Liz was mortified.

She'd just filmed an entire sponsored video for Riverside—the podcast recording software we're literally using right now—without sending them a script first. Without getting approval. Without any of the checks and balances that prevent sponsorship disasters.

She sent them the finished video, proud of her work.

Their response? "That's not what we wanted."

By then, she'd already paid her editor. Already sunk money into production. The whole thing was a mess.

"I thought maybe I should cancel the sponsorship. So I kind of emailed back like maybe we should stop. And this was like years ago and then it was just a disaster and I felt so bad."

They ended up posting what she filmed. Neither party felt good about it. Riverside told her directly they didn't like it.

"I'm haunted every time I go on a podcast. It's that one brand deal that went wrong. So I want a redo. I'm a little mortified on that one."

But here's the thing about spectacular failures: sometimes they're your best teachers.

The Email That Cost Her $500

The Riverside disaster wasn't even Liz's worst sponsorship horror story.

That honor goes to Shortform—a book summary service she was genuinely excited to work with.

"We went back and forth and I had asked them two questions. They said yes to one. So I asked if they wanted to sponsor a video for like I think it was like 500 bucks or something. And they said yes, but they were saying yes to a different question because I had too much going on in that email."

She filmed the video. Sent them an invoice.

"They're like, 'We never agreed to do that.' And I'm pretty sure I went on Twitter and I'm like, 'I'm done. I'm done.'"

Then she went back through the email chain. And realized the mistake was entirely hers.

"I totally misread it. So I'm mortified that I sent this. I had to void the invoice. I'm thinking I'm getting 500 bucks. No, I just did a bunch of work for free. It's completely my fault."

Two massive sponsorship failures in a row. Both completely her fault. Both with companies that were growing rapidly and could've been amazing long-term partners.

Most creators would've quit at this point.

The Six-Month Break That Changed Everything

"I stopped for a while. I think I gave a six-month to a year break. I just swore off sponsorships. I'm frustrated. I'm not communicating right. So I started focusing on other parts of the business."

During that break, Liz doubled her subscriber count. She got comfortable with her brand. She figured out her presence on camera. She clarified the direction of her channel.

Then she came back to sponsorships with a completely different approach.

"I had a really positive experience with a couple of them. So I started out with Scribe and they were wanting me—it was very clear that they wanted a person who was really like a dedicated user of the software. So it felt really good."

The key difference? Liz stopped being just a number on someone's spreadsheet. She started looking for brands where there was genuine mutual investment.

"I've had sponsors come in and go, 'I just want to talk over email. We're just going to communicate over email.' I'm like, 'What? You don't want to meet me?' Like that's kind of weird. It's a volume game for some people, which I get, but for me I'm looking for long-term partners."

The Lesson Most Creators Miss

Here's what Liz figured out that most creators never do: Your early sponsorship disasters aren't reasons to quit. They're the tuition you pay for your education.

The Riverside deal taught her to always send a script before touching a camera. "There's so much effort that goes into once you film it. Every other sponsorship after that was great."

The Shortform disaster taught her to get on calls instead of trying to negotiate complex deals over email. When there's actual money on the line and multiple moving parts, a five-minute conversation prevents catastrophic misunderstandings.

But the biggest shift was internal. She stopped treating sponsorships as transactions and started treating them as partnerships.

"I want to be as invested in their company as they are in me. I want to see their company succeed. I don't want just 500 bucks or a thousand bucks. I want to actually see their company in Forbes' top software products."

This isn't just feel-good philosophy. It fundamentally changes how you approach brand relationships.

The Outbound Strategy That Actually Works

One pattern that emerged from our conversation: Liz's best sponsorships came from brands she reached out to, not brands that reached out to her.

"If all you're doing is responding to inbound—yes, no, is this a good fit, yes, no—it's easy to feel like you're just another number on a spreadsheet. Like, 'Okay, we're going to work with 20 creators and oh, it's too much money, fine, we'll delete that row.'"

When you're the one leading the pitch, saying "Here's what I can do for you," the dynamic completely shifts. It might be a longer sales cycle. You might have to convince them. But the deal will probably work out way better in the end.

Liz's new strategy? Only pitching brands she actually uses.

"I'm using that all the time. So it's very easy for me to talk about it and film about it. That's going to be my new strategy—I'm only going to talk about brands and things that I currently use."

She even set up a Notion board to track her sponsorship pipeline: prospecting, in progress, invoicing, done, with links to the videos. A real system for a real revenue stream.

What Liz Would Tell Her Past Self

If Liz could go back and give herself advice before those early disasters, here's what she'd say:

1. Get on a call before you do anything.

Email is great for logistics. It's terrible for negotiating creative direction. A five-minute video call prevents $500 mistakes.

2. Always send the script before filming.

No exceptions. Even if you're excited. Even if you think you know what they want. Get approval on the script before you touch the camera.

3. One question per email when money is involved.

Don't ask multiple questions about deliverables and pricing in the same email. You will misinterpret which thing they're saying yes to.

4. Early failures are tuition, not verdicts.

Your first few sponsorship disasters don't mean "sponsorships aren't for me." They mean you're learning. Take a break if you need to. But come back smarter.

5. Focus on long-term partners, not one-off checks.

When you actually care about the company's success and want to see them win, everything about the partnership gets easier. You make better content. They're more patient with your process. Both parties are more invested.

The Companies She Wants to Redo

Both Riverside and Shortform have grown significantly since those early disasters. Liz watches them succeed and thinks about what could have been.

"I really want to redo both of those. They were really good companies that I wanted to associate myself with. I thought it was going to be so good."

Maybe after this episode comes out, she'll email both of them. Show them this post. Say, "Look, I'm very conciliatory here. This was all on me. But I really would love a chance to redeem myself."

Because here's the beautiful thing about the creator economy: bridges you think are burned often aren't. People understand that everyone starts somewhere. They remember creators who own their mistakes and come back better.

Liz isn't the same creator who fumbled those early deals. She's doubled her audience. She's worked out her on-camera presence. She has a system for managing partnerships. She knows what she's doing now.

And ironically? Those disasters are a big part of why she's good at this now.

What This Means for Your Sponsorship Journey

If you're reading this and thinking about your own sponsorship horror stories, here's what you need to understand:

Everyone has them.

Every creator who's been doing this long enough has fumbled a deal. Misread an email. Over-promised and under-delivered. Said yes to something they shouldn't have. Burned a bridge they wish they hadn't.

The question isn't whether you'll make mistakes. It's whether you'll learn from them.

Liz could have let those two disasters define her relationship with sponsorships forever. Instead, she took a break, figured out what went wrong, and came back with a completely different approach.

Now she has a real sponsorship business. Long-term partners. A system that works. And two really good stories about what not to do.

If you're just starting out with sponsorships and you feel overwhelmed by all the ways things could go wrong, that's actually a good sign. It means you care about doing it right.

Read Sponsor Magnet. Learn the frameworks. Understand the process. Then go out there and inevitably make some mistakes anyway, because that's how you actually learn.

Just maybe send the script before you film.

And definitely don't try to negotiate complex deals over email with multiple questions in one message.

And absolutely get on a call with the brand before you commit to anything.

Or, you know, join Wizard's Guild where we help you avoid these disasters on our bi-weekly coaching calls before they happen instead of learning the hard way.

Because while early failures are great teachers, having someone point out the obvious mistakes before you make them is even better.

Sometimes the best lessons come from the deals that went wrong. As long as you actually learn from them.