"I have a solution."

"You have a solution?"

"I have a solution."

That's Bianca, my coaching program director, cutting through a conversation that had been going in circles for twenty minutes. We weren't planning on recording this call. It was just supposed to be me, Sarah (our event producer), and Bianca hashing out sponsorship strategy for Sponsor Games 2027. But about ten minutes in, I figured — screw it, let's turn on the recording and let people in behind the scenes.

Here's the thing about running a live event where creators walk away with actual brand deals: it sounds amazing from the outside. From the inside, it's a logistical nightmare wrapped in something genuinely magical. And we spent this entire call trying to figure out how to keep the magic while losing the nightmare.

The Chicken-or-Egg Problem

Sarah kicked things off with a question that's been eating at all of us: do we go niche with our sponsors, or stay broad?

This year, half our room was DIYers and landscapers. So why not go find brands in that exact space and say, "Hey, 20% of our attendees fit your world — you need to be here"?

I liked the idea. I also immediately saw the hole in it.

We're not running an event with 5,000 people. We're talking 50 to 100 attendees next year. Volume isn't a deliverable we can promise a niche advertiser. And here's the real problem — we don't actually know who's going to show up. We're pitching sponsors six or seven months before the event, long before most tickets are even sold.

"Is this kind of chicken and egg?" I asked. "Do we need to shelve the sponsor strategy before we drive ticket sales, or am I thinking about this wrong?"

Bianca's answer reframed the whole thing for me: we don't need to go more niche. We need to avoid overlap. If we stack the room with five different software companies, we lose room for the B2B and lifestyle brands that could actually round things out. The goal isn't a booth for every niche — it's covering enough ground that most attendees find something relevant.

Why "Easier" Sponsors Aren't Always the Right Sponsors

Here's a pattern I noticed while we were talking through last year's sponsors — Kit, Sure, Paperform, Lulu. All of them work with a huge swath of creators regardless of niche.

Sarah made a point that stuck with me: a brand that's already running hundreds of influencer partnerships a month doesn't need us. They've got the system down. But a brand that's still figuring out their creator strategy, maybe with one person handling it part-time? That's a compelling pitch. "You're still figuring this out — let us hand you the exact creators to work with."

But there's a flip side. Bianca pushed back, and she was right to. A brand that's already comfortable with creator partnerships is actually the easier sell for us. "You're doing this online already — maybe your next step is doing it in person, and who better to guide you through that than us?" A brand with zero reps under their belt is a harder lift, both for the pitch and for making sure the actual on-site experience goes well.

What would you do here? Chase the brands with no experience because they need us more, or the ones who already get it because they're an easier yes?

We landed somewhere in the middle. Look for brands who've done some reps but haven't cracked in-person yet.

The Brand Deal Giveaway Was Never Supposed to Be the Whole Point. Now It Might Be.

Last year, we added the brand deal giveaway almost as an afterthought. This year, it might be the entire reason people show up.

We gave away four brand deals totaling $12,500. Sounds clean on paper. In reality? Attendees had roughly 36 hours to apply between all the other programming, competitions, and sessions crammed into the schedule. Bianca and I woke up at some ungodly hour the last morning to review 60 applications because we wanted to curate it properly for the sponsors.

"This is a bloody nightmare," I remember thinking in the moment.

But here's what happened months later. I'm scrolling my feed and seeing creators from our event actually closing deals with these same brands. Not hypothetically. Actually happening. Bianca put it best: "They made it happen. And we helped make it happen."

That's the moment I realized — this isn't a nice bonus feature anymore. This might be our northstar.

Building the Event Around One Outcome

If we want to be delulu — if we want every single attendee walking away with a brand deal by year three — why not build all of our programming around that being the outcome?

Not just teaching the basics, because people can read Sponor Magnet ahead of time. Not just handing out concepts they can get from the 10K Brand Deal Challenge. Actually handing them a deal.

