Software the business actually operates on — bookings, payments, daily operations — assembled per owner in days, not years. One platform, configured to each business by AI and a small Holler team, so the hundredth owner goes live as fast as the first. Below is one moment on it: the dashboard handling a real after-hours inquiry from a winery in the Rappahannock corridor. Click through it.
HOLLER/ old-rappahannock
SUN · 10:47 PM
Quiet line. The next call shows up here.
BETWEEN PHONE CALLS, IT RUNS THE BUSINESS
The same platform handles the work that doesn’t announce itself — outreach, inventory, staffing, logistics, payments, the next sale.
Automated outreach
Reaches the right forty customers on a Tuesday morning.
Wednesday’s tasting has six open seats. Holler segments by who came last spring, who bought Cab Franc, and who lives within forty minutes — then sends each one a note in the owner’s voice.
Inventory
Knows the Petit Manseng case is down to nine bottles.
Pours per shift run against the cellar count. When a varietal drops below the reorder line, Holler pings the owner and drafts the call to the distributor — already on the right account.
Staffing
Builds Friday’s schedule before the owner asks.
Reservations, expected walk-ins from the app, and last weekend’s labor hours go in. A draft comes back — front of house, kitchen, tasting room — sized to the night, not last quarter’s average.
Logistics
Routes Thursday’s wholesale run without a phone tree.
Three restaurants ordered. Holler sequences the run by neighborhood, prints the BOLs, and texts each chef their ETA window — with extra slack for the one that always changes the count last.
Payments
Closes the tab and the books at the same time.
Card runs through the same surface as the booking. Tips go to the right server, sales tax sorts itself, and the deposit clears before the next morning’s reconciliation — no separate POS to babysit.
Up-selling
Offers the wine club to the right table, at the right moment.
The couple at table four bought two bottles to go. Holler suggests spring club enrollment with the next-shipment preview — only to guests who fit, only when they’re ready to say yes.
6 more — scroll
The demand engine
The fill-it engine.
The Rappahannock app sends customers into the businesses that run on Holler. It surfaces what’s open, what’s full, and who’s pouring tonight; the Inn at Little Washington puts it in every guest room so weekend planning starts before check-out. This is the half competitors don’t have.
>40%
App Store visit-to-install rate, with zero paid acquisition. The kind of pull-through that’s hard to fake on the demand side.
12:17
RAPPAHANNOCK
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Why
The stack that doesn’t fit.
A winery owner runs the place on seven different tools — a calendar, a POS, a mailing list, an OpenTable account, a spreadsheet the accountant set up, an inbox, the phone. Each one charges every month. None of them know each other. The owner is the integration. The couple who came last spring, paid by card, joined the list, and asked about the wedding venue lives in seven different systems — or, more often, in nobody’s memory at all.
The owner can’t afford to glue it together and won’t hire someone to do it. So the stack itself becomes the tax — paid every month, in fees and in revenue the place never sees.
Holler is what shows up when the stack is one platform, configured for the place. The booking, the deposit, the cellar count, the schedule, the regular’s name — one system with the full picture. And once the picture is whole, the software starts to earn: the slow Tuesday gets the right text on Sunday, the lapsed regular gets a real reason to come back, the table that just ordered two bottles gets offered the club at the right moment. The old stack only charged. This one earns.
Investors
A small round, almost full.
We’re raising a pre-seed round on a modest cap and onboarding the first paying owners along one rural corridor. The numbers, the model, and the cap table are in the data room.