Nick Reese

This is the story of how the best week of my life ALMOST didn’t happen.

I write this overlooking Venice Beach, CA with the sound of electric guitar and laughter and shouting in the background.

The vibe in Venice is “cool” but almost too cool. People here are definitely trying hard and it shows.

I get heckled for walking too fast and weird looks when I smile at people. I guess I’m back to reality.

This is an amazing juxtaposition of the last week where I was utterly blow away by the people I was around. No one was trying to impress each other, everyone was just 100% themselves.

Skip Winter 2012

The last 7 days in Mexico at a Mayan jungle retreat, with 10 close friends.

Our wolfpack consisted of 10 entrepreneurs, authors, world travelers, tech ninjas, critical thinkers, and change makers.

We were all there for a little conference/retreat I arranged with the help of Jess Commins called Skip Winter Conference.

What happened at our retreat is hard to describe and can really only be summed up as magic and serendipity.

The best way to describe it is a family of people who are taking their own path in life and “get it.”

All in all, it is amazing what happens when you put 10 extremely positive and smart people together in a place with slow internet and outdoor living.

People who where there did a great job of summing up the magic in addition to this post.

The Making of Skip Winter 2012

Almost a year ago, I was sitting in a coffee shop in Buenos Aires, Argentina talking with my friend Jon Myers.

We were talking about how great it would be to get a group of like-minded entrepreneurs together in a tropical location during the dead of winter.

We had been discussing how conferences were an interesting business model and that it would be fun to arrange one.

The original goal was to host an attendee lead conference with roughly 20-24 people attending.

In typical Nick-fashion, I jumped into action and registered a domain and put up a simple squeeze page.

I had no idea how I’d pull it off or if there would even be interest, but I felt like I had nothing to lose.

Once the squeeze page was up, I simply tweeted it out to see if there would be any interest.

Over the following months, I would work with Jess Commons to secure a Eco Friendly Mayan playground with a cenote (grotto in a cave) and mini golf course called Taninah. (cribs style video at the end of this post).

The initial outlay to secure the property was hefty but I decided to move ahead anyways.

As the date of the event quickly approached I began to get cold feet, wondering if I would pull it off. It was 5 months out and with 200 people on a simple email list, I reassured myself that I would be able to fill up the event.

During the prior months of planning, I had plenty of people telling me it was a great idea, but very few people actually committing to attend. (Part of this had to do with me not wanting to “hard sell” my friends. There is a lesson right there, don’t market to your friends. Duh!)

Pulling the Plug

As the months flew by, I starting having moments of self-doubt and the stress was getting to me.

I found myself not wanting to follow through with the original vision. I was hesitant to email the mailing list, simply because I wasn’t clear on what I wanted.

To make matters worse, I began to think this could be my first public failure and maybe I wasn’t meant to put on events.

After a couple days I decided I was going to cancel the event.

I emailed the owner of Taninah and asked about the refund policy.

It would be over $5k to cancel the event, but I was ready to cut my losses instead of have a public failure and organize an event I wasn’t passionate about.

Roughly 90 days out, I ceded defeat.

I called all the attendees who had paid and issued them all refunds.

All that was left was to do was formally cancel the reservation.

In my mind Skip Winter 2012 was over.

A New Vision

Distressed I called my mentors, but my mom whom I’m really close with gave me the best advice.

She suggested that I wait a week and give it space since the deadline to cancel was still a couple weeks away.

During this week, I realized that what Skip Winter had evolved into was something I was doing to impress others instead of something I wanted to do. This realization made me angry, then mad, then determined.

As the week pushed on, I began to think about what other possibilities the sweet location could be used for.

I mean, I had an amazing property booked during the coldest month of the year and plenty of friends who are location independent.

Suddenly my mind began to race.

I realized I wasn’t passionate about putting on a conference, but what I was passionate about was bring awesome people together.

Quickly I began to reach out to friends and one by one they all began to commit.

Within just 3 weeks all the pieces fell into place and Skip Winter 2012 was on.

An Overview of Skip Winter

What was Skip Winter Like?

Well it’s hard to explain unless you’ve got 30 minutes or so.

Skip Winter was unlike any event, gathering, retreat, you name it, that I’ve been to. It was magic. The original idea was for us to “craft the talks of our lives” or at least work on an idea that could be evolved into a Ted(esque) talk.

The first day, we all agreed to nuke the schedule and let the week unfold serendipitously. That decision would shape the entire week.

The rest of the week was spent doing whatever we pleased. Here are some highlights:

• We spent time playing dodgeball, obstacle courses, mini golf, wiffle ball, and more.
• We invited our own games (I’m the reigning “trampball champion”).
• We did yoga, led by Jenny Blake and Mike Hrostoski (if you are in NYC check out GeekYogaNYC.com).
• We played Werewolves vs Villagers. (the best and worst game ever.)
• We did impromptu business strategy sessions.
• We talked about the important stuff in life.
• We ate awesome Mayan food, we drank, and we did whatever struck our fancy.

Ultimately what came out of it was our own little culture of slang, memes, and inside jokes — in addition to business strategy and the other “tangibles” you look for in a conference / retreat. More than anything we came out as a team and a group of life long friends.

Here is an Cribs-style video we put together while hanging out. Shout-out to Sean Ogle and team for editing this together.

People are Everything

After running Skip Winter 2012, one thing is glaringly apparent. If you get the right people together, everything else will sort itself out. Our group could have had a good time sitting in airport or the hospital (oh we did that, sorry Kyle) or even just hanging out by the pool. If you ever throw an event, never compromise on the people. One rotten apple will ruin the whole bunch.

Note: this post was written during 4 different sittings. I’ve been traveling too much. Check out the cross country flight (LA to NYC) that happened right after Skip Winter 2012.

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