When I first quit my job and decided to venture out on my own, I was working alone, had almost no resources, had very few connections, and almost no web experience. What I did have was time. And the desire to learn anything and everything that could help me be successful.* So, naturally, if there was something that needed to be done I picked up a book and learned it. This is a great thing. It’s probably a necessary trait to bootstrap your own company, especially if it’s your first company and you’re in a situation like I was.
Thankfully over time we’ve grown and now I don’t have to go at everything alone. First I had partners. Then we teamed up with a lawyer and an accountant. And then we started hiring employees. We have more money, more connections, and more experience. All also great things.
However, I haven’t really lost the mentality of “solving by learning”. Most of the time this is still a good thing. If I don’t know a specific programming technique, if I don’t know how to use a specific piece of software, if I don’t know enough about a service that could help grow our business, I’m more than happy to spend a weekend reading up on it until I know what I need to know to get the job done.
Other times though, I’ll foolishly dive in to something that isn’t my expertise, doesn’t need to be, and can be accomplished better by me not learning it. Either there’s someone else who can do it better – one of my partners or our employees – or there’s an existing service out there that solves the problem. This is odd to say, but it’s been a challenge to learn what to learn and what not to learn (that’s a tongue twister!). When you’re naturally used to learning and doing everything, delegating and outsourcing take some getting used to, as does determining exactly what to continue to do and learn vs what to outsource and delegate.
In the past we never would have been able to afford Google Apps for Business, Backupify, RescueTime, ProXPN, Pandora, or any of the many other services that we now happily pay for because they solve a business problem. In the past I probably would have spent considerable amounts of time attempting to solve the same problems for free. Worthwhile then for sure, not worthwhile now.
Another great recent example is our hosting provider LiquidWeb. We switched over to them in a matter of days during the great server disaster of 2008. I think that those few days took a few years off of my life. Just re-reading those posts stresses me out! After the dust settled, my initial instinct was to take control of everything involved with managing our servers. While not my expertise, I decided that I needed to learn how to be an expert systems administrator.
And so I started spending some nights and weekends learning. It only was natural. Except during that time something awesome happened. I had to start several tickets with the LiquidWeb “heroic support” and I came to notice a few patterns. Each email was responded to within minutes by a sysadmin who actually knew what he/she was doing! They were always happy to go above and beyond to solve the problem quickly. If I needed to call, a sysadmin always answered and could help me right away.
Over the years I’ve spent less and less time doing any of the sysadmin tasks that I do know how to do. For instance, I can install a SSL certificate. It’s not hard. But it does take me a few hours. Instead, I can just shoot them an email that says “I’d like a SSL on domain X at IP address Y and you can bill it to my account” and it’s done within a few hours. They have a team of experts willing to help any time we need it. Their service goes beyond anything I’ve ever experienced. Even though we pay them quite a bit of money for our two servers, I never expected to essentially have my own team of sysadmins available to me 24/7/365.
More recently, their migration team handled the transition of Detailed Image over to a new server. Moving DI (or any e-commerce site) is more complex than the average site because we needed to preserve our IP address, SSL, and be PCI compliant. There were a few minor minor hiccups, but overall they did a much better job than I ever could have and they did it in a matter of days from start to finish (the actual migration only took a few hours). There was frequent, clear, communication between myself and the engineer doing the work. It was like he was a member of our team.
Because of past server disasters, because of how critical having the site online is to our business, and because I naturally want to do anything that’s important myself, this was something that was hard to give up control on. But it also caused me to reflect on when it’s intelligent to do something myself and when it isn’t. We’re at the point where not ceding control to a migrations expert who does this every day for a living would be crazy.
…Plus I had backups upon backups in case anything went wrong, that also helped ease my nerves 🙂
*Fresh out of college, I also had the oft-assumed ability to learn quickly, a skill that I believe diminishes over time if you don’t continuously learn. One of the many reasons I think the best time in your life to start a company is when you’re in college (that link goes back to my third post ever, from 11/25/2005)