Why now
The market is shrinking.
Fewer new buyers are coming into direct-to-consumer wine, so every member you keep matters more.
Nationwide drop in direct-to-consumer wine shipments in 2025, the largest in 17 years of tracking.
Drop in shipments to California residents, the largest destination for Central Coast wine.
Of falling shipment volume nationwide, in a row, with no bottom in sight yet.
Source: 2026 Direct-to-Consumer Wine Shipping Report, SOVOS ShipCompliant and WineBusiness Analytics.
Closer to home
How Paso Robles and Santa Barbara compare.
The Central Coast is falling faster than the nation: the value of wine shipped direct to consumers here dropped 12% in 2025, twice the 6% drop nationwide. In SVB’s regional results, Paso Robles clubs signed up new members more slowly than any other region, and both regions sell less per tasting-room purchase than the national average.
| Measure, 2025 | Paso Robles | Santa Barbara | All regions |
|---|---|---|---|
| New members signed up, as a share of the club | 19%lowest of any region | 22% | 26% |
| Members lost, as a share of the club | 19% | 24% | 22% |
| Net change in club size | Down about 2% | Down about 4% | Down about 2% |
| Average tasting-room purchase | $154 | $140 | $197 |
| Wineries that cut tasting fees | 20% | 9% | 15.5% |
| Direct-to-consumer share of sales | 70% | 62% | 67% |
Sources: SVB 2026 Direct-to-Consumer Wine Report, regional results; SOVOS ShipCompliant 2026 for Central Coast shipments. Paso Robles is about 4% of SVB’s 450 respondents, so treat its figures as directional. San Luis Obispo County wineries outside Paso Robles are counted under “Other California.” Sign-up and loss rates average each winery’s own rates (p. 36); net change works from average member counts (p. 38), so the rows don’t subtract exactly.
What separates the winners
The winners focus on relationships.
“Efficiency is the permission to play. It is not a strategy.”
Rob McMillan, SVB Wine Division
The average lifetime value of one wine club member nationwide, a record high.1 Keeping ten more members a year protects about $28,000 in lifetime value.
Source: SVB 2026 Direct-to-Consumer Wine Report, a survey of 450 family wineries.
1 Average lifetime value of a wine club member across the U.S., from the same SVB report. Your own club’s number depends on your price, shipments, and how long members stay.
Free Wine Club Health Check
How much upside does your club have?
The Health Check scores your club in five areas against what the top-performing wineries do differently, built on the 2026 SVB and SOVOS research. You’ll see right away which of four bands your club falls in, from Back to basics to Relationship-led, and the two areas with the most room to grow. No email needed to see your score. Your full report comes from me personally within one business day.
You probably already know what the top clubs do. The hard part is finding the hours to do it every week. AI fluency is how your club manager does it, with the team and the club software you already have.
Have your owner, your club manager, and anyone else who works on the club take it too. Where you see the club differently is where we start.
Where it helps
Seven places your club gets easier.
Which of these are challenges for you right now? Tap one to see it today, and with AI fluency.
Keeping members
The club release
Beyond the club
The club is where we start.
The skills your club manager builds carry into the rest of the winery. You choose what comes next.
The tasting room
Hire to sell, not just pour.
The tasting room is where members are made. Your staff learn to tell the story and ask, “What would you like to take home?” Then a follow-up invites every guest to join the club.
Marketing
Winners take the brand to the customer.
One set of winemaker notes becomes your email, social posts and web copy, in your voice.
The owner’s desk
Winners hold price and compete on value.
A thinking partner for pricing, planning and the numbers behind them.
The Fluency Flywheel
Your club software holds the data. Your club manager turns it into relationships and revenue.
The AI never talks to a member on its own. Every Monday, your club manager exports a few reports from the club software you already use, and AI turns them into a call list and drafts. Anything worth keeping, like a note from the tasting room, goes back into that same system. It sorts, drafts and suggests. Your club manager decides, signs, calls and pours. Every hour it saves goes back into the conversations that keep members.
Member data stays protected. Your club software stays the one place it lives, and the weekly export goes into your winery’s own AI account, never ours. Before anything else, we agree on what is safe to share with an AI tool and what never leaves your system.
Works with Commerce7, WineDirect, OrderPort and Vinoshipper. No integration and no new software.
How I teach
Learn it on your own work.
I teach the way a trade is taught, and I mean that literally. As Business Liaison for the San Luis Obispo County Office of Education, I co-built the county's registered tech apprenticeship program, and it became one of the most successful of its kind in California. It continues today through SLO Partners. Every skill in the class follows the same three steps.
I show you.
Every new skill starts with me doing it first, on real club work, so you see what good looks like.
