QSBS Before 5 Years or Beyond $10M

Defer or pay no taxes on startup stock sale gains with Qualified Small Business Stock Rollovers - regardless of hold period or exit size.

Defer Your Tax Bill, Exclude Your Gains

5-Year Hold Period: If you sold your stock before the 5-year hold required by the IRS for QSBS exclusion, a rollover is your only option for deferring, and later avoiding, a large gains tax bill.

$10M Exclusion Cap*: If you had a large exit and your gain exceeded the $10M exclusion cap for QSBS, a rollover can expand your QSBS eligibility with more liquidity and control than other common planning strategies such as Trust Stacking.

*Or 10x adjusted gross basis in the stock.

Founders, employees, and investors can all benefit from QSBS rollovers

  • Founder Selling Shares

    Founders may reach a point of liquidity through the sale of stock in a number of ways. Whether you’ve taken money off the table via a secondary sale through a Series B, sold on a private exchange, or had your stock purchased by another outside investor, we can help you preserve your QSBS benefit.

    This is Me

  • Secondary Sale of Stock

    Especially during later or larger rounds of funding, early investors and founders may have the opportunity to sell stock. Whether a secondary sale happens before 5 years, or the gain amounts to more than $10M, a rollover can be a great option.

    Learn More

  • LP with a Distribution

    As a limited partner, receiving a distribution before the 5-year QSBS holding period can raise questions about preserving your tax benefits. Whether your fund’s early exit stems from an acquisition, tender offer, or secondary sale, we can help you navigate QSBS rollovers to ensure you maximize flexibility.

    This is Me

  • Mergers and Acquisitions

    Exiting through a company sale or M&A before the 5-year QSBS holding period—or when your individual gain exceeds $10M—doesn’t mean losing out on QSBS benefits. By utilizing a QSBS rollover, you can potentially save up to 100% of your tax bill. Let us help you navigate this critical step to maximize your exit's value, regardless of stock holding period or exit size.

    Learn More

  • Employee Selling Shares

    Early employees often face unique opportunities to realize the value of their shares through tender offers, secondary sales, or other liquidity events. Whether you're navigating a company buyback, a private transaction, or an offer from an external investor, we can help you maximize and preserve your QSBS advantage.

    This is Me

  • Investor With a Quick Exit

    As an angel investor, exiting early can unlock liquidity but may create challenges in preserving QSBS tax benefits. Whether your shares were sold in a tender offer, acquisition, or other early liquidity event, we can guide you through QSBS rollovers to help you maintain your tax advantage and maximize your return.

    This is Me

  • Private Company Near IPO

    An upcoming IPO can open the door to significant liquidity opportunities, but it’s also the perfect time to plan for preserving your QSBS benefits. Whether you're considering a partial sale, tender offer, public market sale, or other pre or post-IPO exit strategies, we can help you navigate QSBS rollovers and tax planning to ensure you maximize your gains while staying tax-efficient.

    Learn More

Keeping Gains in The Hands of Startup Founders and Investors

The founders, early employees, and investors who champion growth and innovation in our startup ecosystem deserve more value at exit.

While many shareholders are able to take advantage of some QSBS, very few realize it’s full potential, likely leaving $5B+ on the table every year.

Rollovers allow gain holders to extend and expand more of their QSBS eligibility even when exiting before 5 years or for more than $10M.

Less Tax Means More Cash in Your Pocket

QSBS Rollovers can net you up to 55% more cash from your stock sale and help you retain the tax benefits you thought were lost by selling early or “making too much”.

Our team is prepared with the expertise and resources to help you navigate every kind of QSBS-related issue. Whether you’re confident that your stock qualifies for the QSBS exclusion, aren’t sure how much, or you don’t even know if your stock is eligible, we can help!

Articles and Other Resources