Checkbook“It’s hard to lead a cavalry charge if you think you look funny on a horse.” — Adlai Stevenson

In 1999, I arrived in California and went to work for an Idealab company called PayMyBills.com. It was the heyday of the Internet start-up and I remember thinking my first week that I had picked a winner. PayMyBills was going to revolutionize the way consumers received and paid bills online while making me the next dotcom millionaire. The experience didn’t really turn out as planned.

As an employee, I felt obligated to use the service and immediately signed up as a customer. It differed from online bill pay in that your paper bills were redirected to our operations center where they were manually opened, then scanned and served online where the consumer electronically paid it. This, of course, was long before companies offered ebills and the idea was to eliminate all the paper from the process.

It sounded like a great idea, until our customer base started to grow and quality control didn’t quite keep up with the volume. Anyway, for some reason they missed a cable bill and I remember being dinged with a late charge and threat of service interruption. The entire experience freaked me out and required several phone calls to sort out. Shortly after, we were acquired and they handed out the pink slips. I canceled my service and the bills were redirected to my home address.

And they have been coming to my mailbox the last several years. Over time, you would think that I might regain confidence in the electronic payment system but for some reason I had an aversion to it. Instead, I have continued writing checks, addressing envelopes and buying stamps for my monthly bill paying ritual. Until now!

One of my goals for 2006 was to start paying bills online. Just writing the checks for all the mortgages on the rental properties was a 30-minute Sunday task that I could quickly reduce to 3 minutes if I would just automate. Plus, when the postal rate when to 39 cents… it seemed like 40 cents and the way my mind works, I starting rounding up to 50 cents. I just couldn’t spend a buck to send two payments through the mail.

So it’s official. I’m using free bill pay at my bank. Next step is to go all the way and select the ebill option. Baby steps though… first things first.