Moneywise

Latest Episodes:

$10M vs $100M: The Difference Between Being Rich and Really Rich Jul 01, 2025

Show notes

Jackie breaks down exclusive data from 127 millionaire founders inside Hampton, revealing how motivation, money management, and mindset evolve as net worth grows, from $1M to over $100M.

Here’s what we talk about:

Why financial security stops being a motivator after $50M—and what takes its place
The "F*** You" number: What real numbers show is the threshold for total financial freedom
Wealth allocation shifts: Crypto disappears, bonds and real estate dominate at the ultra-high end
Surprising insights into monthly cash burn, and how spending changes (or doesn’t) across net worth tiers
Take-home income jumps dramatically past $50M—especially at the $100M+ level
Time vs. money: Wealthier founders are working fewer hours, but that doesn’t guarantee happiness
What motivates founders at every stage—and why some feel lost after hitting their big number
Real quotes from founders like Brian Johnson and Alex Peykoff on why they build, invest, and spend the way they do

$50M is when founders stop caring about money entirely. Want to see what other millionaire money secrets we uncovered in the full report? https://www.joinhampton.com/wealth-report

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/

Chapters:

(00:29) Survey Insights: Wealth Allocation and Trends
(01:02) Understanding the Respondents
(03:09) Motivations and Milestones of Millionaire Founders
(04:13) Case Study: Bryan Johnson's Unique Motivation
(05:47) Financial Security and Lifestyle Changes
(08:47) Money Management: Crypto, Bonds, and Real Estate
(10:46) Cash Flow and Spending Habits
(16:14) Work-Life Balance and Happiness

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

You Host - Jackie Lamport

Not really the host, but the producer.
Wrote this sentence.
Older than I appear, I promise.

Re-Up: I’m Worth ~ $500m. Here’s What I Regret (And Don’t) Spending On with Andrew Wilkinson Jun 24, 2025

Show notes

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report.

Andrew Wilkinson became rich in his 20s — but early wealth came with hard lessons. In this episode, Andrew opens up about:

How he went from buying everything he wanted to nearly going bankrupt in 2008
The emotional rollercoaster of building and losing wealth while still young
What it's actually like to cross the nine-figure mark
Why luxury spending doesn’t always bring happiness
How wealth impacts family, friendships, and personal identity
His thoughts on giving back, donating money, and the real ROI of generosity

Chapters
(00:00) Introduction
(00:21) Meet Andrew Wilkinson: Early Success and Challenges
(02:38) The Reality of Wealth: Lessons Learned
(03:14) Building Businesses: From Design Agency to Diversification
(06:54) The First Big Sale: A Turning Point
(09:28) Spending Habits: What Worked and What Didn't
(20:39) The Impact of Wealth on Family and Relationships
(23:00) The Complexity of Doing Good with Money
(27:02) Conclusion: Reflections on Wealth and Happiness

Sam Parr
Founder of Hampton, a private community for 7-figure founders. Previously sold his company, The Hustle, to HubSpot for tens of millions.

I Let Go of the Hustle. Embraced Feminine Leadership. Built $10M. Jun 17, 2025

Show notes

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Jess Chan scaled to 7 figures fast, then tore it all down. Today, she’s worth ~$10M, spends less than ever, and says profit > revenue every time.

Here’s what we talk about:

Jess hit $40K/month as a freelancer, then walked away to build her agency, Longplay.
Why chasing $1M in revenue nearly burned her out, and what she did to rebuild.
The shift from ego-driven growth to sustainable, profitable business.
How embracing feminine leadership transformed her company and her life.
Her net worth is ~$10M, but her monthly spend has dropped to ~$6K.
The underrated skill: learning how to spend money well.
Why contentment and ambition can coexist and how chasing more can actually cost you.
Jess’s financial setup: super simple. Mostly ETFs. Barely checks it.

