This is the time of the year many of you inevitably spend a weekend or so sorting the box-full of receipts you had collected throughout the year – you need to re-read them, try to remember details, categorize, sort, in preparation of either preparing your own Tax Return, or handing them over to your accountant.
Or you can just dump them all on to Shoeboxed, a service that scans and categorizes all your receipts, and provides them in the electronic format of your choice. (They do for your bills what ScanCafe does for your photo prints.)
And it gets better: yesterday Ben reported that the popular Web-based invoicing solution, FreshBooks is now integrated with ShoeBoxed. So now you can have your paper expense receipts show up in an invoicing app directly. Voila!
It’s better than fiddling with paper, stuffing envelopes and wait for Snail Mail – but it really that good? I don’t know about you, but I barely ever use cash nowadays – except for the local farmers’ market, and that’s not a reimbursable / deductable expense. So here’s the maddening part: most expense transactions start their life electronically, and we only print them on paper to have an official record – whether it’s for the tax authorities or for Clients to bill out to. Either way, the paper receipts will be converted back to electronic format. I’ll repeat: in most cases we only generate and safeguard paper as a temporary medium between two electronic formats. Isn’t that ridiculous?

We can get most of our expenses, originally paid for by credit card, check, or bank transfer automatically downloaded into Money Management / Accounting software. No paper was required to effect payment, there is a "record of transaction" behind every single credit card charge, so wouldn’t it suffice as proof of expense?
There are significant attempts at paperless expensing in the Enterprise sphere, for example Amex and Concur provide end-to-end systems that take care of the entire process from travel booking through expensing to reimbursement. But the process depends on a number of vendor agreements, e.g. major hotel chains and airlines providing e-receipts that Concur can match up with the Amex record. Should the banks that already provide me with an electronic record of my transactions be the authentic source of all expense information?
Here’s my dream 22nd century (?) very SaaS-y version of expense reporting:
- Payment transactions automatically downloaded into my personal money management software (Quicken, Money, Mint ..etc) – this is already happening.
Next, what will it take to:
- Pull items from Quicken et al into the expense report ( I am already doing this)
- Have the expense system collect the electronic record (link to it) automagically
- Submit it all, again electronically
I suppose there are a number of data format / standards issues, but also non-technical, legal, tax regulatory, privacy issues to overcome here. I don’t claim to be an expert, but am in the lucky situation that we already have the cream of the financial profession, CEO’s of Accounting startups, established firms, Accountants and Lawyers regularly comment here @ CloudAve, thanks to Ben’s Accounting 2.0 series. So here’s the challenge: let’s channel all this chatter into something constructive, and try to define what it will take to get to my 22nd Century Expense Management system.
And does it really have to be 22nd century, or will I see it in my lifetime?
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