MBA2136 What I Learned From Hosting a 4 Day Event
2 Feb 2026 · 14 min
Omar Zenhom hosted OSCON, a four-day invite-only founders' retreat focused on intimacy and organic conversation. He chose skiing as the shared activity, ran the first year at cost to test the model, and learned hard lessons about transport, food, and staff shortages. He's running it again.
Questions this episode answers
12
Planned over 18 months prior
Four days
Skiing and snowboarding
A short season of three months
Chapters
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Hey oh welcome to the $100 MBA Show. Powerful business lessons you can count on every single day with our daily 10 minute business lessons for the real world. I'm your host, your coach, your teacher Omar Zenholm. I'm also the co founder of Webinar Ninja, an in demand software company I started with my co founder Patrick back in 2014 and in today's lesson you will learn what I learned from hosting a four day event. Yep, this past August I hosted a founder's retreat called oscon. Me and my partner Cole actually planned this retreat over 18 months ago, but because of COVID it got postponed to this year and boy am I relieved that I pulled it off. This is the first time in a long time I ran a live event. Plus, we're just coming off the back of COVID restrictions and there were a lot of curve balls along the way. I'm going to share with you what I learned in the process. What are some of the challenges that I faced, what are some of the surprises and delightful things that made it a successful event and why I can't wait for the next one. This episode is all about sharing what I learned along the way while it's fresh in my mind so that when you plan your next event, whether it's big or small, you have the insights and strategies to make sure it's a huge success. So let's get into it. Let's get down to business.
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Before I jump into all the insights and things I learned along the way pulling off this four day event, let me describe what it was. Nicole and I wanted to create a special event that's a little bit different than the ones we're used to going to. Most of us are used to going to big conferences where we meet hundreds if not thousands of people. We usually have to fly 10, 15, 14 hours away. If you live in Australia, by the end of each day of the event, you're usually exhausted, your dogs are barking, got sore feet, you got a sore back and you need like a week off to recover from a typical event. We didn't want to pull off an event like that. We want an event that actually got people to feel recharged, feel renewed, with a new perspective. A retreat for busy business owners that don't make time for themselves to recharge their batteries and meet interesting people. I wanted the attendees to meet people and get to know them on a deeper level. I really was tired of kind of meeting people at conferences and it was just sort of shallow conversation and really don't get to know each other as friends. So that was the genesis of the idea of OSCON, where we wanted to make it purposely small. Only 12 founders for the first time around. And the reason why we kept it small so that you have enough time to get to know people over the four days. Two we wanted to make it intimate and sort of private so you feel comfortable being yourself. And lastly, we didn't want to chock full of sessions. We wanted organic conversations. We wanted it to be fun. We wanted it to be relaxing and just something that you look back on and say, man, that was one of the best few days this year. As entrepreneurs we're busy. We don't have time to plan these types of things for ourselves or curate a group of people that we could do it with. So Nicole and I decided to create this event ourself. It's an invite only event and we wanted to make sure that we had the right people in this group. And that's the first thing we learned, is that the crowd, the attendees of OSCON really is what made it a success. Having the right people with the right dynamics, from different backgrounds, from different businesses or offerings, offering different types of insights, really made it a rich experience. It's the one piece of feedback we got over and over. So I made a note of it. I made a note that next time around, when we plan next year's, it's imperative that we make sure we choose the right people. People that we know well and we vet and we know will jive with the rest of the group. This is quite difficult. We got lucky the first time around, but it's so important because the people around you in an intimate setting, like a retreat for four days, it's gonna affect your experience. The second biggest takeaway is that we did OSCON around the activity of skiing and snowboarding. Yes, there's skiing and snowboarding in Australia. It's a short season of three months, but it's pretty fun and epic. Now the reason why is because of a couple things. One, we wanted to have a shared experience. We wanted to create a shared experience for the group that wasn't all consuming, meaning it allowed time for people to have conversations, side chats, get to know each other. And skiing and snowboarding is great for that because you're not skiing or snowboarding constantly, right? You are stopping, you're going down the hill, you rest halfway. Once you get down, you're waiting in line for the lift, you're talking on the actual lift, you're having lunch on the mountain, all that kinds of stuff. So we wanted an activity that would allow for that. And snowboarding and skiing was just perfect. Now this is the thing about niching. We realized that, hey, if we choose something like this, that means people that don't like snow or don't know how to ski or snowboard may not attend. That was