Less than a month out from Sponsor Games, I was more than $20,000 in the red.
I'm not telling you that for sympathy. I'm telling you because what happened next is exactly what I teach — and I wanted you to watch me actually do it under real pressure, with a real sponsor, in real time.
The brand was Kit. The contact was Haley, their Head of Creator Community. And over the course of two calls — with a months-long gap in between where I genuinely wasn't sure the deal was going to happen — we got it done.
Here's everything I learned from watching myself negotiate.
Listen for the Northstar Before You Pitch Anything
The first call started with Haley describing her new role at Kit. She said something I flagged immediately: "Human connection and human relationships are really what set us apart."
That wasn't small talk. That was a brand telling me their northstar in plain language — what they believe, not just what they sell. And the moment a sponsor volunteers that, you stop everything and write it down. Because that becomes the foundation of every pitch angle you'll ever send them.
A lot of creators walk into sponsorship calls ready to lead with their metrics. Followers, downloads, open rates. But Haley didn't care about metrics in isolation. She cared about impact. About whether her brand could show up in a room and genuinely serve people. So every element of my pitch had to speak to that — or it wasn't going to land.
The Pitch That Landed (And the Part That Didn't)
When I finally laid out the proposal — $12,500, email promotion, logo placement, speed dating with attendees, a co-branded creator sponsorship — Haley was honest with me in a way most sponsors aren't.
She hated the fluff.
"Email mentions, signage, logo placement — I just don't think that translates to much of anything." Not because she was being difficult. Because she'd bought those deliverables before and they hadn't moved the needle. She wanted to know one thing: how am I going to be of service to the people in that room?
This is the thing I keep telling creators and I'll say it again here: lead with outcomes, not outputs. A logo on a banner is an output. A sponsor walking away having meaningfully taught, connected with, and served 75 creators — that's an outcome. That's what gets sophisticated marketers to say yes.
The speed dating idea? She had a love-hate relationship with it. She could rapidly meet a lot of people and schedule follow-ups, but five minutes isn't enough time to actually serve someone the way she wants to. It creates a ton of follow-up work on her end with no guarantee of real impact.
Her honest feedback was gold — even the parts that stung a little. And it reminded me of something important: when a brand does give you feedback after a no or a "not quite," that intel is worth more than almost any pitch advice I could give you. Ask for it whenever you can.
The Gap in the Middle
After that first call, Haley went quiet.
Not because she wasn't interested. She was traveling between continents, championing the event internally to her team, going to bat for me behind closed doors. I didn't know that at the time. What I knew was that my follow-up emails weren't getting responses, and a deal I thought was close wasn't moving.
I kept following up anyway. Politely. Persistently. Because I believed in what we were building, and I knew if I could get Haley back on a call, we could figure it out.
Months later, she came back. And we picked up almost exactly where we left off.
Here's what I want you to take from that: the silence wasn't a no. It almost never is. Brands have competing priorities, internal budget conversations, team dynamics you can't see from the outside. Your job is to stay top of mind without being annoying — and to never give up on a deal you genuinely believe in.
The Second Call: Where the Deal Actually Got Made
By the time we reconnected, a few things had changed. Kit Studios was about to open a New York location. I had a presenting sponsor locked in (Lulu). The event was bigger and more ambitious. And I came back with a reduced ask — $7,500 — anchored around the things Haley had actually told me mattered.
The conversation moved fast. Haley confirmed she was the decision maker — she didn't need to run this up a chain. That's information worth asking for early. I've wasted weeks sending follow-up proposals to people who had to get approval from someone I never talked to. Knowing your contact has authority changes the entire pace of the negotiation.
When I floated the idea of doing a mini podcast recording on stage that Kit could repurpose — including for paid ads — something clicked. That was content. That was something she could take home and use beyond the event weekend. That's when the energy shifted.
We landed at $8,500 — plus a $2,500 brand deal for a Sponsor Games attendee to go film at the new New York studio for the grand opening, plus a free ticket to Craft and Commerce for the grand prize winner that Haley threw in at the end just because she felt like it.
Not $12,500. Not $7,500. $8,500 and a creative prize package that neither of us had fully envisioned at the start of the conversation.
What Sophisticated Brands Are Actually Doing in Their Heads
At one point, Haley walked me through the math she does before committing to any event. 100 attendees. 30% engage with the sponsor. 30% of those convert. That's 10 new customers. Depending on creator account size and expected lifetime value, that alone could cover the cost of the sponsorship.
And that wasn't even counting retention — keeping existing Kit customers from churning to a competitor who might also be at the event.
This is how good brand marketers think. They're doing ROI math before they ever sign your proposal. So your job is to do that math for them — or at least directionally — before they have to ask. If you can show a brand what the rough return looks like in your pitch, you remove their biggest objection before they even raise it.
The Thing That Actually Closed It
At the end of the deal, Haley said something I didn't expect.
She said yes wasn't just about awareness, retention, or acquisition. It was also about advocacy. I've been a Kit customer and a vocal proponent for years. I recommend them from stage. I mention them in conversations at events. That compounding value — the word-of-mouth endorsement that happens year-round — is something a brand can't fully quantify on a spreadsheet. But it factors into the decision.
Don't just sell the deliverables in your sponsorship pitch. Sell the relationship. Sell the fact that you're a genuine believer in what they're building, and that your audience is going to hear about it not just during the campaign, but because you actually use and love the product.
Long-term advocates are worth many multiples of a one-off campaign. And the brands with the best marketing teams know it.
If you want help doing what I did in this negotiation — building the pitch, navigating the objections, and staying in the game long enough to close — that's exactly what we do inside Wizard's Guild. And if you want the full framework in book form, grab Sponsor Magnet.
What's the longest you've ever stayed in pursuit of a deal before it finally closed — and was it worth it?
