April and I were sitting on the couch watching TV when a commercial came on.

It was her. Her footage. From her YouTube video.

We turned to each other at the same time. "Did we give them the rights to do that?"

We pulled up the contract. Sure enough, we had signed away broadcast TV rights. Not for a fee. Not for a big check. For $2,000 in clothing credit.

We were broke back then. A clothing brand offered her a free wardrobe in exchange for one video, and she said, "New wardrobe? Let's go." The agreement looked fine. We didn't know any lawyers. We didn't speak legalese. Probably fine, right?

It wasn't fine.

I told that story recently when I sat down with Tori Dunlap on her show, Financial Feminist. Tori's built one of the biggest personal finance brands for women on the internet, and she asked me the questions I wish someone had asked me 15 years ago. So I want to walk you through the parts of that conversation that matter most if brand deals are a real line item in your business.

Stop Spitting Back a Number

Tori asked me if there's a pattern to who undercharges.

There is. Women undercharge. I've watched it happen across hundreds of deals, both in my coaching and back when I ran my agency.

A lot of it goes back to childhood. If money was tight in your house, or it was taboo to talk about, that doesn't just disappear when a brand with fancy marketers and a big budget lands in your inbox. You think, "Who am I to ask for more? Who am I to counter?" So you say yes, thank you, and you take whatever's offered.

Here's the thing. That brand needs your distribution as much as you want their check.

And the most common way I see you hand that leverage away? A brand asks, "What's your rate?" and you immediately spit back a number. $1,500. $5,000. Whatever it is.

Then one of two things happens. They ghost you. Or they lowball you.

Instead, try this: "Super excited about this. I'd love to hop on a call to learn more about your objectives for collaborating."

Then get on that call and ask questions. What are you launching this year? What features are you pushing? Are tariffs wrecking your supply chain so you can't keep product on the shelf? Act genuinely interested in their business. They reached out to you, which means they have a marketing problem they're trying to solve.

At the end of the call, you say, "This was great. Let me put together a custom proposal for how I can help you hit that outcome."

Then you come back with packages. Package one, two, three, four.

There it is. Now the question isn't "Do we work with this creator?" It's "Which package do we pick?"

Tori pointed out that the same logic works in job interviews. Never give your salary expectation after a 20-minute recruiter screen. You don't have enough information to price yourself yet. Neither do you after one inbound email.

Get Out of the Commodity Bin

Tori brought up something I hear constantly. Big, sexy brands get away with paying nothing because so many creators will work for them for free. And every free deal sets the precedent for the next person.

She's right. But complaining about it doesn't get you paid.

What gets you paid is giving the brand a reason to stop treating you like a raw number in a spreadsheet of 100,000 interchangeable creators.

So when an offer comes in that's free or insultingly low, you respond with what makes you different. "I've got a private community with 2,000 of my most engaged members." Or, "I run in-person masterminds with 50 women, and it's way more impactful than anything you've activated before."

You want the brand to think, "Wait, this person is approaching partnerships differently. Let's get them on the phone."

That's a pattern break. And once you break the pattern, you're no longer competing on price.

Oh, and Tori asked me in the rapid-fire round whether free product instead of money is ever worth it.

Absolutely not. Never.

The One Word That Should Make You Put the Pen Down

Back to that TV commercial.

If you're looking at a partnership agreement and wondering which gotchas actually matter, start here. Search for perpetual or perpetuity.

That word means the brand gets to use your content, your name, and your likeness forever. You should never agree to it.

Think about it. You blow up. Your business is ten times bigger. And a brand from six years ago, one you might not even support anymore, is still running ads with your face on them. Simu Liu can laugh about his old stock photos now, but most of us aren't Marvel action stars.

Next, watch exclusivity. When a brand says you can't work with any competitor for a period of time, that's a direct opportunity cost. You can negotiate it. Shorten the term. Narrow the category so it's a handful of named competitors instead of an entire industry.

Tori added one I completely agree with: get an out clause. She's been in situations where she needed one and didn't have it, and situations where she had one and used it. Very different realities.

