Josh Hall DM'd me out of nowhere one day.

"Justin, thanks. You just made me 5 figures in sponsorships for my in-person event."

I had no idea what I'd done. But apparently something clicked, because a few weeks later we got on a call together — and what came out of it was one of the more honest conversations I've had about what's actually holding experienced creators back from the sponsorship revenue they deserve.

Josh teaches web designers how to build profitable businesses. He's not a tiny creator. He has a thriving community, a podcast, a YouTube channel, in-person events. Brands were already sliding into his DMs asking to work with him. And yet — he was sitting on gold and didn't know it.

Sound familiar?

The "6-Figure or Nothing" Trap

Josh came into the call with a rule: he wouldn't pursue any revenue stream unless it had a clear path to six figures. I get the logic on the surface. Opportunity cost is real. Time is finite. If you can launch another course, why bother chasing sponsorship crumbs?

Here's the thing, though. That framing is wrong — and it's wrong in a way that costs you.

Sponsorships aren't just a revenue stream. They're a service delivery mechanism.

Think about it this way. Survey your audience and ask them what keeps them up at night. I guarantee some of their answers have nothing to do with your core topic. They're stressed about bookkeeping, legal stuff, tools they don't know how to pick, workflows that are eating their time. Are you going to build a product for every single one of those problems? No. But there's probably a brand out there whose whole business is solving exactly that problem for your exact audience.

When you treat sponsorships as purely a "revenue thing," you're being myopic. You're assuming you're the only one capable of solving your audience's problems. You're not. And the creators who get this — who lead with service first — almost always make more money in the end, not less.

The Handyman Who Closed a 5-Figure Deal

Before we got into the tactics, I told Josh a story I think about a lot.

When I moved to Minnesota, I hired a handyman to help us get ready for winter. At some point I asked him about gutter guards. He didn't hesitate. "There's only one company you need to call. I've used them for 30 years. Local. Amazing customer service."

I didn't Google it. I didn't check Trustpilot. I called that one company. They gave me a 5-figure estimate and I seriously considered it — based entirely on the recommendation of one person.

That handyman had no social media presence. No newsletter. No YouTube channel. But he had influence, and a brand would have paid for access to it.

Your influence doesn't need to be massive to be monetizable. It needs to be trusted. If you have 50 clients who hang on your every word, those 50 people might be worth more to a software company than 50,000 random followers.

The PSA Framework (And Why Affiliates Are Just Untapped Sponsors)

One thing that kept coming up in the conversation was Josh's affiliate revenue. He had tools he'd been recommending for years — some for a decade — and was earning commissions on them. He viewed them as affiliates. Not sponsors.

But here's what I actually think: affiliates are sponsors you haven't asked yet.

I use a framework I call PSA — Products (things you directly sell), Sponsors (brands and companies), and Alliances (partners and referrers). Most creators collapse these categories in their heads, and it costs them. Because once you realize your top affiliate partners are already sold on your audience, going back to them and saying "hey, let's do a proper campaign" is the easiest pitch you'll ever make.

They already trust you. They already know your audience converts. You're not cold-pitching anyone. You're just formalizing a relationship that's already working.

"What would it take," I asked Josh, "for you to go to your top 10 affiliates right now and pitch them on a sponsorship?"

He got quiet for a second.

That quiet is worth a lot of money.

Throw Away the Rate Sheet

This is where I pushed Josh hardest — and where I think most creators at his level are leaving the most on the table.

Josh had been thinking about sponsorships as a productized offer. Here's my packages. Here's what's in them. Pick one.

I told him to trash it.

Not because packages are evil. But because handing a brand a pre-built menu before you understand their goals is like a doctor walking into the exam room, writing a prescription without hearing your symptoms, and walking back out.

You're not solving their problem. You're just selling them a thing.

When you have a real conversation first — when you ask about their goals, their challenges, what's failed in past partnerships, what would make this campaign a win internally — you can come back with a proposal that says on page one: here's what I heard from you. And then on page two: here's exactly how we're going to solve that.

I've seen this play out hundreds of times. The creator who does this makes 10x more than the one with the rigid rate sheet. I'm not exaggerating. Easily 10x.

You also stop doing work the brand doesn't even care about. How many creators bundle in an Instagram post and a YouTube video and a podcast mention because "that's the package" — when the brand only cares about the newsletter? You did extra work for free, and they didn't even value it.

