STR Conferences: Are They Worth It and How to Get the Most Value

Introduction

Jasper: What is up everybody. Welcome back to another episode of Get Paid for Your Pad. Today we are doing an episode of Rev Up, where we talk about revenue management. I am going a little bit off topic today just because I have been receiving a lot of questions about short-term rental conferences. I have mentioned a couple of times on this podcast that we go to a number of conferences every year, and people are wondering whether it is worth going, which conference they should go to, and how to get the most value. I wanted to share some insight today on those topics.

I just got back from GuestyVal in Madrid. I am currently staying in Ibiza with a friend before we settle down in Valencia. The next big conference coming up is the VRMA in Nashville, where I will be present along with a few of our team members. We are going to have around five or six of us there.

Is It Worth Going to a Conference?

Jasper: The answer is not simple. It really depends on what your goals are and what you are trying to get out of the conference. But I can tell you what I have found to be the most valuable from all the conferences I have attended. The first conference I went to in the short-term rental industry was Airbnb Open in 2014, organized by Chip Conley. That was back when you could still walk up to Brian Chesky and talk to him. That is how small it was. I have around 12 years of conference experience, and I have always found a lot of value.

Get on Stage

Jasper: The biggest value you can get at a conference is to try to be on stage. One of the biggest lessons from my business mentors is to be the wheel, not the spoke. Be the center. Be the person who is putting themselves out there and driving value. The more value you drive, the more value you get back.

Being on stage is valuable for multiple reasons. First, you save money. You usually get a discounted ticket or a free ticket. Once you build up your speaker reputation, they might even pay for your accommodation. Second, it is typically easier to connect with people after they have seen you on stage. People automatically assume you are an expert. They give you more credibility. It is also easier to connect with the other speakers and presenters, so you are a little more of an insider. Third, think about the marketing. Being on stage once gives you a lot of credibility. You can put pictures on your website and show potential management clients that you were speaking at a major industry event.

Most people underestimate their chance of being selected to speak. We have encouraged quite a few clients to apply for a speaking slot or a panel, and a lot of them succeeded. You do not need to be the biggest company or the biggest expert. You just need to have something to bring to the table. If you have experience in your business, you have insights to share with the broader audience. The first step is realizing you have value to bring.

Most conferences have a place where you can apply. If you are planning to attend a conference, I would always recommend seeing if you can apply for a speaking slot or a panel position. Why not? You might not get chosen, but if you do, your conference experience immediately improves dramatically.

Be Prepared

Jasper: The second most important thing is to be prepared. A lot of people sign up for a conference and just show up without thinking about what they are trying to achieve. There are a lot of different things you can do at a conference. There is education, there are vendor meetings, and there is networking.

The general sessions are usually the least valuable thing you can get from a conference. The information is typically available online. The real value is in the personal connections. Follow up with the people who ran sessions that interested you. Connect with them in person and learn more from them directly.

A lot of people miss the ball because they are too passive. They sit in their comfort zone, attend sessions, take notes, walk around, and do not really talk to many people. Going to a conference is a big investment. The ticket is expensive. You have to travel, take time away from your schedule, book accommodation, and spend money on food and everything else. So do not just go for the sake of going. Really think about what you are trying to learn, who you want to connect with, and who the people are that will be most valuable for you to meet.

Push yourself to make those connections. Go up to the people you want to connect with. Many conferences including VRMA have apps where you can schedule meetings with people in advance. I already have a bunch of invites on my calendar from people who reached out before the event.

Be careful about vendors, though. A lot of vendors are very aggressive about getting appointments. You do not want to spend the whole conference getting pitched by service companies. Protect your time.

Protect Your Energy

Jasper: Conferences can be pretty exhausting, especially if you are really trying to make the most of them. Make sure you are well rested. Do not go to bed too late. Do not drink too much, because you are going to need the energy to connect with people. There are always a lot of parties and that is fun, you meet a lot of people at parties too. I am not telling you not to go. Just keep in mind that if the conference is two or three days, you are going to run out of energy quickly.

Which Conferences Are Worth It?

Jasper: VRMA is probably the most valuable for most people, just because it is the largest one. There are anywhere from 2,500 to 3,000 attendees, and pretty much every established vendor in the industry is present. There are also a lot of operators. The short-term rental business can feel a little lonely sometimes, and connecting with other operators is one of the most valuable things you can do.

Regional conferences are better if you want to create a local operator network or a small mastermind group. The IMN conferences are a little more investor-focused, whereas VRMA is focused on people who manage properties for others.

For European conferences, there is a big one in Lyon in France in early October, and conferences in London, Barcelona, and Skillfest. I am going to try to attend a lot more of the European ones in 2027. This year has been tough because I had a baby and traveling with a baby is hard. GuestyVal and VRMA are the only ones I am attending in 2026.

Freewyld Foundry at VRMA Nashville

Jasper: I want to talk a little more about VRMA because we are going to have a pretty big presence there. I am doing a workshop on how to build an AI revenue management agent, which I am very excited about. We are leveraging a lot of AI in our business to help our revenue managers make better pricing decisions. The workshop is on Tuesday at 11:30 AM.

We are also doing a surprise in-person event on Monday night. If you are going to be at the VRMA, let me know and I will send you an invite. It should be a lot of fun.

We also have a booth where we do free revenue reports. You can walk up to our stand and we can create a revenue report for you within 10 to 15 minutes. We download all the data from your pricing tool, analyze your portfolio using our AI tools, and tell you exactly where we think you are leaving money on the table. If you are going to the VRMA, look us up. I think we are in front of the wellness center.

Closing

Jasper: That is some general information, because I have gotten a lot of questions on this topic. Going to a conference is a big investment, so my biggest piece of advice is to be prepared. Do not just show up and walk around. Have a plan for what you are trying to get out of it.

For me, it is not just about what you learn and the people you meet. It is also just inspiring to be at a conference. There is so much energy, so many people, so many new ideas. When I get back from a conference, I am always super fired up and motivated. Business is hard. Sitting there by yourself putting out fires every day can be demotivating. Every now and then, going to a conference, meeting new people, talking through your challenges, and getting feedback is a way to make the business more fun and more inspiring.

If you are going to the VRMA, let us know. We would love to meet you in person. And if you have questions on conferences or want to learn about something specific on this podcast, feel free to email me at jasper@freewyldfoundry.com.

If you are looking for help with revenue management, you can go to freewyldfoundry.com/get-started for a free audit where we analyze your entire portfolio and point out where the biggest opportunities are.

Thanks for listening. See you next time.