FreshBooks, Outright and Shoeboxed: A Tax Time Perfect Storm

Small Business Web Cupcakes!

One of the reasons some of our buddies in The Small Business Web seem to work so well together is the overlap between the things we’re all trying to do for customers.

FreshBooks is focused on helping you answer simple questions like: Who owes me money? How much am I billing? How do I get paid faster?

Shoeboxed lets you take care of that big old pile of crumpled receipts and business cards. You can mail them all in to Shoeboxed in a pre-paid envelope, send expenses by email, or even from pics snapped with your cellphone camera. They’ll scan everything in, enter the data, and organize everything for you.

Outright comes at things from the other end.  For sole-proprietors and small business owners, Outright is a simple online accounting system that helps business owners manage their finances and automate much of the work in prepping their taxes at the end of the year.

Put the three together and it gets better: Shoeboxed exports billable receipts straight to FreshBooks so they can be recouped from your clients and it lets you pull the receipts through into Outright to keep your accounts all straight. Of course, Outright also records income from the invoices you raise through FreshBooks, alongside those expenses brought in from Shoeboxed.

This year, at tax time, one of our users confirmed how cool this integration is. Check this out:

Being a young entrepreneur the last thing I want to spend time on is tedious accounting work. I’ve been using FreshBooks for a few years for invoicing, billing, and pseudo expense tracking but when I stumbled upon and, I felt like the accounting weight was taken off my shoulders. It may sound over-dramatic but I am really not disciplined enough to keep proper records, and my accountant would not be happy with my scattered shoebox and spreadsheet full of notes – usually done at the last minute. makes it easy for a simpleton like myself to keep track of expenses. Just snap a picture of a receipt, send it on and I’m done with it. No more spreadsheets or boxes full of crinkled receipts makes me happy. Add Outright into the picture and it imports all of my expenses from my business accounts, via Shoeboxed and Expensify, categorizes them and puts my accounting on autopilot.

Having this all done automatically and up to the minute is amazing. It’s so much easier to handle accounting issues like expenses, estimated tax payments, etc. and I feel more in control and aware of my business than ever before. I’m positive without these tools my accounting book would be a mess and my accountant wouldn’t have bought ME a box of chocolates on tax day.

— Evan Roberts


The only challenge now is what should we call this thing?  We’ve been going back and forth with our friends at Outright and Shoeboxed:

FreshOutBoxed? ShoeBooksRight? OutBoxedBooks?

Either way: great to hear it’s working for Evan, hope it’s working for you too.

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