We built a game called the Sponsor Fishbowl Spinner.

Random brand. Random description. 60 seconds on the clock. Go.

No preparation. No ChatGPT. No perfectly crafted email template. Just you, a timer, and a fake brand that sells premium ice cubes with flavor cores.

Welcome to the realest sponsorship training you'll ever get.

Because here's what nobody tells you: You can write the perfect pitch email with AI help. But when you're on a phone call with a brand and they throw you a curveball? That's when most creators completely fall apart.

So today, my co-host Joe Casabona and I are putting ourselves through the exact same test we put our Wizard's Guild coaching clients through. And we're breaking down every mistake in real time.

Round 1: Frost Kit (Premium Ice Cubes With Flavor Cores)

Joe went first. The timer started.

"Frost Kit, I noticed you just came out with your new strawberry flavor core. I think that's perfect for summer. I was curious if you've ever run any summer promotion, especially in parts of the United States that are especially hot. Maybe this could be a geo-targeted campaign.

Basically, I can create some content—15 to 30-second ads that you run on Facebook and Instagram. I don't even have to upload them on my platforms, but you can run those ads in parts of the US where it gets especially hot. I'm curious if you've ever tried doing that. I can create five ads for you. Curious if you might be able to hop on a call Tuesday to chat through this."

Time to spare.

Joe's Self-Audit

"I did not give them any O in the ROPE. I didn't talk about myself at all. I should have linked something back to what I do—why am I qualified? That's the balance, right? People focus too much on themselves, but you do need to talk about yourself a little bit."

He's right. But here's what he did brilliantly: He didn't focus on himself as the star. He focused on solving their problem.

The UGC (user-generated content) angle? Chef's kiss. "You don't even need to know who I am. You can tell how charismatic I am. Just use these ads."

And the geo-targeting insight? That's consulting, not begging.

The Hidden Lesson About Seasonal Campaigns

Here's what most creators don't realize: Brands run different versions of creatives for different parts of the country.

If you're a brand selling ice products, you're running very different ads in Texas, California, and Florida than you are in the Midwest or Northeast where there's still snow.

Joe started making up the pitch as he went. He didn't know he was pitching UGC until halfway through. But once he got there, he realized: "Oh yeah, this is good for parts of the US that get hotter."

That's the magic of thinking on your feet. You discover angles you'd never find in a perfectly polished email.

Round 2: Fit Ridge (Wearable Ring That Measures Posture)

My turn.

"Hey Fit Ridge, I recently saw you released your wearable ring that measures posture. I'm a solopreneur that works from home. I have a sit-stand desk and my audience is really interested in making sure they have ergonomic stuff at their desk.

What I'd love to do for you is a YouTube video reviewing the wearable ring, measuring and sharing my own posture, then creating three short-form videos and give you paid usage rights for 30 days. I'd be really happy to share a case study I did with Elgato Stream Deck—another thing that's always on my desk. We had a very successful campaign with them. What are your thoughts?"

Boom. 12 seconds to spare.

My Self-Audit

"I didn't really talk about any of their own content. I talked about my audience, but I didn't mention specific organic content even though I have a ton of office stuff. This was a really good fit for me. Fit Ridge, call your boy.

I was light on the deliverables. I varied it up on the content types, but not much on platforms."

Joe's feedback: "I think you did great. The Elgato thing—did you make that up?"

Me: "Yeah, I made that up."

That's the beauty of this exercise. You learn to think strategically in real time, even when you're inventing case studies on the spot.

The ChatGPT Problem

Joe nailed why this exercise matters: "Especially in the age of LLMs and ChatGPT and Claude, creators are getting more comfortable using those to write emails that sound pretty good. But when you're on a phone call with them, you kind of can't use an LLM."

Exactly.

You can write the perfect pitch with AI. But when you're negotiating? When a brand asks a question you don't expect? When they throw an objection at you?

That's when you need to know what to say without a script.

One of the biggest learnings from Sponsor Games—our in-person event—is that creators get really nervous on live calls. They get asked a question they don't know the answer to, they fumble, and they feel like they need an answer on the spot.

This exercise makes you think on your feet. Because you're not always going to have ChatGPT there to hold your proverbial hand.

Round 3: Text Pilot (AI Tool That Helps You Write Better Emails)

Joe's turn again.

"Hey Text Pilot or hey Jim, I noticed on your website you don't have a lot of great information about why people would want to use Text Pilot over a native LLM like ChatGPT or Claude. I actually think that's a huge differentiator for Text Pilot.

I would love to create some content for your landing pages or your knowledge base that you can direct people to when prospective customers ask these objections—like 'Why would I pay for Text Pilot when I already pay for ChatGPT?'

I could create 10 videos for you. I actually have an outline already laid out of the 10 buckets of content that I think you need to overcome these types of objections. Curious if you have some time next week to chat about this."

