Project: Maestro - Substack Newsletter - Wordmark
Using AI to design and develop a consumer application
I needed a title or banner image which Substack calls a “Wordmark”. The models struggled with this concept on a few levels. I used the following request prompt:
Give me ideas for a wordmark for a Substack newsletter called
"Project Maestro" about using AI to design and develop a
consumer application.
NOTE: I had to abandon the prompt above and used the following:
Describe the design aesthetics of a stylized image version of
newsletter title "Project Maestro". The topic of the newsletter
is using AI to design and develop a consumer application.
Strategy
Stack multiple AI technologies in three phases:
- Theme Creation - Brainstorm themes using large language models
- Prompt Optimization - Use LLM to build efficient text-to-image prompts
- Image Generation - Create images using generative models
Theme Creation
Models really struggled when I started including words or titles. They also did not understand that I wanted a banner style image with the newsletter title. This required a moderate amount of prompt experimentation to get desired result
Where did they succeed?
- Good suggestions on font and
- Color pallete aligned with logo
- Provided different conceptual themes
Where did they fail?
- Did NOT understand the term “Wordmark”
- Had to experiment with prompt phrases to get desired output
AI Tool Report Card

Notes
- ChatGPT (A) - Provided font and style options
- CoPilot (A) - Provided font and style options
- Claude.Ai (A) - Provided font and style options
- Bard (C+) - Provided multiple concepts for newsletter names
- Grok (C) - Fluff and not much substance
Prompt Optimization
Prompt outputs were regurgitated from my input prompt. No real improvement other than abbreviating the commands. Co-Pilot auto-generated images, which was nice.
AI Tool Report Card

Notes
- CoPilot (A+) - Generated 4 usable options
- Claude.Ai (C) - Abbreviated my original prompt (no improvement)
- ChatGPT (C) - Abbreviated my original prompt (no improvement)
- Bard (C) - Abbreviated my original prompt (no improvement)
- Grok (F) - Regurgitated my request
Image Generation
Images were square, busy and unusable. Created the banner directly in Microsoft Designer where had more control over image.
Where did they succeed?
- Designer’s image suggestions were useful
- Text generation was better than Dalle-E
- Using AI to modify images is MUCH more effective than prior tools
- Background removal, palette shifts, color replacement

Microsoft Designer’s cropped banner generated with CoPilot
Where did they fail?
- Pure prompts generate images were sub-par
- Requires a lot of iterations and prompt tweaking to generate anything remotely usable
- Hallucinations are a problem and lead to design drift
- Dalle-E REALLY struggles with text

Dall-E, seriously considering changing the name to project meisto

Stable Diffusion went the demotivational poster route.
AI Tool Report Card

Notes
- Microsoft Designer (A) - Winning image, had to crop image to 21:4 aspect ratio
- CoPilot (B-) - Aspect ratio wrong, required edits
- Dalle-E (C) - Unusable images, text misspelled
- Stable Diffusion (F) - Weird shapes and colors (was that a bowl of lettuce?)