Bianca's solution was simple and, honestly, a little embarrassing that we hadn't thought of it sooner: bake it into the programming. Stop treating the brand deal giveaway as an extra thing bolted onto the schedule. Make it part of the event itself. Attendees get dedicated time instead of 36 rushed hours. And we get a chance to do things like let everyone watch each other's pitches — something we tried last-minute in year one and it turned out to be one of the best decisions we made.

Sarah took it a step further — what if attendees got a voting mechanism? A wildcard audience score factored into the brand's final decision. Watching people pitch, live, in front of each other? That's not just a giveaway anymore. That's programming.

The Uncomfortable Truth About Inserting Ourselves Too Much

Here's where I got vulnerable on the call, because I think it matters.

I ran an ad agency for seven years. I shut it down. Part of why: constantly trying to convince a brand to sponsor creators is a hard, exhausting game. And I started noticing the same pattern creeping into Sponsor Games — sponsors saying things like, "Can you just curate this for us? We don't know what we're doing."

One year, we made a mistake I'll admit publicly. We collected the sponsorship money upfront and held a portion of it in an account, waiting to release it to the winning creator once the brand gave the green light. That was dumb. We shouldn't have been the ones holding that money. The brand should pay the creator directly — they're the ones doing the partnership.

Bianca's read on this was sharp: the more we position ourselves as the ones running every part of the process — the voting, the curation, the payout — the more responsibility falls on us to manage all of it. What we actually want is to be the conduit. Give the sponsor a great pool of creators and get out of the way so they can make their own decision.

There's a version of this business where you make yourself indispensable by doing everything for everyone. There's a better version where you build the room, invite the right people in, and let the relationships happen.

What a Real Sponsorship ROI Conversation Sounds Like

Not every sponsor needs the same deal, and pretending otherwise is where a lot of events get sponsorship wrong.

Sarah raised something I hadn't fully considered — most of our attendees aren't ready to write their first book. So was Lulu's sponsorship actually about book sales, or was it about face time? Understanding what a sponsor's actual goal is changes everything about how you structure the deal. It doesn't have to be an equal playing field for every partner.

We also talked about the mandate we've had — sponsors have to be physically on-site. I still believe in that. But if we're going after more sponsors at a lower price point, will they still think it's worth sending someone in person? That's a real tension we haven't solved yet.

The Hard Rock Deal Nobody Saw Coming

I want to tell you about the deal Sarah pulled off, because it's the best example I have of what's possible when you stop thinking small.

We wanted to do a river cruise down the Riverwalk in San Antonio. Sarah found out you could actually cater meals on the river boats. That led to a deal with the Hard Rock Cafe — they had a brand-new VIP speakeasy room they wanted content on, and they didn't even want us to talk about what they were sponsoring. They just wanted content of the room.

"They did not want content on what they were sponsoring," Sarah said. "They were like, we have this new speakeasy, as long as you make content on it, we're good."

That's the whole game right there. We weren't a huge event. But we had a need Hard Rock could fill, and we found it by asking a question most people wouldn't have bothered asking: what's actually available to us here?

So, What's the Pitch for Next Year?

We're still figuring out how to position the ask to sponsors clearly — separating "you're sponsoring the event" from "you're also committing to sponsor an attendee's brand deal." That confusion cost us clarity last year, and it's on me to fix it going into 2027.

We're also sitting on a decision I haven't announced anywhere yet: we might be moving Sponsor Games out of San Antonio entirely.

I don't have all the answers yet. What I do know is this — every city has magic in it that most people only ever see scrolling Instagram. And if we can find the version of the Hard Rock deal in a new city, we'll have done our job.

We talked through a lot of what's shaping Sponsor Games 2027 in this one, but if you want to hear my own unfiltered reflections on how the sponsorship strategy actually played out for Sponsor Games 2026, check out this episode.

If you've got thoughts on what would get you in the room — the brands you'd want to see, the partners you'd want a shot at landing a deal with — I want to hear it. And if you're building your own sponsorship strategy right now, whether it's for a podcast, a YouTube channel, or your own event, that's exactly what we work through inside Wizard's Guild. If you haven't read Sponsor Magnet yet, start there.

What would you build your event around if you knew the outcome you wanted people to walk away with?