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Expensify Is a Great Start, But No Guarantee

A set of promising ideas only raises hopes for automated expense reporting and reimbursements.

Small-business accounting on the Web -- in particular, nasty little bits such as expense management -- is turning out to be one wicked business problem.

Tracking all the money the 25 million or so American small businesses make and spend has turned into one of the Web's darlings. Small-business software giants such as


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, which host online products including

QuickBooks Online



TurboTax Online

, continue to post nutty-for-this-economy numbers such as a return on assets that's up close to four times year over year.

This hurricane of cash has spun up a dust storm of nouveau-accounting wannabes. Some are well known, such as

H&R Block

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. And others are not, like

Credit Sesame




Receivables Exchange


And the sophistication here is only just beginning. San Francisco-based


, started in 2008 by David Barrett, focuses on just one piece of the bean-counting dark arts: expense reports. Considering that expense management is literally job one for most small firms, I have been testing this product since early last year.

And in about a year and a half of use, some valuable lessons about managing small-business fiscal processes on the Web have become clear.


Expensify is unquestionably a fresh approach to managing company expenses.

What Expensify does, where possible, is automate the process of capturing, tabulating, filing and getting reimbursed for purchases you make in the course of doing work. The backbone of the system is the so-called Guaranteed eReceipt, which the company says is the full digital replacement for some credit card purchases under $75. Expensify, once authorized by you, imports these eReceipts from online credit card statements and mixes them with hand-entered cash spending and car mileage allowances. It can even import photographs of paper receipts taken by a smartphone. And all of that is automatically cooked up into an IRS-ready expense form for reimbursement. Which, in turn, can be e-mailed, tracked and managed in an accounting package such as QuickBooks and FreshBooks or exported as a PDF for hard printing. All very clever.

By and large, for certain types of basic expenses, the system works. Once set up, my company

American Express

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card spending did feed Expensify automatically. I was particularly impressed with the mileage reports, which were eerily accurate.

Overall, I can recommend Expensify as a good first step for making sure your company money is going where it should.


Nothing close to a truly automatic expense system.

After long term use, however, it turns out the gritty, bean-counting ins and outs of the U.S. finance system are just too much for this -- or probably any -- automatic tool.

First off, large corporate clients -- mine, at least -- refuse separate expense forms. Rather they want expenses mixed with invoices into a single form they can pay with a single check. So while Expensify can be imported into, say, QuickBooks and turned into an invoice, the incoming data is mucked up just enough to require careful, time-consuming by-hand justification. For example, the eReceipt transaction dates can lag the actual transaction dates by almost two days, which fetches a big fat red flag from most accounting departments.

"That's an unfortunate artifact of how the credit card networks work," David Barrett wrote in one of many e-mails we exchanged about this problem. He described how credit card companies and vendors break up transactions into separate steps, which can fool his software. "We have some tricks planned to get the 'sales date,' but they're really gnarly ... I'll make a note to bump it up in priority."

Even for plain expense forms, Expensify cannot manage certain transactions from hotel lodging and restaurants. I found I was double-checking my Expensify reports against my ledgers, by hand, to make sure no fiscal gremlins lurked in my books.

As cool an idea as Expensify is, there was no meaningful time savings for managing the expenses of my small business.


Expensify is by no means shabby. In fact, as a first step for managing expenses it's absolutely worth a look. And as guide as to what's possible with making business processes lean and mean, it's a promising idea. But after a year of wrestling with this tool, I am dubious about the chances of this -- or really any other -- online automated fiscal product.

When it comes to managing money, the Web is just too darn tough.

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Jonathan Blum is an independent technology writer and analyst living in Westchester, N.Y. He has written for The Associated Press and Popular Science and appeared on Fox News and The WB.