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.
