The Slow Burn: One Moment at a Time (Pt. II)

“$21,000 and a Cigar Brand Dream”

Events can make or break a cigar brand.
Especially when the person holding the mic fails to connect.

I've pitched thousands of people over the years.
Hosted hundreds of events….some unforgettable, others... well, I probably left a few brain cells behind.

But one night still stands out.
Not because of who was there.
Not even because of what I said.

It stands out because of the tab:
$21,000.

Yup.
Twenty-one large.

Thank God it wasn’t my card, it was the company’s.
Corporate AMEX, God rest your credit limit.

The setting?
The Billionaire Boys Club, Midtown Manhattan.

No, not the Pharrell brand.

This was an ultra-lounge sitting quietly above a Ferrari dealership, because, of course, it was. One of those velvet-rope, "invite-only," high-gloss rooms that smells like generational wealth and overpriced cologne.

The mission?
Get in with the gatekeepers.
High-net-worth individuals. Board members. C-suites and their admins.
Not just shake hands, gain influence. Make them trust you. Make them use our solution.

The truth is, our company wasn’t exactly built for this kind of entertainment.
But I was.

Young, fired up, and chasing a challenge, I got handed the keys to a new vertical:
Celebrities.

No roadmap. No playbook. Just a target and a Rolodex that didn’t exist yet.
So I built one.

Within a year, I had cracked the circle. I was working with the ACPA (Association of Celebrity Personal Assistants) and the NYCA (New York Celebrity Assistants).

I connected with Steve Harvey’s assistant. Nate Berkus’s team.
Before I knew it, we had two headline events:

One at the newly opened SLS Hotel in Los Angeles, and another in New York, the night of the infamous $21K tab.

It wasn’t just about flash. It was about making people feel seen.
Even in a room full of status, people crave sincerity.

Some folks say L.A. is fake. I get it. With 243 plastic surgeons in Orange County alone, the stats kinda back it up.

But underneath the filler and flash, there are real people in that city, grinding, dreaming, and trying to make something of themselves in a place where social currency is fame, and the price of admission is exclusivity.

One of those people was Kim, a client of mine who ran operations for the ACPA, the Association of Celebrity Personal Assistants. She was also the handler for a nationally syndicated talk show host, which meant her life was a tightrope walk of managing egos, keeping up appearances, and maintaining absolute discretion.

Over time, we became friends.

I learned she loved to travel and craved new experiences.
But I also learned how lonely it could get.
How people only invited her places to get closer to her boss.
How dating was damn near impossible because she could never be sure if someone wanted her… or access.

By her own admission, she’d grown a little calloused.

Then there was Kelly
.

Kelly was—and still is—a total badass.
You know in the movies when someone says,
“Have your people call my people?”
Kelly is those people.

She’s the high-functioning bosslady behind a nationally recognized interior designer and TV personality.
Her days were packed with international travel itineraries, renovation projects, personal appearances, brand deals… and zero room for screwups.

She didn’t just keep things on track.
She made it look effortless.

I spent months flying between L.A. and New York, meeting with Kim and Kelly, building trust, and eventually co-hosting bi-coastal events that brought the A-listers and their teams together.

And somewhere along the way, I met Patrick.

Patrick worked for a star, the kind with a résumé longer than most people’s lives.
She was a legend of the stage and screen.
A Steel Magnolia.
A Moonstruck matriarch.
The voice in Look Who’s Talking.
And a force in Mr. Holland’s Opus.

She passed in 2021, but left behind a legacy of over 130 stage productions, 60 films, and 50 television series.
Working with her team was like stepping into cinematic history.

Now, a lot of folks get starstruck.
Me? Not really.

Well...
Except for that one time I choked at the urinal next to Steven Tyler.
(We’ve covered that.)

The celebrity assistants thought their bosses were high-touch.
But I was living in a different reality.
A billionaire reality.

They didn’t know that while we were setting up gift bags and lighting votive candles, I was fielding calls from the likes of Sadie Ferguson, Laurene Powell Jobs’s right hand.

Or that at any moment, the RNC (Reince Priebus) or DNC (Debbie Wasserman Schultz) might call with a last-minute ask.
Or that Philip Falcone might demand a car at the East 34th Street Heliport right now to get to the Hamptons by sunset.

Hell, one time Air Force One entered NYC airspace unannounced and rerouted every flight.
Suddenly we had heads of state and hedge fund execs scrambling for ground transportation.
Another time, a volcano erupted, and I spent two days rerouting a Bronfman (yes, that Bronfman) back to U.S. soil.

And yes...
Trump was impossible.
But I still landed the 2014 GOP Convention transportation contract.

Looking back, it’s easy to laugh.
It was wild.
It was chaotic.
And somehow…
It worked.

Not because I was “selling” something flashy.
Not because I knew all the right names to drop.

But because I understood what people really wanted.

Genuine connection.
And a baller service or product to back it up.

That’s it.
That’s the whole play.

And it’s the same thing I’m building with Brolo.

Because no matter who you’re dealing with…celebrity, billionaire, boardroom boss…
People remember how you made them feel.
They remember the experience.
They remember the connection.
They remember the moment.

And the people who remember those moments?
They come back.

It’s not about being the loudest.

It’s about being real.
Present.
Human.


The best brands aren’t built in boardrooms.
They’re built at the bar.
In lounges.
Over stories and smokes.
One moment at a time.

Light Up & Lean In,