Digital Insiders Take Disney: Part I {What Actually Happened}

On Sunday November 7th, 80 Digital Insiders descended on Disney’s Grand Floridian Resort & Spa for a week of play, fun, and masterminding. We all rolled in at various times of the day, and collected together at the outdoor patio at 6pm to connect and say hello.

It’s hard to explain how much excitement was in the air. I wish I could bottle it up and open it whenever someone needs it. Something about the combination of fun, business, sun, and people made this mastermind the most anticipated ever.

Some brought their children (six kids was the the record!), some brought spouses, partners, and friends.

Jessica and I handled registration that afternoon as every member got a notebook, hoodie, and a 20 page individualized itinerary to keep track of schedules and reservations! In addition, we handed out directions and rules for the pirate game intended for bonding and photos (more on that later). Everything was going smoothly until I sent an email to Club 33 asking about the VIP tours I’d secured.

Turns out the policy had changed about the tours. You could only park hop if you had a park hopper ticket, and I’d told everyone they only needed a base ticket. After 90 minutes on the phone with the club, we’d run out of options on how to do that. I was crushed. I knew I’d have to deliver the bad news Monday morning to prep for the fact that we’d only get through one park on Wednesday.

On the off chance that the event team could help us, I had Jessica round up every single person’s email address and reservation confirmation # in case they could upgrade everyone’s ticket in the backend.

Monday morning – the entire group was downstairs and at the conference room by 8:30am. The room was abuzz with hugs and excitement and some pirate loot negotiating happening as the game started to heat up.

We spent the first hour going over the logistics of the day and week (there is a LOT to know about Disney if you’ve never done it) and then we masterminded until 4pm.

I did a presentation on organic marketing, and how to plan a marketing initiative for the quarter. After that we had two presentations by DIers – Julia Taylor on her Geekapoolza Summit + Greg Bottaro on a new way to deal with difficult inner emotions we have.

In between – the group of 80 split up to go to various lunch places. Logistically this was one of the more complicated parts of planning. Since Disney has virtually no walk up service, we made tons of reservations on various accounts and then had people sign up to the lunches. We also had to make sure the restaurants were close enough to the convention center that they could get back. In hindsight, I think it was an excellent way for people to have a meal together who might otherwise clump together in the same group the whole week. Also in hindsight, I would have probably only done one RSVP per day instead of two, since some of the night reservations were tiring and people wanted to change plans.

Monday night we boarded two coach buses and went to Animal Kingdom just as it was closing! The feeling of all of us walking into the park as everyone was walking out was one I will NEVER forget. We went into Africa’s Harambe Market and feasted on turkey and prime rib and a million other things I can’t remember any more. a West African band played music the whole time, and after a visit from Rafiki, it was time for Pandora.

The Disney team walked us into the bioluminescent Pandora land where we had a massive dessert party and rode Flight of Passage as many times as we could in 90 minutes. Coming back on the bus that night, I couldn’t believe that one – it had only been one day, and two – that I had the honor of that experience. I’ll never forget it.

My sister Nicole and I stumbled into bed around midnight and I fell asleep thinking that the 45 people who’d planned to do Magic Kingdom on Tuesday morning at 8am would probably be a no show.

I was wrong. We all gathered by the Gingerbread house at 8am to get into the park early enough to do a few rides before the crowds got too big. This was the ONLY time we didn’t have any special privileges. So it was a strategic outing into Magic Kingdom to hit all three mountains – Space, Thunder, and Splash. And yes, we did it!

By 11am, we’d done a bunch of fun rides, and then broke off for lunch.

The remaining 40 or so people stayed back at the resort to mastermind by the pool, and we all reconvened as a group at 2pm. That day – I spoke on sticky content (and how to be memorable on social), and then we had two talks: Cathy spoke on branding and Sharon did a talk on how to communicate with difficult people. We had a breakout session for smaller masterminding, and then we ended around 6pm.

Looking back, Tuesday was a long day. To go from Magic Kingdom to masterminding to another dinner at night…this is where I thought, “Gosh are we all gonna make it til Friday?”

That night we all split up all over the World and went to various restaurants. I was at the California Grill where the music pipes in the for the fireworks at night. Afterwards we came back to the Floridian for what would become “hot tub masterminding”. Drinks, hot tub, and late late hours… it was this way from Tuesday on forward.

As it turns out, the issue with the park tickets and VIP day ended up getting solved. The event team said if I could get everyone’s number, they would upgrade their ticket package to a park hopper and then bill me for them all. So that’s what I did. And this meant that all the VIP tours could hit as many parks as they wanted in seven hours.

Wednesday morning was bright and sunny.  The pirate game was getting pretty intense at this point. There were deals being struck, and people were taking photos like crazy.

Since certain photos equaled money, by the end of the VIP day, we had over 1000 photos. It was crazy. The VIP tour guides were totally up for the game, and helped several groups get the harder to find shots.

The VIP tour I was on didn’t hit all four parks in one day, but still we were exhausted by the end of our seven hours. We’d managed two parks and I watched on Instagram as other teams made it to all four!

That night was another dinner, and it was a rainy night. But it didn’t stop us from fireworks or the hot tub. Shenanigans continued to go down with the pirate game, and most of us were limping from sore feet.

Thursday we came back for a full day of masterminding. On this day, I spoke on benchmarks and underperforming offers, and we had four DIers do a give. Sarah Masci spoke on VIP days, Portia spoke on money, Renee on sales, and Christina on Black Friday sales.

That night was the second hosted dinner. Due to the rain we had it indoors, but it didn’t change a thing. We drank, we ate, we watched fireworks, the kids (and adults) got pictures with Mickey, and we danced… HARD.

I also announced the end of the pirate game. Five boats banded together against one (long story LOL), we uncovered some serious plot twists, and saw people in a new light! The winning pirate ship – The Barnacle – earned pirate pins and a $2500 cash prize.

When that party ended at 10pm, we made our way to the hot tub and pool and closed it out at 2am. It felt like graduation night. No one wanted it to be over. Even though there was another day, a bunch of people left on Friday so it had that sad ending feeling to it.

Friday we started at 11am (thank God)! There were a bunch of breakfasts in the morning and then we got together from 11-4. Cathy + I spoke on design, Abby spoke on brand photography, and Jess Santise taught us how to make branded gifs.

I tried to end the day with a poetic speech, but I didn’t really have one. I just tried hard not to cry. To finish the mastermind, we went into Epcot (it was so busy), ate and drank through the world, and ended the night with an epic view of the new Harmonious show.

  • We walked 42 miles in a week.
  • Saw 10 fireworks shows between Magic Kingdom and Epcot.
  • Took thousands of photos.
  • Saw some major bonding + competition both.
  • Did what we do best – masterminded.
  • Came away with a renewed sense of possibility and excitement for the future.

It was a feat of logistics and planning I could not have pulled off without my team. The goal I had for this trip was simple…Give people a magical experience that would bring hope, fun, joy, creativity, and possibility while also creating a space for new friendships to form, and old ones to connect.

Knowing how hard business is, and how much we need other people, I knew this would help us all after a very long and stressful 18 months trying to run a business in a pandemic.

Goal met.

As the fatigue starts to wear off and my energy returns, I had a renewed excitement for 2022 and what’s to come! Want to try Disney with me? Next opportunity is the Marketer’s Heart event in February!