Tax & Structure 1031 Exchange Mechanics AVA Valuations Deal Anatomy Water Rights Operator Intelligence Distress Signal Research Custom Crush Economics Tax & Structure 1031 Exchange Mechanics AVA Valuations Deal Anatomy Water Rights Operator Intelligence Distress Signal Research Custom Crush Economics
About This Letter

Written from
inside the deals.

Vineyard investing sits at the intersection of agriculture, real estate, tax law, and luxury — which means most financial advisors have surface-level knowledge at best, and most wine industry content is written by people who've never structured a deal.

I run a vineyard-focused investment firm and a custom crush operation based in Napa Valley. Between the two, I sit at a rare intersection: I understand what investors are looking for, and I understand what actually happens inside the operations.

Vine & Yield is where I share that intelligence. Not a pitch. Not a wine club. A bi-weekly letter that gives readers the inside view on an asset class most people talk about but few actually understand.

"The gap between what a vineyard costs and what it's worth is almost always a gap in information."
— From Issue No. 001
Vineyard Investment Firm — Napa Valley
Custom Crush Operations — Napa Valley
200+ active industry clients
55+ years in wine operations & investing
What You'll Learn

Five topics.
One asset class.

📊
Tax & Structure
How vineyard ownership actually interacts with the tax code — 1031 mechanics, depreciation on improvements, material-participation questions, and where the real structuring decisions get made. Grounded in how these deals are actually built, not tax advice.
🔍
Deal Anatomy
Inside real (often anonymized) transactions — from LOI to close. What the buyer got right, what nearly killed the deal, and what the numbers looked like.
📍
Market Intelligence
Which AVAs are undervalued and why. How Napa and Sonoma land prices are moving. What wildfire risk, water rights, and climate shift are doing to valuations.
🍇
Operator Intelligence
What custom crush operators actually charge. How to evaluate vineyard management companies. The 3PL landscape in Napa — from someone running operations inside it.
👤
Investor Profiles
How different buyers approach the same asset — a vineyard vs. a REIT, why peak-earning professionals and family offices keep circling wine country, and what each tends to miss.
Every two weeks
Every subscriber gets the full deal breakdown
Sample Issue

See what the
letter reads like.

Vine & Yield
Issue No. 001
February 2026
The Angle
What 2025's grape prices are actually saying
Napa's 2025 grape prices fell across most varieties, with Cabernet down to about $8,933/ton — a second straight annual decline from the 2023 peak. Meanwhile the cost side is climbing: a new $98.74/acre groundwater fee, and Cal Poly putting regulatory cost alone near $1,745/acre on a large operation. A soft market isn't automatically a cheap one...
The Deal
A $2.8M Sonoma acquisition — what the LOI said and what actually happened
The property had been on the market for 11 months. Two prior buyers had fallen out of contract — one on financing, one on a water rights issue that should have been caught in week-one diligence. What made it interesting was how much of the value turned on things that never showed up in the listing...
What I'm Watching
Mendocino AVA pricing · DTC license changes · Water adjudication in Napa

Every issue.
No paywall.

Every subscriber gets the full letter — market reads, deal breakdowns, operator intelligence, and the occasional structuring note. No tiers. No upsells.

  • Full deal breakdowns every issue — structure, price, outcome
  • Operator intelligence reports from active Napa contacts
  • Market signals and distress deal flow previews
  • AVA-level pricing data and valuation analysis
  • Structuring & tax notes grounded in real deals
Subscribe Free →
What You Get

Everything.
Every issue. Free.

Every Subscriber
$0
Free forever · No tiers · No upsells
  • ✓ Bi-weekly newsletter
  • ✓ Full deal breakdowns
  • ✓ Structuring & tax notes
  • ✓ Market intelligence & AVA data
  • ✓ Operator intelligence reports
  • ✓ Deal flow previews
  • ✓ Investor profiles & case studies
  • ✓ Trend analysis & signals
Start Here
Free to start.
Impossible to unlearn.

Join the readers getting the inside view on vineyard investing. No pitch. Just intelligence.

Free. No spam, ever.