Moneywise

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.

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.

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.

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.

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.

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:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Alex’s stuff https://www.alexpeykoff.com/home

Chapters:

• Introduction to Alex Payoff's Story (00:00)
• Early Life and Family Background (01:38)
• Struggles with Wealth and Identity (04:25)
• The Wild Years: Drugs and Excess (06:17)
• Turning Point: Realizations and Reflections (13:26)
• Embracing Emotional Authenticity (19:12)
• Redefining Success and Happiness (19:34)
• Financial Freedom and Personal Crisis (20:08)
• The Car Obsession (21:48)
• Emotional Wealth vs. Emotional Debt (23:49)
• The Value of Real Estate Investments (32:20)
• Building Emotional Wealth (35:08)
• Join the Hampton Community (36:20)
• Podcast Production by Lower Street (37:05)

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

Inspired by real conversations happening in the Hampton community. Check out Hampton: https://www.joinhampton.com/

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.

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

Shane Cultra walked away from his family's five-generation nursery business—triggered, in part, by watching Succession. Along the way, he built up a $10M net worth, stacked Bitcoin, turned a blog into a domain empire, and made peace with a father who didn’t speak to him for a year after he left.

Here’s what we talk about:

• How Shane went from pit trader to plant farmer
• The domain side hustle that cashflows $300K+ a year
• Breaking down his $10M net worth: Bitcoin, land, stocks, and side gigs
• Why his dad thought success would make him lazy
• The real cost of working with family—and why he’d still do it all over again
• How Succession mirrored his life and led him to finally walk away
• The awkward equity breakdown: 33%, but no control
• Selling a blog for $75K and going all-in on digital real estate
• Why he’d rather make $18K for himself than $100K working for someone else
• Letting his daughter fail—and why that’s the lesson his dad never learned
• His exact monthly spending: $5,600/month, no mortgage, travel-heavy lifestyle
• From Porsches to a two-door Bronco: redefining what rich looks like
• $4M in stock holdings (including a $10K Apple investment for his daughter that grew to $400K)
• Why he's not pushing the family business to the next generation—and what legacy really means

Cool Links:

• If you’re a founder or CEO with $3M+ in revenue or funding, or you’ve sold a company for $10M+, check out Hampton: https://www.joinhampton.com/
• If you want a cool podcast like this one, check out Lower Street https://www.lowerstreet.co/
• Check out Shane's blog! https://www.botany.com

Chapters:
A Family Legacy in Crisis (00:00)
Shane's Financial Journey (00:31)
The Nursery Business Dynamics (04:51)
Shane's Early Career and Return to Family Business (09:12)
Navigating Family and Business Conflicts (11:49)
The Importance of Land Value (16:25)
Venturing into Domain Names (17:27)
The Unexpected Offer: Selling My Blog (21:07)
Family Tensions: Side Income and NFTs (21:43)
Measuring Wealth: Personal Stories (23:01)
Leaving the Family Business: A Tough Decision (24:59)
Reconciliation and Moving Forward (30:42)
Advice for Founders with Kids (33:41)
Financial Overview and Spending Habits (35:37)
Final Thoughts on Family Legacy (39:10)

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.

If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.

Mike Brown built an oil & gas empire, scaled his net worth to nearly $20 million, but ended up cash poor, losing $1.8M in a failed bet, and borrowing money from his wife to pay taxes. Now, he’s rebuilt his fortune, redefined what wealth really means, and is living a life designed around freedom, not just big numbers.

Here’s what we talk about:

• How Mike went from $2K in his bank account to making millions in oil & gas deals
• The "gold rush" mentality that led him to reinvest everything and regret it
• Why he thought $100M was the magic number (it wasn’t)
• The dangers of illiquid assets and chasing wealth at all costs
• Losing $1.8M on a distressed e-commerce acquisition 
• How divorce and bad bets forced a complete financial rethink
• Mike’s personal framework for financial freedom (12 months of liquidity, 5–7 years cash cushion, escape velocity)
• Why liquidity and cash flow > net worth
• His full portfolio breakdown today: fixed income, oil & gas, index funds, and zero angel investing
• The mindset shift: from "grow at all costs" to "invest for safety and joy"
• What it really feels like to sell your Lamborghini and love it
• How he's building a life he never wants to retire from — and helping other founders do the same

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Mike’s Wealth Business https://unbreakablewealth.com/

Chapters:
(00:00) Introduction to Mike Brown's Financial Journey
(02:36) Mike's Early Life and Money Lessons
(05:07) Navy to Entrepreneurship: The Million Dollar Deal
(07:24) The Gold Rush: Rapid Wealth Accumulation
(16:54) The Downfall: Divorce and Financial Struggles
(19:23) The E-commerce Disaster: Losing It All
(22:28) Rebuilding and Relying on Support
(24:55) Rebuilding with Cash Flow
(25:42) Lessons from Failure
(27:02) Current Portfolio Strategy
(28:41) Cash Flow and Investments
(31:11) Financial Freedom Levels
(33:53) Personal Monthly Burn and Joy
(36:17) Redefining Wealth and Happiness
(42:12) The Irony of Wealth
(47:24) Final Takeaways and Community

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.

