Chris Prinos, Founder & CEO of Indigo Trigger, built a branded conference that grew from 30 to 150 attendees and from 2 to over 30 sponsors in just four years. In this session, he’ll share how the event evolved from a loss-leading experiment into a profitable, brand-defining asset. Members will learn how to launch a niche event, attract the right audience and sponsors, and turn it into a powerful growth channel. This is for founders looking to use events to generate leads, deepen partnerships, and elevate their market position.
TRANSCRIPT
Greg Alexander: Hey, everybody. This is Greg Alexander. You’re listening to the Pro Serv Podcast. Brought to you by Collective 54. If you’re new to this show, this show is for founders of boutique professional services firms. So if you’re in the expertise business, this is for you. We hope to help you make more money, make scaling easier and make an exit achievable. And on today’s episode, we’re going to talk about how services firms can create an event business, particularly in branded event business.
Greg Alexander: To help grow their firms. And this is something that I don’t think enough of our community does. And we have a member with us. Chris Prinos, of Indigo Trigger, and Chris has done this. In fact, it’s quite a remarkable story. In just 4 years, he’s created an event that averages 150 attendees and 30 sponsors. So we’re anxious to hear from Chris on how the heck he pulled this off. But, Chris, for those that don’t know you, would you please introduce yourself and your firm.
Chris Prinos: Sure. So Chris Prinos, Founder and CEO of Indigo Trigger. I founded Indigo Trigger in 2018 basically to help media companies with big technology problems. I’ve spent my whole career in media tech and even more specifically, in RevOps and sales enablement solutions. So a lot of what we do is helping publishers and media companies with technology in the pre-sales space. So your CRM systems, your order management systems, finance operations. We help people with strategic planning and also with heavy lifting related to implementations and getting big projects live.
Greg Alexander: All right. Well, very good. Well again. Thank you for being here, and for making a contribution to our collective. I’ve got some questions prepared. I’m sure we’ll get off track. But I would love to start with the kind of the origin story. So what was the spark or the initial idea that you came up with, and what led you to start your events business, and in describing the origin story, maybe describe the event business itself.
Chris Prinos: Sure. So I really weren’t, you know, doing what we do? We’re not an event company. I was with my girlfriend in 2021 down at the Disney Dolphin Hotel in Orlando, and we were on vacation, and it was kind of the tail end of COVID and I just kind of had an idea that we should have a company party. I mean, it was a great place, you know, a beautiful resort, and within a few hours I’m like, well, maybe we should invite a couple of our customers, you know as well, and get our—because we get very close with our customers doing what we do. So it was, let’s invite some, let’s get our company together for a party. Let’s invite some customers, and then I was like, well, maybe we could get some of our partners to be involved, and, you know, have them sort of fund something. And that was really kind of how the idea came to be. The next morning I built the website, sent the link to a couple of my best customers. I said, “Hey, if we do this, would you be down to join?” I got 3 yeses back, like right away, and that was basically how we started.
Greg Alexander: I love it. On vacation with a girlfriend at Disney, and here we are with a kick-ass event. So you are a classic entrepreneur. I imagine you have an idea a minute, but good for you in getting it implemented. All right. So if you think back to that time, and maybe fast forward just a little bit where it’s like a real thing, and you got to get your first people to buy a ticket and your first sponsor to pony up some dollars, how’d you get it off the ground?
Chris Prinos: So I kind of followed a hosted buyer model where, you know, I knew I was gonna put some money in just to get people to this new event. You know, we didn’t have a marketing budget. We didn’t really know exactly what we were doing, but I had a really strong network, both from people I’ve worked with over the years as well as active customers. So we didn’t sell a ton of tickets in year one. But we basically gave away a lot of tickets to people. And we even had this sort of hosted VIP concept where we targeted some folks that were in really senior positions at big groups. And we offered them, you know, basically 3 nights hotel at the Dolphin and free tickets. We basically funded them to get there. That helped me get some of the sponsors interested and it kind of went from there.
Greg Alexander: So to go into your pocket to the extent that you did—I mean, you were funding people’s travel expense to come to the conference—that took a lot of guts. So where’d you get the conviction that this was going to work?
Chris Prinos: Well, I knew that if I had 2 sponsors that were premium sponsors and putting in what they were gonna put in, we could make it work on the budget we had to find. So, I mean, it was a little bit of a leap of faith. But we were able to do it at the time. And really, for me, it was about what’s the opportunity of getting 30–40 people together—some I know, some I don’t know—to help get our name out there and potentially drive new business.
Greg Alexander: Yeah, now it’s a chicken and the egg thing, right? You gotta get the prospects and customers in the room in order for the sponsors to pony up the dollars, because they’re ponying up the dollars to get access to those people. But also you need the sponsors to come up with the dollars to make it digestible. So who’d you sell first: the attendees or the sponsors?
