Pressure test decisions, challenge assumptions, and make high-leverage moves to grow and monetize your newsletter faster.
This Playbook has 16 strategic prompts that use context, proven thinking models, and optimizations to spark high-quality conversations with AI.
The Playbook is broken down into the 4 Phases of newsletter growth.
Each Phase has 4 Strategic Prompts designed to help you think bigger, execute smarter, and avoid wasted effort.
Four prompts to set up your newsletter for long-term success by getting your positioning, publishing, and signup experience right.
✔ Clarify Positioning & Value Prop: Define exactly why your newsletter stands out ✔ Set Revenue Goal & Business Model: Choose a monetization strategy that fits your strengths ✔ Establish a Consistent Publishing Schedule: Balance frequency with quality so you never burn out ✔ Optimize the Signup Experience: Turn more visitors into subscribers with a frictionless onboarding flow
Four prompts to expand your reach, increase engagement, and build a subscriber base that actually converts.
✔ Leverage Existing Networks for Growth: Convert your Twitter, LinkedIn, and other audiences into subscribers ✔ Use AI for Content Ideation & Efficiency: Streamline research, writing, and editing without sacrificing originality ✔ Experiment with Distribution Channels: Find the highest-leverage ways to get more subscribers ✔ Improve Email Open Rates & Engagement: Test subject lines, segmentation, and messaging that keeps people reading
Four prompt to test, refine, and scale your revenue strategy without second-guessing.
✔ Validate Monetization Potential with Small Offers: Test consulting, sponsorships, or premium content before committing ✔ Refine Content to Align with Revenue Model: Adjust messaging so free readers naturally become paying customers ✔ Optimize Pricing & Conversion for Paid Models: Test different price points and positioning for maximum revenue ✔ Grow Newsletter List with Paid & Organic Strategies: Scale acquisition with ads, partnerships, and collaborations
Four prompts to automate, optimize, and refine your systems to increase revenue and sustainability.
✔ Automate Content & Growth Loops: Use AI for research, summarization, and content repurposing ✔ Build Recurring Revenue Streams: Reduce churn and increase lifetime value for long-term profitability ✔ Refine the Growth Flywheel: Double down on what works, remove bottlenecks, and streamline processes ✔ Optimize for Profit & Sustainability: Maximize revenue per subscriber while keeping your newsletter easy to run
“I thought I knew ChatGPT but this is truly next level.
I just had the most productive conversation about my business that I've had all year.”
Denyse A., founder at Chronicle Makers
❌ Most prompts give generic advice.Â
These prompts are built to make you think strategically, helping you avoid wasted effort and make better decisions at every stage.
❌ Most AI-generated responses go along with what you say.Â
These prompts challenge assumptions, pressure test ideas, and uncover blind spots so you get sharper insights.
❌ Most newsletters grow by trial and error.Â
These prompts gives you a clear, step-by-step system to figure out your positioning, grow your audience, and turn subscribers into revenue
"Working with Eva has helped me unlock the possibilities of AI in a way that directly impacts how I think about my business.
With her help, I was able to gain a level of clarity about my founder story and strategy that I hadn’t reached on my own.
If you’re looking for AI-driven consulting that helps you uncover deeper insights and real opportunities, I highly recommend ThinkWithAI."
Bartek, Co-founder at Kuula.co
Every conversation you have with these prompts pushes you to think deeper, act smarter, and move faster.
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