Passive Loss Advantages 1031 Exchange Mechanics AVA Valuations Deal Anatomy Water Rights Operator Intelligence Distress Signal Research Custom Crush Economics Passive Loss Advantages 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 accredited investors the inside view on an asset class most people talk about but few actually understand.

"The passive loss rules on vineyard investments can shelter income most CPAs don't know is sheltering-eligible."
— 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
Passive loss advantages, 1031 mechanics, depreciation schedules on improvements. The things your CPA hasn't flagged because they've never been inside a vineyard deal.
🔍
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
The tax math for putting $500K into a vineyard vs. a REIT. Why athletes at peak earning years are the ideal vineyard investor. What family offices consistently 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
The passive loss rule your CPA probably hasn't mentioned
For a vineyard structured as an operating business, an investor who meets the material participation tests can treat vineyard losses as ordinary deductions — offsetting income from any source. For someone in the 37% bracket, on a $2M investment generating $200K/year in Year 1–4 losses, that's $74,000 annually in tax savings before depreciation...
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 this interesting: the prior buyers had missed a 1031 solution on the seller's side...
What I'm Watching
Mendocino AVA pricing · DTC license changes · Water adjudication in Napa

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  • Full deal breakdowns every issue — structure, price, tax outcome
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  • Market signals and distress deal flow previews
  • AVA-level pricing data and valuation analysis
  • Tax strategy deep dives with real numbers
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