Bookkeeping and Technology - Part 1: My Origin Story

Someone emailed me the other day with (what I thought was) a simple question. To paraphrase, they wanted to know how technology has changed the way I do my business. That's a no-brainer, right? I'm a guy who loves to geek out over the latest and greatest gadgets. I'm constantly testing out new things, and my business has been completely transformed over the past decade with the help of technology.

Turns out it's not that simple. I really spent some time thinking about the topic. I mean really thinking about how it has affected the way I work, how it got me to where I am today, and how my business would run in an ideal world. I tried to write all of my thoughts into one post. It was too long and disjointed. This is going to be a series of least 3 posts.

Today I want to talk about how I made the initial switch from local clients running desktop software to a more cloud-focussed bookkeeping business with remote clients all across North America. The next post I'd like to highlight the software and tech I use to run my business, and how that's changed over the years. Finally, I want to paint a picture of how my business (and life) would look in an ideal world. Stay tuned for that one, because I think my answers might surprise you.

I'm sure by now I have dragged out my origin story more often than Marvel Comics so I'll try to be brief. Up until 2009 I was managing a local business (with a few smaller bookkeeping clients on the side), using desktop software, and spending my 9-5 in an office outside of the home. By January of 2010, after a few major changes (most of them bad ones) I found myself sitting at home with no office, no business to manage, and way fewer clients than I needed to keep food on the table.

I needed to work from home, and needed new clients fast, so I just started researching like a madman. I had 2 main problems to solve.

  1. Find new clients (I'm from a small enough city I knew they might not be local)
  2. Find software that would let me work with these new clients remotely

Finding new clients

20 years ago I would have placed an ad in the newspaper. As a solo operation it's the only thing I could have afforded, while still reaching a good percentage of my target market. If that didn't work, I would have asked friends and family to spread the word.

Instead, I joined Twitter, LinkedIn, Facebook, and a few other smaller sites. I jumped onto discussions on the QuickBooks forums, and started looking for blogs about bookkeeping. I started this site, and started posting random bits of info I came across. I did no traditional advertising of any kind. The closest thing I tried was a short run of Facebook ads. They were a bust. Every other spare minute I had was spent devouring audiobooks and podcasts that talked about business and technology.

All of this effort did very little to get me more clients, but I learned a ton about running a business online. It was essentially my 3 month long version of an MBA. Ironically, it was when I started to research the second problem that I found new clients.

Finding new software

QuickBooks was my software of choice back then. The online version wasn't an option yet(at least here in Canada) so I had to start researching other choices.

The first one that caught my interest was FreshBooks. It was really earth-changing for me. I had always used these huge software suites like QuickBooks and Office that tried to be everything for everyone. They were incredibly powerful, but user-hostile to anyone without an accounting degree. Then, here's this time-tracking and invoicing app based entirely online. It didn't try to pretend it could do it all. It did a few things really well and then offered incredible customer service and support. I started using it right away. It wasn't going to replace QuickBooks but I needed something simple to track my time and invoice my clients.

After that I did a few posts about FreshBooks and someone at the company took notice. They tweeted about my posts which got me some attention, and later they asked me to write a few guest posts for their site. To this day, over 5 years later, the FreshBooks blog is still my biggest source of referral clients and 2nd biggest source for blog traffic (next to Google of course).

I learned a lot from this experience. The main lesson changed the way I approached my work. Bookkeepers and accountants usually pick their favourite software and then expect their clients to work around that choice. FreshBooks made me realize that the software was there to make my clients lives easier. So, from that point on I switched my focus. I researched new software and services with their needs in mind.

Could someone who just opened their first business use this software without wanting to tear out their hair?
Could we both access the data 24/7?
Could I take that data and, with or without the help of another app, generate the kind of reports they and their accountants wanted?

These are some of the questions I ask myself when I try out new software or test out a new workflow. These questions have served me well, and I think they've made me a better bookkeeper.

In the next post I'll talk a little more about the types of technology I use, and how they have helped me run my business and serve my clients.