’s story is a testament to the complexity of success. As the founder of StackCommerce, Josh grew his company from $0 to $32 million in annual revenue, eventually selling it for a life-changing sum. But with his emotional wellbeing tied so closely to his business success, he found himself struggling to find purpose once his goal was achieved.

In this episode, you’ll learn how Josh’s early years in the Midwest shaped his drive for entrepreneurship, what it felt like to grow a company from nothing to millions—and why he struggled when growth slowed, the challenges and emotions of selling his business and suddenly becoming a multi-millionaire, as well as how he found his way out of post-sale depression through therapy, family, and physical challenges like completing an Ironman and why Josh is now building a new company—but this time, with a focus on joy, service, and sustainability.

Who is Sam Parr?

Check out Sam’s Companies:

Hampton

Sam’s List

Who is Harry Morton?

Harry Morton is the CEO of Lower Street, a company specializing in premium podcast production that he founded to transform brand narratives through audio storytelling. His expertise has made Lower Street a leader in the podcast industry, working with diverse clients from startups to Fortune 500 companies to enhance their market presence and audience engagement.

This episode also features an interview conducted by Andrew Namanny. Check out his podcast Permission to Shine.

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Josh's Finances and Origin Story (02:37)

Early Career and Entrepreneurial Drive (06:37)

Founding Stack Commerce (08:44)

Revenue Growth and Financial Success (08:58)

Emotional Struggles and Existential Threats (10:18)

The Exit Process (14:04)

Post-Exit Realizations (16:14)

The Illusion of Financial Fulfillment (18:02)

Reassessing Values and Spending (24:36)

New Business Ventures and Goals (30:35)

Reflections on Success and Fulfillment (34:38)

This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

$7 Million at 18 to $112 Million in Assets: How Jacob Turner Built a Business After the MLB Nov 19, 2024

Show notes

What would you do if you became a millionaire at 18? For MLB pitcher Jacob Turner, the real question was: how do I make sure I don't lose it all?

Jacob signed a $7 million contract with the Detroit Tigers as a teenager, and suddenly, his life changed overnight. While most of us can’t imagine dealing with that level of wealth so young, Jacob had to figure it out fast—and he didn’t want to be another cautionary tale of an athlete who blew it all.

Jacob Turner isn’t just a former MLB pitcher—he’s a financial expert with a mission. After a decade in professional sports, he transitioned into the financial world to help athletes and entrepreneurs navigate wealth.

In this episode, we’ll explore the psychology of sudden wealth and how Jacob handled becoming a millionaire overnight at just 18. He shares lessons learned from his time in professional sports, including navigating the pressures of wealth disparity and resisting lifestyle inflation. Plus, you’ll hear how he transitioned into entrepreneurship, grew his financial advisory firm, and why he believes balancing purpose with wealth is the key to long-term success.

We’ll also step into the financial locker room of pro ball players, getting a glimpse at how they really get paid and where their money goes.

This is Moneywise, a podcast where hosts Sam Parr and Harry Mortonare joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits.

Who is Sam Parr?

Who is Harry Morton?

This episode also features an interview conducted by Andrew Namanny. Check out his podcast Permission to Shine.

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Jacob's Early Financial Experiences (01:59)

Realizing Professional Potential (06:01)

Navigating Sudden Wealth (07:33)

Learning from Teammates' Financial Decisions (11:07)

The Condensed Financial Timeline of Athletes (15:52)

The Reality of Post-Athlete Life (19:46)

Finding New Purpose (21:04)

Lessons from Financial Advising (30:12)

New Attitudes Towards Investment (33:49)

The Value of Purpose Over Wealth (38:17)

Conclusion and Final Thoughts (40:06)

This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

Top Money and Life Secrets from 25 Millionaires: What You Should REALLY Know Oct 29, 2024

Show notes

We just hit our 25th episode! To celebrate, we’re doing a special recap of the best lessons from all our past conversations. Sam’s looking back at the standout advice from founders, entrepreneurs, and experts who opened up about what really happens when you hit major financial success—and the stuff no one talks about.

You’ll hear insights from Mike Beckham on why giving back keeps lifestyle inflation in check, Dr. Becky’s take on raising resilient kids in a world of privilege, and advice from founders who’ve faced the mental rollercoaster that comes after big exits. We also dig into what it means to live a low-key, fulfilling life, even if you’re worth millions.