Given the opportunity, a brand will take as much as you let them. That's not evil. That's just business. Your job is to know what you're signing.

Why I'd Never Hand Someone 20%

This is the topic that fills my DMs with angry managers. I said it on Tori's show and I'll say it again here. I think hiring a talent manager is one of the worst mistakes you can make as a creator.

I didn't talk about this publicly for years. I have a lot of friends in talent management. But April and I have had terrible experiences with representation, and we've been independent for over a decade now. This is my truth.

Here's the story that changed my mind for good.

When I ran my ad agency, brands hired me. I wasn't representing talent. A brand would say, "Go run this campaign," and we'd build a shortlist of creators. The brand would narrow it down to five. We'd go to one of those creators' profiles and find their manager's email in the bio.

So we'd email the manager about their client.

And the manager would immediately reply, "Sure, she might be interested. But do you need more people? I've got 19 others on my roster. Here are their rates."

What would you do if you were a less scrupulous agency? You'd say, "Great, those three are cheaper. Let's go with them."

If the only way your rep eats is a cut of your deals, they don't care whether their 20% comes from you or from someone else on their roster. That's the incentive structure. A flat retainer for someone actively hunting deals for you is a different conversation. But if they're a glorified inbox manager responding to inbound you would have gotten anyway? Learn it yourself, or hire someone onto your own team to own it.

Now the math. April and I have made over $5 million in brand partnerships. Had we paid 20% to management, that's a million dollars.

That's a house. That's a college fund. That's serious money.

Tori has her own version. She has an episode literally called This Mistake Cost Me Half a Million Dollars about selling podcast ads through networks. She was paying for her entire production team and still handing over 20 to 30% of revenue, while the same advertisers she attracted got spread across the rest of the network's shows.

I wrote Sponsor Magnet specifically to democratize this. You don't need a gatekeeper's permission to do brand deals.

Brands Are Talking About You Behind Your Back

Running the agency rewired everything I believed about partnerships.

Before, April and I were landing $5K, $10K, $20K deals and thought we had it figured out. Then I was in the boardroom, and the conversation was completely different. "We don't want to pay one creator $10K. We want to spend a million dollars across 300 creators. What platforms? What types of partners?"

I also heard the other side. "Don't ever send us that person again. We'd never work with them, and here's why."

A legacy conglomerate has a totally different risk profile than a scrappy direct-to-consumer startup that wants edgy talent. And if your content is clickbait headlines and constant drama, your dream brands are quietly crossing you off the list. They'll never tell you that.

I'm not saying water yourself down. Speak your truth. But you're running a business, and the people you want to be in business with have their own editorial standards. Know which brands you're building for.

Your Follower Count Isn't the Problem

The biggest myth about who gets sponsored? That you need a huge audience.

Most of the people I coach have smaller followings and much deeper niches.

Dr. Aleks runs a podcast called Digital Pathology Place. She gets hundreds or thousands of downloads. Not hundreds of thousands. And she's crushing it with sponsorships because she's a massive fish in a tiny pond.

We have someone in Wizard's Guild who runs hyper-local breakfast clubs around Boise, Idaho. Twenty-five people show up. She gets sponsored.

How? She pitches the local coffee chain that's trying to drive foot traffic. The club meets at the shop, everyone creates content there and tags the brand. For a small business, that's worth a multi-thousand-dollar investment.

Tori went full-time on Her First $100K with 9,000 Instagram followers. She was making as much from her business as she was at her $77,000 corporate job.

It's not about size. It's about relevance and format.

Survey Your People Before You Pitch Anyone

Tori asked me for the one thing every person with an audience should do today.

Survey them.

Your audience isn't a faceless horde. They're individuals. Throw up a story poll. Ask them to DM you. Are they married? Kids? What jobs do they have? What problems are they wrestling with? What tools and products are they using right now?

Then take that data to brands. "My audience is already interested in what you're building. I'd love to put you in front of all of them."

