In this episode of The High Profit Event Show, host Rudy Rodriguez sits down with Daven Michaels, a New York Times best-selling author, global entrepreneur, and master of large-scale event production, to explore what it truly takes to create, fill, and sustain events that both inspire and convert. With a rich background spanning entertainment, outsourcing, and now community-based event leadership, Daven brings decades of experience and a deep understanding of how to blend creativity with proven business systems to create unforgettable experiences that leave a lasting impact.

The conversation begins with The Art and Science of Filling Events, where Daven breaks down the key differences between free and paid events, explaining how pricing directly affects attendance and engagement. He reveals that while free events may attract large registrations, they often lead to an 80% no-show rate, whereas paid events—especially those priced at $97 or higher—see up to 90% attendance. But the real secret, Daven explains, lies in follow-up and connection. Selling tickets is only half the battle; the real work is in cultivating trust through high-touch engagement, confirmation campaigns, and genuine relationships long before the event begins. This thoughtful approach transforms attendees from sign-ups into eager participants, setting the stage for meaningful interaction and stronger conversions.

From there, Rudy and Daven dive into one of the most powerful forces driving event success today: Building Community as the Foundation for Event Success. Daven shares the story behind his creation of The San Juan Social Club, which started as a local gathering in Puerto Rico and blossomed into a thriving community of nearly 4,000 members. That sense of belonging later evolved into the San Juan Social Cruise, an exclusive networking experience that now brings together 500 entrepreneurs and founders for connection, collaboration, and shared growth. Daven emphasizes that we’re living in an age where “community is the new currency,” and those who invest in relationships over transactions naturally build ecosystems that fill themselves. Rudy echoes this by highlighting how strong communities turn events into movements that last well beyond the closing session.

Finally, the discussion turns toward Creating Transformative Experiences Through Relationship and Vision. Daven explains that every great event begins with a clear intention—an emotional blueprint that guides every decision, from venue and design to programming and attendee experience. He draws from his roots in entertainment, where he produced massive 20,000-person concerts, to show that the key to transformation lies in authenticity and connection. When attendees feel like “homies before they even arrive,” as Daven puts it, the event becomes less of a transaction and more of a transformative journey. He encourages event leaders to balance artistry with structure—to combine creative vision with strategic systems that ensure smooth execution and measurable results.

Throughout this inspiring conversation, Daven’s insights remind event leaders that success isn’t about chasing numbers; it’s about creating impact. Whether you’re hosting a virtual summit, live conference, or mastermind retreat, this episode offers the mindset, methods, and mastery to help you fill your events, foster connection, and lead with purpose. Tune in to The High Profit Event Show to discover how to turn your events into powerful platforms that transform lives—starting with your own.

Want to connect with Daven?

Website: https://davenmichaels.com/story/

Facebook: https://www.facebook.com/davenmichaels

Facebook Page: https://www.facebook.com/davenmichaelslive

Instagram: https://www.instagram.com/davenmichaels/

LinkedIn: https://www.linkedin.com/in/davenmichaels/

Hello, and welcome to today's episode of the podcast. We have a super special and fun guest with us today, Mr. Daven Michaels all the way from Puerto Rico. We're both coming from Puerto Rico today. We're like down the road for each other. Maybe half a mile. Yes, it's great to be with you here today, and I'm super excited to have you on today's podcast because you know on this podcast we're interviewing experts who specialize in running highly impactful and profitable live events and you my friend have been in the business for decades. I think three or four decades in addition to being a New York Times best-selling author and a serial entrepreneur. You actually were one of the biggest events. I think you ran Edie was trying to dance, music concerts like 20 or 30 thousand people early in life and you've been running events at various parts of your business models for years even today. You run the same one social club cruise and part of that is an annual cruise on The Virgin Cruise Line where I think this year you're on track to bring, what? 400 people together for an event? 500 people? So you are no stranger when it comes to knowing how to put on an event and get people to show up and have an impactful experience for them.

So this is a great episode guys. Tune in. Make sure you put your pencils out and stop whatever else you're doing. This is one that you're gonna want to listen to and probably go back and listen to again and again. But hey, let's let's jump in man. I'm super curious to hear about your background. You have a super serial entrepreneur, interesting background from the major events to the music world including outsourcing. You outsource the company. Outsourcing company in the Philippines over a thousand employees. What first sparked your experience for the love of events and creating environments where people show up and get connected and take action.

