Qualified Small Business Stock – Tax Benefit That Could Pay Millions

About the Episode

Qualified small business stock (QSBS) is a provision in the U.S. tax code that can provide tax-free income to investors. This engaging conversation about the tax benefits of QSBS is geared toward buyers and sellers. Jessica Fairchild and Andrew Szymulanski discuss who benefits from QSBS, what the requirements are to qualify for this tax benefit, and ways to make the structure work for a small business sale or acquisition. Discover why it’s worth possibly structuring a transaction to qualify for QSBS treatment.

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“QSBS is quite a powerful tax planning tool that is very different from other tax incentives. It’s an incentive to help small businesses get off the ground.” 

Andrew Szymulanski

In this Episode

2:28 What is QSBS (qualified small business stock), and why is this important in M&A?
4:44 How much money can be saved in terms of taxes in QSBS?
6:12 Why is QSBS  not common knowledge with M&A advisors, attorneys, accountants, and other professionals involved in M&A transactions?
10:28 How do the IRS rules play a part in QSBS?  
13:40 What is an example of how the QSBS tax structure works in an M&A transaction?
16:34 Why are sophisticated investors such as family offices unaware of the QSBS structure?
19:30 How much money could an independent sponsor save when they exit an investment?
21:50 What are some of the requirements that must be met for a QSBS structure to work? []
25:35 How can the seller of a business benefit from QSBS?
28:10 Is it possible for the owner of a C-Corp to sell their business and not pay any taxes if the requirements are met for a QSBS structure?
31:15 What are the criteria for qualifying? Why does QSBS only apply to C-Corps?
34:58 Is there an exclusion for the 5-year rule for C-Corps?
36:27 What’s the best deal structure for QSBS?
41:06 Why is it called QSBS stock?
42:07 What are some of the other major requirements in QSBS?
49:06 Why should both an M&A attorney and a tax attorney be involved in a QSBS transaction?
52:20 What are the potential impacts of having a tax attorney versus a CPA working on a transaction? Does a company need to be a specific size to benefit from working with a tax attorney?
1:01:02 What types of businesses qualify or do not qualify for QSBS treatment?
1:02:45 What are the most important takeaways when it comes to QSBS?

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Resources Mentioned in This Episode

Terms Mentioned in This Episode

  • Asset Sale: Transfer of a company’s individual assets rather than the entire business.
  • C-Corp: C Corporation – a legal structure for a corporation that is taxed separately from its owners.
  • CPA: Certified Public Accountant
  • ETA: Entrepreneurship Through Acquisition – the process of entering entrepreneurship by acquiring and growing an existing small business.
  • Fundless Sponsor: A private equity professional seeking deals without a dedicated fund.
  • Independent Sponsor: A deal-specific private equity investor lacking a dedicated fund.
  • IRS: Internal Revenue Service is a U.S. government agency responsible for tax collection and enforcement.
  • QSBS: Qualified Small Business Stock, U.S. tax incentive for eligible small business stock.
  • S-Corp: S Corporation is a corporation that elects to pass corporate income, losses, deductions, and credits through to shareholders.
  • Stock Sale: Transfer of ownership through the sale of company shares.

Meet Our Guest

Jessica Fairchild

Jessica Fairchild

Lawyer | Entrepreneur

Jessica Fairchild is a lawyer, law firm leader, women’s advocate, and entrepreneur. She is currently a Co-Chair of the Management Committee and a partner at Croke Fairchild Duarte & Beres LLC, a law firm headquartered in Chicago with over 60 lawyers.

Jessica co-founded Croke Fairchild in 2019 after having worked in several other law firms that she founded and managed. Jessica’s principal legal focus for over 22 years has been on corporate law and mergers and acquisitions matters, where she counsels founders, private equity sponsors, family enterprises, and corporations.

From 2007 to 2009, Jessica served as General Counsel to Chicago 2016, the organization that led Chicago’s bid for the 2016 Olympic and Paralympic Games. Prior to that, she was a corporate attorney at Sidley Austin LLP in Chicago, where her work focused on M&A, corporate, and securities matters.

Jessica received her J.D. in 2000 from The University of Chicago Law School, where she graduated with high honors. She was recognized as one of Crain’s Chicago Business’ 2022 and 2021 Notable Gen X Leaders in Accounting, Consulting, and Law.

Meet Our Guest

Andrew Szymulanski

Andrew Szymulanski

General Tax Practitioner

Andrew is a general tax practitioner with a wide variety of transactional tax planning, compliance, and controversy experience. He has been in practice for more than 20 years, and his clients range from Fortune 500 companies to small businesses and individuals. Andrew takes pride in adopting a holistic approach to tax planning, the interaction of which frequently involves consideration of business succession and estate planning.

Prior to joining Croke Fairchild Duarte & Beres LLC, Andrew’s tax practice included tenures with the Chicago office of the international law firm Baker & McKenzie LLP, where he focused his practice on international tax matters and cross-border transactions, and roles with prominent international accounting firms.

Andrew is a member of the American Bar Association and the Chicago Bar Association and often speaks and publishes on topics involving tax matters. Andrew holds a B.A. in Finance and a B.A. in Economics from the University of Illinois and received his J.D. from The George Washington University Law School.

Location Location: Chicago, Illinois

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