Here's what I noticed when I started doing this. Most creators build their dream brand list based on what they love. It's not about you. It's about how a partner can solve a problem for your audience.

That's one of the things I break down every week in my free sponsorship newsletter, if you want more of this.

Turn One Deal Into a Relationship

I shared my eight-step framework with Tori: pitch, negotiate, contract, concept, produce, feedback, publish, and analyze.

The magic is in step eight. When you analyze the results with the brand, you're already pitching the next collaboration.

Tori's had Squarespace as a partner for over five years. That's the dream. You find a partner who values you, and you rinse and repeat. Brand deals don't have to mean starting from zero every single month.

Climbing Cringe Mountain

April started her YouTube channel in 2009, before anyone was really making money online. She didn't have friends in real life who were into beauty and skincare, so she made her own corner of the internet.

As we started creating together, the trolls came out of the woodwork. Awful comments about the most innocent moments. And the moderation tools back then were terrible.

What we learned: someone doing better than you will never cut you down. It's always people looking up.

I call it climbing cringe mountain. At the bottom, people throw tomatoes. Strangers, and sometimes friends and family. "What are you doing? That's so cringe."

Then you get near the summit. Opportunities start showing up. And suddenly those same people are asking, "How are you doing that? Can you teach me?"

Everyone wants to make fun of you until you start winning.

We didn't jump in full-time, either. For years I was in medical devices with an engineering degree and an MBA. April was teaching and waiting tables. We'd work the 9-to-5, then come home and pour everything into this tiny business from 5 to 10. People didn't get it. Why work so hard? Go watch TV.

But there was a feeling we couldn't shake that something more was waiting. There's a season of intensity that building something requires. Screw what's normal. Strive to be abnormal.

Yes, I Cried on Tori's Show

Tori has a running joke that she always cries on her podcast. I'm apparently the first guest to beat her to it.

Here's what happened.

As my business has grown, everyone has had an opinion. Scale it, Justin. Run paid ads. Hire a bunch of coaches. Certify your methodology.

But my kids are 12 and 9. These next few years are magic. It won't be long before they'd rather hang out with their friends than with April and me, and not long after that they'll be out of the house.

So no, I don't want to scale. I want the freedom to say yes when my kid bursts into my office at 3 PM and asks me to throw the ball in the front yard.

If someone mutters, "He just has a lifestyle business," I'm proud of that.

Tori said something afterward that stuck with me. The only reason I get to make that choice is because I put in the work to build something. That's what success actually looks like. Deciding how much gasoline to pour on the fire, instead of being forced to.

You get to invent the business you want. And you might not even want a full-time creator business. Adriana Lopez, a DIY creator I interviewed for my audiobook, is a stay-at-home mom with a child on the spectrum. Her brand deals fund family trips to the Four Seasons and the Ritz-Carlton every couple of months. That extra income has been incredibly empowering for her family.

That's the reality for most creators. Not a media empire. A few extra thousand dollars a month that changes how your family lives.

Before You Talk Yourself Out of It

Tori's last question: what should someone do before they talk themselves out of starting?

My first answer was to cut out the toxic people telling you that you can't.

She pushed back. "What if that toxic person is you?"

Good question. My honest answer was therapy. Do the internal work to figure out why you're your own harshest critic. The place to aim for is being proud of trying, regardless of the outcome.

And then stop thinking about the giant impact you want to have someday. Keep it on the vision board, sure. But ask a smaller question today.

How can I help one person?

That's how I started teaching sponsorships. Voice notes in the DMs. One creator, one deal, one better negotiation. Then that person told a friend. Then I asked for a testimonial, even though I was terrified they'd say no, and used it to get the next client.

So here's my challenge to you. Look at the last brand inquiry sitting in your inbox. Did you answer it with a number, or with a conversation?

Grab my book, Sponsor Magnet, to learn how to transform your influence into income: https://www.sponsormagnet.com/

Want one-on-one sponsorship coaching? Join Wizard's Guild: https://www.wizardsguild.com