Small Business Software Dilemmas


So I run a small business. It’s not hugely profitable (yet), but it’s a nice side gig to my day job, which I thoroughly enjoy and could not possibly give up right now.


My goal is to grow my business gradually, building long-term relationships with non-profits and small businesses.

I believe the most important tools for a small business are, in no particular order, customer relationship management (CRM), accounting and invoicing, and project management.

Now for my dilemma. For the first few years of business, where I had a very small number of clients, and several one-project clients, I hopped around between Blinksale, Freshbooks and some others on their free limited accounts, trying them out. They all seemed to work pretty well, and eventually Freshbooks won me over with their frequent feature enhancements and their wonderful product team and support.


So when I reached the next level in my business, I imported everything to Freshbooks and went with their lowest paid plan, at $14 per month. Since then, I’ve had no complaints, and no issues whatsoever, except for that monthly email notifying me that my card has been charged $14.

I absolutely love the simplicity to administer my account, monitor payments, automate recurring invoices, etc. But I’m wondering if something on my local machine, like Billings, would be a better solution at a one-time fee of $39 (less than three months of my current plan). At the same time, the simplicity and time savings of using a great SaaS app like Freshbooks is nice.

I’m hoping a few small business owners and/or freelancers read this post and can provide me with some feedback on what they are using.

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Aaron is setup with Billings and Basecamp, which I’ve used sparingly. I’m not sure if they play nicely together, but it works for him. I’d love a fully integrated solution (or solutions) to manage my clients, both active and potential, billing, and project management.

Freshbooks and Basecamp play nicely together, as do several other SaaS tools. 37signals makes their case for web-based software. What do you use? What’s your experience? What’s your monthly bill for running your business? What other tips do you have for me?

2 thoughts on “Small Business Software Dilemmas

  1. The tools you mentioned for small businesses (and even freelancers) are very important. I have a few friends that use for their invoicing, appointment management and other things.

    1. Alicia – I took a quick look at SimplifyThis, but didn’t use it for any length of time. I’m amazed at how many tools are actually out there, independent and as part of a suite, for freelancers and the like. The big question is, is there more value in having it in the cloud, or in saving money and keeping it local on your machine?

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