Here's the thing about the Content Entrepreneur Expo.
I've been going to CEX every single year since it started. But it's the belly of the beast when it comes to sponsorship skepticism.
These aren't your typical creators scrolling TikTok hoping for brand deals. They're course sellers. Coaches. Consultants. They've built solid businesses selling their own stuff, and when you mention sponsorships, they look at you like you just suggested they start an OnlyFans.
"Sponsorships? Why would I ever do that?"
There is nothing I love more than changing hearts and minds while helping people make more money.
So I gave myself a challenge: convince five entrepreneurs they're leaving massive amounts of cash on the table.
I predicted three objections:
Sponsorships will cannibalize my own sales
It'll hurt my credibility
My audience is too valuable to rent out
The catch? If anyone hit me with an objection I didn't predict, you get to ruthlessly mock me in the comments.
Let's go.
"I'd Rather Just Promote My Own Things to My Audience"
First conversation hits within minutes of walking the expo floor.
A podcast host. Paying for production. Promoting only her own consulting packages.
"I was literally just thinking about my podcast this morning," she said. "Do I want sponsors? No, because I'd rather promote my own things since I'm a service provider and I'm paying for the podcast to be produced."
Made sense. Part of it was also the work. She didn't have bandwidth to go find sponsors. She'd asked a few people—got ghosted by one, got the green light from another but then nothing.
"You know what? It's enough work to go ahead and start a podcast. I've just kind of let the idea die."
What if we could envision the most abundant version of reality? What if she could get more funding to support more episodes, more newsletters?
"I actually would say I probably wouldn't even necessarily need more newsletters or podcast episodes. I would just not have to work so hard to bring in all the clients. It would just be nice padding because I'm already going to do the podcast."
There it is.
"I've got a random idea for you."
"Love it."
"What if your sponsors are your current clients?"
"What? Hold on."
You know what I love? That reaction. She paused. Her brain was already racing ahead of my next sentence.
"I bet some of your current clients would love to get in front of your other clients."
She worked with food bloggers. Two of her clients sold services that other food bloggers need. One was actually the client who'd given her the green light that fizzled out.
You don't always have to get sponsorships from gigantic brands. It could be your clients. Smaller service providers. Solopreneurs. They may actually pay you quite a bit of money to get in front of new clients of theirs.
"That's a whole new revenue model. Getting those clients, having the contract, getting it locked in place—that's a whole other process I have zero developed."
How exciting.
Maybe we can make it happen. There's a book she could read about it.
"Every Tech Sponsor Wants Notion Content and It's Burning Me Out"
The Notion consultant knew exactly what she didn't want.
"My biggest objection is I primarily do tech content about software and I don't share most of my personal life online. But there's only so many tech businesses you can partner with without pigeonholing yourself. As a Notion consultant, everybody I've partnered with in the past wants content about them with Notion and it's really honestly kind of burnt me out."
She'd chosen other revenue opportunities instead—consulting and coaching.
"Are you fearful that if you hitched your horse to one brand, you couldn't work with their competitors?"
"Yes, that's usually a conversation unless it's kind of a complementary brand."
But here's what I noticed: her audience was telling her they wanted more of her personal life. They wanted less scripted content. There was a disconnect. Maybe there was a possibility, but how do you make it organic and natural without being like "today is sponsored by blah blah blah"?
"Is that a fear of how your audience will react, or is it your audience is too valuable?"
"I think it's the brand. It is hard to think about what brands. I can name you 20 brands right now but maybe the masses have no idea about that brand. Do you want to be part of getting a brand up to that level? I don't know if I want that level of responsibility unless I'm fully bought into the company."
That's something that might be interesting—not money in cash. Getting equity. Alice Mushrooms or something. Saying, "Hey, let me help you think through your content strategy."
Sponsorship and partnerships can look very different from brand to brand. It doesn't always have to be about cash. Whether it's in-kind, affiliate, commission-based, hybrid compensation with flat plus commission, all the way up to equity/partnership deals where you leverage your name, your likeness, your credibility, but also help the brand accomplish much more ambitious things.
Broadening the perspective of what a partnership is can be pretty exciting.
"Sponsorships Are Kind of Cheesy and Give Me the Ick"
The business coach didn't mince words.
"I think there's a sense of sponsorships are kind of cheesy, right? You don't really get authentic content from it. People are doing it because they want a freebie. So I have this kind of ick feeling around it."
Fair. It's always been in the back of her mind. Didn't feel like she was in a position to try it.
"In the course of your consulting and working with clients, are there tools, services, brands, companies you're gently steering them towards?"
"Yeah, I mean, there probably is. There's certainly either people I've worked with—other coaches who are doing things that aren't quite in my wheelhouse. A lot of stuff that comes up is mindset-related. I have a lot of really good people with psychology backgrounds and coaching backgrounds who can help with that piece."
What would it take for sponsorships not to give her the ick?
"To feel authentic. To feel like it's something that's part of my life and it's already integrated into what I do."
She'd started seeing a couple people she follows do a little bit more of that. At first she was like, "Hm."
"Do you worry your clients or audience would have that same reaction? 'I can't believe Barbara is doing a sponsorship'?"
