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Cut The Clutter And Keep Your Receipts Organized With Shoeboxed

Keeping receipts organized for tax time can be a pain. Every year you vow to do better yet when tax time rolls around you’re digging through piles of receipts again. Here is a review of Shoeboxed, a digital service that helps you keep your receipts nice and organized.


Cut The Clutter And Keep Your Receipts Organized With ShoeboxedAlmost no one likes tax time, and for the past two years my receipt tracking system has been a cluttered sight to behold. It consists of this: a dozen plastic toy bins repurposed as receipt holders. While the bins are marked for different categories such as “entertainment” or “charity donations,” after 12 months the piles have no semblance of organization whatsoever.

In April, adding up all that paper took about five hours. But that didn’t include hunting down utility and phone bills, digging up electronic receipts and double- checking the math. By then, I’d easily spent half a day in pure fiscal hell, punctuated by the nagging worry that I somehow got things wrong: lost receipts, forgotten receipts, illegible receipts, accidentally counting receipts from 2013 or 2015.

So on April 16, my wife and I made a pact to do things differently. But by then the 2015 receipt mound was already rearing its ugly paper head. What to do?

Just as there are now websites for robo-investing, and social networks for financial strategy, it turns out there are digital solutions for receipt tracking. So we took our modest 2014 refund and plowed it back into a yearlong subscription to Shoeboxed.

Shoeboxed is one of several app- and web-based receipt solutions on the market, including OneReceipt, NeatReceipts, Evernote’s Receipts and Certify. All get high marks from TechRepublic as smart, intuitive archiving systems. It’s safe to say that no matter which one you pick, you’ll find advantages that suit your particular situation.

The Receipts app, for example, doesn’t require you to set up an account: It’s a mobile app with a clean, user-friendly interface (but a terrible name to search on Google, as it’s virtually impossible to find without knowing that Evernote makes it). And Certify, though it requires a learning curve, has ubiquity across all mobile platforms: iOS, Android, BlackBerry and Windows Phone.

As regular readers of this column know, I need things bonehead simple. My choice required me to use it right out of the box, or the Shoeboxed, if you will. It also has some nifty bonuses.

For starters, Shoeboxed allows you to digitally store business cards, while the mobile app (iOS, Android) lets you track and enter mileage for tax purposes.

As for receipts, Shoeboxed works in three easy ways.

  • You can photograph receipts via smartphone.
  • A desktop app lets you upload e-receipts in a flash.
  • And the Shoeboxed website uses a drag-and-drop system where you can easily track and categorize spending.

I’ve tried all three methods and each works faster than you can say “uncrumple that receipt.” You can also sync Shoeboxed to your primary email address and it will “recognize” receipts and enter them into your account. Though I’ve linked it with my Gmail address I haven’t run the trial yet, so I can’t report on its efficacy.

Shoeboxed has five tiers of membership.

The first, which is free, allows you to upload five scanned documents per month. It’s fine for low-impact receipt sorting.

The most expensive, Executive, costs $99.95 per month or $83.25 if you pay $1,000 annually. It allows you to enter a massive 1,000 documents a month and integrates with QuickBooks.

The most popular option—and the one I chose—is the Classic ($29.95 per month, or $24.92 if you pay $300 annually). With Classic, I can link my account to two users (me and my wife). What’s more I get access to “Magic Envelopes.”

Think Netflix DVDs and you’ll get how this works. Just a few days ago, I sent a mess of paper receipts to Shoeboxed in a prepaid envelope. (I was told I didn’t even have to take them out their semi-wadded state, but I didn’t want to be rude.) Once they arrive at the Shoeboxed HQ in Durham, N.C., they scan them by hand into my account within 1 to 3 days. The receipts are then mailed back along with another Magic Envelope.

Classic gives you 150 documents a month, and I probably hit that threshold with my first dispatch. The package looked like a puffy baby pillow when I plunked it in the mailbox.

Still, I have confidence the Shoeboxed team will follow through. This tech-savvy lot skews overwhelmingly toward the millennial side: CEO-Founder Taylor Mingos just celebrated his 30th birthday.

And so far, my customer service requests have been answered with lightning speed. When my password got e-mangled on a recent Monday, I was disappointed that the online live chat feature didn’t work. But Shoeboxed did get back to me via email that same day and fixed the problem in a few minutes.

There’s also one weak link that needs fixing. The desktop app asks for your username when it really needs is your email address. This leads to my account locking up when I try to enter the one instead of the other; I get the message “login credentials invalid.”

Still, these are minor niggles given what Shoeboxed is doing to simplify and straighten out my financial life. My accountant will love me when I export all the data next year, via QuickBooks or a spreadsheet. And I consider the $300 annual fee a fine case of opportunity cost on the plus side. You can’t put a price on stress and anxiety—as well as potential mistakes—arising from a messy receipt system. I know; I was audited in 2001 and had to pay the IRS $750 because of two missing receipts.

Did I count the receipts I sent in? Nope. But will Shoeboxed count up the dollars and cents for me? Yup.

Meanwhile, I’m prepping the toy bins for our next garage sale.

Learn more or try Shoeboxes now

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About Lou Carlozo

Based in Chicago, Lou Carlozo is a personal finance contributor for Reuters Money, a columnist with DealNews.com, and a former managing editor at AOL's WalletPop.com. Contact him with story ideas for Money Under 30 at feedbacker@aol.com, or follow him via LinkedIn and Twitter (@LouCarlozo63).

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