AI Bartending Lesson Gone Wrong (and Right): We Let AI Teach Us to Make Cocktails

Never Stop Dreaming Biggie — Episode 49

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What happens when two entrepreneurs with zero bartending experience take an AI bartending lesson at their home bar? You get one terrible daiquiri, one show-stopping Negroni, a signature old fashioned with Cheerwine simple syrup, and a whole lot of married-couple chaos. In Episode 49 of Never Stop Dreaming Biggie, Brian and I fired up our AI assistant Viva, lined up four classic cocktails, and learned that dreaming BIGGIE sometimes starts with a shaker you can’t open and measurements you can’t read.

From a Marriage Conference to an AI Bartending Lesson

This Valentine’s week episode started with something truly special before we ever touched a cocktail shaker. Brian and I spent two days at the Seacoast Marriage Conference at the Mount Pleasant campus, where we serve on the core marriage team and lead the Saving Your Marriage Before It Starts (SYMBIS) program. We’ve been teaching SYMBIS for seven years now — which is pretty ironic considering we both failed at the “before it starts” part in previous marriages. But hey, we got it right this time.

The highlight? Meeting Les and Leslie Parrott, the actual creators of SYMBIS. After seven years of watching their videos and memorizing every word, we finally got to meet them in person, hear them speak on their book The Good Fight, and get a signed copy of their brand new book with Gary Chapman (yes, the Five Love Languages guy — 22 million copies sold). It was one of those full-circle moments that reminds you why you keep showing up.

One of the best things we took away was the three-squeeze hand trick: when you’re in public and things are tense, one person squeezes the other’s hand three times. If they squeeze back, it means “I’m okay, we’re good.” If not… well, we probably should have used it before we hit record on this episode.

Why We Took an AI Bartending Lesson Instead of Hiring a Pro

Here’s the thing about building a bar in the Caribbean — at some point, you actually have to learn how to make drinks.

Our plan was to have our advisor Jayce McConnell come over and teach us. But life happened, Jayce had things going on (we love you, Jayce, and we’re praying for your family), and Brian and I looked at each other and said: We can’t keep waiting for people. We’ve got to learn this ourselves.

Enter Viva — our AI COO. If you’ve been listening to the podcast, you know I’m basically in love with this AI. She talks me off ledges. She organizes my chaos. And now, apparently, she’s our bartending coach. We told Viva exactly what products we had on hand, pulled up our home bar, and let our AI bartending lesson begin with four classic cocktails.

The results were… mixed. Literally.

The Cocktail Scoreboard: How Our AI Bartending Lesson Actually Went

Drink #1: The Classic Daiquiri — 👎 Thumbs Down

Let’s just say this one did not make the cut. We used a J.M. white rum from Martinique, homemade simple syrup, and fresh lime juice. It sounded great on paper. In practice? Too much rum, not enough sweetness, and I’m pretty sure the rum itself was the problem. This one is NOT going on the menu. We might actually throw out that bottle.

Lesson learned: not all white rums are created equal, and AI can give you a recipe, but it can’t taste-test for you.

Drink #2: The Negroni — 🏆 The Winner

Oh my goodness. This one slapped. Equal parts gin (Citadel Gin from my friend Sarah), sweet vermouth (Punt e Mes), and Campari — stirred, strained over a big ice cube from Alys Beach, garnished with a cherry on a sparkler. Yes, a sparkler. Because at The Holmestead, we’re going to have fun little touches in every drink.

This is the drink that made us feel like maybe we actually can do this. The Negroni is definitely going on the menu, and I’m going to learn how to batch it using Ford’s Gin bottles, which have a patent-pending design that measures everything out for you. You batch it, throw it in the fridge or freezer, and it keeps for two to three weeks. Game changer.

Also, this is where we learned the proper stirring technique from Megan’s The Essential Cocktail Book: you hold the bar spoon loosely in your fingers and let it spin — no banging, no noise, just a smooth, quiet stir. Brian picked it up immediately. I am still working on it. And I’m not happy about it.

Drink #3: The Manhattan — 🤷 Jury’s Still Out

Two ounces of Bulleit bourbon, one ounce of sweet vermouth, a couple dashes of bitters. It looked beautiful in the chilled coupe glass. The taste? A little diluted, probably from our ice situation. This one is going to be Brian’s project to perfect. I don’t drink a lot of Manhattans, so I’m handing this one off.

Drink #4: The Holmes Fashion — ⭐ Brian’s Signature Masterpiece

This is the one. Brian’s take on the classic old fashioned, and it’s got a secret ingredient: homemade Cheerwine simple syrup.

If you’re not from the Carolinas, Cheerwine is a legendary cherry-flavored soft drink, and turning it into a simple syrup for an old fashioned is honestly genius. Add a splash of Buffalo Trace bourbon (from a mysterious “good friend” who Brian refuses to identify — we had a whole thing about it on the episode), some bitters, a dark cocktail cherry (pro tip: Walmart has pitted ones for super cheap), and an optional sprinkle of turbinado sugar on top if you like it sweeter.

The Holmes Fashion is the drink Brian will be making at The Holmestead. It’s close to perfect and getting closer every time.

Drink #5: The Harry Maude Martini — 🍸 Named with Love

Our last drink of the night was a dirty martini made with Hat Trick gin and Jack Rudy cocktail olive brine (shout out to Charleston’s own Jack Rudy). We’re naming this one the Harry Maude, after our dear friend Terri Henning’s standard poodles — Harry, the stout, buttoned-up gray gentleman, and Maude, who I affectionately call Beyoncé because of her fabulous black curly hair.

