How to Create a $50K Retreat

Nail Art

Have you ever dreamed about throwing your own live event?

Do you like the idea of getting paid by people to attend an event that you organize (and maybe get paid to travel too)?

If so, listen up.

Just 18 months ago, the idea of having people pay me to attend an event I organized would have been crazy.

I had as much chance of filling my own retreat as I did getting chosen in the first round of the NFL draft.

Flash forward 18 months and I recently got back from Austin, Texas where I organized — along with my amazing co-founder Jeremy Weisz — a sold out (actually oversold) 2 day retreat for entrepreneurs that brought in about $50K.

entrepreneur retreat

I’m still on a high from the event. We had people fly in from all over the U.S., two from Canada, and one attendee flew over all the way from China.

And best of all, we got incredible feedback from the attendees.

John Lombard, who came all the way over from China, said it was well worth the 50+ hours of travel (longer than the event itself).

Two attendees even said the event was better than their weddings.

(I won’t say which two; and I hope they didn’t tell their spouses when they got back home.)


But it wasn’t all smooth sailing. In fact, at multiple points in the journey, I was ready to give up entirely.

So why did I go to all the trouble? Because I truly believe in a larger vision of bringing together other like-minded entrepreneurs who believe when they give, they are going to get.

And being the person who brings together other people face to face is one of the best ways to build relationships, grow your business and increase your revenues.

I want to show you that it is very possible to throw your own live events, and exactly how you can do it.

In this post, I want to share some of behind the scenes work that went into creating my first sold out two-day retreat and share specific tips for what you should do (and not do) if you like the idea of throwing your own retreat, event or mini-conference.

What Worked Well and What Didn’t Work Well

This event was a total failure before it was a total success.

Back around May or June of this year, my cofounder Jeremy and I began talking about throwing a retreat for a dozen entrepreneurs around November. Our vision was to create a very high-quality event with a great experience for the attendees.

During the event, we would have one part 5 minute talks, (kind of like mini-TED talks) and one part extended “hotseats” where the participant gets feedback from the rest of the smart entrepreneurs in the room on their business.

After looking nationwide, we found an excellent location – Travaasa Austin, about 30 minutes outside of Austin. It had everything – proximity to a cool city with a lot of entrepreneurs, great food, on-site activities, and beautiful 4-star accommodations.

And I had always wanted to visit Austin but had never been there before, so I figured throwing my own event was a great excuse.

At first, the progress was very slow. We had probably hundreds of calls and emails with prospects but most people told us it sounded great but they couldn’t come for one reason or another.

To be totally honest, about a month out, I was getting pretty dejected about this event. We didn’t have a lot of people signed up and I’m a pretty cautious person, so I was talking with my co-organizer Jeremy Weisz about whether we should pull the plug.

I had every typical doubt creep into my mind:

  • maybe we were charging too much
  • maybe we bought off more than we could chew
  • maybe we should have chosen a larger city, like San Francisco or New York
  • maybe we needed more speakers
  • maybe I needed to grow my platform a few more years before throwing my own live events
  • maybe I was too big for my britches

Fortunately, Jeremy was always there to talk me down off the ledge, and he kept joking that we were going to “burn the boats” and not look back.

Ultimately we simply did burn the boats. We decided we wouldn’t take no for an answer. We were going to throw this event, even if we only got a few people to show up.

One of the turning points was when I booked my plane flight. It was a subtle thing, but it was a commitment both to the event and to myself to go through with it, even if I was scared of what would happen.

entrepreneur retreat 2

A short while later, we started getting people saying yes. I remember when we passed the point of break even and I realized we would definitely make some money on the event. That was really satisfying because I knew making the commitment to burn the boats helped tremendously.

So here are my top 10 best tips for throwing a successful retreat or mini-conference:

1. Create a Minimum Viable Event First

entrepreneur retreat 3

The Austin retreat wasn’t our first event. We actually threw a smaller, shorter one day event in San Francisco back in April. We charged just $250 for a one day event.

For this Austin event, we charged $4,000. Big difference, right? We 10X’d the price.

But the first San Francisco event allowed us to test out some ideas with lower consequences if things went wrong. It also gave us a vision of what we could accomplish with a longer, much higher quality event.