It's great to be here with you Rudy and that's a really good question because I started doing events a long, long time ago, but they were different events than the events I probably did over the last decade but I've always been a showman and even back to when I was a kid doing magic shows in my garage for for my neighbors. I just love the idea of like having this vision in your head for an experience and then actually making it happen and seeing the faces of the people that experience it. I mean they go crazy and they're ecstatic and they're euphoric and that's like my nirvana. People are kind of my nirvana. So just kind of give you a little background of me. Been self-employed for over three decades. Most of my business has sort of been in entertainment communications. But I've also had a kind of a 20-year track record in businesses that were not like that. But I brought my personality and the whole entertainment and communications things to the biz. So like for example, one of the things we'll probably talk about is my last exit which was the company called One Two Three Employee. We were in the outsourcing business. The outsourcing business is call centers. Very highly commoditized business. People just care about price and efficiency, but we sexified that business and it was extraordinary. So in the early days, I guess maybe my third or fourth business, I was the biggest EDM event producer in the US. I throw parties for 20,000 people a night. That was really awesome and then I produced music at television for 15 years and just going on the road and touring and doing all that. I love it.

I'm a showman and then I started a little company. The one that I was just talking about that blew up to a thousand employees and now we're part of a conglomerate with 6,000 employees and I'm on the board of that company and there I mean that was a very different business, but I still got that entertainment out of me because I spoke in 51 countries and we utilize that to sort of grow that business and we'll probably talk a lot more about that today.

Awesome man. I'm curious, how did all that set up the foundation for the kind of events that you run today?

Well, I mean it was all kind of lockstep. So the original parties, I mean those were just blazing parties. I mean they were huge and then we started One Two Three Employee and in the early days of One Two Three, like so many businesses, we marketed one-to-one but it wasn't, and we didn't really see momentous exponential growth in our business until we went from marketing to one, to marketing to many. So I'll kind of give you a little background. So when I started One Two Three Employee, we were first to market, literally reverse market. There was one other company in our space in the early days. We were doing virtual assistant services for entrepreneurs and then later it sprang up into sort of call centers but we still kept that space. We still kept a huge presence in that space and I like to think that when entrepreneurs think about outsourcing they think about One Two Three Employee and so in the early days we were first to market and I would say you can always, a lot of people think that you have a home court advantage being first market, but I always say you can always tell who the pioneers are because they're the ones with the arrows in our back and that was certainly us. Entrepreneurs needed outsourcing. But they didn't want it because they didn't know that it existed for them and so I realized early on that if we wanted to have a market, we would somehow have to figure out a way to carve out that market and create it. So eventually, we decided to adopt an educational model. So I started writing books, eventually became a New York Times best-selling author. Ten books now. We started creating info products. I started speaking on stages all over the globe and we started doing our own events, Australia, US, Europe, Asia, New Zealand. And we began educating our prospects and turning them into clients and that's a methodology that we still use today.

It's pretty common, but back then it wasn't. So event marketing was a huge component of what we did and and from a dollar standpoint, honestly, it probably represented maybe 8% of our business but the branding, what happened from that, was monumental and extraordinary what sort of came of that the byproduct of that we will get into that too.

Absolutely, man. Well, you definitely have a track record of getting people to show up to your events. So whether it's on circuits, business summits or cruise experiences.

Oh, yeah, and also sorry we didn't touch on that. So, I did events for a decade, business events and then we really don't do much of those events anymore. But I started a little group when I moved here to Puerto Rico. Just to set the stage for this conversation, the context where I started a group to sort of bring us expats together with the locals for like food, conversation, networking. Fast-forward many years later. We have nearly four thousand people in The San Juan Social Club and I do events once a month for free as a public service to bring everyone together. We raise a lot of money for charity as well. And then once a year, like you said, we do a cruise on Virgin with about 500 founders from Puerto Rico and beyond. Now ask the question.

Yeah, that's great. You have the track record of the concerts of summits and the cruises. What do you see that most event hosts get wrong when it comes to filling their events? What are those mistakes that you see get made?

