Receipt envelopes quickly piled up and finding anything was a pain so the envelope method didn’t last long. Money / Quicken + scanned receipt “sheets” Each month I would put my receipts in a different envelope. Soon I realized the value of saving them which included: reconciling help, returns, warranties, price matching, taxes, reimbursements, rebates, insurance and more. Throwing away receipts bit me several times, even ones I thought unimportant. I would key in my receipts and then throw them away. Suddenly tracking, reporting, forecasting, budgeting, reconciling and more became manageable. Money really helped me get a handle on my finances.

If you were born in the late 70’s or after and you are still here, you are in the minority. I gave this up probably 12 years ago and have never looked back. In other words, the time of check registers and hand-written paperwork.

A custom receipt scanning and uploading applicationīackground First I believe it is helpful to review the path that lead me here.

A script to import the data into Quicken?.

Exporting the data from Shoeboxed to Quicken.

After staring in despair at my last stack of receipts on my desk, I decided to take a shot at automating some of this work with a trial of along with some other changes along the way. This is especially true with keying in transactions from various receipts, and even more so if you want to digitally manage the receipts, bills and related documents.

The downside to this goal is that achieving it tends to require a lot of tedious, boring work when you have many financial transactions. I have never liked the paperwork involved though so I have always strived for paperless personal finance in this digital world. While most of my transactions are personal and not business expenses, I still find this a worthwhile investment. Money, Quicken), scanning and shredding receipts and bills, online bill pay, e-statements, sites like, and various other tools and techniques. This has included entering transactions into financial software (i.e. I try to be pretty organized with my finances otherwise I cannot tame the beast.

Quicken 2017 home and business menu bar