Every Mistake I Made Getting My Event Sponsored

So last year I made a ton of mistakes getting my in-person event sponsor games sponsored, you know, I had the wrong pitching strategy, I think, wrong pricing strategy, even the activation strategy, I think was not so great. And so I swore to myself that I was going to fix all that for this year's event. And so I want to do a little bit of a recap because the event was a couple weeks ago and there's going to be a lot of lessons here. Yeah, if you have an in-person event for sure, but even if you're just trying to get your social media sponsored YouTube, you know, podcast newsletter, whatever it is, buckle up.

First, a bit of context, what the heck is sponsor games? So I turned my eight-step sponsorship wheel framework into eight games that you play to master the concepts of being a better brand partner. So learning how to pitch better, learning how to negotiate, right? You're actually doing these things, role-playing live with me on stage with, you know, your peers in a small group setting and all that.

And the whole goal of it was, I wanted to create an event that was outcome focus. So it wasn't like, oh, you go there, rub shoulders, network, and it's all great. It's, you know, I'm actually going to learn something. I'm going to leave this event feeling confident or actually, you know, putting this into practice and negotiating more money on this next deal that comes into my inbox.

So that was always really the goal. And, you know, we have accomplished that. Like I can definitively say we've accomplished that based on a lot of the testimonials and the outcomes that we've seen. And so the first thing I wanted to talk about was I did not realize how important physical presence for our sponsors would be.

The first year candidly, frankly, I was terrified of losing a ton of money. And so I was kind of taking any sponsor that I could get. You know, of course, I wanted to make sure that it would still align with, you know, the attendees and it would be helpful for them. But, you know, when faced with the prospect of, you know, losing a bunch of money and, and here was really the thing was that we were mandating that even in the first year that if you were going to sponsor the event that you had to have a physical presence there and there were some sponsors that said, you know what, we would like to support it, but we just physically we can't make it there.

We have commitments at other events or we live in a different country or like whatever it is. And so I was like, okay, well, we'll let that slide. Like we appreciate it. We'll do some email blast for you and all that.

And I regretted that. Actually, I regretted that because it is literally a night and day difference when the sponsor can have a representative physically there, rubbing shoulders with the attendees, breaking bread with them, going out to dinner, right? On all the, all the breaks that we had, you know, coffee breaks and all that lunchtime dinners, right? Because all the foods included for the sponsor to be able to sit next to these creators and learn about them that can also help the sponsors influencer marketing strategy.

There's just so much value in that in-person connection. And it was so clear to me that we had some sponsors, several sponsors that sponsored both years, but also some new sponsors this year. It was so clear to me how much more valuable the event was to the sponsors who had someone there. And so this year we mandated it.

We were like, okay, if you're going to be one of our like main sponsors, you have to have someone there and we were, we were strict about it. And that almost lost us actually a deal because they weren't even really sure whether they were going to be able to attend. It ended up working out. So really, the takeaway for me is that you cannot sacrifice.

Like even if it means that, you know, you may lose a bit more money, what's probably going to happen is you might close the deal, but the chances of that partner who was not physically there coming back and being a repeat sponsor is pretty low. And in fact, you know, the sponsor may not get the return that they're looking for because that was the other actually really interesting thing. It was that even if there wasn't like a direct like ROI conversion like, you know, all these attendees signed up for this tool or whatever, you can tell it's like almost like a qualitative thing that the sponsors who were there rubbing shoulders with everyone, they just left the event feeling good.

They left the event feeling like that was a worthwhile thing. So rather than having a quote-unquote impact on hundreds of people at a larger conference and the impact being someone took their little business card or whatever scanned the QR code on their booth, they walked away from our event with 20, 30 deep relationships. That just always is going to feel more impactful at the end of the day. Second mistake that I made last year was I was not thoughtful enough about how much we integrated sponsors into the event.

Like, here was the big miss, which was like, this is an event about sponsorships. Why am I not giving the sponsors more airtime on stage? Why are we not hearing directly from the sponsors? Like, I'm the sponsorship guy, right?

And I'm telling you what brands think and what they want and all that. So like, why am I not having the sponsors on stage telling you what they actually think? If I'm honest, I think it was a bit of insecurity on my part. A little fear, like, what if the sponsors say something that runs against my teaching or runs against my book or is advice that, you know, this is my imposter syndrome coming out, of course.

But like, I think maybe that was a fear. It was like, I'm the coach guy. I'm the host guy. I'm the guy who's like, created this event.

Everything has to be taught directly from me. And I think one big fix, one lesson that I wanted to take away or one, you know, chain that I wanted to make this year was like, how can I step back a little bit as the host and be more of a facilitator? And so as we were working on on the programming this year, I was like, okay, this is this is the charge. Basically, the charge I gave to my team was like, I want the brands way more involved this year.