Ask About the Budget Range, Not the Budget

Speaking of money — there's a question I teach that changes everything in negotiations.

Don't ask: "What's your budget?"

Ask: "Do you have a sense of what budget range you're working with?"

Here's why the distinction matters. When you ask for a budget, brands clam up. They don't want to give you a number because they know your proposal will magically land at exactly that number. They're not wrong to be suspicious.

But when you ask for a range, you're giving them breathing room. They can say "$5K to $15K" or "$50K to $100K" without feeling like they've negotiated against themselves. And 75% of the time — across hundreds of negotiations I've done personally — they'll tell you. They'll actually tell you.

The other 25% will stonewall. "We've never done this before. You're the expert. You tell us." That's where your "hell yeah number" comes in. That's your floor — the number that, if they say yes, you're genuinely excited regardless of everything else. Start your lowest package there, and make sure you'd be happy if that's all they took.

Invent Deliverables They Don't Even Know They Want

One of my favorite moments from this session was when Josh pushed me on what kinds of things you can even offer a sponsor.

My answer: whatever solves their problem, including things that don't exist yet.

I told him about a sponsor call I was on where the brand kept saying the same thing over and over: "When our newsletter sponsorships end, it just disappears. It feels like it goes into the ether."

I wrote it down. Wrote it down again when they said it again.

When I came back with the proposal, I'd mocked up a new section of my website called "Partners" — their logo, their campaign messaging, all of it. Password protected. Included the link in the proposal.

"Remember how you mentioned things disappearing? Here's a permanent home for this partnership."

They said, "Where do we sign?"

That page didn't exist before the call. I invented it to close the deal. It was low lift for me, high value for them.

The same principle applies to workshops, webinars, co-branded resources, targeted email blasts to specific audience segments. Don't limit yourself to what's on your current "menu." Ask what they need, then build it.

The Due Diligence Most Creators Skip

Josh asked something I hear from a lot of people stepping up their sponsorship game: how do you know you can trust a brand enough to put them in front of your audience?

Reputational vetting is the obvious first step — make sure they haven't been in a PR crisis you'd be embarrassed to be associated with. But that's the easy part.

The harder, more important part is going through the customer journey yourself.

What does the signup flow actually look like? Can you redeem the promo code? Does the landing page make sense? Is there a hidden gotcha — like a promotion that requires an annual contract to unlock?

Because here's what happens if you skip this: something goes wrong, your audience gets frustrated, and they're not going to blame the brand. They're going to blame you. You're the one who vouched for it.

I once told a sponsor their landing page was terrible before I'd agree to go live. I wasn't contractually obligated to say anything. But I filmed a five-minute walkthrough video showing exactly how the product worked and why I loved it — asked them to put it above the fold. Then I rewrote their CTA copy so it was actually clear.

They were blown away that I cared that much.

Their conversions went up. They rebooked. And they started treating me less like a vendor and more like a consultant.

That's the relationship you're building toward.

The Real Reason to Diversify

I asked Josh what got him interested in sponsorships in the first place. He quoted something I'd apparently said on Jay Clouse's podcast — something about diversifying revenue streams as protection against market disruption.

He'd been in web design long enough to feel the tremors of AI. Lovable, all these no-code tools — you don't need to be paranoid to see the writing on the wall. The way people build websites is changing.

When I left my medical device engineering job in 2014, everyone thought I was insane. New kid. No health insurance. Starting a creator business. But my logic was simple: in my nine-to-five, I had one revenue stream. If they fire me, it goes to zero.

My wife April and I now have 11 revenue streams. And even within the sponsorship bucket, it's diversified across dozens of brands. If one sponsor pulls out, it barely registers.

That's not just financial strategy. That's peace of mind.

But — and I mean this — none of it matters if it doesn't serve your audience. Every revenue stream, every sponsor, every alliance has to pass that test first. If it doesn't make your people's lives measurably better, don't do it.

If this conversation made you realize you've been leaving money on the table, the next step is getting your hands on Sponsor Magnet — the whole book is essentially an extended version of everything Josh and I covered here, plus a lot more.

And if you want this kind of one-on-one coaching for your own deals, Wizard's Guild is where that happens. Live coaching calls twice a month, support every Tuesday and Thursday, and we take 0% of your sponsorship revenue. You keep everything you earn.

What's the one thing you've been giving away for free — in your affiliate promotions, your content, your recommendations — that a brand would actually pay for?