Can you sell your business and pay $0 in federal income tax?

About the Episode

Did you know that a tax benefit, the Qualified Small Business Stock (QSBS) tax exclusion, can save you millions? Discover how properly structuring your company from the start can lead to a tax-free sale of your C Corporation, potentially saving you millions. You’ll learn the crucial steps to take now to prepare for a successful and highly profitable exit later.

It’s worth it to put a little thought into tax planning your transaction, and it’s worth it to do it early.

Roger Royse

What You’ll Learn

  • Understanding the QSBS Tax Exclusion: Learn about the most significant tax benefit available to business owners selling a C Corporation. This little-known rule can allow you to sell your company and exclude up to $10 million or more in capital gains from your federal taxable income.
  • The importance of early tax planning: Discover why tax planning for your business exit should begin long before you think about selling. You’ll understand why it’s crucial to consult with tax and legal professionals early to ensure your company qualifies for the lucrative QSBS exclusion, which requires a minimum five-year holding period.
  • The C Corp Advantage: Understand why only C Corporations qualify for the full QSBS tax benefit, and why other business structures like LLCs and S Corps are at a disadvantage when it comes to maximizing a tax-free exit. This lesson will help you determine if your current structure is holding you back from a massive payday.
  • Avoid Common Pitfalls that will Disqualify You: Learn about the common mistakes business owners make that can disqualify them from the QSBS tax exclusion. We’ll cover everything from the types of businesses that don’t qualify to rules around stock redemption and secondary sales that could tank your tax savings.

Topics Covered

What is Qualified Small Business Stock (QSBS) and why is it so important for a business sale? [1:15]
The financial benefit: How QSBS can create a tax-free business exit [3:40]
Defining a Qualified Small Business: What types of businesses are eligible? [5:45]
C Corporation requirements and why other business structures don’t qualify [6:51]
The difference between stock sales and asset sales regarding QSBS [7:47]
The danger of liquidating a subsidiary and losing your tax basis [11:49]
Navigating the original issued stock rule to preserve your tax benefits [18:06]
Converting your LLC or S Corp into a C Corp for a tax-advantaged exit [24:33]
Understanding F reorgs to strategically restructure for a sale [27:58]
The right time to involve a tax attorney or specialized CPA [31:50]

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Meet Our Guest

Roger Royse

Roger Royse

Partner at Haynes and Boone, LLP | Palo Alto, CA

Roger is a nationally recognized authority on agtech – the technology of food production – and the legal considerations for companies in this industry. Roger is also the author of 10,000 Startups: Legal Strategies for Startup Success and Dead on Arrival: How to Avoid the Legal Mistakes That Could Kill Your Startup and has been interviewed and quoted in the Wall Street Journal, Forbes, Fox Business, Chicago Tribune, Associated Press, Tax Notes, Inc. Magazine, Nikkei Asian Review, China Daily, San Francisco Chronicle, Reuters, The Recorder, 7X7, Business Insurance, ABA Journal, Thrive Global and Fast Company.

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