That April event helped us learn that many of the attendees were interested in a higher quality experience with more opportunities for the entrepreneurs in attendance to connect and bond with one another.

The additional cost to attend meant a higher level of commitment from the attendees and also we could provide a higher quality experience for everyone.

Fabulous relationships come from fabulous shared experiences.

2. Build an Email List

If I do an 80/20 postmortem, then the fact is really the best thing I can do to fill future live retreats is to grow my email list, because I think about 10 or 11 of the 13 attendees came from my email list.

It’s ironic, but building an online business actually helped me fill live offline events. So if I want to do more live events, my best chance of having them be successful is to build an online presence.

3. Get Feedback on What Your Ideal Attendees Would Want Out of Your Event

This may not seem revolutionary, but one important step we took was we got on the phone with people who fit our target demographic.

No amount of Googling or internet research will give you as much insight as simply getting on the phone and having a conversation with a prospect about what they would want and what they would pay for.

entrepreneur retreat 4

Ask about everything — what events they’ve been to and why, what events they’d like to attend but haven’t, what size event they prefer, what they would want to do, etc. etc. These conversations were invaluable as we put together the framework for our event.

4. Invite Special Guests

(L to R: Ryan Levesque, Dr. Jeremy Weisz, John Corcoran)

(L to R: Ryan Levesque, Dr. Jeremy Weisz, John Corcoran)

We didn’t want to have traditional speakers, but we did want to “pay forward” the opportunities Jeremy and I have gotten by introducing the attendees to some of the VIPs in our networks. So we lined up some well known people as our special guests. We lined up Noah Kagan, Ryan Levesque and Ryan Holiday and Genius Network CEO Dan Kuschell.

We’re really grateful they came, and it really helped to give our new event credibility. A number of the people who came were probably persuaded to come by the fact that these special guests would be there.

But you can’t get VIPs to show up based on charity. Each of these guys came because Jeremy and I had already spent a ton of effort helping them, and because we created an interesting event at a fabulous location.

5. Allow Ample Opportunities for Attendees to Bond

entrepreneur retreat 5

As I mentioned, one of the biggest pieces of feedback from our last event was people wanted more opportunities to bond with the other attendees. And you do that by getting out of the retreat meeting room and doing activities together.

We intentionally started the event with a reception and dinner the first night, which gave everyone the opportunity to get to know one another in a more casual environment before starting work the next morning in the retreat meeting room.

I think organizing this dinner the first night helped to accelerate the process of people letting their guards down and being more comfortable with one another.

Next time, I think we could provide even more opportunities for our attendees to get to know one another better outside of the meeting room.

We had one separate bonding experience in Austin – a cooking class. But it came at the very end of the first full day. In the future, I would have an activity midday or perhaps on the morning of the first day.

As an organizer, you want to provide a ton of value to your attendees who are paying a lot of money to attend your event. However, you can take that too far by trying to cram in too much time in the meeting room. I found people could build connections and find value outside of the meeting room just as much as they did inside of the meeting room.

6. Be Different

be different

There are a lot of retreats and events aimed at entrepreneurs, so you need to differentiate yourself. One of the ways we did that was by being clear we were going to be ourselves.

Jeremy and I were comfortable being goofy and joking around, and I think this helped to break the ice so that everyone felt comfortable letting their guards down and opening up and being honest and a bit vulnerable.

7. Require Applications

Rather than allowing people to purchase a ticket directly, we required anyone who was interested in attending to submit an application. We then scheduled “interview” calls to be sure people were a good fit.

(Clockwise from top left: Dr. Jeremy Weisz, Ryan Holiday, Noah Kagan, John Corcoran)

(Clockwise from top left: Dr. Jeremy Weisz, Ryan Holiday, Noah Kagan, John Corcoran)

While this was time consuming, it created an exclusivity to the event such that people who were accepted and came were grateful to be included, and it also helped us ensure the people we invited to attend were a good fit and were going to be contributors.

There were many people who we interviewed and found they weren’t a good fit, so I’m glad we didn’t allow just anyone to attend. And we were able to curate a good balance of skillsets and backgrounds among the attendees.

