Jon runs one of New York City's most recognizable food and travel channels (643K+ subscribers), built around the city's best restaurants, hidden gems, and the kind of street-level knowledge only a local would know. So by any reasonable measure, he was the kind of creator brands should've been lining up to work with.

Yet, before joining Justin Moore's Wizard's Mastermind, he'd landed exactly one cold-pitched deal in his entire career. A mere timing fluke he's quick to dismiss.

"It was perfect timing, they needed creators in New York, I happened to reach out. I'm not taking much credit for that one."

Jon had everything a brand could want in a creator partner. What he lacked, though, was the conviction that he could go find partners himself.

The "Brands Will Just Come to You" Assumption

When Jon joined Wizard's Mastermind, his long-standing "brands will come to you" belief got challenged pretty quickly. Seeing other creators with similar followings, actively going out and closing deals was the thing no course had ever really given him:

Proof that outbound deal flow was possible (without needing a bigger audience).

Justin started working with Jon directly on proposals, walked him through outreach frameworks, and gave him a front-row seat to see how other creators were actively pitching and winning deals (something much harder to get from a course or YouTube video).

"I did not even know when I joined that Justin would be willing to help me with proposals," Jon said. "I was pleasantly surprised, and I have utilized him many, many times… just bouncing ideas off of him."

The timing for his first real round of cold outreach turned out to be well-suited to the moment.

Jon and his wife had just moved into a townhouse in Brooklyn, and their to-do list for the new place was long. Installations, furniture assembly, odd jobs that pile up when you move.

"What about TaskRabbit?" Jon thought.

It made perfect sense.

He'd already used the service himself, and pitching them around a "settling into a new New York home" content series was the most logical entry point into a TaskRabbit deal.

So Jon introduced himself to the brand, explained the lifestyle series he was building around the move, and offered a few specific ideas for how a partnership could work.

A few days went by.

No reply.

Did Jon screw up the pitch?

He sent a follow-up.

And on the strength of that one extra email, he finally heard back from TaskRabbit after a week (following a non-negotiable habit Justin drills into every Wizard's Mastermind member).

"These are GREAT ideas," the brand said. "Can you please send over your rates for consideration?"

The deal wasn't closed yet. But getting that response from a brand as established as TaskRabbit, on a cold pitch (in his very FIRST real batch of outreach), Jon understood for the first time what Justin had been saying all along.

From a Decent First Deal to Something Much Bigger

It was at the Wizard’s Mastermind in-person retreat in Minneapolis that the TaskRabbit partnership turned from a decent concept into something that would later become partnership-defining.

During a guest speaker presentation, participants walked the room through their recent deals. When Jon's came up, the speaker watched it and offered one note, simple enough that Jon almost laughed when he heard it:

"Next time, have the tasker doing something for you… so YOU can go get food."

As Jon recalled, the first video he created for TaskRabbit had treated the sponsorship the way most creators do. It showed a service, explained what it does, and put a creator in front of it. Highly functional… and totally forgettable.

But what if, instead of demonstrating the product, Jon let the product enable a story he was already going to tell anyway?

For Jon, the story is always about the food. TaskRabbit's job, in that frame, was simply to remove whatever friction stands between him and it.

He immediately brought the concept back to the brand, and to Jon's surprise, they came back with a concept of their own:

TaskRabbit runs a line-sitting program in New York City. For restaurants that are first-come, first-served and popular enough that lines form an hour or two before the doors open, TaskRabbit will send a tasker to hold your spot while you go about your morning. The brand suggested building the next video around exactly that. They picked a beloved pizza spot with a line that forms before dawn. A professional line-sitter arrived with a folding chair and claimed the first spot. Jon dropped his son at school, showed up at the restaurant just as it was opening, and the two of them ate together on camera.

The strange part, for Jon, is that this video didn't feel like a sponsorship, rather a New York City story that happened to have a sponsor attached to it.

And man, did it work.

The second video alone generated over half a million views between Instagram and Facebook, with hundreds of thousands more on TikTok. Jon posted about the results on LinkedIn (a practice Justin specifically encourages inside Wizard's Mastermind), and even the CEO of TaskRabbit liked the post. 

The marketing team began reposting the content, and before the engagement had even concluded, the brand reached out with contracts for two more deals the following quarter.

Four deals with the same company in four months, growing out of a single cold email Jon almost didn't send.

"I've never had a long-term partnership like this before," he said. "Huge victory."

Why TaskRabbit Kept Coming Back

The performance numbers are the obvious explanation, but Jon traces the outcome to a handful of more specific decisions.

1. The pitch was personal. 

Jon wasn't pitching TaskRabbit as an abstract brand opportunity. Rather, he was genuinely moving into a new home and genuinely needed the service. That specificity (the sense that this creator has actually thought about the brand) comes through in a pitch email more than most creators realize.

"I think they definitely respond well to that when they see, okay, he's been following us," Jon said. "Knowing what the brands are doing and how you can fit into their strategy, not how they can fit into yours."

2. He followed up. 

The first email got no response, and the deal came from the second. 

It's one of Justin's most consistently repeated pieces of advice and one of the most consistently skipped steps in practice. Most creators send one email, hear nothing, and move on. 

But Jon did the opposite, and it paid off enormously (if he hadn't followed up, TaskRabbit would've never responded, and the partnership would've never existed).

3. He pitched like a collaborator.

From the initial pitch to every conversation after it, Jon showed up with creative concepts (not just a rate card and a follower count). When TaskRabbit came back with the line-sitting idea, it was because both parties had been thinking like collaborators from the start. 

That dynamic doesn't happen when a creator leads with inventory.

4. He publicized the wins. 

The LinkedIn post after the line-sitter video was a signal to the broader market. 

The CEO liked it, the marketing team reposted it, and two more deals followed shortly after. It wasn't a coincidence, and it's a habit Jon now applies consistently across partnerships.

5. He made the execution easy. 

Jon always prioritized fast turnarounds, clean drafts, and reliable delivery. "I get the videos done very quickly. Once we shoot, you can get them a draft in a couple days," Jon said.

Strong content gets a brand to sign once. 

But it's friction-free execution that gets them to sign again, and again after that.

6. He took the win when Justin told him to. 

Accepting a slightly-below-ask rate on deal one led to three more deals in the months that followed. Holding the line on price would have been the worse financial decision by a considerable margin.

From Creator to Consultant

The deals Jon landed with TaskRabbit are massive proof that cold pitching works when you do it the right way.

But they're not really what Jon talks about most when he looks back.

"I don't just see myself as a creator anymore," he said. "I see myself as a consultant. I see myself as a marketing person. I'm just open to a lot more possibilities right now after working with Justin."

The old operating assumption (make content, get views, wait for brands to arrive) still runs most creators' businesses by default. But Jon has since moved on from this "wait-and-see" mentality, and his business has profited massively from it.

Wizard's Mastermind gave him the frameworks to pitch properly, the coaching to structure deals he'd never have put together on his own, and (maybe most importantly) the firsthand evidence that someone like him could go out and get the deals himself.

"That was one of the best investments I made in myself," he said.

For any creator still operating on the assumption that pitching is something you earn the right to do once your numbers are big enough, Jon's experience suggests otherwise.

"It's never too early. I wish I had started earlier. Your numbers don't necessarily matter if you can help the brand out in a way that fits what they're already doing. You don't have to have 100,000 followers to land a deal."

The brands were always out there. 

He just had to stop waiting for them to find him.

The only thing standing between you and your first high-paying brand deal is a system and the confidence to use it. See how Justin and the Creator Wizard team can give you both →