It seems like every year I send an urgent newsletter advising corporate transactional lawyers that an 11th hour tax bill has opened a short window for some tax-advantaged transactions, and 2014 is no different.  Thank the lame-duck Congress for the Tax Increase Prevention Act of 2014 (TIPA), which breathes one more year of life into several taxpayer-friendly laws that had expired at the end of 2013.

Among the so-called “tax extenders” are a few provisions of particular interest to entrepreneurs and small-to-medium size businesses.  These extensions are retroactive to the beginning of 2014, but will expire (unless extended again) on December 31.

Be on the lookout for the following last-minute, tax-saving transactions:

  • Acquire qualified small business stock (QSBS).  The 0% tax rate (hard to get lower than that) for QSBS has been extended for stock acquired during 2014 (and thence held for 5 years).  It’s unlikely you’ll start a new company in the next eight days, but you can acquire QSBS in other ways on short-notice:
    • Convert an LLC to a C corporation.  This may be useful if you believe the LLC will convert to a C corporation anyway.  You don’t even have to form a new entity – you can file Form 8832 to elect for the existing entity to be taxed as a corporation.
    • Exercise options.  If the stock you receive is unvested, you will likely want to file a Section 83(b) election.
    • Convert notes.  This may be useful if you hold bridge notes that will convert into preferred stock at the next financing.  Depending on the circumstances, you might convert into stock now and adjust the purchase price later.
  • Purchase equipment.  Special expensing and depreciation provisions have been extended through December 31.  You can immediately write-off up to $500,000 of depreciable business property and take 50% bonus depreciation on even bigger purchases.
  • Sell the assets of certain S corporations.  This is an additional benefit for S corporations that converted from C corporation status at least 5 but fewer than 10 years ago.  Generally, the “built-in gain” in a C corporation’s assets remains subject to double-tax for 10 years after the S election.  That 10-year period is reduced to 5 years for assets sold in 2014.
  • Redeploy capital in foreign subsidiaries.  This one is technical but a significant benefit if you own multiple “controlled foreign corporations.”  Generally, moving cash around related CFCs through the payment of dividends, interest, rents, and royalties can trigger immediate US tax liability for certain US shareholders unless (among other conditions) the payment is between corporations organized in the same country.  Through 2014, related CFCs can pay dividends, interest, rents, and royalties to each other regardless of their country of organization if certain conditions are met (generally, if the payment is attributable to the income of an active business conducted outside the US).

Not all taxpayers will benefit from these opportunities, and as always there are hoops and fences to jump through and over.  You should consult a good, independent tax advisor to determine whether and how these tax advantages apply to you and your clients.