And so basically we decided to make games one and two, which was the pitch game and negotiate game twice as long because that's really we realized that was one of the highest leverage games that, you know, takeaways that people were having from the event. Let's focus much more time on those games versus like contract or concept or whatever, which is important. But like really at the end of the day, you're spending most of your time in steps one and two a lot of the time. And so let's integrate the sponsors.

Let's when we're, you know, practicing our pitches, let's call them under the sage, ask them what they thought about the pitches when we're doing the negotiate game. Let's do some role play. Let's let's ask them what do they care about this year and all that. And actually, as like a cherry on top, I want you to listen to this little clip of what Haley from kit said about how how pleased they were, how much airtime they got.

One of the cool things about the event this year is how much we've integrated our sponsors into the event, including kit. I want you to know that before you said that, I've been like, wow, I have never gotten so much stage time. And so it feels like when I think about it from a value perspective, I'm like, wow, they're pitching me. He's telling him out kit a whole day long.

People are deciding on who to pitch and we're playing games about kit. It's kind of amazing. Well, I mean, I think that because of the meta nature of this, of this, you know, event, we thought what better than to include, you know, I love it. You and and kit in those conversations and because this is what happens in real life, right?

I was sitting in the back there, the sponsors little table. And I was like, this event is really good. As someone who runs an event, it's really hard to get someone's time and attention. Somebody who comes to this event is going to dig in and walk away with real skills and relationships.

I can't tell you how much that means to me. And I think we need to toast that compliment in a very special way. Can we shoot some money guns? Okay, we're going to do a countdown.

Ready? Okay, we're going to do five, four, three, two, one. Let's go. Oh my god, I'm obsessed with this shot.

Love it. Let's go. This is the best thing I've ever seen. This actually, you know, dovetails nicely into my third point, which was, this is a brand deal conference.

Why are there not brand deals that people can compete for or win at this event? So this was a big change that we made from years one to two. And how can we convince our sponsors to be part of this, to commit to this, right? Originally, so the reason that I was was nervous about this in year one, because I was like, I have no idea what types of creators are actually going to come, right?

So if I say to, you know, sponsor XYZ, hey, you should give away a brand deal at the event. What if no one who applied or no one who came would actually be like a good fit for that brand, right? Like it's a, you know, like a fashion creator, a beauty creator, like a B2B person or whatever, like, you know, the sponsor, it's just like, I don't, we would never really partner with that person in real life. So that was my fear.

But I was like, you know what? I think I should just get over this because we need to be giving away brand deals at sponsor games. Like that just has to be a thing. And so when I was negotiating with our sponsors from the get go, I was like, this is going to be part of year two, are you in?

And, you know, bless them like they were like, all right, Justin, I don't know how you're going to pull this off, but like, you know, let's roll with it. And in fact, you know, I actually want to share a little kind of testimonial or excerpt from RJ at paper form. What his experience was like giving away this brand deal and having to kind of select from all the applicants, because I think it's, it's pretty insightful. I love the energy here, like being in a room of creative people, of creators who love what they do, their passionate.

And then particularly you guys, like Justin and the team, the energy that you bring, and just the genuine dialogue that's happening is the best. So being part of that as a sponsor is really infectious. The thing that I love the most is just the conversation and the access that you get. You're really breaking down bridges in misconceptions that sponsors might have with their content creators and vice versa.

So being able to just spill those and just have genuine conversations and find common ground is, it's amazing. I'm really excited about working with Mike like to find someone that completely understands our brand and has an audience that we can reach. Being able to try and navigate and negotiate that online with people rather than in person can be really tough. Like, again, this event just breaks down those barriers to be able to figure out, like, where do we align and quickly find that person?

I couldn't do that in 24 hours. I could do that in 24 hours here. I just love that. I'm just so glad that we asked the sponsors to film testimonials for us physically there, because I mean, I just, I love having those, especially to pitch future sponsors for the event, right?

One thing that was really tricky about giving away these brand deals was that our attendees did not have much time to apply. You know, we are really, you know, our agenda, our schedule is like, there is very little oxygen in this, in this agenda, which is actually something we're going to work on for next year. But like, they basically had about 24 hours to, to film and we required them by the way to film video pitches. Like, they could not submit a written pitch.

So everyone had to film a video pitch and they would do the, at midnight, the night before the final sponsor tank event, like the competition and the award ceremony. And so me and Bianca on my team, we had to wake up super early the final day and go through basically like 60 submissions, because we wanted to curate all the submissions for the brands to basically be like, here, you know, here's the big takeaways from these submissions. Like, here's this one, here's this one, here's the type of creator of this person is.

And we basically kind of guided the brands to, you know, give them like a curated list of application. So it was like not so overwhelming for them. But even doing that, it was hard for the sponsors to decide it, you know, at the end of when it came down to it. And so that's some work I think we need to do.

