The situation
Good wine, a beautiful property, and a business that wasn't working
A family-owned California estate with about $1M in annual revenue. Visitors kept coming. The wine was good. The P&L told a different story, and the owners didn't agree on what to do about it. A generational handoff was also in view, which raised the stakes: whatever got built had to be something the next generation could actually run.
There was also owned production capacity the estate program didn't need, sitting idle with its fixed costs already on the books. That turned out to matter more than anything on the list above.
The process
Build the plan so the owners own it
Most strategic plans fail because they're correct on paper and nobody in the building feels responsible for them. The process was designed against that.
Current state assessment
Ten domains, eight months of financial and operating data. Written as a factual baseline with recommendations deliberately held back, so the owners could react to the facts before anyone pushed them toward an answer.
Independent priority ranking
Each owner ranked the assessment's eight strategic questions on their own. Where they agreed, it confirmed direction. Where they split (one put governance first, another put it seventh), the split went into the plan as a question to resolve in the open.
Owner one-on-ones
Fifty minutes with each owner, each with a different job: the operating read, the market and digital read, the capital read and the end-state intent.
Capital and breakeven model
A stage-gated model built against an honest definition of breakeven, including fair-market rent on the family-owned facility. Every recommendation was tested against three filters before it went in: can this team carry it, does it fit the capital envelope, and are the prerequisites in place.
Draft and independent read
One integrated draft, read by each owner individually before any group discussion, with comments consolidated into a single feedback log.
Ratification session
Three hours, run from the feedback log. Every item left with a decision owner, a revision commitment or an honest "still open." The decisions became the first entries in the plan's decision log.
Inside the roadmap · Excerpt 1
Five horizons, moved by gates instead of dates
A horizon ends when its gates clear. If they clear early, the next one starts early. If they slip, the horizon extends and everyone can see why.
Stabilize and launch
New subscription program live, lifecycle email rebuilt, permanent GM hired, monthly operating cadence running.
Scale and build the book
Subscription through a full annual cycle. Production clients contracted against idle capacity. Advisory seats added.
Steady state and the big decision
Operating at the planned endpoint. The owners decide, with real numbers in hand, whether to fund expansion.
Inheritability cadence
The board rhythm runs without founders in the day-to-day. Channel mix settled.
Inheritable asset
The wine business pays for itself on its own P&L, rent included. Next generation at the board table.
Inside the roadmap · Excerpt 2
One pillar, laid out in full
The plan carries eight pillars, ordered by the owners' own priority ranking. Each one follows the same structure, so a future GM can pick up any pillar and know where to look. This is the club and DTC pillar.
Club, DTC and the subscription move
Pillar 5 of 8Statement of intent
Move from a traditional wine club to a subscription with a rewards ladder that every guest sits on, not just members. Raise retention and lifetime value through benefit design rather than discounts, and keep the member relationship in house.
Where the current model is limited
- Churn near double benchmark, two-thirds of members in the entry tier.
- Thousands of annual visitors leave with no ongoing relationship of any kind.
- Lifecycle automation mostly dormant. One flow was built and never switched on.
- Cancellation reasons unusable, so retention work had nothing to aim at.
The move
Launch directly, timed to the harvest visitor peak, with no test trial. A trial would have delayed revenue by six to nine months to answer a question the launch answers anyway. An invite-only top tier is earned through lifetime value, never sold.
The trigger
Conversion is the leading indicator and gets reviewed monthly from launch. The plan is underwritten at the middle number, not the best one.
Retention protocol
Rebuilt cancellation taxonomy, early-warning signals for at-risk members, a recovery sequence and a script for the service call. The single metric is average member tenure, tracked monthly against a minimum threshold.
Action map
| Year 1 | Year 2 | Year 3 | Year 4 | Year 5 |
|---|---|---|---|---|
| Program launched; six lifecycle flows live; top tier defined; retention protocol running. | Full annual cycle; tier mix shifting up; discount rate normalized to benchmark. | Subscription is the primary recurring revenue line; tenure above target. | Rewards ladder mature; non-member visitors converting at a higher rate. | Subscription has replaced the old club as the core DTC model. |
Owners
Fractional leadership through launch; operations manager on execution; outside DTC partner on systems; GM owns the pillar once seated.
Inside the roadmap · Excerpt 3
Who decides what
Family businesses tend to run on informal agreements that work right up until they don't. The decision-rights matrix writes them down.
| Decision | Authority |
|---|---|
| Capital above a set threshold | Ownership |
| Entity changes; brand position | Ownership |
| Senior hires (GM, head winemaker) | Ownership with GM input once seated |
| Direction at each horizon gate | Ownership on GM or advisor recommendation |
| Day-to-day operations; hiring below senior level | GM |
| Vendor contracts within budget; pricing within the architecture | GM |
| Execution against an approved pillar plan | Functional lead |
Every material decision gets three answers: who decides, who is consulted, who is informed.
A risk register row
Each risk carries the trigger that forces a re-plan, so nobody has to debate whether things have gone wrong.
| Risk | Why it matters | Trigger and response |
|---|---|---|
| Subscription converts below plan | Largest single revenue lever in the model. A miss here moves breakeven out of the planning horizon. | Below the plan anchor for two straight quarters, or below the floor in any quarter: architecture review within one quarter. Three options on the table: escalate effort, change the architecture, or reforecast downward. |
The decision log
Written for whoever runs the business in five years. They should be able to read why each call was made, not only what it was.
| Entry | Decision | Rationale and alternatives | Owner |
|---|---|---|---|
| DL-001 | Launch subscription directly, no trial. | Trial delays revenue two to three quarters. Rejected: phased pilot. | Ownership |
| DL-006 | Breakeven includes fair-market rent on the owned facility. | The business has to stand on its own. Rejected: rent-free view. | Ownership |
| DL-010 | Expansion capital held as a Year 3 owner decision, not a plan default. | Payback and complexity differ in kind from earlier tiers. Rejected: pre-committing in Year 1. | Ownership |
Illustrative entries, paraphrased from the real log.
The capital story
No dollar goes in ahead of demand
The idle production capacity became the largest lever in the plan, through contract production for small producers. Capital to open it up was split into three tiers, each released only when booked volume proved the demand.
Tier 1
Tanks
- Size
- 1.0x
- Payback
- 0.9 yrs
Released when contracted volume repays it within three years.
Tier 2
Targeted fit-out
- Size
- 1.4x
- Payback
- 0.6 yrs
Released when the first tier's capacity is more than 70% booked.
Tier 3
Facility expansion
- Size
- 7.1x
- Payback
- 3.0 yrs
Not committed. Evaluated by the owners in Year 3 if capacity is more than 80% booked. On base-case numbers it covers only about three-quarters of its own annual cost.
Telling the owners the smaller number
The model's best case looked good. Then we loaded the costs it hadn't carried: inflation on overhead and the new compensation plan. The upside shrank by more than a third, and the plan was underwritten at the middle case instead, which comes in at under a fifth of the original headline.
Year 5 operating result, indexed to the headline case = 100.
One more number the owners needed to see plainly: the peak cash need lands in Year 3 and is nearly three times the five-year cumulative deficit. The trough is the real capital ask, so the plan says so.
Working together
If this looks like your business
Most of the estates I work with don't have a wine problem. They have an operating chassis problem, and usually a few conversations the family hasn't had yet. The work starts with an honest baseline and ends with a plan your team can run without me in the room.
If you'd like to talk through where your business sits, I'm at tony@trueorigincollective.com
Tony McClung
Founder, True Origin Collective