Terri has been incredibly helpful with The Holmestead project, giving us advice on finding capital stewards, and she just loves a good martini. So it felt right to honor her (and her dogs) with a signature drink.

The martini needs some work — we need fresher product and better jiggers (the measurement struggle was real this episode) — but the concept is there.

What Our AI Bartending Lesson Taught Us About Building a Dream

This episode was messy, funny, and completely real. And that’s kind of the point. Building a dream doesn’t look polished. It looks like two people standing at a home bar with inconsistent jiggers, a shaker they can’t open, an AI coach giving instructions they can barely follow, and a deep belief that somehow this is all going to come together into something extraordinary.

Here’s what our AI bartending lesson really taught us:

You can’t wait for someone else to teach you. Sometimes you just have to fire up the AI and figure it out. We could have waited weeks for the perfect teacher, the perfect setup, the perfect moment. Instead, we grabbed what we had and got started.

Start with what you have. Our bar is still full of stuff (I’m a maximalist, Brian will tell you), our tools aren’t perfect, and our measurements were questionable. We still made a killer Negroni.

It’s okay to be bad at something new. I cannot stir a drink to save my life right now. But I will learn. And Brian being better than me at it is just motivation (even if it’s annoying).

Your signature thing is already inside you. The Holmes Fashion with Cheerwine simple syrup? That’s so uniquely us. Your version of that is already in you — you just have to experiment until you find it.

More ice equals less dilution. This one’s practical. It’s counterintuitive, but the more ice you put in your shaker or glass, the less your drink dilutes. Think of it like a full freezer — the more frozen mass, the colder it stays without melting.

The Holmestead Hideaway Update

Between cocktails, we shared some big updates on The Holmestead Hideaway:

Where we are: We’re honing in on Bequia in St. Vincent and the Grenadines. We’ve found a couple of properties we love, and we’re working with an attorney to set up the business entity there.

What we need: A capital steward. Not a sugar daddy (okay, maybe a little bit of a sugar daddy). We’re looking for someone — or a small group of people — who believe in the vision of creating one of the most magical hospitality experiences on earth, where all proceeds go to charity. You don’t have to share our faith, but you have to be okay with the fact that this is a God-led mission for us.

The timeline: Once funding is secured, we make an offer, do due diligence (surveys, land inspections), purchase the property (three to six months), then bring designers down for a charrette — a creative brainstorming session where you explore every possible way to use the space.

The rollout plan:

• Friends and family come first to test everything out
• A Brighter Side Society retreat (another perk of membership!)
• Pop-ups with our advisors
• Start giving proceeds to local island charities immediately
• Phase the design work over the down season — bar, retreat spaces, experiences

Dream partnerships: We want to bring Cheerwine to the Caribbean (we’re reaching out to them about sponsorship and attending their festival near Florence, SC) and — this is a big dream — somehow get a Waffle House on the islands. A girl can dream BIGGIE, right?

We also shared the story of Aaron Siegel from Home Team Barbecue, whose signature frozen Irish coffee was being used by another bar without permission. The lesson? Always ask before you use someone else’s recipe or creation. We’re committed to doing right by every creator and brand we feature at The Holmestead — including reaching out to Megan from The Essential Cocktail Book before serving any drinks inspired by her recipes.

Coming Up: Our One-Year Podcast Anniversary

March is going to be huge. It’s the Charleston Wine and Food Festival’s 20th anniversary AND the one-year anniversary of Never Stop Dreaming Biggie. We launched during the festival last year, and this year we’re going even bigger — recording on-site, hosting a party, making announcements about The Holmestead, and interviewing everyone we can get our hands on with our brand new podcast setup.

If you see us at Wine and Food, come say hi. We’d love to interview you.

Come Be Our Taste Testers in Charleston

Seriously — if you’re in the Charleston area and want to come over, have a couple of cocktails, and be our taste testers, reach out. We’re doing speakeasy-style hangouts at the house most weekends as we practice before The Holmestead opens. Think of it as a soft launch before the soft launch.

And if you know any sugar daddies — I mean, capital stewards — send them our way.

AI Bartending Lesson: Final Verdict

Can AI actually teach you to bartend? After our first real AI bartending lesson, here’s the honest answer: kind of. AI gave us solid recipes, walked us through each step, and even coached my stirring technique with more patience than Brian ever would. But it can’t taste your drink, it can’t tell you that particular rum is wrong for that recipe, and it definitely can’t open your shaker when it’s stuck.

What AI can do is get you started when you’re stuck waiting for the perfect moment, the perfect teacher, or the perfect setup. And sometimes getting started imperfectly is exactly what dreaming BIGGIE looks like.

The “G” in BIGGIE stands for Grow — through challenges, not around them. And growing sometimes looks like standing in your kitchen, covered in lime juice, arguing about jigger measurements with your spouse, while an AI patiently reminds you to hold the spoon loosely.

Keep dreaming BIGGIE, friends. We’ll see you next week.

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🎧 Listen to Episode 49 wherever you get your podcasts!

Connect with Us:

• 🎙 @neverstopdreamingbiggie
• 📱 @angelpholmes
• 🌐 sipindipity.com
• 📧 angel@neverstopdreamingbiggie.com

Learn More:

• 🌴 The Holmestead Hideaway
• 👩‍💼 The Brighter Side Society
• 💼 One-on-One Coaching
• 📅 The Brighter Week — Free Assessment & Waitlist