Cigars at the usual spot.

Listen to this article
Browser text-to-speech
Complimentary cigars, three afternoons, no ticket needed. RSVP for the secret swag.
Carrie: Hey Tracie, what do you want to do today?
Tracie: Same thing we do every day, Carrie - try to take over the world.
Carrie: ok, but we have to go to a tradeshow first. Any ideas?
Tracie: well, you remember that thing we did that time at the place?
Carrie: you mean the thing at the place with the stuff?
Tracie: Yeah, that.
Carrie: Good 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?
Tracie: Make it so.
Carrie: Let's go to work.
Carrie Simpson holding a phone and a glowing green prop on a conference floor.
Tracie holding a phone and iced coffee at an outdoor table.
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.
- Wednesday — 3 to 5 pm
- Thursday — 3 to 5 pm
- Friday — 4 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.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
Two friends holding flasks at the suite bar next to buckets of ice
A friend wide-eyed mid-sip from a flaskSwag 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.
2013 — The 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 floor2014 — The 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
The suite packed with friends holding flasks
Three friends smiling at the suite bar2015 — Coffee 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
Chalkboard booth art: These are the Managed Sales Pros leads. These are for closers.
Lounging on a hotel bed firing a pink cash cannon, captioned: Hey kids, I got your inheritance right here2016 — 15 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
Pouting in the stocks
A friend in a Chewbacca mask striking a pose2017–2020 — Dinners, 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
Four friends at an outdoor party, two wearing fake mustaches
A group of friends with drinks and cigars on a patio under string lights
Kissing a giant cardboard face on a stick
A mug that reads: your enthusiasm is scaring everyone
A sepia saloon portrait in costume2021 — Bourbon & 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
Carrie and Ian from behind, showing their shaved-in designs: a red ampersand and a teal logo
Carrie and Tracie arm wrestling on the floor
A group of friends making faces at the photo booth2022 — The 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
A friend in the barber chair on stage, caped and ready, with the host holding a mic2023 — Main stage
Carrie and Ian on the main stage with Montel Williams.
Carrie on stage in a white armchair, hands up
Ian, Montel Williams and Carrie on the main stage2024 — Still 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 sign2025 — Tracie, 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.
2026 — Now
We’re back. Cigars at the usual spot Wednesday through Friday, and secret swag with your name on it if you RSVP.
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 teeth
Carrie and Ian, Ian in red aviators with a cigar in his teeth
Travel cases packed full of cigars
A cigar and a friend on a leather banquette
Lounging with a cigar in a yellow lawn chair
Cigar in mouth, big sunglasses, and a Trashy Diva necklaceSame spot. Same people. New swag.
Let’s pretend none of this ever happened.
Hosted by Carrie, Tracie and Ian. See you at the usual spot.
Brought to you by Fox & Crow Group.