In the near future, one of my goals is to bring on a coach/salesperson who can take these intake interview calls because it was really quite time consuming. We will most likely look for someone who has attended one of our events already or who has gone through one of my programs like Connect with Influencers or Webinar1K or one of Jeremy’s programs. (If this is of interest to you, please email me.)

8. Have Fun and Delight your Attendees

One thing which was really fun was thinking of ways to surprise our attendees. We had a few tricks up our sleeves, and I think it kept people guessing and surprised.

For example, the closing dinner and party was at a special location on the grounds of the resort, but a distance away from where we had been hanging out the previous two days. We loaded everybody up in golf carts and drove them to the dinner location, through some trees into the woods. The golf carts then pulled up on a stone structure which looked quite old but which was actually new.

We then had a beautiful cocktail reception, followed by dinner inside a stone “temple.”

Here’s the cocktail location:

entrepreneur retreat 7

Here’s a brief video to give you a small taste of what the dinner was like:

After dinner, we had Noah and Ryan give brief talks to the group. They were both great, and Noah was hilarious – he just cracked everyone up for about 20 mins.

Then it turned into a 90-minute long big group Q&A session and discussion. It was like an amazing dinner party with some of the smartest people you know. Really a big highlight of the entire event.

In the future, when we promote our events, we’re going to better highlight this culminating “Roundtable” after-dinner discussion because people really seemed to enjoy it.

So the bottom line is… keep a few surprises for your attendees up your sleeves.

9. Get Clear on Your Ideal Avatar

One of the things Jeremy and I did early on was we tried to get clear on exactly who we wanted to attract to this event.

Ultimately we decided our best customer was someone similar to both of us – a 35 to 45 year old entrepreneur with a family running a business that does multiple six figures or 7 figures or 8 figures, with a background in a “service-based” business but who is interested in leveraging their impact using online tools like blogs, podcasts, webinars, etc.

Having this clear understanding of our ideal attendee really helped us to zero in on who this event was for, and who it wasn’t for.

10. Allow Enough Opportunity for Testimonials

If you have faith in what you’re doing, then people will appreciate it and find value in it.

I think we didn’t have enough faith in what we were doing because we had a videographer to capture testimonials, but it turned out we didn’t have enough time to get testimonials from everybody who wanted to give one. Next time, we’ll have two videographers so that we have enough time to capture everyone.

Here’s some of the feedback we got after the event:


feedback2 feedback3

What We Would Do Differently Next Time

Our goal is to ramp up these events until we have one event per quarter in various locations such as San Francisco, San Diego, New York, Austin, Chicago and/or Hawaii.

And of course, we want to constantly be improving.

So here’s what we already know we will do differently in the future:

  • Bring on a Coach/Salesperson. One of the most time-consuming chores was doing the intake “interview” calls. I’d like to hire someone to handle these interviews so that we can focus our time on improving the quality of the event and so we can do more events.
  • Systematize Planning. We need to create a repeatable formula for planning these events. Right now, I am documenting the steps we took – from the criteria for future venues to when to order 3-ring binders to be delivered directly to the resort.
  • Create a Fabulous Experience for the Special Guests. For small events like these, it’s not economically feasible to pay big speaker fees. So if we want to attract A-list special guests, we need to create a fabulous experience for the special guests – something they cannot get elsewhere. A big part of that attraction will be the curated group of entrepreneurs, but we can also create real buzz for future special guests by wowing our special guests with a great experience.
  • Find a Location We can Come Back To Again and Again. For each quarterly event, we need to find a venue that works and is flexible so we don’t need to reinvent the wheel every time.

Bottom line: I feel almost guilty that I enjoyed this event so much. Of course, leading up to it was not a walk in the park and it was touch and go for awhile, but getting to hang out with driven, smart entrepreneurs for 2 days made it all worthwhile.

I get really excited thinking about all the cool locations where we can have these events in the future, and I’m incredibly grateful we’ve had people interested in attending to make them possible. Hopefully this post has inspired you that it’s worth the effort to create your own event, if that’s something that interests you.

So, when are you going to organize your own event? I’d love to help. Feel free to leave any comments or questions below.