a trade off that we were willing to make because of how effective this activity was for the purposes of networking and bonding and building relationships. Now mind you, there were a handful of people at the event that couldn't ski or snowboard. But they learned and that in itself is an experience they bonded over. At the end of the event, we did a feedback survey from all the attendees and this concept, this activity ranked the highest out of all the activities we, we did. People loved it and can't wait for next year. So it's Important when you run your event to survey your crowd to know what they enjoyed, what they did and how you can improve. But I find that the survey actually served best because it told you where to double down. The survey tells you, hey, you're doing this. Well, don't stop doing this. It's really what drives the experience forward that leads me to the next takeaway at the last day or the last night of the event. Before we started to play a game, we took about 20 minutes to ask everybody who's attending the event to do the survey. The feedback survey. It was an anonymous survey that we made on Google forms. It was quite short, it was about like six or seven questions. And the questions ranged from ranking the different activities, what they liked the most, what they liked the least, open feedback, ranking the experiences of some of the logistics like the transport and the hotel and the food, and we'll get into that later. But we actually got them to do the survey then and there. I didn't want to just send them a link and say, hey, do this whenever you can. I run events and I've done that before and that's a mistake. Take the time, make their survey short so they could do it in 10 or 15 minutes. And what we did, we just literally said, here's the link. We send it to our Slack group, complete the survey right now. Just gonna play some music in the background, enjoy some crackers, some chips, some cheese, a drink while you're doing the survey. And it was just part of the actual schedule. And in 20 minutes I had all the survey answers in the Google sheet and I didn't have to chase anybody down. Pretty cool. And I'm so glad we did that. Now I mentioned logistics. This event was not easy to pull off from a logistical point of view for several reasons. One being that we're in the post Covid era right now, hopefully. But more importantly, because of this, there's a massive shortage of team members and staff across all different industries. In hospitality, for example, we had two bookings with different bus companies with drivers to drive us down to the mountains. It's about a seven hour hour drive from Sydney to the snowy mountains. This is included in their ticket, they get transport and we were all set to go with a driver, with the van and I was going to get to relax and enjoy myself. But one company in the span of the time we announced the event and when the event actually happened, went out of business. Covid the other company had a staff shortage and had to cancel our reservation and that happened really late in the game, I still had a backup plan, which is like, hey, let's all take a Greyhound bus. But those tickets were sold out. But I had a backup backup plan, which is not ideal, but it got the job done. I rented an actual minibus and drove it down. Yep, we're talking about a minibus with a trailer for all the luggage and equipment. It was a lot of fun, but it was tiring, to be honest with you. And I was hoping that I can spend time with the attendees and get to know them. And in fact, one of the pieces of feedback I got was, we wish we spent more time with you and Nicole, but you guys were very busy organizing things, understandably. But it's something that they would want for next time around. So logistically, the bus drive was a lot of responsibility. Luckily, it was very smooth and it was probably one of the highlights. People actually said this is the hidden gem of the event is spending time networking and talking to people on the road trip down and back up. But I'm glad I had some backup plans because of the COVID staff shortage. On the flip side, we chose the best hotel and accommodation, which were like chalet in the mountain that we could find in the area. And that paid off. Why? The staff was brilliant. They had our rooms ready. They were organized. They had the bed configurations correct. They gave us enough keys for everybody. The breakfast was brilliant. From the accommodation standpoint, it was amazing. And it's because you get what you pay for. So when you're running an event, don't go cheap on the important things, like the venue, like your actual accommodations, if it includes accommodations. This is where you're going to spend most of your time. This is where the event actually is being held and where the members are going to be made. Make sure it's brilliant. It's well done. I made sure on TripAdvisor, it had amazing reviews. I'm a big fan of TripAdvisor. It's never wrong. So I'm so glad we did that. So the next time around, I'm going to make sure we do the same. What else? When it comes to logistics, food, one of the things that we did is we took an intake form where we asked everybody for their dietary restrictions. There were a few people that had some difficult dietary requirements, but for the most part, we were able to accommodate for it. But we could have done it better. We could have done a better job with it. We did well when it came to the meals and the restaurants because we contacted these venues in advance, but we didn't do so well when it came to the things that we catered, like the snacks, like the drinks, we could have done much better asking people what they prefer to eat. When it comes to those things, we just made decisions on their