I have always liked having a personal finance application to help manage bank accounts and expenses. I forget the first one I used but it was DOS-based back in the 1980s. I think I switched to Quicken at some point, and I know I used Quicken 2000 for over fifteen years on a Windows 2000 machine.
A few years ago, due to my open source bent and that fact that I didn’t want to keep a Windows machine around to run Quicken, I started using GnuCash. GnuCash is a “serious” financial application in that it adheres to double-entry accounting principles. The biggest complaint people have about the application is that it takes a lot of effort to get started. I have only taken a single accounting class in my life, but I knew enough to feel comfortable with GnuCash. If you have seen the equation:
Assets = Liabilities + Owner's Equity
or heard the term “debit left, credit right” then you know enough to use it.
But the one thing I can’t do with GnuCash is make it easily available to more than one person. I do share financials with my spouse, so over the holidays I decided I would start 2025 with a new accounting system. After looking around I bought a discounted year of Intuit’s Quicken Simplifi.
That was a waste of time and money.
Now to be fair, I am not the target customer of Simplifi. The idea is that you tie in all of your accounts to the application using APIs to your banks, and it is supposed to help you budget and manage your money. Because the data streams are separate, it doesn’t do double-entry bookkeeping. For instance, it will connect to your credit card account to download those transactions, and then it will connect to your checking account to download those transactions. It should then, magically, match a credit card payment from checking with the corresponding entry in the credit card account.
The thing is, I’m not going to give Quicken direct access to my accounts. Any application that has a nearly hidden “opt out” to “don’t sell my information” shouldn’t be trusted with that kind of access.
Most of our expenses are charged to an American Airlines credit card so that we can earn travel points, so I did connect that account, and it was nice to just have to verify each entry instead of adding it manually (note that it is possible to import this information in GnuCash, just not automatically).
My first real hurdle with Simplifi came with managing an investment account. I am a huge believer in Health Savings Accounts (HSAs). In the United States this allows you to set aside money for health expenses tax-free. In fact it is triple tax-free: the money you put in to it is not taxed, it isn’t taxed when you remove it and gains are not taxed.
The way I account for it is when I get paid I put my HSA deduction into a holding account, and then when those funds are invested (usually a few days later), I move that money into the investment account as a purchase of mutual funds.
This works flawlessly with GnuCash with one entry.
In Quicken I have to move the cash into the investment account (first entry), then use the cash to purchase the mutual fund shares (second entry) and then I have to manually update the holding to show that I actually purchased shares (third entry).
This was when I had my first exposure to the “help” system, in which I chatted online with a “coach” who told me that, yes, this is what I had to do, as I was certain there had to be an easier way. There wasn’t.
You also can’t “reconcile” accounts with, say, a bank statement. The model is that you are supposed to link all of your information into the app so there should be no need to do this, but since most of my accounts are manually entered it was a pain to have to match entries up without the aid of a reconcile screen, such as exists in GnuCash.
Despite this, I was willing to stay with Simplifi, until yesterday. I went in to do an update an noticed that my checking account was reporting way more money than was in the account. Note that I’ve only been using the system for about seven weeks so there were only ten or so entries in the account and it was easy to see they didn’t add up to the reported balance.
The problem seemed to be around a credit card payment entry so I tried deleting and re-adding it and that just made the problem worse. Just to make sure there were no “hidden” transactions, I even exported the entries via CVS and looked at it as a spreadsheet, but nothing could explain the error.
At this point I had lost all faith in Simplifi’s ability to accurately do math, and thus everything it was showing me was suspect. I tried chatting with a “coach” but they were worse than useless, asking stupid questions like “when did you set up the account” instead of just looking at the issue.
I decided to delete my Simplifi account and go back to GnuCash, but it turns out you can’t delete your account. It sticks around until your subscription runs out, which in my case is December. Instead I could go and make sure auto-renewal was turned off and then I manually deleted all of the accounts I had so painstakingly set up over the holidays until it showed a “zero” balance.
For me Simplifi is crap: a shoddy system that has no internal consistency, but all other online hosted solutions seem similar, at least the ones with prices I’m will to consider. I’m certain Simplifi is useful for some people, and it is “pretty”, but I don’t want simplicity over accuracy.