Mar 21, 2025 · 22m · tbpn

Preston Holland talks Jets, Clients, and the Future of Private Aviation.

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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions

Aviation specialist Preston Holland joins the podcast to provide an insider's look into private aviation, discussing aircraft selection, macroeconomic trends, passenger connectivity, and autonomous flight technology.

Chapters · click to jump

3 statements ▾

Holland: Gulfstream G650ER market is far more liquid than BBJ market open →

Holland: Boeing Business Jets average roughly 450 days on market open →

Holland: The US has more airports than Chipotle locations open →

2 statements ▾

Holland: 100% bonus depreciation yields ~20% of aircraft purchase price in tax savings open →

Holland: 100% bonus depreciation passage in Congress is expected 'any day now' open →

3 statements ▾

Holland: Starlink is gaining private jet market share faster than rivals open →

Holland: Starlink equipment installation costs $150k to $350k per jet open →

Holland: Starlink charges $10k/month for aircraft flying over 300 mph open →

2 statements ▾

Holland: VistaJet's $600M raise fell below earlier $1B target open →

Holland: Public markets fail to grasp volatile private aviation economics open →

1 statement ▾

Holland: Sovereign wealth funds back flying cars as US VCs retreat open →

How this conversation actually went

Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →

The hosts as informed peer 5.0 Guest teaching 6.3 Guest disagreement 1.0 The hosts pushing back 1.3

speaking balance: gold is the hosts, purple is the guest (3 minute bins)

Sharpest disagreement ▶ 7:16 Contrasting political stances on aviation loopholes

In a very amicable episode, Preston provides a contrarian political framing, highlighting how Trump championed jet write-offs in contrast to administration efforts to close corporate jet tax loopholes.

Hardest push from the hosts ▶ 14:31 Trophy asset competition distorting earnings

The host challenges the standard business case by arguing that wealthy owners treating jets as break-even hobby assets ruins operating margins for genuine commercial enterprises.

Biggest teaching moment ▶ 9:20 Starlink private jet installation and tier economics

Preston gives a detailed breakdown of the $150k-$350k hardware installation costs and the speed-dependent subscription model differentiating sub-300mph and high-speed flight.

The host holds their own ▶ 16:35 Host explains deterministic software regulatory hurdles

The host displays deep domain understanding by explaining the legal barrier against non-deterministic AI in cockpits and how developers use human-in-the-loop tablet interfaces to bypass it.

the scores for every segment, with the reasoning behind each

Topic	The hosts as informed peer	Guest teaching	Guest disagreement	The hosts pushing back	Why
Gulfstream G650ER vs. BBJ and Airport Accessibility	6	4	1	1	The host demonstrates strong baseline industry knowledge by laying out the runway length constraints of BBJs compared to Gulfstreams for executive offsites. Preston validates this point and expands on it with airport statistics in a collaborative tone.
Macro Trends in Private Aviation and 100% Bonus Depreciation	3	8	1	1	Preston educates the hosts extensively on macro trends, explaining post-COVID private aviation normalization, fractional market growth, and the detailed tax mechanics of 100% bonus depreciation.
Adoption and Economics of Starlink on Private Jets	5	7	1	2	The host asks smart questions about why VC models struggle in aviation and introduces the trophy-asset dynamic. Preston details the unit economics, debt restructuring, and fleet depreciation hurdles facing operators like VistaJet.
Aviation Automation, Regulatory Barriers, and Autonomous Systems	6	6	1	1	The host demonstrates technical knowledge regarding non-deterministic software regulations in military flight control. Preston complements this by detailing civilian safety systems like Garmin Autoland and Skyryse fly-by-wire envelopes.

Statements from this episode (11)

Opinion

Holland: Gulfstream G650ER market is far more liquid than BBJ market

“If you're going BBJ or six 50 ER, personally, I'm going six 50 ER for the sole reason. The market is far more liquid.”

Preston Holland Mar 21, 2025 ▶ 0:38

Assertion Partly supported

Holland: Boeing Business Jets average roughly 450 days on market

“I think the absorption rate is something like 450 days on market is the average, because you have to think you have Grant Cardone and Saudi princes.”

Preston Holland Mar 21, 2025 ▶ 0:49

Assertion Supported

Holland: The US has more airports than Chipotle locations

“There's more airports than Chipotle's in the United States.”

Preston Holland Mar 21, 2025 ▶ 2:04

Assertion Supported

Holland: 100% bonus depreciation yields ~20% of aircraft purchase price in tax savings

“So what it ends up doing kind of when you do, do the math is it's about 20% of your purchase price that you get in tax savings in that first year.”

Preston Holland Mar 21, 2025 ▶ 5:48

Prediction Not checkable as stated

Holland: 100% bonus depreciation passage in Congress is expected 'any day now'

“I don't know exactly when kind of what I'm hearing from some of my clients is they're anticipating, you know, one of those any day now type things from what they're hearing in Washington. So I think it's any day now.”

Preston Holland Mar 21, 2025 ▶ 8:09

Assertion Supported

Holland: Starlink is gaining private jet market share faster than rivals

“Starlink is gobbling up market share, but as a percentage of the overall fleet installation base, it's still pretty small. I don't know exactly off the top of my head what the, what kind of the percentage penetration is, but it's growing faster than any of the…”

Preston Holland Mar 21, 2025 ▶ 8:40

Assertion Supported

Holland: Starlink equipment installation costs $150k to $350k per jet

“It's anywhere from 150 to 350,000 dollars to install the equipment.”

Preston Holland Mar 21, 2025 ▶ 9:32

Assertion Supported

Holland: Starlink charges $10k/month for aircraft flying over 300 mph

“So if you go under 300 miles an hour, it's like 200 bucks a month, and if you go over that, it's like 10,000 a month, so it's pretty significantly different.”

Preston Holland Mar 21, 2025 ▶ 9:53

Assertion Supported

Holland: VistaJet's $600M raise fell below earlier $1B target

“VistaJet just announced a six hundred million dollar fundraise which interesting enough, that's actually down off of the original leak came in the fall, where it's going to be around a billion dollars, and then come February, it was going to be eight hundred m…”

Preston Holland Mar 21, 2025 ▶ 11:16

Insight

Holland: Public markets fail to grasp volatile private aviation economics

“Companies in private aviation that have gone public have, you know, tended to struggle because Retail investors and institutional investors do not understand this space because they don't understand the cost of the fuel fluctuation costs and the engine mainten…”

Preston Holland Mar 21, 2025 ▶ 13:56

Assertion Supported

Holland: Sovereign wealth funds back flying cars as US VCs retreat

“There's been a lot of carnage in the flying car space recently. I mean, it seems like almost every week somebody can't raise another fund. There's a lot of movement actually going to Dubai now in that sector. So, so the sovereign wealth funds are starting to p…”

Preston Holland Mar 21, 2025 ▶ 20:30

Preston Holland talks Jets, Clients, and the Future of Private Aviation.

How this conversation actually went

Statements from this episode (11)

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