Whetstone Capital Advisors Launches Proxy Fight at OptimizeRX

by | Mar 11, 2025

Whetstone Capital Advisors, a value-focused investment firm based in Mission Woods, Kansas, has launched a proxy fight at OptimizeRX (NASDAQ: OPRX) in an effort to drive strategic changes at the company. The firm, known for its concentrated long positions and research-driven investment approach, filed its first Schedule 13D on February 3, 2025, alongside a letter urging the board to explore strategic alternatives to maximize shareholder value.

Whetstone Nominates Carlson and Fein to the Board

On March 6, 2025, Whetstone formally notified OptimizeRX of its intent to nominate Andrew Carlson, an Investment Partner at Whetstone, and John Fein for election to the company’s board.

Boardroom Alpha’s analysis highlights several governance and performance concerns that may strengthen Whetstone’s case. OptimizeRX has suffered a 73% stock decline over the past year and a 10% decline over the past five years, significantly underperforming the S&P 500. Additionally, the company is currently searching for a permanent CEO after ex-CEO William Febbo stepped down at the end of December 2024 after 8 years. Governance concerns include a board with consistently low shareholder support, failing say-on-pay votes for the past 3 years, multiple late filings and significant stock drops, adding to questions on execution and strategic direction.

Whetstone’s Investment in OptimizeRX & Portfolio Strategy

Whetstone, founded by David Atterbury in 2010 and run out of Kansas, employs a rigorous, research-intensive investment strategy, typically holding 15-20 high-conviction positions. The firm specializes in software, payments, internet technology, and media, aligning well with OptimizeRX’s role in healthcare technology.

According to Whetstone’s latest 13-F filing as of February 12, 2025, beyond OptimizeRX, Whetstone also recently added DraftKings (DKNG) valued at $4.7 million and Option Care Health (OPCH) at $0.8 million. The firm also increased its holdings in Dave Inc. (DAVE) and Thryv Holdings (THRY) while exiting positions in DexCom (DXCM), Eventbrite (EB), and Nerdy (NRDY).

Implications for OptimizeRX Shareholders

Whetstone has become OptimizeRX’s top institutional shareholder and will likely win its desired board seats, if not a strategic shift even in advance of gaining those seats. It’s more unlikely that longer-term shareholders will see enough benefit from those changes to recoup their significant losses.

Recent Analysis

Daily SPAC Update – August 27, 2025

Another Crytpo SPAC Deal as Trump + Crypto.com Team Up. M3-Brigade IPOs Another SPAC. Calm Digital IPOs for $200M. Dynamix Ticker Change Pre-DeSPAC.

Daily SPAC Update – August 26, 2025

Alchemy + Cartiga and Inflection Point III + A1R WATER Deals Announced. Southport + Angel Studios Deal Approved. New Deal Deck for Ares II and Kodiak.

Daily SPAC Update – August 25, 2025

Southport Acquisition + Angel Studios Deal Vote. FG Merger II + Boxable Investor Presentation. DECA Securities Purchase Agreement. AParadise Acquisition Separate Trading.

AstroNova Settles Proxy Fight with Askeladden Capital

AstroNova and Askeladden Capital reached a cooperation agreement on August 21, 2025, following a contested proxy fight. The deal adds a new independent director, sets standstill provisions, and signals governance changes after years of underperformance.

Subscribe to Boardroom Alpha Newsletters

Subscribe to Boardroom Alpha's research to receive the latest on governance, SPACs, and people.

Disclaimer

The opinions and information contained herein have been obtained or derived from sources believed to be reliable, but Boardroom Alpha cannot guarantee its accuracy and completeness, and that of the opinions based thereon. 

This report contains opinions and is provided for informational purposes only – it does not constitute investment, legal or tax advice. You should not rely solely upon the research herein for purposes of transacting securities or other investments, and you are encouraged to conduct your own research and due diligence, and to seek the advice of a qualified securities professional before you make any investment.  

None of the information contained in this report constitutes, or is intended to constitute a recommendation by Boardroom Alpha of any particular security or trading strategy or a determination by BA that any security or trading strategy is suitable for any specific person. To the extent any of the information contained herein may be deemed to be investment advice, such information is impersonal and not tailored to the investment needs of any specific person.  

No representation or warranty, expressed or implied, is made on behalf of Boardroom Alpha as to the accuracy or completeness of the information contained herein. Boardroom Alpha does not accept any liability for any direct, indirect or consequential loss or damage suffered by any person as a result of relying on all or any part of this research and any liability is expressly disclaimed.