Bootstrapping a Side Business - First Steps

For the past few weeks I've been working on a little product that I'm calling remindlyo, which I'm hoping to turn into a secondary income stream. The basic idea is that you put events about the important people in your life, like birthdays, anniversaries, or what have you, into remindlyo. On the day of the event, remindlyo calls you to remind you and connects you to them, all on the same phone call. You can read more about it on the main remindlyo site. In this post I want to talk more about the why instead of the what.

Since I first figured out what a business does, I've wanted to get in on it. I think I was 12 when I first said to my mom "I want to start a business. I don't want a regular job." Of course, like any responsible mother, she replied "How about you go to college and get a few years experience before starting?" Not exactly satisfactory, but it was sound advice. Now, 15 years later, I'm in a position where I can actually follow through.

I've been aware of Patrick McKenzie for a few years now, but I recently came across his Greatest Hits list and over the course of maybe two days I devoured every single post. They're all great. I had already had an idea for a little project like remindlyo, but Patrick's posts inspired me to expand it into something that I could actually sell.

So then the problem was, what to sell? What can I build that people will buy? I've had a few ideas in the past, but then a few weeks ago my girlfriend kind of dropped the idea for remindlyo in my lap one day. When I told another developer at Emma about it he suggested a whole suite of improvements, which pretty much leads directly to the marketing site I have up and running today.

I can hear you asking "but what if people don't buy it?". That's the biggest fear, but also the most irrelevant, at least for me. I'm doing this first and foremost to learn how a business works from the inside. A very close second is the chance a bunch of technologies that I haven't played with until now, including Ruby on Rails, Twilio, and Heroku, as well as how web marketing and the good kind of SEO works. The opportunity to gain an additional income stream is a somewhat distant third.