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.