How Much Does It Really Cost to Fly Private?

Moneywise

Hampton

Business, Entrepreneurship, Investing

4.8 • 674 Ratings

🗓️ 10 June 2025

⏱️ 40 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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.

Transcript

Click on a timestamp to play from that location

0:00.0	All right, so here's the deal. I just came from our 25-person all-hands meeting with all my staff at Hampton.
0:08.3	Right after the meeting finished, it was now time for me to do ad reads for Moneywise.
0:13.6	Today's sponsor is a company called Oceans. So it's Oceans Talent.com.
0:18.4	And I was given this script to read and I just said, screw it, I'm just going to tell you
0:22.8	what just happened.
0:23.7	So at my all hands, that just end, about four of the 25 people there, they were people we found
0:30.2	via oceans.
0:31.3	And so offshoring gets a bad rap.
0:34.4	And it gets a bad rap because a lot of people think that the people you hire via offshoreing
0:39.7	firms are low-level talent and do low-level work or they just do stuff that AI is already
0:45.4	replacing.
0:46.5	That is not true at all.
0:48.2	The people who we have who are EAs at our company, they help us with marketing.
0:52.0	They do operations.
0:53.0	And we treat them as fully part of our
0:55.9	team because they are. And I know who they are. And it's just like a regular employee in America.
1:02.4	And what's great about oceans is you can get top talent and finance marketing operations,
1:07.0	basically any role that you're hiring for for only about $3,000, at least that's the
1:11.6	starting point. And you can get amazing, talented people in like two weeks. One of these
1:16.4	folks who worked for us, I think we've got her in like five days, and she's amazing. We've worked
1:21.4	with her for like a year now. And so if you don't want to burn a lot of cash, but you still want
1:25.9	the best high caliber people and you don't want bloat and you don't want to burn a lot of cash, but you still want the best high caliber people
	...

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