QSBS Spotlight: Bootstrapped Rockerbox Exits for $85M to DoubleVerify (NYSE: DV)
A weekly series where we cover recent acquisitions, capital raises, and pending IPOs that may be Qualified Small Business Stock (QSBS) tax exemption eligible, granting investors and planners insight into real world planning opportunities using QSBS rollovers.
Imagine not paying a dime in tax on a $85M bootstrapped exit?
Rockerbox, the media measurement startup, has agreed to be acquired by DoubleVerify (NYSE: DV) in an all-cash deal valued at $85 million, plus additional equity for employees (per Axios). The transaction highlights a major QSBS tax-savings opportunity for the company’s founder (and any early angels and equity-comped employees).
Since Rockerbox was, in the words of CEO/co-founder Ron Jacobson, "relatively bootstrapped," raising only a modest amount from angel investors and an accelerator, its likely a large portion of equity ownership was retained by these early employees. With this cash exit, some may stand to benefit well beyond the $10M QSBS cap, making rollover planning essential.
For eligible shareholders, the QSBS exemption allows up to $10M—or 10 times their investment—to be excluded from federal capital gains taxes (and many states). However, those exceeding the cap can utilize a QSBS rollover (Section 1045 rollover) to defer and potentially eliminate taxes by reinvesting in another QSBS-eligible company, restarting the five-year clock on their exemption.
For founders and investors with outsized gains, this strategy is one of the most powerful tax mitigation tools available, especially for those in high-tax states like New York.
The Rockerbox acquisition is a textbook case of how bootstrapped founders can leverage QSBS for significant tax savings. With proper planning, all gains from this exit could be shielded from taxation, optimized for liquidity, and reinvested to maximize long-term wealth growth.
For more information on QSBS rollovers and how they can help to multiply the $10M exclusion limit, read more below or contact our team Program Director at brady@QSBSrollover.com, or take our eligibility quiz, here.
______________________________________
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 potentially save millions in gains tax from a stock sale.
Here are some of the questions we typically ask when having a first meeting with potential partners:
Did you recently sell or are you holding Qualified Small Business Stock?
When did you sell your stock?
Was this your first liquidity event?
Are you a founder, early employee, outside investor/angel, etc?
Are you certain that your stock met the Active Trade/Business and other requirements under Section 1202? (Outside of holding period requirements)
What is your intended rollover amount?
How long did you hold your initial stock?
(Read more about QSBS planning and see some example situations)