We do it together.
Then we do it side by side on your own work, and I catch the small things before they become habits.
You lead it.
Then you run it on your club’s work each week, with me a text away when you get stuck.
“What stood out to me is his ability to translate his experience into a repeatable process that founders can actually execute on their own.”
Now I Can with AI, wine club edition
Your club manager learns beside me.
No new software. One person per winery, the owner in it from the start, and club managers from other wineries learning side by side. Tap a step for the details.
1Before we startPick your club managerShow more
You and I choose who learns, and agree what member data is safe to use with AI. One person per winery, with the owner backing them.
2Weeks 1 to 7Learn beside meShow more
One live session a week with club managers from other wineries. Between sessions, they practice on your own club's work, and we meet one on one every week.
3Week 4The owner sits downShow more
You and I meet to look at what your club manager is building and decide where to point it first.
4Week 8CapstoneShow more
Modeled on the Demo Day that closes Cal Poly's summer startup accelerator. Each club manager presents the plan for their club, with every owner in the room.
590 days afterI stay in itShow more
Alumni meet every other week to compare notes. If you add rollout coaching, our weekly one on one continues for 90 days while your club manager leads the change. I know release week, declined cards and the members who drift, so our time goes to your club, not to explaining it to me.
Who else is in the room
Club managers from other wineries.
Your club manager learns beside people who know release week and the members who drift away. The group compares methods, not numbers: your pricing, sales and member data stay at your winery. Every seat in a wine club cohort goes to a wine club, so nobody spends class time learning what release week means.
What stays private →What they build
See what your club manager brings back.
At Demo Day, each club manager presents a real tool built on your own club's work. After the class, the same skills spread across the winery. Pick an example to see what it does and which weeks it draws on. Tap any week to see what it covers.
The club in these examples has three tiers: Estate Reserve, six bottles with library wines; Vineyard Select, four bottles; and Cellar Discovery, three bottles and the easiest way in. Moving a member down a tier, instead of losing them, is one of the saves you'll see.
See examples of capstones from the 8 weeks · 10 examples
See examples of capstones during the rollout · 10 examples
Examples are illustrative. Names, wines, figures and dates are fictional.
How we prove it
Measured, not promised.
We set a baseline together first. Then you pick the number that matters most to your winery: members kept, new members signed up, or new revenue from members beyond their shipments. We also track the hours it takes to get each release out the door.
Who is teaching this
Dan Weeks
Four years teaching entrepreneurship at Cal Poly, a hundred startup teams mentored, and seven Anthropic certifications in AI fluency.
Full background
I spent twenty-five years at HP and earned five engineering patents. I founded a company and grew it past sixty people before it was acquired. I taught entrepreneurship at Cal Poly for four years, spent thirteen years as Entrepreneur-in-Residence at the SLO HotHouse, and have mentored more than a hundred startup teams. I hold seven Anthropic certifications in AI fluency and work across Claude, Copilot, ChatGPT and Gemini, so what your team learns carries over to whatever you already use.
Testimonials
Students and founders I taught and mentored at Cal Poly, in their own words.
Dan's warmth and genuine positivity made it easy to be honest about where I was struggling. Because of the environment he created, I was quickly open to hearing where we were going wrong, trying new solutions, even if it meant failing along the way, and recognizing when our team needed to pivot. That kind of psychological safety is hard to manufacture, and Dan does it naturally.
My project's success was greatly due to Dan's mentorship. He adapted to our group's learning styles, pulling examples from multidisciplinary studies and pushing us to ideate when we just wanted to settle. His relentless optimism and expertise were instrumental to our success.
I came in with passion but no clear path, and Dan pushed me to turn that into something tangible I could actually test and improve. His perspective and questions gave me the clarity and the process I needed to move forward with confidence.
Having had the privilege of learning from Mr. Weeks, his ability to cut through the noise, challenge assumptions, and drive real results made him an invaluable force behind our progress. Any individual that works with Mr. Weeks may experience the following “side effects”: crystal-clear vision, elevated standards, sharpened decisiveness, and the kind of excitement that comes from his contagious energy. You'll be in exceptionally trustworthy hands and lucky to have him onboard.
Why wine
A sommelier in the family
Wine runs in the family. My son Kyle is a Certified Sommelier who studied under ten Master Sommeliers. I bring the AI and the teaching, and he continues to inspire me about wine.
Hospitality is human.
AI handles the background. You handle the guest. I am talking with a small founding group of wineries now, from family tasting rooms to larger estates. If you run a wine club, I would like to hear what you are seeing.
Moving off WineDirect before it retires on December 31? Build the Monday routine into your new platform from day one.
Or email me at dan@pismopointadvisory.com