It's like really, really cool to like have this brand deal, that with these brand deals that we give away. But really at the end of the day, it was, I think that part was kind of stressful for the brand. So really need to figure that piece out. Now, the next takeaway is not something that I would change, but it definitely made the event trickier to pitch and nail sponsors down.

So what is the traditional way to try to get a sponsor locked in? It's right. Right. What most people do is they have their pitch deck, their media kit deck.

And they say, here is the, you know, bronze, you know, gold platinum silver, whatever. Here's these different tiers. Here's what you get in each of these tiers. And here's the price.

Right. That's what most people do. Not just for in person event, but for, for, you know, when you're selling online, you know, sponsorships as well. And if you follow me, you know that, that is, I tell you to take that page put in the trash can because you're probably leaving a lot of money on the table.

And so the method that I always have employed is let's put together bespoke custom packages, proposals, depending on what the brands objectives are. And so that is still absolutely the correct approach. But it also makes it a bit trickier to nail down some sponsors who actually might want that traditional method of doing things. I will say, though, and I want to play a little excerpt here from a testimonial that Matt from Lulu gave to us.

So they were our title sponsor that actually actually the flexibility is what convinced him to lock in at the end of the day. So listen, this year we came in as title sponsor because we had such a good experience last year. And so when Justin came back to me and asked about 2026, I immediately was interested in what a title sponsorship would look like. I also knew that Justin would customize it to our needs, which was great as somebody who sponsors a lot of events.

This is probably by far one of our favorite. We immediately started talking about what a title sponsorship would look like. What are some of the things that we would like to have to get out of this? What some of our goals would be?

And Justin came back with a package where it was really hard to say no. It's hard to say no to Justin anyways, but the package he came back with was probably better than anything I could have actually asked for. 100% worth it. I couldn't be more pleased with how this has gone so far and feeling like I really got my money's worth for Lulu and what we were trying to accomplish.

In terms of making changes or being flexible and creating custom bespoke sponsorship deals, to me that's how every event should be like in the future. As a sponsor, as somebody who's paying to be there, the impact is great for us and it's what sticks out. It's what makes me want to say yes when Justin comes to me in a little while and asks me about 2027, which I'm sure that he will. So yeah, creating those custom bespoke sponsorship packages, if you can really drill into what the sponsor needs to help achieve their businesses goals for that year and make them feel like they're a big part of the event.

There's no reason not to do that. I mean, that's a pretty dope clip, right? I mean, you can't get much better than that. But one of the other takeaways from that, I think, is that even now I'm probably undercharging.

One thing I actually didn't mention, those of you who watched or listened to the negotiation that I did with Matt when they locked in as the presenting sponsor, I actually subsequently pitched him more things to kind of add on to that package and they significantly increased their investment for a year or two, which was dope. I didn't get a chance to update everyone. But even that, I feel like might be undercharging because, you know, Haley, I'm sure she'd be okay with me saying this.

You probably heard her from that little clip earlier, even said like given the amount of air time, I think you should be charging more. Like these sponsors are on stage. They're getting to talk about themselves. All the attendees are researching the brands.

Like there is so much integration for, you know, for these brands into the event. One of the big takeaways I think for you is that the more deeply that you are integrating, these sponsors into everything that you're doing, not just, you know, again, not just an in-person event, but if it's, you know, your community or your social media or whatever, you should be comfortable charging more, right? Because oftentimes they are used to the person who just mails it in, right? The 60-second ad read.

They don't even look at the brief until two seconds before the read. They're mailing it in. They mispronounce the name of the brand. Like you can tell, I ran an influencer agency for many years.

You can tell when you partner with 10 creators, the six creators that is just like a, you know, check the box, send me my check type idea versus the ones that really put the effort into it. All right. Next item is all the added value stuff that we, that we gave to our sponsors this year. Number one, which is the thing I think they enjoyed the most, was that I interviewed them live on stage.

And I like during the breaks, basically, and I was like, hey, come on up here. Tell me about what's new, latest and greatest stuff, the stuff that's coming down the pipeline for you. This year, tell me about it, right? And we had a really nice camera setup on stage, like multi-camera and all that.

And I had my editor kind of chop them up and, you know, do the whole multi-cam thing. And we sat into it and we said, hey, you know, feel free to like repurpose this, reuse it however you like, whatever. Even though usage rights was not something that was negotiated into the agreement before, it was this kind of thing where it was an, it was like kind of like an opportunity, like an opportunity in the moment. I was like, I think the sponsors would dig this.

And so I offered it to them and they were super, super appreciative. You know, in addition to that, we were super intentional about including them and everything that we were doing outside of the event, right? Like all the lunches, all the, you know, when we had the dinner crews and we, you know, very strategically, we chose which sponsors were going to be on which boats, depending on the types of creators that we think would resonate with their brand the most. So we did like a lot of intention.

