Tom Pifer didn’t set out to run one of Louisville’s most talked-about Derby Week events, he set out to help his dad fight Parkinson’s disease. What started as a scrappy fundraiser with more passion than budget has grown into the Kentucky Bourby, a premium bourbon tasting experience at Progress Park that now draws nearly 750 guests the Saturday before the Kentucky Derby. Five years in, Tom and his organization TKO Flight Club have proven that a strong “why” builds a loyal community of donors, distillery partners, and guests who keep coming back.

On this Partner Series, Landon and Tom break down exactly what makes a premium event work and it comes down to a few principles done consistently well. Start with a clear reason for the event. Design a quality experience where less is more (the Kentucky Bourby features over 150 bourbon labels with zero lines to wait in). Build flexible partnerships. Tom invites distilleries like Maker’s Mark and Four Roses to show up on their own terms, which led to a co-branded on-site screen printing activation and a $200 swag bag experience exclusive to Bourby guests. Tom invests in quality hats and shirts that people genuinely want to wear, with the slogan “Drink Bourbon, Fight Parkinson’s” doing the storytelling on its own. 

Whether you’re planning a company event, a charity fundraiser, or a customer appreciation night, the playbook Tom shares here is worth your full attention. The details that elevate an event are not complicated but they require intention. Watch the full replay to hear how Tom built something special from the ground up, and what he’d do differently if he were starting over today.

Watch The Episode

Key Takeaways

• A strong “why” is the foundation. People show up for a reason, not just an event.
• Quality experience beats quantity. Do fewer things exceptionally well.
• Give partners freedom to show up on their own terms. Investment follows ownership.
• Branded merch is free advertising. Only invest in quality people genuinely want to wear.
• A clear, simple slogan (“Drink Bourbon, Fight Parkinson’s”) turns guests into brand ambassadors.
• Build distillery and brand partnerships slowly. Trust compounds into bigger activations over time.
• Co-branded merchandise with major partners adds instant credibility to your event.
• Keep it manageable. Passion projects die when they stop being fun.
• Post-event triage and continuous improvement beat trying to get everything perfect on day one.
• Design the event you’d want to attend. That clarity will guide every decision you make.

Chapters

• 00:00 Landon introduces Tom Pifer and Kentucky Bourby
• 01:00 How the Kentucky Bourby has evolved since 2024
• 03:07 The origin story: TKO Parkinson’s and TKO Flight Club
• 04:54 Why a strong “why” is the foundation of any great event
• 06:26 Building distillery partnerships that keep coming back
• 08:07 Crafting a premium experience where less is more
• 10:39 Managing a passion project without burning out
• 13:27 Partnering with ESPN to expand audience reach
• 17:21 Why branded merch is free advertising for your event
• 23:09 Four Roses brings 100 swag bags and private tastings