Right around 50 seconds.

The Objection-Focused Pitch Strategy

Joe's pitch was brilliant because he identified a gap in their messaging and positioned himself as the solution.

"I've started thinking about objections consumers have as an angle to pitch brands," Joe explained. "A lot of times, this is a really interesting way to get them intrigued. This isn't just a creator—this is someone thinking more thoughtfully about our product than the random person being like 'Hey, do you have any campaigns to work with me?'"

He's not being condescending. He's not saying "Your copywriting sucks." He's saying: "Here's what I'm seeing in the market. Here's what me and my friends think is the perception about your brand. I actually think you could be winning more customers."

You're thinking about their problem, not just your money problem.

My one critique? Ten videos might feel like a project. Maybe bring that down to three to five so it feels more bite-sized. Give them something tangible they can react to without feeling overwhelmed.

The Kitchen Sink Problem

Joe brought up something we see constantly in our coaching program: Creators throw the kitchen sink at brands.

They're proactively trying to imagine what the brand is going to say back, so they preemptively address every objection. Including guarantees.

We literally had a coaching question yesterday where someone said in their pitch: "And if I don't get that many views, I'm going to do XYZ for you."

No shade. But here's the advice: Don't lead the witness.

Don't assume they're already on the defensive, skeptical about whether you can deliver. That's something creators fear, not something brands always bring up.

Joe said it best: "Don't negotiate against yourself. I've gotten asked for very few make-goods. If a brand asks 'What if?' then I might suggest a make-good. But I'm not going to make more work for myself, especially if the goal isn't necessarily views."

Round 4: Ship Maven (AI Shipping Assistant for Small Business)

Joe's final pitch.

"Hey Janine, I recently saw you did a video talking about drop shipping and how Ship Maven is the next evolution in drop shipping. I have a lot of solopreneurs in my audience who are really interested in expanding their offerings to something like drop shipping, and I think Ship Maven would be a great fit for them.

What I'd love to do for you is a five-minute video demo on how quickly solopreneurs can get set up with their side hustle using Ship Maven. I'd like to do four short-form videos for different use cases. And I'd love to have you sponsor my podcast for three months. We can even interview your founder if you'd like.

Something I recently did in another campaign was using an AI tool for improving writing. My audience loved it. I'd love to share the results of that campaign with you."

Timer up.

The Founder Interview Hack

The gem in this pitch? "We can even interview your founder if you'd like."

Don't underestimate this. Brands get so excited about mechanisms where their founder or someone on their marketing team gets to talk about what they're doing and share the founding story—in a place other than their own channels.

Even if there's no tangible business outcome like sales or trial signups, they love being able to share this around internally on Slack. "We got press!" Even if it was a sponsorship.

We have coaching clients who run this playbook regularly. A big part of their deliverables is interviewing people on the team—whether in person at their offices or virtually.

One client just flew out to the corporate offices of a company. The brand didn't ask for this. The creator said: "Hey, can I fly to your headquarters? I know your executive team is going to be there. Can I interview them for the content I'm creating for this partnership? Can we carve out three hours?"

The brand said "Of course."

The creator did this on their own time. But think about what that did:

• Established rapport with the CEO, CMO, and entire executive team

• Created great content with people who aren't usually in customer-facing content

• Made the creator unforgettable when renewal time comes

You think any other creator is willing to go out of pocket for something like that? But it's in service of the overall relationship.

It's easy to execute to the millionth degree.

The Big Lesson: Don't Be Afraid of Esoteric Pitches

As we were doing these pitches, Joe noticed something: "Sometimes we kind of got into the same old trope—social media assets, YouTube videos, podcast ads. Don't be afraid of pitching more esoteric things."

Like:

• "Let's do this at that trade show coming up. Let's hire a videographer and film it in your booth."

• "Let me come to your offices."

• "Let's go to one of your customers."

They're not going to say "That's a dumb idea." They're going to say "I love it. Let's talk through this."

It's all in the name of differentiation.

Joe did a live stream where they fielded questions from the audience about a company's new AI integration. The live stream didn't get a ton of views, but the brand loved it because it created something different.

And here's the kicker: "If you have the founder on, you can give them licensing to reuse this content, clip it up. That's a lot less work for them. You always want to make their job easier."

Want to Practice This Yourself?

This is something we do regularly inside Wizard's Guild. We have co-working sessions where we all show up at the same time on a given day. It's silent—we're not talking to each other—but it's an accountability thing.

We're drafting pitches. We're doing follow-ups. We're creating a habit out of nurturing brands and reaching out to new ones.

Because the game isn't just about writing one perfect email. It's about practicing so much that when you're on a live call and the brand throws you a curveball, you don't freeze.

You pivot. You consult. You show them you're thinking about their problem, not just your paycheck.