What are your greatest tax season pain points?


As we think through new features to offer our small business and entrepreneur users, we're looking to the coming tax season as the time of year when most prefer not to have the distractions from their business, forced upon them by the IRS. So, what consumes the most of your time and what would you most benefit from when preparing taxes for your business?

Think through everything you have to do and not just bookkeeping and end of year taxes; for example:

  • Dealing with W9s and 1099s
  • Filing Estimated Taxes
  • Managing end of year inventory and cost of goods sold
  • Dealing with deductions, especially things like mileage and a home office
  • Figuring out depreciation
  • Record keeping and data entry
  • Preparing tax forms

Tax Business

asked Dec 4 '09 at 12:21
Paul O'brien
521 points
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3 Answers


Hard to pick a specific thing being the biggest pain. It's more of a "death by a thousand paper cuts" situation. The amount of tax-related paperwork we deal with every year is astounding. It's not just the IRS, it's state, city and various related agencies. All have extensive record keeping requirements, have hard deadlines and carry penalties for noncompliance (some criminal!). Here's what's typical for a 4 employee S-corp based in Seattle:

Every Two Weeks

  • Payroll Taxes
  • 401k Contribution
Every Quarter
  • Washington State Business and Occupation Tax
  • City of Seattle Business License Tax
  • Labor and Industries (Worker's Comp) Tax
  • Washington State Employment Security Department (Unemployment) Tax
  • Employer's Quarterly Federal Tax (Form 941)
  • Estimated Federal Taxes
Every Year
  • Washington State Business License Renewal
  • City of Seattle Business License Renewal
  • City of Seattle Employee Hours Tax
  • Business Personal Property Listing
  • Employer’s Annual Federal Unemployment (FUTA) Tax (Form 940)
  • Federal Form 1096 and 1099s for all eligible vendors / contractors
  • Form W3 and W2s for every employee
  • US Income Tax Return for an S Corp (1120S), Schedule K1 and depreciation schedules
  • 401k annual report (Form 5500)
answered May 27 '10 at 12:51
Oleg Barshay
2,091 points


For my retail book business, doing the physical inventory year end count is time consuming and something I do not look forward to. The calculation is all set up in an excel file. The tedious count is what I dread.

I use quickbooks and my revenue and expenses are already recorded regularly. Having a simple low cost fixed asset depreciation calculation that integrates with my regular accounting would be great. Currently, I calculate depreciation separately at year end and manually book the entries into quickbooks.

answered Dec 10 '09 at 03:35
Starr Ed
948 points


All of these things are horrifying, but I'll throw in another: the S-Corp Cash Shuffle.

This is where you make a bunch of business purchases before the end of the year and try to push off customer payments to you into the new year so you don't get smacked with a huge personal tax bill. Do you know how counter-intuitive it is to try to convince your customers not to pay you?

answered Dec 4 '09 at 23:19
Doug Bright
141 points

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