4 Things Every Entrepreneur Retreat Needs

The last weekend of January, I hosted the first-ever SPACE Retreat in the Great Smoky Mountains.The retreat sold out, and I want to share what I learned from the experience before I forget what it’s like to not know what I now know.SPACE Retreat came about because my wife’s close friend, Carrie Jo Pinckard of Texture Photo, was hanging out at our house one Sunday night. She had attended a $1500/person retreat outside of Atlanta for businesswomen.I said, “I want to host something like that,” and Carrie Jo responded, “Why don’t you?”Shattering the Permission Paradigm.

We need people in our lives brave enough to strip us of our excuses.

Photo Credit: JJ Thompson via Unsplash

Most of us come out of school systems that reward compliance, rote memorization, and regurgitation. We get As for following the rules, not for following our curiosity. We get pats on the back for producing good answers, not good questions. We receive awards and accolades for coloring inside the lines, not making mistakes. You don’t give a public performance until you’ve learned the scales, right?This type of education works for a while, but then we grow up. Without report cards, diplomas, or graduation ceremonies to give us our bearing, we naturally seek out affirmation and rewards from new authority figures.Soon enough, we learn two things:

1. Though degrees and training matter in professions like law, medicine, and engineering, they count for less in other fields.
2. Plenty of people without the right credentials make it to the upper ether of success in the business world.

They didn’t wait to accumulate knowledge, gain experience, and develop expertise. They didn’t ask for permission. In fact, depending on the industry, your boss might be a high-school drop out.Yet, here we are, all grown up, with no parents, teachers, or coaches to evaluate our performances. We’re waiting for someone to tell us we’re ready.

What’s stopping you?

Probably you. The only person stopping you is you.Shatter the Permission Paradigm and go for it. Start. There’s no certification process for most of the things that you’d enjoy doing. There’s only starting and not stopping.No matter how many years pass, I still need to give myself permission to try new things. It’s okay if I’m not good at them. I can laugh at my mistakes, and enjoy myself despite my failures. The only thing to do is take the next step.Why don’t you?With the first SPACE Retreat, I brainstormed a list of about 60 executives and entrepreneurs who might be interested. I put their email addresses in the BCC field, and I sent an email.A bunch of interesting things happened after that:- People said that yes, they were interested in paying to be a part of my experiment.- People said no, they had scheduling conflicts.- People said nothing at all.- My friend John gave me a $50 bill, and said, “God told me to give you this. I think He believes in you and your idea.”After this little bit of market research, I had a choice to make: to book or not to book?By choosing to book, I met with more details and decisions:

• My wife Megan helped me pick out a big cabin above Gatlinburg, and I booked it.
• Jackson Mountain Homes gave us a third night for free.
• Ben at K Brew taught me how to make better coffee and gave me a checklist of the best equipment to buy.
• K Brew owner Michael LaMacchia special ordered five pounds of Evocation Peru Cajamaca for me.
• Jon Longnecker of FortySeven Media designed a beautiful logo and two stickers in less than twenty-four hours.
• I booked a Clarity call with Jayson Gaignard, and got the full scoop on his Mastermind Talks event, which sells out months in advance.
• People flew in from California, Oklahoma, and Florida. They drove in from Boone, Memphis, and Nashville.
• Melody Ratliff of Flips Batter Bar helped me create a menu and signed up to cook all of the meals.
• Megan served as Melody’s sous chef, and did an inordinate amount of chopping and cleaning.
• My parents took care of Salem and Theo for the weekend.
• When my friend Colin couldn’t come, he nominated Bennett.
• And Carrie Jo came to capture the event with her camera, which was apropos.

It takes a village to raise an idea.

Photo Credit: Mitko Pigoff via Upsplash

So many people gave time, money, and creativity to make the first retreat beautiful.I ended up doing a second SPACE Retreat in late March at Carlton Landing outside of Oklahoma City.What follows are some insights gleaned from both experiences:

1. Do what you want. Organize an event that you would want to attend.
2. Keep your team small. Get too many people involved too early, and all of those cooks in the kitchen will likely turn your event into something that doesn’t quite match your vision.
3. Hand-pick the first batch of people you want to be there. They will help create the culture.
4. Offer partial scholarships, but no free rides. Everybody has to pay. They must literally buy in to the experience.
5. Sweat the small staff. Pay close attention to quality: food, drink, people, conversation, location.
6. Delegate taking photos and capturing video to someone else.
7. Delegate food and coffee prep to someone else.
8. Pay your team well even if that puts the event in the red.
9. Focus on creating a deeply meaningful experience, not on making money. The money can come later.
10. Minimize your use of technology. Get people off their phones and computers. Pass out journals and pens instead.
11. Tell everyone the House Rules. One of my rules was keeping screen time to a minimum over the weekend.
12. Sprinkle in fun and adventure. We did a tasting with six obscure, world-class whiskies.
13. Keep any programming “lite.” Weekends are for resting and replenishing, not for another huge to-do list.
14. Come prepared with a list of icebreaker questions to help create meaning more quickly. The two open-ended questions I asked on Friday night at dinner were a) “Why did you come?” and b) “What do you want to take away from the weekend?”
15. Use any communications before the event to set expectations. I wanted people to show up looking for ways to give, not get.
16. Have a refund policy. Life happens.
17. Be hard to offend. The people who you think will fall over themselves to support you may not come. They’ll have their reasons and excuses. Give everyone the benefit of the doubt
18. Don’t disclose the guest list in advance. Maintain some mystique.
19. Start small. The first SPACE Retreat had only 15 spots.
20. Test all payment and/or ticketing apps thoroughly. PayPal gave me some trouble, and this caused mild frustration.
21. After the event, share everyone’s contact information. I put it all on a Google Doc, along with everybody’s picture.
22. Nail down a date for the second event before the first one starts. That way, you can pre-sell spots while people are still at the first event.
23. Use the photo and video from the first event to sell the second one. The video from Brennan Dunn’s first DYFConf is a good example of this.
24. Be generous with your money and creativity. Look for ways to make the event more memorable. I bought my favorite Shinola journal and EnerGel Alloy pen for everyone. The two items cost me $20 per person, and the coffee beans and equipment were over $300. Do you know what people commented on? The coffee, journals, and pens. My friend Carter Thomas made two drone videos for his seminar in Hawaii.
25. Don’t let anyone turn your retreat or meetup into a pitchathon. And don’t be afraid to tell someone to change their behavior. It’s your event. Everyone needs to be cool and play by your rules.

So why not you?

If you want to do stuff, surround yourself with doers.If you want to finish what you start, surround yourself with people who value finishing.If you want to make a habit of trying new things, surround yourself with curious, outgoing people.Finally, if you found value in this blog post, please sign up for my weekly newsletter. I’ll send helpful freelancing tips your way.