In the interview, you said that you had 10 paying customers before you even started coding or had a company. My question is:
How did you get those people paying you, and how much they paid? Since you have a monthly service, surely they haven't been paying your usual monthly fee for all that time while you were coding?
I reached out to some friends of mine, pitching them something like "I'm developing a system to help you achieve your goals. It's based on daily planning and reflection. Paypal me $10 for the first month if you're interested." The actual conversations were much longer than that, in which I explained a bunch of the high-level thinking behind it, mentioned that I was looking for some beta testers, etc. I probably also mentioned that I'd trialed the basic system myself and informally with another person.
One of the nice things about offering "I'll help you achieve your goals" is that pretty much anyone wants it if you can actually do it. The latter part is of course hard. But yeah, because of this I probably asked only 15-20 friends and got 10 to pay based on that. It also helps that I have friends who are willing to experiment and who trust me not to just run off with their money.
Part of what also helped, I'm sure, is that I reached out to people I knew individually and they got to have the sense of being part of this early group of testers.
I followed the "do things that don't scale" approach. At the start, I didn't have custom software, but I queued up emails manually using Boomerang, to bug people each day at the time they specified, to plan their day and reflect. They replied, and I put their data into a spreadsheet and elsewhere. I spent about an hour per week for each of those users at the start. I was giving them value manually/personally, rather than with software.
Hmm. I think my biggest milestone came when someone signed up for the free trial, didn't respond at all to the personal "how is the trial going?" message... didn't respond to my "btw, your trial is ending in a couple days... any questions?" message...
...and then their trial ended and they paid.
Even though I'd written a full software system at that point, the app was still fairly hands-on, and it wasn't until then that it was fully obvious that someone would pay for just the software. In retrospect this is a pretty big thing that it would have made sense to test much earlier somehow.
I'm pretty optimistic by nature, and Complice has felt promising since the beginning. I think it probably helped that while I had a vision/goal (= become ramen-profitable by graduation) I didn't spend too much time fretting about it. I just focused on making incremental improvements to the system (eg UX).
And this in many ways is the philosophy of Complice itself: stay oriented towards the big picture, but focus on what you can do today.
How did you get those people paying you, and how much they paid? Since you have a monthly service, surely they haven't been paying your usual monthly fee for all that time while you were coding?