If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.

There is no amount of money that will make you happy. There is also no amount that will stop making you more happy. 

Both of those things are true.

Our producer is not rich. But she has talked to 100+ people who are, and she (I) has learned a lot about your kind (is that wrong to say?).

In the Moneywise pilot, we asked the question “at what point will more money stop making you happy”. Turns out, that was a pretty stupid question. So in this episode, we’re fixing that.

This is an episode of Moneywise unlike any other. This is a solo essay-style inside-outsider's take on wealth and happiness, based on the past year of peaking behind the curtain at what truly makes millionaires lives better… and worse. Backed up by quotes from our guests and of course, real studies.

Here’s what we talk about:

• Money doesn’t make you happy. It can only remove stress.
• The “happiness number” is a myth but knowing your “freedom number” changes everything.
• Most people don’t want money, they want the freedom they think money will give them.
• Hitting your financial goal won’t feel like you imagined.
• Founders often feel lost post-exit because they unknowingly traded hope for cash.
• Wealth adds new stress.
• Money can’t buy you meaningful experiences, and you need to stop thinking it can.
• If you expect money to do the emotional heavy lifting in your life, you will never be satisfied.
• Money is the key, not the door. It unlocks your potential but it won’t add anything more to your life.

Cool Links:

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

Chapters:
(00:00) Introduction and Confession
(00:35) Reflecting on 50 Episodes
(02:24) Revisiting the Happiness Threshold
(03:09) Money as a Subtractive Tool
(03:48) The Freedom Number vs. Happiness
(05:07) Studies and Research on Wealth and Happiness
(14:39) The Hedonic Treadmill and Wealth's Paradox
(17:45) Hope and the Entrepreneur's Journey
(25:26) Concluding Thoughts and Freedom Numbers

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.

References:

• Kahneman, D., & Deaton, A. (2010). "High income improves evaluation of life but not emotional well-being." Proceedings of the National Academy of Sciences, 107(38), 16489-16493. DOI: 10.1073/pnas.1011492107
• Jebb, A. T., Tay, L., Diener, E., & Oishi, S. (2018). "Happiness, income satiation and turning points around the world." Nature Human Behaviour, 2, 33-38. DOI: 10.1038/s41562-017-0277-0
• Killingsworth, M. A. (2021). "Experienced well-being rises with income, even above $75,000 per year." Proceedings of the National Academy of Sciences, 118(4). DOI: 10.1073/pnas.2016976118
  Link, B. G., Phelan, J., Bresnahan, M., Stueve, A., & Moore, R. E. (1995). American Journal of Orthopsychiatry, 65(3), 347-354. DOI: 10.1037/h0079653
• Donnelly, G. E., Zheng, T., Haisley, E., & Norton, M. I. (2018). "The Amount and Source of Millionaires’ Wealth (Moderately) Predicts Their Happiness." Personality and Social Psychology Bulletin, 44(5), 684-699. DOI: 10.1177/0146167217746340
• Luthar, S. S., & Becker, B. E. (2002). "Privileged but Pressured? A Study of Affluent Youth." Child Development, 73(5), 1593-1610. DOI: 10.1111/1467-8624.00492.

If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.

Eran Galperin bootstrapped a niche SaaS for Brazilian Jiu-Jitsu gyms, sold it for $32.5 million, moved to Japan, and is now quietly living the FIRE dream — with a few luxury upgrades.

Here’s what we talk about:
- How Eran went from $15K in the bank to a $32M exit (with 90% equity!)
- Why he ignored VCs and chose to bootstrap — and how it paid off years later
- The long, slow ramp: 4 years to $12K MRR, 8 years to $3M ARR
- The FIRE mindset that guided his financial decisions from day one
- How and why he moved to Japan — including taxes, cost of living, and lifestyle
- What it actually cost to move abroad and build a luxury home in Tokyo
- His full post-exit portfolio breakdown (hint: most of it’s in index funds)
- What it’s like working after the exit — and why he’s still showing up
- The one splurge that changed his mindset about spending
- The emotional reality of selling your company — and why it felt more like relief than celebration
- Why he's mentoring early-stage founders and learning real estate development — just for fun

Cool Links:
Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/
FIRE Subreddit https://www.reddit.com/r/Fire/?rdt=37862
fatFIRE Subreddit https://www.reddit.com/r/fatFIRE/

Chapters:
(00:00) The $32 Million Exit
(01:48) Why FIRE
(08:31) The Slow SaaS Ramp of Death
(12:49) The Big Move to Japan
(14:32) Financial Optimization and the Exit Strategy
(19:05) The Final Deal: $32.5 Million Sale
(23:25) Financial Breakdown and Initial Investments
(26:03) Post-Exit Financial Planning
(28:19) Lifestyle Changes and Spending Habits
(33:49) Building a Dream Home in Tokyo
(38:52) Continued Work and New Ventures
(42:30) Final Thoughts and Future Plans

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

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