Well, it certainly depends on the type of event. The biggest challenge for any promoter, even the savvy ones, are getting butts in seats. It's tough. It's not easy. There's a lot of ways to do it. You can buy traffic. You can hit your list. You can try to get your affiliates to mail for it. I don't know if there are things that entrepreneurs get wrong when they're trying to fill an event. I mean, I suppose if you don't fill the event you got it wrong and that's because you just were not unbelievably tenacious because it just requires so much touch and so much attention, but it's all different. They're all different. So if you're doing a business event, let's say there's so many variables, are you doing a free event? Are you doing a paid event? Do you have big speakers instead? Is it more of a content that pulls people to the event? So I think we really have to talk about more in the context of the event. What exactly is it? There's so many different variables but especially for people that are starting to do events for the first time, it's just not easy to get butts in seats. But I'll give you some thoughts on it. So if it's a paid event, if they pay over $97, they are pretty good. They're gonna show. So you'll probably have 80 to 90 percent show rates.

So, you could charge people. Having said that, for a decade we did free events. Now we had 80% no show, at 20% show because if you do something free and nobody has any skin in the game. So the day of the event comes and they've got meetings and kids and things to attend to and they go, I'm just gonna blow it off because they don't have any money in it. So if they spend $97 or above, they generally show. Having said that though, a lot of people, I'd say the majority of people don't do free events. I'm a big believer in free events. Why? Because we would throw free events and have hundreds of people show up and not pay anything to get in, buy a $35,000 program. So happens all the time and those people might have not come because of the barrier to entry. Even though it's just $100 or a few hundred dollars now, they might have come too. Just unfortunately, you just never know.

That's great man. Inside of that I heard several things that related to tactics and beliefs. One, you believe that you got to be tenacious. You have to. It's a high touch. You got to focus on it.

And sorry to interrupt. But another thing too is once they've registered for the event and you have to have a whole campaign just to make sure they show. It's not enough to just sell them a ticket and think that they're coming.

I couldn't agree more on that.

That's one of the services that we provide to many clients. We call them confirmation call campaigns and at the same time it's a chance for you, as the sales team, to get intel on that prospect and who knows? We had a team once that would call everyone and start selling them before they came to the event and sometimes we would sell somebody a $35,000 package before they even came to the event and the question is why and how. Well we had a great team, but also sometimes people come to your event and they're already pre-sold. They've seen you, they've been following you. They know you have something to sell them and they're kind of like I want to work with Daven. I already know I'm going and they're gonna try to sell me something and I'm gonna buy it. Think you get a lot of that.

I also appreciate the points you made about free events versus paid events and kind of the expectations around that. Hey, free events and get a lot of people to register, and if there's no skin in the game, something comes up. They change their minds. You get 20% to show up versus charging at least $97. You're looking at closer to 80% show up. 20/80 versus 80/20. It's kind of, that's a super important message for the audience to hear because it's important and it's a decision you have to make.

I mean, let's think about that. Okay, so if I get a thousand people to register I'll have 200 show and if you charge $97 you don't have to have a thousand people register. You have to have, I don't know, whatever the numbers is, 80%. Whatever that is, but there's a lot of upside. So again, somebody will come for free and they'll buy something expensive and also, I have a thousand or I have maybe 800 or 600 more people on my list than you do if you were charging but having said that a buyer is ten times more valuable than an opt-in on your list. So there's pros and costs of both and you have to make that decision. But at least this gives you the knowledge to know what's right for you potentially.

Yeah, that's great and actually I'm gonna continue down that thread here as far as a filling event. So many out here insist that filling events is all about running paid ads. That you specifically have run events that have been a little bit more of a pull marketing towards your or I mean I've done it a lot of different ways.

So, we've done paid traffic and paid traffic, lower show rate. We've done, just hitting our list. Once somebody's been on your list for quite some time, it's a lot easier to get them to invest in an event. We also use our joint venture partners. They would mail for us in those scenarios. They didn't know who we were but that affiliate kind of shared their credibility. They showered their credibility on us saying like hey, you should go to Daven's event and then lastly, and my guess is most of you that are watching this probably don't aspire to have a cruise. There's a million events on land and not that many cruises, but cruise marketing is a whole different thing. I don't even think you could run paid traffic to get cruisers. I mean, it's conceivable, but I don't think it would work out financially. Cruising is super high-touch because you're asking somebody to take a week off. If they're in your hometown then you sure they could jump on the boat here. But like for my cruise half the people come from Puerto Rico and half the people come from all over the globe. Those people have to get on a plane, fly to Puerto Rico, jump on a ship with us for a week and then go home, it's a huge commitment for people and it's super high-touch. Like we have to touch the, pardon the French, the s*** out of to get them to come. It's a whole different sale. Like I could have somebody with a hundred thousand lists say hey, Dav I'm gonna mail for your cruise. Great. That'd be awesome. How many people register, about three? It's crazy. That's less than, I mean this is like a .003 percentage or something like that. It's pretty, pretty damn low.

