Have you been to Whiskey Dix?
From AI Dreams to Real Wins
Located an hour outside of Madison, Wisconsin, the salon features two naked ladies above its entrance, staring across at a church. Frequented by local families of famers and accountants, as well as pass-through biker gangs, the place is a spectacle. An old car floats in mid-air, the bar counter is covered in pennies, multiple bartenders poor drinks faster than you can imagine. Outside, bright blue sky, sunshine, and punk rock music blasting for miles away.
This isn’t a wild dream, it’s a real saloon that my friend Billy owns in rural Wisconsin. Billy isn’t your typical barkeep tho. He’s got a good eye for business, and would outwork anyone when it’s time to roll up the sleeves. He’s the kind of guy that once handed me a rifle with a fresh deer blood on it, and at the same time he’s also one of the very few blue collar guys who is actively exploring how AI could grow his business. He’s already using ChatGPT to write emails and newsletters and to create marketing materials for events, but he is also looking to do more.
Billy and I spent an hour last week chatting about his saloon, to see how he could use modern AI to grow the business. He was stoked to find out about CafeX and a Robotic Bartender and a number of offerings like that, already deployed around the world; they could one day replace or augment his staff. He thinks it would be dope to do outbound sales by making AI robocalls to every house in the county. He was even receptive to the idea of using video feeds to personalize experience for his patrons.
The longer we talked though, the more I wondered if AI’s grand promise fits a rural Wisconsin saloon just yet. Maybe we’re not thinking big enough, or maybe the latest tech isn’t the answer right now. I suggested he chat with Grok daily about bar stuff to let it soak up his ideas, but I couldn’t pin down an AI trick to 10x his business overnight.
I did, however, think of a couple practical moves to boost revenue today. Somewhere in the conversation we dug up what makes Whiskey Dix tick—its killer concert weekends, packing the bar with hundreds of loyal locals and rowdy visitors. What he should do, in my view, if to squeeze more cash out of those weekends.
Billy got a long google doc out of me, but here are the top 3 suggestions:
Figure out which drinks make the most profit per minute—high-margin or fast pours—and optimize to push those during concerts. Someone might be annoyed at not getting their favorite drink, but as long as the majority buy more at higher margins, Billy makes more money. Money money means more concerns, happier staff, and thus more repeat clients.
Create a VIP program. Sell a $100 annual pass with perks like a free drink per visit or skipping the concert line. Make VIPs feel like rockstars and notify them first about events. Have these guys pay to become so passionate about the bar, they become the influencers that bring in the crowds, for free. Also, put extra cash in the bank, up front.
Stick one bartender on VIPs and big spenders (think premium drink orders) for fast, personal service. Call it a perk they can buy into. Paired with the first two recommendations, this boosts revenues even further.
My bonus suggestion was to create a Punch Card experience, a loyalty program tailored to the more humble visitors. Offer it such that points need to be collected during week days, but redeemed on the weekends. “Buy five drinks, get one free at the concert” —low-key loyalty to nudge locals coming at the times when the bar is open and idling, with a reward for also supporting him on the busy days.
The Bottom Line
While I am generally super stocked about AI solutions, sometimes AI’s like that rifle Billy handed me—still warm with deer blood. It’s powerful, it’s slick, and yeah, it can do some wild shit. But if your goal isn’t to knock down a deer, the rifle isn’t good for much else. All my suggestions to Billy didn’t need any fancy technology, just a few process updates, and a will to try.
Billy’s already got AI to stamp out emails, newsletters, and promo stuff for Whiskey Dix. Hell, I bet he’s already doing the ROI calculation on the robotic bartenders too. It’s tempting to think that AI is the golden ticket to blow this saloon up.
Maybe it isn’t though; maybe shiny algorithms and the promise of AGI isn’t the way forward. Whiskey Dix is a bar; it’s a spectacle—and he just needs to lean into what it is: push high-profit pours, build a VIP group to hype the joint for free, and staple a punch card to the regulars to keep ‘em coming back.
What do YOU think?
If you’ve ever slung drinks or owned a bar, or perhaps you’ve spent one too many night at a place like that, we would love to hear your two cents. What’s worked for you? Is AI the solution to everything, or is there still some room for human ingenuity?
Drop it in the comments or send me an email. Let’s pool some real-world brilliance and help Billy crank this punk rock saloon to eleven. Let’s make sure they can hear it all the way from Madison!
— Kirill.
