Bookkeeping and Technology: Part 2: My Setup

This is the second post in my series about bookkeeping and technology. Last time I wrote about the early days of moving my business online. Today I'd like to talk about the tech I use and how it has changed the way I run my business. For the sake of brevity we'll stick to what I use for client bookkeeping.

My basic criteria:

If my client is going to be using it, I want the interface clean and simple. There should be as little industry jargon as possible.

Is this a slight on my clients? Of course not.

My job as a bookkeeper isn't just to record business data and generate reports. My job is to make that part of an owner's business as simple as possible. I want my client to worry as little as possible about entering data so they can get back to doing what they do best.


The majority of my clients work with 1 of 4 cloud-based apps: Freshbooks, Kashoo, Xero, and Wave. Freshbooks is, by far, the most popular, but it's not a full solution. It does time tracking and invoicing better than anything else, but in order to get a full set of books I have 2 choices. I either sync the Freshbooks data with another cloud-based app or download the data offline and import it into QuickBooks. My Canadian clients tend to use Kashoo, and my US clients use Xero. For clients who want a low cost, all-in-one solution we usually choose Wave. Wave feels like a beefed up Mint, because it will also track personal finances. It's free for the core set of features so that helps with solo operations just getting started.

Having these services has completely changed the way I work. I used to drive over to someone's office, pick up a box of paper, and then go through each page, entering data manually and reconciling the bank accounts from paper statements. Now the apps download the bank transactions every morning, I see new receipts show up in shared folders, and some of the apps do the bank recs for you. Although I still get nostalgic for the old ways, having a lot of these steps taken care of digitally means I can spend more time analyzing the data and talking with the client. I'll take that over paper cuts and carbon stains any day.

File management

10 years ago it would have been hard to tell if I was working or dropping of my recycling. My car was constantly packed with envelopes, boxes, or just loose stacks of paper. When I started working from home, my version of Dropbox was my actual mailbox. We don't get mail delivered directly to the house, so I'm sure people constantly dropping off packages in my mailbox throughout the day (combined with me not leaving for work anymore) had my neighbours thinking I had opted for a different line of work.

Two things drastically changed the way I interact with documents.

  1. Software started importing bank transactions automatically.
  2. File sharing software like Dropbox. One of the first things I do when working with a new client is to setup a shared folder in Dropbox. I also use Google Drive with some clients. They both have great features and with prices so low there's no reason you can't use both.


My social skills fall with an awkward thud between little and no. I'm pretty sure I'd pick dental work over a phone call with a stranger 99% of the time. I'm not proud of it, but it's a fact none the less.

Moving my business online has been a blessing. It was hard for me to work with new clients in the past. Having my first impression be an awkward phone call didn't do me any favours.

Now email is my best friend. I actually have clients who I've never spoken to, and probably wouldn't recognize if I ran into them. That's not the norm, but it's crazy to think what kind of work gets done every day without any face to face or even voice to voice interactions.

I use GMail's web interface. I've learned all the keyboard shortcuts so I can fly through an inbox at an alarming rate. I saved the "special email addresses" that services like Evernote, Omnifocus, and Asana give you so I can quickly send emails elsewhere for further processing or archiving.

Skype isn't great but it's good enough to get the point across, and the file sharing, instant messaging and screen sharing sure make it a lot better than a traditional phone call.

For team chat I've used HipChat. From what I've seen it works well.


For me the big win here is mobile banking. I've had more than my fair share of panicked messages about last minute transfers or bill payments. Instead of a long drive to the bank or running back to my office I can move money or pay that bill from a folding chair at a lake.

Thought Technology

Let me steal a term from Merlin Mann and John Roderick. The biggest change to my business in the past 5 years is the elimination of 9-5. Sometimes there are client emergencies, but these are rare. For the rest of the time, work just needs to get done by a certain date. Payroll is on Friday, that vendor bill is due on the 10th, etc. I could work a 3 day or 7 day long as the work gets done on time. The downside is that I can very easily set bad expectations for myself with my clients. If I reply to that 11:00pm email they'll expect it every time, so be aware of those kinds of things when you're getting started.

Cloud-based software, file sharing, and Skype have all changed the way I do my business, but there's a bigger story to discuss. Have all of these changes made life better or work easier? In the last post in this series I would like to talk about technology from a different perspective.

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