What I Learned from Billion-Dollar VIP Programs, Hamptons Luxury, and Tommy Boy Roadshows

Lessons For Any Business

I’ve spent two decades at the upper echelon of hospitality. At every level, the lesson was the same: people want to feel connected.

In a world racing toward AI and automation, the human element in business is slipping into the background. Technology can scale, measure, and predict, but it can’t read a room or look someone in the eye. And yet in most businesses, that human element remains the most overlooked and underappreciated asset. Get it right, and it doesn’t just set you apart, it drives profit.

From the Badlands to Casinoland

I grew up near the Badlands of South Dakota, where community was survival and hospitality wasn’t branded, it was just life. The door was always open, neighbors took care of each other, and I didn’t even know to call it hospitality. I only knew how it felt.

Years later, fresh out of college with a marketing degree, I thought I would be writing ad copy. Instead, I was in the back office of a recently bankrupt casino in the Rockies, now under new ownership, suddenly responsible for rebranding a 33-story resort under construction, swimming in slot tournament hell, and deciding who got comped. Some nights we gave away 80% of a 530-room resort property, including 64 suites. I barely understood what “House Advantage” meant. I had no idea what I was doing, but I was intrigued.

It was a Wild West version of hospitality, and I began to realize I was in a corner of business I never expected: relationship marketing. The phrase always sounded a little slimy to me, and to be honest, so did marketing in general. But in casinos, many of the best people on the floor weren’t just there for perks or paychecks. They were there because they genuinely liked taking care of people. Scaling, loyalty, “relationship marketing”, it was more natural than it sounded. Done right, it wasn’t forced. It was people taking care of people. The effect compounded, and I was discovering it was measurable.

The Tommy Boy Roadshow

Fast forward a few years. My analyst and I were somewhere outside Greenville, Mississippi, birthplace of Jim Henson, trading Tommy Boy quotes in a rental Altima while peanut M&Ms melted on the dash. It felt like a roadshow out of a comedy, except we weren’t selling brake pads. We were scaling a VIP program across 41 casinos after a major acquisition.

That program was worth over a billion dollars in annual revenue. The math was simple: just 2% of the database generated more than a third of the company’s revenue. Our job was to give 175 casino hosts the tools to know who to call, who to comp, and how to spread the kind of care that kept loyalty alive in markets as different as Detroit, Bangor, Las Vegas, and the Rockies.

Hosts weren’t just comp machines. The best were relationship artists, celebrating wins, absorbing losses, and making five-figure reinvestment calls on the fly. And here’s the real revelation: hospitality scales only when the people who love connecting with others are supported with the right tools. Lists, CRM, surveys, and business intelligence are not glamorous, but they free frontline people to do what they already do best, make human connections.

Like so many “exclusive” programs, host lists had ballooned until they lost what made them valuable in the first place: focus. Too many players were just names on a page, with no real contact or growth. After months of testing and analysis, we made the hard call to trim lists by nearly 30%. What looked risky at first turned out to be a breakthrough. The players who remained weren’t just more engaged, they were, on average, worth 50% more. And even with fewer guests, overall program revenue increased by 10%. In a billion-dollar program, that’s real money.

Hosts were happier too, because they could finally spend time where it mattered. And with cleaner lists, paired with consistent surveys, contact tracking, and real-time data, they could actually see progress in their relationships. The system worked because the people were supported, and the people worked because they were given the chance to do what they were naturally good at. The big bonus was that this “host love” spread to a population outside of their primary customer lists.

White Glove Lessons in the Hamptons

By the time I landed in the Hamptons, I thought I had seen high-stakes hospitality in every form. But East Coast luxury vacation homes brought new challenges. On paper, the product sparkled: pre-trip planners, stocked groceries, personal concierges, and even the occasional Escalade in the garage. But prestige doesn’t build loyalty, and the operations behind the curtain often lagged the promise.

The Hamptons are the summer power base of New York. Some of the most affluent zip codes in America, but also one of the toughest places for service. It is a hyper-seasonal market on an island with crushing traffic, where staff often can’t afford to live nearby. Retention was brutal. Service lagged.

Some days were pure hospitality lore, like coaxing swans out of a pool while nervous guests filmed, or scrambling when a family’s yacht was chased off a private beach by a man with a shotgun. Other days were quieter but harder: finding concierges who could stay loyal season after season, or stitching together housekeeping and maintenance in a region not built for it.

The lesson was clear. Real wealth wanted presence without intrusion: everything within reach, never forced. That required concierges who could read the room, knowing when to step forward and when to disappear. The companies that thrived invested in capable people, paid them fairly, trained them consistently, and embedded themselves locally. The rest failed. I saw it firsthand working for a company that had scaled too fast, promised “white glove” service, but never built the operational backbone to deliver it. Without structure and support, the vision collapsed as quickly as the economics of the deal.

Members Only

I once spoke with a concierge who had spent his career in luxury travel. He told me about walking down a dim New York alley after dinner when he heard music behind a steel door marked “Members Only.” For a brief second the door swung open, and music, light, and laughter spilled out. The instinct was immediate: I want to be in there.

Casinos understood this with their best VIP lounges. They weren’t the flashiest spaces. They were intimate, well-run, and felt like private clubs. Regulars knew each other, swapped stories, even vacationed together. They weren’t chasing perks. They were chasing belonging.

Exclusivity only works when it stays exclusive. Scale it too wide, and you lose the magic. Done right, though, exclusivity creates gravity.

Final Cut

If you zoom out, most of us are in the experience business. And experiences are built by people, not perks. Hire those who care, give them the tools and leaders to thrive, and design systems that focus their energy and feed them good data. Do that, and you create a profitable ecosystem where clients stay loyal, staff feel valued, and culture sustains growth. It isn’t revolutionary, but the simple things rarely are. Start with the few who carry disproportionate weight, and with the right people around them, the culture you build compounds , driving measurable profit, one human experience at a time.