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/

Chapters:
(00:00) Introduction to Jess Chan's Journey
(00:58) Early Revenue Chase and Freelancing
(02:03) Building and Scaling Long Play
(02:55) Challenges and Burnout
(04:42) Rebuilding and Stabilizing
(06:14) Shifting Focus from Revenue to Profit
(08:20) Embracing Feminine Leadership
(15:03) Redefining Wealth and Success
(19:37) Breaking Free from Business Metrics
(20:21) Childhood Reflections and Entrepreneurial Drive
(22:09) The Unexpected Path to Entrepreneurship
(27:41) Transparency in Financial Success
(31:57) Personal Finance and Contentment
(37:00) Balancing Ambition and Contentment

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
Co-parents a cow named Eliza.

How Much Does It Really Cost to Fly Private? Jun 10, 2025

Show notes

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Is flying private a waste of money, or the ultimate time hack for the ultra-wealthy? In this episode, we break down what it really costs, who it makes sense for, and why even billionaires think twice.

Here’s what we talk about:

Private aviation expert Preston Holland explains the true cost of flying private, from charter to full ownership.
When does it make financial sense? Around $2M in income and $20M net worth.
Why fractional ownership is trending, even for people who can afford full planes.
Guests like Andrew Wilkinson, Josh Payne, and Nick Huber share how and why they fly.
The real costs: pilots, insurance, hangars, maintenance, and depreciation.
Who flies private most: rural founders, franchise owners, post-monetary entrepreneurs.
Flying yourself? FinTech founders and control freaks, take note.
A PSA: Jets don’t make money, don’t fall for “fly for free” scams.
Jackie reflects on patience vs. buying back time.

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/
Preston’s Twitter https://x.com/prestonholland6
Preston’s Newsletter: https://prestonholland.com/bio

Chapters:

(00:00) Introduction and Andrew Wilkinson's Private Flying Experience
(00:48) Exploring the Costs and Benefits of Flying Private
(01:51) Types of Private Jet Ownership
(03:12) Chartering vs. Owning: Financial Considerations
(05:06) Fractional Ownership and Co-Ownership
(07:52) Full Ownership: Pros, Cons, and Costs
(12:28) The Realities of Owning a Private Jet
(15:16) Entrepreneurs and Private Flying
(32:20) The Environmental and Financial Costs of Private Jets
(34:41) Conclusion and Final Thoughts

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

You Host - Jackie Lamport

Not really the host, but the producer.
Wrote this sentence.

$60M Exit, 25+ Deals, and Why Angel Investing Isn’t For Most | Auren Hoffman Jun 03, 2025

Show notes

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Auren Hoffman reveals the unglamorous truth about angel investing—why he still does it, what he’s learned, and why it’s not for everyone.

Here’s what we talk about:

Auren Hoffman made $60M—and then became an angel investor.
He shares why angel investing isn’t as sexy as it sounds.
The truth about money: yes, it did make him happier.
How he tracks spending (only big and small stuff—never the middle).
Why he never sets goals and doesn’t chase happiness.
His step-by-step guide to being unhappy (for real).
How trash-talking saved LiveRamp from a PR meltdown.
The right way to invest after a big exit (hint: take it slow).
Why most people shouldn’t even think about investing before hitting $3M.
Sam and Auren go deep on process vs. planning—and what really drives success.

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/
Auren’s Twitter https://x.com/auren

Chapters:
(00:00) Auren Hoffman's Big Exit
(00:17) The Reality of Angel Investing
(00:53) Introducing Moneywise
(01:02) The Hampton Community
(02:23) Auren's Early Entrepreneurial Journey
(03:39) First Million in the Twenties
(06:47) LiveRamp and the $60 Million Exit
(07:52) Handling Wealth and Lifestyle Changes
(12:00) Navigating Business Challenges
(13:56) Entrepreneurial Mindset and Resilience
(15:33) The Importance of Community for Founders
(17:17) Navigating Uncertainty in Business
(17:40) Insights from Successful Founders
(18:26) Auren's Journey Post-Big Exit
(19:44) Balancing Work and Personal Fulfillment
(21:05) The Philosophy of Happiness and Success
(28:52) Advice on Angel Investing

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Sam Parr

Founder of Hampton, a private community for CEOs.
Sold his last company, The Hustle, for tens of millions.

