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

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.

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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:

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:

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:

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.

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