Open with an Exit Strategy
“They are designed to be sold, not remembered.”
That’s Ryan Bean, fellow Substacker of Bean Checks Out, writing about boutique luxury hotels in America. He could be walking through the tasting room of any Napa Cab / RRV Pinot brand launched in the last five years. Hell, the last 10.
The winery polish is there. The origin story is tight (the dream of making wine). The social media is cohesive. But the thing itself, the actual experience of visiting, of drinking wine feels provisional, like a rendering of a life rather than the life itself. It looks like an investment, or worse a trophy, but certainly not a winery.
Bean argues that American luxury hotels suffer from a structural flaw: they’re built for the spreadsheet class from day one. “The system around them—debt, investors, and the expectation of a future sale—isn’t designed to protect what makes them special, it’s designed to extract value from it.”
Sound familiar?
The wine industry has become expert at this extraction. Gallo’s recent acquisitions—Rombauer, Massican, Whiny Baby—represent three different endgames: independent brands folded into larger systems built around distribution and loyalty. What made them distinct becomes something to standardize, replicate, and scale. Smart calls, unique brands, completely different time periods for acquisition.
I’ve made this point before. The acquisition of Whiny Baby by Gallo is akin to Google buying a 5-year-old AI company for the IP. They recognize value, a shift in the marketplace, and innovative talent. They make smart acquisitions.
A less complimentary tone could be said about Treasury Wine Estates and their recent acquisitions and write-downs. The write-down wiped out $676.1 million in goodwill from the Treasury Americas division. Because goodwill is tracked at the overall regional division level, which includes DAOU, Frank Family Vineyards, and Beringer, this represents a broad devaluation of what they previously paid for these US acquisitions.
Bean notes that the best hotels “feel authored because they are, shaped by a continuous point of view, not a set of standards.” But authorship requires patience. And patience is a luxury the current market doesn’t afford. “There is no grace period, no apprenticeship, no room for the hotel to learn itself.”
I feel this acutely in restaurants and wineries. You have to be perfect from day one—Michelin-starred, 98 points, viral—or you’re just another average business with no recognition and no star power. Boring. Pedestrian.
Where’s the slow burn? The story over time?
There is none, because no one is covering the story, no one cares. That long-term story isn’t for social media, a YouTube series, or reality show. “Top Winemaker” is not ever going to be a thing. There is no quick-fire challenge. Instead there’s a 12 month waiting period before our next harvest…stay tuned.
Here in Sonoma County, California, less than 100 miles from Silicon Valley, patience feels to many like inefficiency. And a long story without an obvious exit reads like poor planning on my part. So it makes sense that I’ve lost count of how many times I’ve been asked, “What’s your exit strategy?”
It’s a reasonable question in a reasonable world. But it assumes I built an asset. I didn’t. I built a second career.
Could someone offer me a number tomorrow? Sure. Is it “F’You Money?” If not, then what do I do? Go build another one, optimized from the start for the exit I just took? The premise of my winery didn’t begin with an end. It started simply and has grown incrementally. Constant tactical adjustments to current markets and strategic pivots for long-term viability.
Brands built to be sold are shaped by the exit from inception. And it shows. The polish, the gloss, the socials. Look at celebrity wine brands: branded from Day 1. The underlying product, bulk juice from across California, will fix itself over time, more precise and driven by protocol.
That’s the difference between wine as a memoir and wine as market positioning. One assumes I’ll be there to turn the page. The other assumes the founder will be gone before the story gets interesting.
To re-quote Bean, the best hotels “feel authored because they are.” Authorship implies a controlling intelligence that persists across time. A voice that revises itself, that contradicts earlier chapters, that matures. You can’t author something in a single vintage any more than you can write a memoir in one sitting.
The authored winery accumulates. It keeps barrels for 10 years, not disposing of them because they are ‘used’. The owner changes the label design not because a brand consultant suggested “fresh energy” but because the owner’s taste evolved. These are the edits, the struck-through passages, the margin notes that make a text feel lived-in rather than focus-grouped.
An exit strategy requires a clean manuscript: tight margins, no typos, a clear table of contents, suits at the table. Authorship requires only that you keep showing up to the crush-pad, no suits visible, vintage after vintage, even when the critics aren’t watching and the case sales are flat.
Especially then. Especially now.