Roll With It

Overview

Roll With It is a remixable workshop and AI-powered experience built to help youth and emerging creatives turn lived experience into tangible business ideas—fast. The workshop is run by a human facilitator or a custom GPT assistant named Nova, built on top of the Sentinel-16 system.

Designed as both a teaching tool and a proof of concept, Roll With It shows how AI co-facilitators can scale reflection, strategy, and ideation—especially for under-resourced or first-time founders.

Problem: Traditional Strategy Tools Exclude Emerging Creators

When I saw a job opportunity to run design-thinking workshops for teens, I realized I had the skills—but not the resume. I’d never “officially” led youth programs. So I built one.

Roll With It wasn’t just a workshop. It was proof.
Proof that reflection, remix, and GPT-powered facilitation could spark strategy faster than most people expect.

Solution: A GPT-Powered Workshop Model

At the core of Roll With It is Nova GPT—an AI facilitator trained on custom prompts and methods to help participants:

• Reflect on lived experience
• Map values to problems worth solving
• Ideate business or product solutions (Crazy 8s remix)
• Prioritize their ideas using NOVA Coins
• Build out a Problem → Offer → Result storyboard
• Capture the essence in a Roll Card with next steps

Nova can run this solo (in ~20–30 min) or as co-pilot to a live human facilitator. The full in-person session takes ~1h 45m.

AI Strategy Context: Why GPT Is More Than Just Hype

The Roll With It approach aligns with what leading companies across industries are learning:

GPT-based tools don’t just assist—they drive strategy.

According to Deloitte, 74% of GenAI projects have already met or exceeded ROI expectations. MIT’s 2023 study showed workers performed 40% faster and wrote with 18% higher quality when assisted by GPT.

In youth contexts, GPT becomes more than a productivity booster—it’s an equalizer. It gives students a sounding board, reflection partner, and business strategist in one.

Nova GPT is that partner—built for clarity, self-trust, and action.

Workshop Breakdown

Each of these blocks can be executed with or without Nova GPT. The AI model adapts to timing and tone—making the workshop feel fluid and human-paced.

Strategic Impact

Roll With It x Nova GPT helps youth:

• Build without needing permission
• Reflect and plan without needing a team
• Launch ideas without needing funding

It’s not just a curriculum. It’s infrastructure for first-time founders and creatives.

The hybrid model also makes it scalable:

• Run it live in the South Bronx.
• Run it solo in a dorm.
• Run it in the cloud across classrooms.

ROI Potential:

• Lower cost of delivery (1 facilitator or none)
• Faster idea-to-action cycles
• Higher engagement via AI-assisted pacing
• Measurable skill-building outcomes (ideation, storytelling, self-direction)

Positioning in the AI Landscape

Roll With It joins the ranks of:

• Duolingo Max, which used GPT to drive record subscriber growth
• Khan Academy’s Khanmigo, which reimagines tutoring with GPT
• Salesforce & HubSpot, which now embed GPT into strategy workflows
• Coca-Cola, which used GPT in co-creation campaigns and global marketing
• PwC & Bain, who’ve embedded GPT in thousands of client-facing strategy projects

But unlike those examples, Roll With It isn’t for corporate leaders.
It’s for first-timers, teenagers, creative hustlers—those with ideas but no infrastructure.

Founder’s Note

“I built Roll With It because I never had anything like it. I didn’t grow up with design thinking. I didn’t have a mentor walking me through product strategy. But I did have lived experience. And that’s where strategy starts. Nova GPT helps youth realize: You already have value. Let’s build from there.”

Next Steps

Live pilots: Testing with youth in NYC
Facilitator version: Creating Ritual Packs for educators
Product roadmap: Embedding Nova into Barlo’s onboarding + strategy stack
Licensing: Seeking partnerships with youth accelerators and school programs

Try It or Collaborate

Explore the Workshop:
docs.jmthecreative.com/roll-with-it

Let’s link if you want to:

• Pilot it in your school or org
• License Nova GPT for youth programs
• Collaborate on hybrid AI/human learning tools

Contact: hi@jmthecreative.com