"Sure. Absolutely. And it's funny because as we're talking about this, it's also that same fear my clients have about putting stuff out there. Someone is going to feel that way and you have to be okay with that."
There it is.
The really exciting part? If you do research on the challenges your audience and customers are having and use those insights to say, "Oh, I didn't realize they were having challenges with that. Maybe I should pitch that brand or that training company or that consultant on getting in front of my clients or audience."
It accomplishes all of those things. Win-win-win. You're making more money, which provides that baseline level of financial means. The company is excited because they get in front of people who have taken out their credit card and paid money to invest in their life, their business, their professional education. That represents a very prized type of potential customer for brands. And your audience, your clients are being served because they said they're having this issue and you brought this to them.
If you can have this holistic perspective on like it's not just a coercive ick thing—it's actually in service. But it often takes you initiating it. These brands or companies may not come to you. It's you reaching out, proposing something, being like, "Hey, I saw you were doing this. I would love to spread the word about that."
That's how these relationships start.
"I Don't Have Time to Pitch Sponsors Who Ghost Me"
The newsletter writer had battle scars.
"My biggest objection is the time it takes to pitch sponsors, deal with them, and then try to get a recurring sponsorship going. It would be so frustrating to do all the work upfront, never hear back or do a good sponsorship, and then they don't want to return for more. So it's hard to invest my time in growing my sponsorship strategy when I feel like maybe I should be doing other things to make money."
She had some recurring revenue with paid subscribers and other things. Felt more predictable.
Of the deals she'd done, certain ones were more successful than others. The best ones? Professional services for writers or marketers.
"Were these all inbound or did you pitch some?"
"Most were inbound last year. I did do some pitching, but for the most part that never went anywhere."
Here's the thing: there's probably people in your audience who would love to get in front of others.
"Have you asked your newsletter audience if anyone would be interested in sponsoring your newsletter?"
"No, I haven't."
Lowest-hanging fruit in the world. Just send an email: "Hey, hit reply to this email or click here and fill out this quick form if you're interested. Let's hop on a call and chat about how I can get you in front of however many thousand freelancers."
Probably fill out your inventory for quite a while with something pretty simple like that.
"Are we going to do it?"
"Yeah, let's do it."
"We're going to do it. All right, let's go."
"My Audience Isn't Big Enough for Sponsors to Care"
The multi-newsletter publisher had already dismissed his smaller properties.
"My main objection is we've got a couple newsletters and we also have our community. I don't think any of them are big enough for a sponsor to actually want to do something."
His smaller newsletter had a few hundred subscribers. The community had about 100 people. Just didn't have the traction.
"Now, our primary newsletter, we do have like 20,000 on there. So that's a nice size."
"Okay. I like your reaction. You're already beating my objection."
He laughed. "Yeah, my biggest thing is—as I say that I'm like okay 20,000 I should be able to sell that. But I guess it's the position. I don't know how to package this into something that says you should buy this."
His primary revenue stream was selling things directly to that audience. Most of his newsletters were very help-focused. Pretty light on the sell. He didn't want to put anything in there he didn't think was actually valuable just because someone gave him money.
Here's a mindset shift: the more niche the audience, the less you need.
If you could think of a company that wants to get in front of 20,000 educators, that's actually really hard to find a distribution channel that concentrated.
"You know, it's interesting. I was just talking with someone on one of our challenges about Canva and we were looking at their page and the types of promotions they have. They give discounts to Canva Pro to educators. So have they ever run a campaign straight to educators about that?"
"No idea."
"But we could."
"Maybe that's an interesting angle to potentially pitch them."
They may have never thought to run a campaign like that. Maybe it's a charitable give-back initiative or it's a priority for them to get their tools penetrated more in education.
"All right. For an accountability mechanism, in two weeks you're going to message me and say, 'Here's the pitch I've crafted for Canva or here's the pitch for an ed-tech company. What do you think, Justin?' And we're going to hit send on this pitch."
"Okay. Done. Committed."
"Deal. Let's go."
What Just Happened Here
Five different entrepreneurs. Five different objections.
But here's what I noticed: everyone was thinking too narrowly about what sponsorships could be.
Your current clients can become your sponsors. You can negotiate equity stakes instead of cash. You can formalize recommendations you already make. You can ask your existing audience who wants to sponsor you. You can pitch concentrated, niche audiences to brands desperate to reach them.
This is not a zero-sum game.
Screw what's normal. Strive to be abnormal.
The closer you get to brands, the closer you'll be to landing a sponsorship. Tag them on social media. Include a shout-out in your newsletter, then email them the blurb. The more you become a "known quantity," the quicker you'll be remembered when they recruit for their next campaign.
"But Justin, why would they pay me if I talk about them for free?"
When brands have specific marketing objectives, there are almost always talking points they need you to hit or sound bites they need you to say. Things you'd never do or say on your own in a simple shout-out.
Don't overthink this.
Which conversation resonated most with you? Got the same concerns? Had a mindset shift or two?
If you want help getting your first (or next) sponsorship deal, join our free newsletter where I share the exact strategies I used to make $5M+ in sponsorships.
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