Who is Sam Parr?

Who is Harry Morton?

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Lesson 1: Finding Purpose After Early Retirement (01:47)

Lesson 2: Raising Resilient Children in Wealthy Environments (04:28)

Lesson 3: The Impact of Giving (06:55)

Lesson 4: Stress and Growth vs. Peace and Letting Go (09:22)

Lesson 5: Jennifer's Story: Financial Red Flags in Relationships (13:57)

Lesson 6: Financial Stress: A Wild Story of Loss and Resilience (16:32)

Lesson 7: Beware of Burnout: Lessons from Ryan and Pete (18:46)

Lesson 8: Small Town Success: Travis's Story (21:25)

Lesson 9: Knowing When to Walk Away: Laura and Jeff's Insights (24:14)

Sam’s Personal Top Takeaways (27:45)

This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

$100M Net Worth, $5M Income: How I used money to handle a cancer diagnosis Oct 15, 2024

Show notes

What’s the true value of money when faced with a life-or-death situation?

Mitch found out the hard way when his wife was diagnosed with cancer.

As a highly successful entrepreneur with a net worth of nearly $100 million, Mitch had built a life of financial security. But when faced with his wife’s illness and his own health scare, he discovered that no amount of money could buy control over life’s toughest moments.

Mitch's story is one of resilience, from his early entrepreneurial days, selling candy out of his locker, to growing a business worth millions. He reflects on the emotional and personal costs of his financial success and how his near-death experience completely shifted his perspective on wealth, work, and family.

Who is Sam Parr?

Who is Harry Morton?

This episode also features an interview conducted by Aaron Hayslip.

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Mitch's Early Entrepreneurial Spirit (03:25)

First Taste of Wealth and Career Choices (05:24)

Health Scare and Perspective Shift (13:30)

Reflecting on 2019: A Pivotal Year (21:36)

Turning Down a Billion-Dollar Offer (22:03)

Starting from Scratch: The Independent Journey (24:08)

Facing a New Challenge: Breast Cancer Diagnosis (28:48)

The Emotional Toll and Family Struggles (30:27)

The Role of Wealth in Healthcare Access (33:41)

Reevaluating Wealth and Power (37:35)

Investing in Experiences (39:37)

The Limits of Wealth and Final Reflections (40:40)

This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

“I’m worth about $3 billion” What Happens When You DON’T Sell Your Business Oct 08, 2024

Show notes

What happens when you don’t sell your company and keep growing it for decades?

For Oscar, it means you become a billionaire.

Oscar bought a company every six weeks for 20 years and now his business is worth about $50 billion. Yet, he still wears $15 t-shirts and lives by the values that helped him achieve success.

In this episode, he shares how he became a billionaire while always putting family and faith first. He discusses his humble beginnings, the influence of his father, and how he’s now passing on his wealth through a generational trust. From managing a $3 billion stake in his company to owning 300 classic cars and a $49 million private jet, Oscar’s story offers a glimpse into life after massive success—without ever sacrificing who he is.

Who is Sam Parr?

Who is Harry Morton?

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Oscar's Lifestyle and Major Expenses (02:32)

Military Service and Its Impact (11:18)

Building a Business Empire (13:59)

Walking Out on Investment Bankers (22:54)

Sacrifices for Business Growth (24:58)

Family Support and Business Success (28:10)

Wealth Management and Generational Planning (32:47)

Investment Strategies and Mistakes (37:01)

Advice for Young Entrepreneurs (39:29)

This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

"I Thought I Had the Midas Touch": How an $80M Success Led to a Major Failure Oct 01, 2024

Show notes

Can success create a false sense of invincibility? For Pete, it did—and it cost him millions.

After selling his business for $80 million, Pete felt unstoppable. But his overconfidence led him into a risky venture that didn’t pay off. Determined to prove he wasn’t a one-hit wonder, Pete ignored the warnings, thinking his past success guaranteed future wins. Instead, he faced one of the hardest losses of his career.

In this episode, Pete shares how his upbringing shaped his hunger for security, how overconfidence after a major exit led to a business failure, and how he’s rebuilding emotionally and financially.

This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits.

Who is Sam Parr?

