Hey Jumpers,
I really appreciate the 57% average open rate from the last four Innovator Briefs!
For today’s brief, I want to take you behind the scenes on an AI creative project I’m working on.
I was going to wait until it was finished before sharing, but I’m just too damn excited about the work.
(Quick heads-up: In-between writing these briefs I’m publishing longer essays that don’t go out by email. I don’t want to bombard your inbox, but I do want to formalize some of my thinking and make it available to you. The first three are pinned on the JumpIntoTheFuture.com homepage. More to come.)
Ok, let’s jump in.
Scope: Build a creative concept and social campaign that is AI-native
Client: Chuckle Rum
Deliverables:
Concept + campaign that lean into AI’s strengths.
End-to-end AI creative workflow + prompt library so the client can scale infinitely.
10 AI creative assets that serve as the foundation for the initiative (final assets will be shared soon)
Here’s what we’ll cover below:
My two strategy pillars for AI social content
Quick overview of the client
A one-slide framework for this project
The campaign concept we came up with
The three creative options we presented
The strategy for bringing the fruit characters to life in social
The transition from being an IP renter to IP owner
My Two Strategy Pillars for AI Social Content
Here’s my POV and strategic framing when it comes to creating AI social content for brands:
Never present something as real when it is not.
Aim to trigger the imagination of your audience. Emphasis on imagination!
That’s it, I keep it pretty simple. There are of course other elements I consider, but those two are my non-negotiables right now.
The first point is fairly straight forward. I don’t think I need to explain why it wouldn’t be smart for a brand to trick their audience into thinking something is real.
The second point though is worth exploring and is a big driver in the work we’re doing for Chuckle.
So why do I care so much about imagination?
Lot’s of agencies spend endless time obsessing over “story” and “narrative.” Frankly, the term brand narrative makes me gag, and “let’s tell your brand’s story” isn’t much better. Both phrases start from the company’s point of view, not the audience’s.
Instead, brands should work harder to spark the audience’s imagination. That shift from telling your story to triggering their imagination changes everything.
Here’s why I like the shift in thinking:
It puts a brand’s audience and customer at the center of the discussion. From the very first strategy session, we’re talking about the customer, not the brand.
Story and narrative do not inherently imply that you will tap into the customer’s imagination.
When someone’s imagination is activated, everything changes. They become more open and receptive to new ideas and information. They enter a kind of play mode. Their recall improves too.
AI is far better at creating content that will tap into someone’s imagination than it is at creating content that looks and feels real.
An audience doesn’t care if content was created with AI if you’re unlocking their imagination. If you’re helping them play pretend, all the walls come down.
Client / Brand Overview: Chuckle Rum
Chuckle is a fruity, high-proof rum.
The brand leans heavily into the comedy scene.
They’ve done an incredible job curating a network of under-the-radar comedy creators on Instagram.
They primarily position themselves against Fireball Whiskey. Both brands are inexpensive “let’s have fun” type of spirits.
With Chuckle, you get a high-proof, fruity shot that’s relatively easy to take down, compared to the harshness of Fireball. Chuckle is also a lot more versatile when it comes to mixing fruity-driven cocktails.
With that context, let’s jump into how AI fits into the equation.
AI-Powered Creative Engine For Social
This is the framework I created to capture the inputs, workflow, and AI components for this project.
As mentioned above, this framework is the one-slide version of the end-to-end AI creative workflow + prompt library that is one of the core deliverables for this project.
A big insight that most people have when seeing this slide is how many AI tools are actually needed to create something really good.
For the people out there, that say AI is going to replace agencies, I just don’t see it. There’s an entirely new type of creative process being born and humans are just as important as ever.
In fact, everyone should be thinking about how to create their own personal agent. An agent that can work within larger systems. An agent you take from company to company.
Campaign Concept: Chuckle Fruit Comedy Club
For the campaign, we landed on creating the Chuckle Fruit Comedy Club.
There are five fruits in Chuckle’s recipe so naturally there are five characters we can bring to life.
The personality of each fruit represents a persona within Chuckle’s core customer base.
Apple: "Brent" the Frat Guy — 21-year-old frat guy, currently a senior at State University, who loves to hang with his bros and party
Strawberry: "Jessie" the Comic Influencer — 26-year-old woman who is a local up-and-coming standup comedian and also comedy content micro-influencer
Apricot: "Dre" the Connector - 30-year-old man who is the unofficial leader of his friend group, always has the hookup or plans for the weekend, and knows every bouncer and bartender in town
Watermelon: "Tracy" the Fun Mom — 40-year-old self-proclaimed "fun mom" who is constantly busy getting the kids to and from all their activities, but loves to enjoy a good strong fruity drink with the girls on the weekend
Lime: "Sebastian" the Life of the Party — 28-year-old man who tells it like it is and has an extremely booked social calendar - he loves a show whether it's standup comedy, trivia night, live music, or charades at home, and believes they all should be enjoyed with a stiff drink and good friends around
What’s fun about this campaign is that it’s not the first time I’ve worked with fruit at the forefront of innovation.
The first social campaign I ever led was building Fruit of the Loom’s presence on Facebook back in 2012!
Here Are The Three Creative Directions We Presented
Option three was the winner.
Option 1: Stop-motion vibe with felt texture
Option 2: 3-D fruit in suits & shades (gamer centric)
Option 3 — Winner: Real fruit, googly eyes, subtle animation
Bringing The Characters To Life
After we chose the creative direction, we produced some rough assets to explore how they felt.
We decided the best way to introduce these characters to the Chuckle Instagram audience was to have them audition for their role in the Chuckle Fruit Comedy Club.
Here are some rough mockups of that direction.
Here’s How The Concept Feels Outside of the Comedy Club
You can image just how funny and sassy this 40-year-old watermelon mom will be!
Here’s the working script for her audition video.
“Hi! I’m Tracy. I’ve got three kids, four calendars, and one rule: Mom’s weekend starts when the juice hits the Stanley. And baby, Chuckle is that juice.”
The Stanley tie in really got a chuckle out of me. 🙂
From IP Renter to IP Owner
What makes this campaign exciting isn’t just the characters. It’s what they represent for Chuckle’s long-term strategy.
Until now, Chuckle has primarily relied on rented IP by partnering with external comedy creators to fuel content. That model works, but it comes with limitations.
With the Chuckle Fruit Comedy Club, the brand is beginning to create and own its own characters and world. These new assets don’t replace their creator partnerships. They expand what’s possible.
This gives Chuckle more firepower, more scale, and more control. It’s a creative platform they fully own and can build on infinitely.
The Future Will Be Wild
As this campaign moves into its final stages, we’re not just thinking about content, we’re thinking about scale, distribution, and reach.
We’re currently at step 6 in the AI-powered creative workflow above. Once the final assets are ready, I’ll be sharing them here.
But more importantly, I’ll share how work like this can evolve from organic social content into something deeper, a system that builds and powers community.
For now, I’ll leave you with this: community remix.
If you enjoyed today’s brief, please feel free to reply and let me know! Heck, if you didn’t like it, you can let me know that too, haha.
Switching gears a bit.
I’ve teamed up with Isaac to host a livestream series where we talk with founders and leaders from top AI companies to vibe-code products live, in real time.
In last week’s episode, we built an AI-powered competitive intelligence agent with Martin Skow Røed, CTO and Co-Founder of Databutton, a platform that helps non-devs build AI agents fast. Think custom agents that automate workflows, analyze data, and generate insights using natural language.
We started by briefing ChatGPT with the assignment, then kicked off the build using Databutton’s agentic builder. The result? A working prototype, live on the stream.