Yeah, so you brought up a good point like marketing, promoting for a cruise's own animals, own thing. It's even, they all are whatever the event is. You're gonna have to have a specific marketing strategy for that event. So for the clue specifically, how do you craft your messaging so that people feel like they have to be there? What's your angle?

We make it super personal that all of our cruisers believe that they have a relationship with me prior to them coming. And that's really key now. Once they come they do have a relationship with me, but we like literally build a relationship. They feel like we're homies before they even jump on the boat. That's the only way to do it. And look, if you can do the same thing for your online event, you're ahead of the head of the game. You're just gonna get more stickiness, higher edge, higher show, higher by I think developing that relationship whether you have to do it or not is a great idea to do. Build a friendship with your prospect.

Yeah and one thing they notice that you also, with The San Juan Social Club, you built a community, right?

Yeah. So I'll take kind of funny story. So I guess I built The San Juan Social Club as a community over the last several years. The cruise next year will be our third annual cruise. Our first cruise we had 238 cruisers. Super high-level groups. Our group did $110 million in deals. Between each other, Puerto Rico's a tax haven so it's pretty cool. Second year 438 or 458 something like that. This year will have 500 and then Virgin has kind of capped us at 500 which is a real bummer. But I'll tell you something. So I had this vision, this idea for a Puerto Rico cruise two days after moving to Puerto Rico eight years ago, but at the time this was five months after Hurricane Maria. The island was in shambles. No cruise ships were even coming to Puerto Rico because Puerto Rico's offline. So the timing was bad, but we had that idea very early on years ago. By the way, I'll tell you my cruise is not an original idea. It was inspired by another group cruise that I've spoken on for the last decade called the Marketers Cruise. Roughly about the same amount of people by the way, it took them 16 years to get to 450 people. It took us 2 which is pretty neat. But it was molded around that. I wanted to create that unique experience for my people. So anyways had the idea a long time ago then built the community not really thinking about it a few years ago. I was like, you know what? Let's do this. I wanted or I want to do this. It was an idea. So I reached out to my booker who's become my partner and he got the itinerary of the contract. We did all the legwork. It was a lot of work, a lot of decision-making because we wanted to go with Virgin. Virgin was in an interesting financial situation at the time.

They're built during COVID. As a result, they had just taken a half a billion dollar bridge loan. I couldn't even get the insurance companies to insure Virgin cruisers. It was very risky. But we really wanted to go with Virgin. So anyways, we finally got it all to work. Finding a schedule, finding an itinerary that would go around the Caribbean was challenging. We just had a lot of challenges. But finally we had a contract in hand. My partner calls me and he said okay, we've got the contract. Are we doing this? Mm-hmm, and I said, I don't know. I don't know because I know that seven out of ten group cruises never see the light of day. People come up with an idea. Hey, we're gonna do this group cruise. They usually don't fly and I felt like if I did this it was gonna be very public and if I fell on my ass everybody would know about it. I just wasn't sure so I said let me take the weekend and let me think about it and I was speaking to one of my dear friends who runs our dev team in India for the last decade, one of my best friends. I was telling him about this and he said to me, he goes, you have to do it. And I'm like, why do I have to do it? He goes because we live in the age of community influencer, thought leader. Call it what you may. He said any time you have like an inflection point, the ability to create community, you have to do it. It's too big an opportunity. And I was like, all right brother. I'm like, all right, fine. Let's go and we took the plunge and it was not easy to get people to take a week off of their hectic schedules from all over the globe and come do this. But then we did the event.

And here's the hilarious thing. I had this vision, and I think this is a good lesson for you event producers, is that when you come up with an event, you have this vision for what it's going to be. Then it either becomes that or it doesn't. I mean, probably my guess is, 8 out of 10 times, if you come up with this idea, you put everything into it, you probably pull it off. And that's extraordinary. It's a wonderful feeling. It's so fulfilling and so I had this idea in my head of what this was going to be, but my cruisers had no clue. They didn't know what it was going to be. They just signed up, you know what I mean? And so on the first day, I go, hey, how many of you, like the roof's full, I go, how many of you, like, think, what did I say? I think I said, like, how many of you have any clue what's going to happen this week? And like, nobody knew. I go, you guys are amazing. You have no clue what this is going to be, but you are in for a treat and then it was extraordinary. It was even better than the plan because when you take this idea, but then you infuse it with energy, from people and love, if you will. Then it's just, it becomes magic. So now I have this magical cruise, which is pretty neat. It's a legacy project too, because it'll probably be around a decade from now.

