Daze of Code: Starting a new Software-as-a-Service

Regarding is my second software as a service company. My first, Instant Housecall (remote support software like Teamviewer), is still running, but the market has changed a lot and it’s time to try my hand at something new.

Instant Housecall has been running for 17 years so far. It is still reliably churning out revenue albeit at a slower pace than it used to. If you had told me when I started that Instant Housecall would be around 17 years, I wouldn’t have believed you. I thought at the time that software had a lifespan of about five years. I remember saying, “If Instant Housecall makes just $30,000 I’ll be happy.” Millions of dollars later, I’m still not.

Regarding is a completely different animal. It’s a Slack app, and I’ve never built a Slack app before. My experience this time around is completely different.

When I started Instant Housecall, I worked full time at a large telco in Toronto. I would plop down on the floor, sitting between my coffee table and my couch, at the end of each day, and bang out code on a laptop that had to be twisted for the sound card to work. That’s what I did with my vacation days, too.

With Regarding, I’m not doing any of the coding. I’ve hired a fantastic developer, Maciej, whose work is simply better than anything I could create. It’s also all on AWS, a platform that I have some knowledge about, but not enough to code a full-fledged app the way he has.

Developing it yourself vs. hiring a developer

I didn’t have the money when I started Instant Housecall to hire developers. I had to do it all myself. But that necessity was clouded by my own judgement too. I thought nobody could do it better than I could and quite frankly didn’t trust anyone to not steal my idea (remote support software at the time was innovative and there were few competitors). If I were starting from scratch again, which I guess I pretty much am now, I would hire someone. Here’s why:

·       It frees you up to think about other things. So much more goes into a software company than the code. In fact, the code itself is probably one of the smallest parts of any software company.

·       You have a more critical eye. You’re able to ask someone else to fix things that you might let go if it was your own work, because you’re just spending money, not effort, and that changes the dynamic significantly.

·       Coding is a young man’s game. I’m pushing 50, I have a kid, and I simply don’t have the concentration to go deep into code anymore. Could I do it? Yeah, probably, but I don’t want to.

·       You make compromises when you do it yourself. The number of things that I let go in the code for Instant Housecall that I said “if I ever get big enough for this to be a problem I’ll be happy” is ridiculous. That’s all technical debt, and some of it is still in there. I wouldn’t make those compromises if I asked someone else to do the work

And lastly, they’re not going to steal your idea. The people who work for you are there to work, not to steal ideas. It was an immature hallucination to think that they would, and I won’t make that same mistake again.

There are downsides to hiring a programmer, too. Setting the money part aside, you’re at the mercy of their schedule. For reasons that I’m not going to get into right now, Maciej works part time, on his own schedule. That leads to me sending him an awful lot of messages that say “What’s your availability like these days?”, which is probably annoying for him and frustrating for me. Never under-estimate the loss of momentum when you’re building a company. Momentum matters.

Venture Capital vs. Bootstrapping

I was approached more times than I can count by VCs for Instant Housecall. I never took the money. Instant Housecall might be a much bigger company today if I had. Teamviewer makes $158M/year. Could I be up there with them?

It also might not exist at all in which case I’d be losing out on the sweet nourishing passive income that it generates. I don’t know the ins and outs of venture capital but I’m a bootstrapper. It comes with precisely zero prestige and glamour to bootstrap, but it also means that you have zero obligations to anyone else. You can run your company the way you think it should be run, and I like that. I think bootstrapping is fun and I don’t mind risking my own money.

My sister-in-law’s sister’s husband (I don’t know what that makes him to me) is a Silicon Valley venture-capital backed businessman. I’ve seen his companies go from hundreds of people to zero in the blink of an eye. That world is exciting and fast paced, but I just don’t understand it well enough to go down that road. Would a VC even look at a Slack app? I have my doubts, but I haven’t even explored it. Money comes with obligations to other people and I prefer my freedom.


I’m not sure what this blog is going to turn into yet – or whether it will turn into anything at all – but those are some random thoughts for starting out