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Does AI Know Louisville?
Your bite-sized newsletter breaking down Louisville trends, talent and treasures.
Presented by:
🥃 It’s (almost) National Bourbon Day — not that most of you need an excuse. But June 14 is the real deal, so here are 19 ways to raise a glass the right way.
This weekend was a whirlwind: I spent most of it glued to the college baseball playoffs—and I couldn’t be happier. Both Louisville and my alma mater, Murray State, are headed to the College World Series. Let’s go!
My son and I also hit the Wings for Kids RC Airshow. It started slow… then they dropped candy from the sky and unleashed a kid stampede. Total chaos. Total win.
I wrapped the weekend with a 20-person business dinner at Hotel Bourré Bonne. My second visit this month—still impressed. The rooftop bar wins with both professionals and parents. Check out @thelouguru (Todd Lanham)’s review to see for yourself.
Hot job 💼: Director of Operations and Supply Chain at HMI Glass ($175K – $200K). Senior leadership role overseeing manufacturing operations, supply chain, P&L, SIOP, Lean manufacturing, ERP/MRP; degree required, MBA preferred.
Shout-out 📣: Louisville-area startup RxLightning was acquired by CoverMyMeds to expand access to specialty meds. Huge win for founder Julia Regan and the local startup scene! Read full BF article.
Birthday Cheers 🎉: My friend, Leslie Dorris of Yum! Brands just celebrated a birthday! She’s a behind-the-scenes force in internal comms—shaping everything from exec messaging to tech rollouts. Three promotions later, she’s proof that clarity and strategy still win.
-Todd
🤖 Can AI Be Your Louisville Tour Guide? I Tested It.
No expert recommendations. Just a test to see how well AI knows our city.

Yes, AI created this image :)
If we haven’t met, I’ve spent the last two decades building tech companies and the last decade investing in 100+ AI companies. I believe AI is the most transformative technology of our time.
Beyond business, AI is incredibly useful in everyday life—and even a little fun. It recently helped me plan a Disney trip with my daughter, mapping out where to stay, where to eat, and the best age-appropriate activities.
That got me thinking: what would AI recommend for a weekend in Louisville? I asked it to create three different itineraries—for locals hosting out-of-towners, a visiting family of four, and staycationers looking to explore their own city.
Here’s a preview of what it came up with…
Family of 4 Visiting Louisville:
This kid-friendly weekend blends hands-on learning, outdoor fun, and easy meals across Louisville. You’ll explore the Mega Cavern beneath the Highlands, play along the riverfront downtown, and dive into interactive exhibits at the Kentucky Science Center. Stops include Royals Hot Chicken, Churchill Downs, and the Big Four Bridge—plus built-in time for hotel pool breaks and pizza nights. See full itinerary here.
Locals Hosting Out-of-Towners:
Show off Louisville with a curated mix of neighborhoods, from NuLu’s local shops and Biscuit Belly brunch to whiskey tours on Whiskey Row. Day two dives into the city’s cultural heart with the Muhammad Ali Center downtown and dinner at the iconic Jack Fry’s in the Highlands. With rooftop views at 8UP, gallery stops, and Sunday brunch at Morning Fork, this plan hits classic and hidden gems alike. See full itinerary here.
Staycation for Locals:
Reset without leaving town by checking into 21c Museum Hotel in downtown Louisville, where art and luxury blend seamlessly. Your weekend flows from creative energy in NuLu to outdoor escapes in The Parklands and riverfront dinners at River House. With meals at Le Moo, patio drinks at Ten20 Brewery, and laid-back brunch at Please & Thank You, this itinerary makes your own city feel like a whole new place. See full itenrary here.
I asked AI to summarize what it took to get there and here were the steps.
Absolutely—here’s a step-by-step summary of how we got here:
1 Asked for three Louisville itineraries based on audience
2 Asked for more specific location details
3 Uploaded original Orlando-style example - said to match it
4 Approved one itinerary in new style — requested other two
5 Asked to rate its quality (it said 8.5 - I said get to 10)
6 Re-created upgraded versions
7 Delivered all three fully upgraded docs
Yes, it can take AI some back and forth to get what you want… but it ended up pretty great! See for yourself, by clicking here to see all three travel plans, plus a super detailed prompt you can copy and use for your own adventures.
⚡️ Spark Poll
Most Overrated Louisville Food |
Last week’s poll results: A surprise $100 just for fun — where are you spending it locally?
Restaurant I’ve always wanted to try - 60%
Shopping a local boutique - 0%
Show or event I wouldn’t normally buy - 0%
A spa treatment or massage - 20%
Random adventure with friends (no plan, just vibes) - 20%
🗓️ Presented by: 21C Hotel
Looking for a romantic downtown escape that skips the clichés? The Love Birds package at 21c Museum Hotel includes a dreamy overnight stay, chilled bubbly, artisanal chocolates, and a $50 credit to use at Proof on Main.
It’s the kind of date night upgrade that makes you forget you're still in Louisville. Bold art, cozy luxury, and a killer location—it’s a vibe. Perfect for anniversaries, birthdays, or spontaneous "just because" moments.
Side Hustle Spotlight
Creative Hustles. Real People. Extra Income.
By day, Keren Benabou crushes it in Louisville real estate. But her side hustle? KB Luxury Limo Service—a sleek black Mercedes Benz Sprinter limo that turns any night into an experience, complete with wrap-around seating and space to move in style.
Friends of mine have booked it and raved. My own son used it for a big night out with friends—and they’re still talking about it. Keren brings the fun with flair, and this ride’s a vibe. You’ll want to follow along and book your own and follow on IG!
A big personal thanks to Keren for supporting my charity poker events and attending Louisville Spark Live! Got a creative side gig or know someone we should feature? Tell us here.
