Bill Flitter has been in advertising for 20 years. Buying sponsorships, not selling them. So when he decided to pitch one himself for the very first time, he braced for the fight — the back-and-forth, the objections, the slow crawl toward a maybe.

Two emails. Two weeks. Done.

And then the sponsor said something that caught him so off guard he had to fake his poker face on a Zoom call.

I get told all the time that people don't land brand deals because they "refuse to dance on TikTok." That's the excuse. Bill's story is the reason I don't buy it anymore.

Why "I Don't Know What I'm Doing" Was Actually His Edge

Bill runs Sideline, a startup that handles fan engagement and loyalty for youth sports tournaments — think ticketing data, demographics, and yes, sponsorships. He'd spent two decades on the buying side of advertising deals. Never the selling side.

Here's the thing — that could've been a disadvantage. Instead, it made him coachable.

"I didn't like, oh, I know better than Justin. I'm older than him, I have so much more experience than he does," Bill told me. "I'm like, let's see if it works, right?"

He didn't try to reinvent anything. He grabbed my book, treated it like a literal playbook, and started sending emails off a prospect list before he'd even finished reading it. That's the part I want you to sit with. He didn't wait until he felt ready. He started before he felt ready — and figured he'd catch up on the strategy while the replies came in.

They came in faster than he expected.

The Email That Started It All

It was cold outreach. Bill didn't know the restaurant chain he reached out to from anywhere. He pulled some of the copy structure straight from the book, tailored it to his tournament sponsorship, kept it short, and hit send.

Two emails later, the sponsor called him back.

What would you do in that moment? Most creators panic and start improvising. Bill did the opposite — he asked a lot of questions and, in his words, "played kind of dumb." Not because he didn't know what he was doing, but because he wanted the sponsor to talk first. Find out their goals. Let them tell him what mattered before he pitched anything.

That's a move I talk about constantly inside Wizard's Guild — the pitch isn't the moment you perform. It's the moment you listen.

"Oh, Like No, Go For It"

Bill put together a proposal with three tiered options — short-term, long-term, and something in the middle. Standard test-and-see approach. The sponsor wanted a six-month trial and offered a free kids' meal to every family that bought a tournament ticket.

Bill asked the obvious follow-up: how many meals should he cap it at?

"He goes, 'Oh, like no, go for it.' Like, I'm what do you mean go for it? There's no limit."

Bill said he was stunned. Twenty years in advertising, and no one had ever told him to just let it run.

There it is. That's the moment the deal stopped feeling like a transaction and started feeling like a partnership. And it happened because Bill showed up believing he had something worth saying yes to — not something he needed the sponsor to rescue him from.

The Campaign Nobody Asked For, But Everybody Remembered

This is the part of Bill's story I love most, because it wasn't in any proposal. It was an afterthought he added because he wanted to try something.

He printed physical cards — like a business card — with a QR code on the back that just said "free surprise." Scan it, get a coupon for a free kids' meal. But he didn't stop there. He tucked a real $5 bill inside the card, physically attached to it.

"We wanted to be really visible versus, oh, we'll just take $5 off your ticket. Here, they could see the $5 bill attached to it."

Twenty bucks of value, delivered as a surprise instead of a line item. Parents who'd normally grumble about paying to get into a youth tournament were suddenly pulling cash out of a business card.

He also named the entire tournament after the sponsor — the Pacific Catch Classic — and built a step-and-repeat banner so winning teams could take photos for their own social media. Free content for the sponsor, created by the players themselves.

Screw what's normal. Strive to be abnormal. Bill didn't have a big brand, a track record, or performance data to point to. He had one tournament, one geography, and zero history. So instead of competing on proof, he competed on creativity.

The Mindset Shift That Changes Everything Downstream

Bill said something that stopped me mid-conversation. Looking back at his own pitching, negotiating, and follow-up, he realized he used to operate from scarcity. "I always thought, well, man, if I don't close this deal, then I'm not going to close any deal. I got to close it."

Then it flipped. "I just changed my mindset. It's like, yeah, I have something of value."

That single shift — from I need this deal to close to I have something of value — is exactly what we work on inside Wizard's Guild. Most creators walk into a pitch acting like they're asking for a favor. The moment you actually believe you're offering a real opportunity instead of begging for one, everything changes. Your pricing changes. Your follow-up changes. Even how you sit with silence changes.

If you want help making that shift — and pitching like you've already made it — grab a free sponsorship strategy session with my team over at Wizard's Guild.

Silence Isn't a No. It's Just Silence.

Bill said it took roughly two emails before this sponsor got back to him. But he was clear that his broader philosophy isn't about speed — it's about persistence without scarcity.

"I don't treat that as a no. I just think, you know what, they're probably busy and probably got buried. Let's just reach out again with a different email."

He never manufactures urgency. No fake deadlines, no "let me know or I'll close this out." Because he knows he'll probably follow up again next week, or next month, regardless. That patience — paired with the belief that his offer has real value — is what let him play the long game instead of the desperate one.

Borrowed Credibility, Delivered as a PS

Here's a detail most creators would've left out of the email entirely. Bill's father-in-law owned a restaurant, Lots of Pasta, in Danville — a spot that had thrived for years serving hungry basketball families straight from the gym down the block. Bill had coached basketball himself, at Disal Camp and St. Perpetua.

So he added a PS to his pitch email, tying his own coaching background to his father-in-law's local restaurant success.

It worked. One recipient used to eat there in high school. Others had simply heard of it. It became a conversation starter — a way to build trust with zero deal history to lean on.

But here's what I noticed: Bill didn't invent credibility out of thin air. He looked at what he actually had — family ties, local roots, a coaching background — and found the version of it that mattered to the person on the other end of the email.

What This Means For You

You don't need 20 years of sales experience. You don't need dozens of past deals to point to. You don't even need to feel ready.

You need a plan you trust enough to follow before you fully understand why it works — and the belief that what you're offering is worth saying yes to.

Bill proved that in two emails and two weeks. What's stopping you from testing it in your next pitch?

If Bill's story lit something up for you, my book Sponsor Magnet is the exact playbook he followed — templates, pitch structures, and the whole system, start to finish.

And if you want a coach in your corner while you run it, that's what Wizard's Guild is for — one-on-one help building your pitch, your pricing, and the mindset shift that makes the whole thing click.