Whetstone Capital Advisors Launches Proxy Fight at OptimizeRX

by BA Research | 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.

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