How Nick Huber Stays Humble with a $50m Net Worth and 25k Burn May 27, 2025

Show notes

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

He’s worth 8 figures, owns a private jet, and still tracks every dollar. Nick Huber says avoiding lifestyle creep is harder, and more important, than getting rich.

Here’s what we talk about:

How Nick Huber built an 8-figure net worth from sweaty startups and smart real estate plays.
Why he keeps over $2M liquid and doesn’t touch stocks.
His exact monthly burn (yes, including the jet) and how he keeps it under $25K.
The psychology behind lifestyle creep, and why he’s borderline paranoid about fixed costs.
Why he’d rather live modestly than risk losing what he’s built.
The emotional rollercoaster of lumpy cash flow, $900K tax bills, and late-night financial dread.
How he justifies buying a private jet.
His next goal: $1M/month in personal profit, and why he's not trying to be a media mogul along the way.

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/
Nick’s Stuff https://www.nickhuber.com/

Chapters:

(00:00) Introduction to Nick Huber's Success
(00:48) Nick Huber's Financial Journey
(01:20) Breaking Down Net Worth and Assets
(03:12) Cash Flow Management
(05:16) Nick's Humble Beginnings
(08:49) Entrepreneurial Lessons and Challenges
(13:44) The Rise of Storage Squad
(17:42) Maintaining Frugality Despite Wealth
(20:10) Managing Lifestyle Creep
(22:09) The Justification for Owning a Jet
(24:11) Avoiding Fixed Costs
(24:56) Balancing Ego and Humility
(30:45) The Role of Media in Entrepreneurship
(35:57) The Emotional Roller Coaster of Entrepreneurship
(39:16) Conclusion and Final Thoughts

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.

Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
Co-parents a cow named Eliza.

+$100M Exit, Then I Failed. Why 70% of Second-Time Founders Do Too. May 20, 2025

Show notes

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

After a nine-figure exit, Anastasia Koroleva went through divorce, failure, and identity loss. She reflects on what she didn’t see coming.

Here’s what we talk about:

Anastasia’s journey from a bootstrapped nine-figure success to divorce, burnout, and identity loss
Why second businesses often fail, and how success the first time around can actually work against you
The four biggest traps post-exit founders fall into: rushing into something new, chasing unfamiliar industries, losing self-awareness, and falling into “Sudden Wealth Syndrome”
How to rebuild your life after selling a company using frameworks like Maslow’s hierarchy and cognitive dissonance theory
Why wealth alone doesn’t create fulfillment, and what actually does
Anastasia’s personal portfolio strategy: no wealth manager, heavy in private credit, designed for low stress and high flexibility
A real look at her post-exit lifestyle, including two homes and $650K to $1M in annual spending
How long it truly takes to feel whole again after an exit, and why slowing down might be the smartest move
Why she now spends her time helping other founders avoid the same mistakes

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/
Anastasia’s Podcast https://www.exitparadox.com/

Chapters:

(00:00) Introduction: The Big Picture Trap
(00:56) Meet Anastasia's Net Worth
(03:14) Anastasia's Early Life and Career Beginnings
(04:19) The Silicon Valley Leap and First Ventures
(07:25) The Emotional Rollercoaster of Success
(09:25) Post-Exit Challenges and Personal Struggles
(17:55) The Psychology of Second Ventures
(24:26) Understanding Sudden Wealth Syndrome
(28:20) Minimizing Psychological Discomfort Post-Exit
(29:37) The Paradox of Wealth and Freedom
(31:30) Confronting Financial Freedom
(32:48) The Third Level of Wealth
(33:30) Emotional Challenges and Evolution Post-Exit
(34:49) Rebuilding the Basics: The Maslow Pyramid
(35:44) The Goldilocks Approach to Post-Exit Life
(48:07) Managing Wealth Post-Exit

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.

Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
Co-parents a cow named Eliza.