Awesome, man. It's so cool. Yeah, it's really neat. For someone who's listening to this, and maybe they're considering going out to the cruise, what kind of entrepreneur gets the most out of the cruise?

So I'll tell you what the secret sauce is. So there's two groups of people that are on the cruise. So one is all the incredible people from Puerto Rico. If you don't know, Puerto Rico is a tax haven. It attracts a very high level of founder, people that are doing really well and then just all kinds of amazing, like we have all the movers and takers and shakers in Puerto Rico. So they're extraordinary. They're doing some incredible things, really incredible globally. But then the other half of the group is all the amazing people I've met from speaking in 51 countries. These are all the movers and shakers from their respective countries. These are the people that were on stage with me all over the globe and that has become our secret sauce, the people. So basically our people from Puerto Rico get excited about what the people from all over the globe are doing. All our friends from all over the globe get excited about what everyone in Puerto Rico is doing and we create magic. So we have networking. We have world-class speakers and tons of fun. It's 80% fun and 20% business. But our cruisers do some serious business. If you want to check it out, it's SanJuanSocialCruise.com. That's SanJuanSocialCruise.com and if you decide to come with us, make sure to, in the dropdown, select Rudy's name and you'll end up in the cool kids area. So make sure to do that.

I appreciate that. We'll definitely take care of anyone who comes in through listening to this episode and we'll do something fun and special together as well. Absolutely. Man, this has been super, super awesome. I appreciate you sharing that with our audience. We'll be sure to include a link to that here somewhere near the episode as well. So that'll be here nearby. One quick recap here of my takeaways. Coming back to events and keeping people engaged, it's community is what I'm understanding. You've built a community over the years. You've maintained community and when you've had community, you've been able to host a cruise in two years, hit a record that took another cruise line 10 plus years to do, and you continue to maintain that community over time. You said we're in the age of community. We're in the age of thought leadership and one of my biggest takeaways here is if you see the opportunity to be at the center of community or create community in this day and age, take it. Because it's needed. So thank you, man. I really appreciate you sharing some of those takeaways.

My pleasure and we'll have to come back again another time so we can talk about outsource sales teams because we didn't even touch on that.

That's true. So for people listening to this podcast, let them know that we run a company that does outsource sales for live events. So we support in the back of the room. I work with several people. I know, Daven, you've worked in the model for many years as well. You're very familiar with it. We can circle back on that as well in your decade plus experience. But I really want to make sure today that people could hear about how you pulled off this epic event known as The San Juan Special Club Cruise because it's special, man. From what I've heard, I haven't been on there yet, it's pretty awesome. I look forward to the opportunity. Any final words of wisdom you'd like to share with our audience here as we just kind of tie a bow on this today?

Yeah, absolutely. So throwing events is both a science and an art. The artistry is kind of what you bring to it, the content, your personality, what you create. But there's a tremendous amount of science to it if you're going to be selling stuff. Everything from getting the butts in seats, making sure they stick, making sure that they're already in a certain way pre-sold before they show up and then once they get there, making sure that you've got a team to help them make the right decision, and then that you are in sync with that team, that you're edifying them, they're edifying you, and you're working kind of as this cohesive unit to make it all happen. So if you don't feel like what you're doing has science, then you're not on the right track. So you gotta bring a guy like Rudy in or whoever you need on your team to make sure that you're incredibly strategic about your event. So that's my two cents.

I appreciate that, man. That's a lot coming from you after decades of experience, knowing that you gotta have a method, you gotta have a science, gotta have an approach. You do not leave it up to chance for luck. Correct. Exactly. Thank you, man. Again, for the audience listening to this, highly recommend reaching out to Daven. Daven, if people wanna learn more about you, obviously there's the cruise. How else can they learn more about you?

Yeah. Davenmichaels.com. D -A -V -E -N -M -I -C -H -A -E -L -S. And I'm Daven Michaels on everything, so.

Yes. You are easy to find on social. You're quite large out there. Awesome, brother. It's been a pleasure having you on the show today.

Pleasure.

It's all mine. Go check out Daven, click on the links, follow him on his socials. If you're interested in the cruise, hit me up, send me a message. Happy to chat with you about it or connect you with Daven. Daven, it's been awesome having you on, man. Thank you.