QSBS Rollovers

Expanding Gain Exclusions After the Sale of QSBS

Can a QSBS Rollover Save you Millions?

Do you have a gain from the sale of Qualified Small Business Stock (QSBS)? You may have heard about QSBS rollovers (IRC 1045) which enable QSBS gain holders to defer taxes and multiply their exclusion eligibility under IRC Section 1202, potentially paying zero in taxes on their entire QSBS gain. We can help you navigate the QSBS rollover process through a unique partnership program that is well-suited for those with QSBS rollover gains.

You could benefit from a QSBS rollover if:

  • You recently sold QSBS before the 5 year minimum hold period

  • You recently sold QSBS that you held for 5 years, but your gain exceeds $10M

  • You’re considering an exit in the next 1-4 years and want to think ahead about tax planning

  • Are an angel investor seeking flexible QSBS opportunities to help defer gains

The Vint Retail Partnership Program can be a solution for QSBS gain holders in need of a flexible, low-risk, and relatively liquid QSBS opportunity. Get in touch with our team today to learn how to partner with us and save up to $3,400,000 or more in gains tax from your stock sale.

(Read more about QSBS planning and see some example situations)

Challenges for QSBS Holders | QSBS Exemption

Under IRC Section 1045, Qualified Small Business Stock (QSBS) holders may utilize a “QSBS rollover” to defer taxes when selling their QSBS before meeting the five-year holding period required for the Section 1202 exclusion. This need could arise from liquidity demands, financial pressures, or favorable market conditions prompting an early sale of stock. In these cases, a QSBS rollover allows holders to defer gains by reinvesting the proceeds into another QSBS opportunity/business within 60 days, preserving potential future QSBS exemption benefits while addressing immediate financial needs.

Additionally, the $10M per issuer exclusion cap under IRC Section 1202 limits the gain that can be excluded from federal income tax when selling QSBS. For those seeking to defer gains above this cap, the QSBS rollover offers a viable solution. By reinvesting excess proceeds into new QSBS within 60 days, investors can defer gains, potentially benefiting from an additional issuer exclusion cap of $10M in the future while meeting immediate financial needs or strategic investment goals.

Common opportunities to employ QSBS rollovers may not be appealing to most investors. Options typically include reinvesting into high-risk ventures or funds to avoid paying the 23.8%+ in capital gains and NIIT taxes. Other planning solutions are often inflexible or untenable for newly-exited shareholders, and the short 60-day window to implement a reinvestment plan further complicates the process.

Get started with a QSBS rollover and partner with our expert team!

Vint Retail Partnership Program | A Rollover Partner

Through the Vint Retail Partnership Program, we work with businesses to on-ramp and run luxury online retail businesses. Our expertise is in the wine and spirits space, which happens to be an ideal sector for those looking to deploy capital via QSBS rollovers.

Most QSBS rollover opportunities have one or more of the following problems for recently-liquid QSBS holders:

  • The investment is incredibly risky (i.e. angel investments)

  • The investment has an unknown or inflexible liquidity timeline (i.e. venture funds)

  • A suitable investment opportunity can’t be identified soon enough (60 day rollover period)

Vint’s Retail Partnership Program enables:

  • An expedient business solution

  • Controlled and flexible liquidity opportunities

  • Downside risk protection and resourcing

  • An established and expert partner in Vint

  • Massive potential tax-saving opportunities via Section 1202

  • Access to a network of the top CPAs, attorneys, and advisors in the industry