What if I started a nonprofit?

Almost a year ago I articulated my career interests in We need better tools for online speech. One benefit of that is it's easier to imagine myself taking different career paths. The goal isn't "create a successful startup," it's "design, develop and promote tools for online speech," and creating a startup may or may not be the most effective way to do that.

In that vein, I've occasionally wondered: since I'm more interested in public goods than private profits anyway, should I structure my work as a nonprofit instead of as entrepreneurship? What would that even look like?

I see three main areas of work: 

1. Theory. Develop a "roadmap for the Internet." What would an ideal Internet look like? What's the shortest, most practical path to get there—or at least, to get closer to there—from where we are now?
2. Development. Create software that addresses the next steps in the roadmap.
3. Marketing. Promote the ideas in the roadmap and relevant software projects; whether they're made in-house or by another organization.

This is all stuff I'm currently doing. I have my unbundling social media theory, I'm developing Yakread, and occasionally I even do some marketing. Business growth has so far been elusive. I'm in the middle of overhauling Yakread's user experience, particularly for new users, which I estimate will take 2 - 3 weeks. After that I'll go back into marketing mode, and I give it about a 15% chance that I'll be able to justify continuing to work full-time on Yakread. More likely, I'll go back to being a software engineer somewhere and take more of a slow-and-steady, part-time approach with my tools-for-online-speech efforts.

And thus we come to the big question: if I start doing Yakread etc part-time, should I keep doing what I'm doing now, just with less frequency, and aim to eventually go back to full-time work once Yakread's had time to grow enough? Or should I take a fundamentally different approach... like starting a nonprofit?

I see the nonprofit strategy going down something like this:

• I'd shift my non-day-job time away from coding and marketing and more towards something that looks a bit like independent research. I'd spend a lot more time reading other people's ideas in the how-to-make-the-internet-better space, and I'd try to develop my own ideas more rigorously and completely. I'd try to become part of the public discussion.
• I'd take Yakread open-source. Instead of developing it by myself, I'd try to turn it into a community-driven project. I'd have very little time for coding myself, but I could provide direction, code reviews, and assistance in general.
• I'd try to drive adoption—both for my ideas, and for Yakread—by writing. To some extent, my research would produce essays and such naturally. But on top of that, I'll need to figure out who exactly I'm trying to reach (end users? software developers who might become Yakread contributors? potential donors? some other group?) and tailor the message to them. And then I'd have to figure out how to actually reach those people.

The org would be funded by profits from Yakread (and any other projects I/the organization creates) and donations. I could probably get "stakeholder support" for seeding the org with, say, $1,500/month from my own salary. Perhaps I could use that to get some help with writing and marketing. Long-term the goal would be for the org to be self-sustaining, like Ghost, with donations (both in terms of money and developer time) acting only as an accelerant.

In addition to Ghost, some of my inspiration for this comes from the Signal Foundation, The Roots of Progress, the Initiative for Digital Public Infrastructure, and my personal disappointment with what VC-funded businesses have produced so far.

What happens next. Fortunately it's not like I have a big button in front of me labeled "start a nonprofit" that I have to decide whether or not to press in the next five minutes. Open-sourcing Yakread would be a somewhat drastic step, but it doesn't need to be the first step. I guess the two questions I have are, "if I get a job, ...":

1. ... on what should I primarily spend any remaining time I have? Independent research? Marketing Yakread? My existing open-source work and the community around it?
2. ... what would be the best way to spend $1.5k/month on the furtherance of tools for online speech? Is there something better than simply "save up to buy a house and pay it off ASAP?"

For #1, I think... if Yakread's metrics are promising enough (even if they aren't promising enough for full-time work), then stick with that. If not, put all my extra time into Biff (my aforementioned open-source work), since that project already has a little momentum. Independent research I think should be saved until I'm able to work on tools for online speech full-time sustainably. Further choices can be made later. e.g. if Yakread goes well then I can continue with entrepreneurship; whereas if Biff takes off then maybe turning Yakread open-source and moving it under that umbrella (Yakread is made with Biff) would be best.

For #2, 🤷‍♂️. Maybe best to focus on getting myself into full-time TFOS work permanently first.

This whole post might be a little anticlimactic since it's feeling like the appropriate answer to "should I start a nonprofit" is "not anytime soon." That's fine! My thoughts for a long time have been that I should just get a business of some sort—whether that's Yakread or something else—off the ground first, and then worry about nonprofit schemes later.

And yet, this nonprofit idea keeps bouncing around in my head. I guess I wanted to write it down just in case there's anyone out there with whom this resonates. If that's you, shoot me an email! Maybe we can collaborate somehow.