After a year of the "keep receipts in a big folder!" methodology, desktop and web-based, gratis and paid) I decided to limit myself to...

  1. web-based services
  2. with minimal basic functionality (deal-breakers for me: secure, must get information from most of my online accounts, help me budget, and give me an easy "from X time to Y time" summary view)
  3. that costs $0
  4. and easily export/sync to a standard file format you can work with using other programs on your desktop (no lock-in).

The Contenders:

mint_logo7clearcheckbook-logoyodlee_logowesabe_logo

  • Mint is a spending tracker that automatically recommends products and services to you.
  • ClearCheckbook is "an online checkbook register with the added bonus of viewing reports, setting budgets, creating reminders and more."
  • Yodlee is what Mint is built on top of ("that with which Mint is built on top"?).
  • Wesabe is a money management tool with community features built in.

The Criteria:

  1. Does the program make me feel happy when I use it? (This is largely a function of thoughtful UI design.)
  2. How easy is it for the program to download and use financial data from your bank, etc. accounts?  (best: automatic.)
  3. How many of my accounts can be linked to the program, so I don't have to enter transactions in by hand? (best: all of them.)
  4. Will it force me to review my finances on a regular basis? The most likely scenario for this is some sort of push communication, for instance "email me updates once a $timeperiod. (best: yes, and we'll make it compelling for you to track your progress, and as a bonus, it looks pretty.)
  5. Can I check my financial status on the go? The most likely scenario for this is being able to get reports via SMS, email, and/or IM. (best: yes, and we show you all your budget category status numbers too.)
  6. Can I update my financial status on the go - in a way I'll actually do it? For instance, being able to SMS in "I spent $1 on a cookie, this comes from my 'fun' budget" would fit the bill. (best: yes, and you can fill in all the fields via SMS/etc. you'd be able to fill in online, so you don't have to go back and add metadata to your transactions later.)
  7. How many and which programs does the file format you export to work with? (best: yes, Mel, we work with tax preparation software...)
  8. Do you import file formats from other financial programs? (Not super-important, but in case I ever switch to something else and then want to go back...)
  9. Is the program smart about moving/renaming/merging/splitting/<insert-set-operations-here> categories and/or tags for expenditures? (best: yes, and there's an undo.)
  10. What other cool things can you show me that I haven't thought of?

The procedure

For each service, I am going to...

  1. Create an account.
  2. Link it to as many of my financial accounts as possible (savings, checking, IRA, stocks...).
  3. Input (manually, with the online interface) May 2009 expenses so far.
  4. Check my budget status (with the non-online interface) before taking any spending-money actions during the next week.
  5. Input (manually, with the non-online interface if applicable) May 2009 expenses during the next week.
  6. Review my financial status on Monday, 5/18.
  7. Try out the criteria in the list above I haven't exercised yet.
  8. Draw up the final ranking.
  9. Make a decision.
  10. Export and back up my financial data

Stay tuned for the results.