🤫 Confess & Tell
Real Opinions. No Filters. No Names. [Submit yours here]
Confessional 🤫: We’ve got an underrated food scene—my out-of-town friends are always impressed. But somehow they all show up thinking the Hot Brown is the Louisville dish. I wish we could quietly retire it from the brochure. I’ll take a Feast brisket sandwich or a Mayan Café lima bean taco any day.
🏢 Louisville Spark Job Board
Who’s hiring in Louisville? 5 Trending jobs
Project Executive at Michael Page ($up to $185K). 10+ yrs construction project management on multi‑family ground‑up projects; working knowledge of trades, forecasting, RFPs, and vendor coordination.
Health & Wellbeing Manager at Yum! Brands ($122K – $143.6K). Lead US benefit program modernization with automation and employee-first focus. Requires experience managing health/wellbeing programs and vendor relationships.
Senior Director, HSC Business Affairs at UofL Orthopedic Surgery ($118K–$177K). 8+ yrs admin/finance ops in academic or clinical setting. Must manage budgets, HR, billing, and strategic planning for a surgical department. Master’s preferred.
Watchman Therapy Awareness Rep at Boston Scientific ($112K+ base + commission). 2+ yrs med/pharma sales. Grow referrals and educate cardiologists on stroke-prevention implant. Strong fit for those with cardiovascular sales or clinical education background.
Clinical Account Manager at Ceribell ($100K base / $180K OTE). 3–5 yrs critical care sales or RN w/ industry background. Launch and grow adoption of seizure detection tech in hospitals. Clinical training + hospital sales chops required.
Presented by: Justin Willman Illusionati Tour
Magician and Netflix star Justin Willman brings his ILLUSIONATI tour to Louisville on Friday, June 13 at the Brown Theatre. It's a one-night-only blend of magic, comedy, and mind-bending moments the whole family can enjoy—think “Magic For Humans” meets secret society vibes.
From sleight-of-hand to mind-control, Willman’s show is designed to wow skeptics and believers alike. VIP options include premium seats, a poster, and a post-show meet & greet. Tickets are on sale now.
🗓 Friday, June 13, 2025 | 7:00 p.m.
📍 Location: Brown Theatre | 315 W Broadway, Louisville, KY
💵 Cost: $31.50–$66.50 | VIP options available
🎩 Bonus: Family-friendly + meet the magician himself after the show
🎟 Get tickets here
📆 What’s Sparking This Weekend
We found the fun—so you don’t have to.
🎟️ Featured event
⚽ LouCity Nonprofit Night
Friday, June 14 | 8:00 PM @ Lynn Family Stadium
Cheer on Louisville City FC while supporting local nonprofits. A portion of ticket sales benefits participating organizations, and the concourse will feature booths from community partners. A high-energy match with a meaningful mission.
🎉 Friday – June 13
🎭 Shakespeare in the Park: A Midsummer Night’s Dream
Friday, June 13 | 8:00 PM @ Central Park (Old Louisville)
A free outdoor production under the stars. Bring a blanket or lawn chair and enjoy one of the Bard’s most magical comedies, courtesy of Kentucky Shakespeare.
🥃 Bourbon & Beyond Presents: Summer Happy Hour Series
Friday, June 13 | 5:00–9:00 PM @ Ten20 Craft Brewery (Highlands)
Enjoy live local music, exclusive Bourbon & Beyond giveaways, and drink specials. Great way to unwind and preview what's coming to the big festival.
🎨 After Hours at Speed Art Museum
Friday, June 13 | 5:00–10:00 PM @ Speed Art Museum
An elevated evening featuring art, music, drinks, and food. This month’s theme includes a jazz performance and special gallery tour—perfect for a date night or friends’ outing.
🌟 Saturday – June 14
🚘 Whiskey Row Car Show
Saturday, June 14 | 10 AM–4 PM @ Downtown Louisville – Whiskey Row
Over 200 classic and exotic cars line the streets for this free, family-friendly event. With food trucks, music, and vintage vibes, there’s something here for car lovers and casual strollers alike.
🎶 Sky Soul Festival
Saturday, June 14 | All Day @ Waterfront Park
A celebration of music, culture, and creativity along the river. Enjoy live performances, art vendors, and a lively crowd—this is one of the summer’s best community vibes.
📖 Baby & Toddler Storytime
Saturday, June 14 | Morning Sessions @ Louisville Free Public Library (various branches)
Designed for the littlest book lovers, these short and sweet sessions include songs, rhymes, and stories to engage developing minds. It’s a cozy way for families to start the weekend.
Sunday – June 15
🌈 Kentuckiana Pride Festival
Sunday, June 15 | 12 PM–10 PM @ Big Four Lawn at Waterfront Park
A colorful celebration of love and inclusion. With drag shows, live bands, food trucks, and a designated Family Zone, this is a can’t-miss day of joy, acceptance, and community spirit.
🌱 Family Terrarium Workshop
Sunday, June 15 | Afternoon @ Gravely Brewing Co.
Get your hands dirty with this make-your-own succulent workshop—great for kids and adults alike. Materials provided, plus food and drinks available on-site. Craft, sip, and unwind.
🎤 Funniest Person in Louisville Contest
Sunday, June 15 | Evening @ TEN20 Craft Brewery
Local comedians compete for the crown—and your laughs—in this casual, crowd-powered comedy showdown. Grab a brew, pick a favorite, and enjoy a night of local talent on tap.
🥃 Final Sip
I’m sending you this one straight from Omaha — and yes, I’m absolutely pumped to be here. Two teams I love, one College World Series, and a whole lot of rally energy packed in my suitcase.
Louisville showing out. Murray making history. I don’t know what’s in the water lately, but I hope it keeps flowing.
-Todd