30 things I've learned from 30 years as a Python freelancer (opens in new tab)

While working on a PhD in technology and education, I thought that it might be worth creating a SaaS for people to teach whatever they want. This was back in early 2008, when such sites didn't exist. I assembled a team, and we made some progress, and even got a commitment from one funder. But I didn't really understand how to manage the team, and everyone was working very part-time on the project, and we didn't really have anything serious we could show, even after a few months. And the funder was only willing to invest if we found a second investor, which we didn't. So we ended up abandoning the project.

I think that we had some great ideas, including guiding instructors in the creation of online classes using the best proven pedagogical tools and theories. You could connect lessons to standards (if you were in a school, or wanted to be associated with one), or could do it free-form, or could use templates of various sorts.

I ended up finishing the PhD, so I can't complain too much! And as I wrote, I was probalby not a good person to run a startup; I'm much happier with my life as a bootstrapped freelancer. But it was hard to realize that I spent a year or so working on this with very little to show for it -- especially knowing that it might have thrived under a more experienced leader.