OP #305: Big Sky Is the New Palm Beach

How crypto wealth, Swiss tariffs, and private jets are redrawing the luxury map.

Author

Darren Herman
August 05, 2025

As you’re reading this, I’m en route to Dallas for a quick trip to Fogo de Chão HQ. Might even sneak in a Yankees vs. Rangers game while I’m there. I’m a Yankees fan, and it takes me to go to Dallas to see my first Yankees game in 1-2 years. I’m way overdue for a Mavs game with some other friends in Dallas so may be a good sporting year while I am down there.

Lately, I’ve been thinking a lot about new money. Maybe it’s because I just got back from Palm Beach, which—let’s be honest—is the opposite of that. (And for the record, I’ve got nothing against old money.) But it reminded me of something I wrote in an OP years ago: crypto won’t truly go mainstream until you can spend it on real things, in real life. That moment is arriving. With recent moves from PayPal and others, we’re not far from crypto—trillions of it -flowing into the economy in ways that reshape how wealth is created, signaled, and spent. Note: new money isn’t just crypto, but there is a lot of new money in crypto.

This week’s OP is a slight departure from the usual tactical fare. Less about pipeline meetings, more about mindset. A strategic lens on what this emerging class of consumers means for operators like us—and how to build for a future where new money moves very differently… we think, so far.

And as many of you will ask me in 1:1 emails, I do own crypto, but not anywhere close to a significant portion of wealth. I had a bunch which I purchased and sold at $400/coin and $1600/coin, but wow, I wish I had held onto those! I do not subscribe to the HODL philosophy and I’ve been brought up having learned the pigs get fat and hogs get slaughtered mentality. If I can bank a great win, I will, and usually do not hold out for future potential. And it’s been that thinking that I’ve missed some incredible wealth generation. Still, I’m not complaining and have entered back into the space with a combination of direct ownership as well as ETF exposure over the past couple of years.

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Thanks again for subscribing to the OP. This will be the last OP until after Labor Day due to my typical end-of-summer siesta. Hang in there, I’ll be back. And yes, the content of this OP will throw you a curve ball from the regular content… but is that such a bad thing?

Darren

Time, Tariffs, and Tastes

Over dinner in Palm Beach recently, a friend unveiled a Patek Philippe 5270P with a salmon dial that practically glowed. He paid for it using realized gains from Solana. Crypto meets haute horlogerie. It’s becoming a thing. Don’t believe me? Look at this data (Bloomberg).

This sparks two big questions:

1. What happens to the luxury watch market now that the U.S. is imposing a 39% tariff on Swiss imports?
As of August 7, 2025, tariffs on Swiss goods jump from 10% to 39%—well above other global rates, and nearly double prior proposals. The U.S., which accounted for $5.4 billion (≈16–17%) of Swiss watch exports in 2024, is the industry’s lifeblood. Jefferies projects U.S. retail prices could rise 20%+ immediately after Rolex already raised prices this year.

2. What does crypto wealth want—and where does it put its bets?

Over the past ~18 months, Bitcoin surged ~150%, fueled by the January 2024 ETF approval and the latest halving. Crypto markets reached ~$3.8 trillion in late 2024 before retreating slightly in early 2025. Even with macro headwinds, major tokens like Ethereum and Solana doubled or tripled.

Meanwhile, the private jet industry is roaring back. Private-jet departures in early 2025 were up 3–6% year-over-year, with Florida-specific departures jumping 11% YoY in February. NetJets received its 50th new jet of the year in 2024—roughly a $1.3 billion fleet expansion—and secured purchase rights for another 1,500 jets starting in 2025. Brokers report a ~20% YoY increase in on-demand charter bookings.

What ties these threads together? Some of it is a young, self‑made class of crypto-native wealth that's not just banked—it's spending. Their expenditures signal something new.

Core Insight: Wealth in Motion

  • Crypto’s returns: Bitcoin’s ~150% gain in under 18 months is emblematic of a liquidity event that traditional luxury markets haven’t seen in a decade.

  • Watch brands vs. policy shock: The 39% tariff will raise U.S. retail prices on Swiss watches by at least 20%, pushing buyers toward secondary markets and pre-owned options.

  • Jets as lifestyle, not trophy assets: Demand for fractional ownership and charter hours is rising, and new crypto holders are increasingly booking—and investing in—private aviation.

If You’re Building or Investing Right Now…

Think of this as a cultural and monetary shift—not just a cyclical bump.

  • Pricing needs to reflect volatility. Traditional MSRP models are vulnerable. Brands or platforms that incorporate dynamic, peer-based pricing will outperform.

  • Deliver at scale, flexibly yet immediately. Private jet fractional and card models are thriving. Expect similar preferences across luxury cars, real estate, and even boats.

  • Craft new stories. Heritage is great—until you're competing with narratives spun on X, Discord, and TikTok. Crypto wealth wants cool, not old.

  • Geo is product. If you're targeting crypto spenders, focus past Palm Beach: think Jackson Hole, Big Sky, Scottsdale, Bozeman. These locations align with lifestyle and spend behavior.

So What?

If you’re still building the same product framed for Fifth Avenue customers, you're missing where money—and its expression—is headed.

Palm Beach will get its share. But Jackson Hole, Bozeman, and Big Sky might define new high-net-worth zip codes.

The same way that AI is rewriting how we think about computers and output, wealth generation and spending is evolving as well…

7x Return: Meme Coins

Below is a screenshot of the market cap of meme coins per coinmarketcap.com. If you had bought this basket of meme coins over the past year, you’d see an 83% appreciation. If you had it over the past 30 days, you’d have seen 26% appreciation.

I never really paid attention to meme coins, often poo-pooing them as instruments. I dabbled a few years ago but didn’t keep any.

Just looking at the performance data, who is the fool?

With that said, the risk associated is real. The S&P500 returned 15% in the last 12 months. Is it worth taking the meme-coin risk for 7x return? To each their own…

What’s more interesting to me about the meme coins than the financial components are the cultural movements and consumerism that is driving them. Sure, a ton of it is manipulated (I think?) but lots of retail investors are behind these…

I do not often write about crypto and meme coins but figured I’d share in this OP for something a bit different…

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

The Consulting Crash Is Coming (The Free Press) h/t Auren Hoffman

The AI Metric: $ / MWh (Albert Wenger)

Thanks again for subscribing to the OP! If you were forwarded this letter and want to subscribe, you can do so here.

Darren

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