Simplifi might be the best spend tracker of the bunch. I decided Personal Capital wasn’t for me because of these limitations. I noticed that it doesn’t seem to look at investment values retrospectively, so it won’t do a good job at tracking net worth if you enter backdated transactions instead of entering them day-of. Personal Capital is more oriented towards investment tracking, and has some nice capabilities there, but seems very limited in tracking manually-entered transactions. Maybe I need to move to a workflow where payments are automated so I don’t really need to actively keep track… I have a lot of credit cards, so tracking the bills is key functionality for me, and something I’d have to do elsewhere if my personal finance software doesn’t support it. I’m somewhat mystified that competing solutions like Simplifi and Banktivity don’t seem to import or display credit card payments due, and only support setting up reoccurring bills with predictable amounts. It’s worth noting that one thing Mint does well that none of the other software seemed to support is keeping track of upcoming credit card bills. Overall, I liked Simplifi more for transaction tracking, so I decided to drop Mint from consideration. I know there’s an ad-free version, and I definitely would have upgraded to it if I decided to stick with Mint, but the initial experience left a bad taste. I also didn’t like marketing-heavy approach, with lots of upsells and advertisements throughout the UI. Since I have private investments and I refuse to hand over banking credentials to third parties, this made it feel like a bad fit. It seems very heavily oriented towards transaction downloading and doesn’t have good capabilities for tracking accounts that it can’t connect to. Mint seems pretty decent for transaction tracking, but it had a few downsides that made me drop it from consideration. I suspect I could have worked around the workflow YNAB tries to impose and made it work for me, but it didn’t seem worth the friction of circumventing the workflow, especially at a relatively high price point. I’m more interested in understanding how my spending breaks down than managing cash flow, which isn’t a concern at all. It’s very focused on budgeting, which is not really what I want (and actually runs counter to my desire to relax a little bit about spending money). While I admire the polished interface, I found the workflow didn’t work for me. YNAB has a devoted following and comes with many online recommendations, so I was enthusastic to try it. I’m mainly focused on tracking spending (not budgeting), but if an app can partially or completely replace the asset/liability spreadsheet by tracking investments as well, that’s worth exploring as well. I also am looking for a good mobile app where I can enter transactions on the go - this was awkward with the spreadsheet setup so it’s one of the things I want to improve. I'm a Mac user, so for packages that have native desktop application, they need a solid Mac version. One of the most important is that I am NOT willing to share any deposit account or brokerage credentials with a third party, so software that depends on this to work well is out of the running (granting data access without providing credentials is okay). I thought I would post some notes here on my journey in case they are helpful to others. Some of the apps can also track investments, which could be useful to me as well. I'm also hoping that automating this tracking will let me become a little more hands-off and relaxed about routine spending, without giving up visibility. In an effort to simplify my life, I recently looked at several personal finance apps that can help automate this process by automatically downloading and categorizing credit card transactions. Most transactions require me to manually update both spreadsheets. I also have a second spreadsheet that tracks assets and liabilities (i.e. This habit stuck, and I’ve been pretty religious about tracking transactions. Back in 2010 I realized I had no idea how much money I was spending and where that spending was going, so I started keeping a spreadsheet tracking transactions by category.
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