Like @clechasseur, throwing things out to see what sticks. Clearly, we don’t want to irritate or plead folx to distraction. We might also be able to implement these in different places, like certain pitches on certain social media sites or in emal vs “pleas” here on the exercism platform.
This first category is what I call the “we interrupt this program” plea. Specific messaging that pops up after someone has engaged at a certain level with content on a track. Thinking things like earning certain badges (Lackadaisical, Conceptual, All your base, supermentor), earning certain track trophies, reading approaches, completing a certain number of mentoring sessions, completing certain # of exercises, completing an existing syllabus, and completing a track. Zeroed out if the user has a recurring donation in place or a donation of any amount in the last 6-12 months:
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Enjoying this track?
Maintaining a track on exercism costs &____ a month/year in infrastructure and staff costs. If you can, please consider donating to support this tracks expenses.
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Was working through this syllabus helpful for you?
Even though exercism is largely built by awesome volunteers, it still costs $____ in infrastructure and staff to develop and maintain a syllabus like this. If you can, please consider donating to support this syllabus, or the addition of a syllabus on another track.
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Missing xxxx language?
We’d love to hear about it! Tracks take aprox ____ hours of volunteer work and $___ in infrastructure and staff time to get them to launch. If you can, please consider donating in support of adding your favorite programming language as an exercism track.
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Did this content section help you deepen you understanding of ____ ?
This content takes aprox xxx hours of volunteer time and $xxxx in infrastructure and staff costs. If you can, please consider donating so that we can add more content sections like this one. (this can go for approaches, concepts, track videos, performance articles, hints, etc.)
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Enjoying this exercise? (this would need to be very sparingly used)
Even though exercism is largely built by awesome volunteers, it still costs approx. $xxxxx in infrastructure and staff costs to develop and add a new exercise like this one. If you can, please consider donating to fund the development of more exercises.
These could maybe also be periodically put in email messages, or in update emails. These ideas could possibly also be incorporated into a shared post for LinkedIn or another site where you surface the ongoing and development costs and talk about why it’s worth the time and money because providing this for free helps so many people.
This next set is what I call the Jimmy Wales pitch. Annual/6 month/quarterly drive for funding sort of thing:
- “Last month (or other interval), xxxx number of students signed up for exercism and completed
Hello World. If half of them donated 3 dollars or more, we could fund our project for xxxxx months. If 25% of them donated 3 a month, we could keep the lights on for xxxxx months. If you can, would you consider a one time or recurring donation?”
- “xxxx number of students use our site to complete one or more programming problems a month. If each of them donated $3 or more, we could fund exercism for xxxx months. If you can, please consider donating.”
Pitching in terms of what access or benefit you can buy for others:
- If you can, please consider donating. As little as xxxx dollars a month can fund the infrastructure costs for xxxx students. Help keep exercism free to all who want to participate.
- If you can, please consider donating. A monthly recurring donation of xxx can support mentoring infrastructure for xxx students. Help keep mentoring free and accessible.
- if you can, please consider donating. A monthly recurring donation of as little as xxx can support adding x number of new exercise approaches documents to help xx of students.
Videos that talk about current “keep the lights on” expenses vs what it takes to add the next killer feature. Publish these the way you do 12in23 videos – every x months or so, make a video about what things you want to add, and how much money is needed to do that. Ask if anyone can give what they can in support of adding the new features. Each video could re-iterate what exercism has done so far, what exciting things happened in the last two months, and what you could do “if only we could increase our donations by xxx in the next interval.”
“Why I give to exercism” videos that features short comments from people on why they gave money, and how good it feels to support other students in their learning. These could periodically feature on the home page, and be shared around social media.
“Price-pointing” - putting a price on what it takes to do x, in terms of infra cost, staff cost, and volunteer time. Use these to periodically pitch donations that don’t fall into the “I can give 9.99 a month category”. These are pulled out of my arse, so we’d have to do more serious number crunching, but these might be worth it across various places on the site and elsewhere.
- $5 dollars as the cost of adding a new practice exercise to a single track.
- $3 to support mentoring infrastructure for xxx students on a track
- $50 dollars in staff and infrastructure to create a track introduction video.
- $5 dollars to create an exercise approach or performance article for a single track.
- $xx dollars a month to support a given track’s test runner/representer/analyzer … and so on.
- $100 dollars in staff time and infrastructure to add a new language track & get it to launch, not including volunteer time.
- $5 dollars as the cost of adding a new approach (“dig deeper”) document or performance article for a single track.
- $5 dollars to add a concept write-up or concept exercise.
- xxxx dollars to develop and launch a new syllabus.
Can’t think of more right now … but the point would be to encourage one-of donators to think in terms of “covering” some of their (or someone else’s) use of the site without committing to recurring donations, or large recurring donations.
Badges for donating that could be added to social media profiles. “Proud donator to exercism.” “I support free education for programmers.” with a link back to a site page that has videos/quotes/impact statements, etc.
Ok. Will add/adjust later as I think about this more. 
The team might be interested in asking those who subscribe what ‘Job to be Done’ (if you are interested in that product framework) they ‘hire’ an Exercism subscription for… 