My $70M Exit Collapsed Days Before Signing May 13, 2025

Show notes

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

Adam Robinson was days away from a $70M exit… then the buyer walked. But the deal collapsing turned out to be a blessing.

Here’s what we talk about:

His current company now does $25M ARR with $1M monthly profit.
He accidentally spent millions before the deal closed on land, crypto, and a new mortgage.
Then came a surprise 60% tax bill, thanks to a little-known IRS rule.
Adam explains why high income doesn’t equal peace of mind.
He shares how Wall Street shaped his risky money habits.
His spending: $750K/year, two kids, boat, Aspen trips, wellness lifestyle.
He admits he wasn’t ready for a big exit and still might not be.
Now, he’s focused on structure, restraint, and building wealth slowly.
And why cash flow feels better than a windfall… at least when you’re winning.

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/

Chapters:
(00:00) The Big Exit That Never Happened
(00:54) Adam's Financial Resilience
(02:25) From Wall Street to Startups
(06:59) The Startup Struggles
(10:31) The Almost Sale and Its Aftermath
(12:35) Crypto Craze and Financial Lessons
(15:13) Rebounding and Learning from Mistakes
(19:21) The Genius Trade of the Century
(22:38) Financial Anxiety and Business Risks
(25:26) Tax Surprises and Financial Planning
(29:27) Spending Habits and Lifestyle Choices
(36:28) Balancing Wealth Building and Lifestyle
(37:14) Conclusion: The Exit That Wasn't

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
Co-parents a cow named Eliza.

$100K Buy-In. $160M Exit. Then $40K/Month on ‘Living the Dream’... Almost. May 06, 2025

Show notes

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

After a $100M+ exit, Jace Mattinson blew $40K a month chasing lost time, until living the dream nearly ruined it.

Here’s what we talk about:

Jace shares how he turned a failing 135-year-old business into a $160M exit.
Why buying old and boring beat building from scratch.
He hit a $5M net worth—then spent $40K/month trying to “make up for lost time.”
The moment he realized leisure can become just another grind.
How he and his wife navigated the emotional hangover of success.
Why founders struggle with freedom, and how he learned to enjoy it.
His strategy for protecting wealth and living fully.
His monthly expenses for a family with 5 kids under 7.
The framework he uses to make time, money, and values actually align.

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/
Book mentioned: Die With Zero by Bill Perkins

Chapters:
(00:00) The Grind and Delayed Gratification
(01:41) Financial Breakdown and Investments
(03:37) From Corporate Life to Entrepreneurship
(05:10) The Influence of Upbringing
(07:03) Meeting His Wife and Changing Perspectives
(08:47) Turning Around a Struggling Business
(14:21) The Exit and New Challenges
(15:49) Life After the Sale
(18:47) Balancing Family and Personal Time
(19:18) Indulging in Expensive Hobbies
(20:50) Spending on Experiences vs. Investments
(23:26) Finding Balance in Hobbies and Work
(27:05) Intentional Living and Regrets
(30:18) Current Monthly Expenses and Hobbies
(35:55) Future Plans and Bucket List

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
Co-parents a cow named Eliza.

$100M Lifestyle, Billionaire Family — The Call That Changed Everything | Alex Peykoff Apr 29, 2025

Show notes

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

What happens when you grow up alongside a billion-dollar company, lose yourself chasing money, drugs, and approval, and have to rebuild your life from scratch? That’s what happened to Alex Peycoff.

Here’s what we talk about:

Why growing up in a soon to be billionaire status family taught Alex the wrong lessons about value and self-worth.
How wild drug-fueled nights and empty relationships left him feeling more isolated than ever despite immense wealth.
The life-altering moment with his daughter that redefined his understanding of success, money, and emotional presence.
How Alex rebooted his life, built "emotional wealth," and developed a purpose beyond material success.
Why he keeps all his money in real estate and avoids markets and crypto.
Alex’s personal definition of emotional debt and how clearing it created the biggest transformation of his life.
His current net worth ("north of a couple hundred million dollars") and how he manages it differently now.

Cool Links: