I just closed a $10,000 sponsorship deal.

My lead coach Joe just closed one for $7,000.

And instead of just celebrating those wins and moving on, we thought: what if we completely deconstructed these deals for you?

How the conversations started. What we pitched. The negotiation moments. What we included in our deliverables. And honestly, where we probably left money on the table or could have done better.

Because here's what I believe: The best way to learn sponsorships isn't from polished case studies. It's from watching people who are actually in it break down their thinking in real time.

So let's do exactly that.

The Year-Long Sales Cycle That Almost Didn't Happen

My deal took over a year to close.

Not because the brand ghosted me. Not because they weren't interested. But because the feature they wanted to promote kept getting delayed.

They were launching Instagram and Facebook integration for their tool—a huge new release after being YouTube-only for years. But software development is unpredictable. Launch dates kept getting pushed back. Timelines kept shifting.

Most creators would have given up. "They'll reach back out when they're ready."

Wrong move.

The brand will forget about you. They'll move on to other priorities. They won't know you're still interested.

So every three to four weeks, I followed up with a simple question: "How's the feature development going? Is there anything I can do to help? Would you like me to test it out once it's ready?"

Not annoying. Not pushy. Just genuinely helpful.

And they weren't annoyed at all. In fact, they appreciated the consistent check-ins because it kept our partnership top of mind while they navigated internal delays.

The Deliverables That Didn't Look Like Much (But Were Worth $10K)

Here's what I ultimately proposed:

• One dedicated newsletter blast

• One custom short-form video for their website (not posted anywhere else)

• 12 months of usage rights for that video (website only—no social, no paid ads)

• Three podcast integrations

On the surface, you might think: "How did you convince a brand to pay over $10,000 for that?"

This is the magic of understanding brand goals.

If I'd just come to them with an à la carte menu—"Here's how much I charge for a podcast integration, pick what you want"—this deal never would have happened.

Instead, I listened. I understood their primary challenge: they were struggling to articulate the value proposition of this new feature.

So I proposed creating a custom video testimonial for their website. An authentic, unscripted breakdown from someone who actually uses the tool explaining why this integration matters.

They loved this idea. They hadn't even thought of it until I brought it up.

"This is such a great idea because we've been struggling to articulate the value proposition, and what better way than having the guy who actually uses the tool give an authentic testimonial that we can put on our website?"

My contact used that justification to get buy-in from their superiors. "Here's why we should pay Justin $10K—he's going to help us spread the word about why this integration is important."

And here's the beautiful part: This was my top package. They picked it with zero pushback.

The Payment Flexibility That Made Everything Easier

When it came time to actually paper the deal, the brand asked if they could use their existing affiliate platform instead of my standard contract.

"It'll go a lot faster if we use our current affiliate tool. We already have a master service agreement with them. We'll just put custom numbers in there for you. You'll get paid way faster."

A lot of creators would balk at this. "That's not my process. That's not how I do things."

I said: "Sure, it's fine. It's not what I usually do, but I can be flexible."

Why? Because making it as easy as possible for brands to give you money should always be your North Star.

The result? I got paid within seven days. Zero transaction fees because they covered the affiliate platform costs. Win-win.

As Joe put it: "I have always said, make it as easy as possible for people to give you money."

Joe's $7K Deal: When the First Partnership Doesn't Work Out

Joe's story is different but equally instructive.

He'd done a previous deal with this brand where there was a mismatch. They're a big company with multiple product lines, and they wanted to promote something that wasn't right for his audience.

The first sponsorship flopped. No conversions. The metrics looked terrible.

Most creators would stick their head in the sand at this point. "Well, that was embarrassing. I'm never talking to them again."

Joe did the opposite.

He sent a post-campaign report and recommended a different approach. He told them straight up: "The tool you're promoting isn't the right fit for my audience. Here's what would actually work."

They wanted to switch to full affiliate. Joe pushed back: "That thing you want to promote still isn't going to move the needle."

They left it there for a while. Joe followed up earlier this year. The brand had reorganized and was finally ready to promote products that actually aligned with his audience.

He sent them three packages:

• Package 1: Price + higher affiliate commission

• Package 2: Price + different affiliate structure

• Package 3: Full upfront payment with paid usage rights (no affiliate)

The brand came back with an unexpected response: "We don't want the paid usage rights. Can we swap that out for something else and still pay you full upfront?"

Final deal: $7,000 for a three-month podcast integration campaign, three featured newsletter sections, a four-video YouTube educational series, and three YouTube Shorts.

All upfront payment. No affiliate strings attached.

The Confidence That Comes From Knowing Your Value

I asked Joe where he found the confidence to keep engaging with this brand after the first deal went poorly.

His answer cuts to the heart of what separates successful creators from struggling ones:

"I know I can help them and I know they can help my audience. I never view it as just trying to tap the well of money. I know the value I can bring to the table."

Joe isn't chasing every brand. He won't work with companies that price via CPM and demand make-goods if you don't hit their numbers. Those brands need volume, not value.

"They need to go sponsor the Apple Podcast top 10 list. I can't help those people."

But for brands with an education gap? Where complex products need thoughtful explanation? Joe is exceptionally confident: "I am a great teacher, and I say that confidently because I've been told that a lot."

That confidence changes everything.

When Joe knows he can bring genuine value to a company trying to gain traction in a specific area, he never hesitates to reach out. Even after a deal that didn't perform well.

"As long as I know I can help them and it's valuable to my audience, I'll keep reaching out until they say, 'Hey, never email us again.'"

The Niche Myth That's Costing You Money

Both Joe and I operate in what most people would consider "small" niches.

I teach sponsorship strategy. My YouTube videos get fewer than 1,000 views most of the time. My podcast downloads aren't massive.

Joe teaches business systems for solopreneurs. His channel isn't pulling five-figure view counts either.

But here's what brands understand that creators often don't: It's not about follower count anymore.

Look at any short-form platform—TikTok, YouTube Shorts, Instagram Reels. The "follow" button barely matters. The algorithm prioritizes viewer behavior and engagement, not who you subscribe to.

Jack Conte (Patreon's CEO) gave a famous talk at South by Southwest called "The Death of the Follower" about exactly this.

Brands are still using follower count as a proxy for influence, but it's your job as a consultant—not just a creator—to educate them.

When a brand tells Joe his rates are too high for his follower count, he has a perfect response: "If you were just looking for views, you could go to an ad network and buy there. But you came to me because you said you liked my content. You value the trust and teaching ability, not just the reach."

What We're Really Selling (And It's Not Followers)

Here's what Joe said that really stuck with me:

"Your trust as a creator goes beyond just your audience. You're more than your follower count. You have influence, and that influence extends to wherever you are."

When brands hire us, they're not just buying access to our audiences. They're buying:

• Expertise they don't have internally. The landscape changes so quickly—Tik Tok's gone, it's back, it's gone again. Brands need people who are in it every day to guide their strategy.

• Authentic testimonials they can't manufacture. They can't hire an actor to pretend to know their product. But they can partner with someone who genuinely uses it and can explain its value.

• Content that prevents customer churn. If your tutorial video prevents even one of their customers from canceling, what's that worth? Way more than a one-time $7K or $10K payment.

• Educational assets they can reuse indefinitely. Both of our deals involved creating content that brands can point customers toward anytime someone has a question. That's ongoing value from a one-time investment.

We actually have a coaching client who just landed a 12-month deal creating content exclusively for a brand's YouTube channel—not his own. They initially hired him for consulting, loved his work, then realized they couldn't execute the strategy themselves.

That deal is allowing him to quit his 9-to-5. From one partnership.

The Brutal Honesty That Builds Trust

One thing Joe does that most creators are terrified to do: he doesn't just say everything is great and wonderful in his sponsored content.

"I'll say, 'Oh, this feature is a little strange. They could probably change the way this is done.'"

Why would he criticize a product he's being paid to promote?

Because it signals to the brand: "I'm actually using this. I'm not just reading your talking points."

And it signals to his audience: "He's not only saying nice things because he's getting paid."

Result? Higher trust on both sides. The brand gets real user feedback they can send to developers. The audience trusts his recommendations more.

Brutal honesty beats fake enthusiasm every time.

Where We Probably Left Money on the Table

Neither of us executed these deals perfectly. Here's what we could have done better:

My deal: I should have asked about their overall marketing budget for this launch. If they're investing heavily in this feature release across multiple channels, my $10K might have been pocket change. I could have positioned additional deliverables—maybe a webinar, maybe more social amplification—as part of a larger launch strategy.

Joe's deal: He probably could have negotiated harder on the usage rights swap. When they said "we don't want usage rights, can we swap it for something else," that was an opportunity to propose something with higher perceived value. Maybe an exclusive training session for their team. Maybe a quarterly strategy call.

We're not perfect. We're still learning. And that's exactly the point.

The Takeaways You Should Actually Apply

If you're reading this breakdown and wondering what to do with your own sponsorship strategy:

1. Follow up consistently, but make it about them. Not "Are you ready yet?" but "How can I help until you're ready?"

2. Understand their goals before proposing deliverables. What are they actually trying to accomplish? What problem keeps them up at night?

3. Be flexible on process if it makes their life easier. Your rigid contract system isn't worth losing a five-figure deal over.

4. Don't ghost brands after deals that underperform. If you genuinely believe you can help them, keep the conversation going. Propose different approaches.

5. Know your unique value proposition and be able to articulate it confidently. Joe is an amazing teacher. What are you?

6. Create packages, not single offers. Give brands multiple ways to work with you at different investment levels.

7. Make it stupidly easy for people to give you money. Remove friction wherever possible.

Want to learn how to structure these kinds of deals for yourself? Check out Sponsor Magnet for the complete framework, or join us inside Wizard's Guild where Joe and I break down deals like this on our bi-weekly coaching calls.

And if you really want to practice pitching and negotiating in real-time with actual feedback? Come to Sponsor Games in San Antonio, March 15-18, 2026.

Because the difference between a $500 deal and a $10,000 deal usually isn't your audience size.

It's knowing how to position yourself as the solution to a problem the brand is already trying to solve.