Chris Prinos: So I would say I got, like I mentioned, some initial interest from some of our best customers, and that was a big help. Then I went to the sponsors, and I kind of played them back and forth a bit. I had to share some of our lead lists with the sponsors. And one of the things that I did for the sponsors was I allowed them to bring 3 or 4 of their customers as well. So they helped drive interest also, and that was a key part of what we did then and still do. Our sponsorships today still include this hosted guest concept. So I used my sponsors as a way to get people I don’t know into the event, and that’s worked really well.
Greg Alexander: And when the sponsors bring a guest, are you covering the tab for the guest, or is the guest paying their own way?
Chris Prinos: We still—for the hosted guests—we cover their 3 nights hotel and the conference pass.
Greg Alexander: Wow! That’s a big commitment. All right. So how did you go from 30–40 people based on an idea you dreamed up with your girlfriend on vacation to 150 people and 28 sponsors? Tell me that story.
Chris Prinos: I go to conferences all the time, right? And when I set this event up, I wanted to take the best parts of what a conference is, which, in my opinion, is the networking. People go for sessions and all that, but they’re really there to meet people that are their peers and learn. So I really wanted to focus on the networking. The first step was coming up with a unique format. I hate when I go to a conference, and it’s a 7 AM continental breakfast and you’re there through happy hour till 6. So I did a 10 to 3 format. We gave people their morning back, and then we end early with a very early happy hour. So the format was unique in and of itself. We were doing it at a Disney property. So we actually got a space at Epcot Center in the evening to have dinner and drinks. So we brought everybody who attended into Epcot Center, and we kind of leveraged the scale of Disney itself just to really make it an emotional experience and really seem like this is something that’s really different.
Chris Prinos: What else did we do? I tried to make sessions that were shorter in length—not these 45-minute stage presentations—but more bite-sized workshop-type things where people could get key takeaways during the event. I wasn’t sure if I was going to do it the second year because there was a lot of work and planning that went into it. But I did do it the second year, and we went from 38 to I think 82 people, with strictly word of mouth. There was no advertising for this or anything. We’re on a very limited budget. People tell me all the time it’s one of the best events they go to in the industry. Everyone’s very relaxed. They’re very open to engage with everybody. It’s a great group of people, and it’s a fun event. The evening events, the park events—all that gives people a way to connect both during the day and through the evening, which oftentimes at events you don’t get. Once 5 o’clock rolls around, people splinter off and go to dinner, but everybody does the evening stuff—whether we’re doing something at Epcot or Hollywood Studios or one of the other venues on the boardwalk.
Greg Alexander: Yeah, and the purpose of the event for you—is it an individual P&L line item where you’re trying to earn a profit? Or is it a relationship-building, business development exercise?
Chris Prinos: Yeah, I mean, it was never really. I mean, obviously being able to cover your expenses was the big goal. We did that in our 3rd year where we actually did make a little bit, you know, a nominal profit. Last year it grew to the point where the profit was a little bit more impressive. But still, I mean, this is being done at a Disney property. The cost structure is very, you know, it’s very expensive. And I do it really just to bring everyone together, you know. And also, being in the lead to cash tech space, we branded it the Lead to Cash Bash. So we wanted our name associated with this niche that we’re in. So we really kind of built the event, grabbed onto that niche. And then, when you think about Lead to Cash, you think about Indigo Trigger. And that was really just getting more exposure for us, getting to meet new people, as opposed to, “Oh, this is gonna be a big moneymaker for us.”
Greg Alexander: So for someone who hasn’t done this before, that is a small service firm like yourself, and they’re aspiring to be a more substantial service firm, and they want to use an event—a branded event, I should say—to get their firm to the next level. When you look back on it now with several years of experience, what have you learned along the way, and what advice would you give everybody that might be doing this for the first time?
Chris Prinos: I think I would just say don’t underestimate the interest from your clientele and your partner network to be a part of something like this. That was something that I think really surprised me. I think putting together a unique format is really important. These people want to get together and talk about prescient issues in their space. So give them the chance to do that—whether it’s workshops, roundtables, case studies on stage. I think putting together that content program is really important. We have intentionally not gone out and done a big ad campaign or brought in external resources to grow this to 300 or 400 people. Could we do that? Probably. But I think the size that we’ve got in that 150 to 175 range—it gives the event a real feel. It’s a community. People that come will tell you, “We go every year. We look forward to seeing the people we met in year one, year two,” and I just really don’t want to lose that feel because I think when you do that, it becomes less personal. People aren’t as open to meeting other people, talking about their challenges, and whatnot. And then make it fun. You have to give people an opportunity to get together off hours to connect. I believe strongly that’s where a lot of the value comes in these kinds of events. So whether it’s—we’re thinking about doing a bowling alley thing after a Friday night this year at Disney Springs—give them a chance to get together and keep that group together through the whole event.
Greg Alexander: Run into people that say, “Hey, we’re living in the digital world. I don’t need to get on a plane and come to an event. I can just attend a virtual event.” Do you ever run into that? And if so, how do you overcome that?
