I tried to reply a couple of days ago but it was flagged needing approval from an admin. I think it was because it was a short message with a URL in it, so I’ll try to format it here instead 
The complete doc that I wrote is here: ANSI Commission - Design Thoughts | Tom McKeesick , It contains all the example images that I couldn’t link here
ANSI Commission - Design Thoughts
Thanks for getting back to me! I’m excited to collaborate as I’m a fan of your work.
Legal/Licensing/Other
1. License
pokesay is licensed under the BSD-3-Clause license, which allows the code to be used in both open-source and proprietary software, provided that the original copyright notice and license terms are included
I’m happy to add a separate license for the artwork that does not allow it to be reused in this manner, if you’d like? Let me know your thoughts.
2. Monetization
pokesay is free, and will remain free forever. It’s a passion project for me, and I don’t intend to monetize it in any way, so I wouldn’t be making any money off of your artwork.
3. Attribution
I’m happy to include your artist name/signature in all artworks that you provide, as well as in the README and documentation for the project.
4. Distribution
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pokesay is distributed via GitHub, aur (arch linux) and homebrew (macOS). These binaries/release files would include your artwork.
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The artwork would also be viewable on the GitHub README page.
Please let me know if you have any concerns or thoughts about this.
Technical considerations
The pokesay binary runs on Linux, macOS, Windows and Android (via Termux). Predominantly, it’s used in linux terminal environments. It uses ASCII and UTF-8 chars with ANSI escape codes to display the pokemon sprites in the terminal, as well as borders for the speech bubbles and info box.
Ideally, the artwork would need to be in UTF-8 format if possible? I know that many ANSI artists use the CP437 character set which isn’t compatible, is it an issue to create the art in UTF-8 instead? It’s not a deal-breaker if so, I can convert it to UTF-8 using durdraw, but sometimes the conversion isn’t perfect so would prefer to have the artwork in UTF-8 if possible.
Design thoughts
1. The title
I’d love some text that says “pokesay”
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it can either upper or lower case, whichever you think looks best
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it would be displayed by the pokesay program in the terminal when a special arg is provided (e.g. pokesay --title or pokesay --demo)
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I’d also display a screenshot of this at the top of the GitHub README page, replacing the current one that I just made with figlet
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I like many of the colourful designs that you do. In terms of the palette/font to use, I’d rather avoid any potential legal issues with Nintendo, so
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some yellow and blue is fine, as it would match the original pokemon colours.
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but it shouldn’t be only yellow and blue, and using yellow/blue is not required at all, only if you feel like doing so
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The font should be different to the original pokemon font
Examples
(see linked doc for examples)
The examples are in the linked document^^, I can only upload 2 photos and 2 links to these posts and the formatting is a bit finnicky to deal with
2. The help doc
I have both a manpage and --help output for the program that lists all of the available args and options. This art would be displayed when the user runs pokesay --help. It currently looks like this:
I’d like the title to be non-coloured
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I’d also like it to be different from the font used in the title art above
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I like a lot of the titles that you do that are in the style of the ‘SK!MF.TXT’ example below
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Some colour in the help section underneath would be nice, like the SK!MENU.ANS example below
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Some titles separating the different doc sections would be good, like in the SK!MF.TXT example below
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The --help docs currently only show the command-line arguments. I’d like to add more sections to it from the manpage like “Examples”
TL;DR, something like the title from SK!MF.TXT for the top, some section titles from that same file, and some colourful CLI arg descriptions from SK!MENU.ANS in the top section.
(see linked doc for examples)
Notes/Other