Soothing the Tax Headache: An Interview With

Welcome to tax season. If you’re a small business owner, those words might induce a shudder. For many of us, tax season means scrambling to itemize, catching up on stray expenses, and rushing to send contractors and employees the right forms at the right time. Unless you’re a CPA or other tax expert, tax season can be one prolonged headache.

The people behind Outright want to help. They founded the online bookkeeping software after watching small business owners flail during tax season. Rather than spending hours compiling tax data, why not live your life? That’s what Outright aims to help you do. The bookkeeping software is free, Web-based, and intuitive enough to ease the aches out of tax work.

Outright also recently launched Right Taxes Now, a blog devoted to helping those in the business community make positive changes both their own tax understanding and government tax legislation. We talked to Kevin Reeth, Outright’s CEO, and Marketing VP Paul O’Brien to get their take on small business, taxes, and what needs to happen at the places where they intersect.

BP: What are some of the biggest mistakes small business owners make when doing their taxes?

One, not paying taxes because they don’t think it’s a lot of money or because they have other bills. Or they wait until the end of the year, instead of paying estimated taxes throughout the year. Another is to allow themselves to get disorganized, which causes them to miss important deductions or critical tax deadlines. And of course, there’s the fear of claiming the home office deduction – even though more than half of all small businesses are home-based, the majority don’t claim the home office deduction.

BP: What’s the biggest point of pain that Outright removes for those people?

Outright help get entrepreneurs get organized, automating a lot of their recordkeeping and reminding them to pay estimated taxes on time.

Let’s switch gears to RightTaxesNow. Can you tell me a little bit about what the website does, and what its goals are? is a community web site that’s been created to highlight the tax-related issues that cause really small businesses the most trouble, and to rally people in an effort to influence legislation that could simplify taxes and make entrepreneurship easier. If we really want small business the step up, create jobs, and help get this economy back on track, we’d be well served to make it easier to be in business.

BP: What are some of the biggest tax changes facing sole proprietors and small business owners this year?

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The real impact on small business owners is just the amount of changes in tax laws and, maybe even worse, the unknown, of what Washington may do next with tax rates. Very few of the 2009 tax law changes had any broad impact either positive or negative on small businesses, but there has been so press about law changes, most of which impact individuals that business owners are concerned they can’t keep up.

One positive law change has been the ability to carry back operating losses, to still take advantage of them; it seems though, the majority of small business owners are doing well enough this change has little benefit to anyone.

BP: If you had one sentence of advice to give small business owners this year regarding their taxes, what would it be?

Actually, it would be to get organized so they spend as little time dealing with taxes, and as much time as possible earning a living.

BP: Any other remarks?

If you can’t tell from the direction we’re heading, we’re fed up with the support self employed professionals get from the government, and even big businesses like the credit markets and banks. is designed to make it not only very easy to keep up, but to help entrepreneurs all but forget about the business of running a business. We’ll take care of your bookkeeping, help with taxes, and now, with Right Taxes Now, we intend to change things for the better for people just trying to make a living.

For more on small business, taxes, and how to make the two gel, visit Outright and Right Taxes Now.

Written by Drea Knufken

Drea Knufken

Currently, I create and execute content- and PR strategies for clients, including thought leadership and messaging. I also ghostwrite and produce press releases, white papers, case studies and other collateral.