Chris Prinos: You know, I’ve never really run into that. People might go to the site, see it, and say, “Oh, I don’t have travel budget for this this year.” I mean, that’s kind of an issue in our space right now. There are challenges in the media and advertising space. So budgets aren’t like what they were five or ten years ago. So while people might want to come, they just can’t. So we are talking about this year doing a remote, sort of live stream thing that would allow people who register and provide some information to join. But as far as people telling me, “I’m not going to do this,” I haven’t heard any of that feedback.
Greg Alexander: Sometimes I hear from people that the expense of it—and it sounds like you are hearing that budgets are a little tight right now—but also the time commitment. Is your event one day, two days? How long is it?
Chris Prinos: So year one, it was one day. It was just a Friday with a bunch of evening events. And then we started a two-day program in year two. So it’s a Wednesday night arrival—we have a welcome event—and then Thursday, Friday. Because we’re at a Disney property, what I found is so many people bring their families—their partners, their kids. They stay through the weekend. They come early. So we kind of, again, get the benefit of where we do it. And a lot of people do that.
Greg Alexander: Yeah, and keeping it small—I agree with you. Our event, which is called The Reunion, we cap it at 150 for the reasons that you mentioned. I will tell you that sometimes that pisses a few people off because we don’t let them in. If you only have X number of spots, you gotta be really careful who actually is allowed in. So do you screen? How do you handle that?
Chris Prinos: I have caught a couple of people who have showed up at the lobby bar at the Dolphin, and I know they’re unregistered. But you can only screen so much. We don’t get a lot of that. I think we just put them on blast if that happens—be like, “So-and-so didn’t pay,” flash it up on the screen.
Greg Alexander: Yeah. And then in terms of ROI, do you guys take the time to—six months after the event—go back and say, “How much revenue can we attribute to this thing?” Or is it more of a relationship-building activity and you don’t get wrapped around the axle on that?
Chris Prinos: So I would say it’s not extremely scientific, but I can point to 8 to 10 different customers and projects that we’ve got out of the event over the course of the four years that really can be attributed to the event and the connections that I made there. This event, by the way, has helped me connect with senior folks at big media companies that I would never have been able to connect with. And when you are the host of the event and you’re kind of the center of attention, it’s amazing what kind of doors open for you.
Greg Alexander: Yeah. Now, some events are sponsor free. In fact, they sell the fact that there’s no sponsors there as some distinguishing characteristic. We have sponsors at our event. In fact, we couldn’t put it on and keep the ticket prices reasonable unless we had sponsors. I mean, what’s your take on that? Sponsors — is it a good thing, a bad thing from the attendees’ perspective?
Chris Prinos: So we’re very, very aware of — people don’t want to be blatantly pitched to. And when we do have sponsor involvement — and part of our premium sponsorships is stage time — the spirit of that, and it’s written into the agreement, is if you have stage time and you’re a sponsor, it’s to be a customer case study that’s led by your customer. You’re not getting up and doing a demo of your software or talking about how great you are. I screen the material and all that. But I’m totally open to them saying, “Hey, bring your best customer or a panel of customers and facilitate a discussion.” Have them talk about their challenges, their goals, how they solved them. And by the way, we worked with our partner here to do that. So that’s really how I’ve addressed that. I have been to events where it is a blatant vendor pitch, and I think people turn off when you do that. And the sponsors I have get that. Most of them are very seasoned. They know how they’re going to really get their message across and speak to people. So that’s one of the things that we’ve done.
Greg Alexander: When is it?
Chris Prinos: November 13th and 14th.
Greg Alexander: And did you pick those dates based on availability, or how did you choose those dates?
Chris Prinos: Yeah, pretty much. I mean, when you’re doing something at a Disney property, no one wants to go to Orlando in July or August. So that’s something that we had to be aware of. Those weeks in November are generally a little bit more cost-effective. And I was always nervous about being too close to the holiday. In the past years, we were literally the week before Thanksgiving. I was nervous about whether people would travel, and it’s never been an issue. We’ve grown year over year about 25 to 30%. So the time of the year — I think there’s a lot of noise with events also in the spring, and much less so in the fall. So I think that’s worked well for us.
Greg Alexander: Yeah. And it seems like summertime is dead. I mean, kids are out of school, people are going on vacation. It’s also not a great time.
Greg Alexander: All right, Chris. Well, listen, hey — on behalf of the community, I appreciate you coming on and sharing your story here. I learned a lot myself, and I’m sure members did as well. So thanks for the contribution, and for being part of Collective 54.
Chris Prinos: Sure. Thank you much for the time.
Greg Alexander: All right. Couple calls to action for listeners. So if you’re a member and you’re interested in building a branded event business for yourself, we’re going to have a private Q&A session with Chris. So look for that meeting invitation. You’ll get a chance to ask your questions directly of him. If you’re not a member, and after listening to this you think you might want to be, go to collective54.com and fill out an application and we’ll get in contact with you. But until next time, thank you for listening, and I wish you the best of luck as you try to grow, scale, and someday exit your firm.
Note: This transcript was generated by Zoom.