behalf. There's a ton more I can talk about when it comes to the logistics, but let's keep it moving. What else did I learn? Well, let's talk about price point. I made it very clear to everybody that this is the first time we're running oscon and it's going to be an MVP version, minimal viable product, meaning we're going to do our best to create a great experience, but we're going to do it at cost, meaning we're not really going to make a lot of money. We're going to try to keep the margins kind of thin, so that way we just pull it off and learn from it. Luckily, we negotiated a lot of deals when it came to the hotel, we booked way in advance to make sure we get the best price. We negotiated deals with restaurants and eateries. When you book in advance for lift tickets and all that kind of stuff, stuff, you save money. So we were able to kind of do a really good job with budgeting and for the most part we weren't that close to budget, meaning there was some breathing room, but there wasn't enough room to make it extra special. Now everybody loved it, great feedback. They said it was an amazing experience. But I'm a professional, I want to make even better. And the reality is if I want to take things to the next level, I'm going to have to charge more next time around if I want to take on some of the feedback that people gave me about what we can add or do better. It's going to cost money and you have to realize it's okay to charge. It's okay to charge a bit more. It's okay to charge because people are happy to pay, knowing they're going to have a fantastic experience. Especially for events that are four days, five days they're going away, it's like a holiday for them. It's like going on a packaged tour. If you ever see those package tours, they're not cheap, they're 5, 6, 7, $10,000. And for good reason, because there's a lot of that goes into them.
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Before I wrap up today's lesson, I want to give you a few more takeaways that I learned from pulling off a four day event. I'm going to go down a road most of us don't want to talk about, but it's liability. You got to make sure you got yourself covered. Hopefully nothing will happen, but make sure you have some sort of public indemnity or some sort of insurance. When you run an event, the easiest thing to do is just call an insurance company and say, hey, I'm running this event. These are the dates, this is the venue, this is what's going to happen. Can I have insurance for this event? And they'll give you an estimate. It's actually not that expensive. In addition to this, we had everybody sign a waiver that releases us of any liability. After all, they're going on a trip, they're traveling, there could be accidents, they're going skiing, all that kind of stuff. So this kind of protects you in both ways. And everybody's gonna understand that that's how it's gotta be. My last takeaway was how much fun I had. Not just at the event itself and getting to know all these amazing entrepreneurs that I became really good friends with now, but even during the planning, even leading up to it, I realized I enjoy doing this. It's like throwing a big party for some friends. And it reminded me how much I love doing events. And I said to myself afterwards, hey, that was a lot of fun. And I told Nicole, what do you think? Do you want to do this again? Did you enjoy it? And she actually did more than she actually expected. And we said, let's commit ourselves to doing this again. Let's run it back, let's do it again, let's improve it, let's make it even more amazing, and let's have fun in the process. It's important for you to recognize when you enjoy something in your business, when something is less of a slog and less work and just something you really kind of want to work on all the time, that's a green light. That's something that you want to pay attention to because you can really do well and monetize and grow something that you have a passion for. Thanks so much for listening. I hope you loved this episode and learned from my experience if you want to check out what OSCON was all about, you can go to OSCON co. We're already planning next year's and having a blast doing so. If you love this podcast, leave us a rating and review. Let us know what you think of the show. We read every single review so we know what you love so we can keep on doing it. Before I go, I want to leave you with this. The magic of live events is that you're in the memories making business, right? You're helping people make incredible memories. You're giving them incredible experiences and that has such a deep emotional effect on them. When you have a great experience, you have a great party or event that you attended, you can't help but talk about it, can't help but think about it and want to go to the next one. So if you're thinking about starting your event, you don't have to start with a four day event with all those logistics and travel and all that kind of stuff. Like me. You can start with a small meetup with an afternoon with a one day event in a local CO working space. Make it fun, make it a blast, make it an experience they'll never forget. Thanks so much for listening and I'll check you in tomorrow's episode. I'll see you then. Take care.
Is it time to reimagine your future? The right business skills may make a difference in your career. At Capella University, we offer a relevant education that's designed to focus on what you need to know in the business world. We'll teach professional skills to help you pursue your goals like business management, strategic planning, and effective communication, and you can apply these skills right away. A different future is closer than you think with Capella University. Learn more at Capella Eduardo.
