A neon sign on a wood wall that reads: Let's pretend none of this ever happened.
Carrie Simpson holding a phone and a glowing green prop on a conference floor.
Carrie
Tracie holding a phone and iced coffee at an outdoor table.
Tracie

CarrieHey Tracie, what do you want to do today?

TracieSame thing we do every day, Carrie - try to take over the world.

Carrieok, but we have to go to a tradeshow first. Any ideas?

Traciewell, you remember that thing we did that time at the place?

Carrieyou mean the thing at the place with the stuff?

TracieYeah, that.

CarrieGood idea. Let's do that again - but let's do it better. Oh, and let's make it a secret. Can we give away secret swag?

TracieMake it so.

CarrieLet's go to work.

Cigars at the usual spot.

Complimentary cigars, three afternoons, no ticket needed. RSVP for the secret swag.

RSVP for secret swag
Carrie carrying two cases with humidors filled with custom-blended cigars.

The usual spot

Rosen Shingle Creek, the outdoor smoking area. You know the one.

  • Wednesday3 to 5 pm
  • Thursday3 to 5 pm
  • Friday4 to 6 pm

Cigars are on us, custom blended for the show and wearing our own band. Just show up. The secret swag goes to people who RSVP.

Tracie Orisko from Huntress smoking a cigar.
Tracie lights up.

RSVP for secret swag

Tell us which afternoon you’re coming and we’ll hold the secret swag with your name on it.

By RSVPing you agree that none of this ever happened.

Registered? You’re done. Or take a stroll down memory lane.

Not all swag is created equal.

It started at the Waldorf. We forgot to buy cups, so the flasks we’d brought as booth swag suddenly became necessary, and by the next morning we had none left to give away. People still come up to us today holding those two-dollar flasks. We figured it was time for an upgrade.

RSVP for the secret swag. We’re not saying what it is. Some are collectible. Some are very collectible. You won’t know which one you got until you pick it up.

Tracie on a sunny balcony with a funnel and a flask
Quality control.
Two friends holding flasks at the suite bar next to buckets of ice
For display purposes only.
A friend wide-eyed mid-sip from a flask
Inspecting the craftsmanship.

Swag contents may vary. Swag may be empty. We can neither confirm nor deny.

Sixteen years of evidence

Same friends, different hotels, and a running tab of costumes, dinners, races and cigars. Here’s what we can show you.

2013The first one

Our first year together at the show. We sat in every keynote and went looking for our why. It turned out to be cigars.

A Discover Your Why banner over the show floor
Found our why. It was cigars.
2014The Waldorf

Our first suite party. We forgot cups, so the booth-swag flasks got pressed into service and the booth had none left. It ended with Carrie in her bathrobe throwing out the Canadians and the Aussies, and very nearly got us thrown out of the Waldorf.

Carrie and Tracie in front of their booth banners
Matching the booth. On purpose.
The suite packed with friends holding flasks
The suite, around midnight.
Three friends smiling at the suite bar
Hosting, technically.
2015Coffee Is For Closers

The Ritz, $1,000 in ones loaded into the cash cannon, 2,000 pounds of Coffee Is For Closers coffee to give away, a half marathon with a McDonald’s stop in the middle, an owl suit, Rocco’s Tacos, and cigars every night. We regret nothing.

Mid-race coffee and a breakfast sandwich in running gear
Mile seven. Coffee break.
Chalkboard booth art: These are the Managed Sales Pros leads. These are for closers.
These are for closers.
Lounging on a hotel bed firing a pink cash cannon, captioned: Hey kids, I got your inheritance right here
Estate planning.
201615 miles, then Disney

We ran 15 miles and went to Disney. Cigars every night, naturally.

A running selfie with a 15.10-mile run summary
15.1 miles. Then cigars.
Pouting in the stocks
Detained.
A friend in a Chewbacca mask striking a pose
No further questions.
2017–2020Dinners, after-parties and other alibis

Every year has the official agenda and then the part everyone actually remembers.

A long candlelit dinner table full of friends
Table for fifteen. Again.
Four friends at an outdoor party, two wearing fake mustaches
Mustaches were mandatory.
A group of friends with drinks and cigars on a patio under string lights
The patio crew.
Kissing a giant cardboard face on a stick
Brought a date.
A mug that reads: your enthusiasm is scaring everyone
Fair warning.
A sepia saloon portrait in costume
Wanted.
2021Bourbon & A Barber

A cut above the rest. Top-shelf cocktails, free cuts from a celebrity barber, a photographer, and suite access for anyone who texted us their business card. Ian’s first party on the hosting side, after years of showing up as an MSP.

The barber standing front and center, arms crossed, with Carrie and Ian behind her showing their fresh cuts: a red ampersand and a teal logo
The barber, and the evidence.
Carrie and Ian from behind, showing their shaved-in designs: a red ampersand and a teal logo
Carrie and Ian. Commitment.
Carrie and Tracie arm wrestling on the floor
Settling a business disagreement.
A group of friends making faces at the photo booth
The regulars.
2022The Beard Shave Fundraiser

Real beards, fake beards, a barber chair on stage, and a room full of people paying good money to watch someone else get shaved. All for a good cause. Also the year Ian slept in Penny, the Richardson family van, in the hotel parking lot. During a hurricane.

A friend with a very long beard next to a friend in a fake gray beard
Real beard. Fake beard. You decide.
A friend in the barber chair on stage, caped and ready, with the host holding a mic
In the chair. No turning back.
2023Main stage

Carrie and Ian on the main stage with Montel Williams.

Carrie on stage in a white armchair, hands up
Carrie, mid-story.
Ian, Montel Williams and Carrie on the main stage
Sharing the main stage with Montel Williams.
2024Still here

Still showing up, still at the usual spot, still pretending none of it ever happened.

Ian and Carrie taking a selfie in front of the show sign
Year whatever. Still here.
2025Tracie, solo

Tracie held down the usual spot. Carrie and Ian stayed home, knee-deep building the MSP Sales Process CRM and Instinct, our MSP decision intelligence platform. Let’s not do that again.

2026Now

We’re back. Cigars at the usual spot Wednesday through Friday, and secret swag with your name on it if you RSVP.

RSVP for secret swag

The cigar club

Sixteen years, a lot of hotels, and one constant: we find the smoking spot and we hold court.

Ian in a wide-brim hat with a cigar between his teethCarrie and Ian, Ian in red aviators with a cigar in his teethTravel cases packed full of cigarsA cigar and a friend on a leather banquetteLounging with a cigar in a yellow lawn chairCigar in mouth, big sunglasses, and a Trashy Diva necklace

Same spot. Same people. New swag.

RSVP for secret swag