It's time to kill my darling—tell me about ideas that you've given up on and how you came to the decision

What are some projects that you've "killed"?

Here's mine, that I'm officially pulling the plug on today:

I had read the 7-day startup when I had the idea for what would later be Enrollem. I think it was in 2015.

I was taking improv classes in San Francisco and all of the improv companies websites were using some cobbled together variant of PayPal Checkout button together with Google Sheets and some stressed out admin person to stitch it all together. They were doing things that didn't scale, which is amazing and required in the beginning. And when success came, their admin tasks grew together with them.

I wanted to make things better for those people. I wanted to build something that could make things "Gumroad simple" for people who ran workshops or classes. I started finding and talking to prospective customers in the fall of 2017.

Fast forward to today and I've built a few prototypes, talked to a whole bunch of people who do this kind of work, had them use the prototypes, gotten great feedback and learned a lot. So I'm coming close to starting to build the next prototype together with a few theaters. It's going to pretty closely resemble an applicant tracking system (ATS), like the ones you'd use for tracking job applicants, but where it'd handle fees/tuition/dues/whatchawannacallit.

I've even done consulting and built up a little runway in order to focus on Enrollem for at least a few months.

It's when I start looking into how to handle the payments for the theater I'm collaborating with I finally hit the wall that made me decide to give up on this idea.

Tax regulation. I'm in the EU and they're in the EU.

If this is going to scale... someone (me?) needs to consider taxes in all the countries I want to offer the service in. For me it's pretty simple—use Paddle or FastSpring and offload the headache to them. But... for my intended customers...

a. Either I handle their tax stuff, or...
b. I let my customers handle taxes (maybe through a third party, like Quaderno)

If I go with (a) I'll be building what closely resembles an accounting business, which is not the type of business I want to build.

If I go with (b) I'm not going to provide the turnkey "Gumroad style" simplicity that I wanted to give and that all the people I've spoken to were hoping for.

So I'm going with (c): I'm sunsetting Enrollem. It's a bit sad—but now I understand that this isn't a business I'm meant to build.