How Rich Is ‘Rich Enough’ to Fly Private?

Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/ 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. A message from our Sponsors: Oceans helps fast-growing teams scale smarter with world-class offshore talent. Learn more at https://www.oceanstalent.com/ 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: The Allure of Flying Private 00:24 The Realities of Flying Private 01:04 Types of Private Jet Ownership 01:39 Chartering vs. Owning: Costs and Considerations 04:25 Fractional Ownership Explained 06:39 Co-Ownership: Pros and Cons 07:15 Full Ownership: Is It Worth It? 07:40 Understanding Private Jet Classes 18:47 The Hidden Costs of Private Jet Ownership 22:18 Who Actually Owns Private Jets? 25:37 The Value of Time and Convenience 32:41 Buying New vs. Used Jets 33:58 Beware of Scams in the Private Jet Market 34:27 Conclusion: Is Flying Private Worth It? 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. Jet reference picture sources: TCM960 - Flieger Magazin: https://www.fliegermagazin.de/ PC12 - Private Jet Charter: https://www.privatejetcharter.de/ King Air - Aircraft Exchange: https://aircraftexchange.com/ Citation M2 - Air Charter Service: http://aircharterservice.com/ Phenom 300 - JetCraft: https://www.jetcraft.com/ Citation XLS - JetCraft: https://www.jetcraft.com/ Super Mid Size - Luna Jets: https://www.lunajets.com/ Challenger 650 - JetCraft: https://www.jetcraft.com/ G700 - Gulfstream Aerospace: https://www.gulfstream.com/