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Pete's Humble Beginnings (01:45)

Early Entrepreneurial Ventures (05:00)

The Big Exit and Its Impact (07:03)

Post-Exit Lifestyle and Spending (09:13)

The New Venture and Its Challenges (10:56)

Realizing the Mistake (22:57)

Financial and Emotional Impact (23:52)

Lessons Learned and Moving Forward (28:17)

Redefining Success (35:31)

Conclusion and Final Thoughts (36:48)

This podcast was produced in partnership with Lower Streetand distributed by Morning Brew.

"How I quit the hustle to enjoy life”: Getting Off the Treadmill with a $15m Net Worth Sep 24, 2024

Show notes

How Do You Stop Hustling When You’ve Already Won?

Laura Roeder told herself that at $5 million liquid she could live the life she wanted and refocus her life on what matters most: living. Unlike a lot of entrepreneurs who get caught up in the game and keep chasing more, Laura stayed true to that goal and quit hustling harder than she had to. But how did she avoid the endless treadmill for more?

Laura Roeder, founder and successful SaaS entrepreneur, joins the show to share her journey of hitting her financial target, choosing simplicity, and focusing on what matters most. With a net worth of over $15 million, she explains how she prioritized lifestyle over accumulation, and how her upbringing played a key role in shaping her financial mindset.

In this episode, Laura discusses how she hit her financial goal and resisted the temptation to keep pushing for more. You’ll also hear about her business philosophy, why she believes in running a business for lifestyle and not just growth, and the importance of knowing when enough is enough. Plus, she dives into her personal investments, expenses, and how she balances wealth with family time.

Who is Sam Parr?

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Laura’s Financial Foundation (03:54)

Balancing Lifestyle and Financial Goals (07:14)

Starting and Scaling Businesses (13:21)

Selling the Business and Life After Exit (19:13)

Lifestyle Business vs. Growth Business (21:41)

Laura's Investments and Expenses Breakdown (24:18)

Balancing Work and Personal Life (30:09)

Avoiding the Comparison Trap (32:54)

Final Thoughts on Wealth and Happiness (36:33)

This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

What It’s Like to be Worth $50M in a 2400 Person Town Sep 17, 2024

Show notes

Ever wondered what it feels like to be the richest person in a tiny town in the middle of nowhere?

Today’s guest, Travis, is worth $50m, yet he’s never been tempted to leave his hometown of 2400 people.

Travis has already had an exit of $25m, and he’s about to double that with a second exit. Now he’s navigating life as the local big shot. From curious neighbors asking about his money to balancing wealth without being flashy, Travis shares the surprising perks—and awkward challenges—of being a big fish in a very small pond.

In this episode, Travis shares why he chose to keep his family and business in a small town and why he believes more people should consider doing the same. He reveals the highs and lows of small-town life after wealth, from nosy neighbors to giving back to his community in ways that wouldn’t be possible in a big city..

Who is Sam Parr?

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Travis's Business Journey (02:48)

Challenges of Wealth in a Small Community (11:44)

Spending and Lifestyle Choices (15:29)

How He’s Invested (20:30)

Impact on the Community (24:27)

Raising Kids in a Small Town (34:12)

Conclusion and Advice (37:14)

This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

"I didn't have any idea what I was spending:" Nearly Burning Through a $13M Exit Sep 10, 2024

Show notes

13 million dollars is a lot. But is it enough to retire on?

For pre-epiphany Ryan Begelman, the answer is no.

Ryan built his wealth working in the corporate world, then decided to risk it all and bought into Bisnow. That risk paid off, and Ryan made a huge profit. But despite his successes, he found himself grappling with lifestyle inflation, misguided investments, and financial uncertainty.

In this episode, Ryan opens up about his struggles with managing wealth after a big exit, how flashy spending left him unprepared, and why life coaching became the tool that helped him find real security. We dive deep into his financial epiphany, his coaching career, and how he halved his spending while learning to respect money in a whole new way.

Who is Sam Parr?

This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.

Chapters:

Ryan's Early Career and BizNow Success (02:32)

Financial Mismanagement and Realizations (06:09)

Family Influence and Flashy Spending (09:37)

Life Coaching and Personal Epiphany (12:38)

The Start of a Coaching Journey (20:05)

Financial Success and Security (20:45)

Existential Financial Concerns (22:44)

Modeling for Financial Future (23:17)

Spending Adjustments and Reflections (26:56)

Endurance and Self-Care in Business (32:38)

Final Thoughts and Reflections (38:24)