We put a lot of thought behind all that. One little, one little Easter egg. This is kind of crazy. But we named our boats.

And I was the captain of the sponsor ship. Yes. And yes, I had, I had my hand in naming all the boats. But, you know, just those little touches, I think matter a lot.

All right, this next one is exciting because I decided to use the post campaign report as an excuse to pitch some of these brands for ongoing engagements, right? Given that I have all sorts of other opportunities for sponsorship and other aspects of my business all year long, not just having to wait, you know, for another year to sponsor the event, I decided that I was going to pitch one sponsor in particular. I was going to pitch them a very robust, ongoing kind of ambassador ship type partnership.

I was like, I don't want to keep working with your brand all the time. And I, you know, gave five, six different options and it was very robust. And I haven't closed the deal yet, but I'm just not satisfied. I'm not like it is myopic of me to believe that the only way in which I can serve that sponsor is once a year.

No, I can serve them in a lot of different ways throughout the year, ongoing. But that sponsor is probably not going to come to me and pitch that, right? Yeah, I might sponsor the event again in future years, but like they may not have even thought that like, oh, Justin might be interested in like doing podcast integrations or social media stuff or LinkedIn or newsletter, whatever. No, it takes me going to them and proposing something like this.

So, the less than I think the takeaway is always like, don't assume that the sponsor is upset, assume that they're thrilled, but they're busy. And you need to come to them with an idea on a silver platter and be like, here, just like, you want to keep the good vibes rolling and got some extra budget for Q2, Q3, Q4, whatever. Slide that my way. We'll continue.

I'll continue being loud and annoying about how awesome your brand is, right? Like I would love to do that. Speaking of which, here's like a little bonus takeaway. I think Matt would be okay with me sharing this.

But when we asked Matt from Lulu where we should ship all of the, you know, the head because they did have signage and stuff because they sponsored like the, we had the Lulu creator lounge and all that. Hey, where should we ship all your gear? He's like, just hold on, do it. And I was like, oh, so I guess that means they want to sponsor the event again.

So that is definitely good vibes. And in fact, I had a subsequent conversation with Matt and they're very much interested in being a presenting sponsor again next year, which is, which is, I mean, that's all you can hope for, man. Right? Like this is, this is a, this is kind of a dream come true, of course.

My big takeaway here, honestly, is I really need to figure out how to not lose money on this event. I did lose, you know, roughly about $10,000 on the event, technically this year, which, you know, it's a lot of money. But there's so many positive downstream things that happen because, frankly, because I'm the guy that has this event, introductions that come my way, coaching clients that join us later because they heard about sponsor games and then they entered into our universe.

And so it's hard to like, yes, like the, if I look at the budget, you know, for 2026 sponsor games like we are in the red, but it still is a worthwhile thing. Like I, I took to heart when people who, I've talked to people who hosted events and they said it takes five to six years to generate, you know, a, to like to really get momentum on an event. I took that to heart and I was like, I'm in this for the long haul. But I really do think that having sponsors as part of this event completely, you know, rather than it being this like, now we got to hear from the sponsors thing.

This truly is the one event where like people want to hear from the sponsors, which, which is, which I understand and acknowledge is like very unique. But yeah, I, I am super thrilled at how, how the event turned out. I think I did fix a lot about the sponsors experience this year versus last year. But, you know, moving into year three, man, my team and I were talking about this, like, what would it take to offer 20, 50 brand deals that you could apply to at sponsor games?

Like, what would it take to pull that off so that there are brand deals for like, basically, it doesn't matter your niche, it doesn't matter your platform, the type of creator you are, there is like a brand deal that you could apply to. Like, like, what, like, how can we pull that off? Like, I don't know, I don't know what my problem is. I'm always trying to make life more complicated for myself.

But yeah, crazy. Now, if you are seeing all these photos, seeing all this footage and you're feeling extreme FOMO, obviously would love to see you for next year at sponsor games. Early bird tickets are, our for sale right now. You can check the description.

But, like, honestly, if you need help with your brand deals right now, and you're like, yeah, I would like to go to sponsor games, but that feels like really, really far away. We can help you know, we have a coaching program called Wizard's Guild where we will be in your corner to help you with your pitches, with your pricing, with your packages, with your proposals. This is our bread and butter. This is what we do all day long.

So, yeah, we'd love to, you know, have you hop on a call with our team and see if it's good fit. Check the link below. Now, one of the biggest things that we did at sponsor games was negotiation role play where I called people up on to the stage and I was like, hey, you know, I gave them a random objection pretending I was the brand. What would you say in response to this and then they would have to respond.

So, if you want to see more of that, make sure to watch this one right here.