Rush Street Interactive CEO Sells $3 Million as Stock Gains 38% in 12 Months

On Friday, Richard Todd Schwartz, the CEO of Rush Street Interactive (NYSE:RSI), reported the sale of 158,335 shares -- comprising both direct and indirect holdings -- following the exchange of partnership units for Class A Common Stock, as disclosed in the SEC Form 4 filing.

Transaction summary

Transaction value based on SEC Form 4 weighted average purchase price ($19.22); post-transaction value based on Friday's market close ($19.26).

Key questions

• How did the transaction affect Schwartz's ownership structure?
  Schwartz reported direct ownership of 1.2 million Class A common shares and 5.33 million Class V common shares after the transaction, along with indirect holdings.
• What derivative mechanics were involved in this disposal?
  This filing reflects a derivative transaction involving the conversion of a derivative security into Class A Common Stock, which was then sold.
• How does the sale size compare to Schwartz's historical transaction pattern?
  The 158,335 shares sold is below the recent median sale of 193,905 shares, but the percentage of pre-transaction holdings impacted (11.7%) is above the recent median of 8.34%, likely due to the reduced remaining capacity.
• What is the post-transaction liquidity and potential future activity?
  Schwartz retains approximately 1.2 million directly held Class A shares valued at $23.0 million.

Company overview

Company snapshot

• Rush Street Interactive offers real-money online casino gaming, online and retail sports betting, and social gaming services across the United States and Latin America.
• The company generates revenue primarily from gaming operations under brands such as BetRivers.com, PlaySugarHouse.com, and RushBet.co, leveraging proprietary technology and partnerships with land-based casinos.
• It targets adult consumers seeking regulated online casino and sports betting experiences, with a focus on both U.S. and Latin American markets.

Rush Street Interactive is a leading online casino and sports betting operator with a growing presence in the Americas. The company leverages a multi-brand strategy and proprietary technology to capture share in regulated gaming markets. Its focus on customer experience and diversified product suite positions it competitively within the rapidly expanding digital gambling industry.

What this transaction means for investors

Rush Street Interactive has been executing well, with shares up roughly 38% over the past year, comfortably ahead of the S&P 500’s 18% gain. That strength has been backed by operating results. In the third quarter, the company posted record revenue of $277.9 million, up 20% year over year, alongside net income of $14.8 million and adjusted EBITDA of $36.0 million, a 54% increase from the prior year. Management also raised full-year guidance, now calling for about $1.11 billion in revenue and roughly $150 million in adjusted EBITDA at the midpoint.

Against that backdrop, the recent share sale by CEO Richard Todd Schwartz doesn’t seem to suggest a shift in conviction. The transaction followed the exchange of partnership units into Class A shares and still leaves Schwartz with approximately 1.2 million directly held Class A shares worth about $23 million, plus significant Class V ownership.

Ultimately, insider monetization amid strong execution and raised guidance is not inherently bearish. What matters is that Rush Street continues to scale profitably in regulated markets, with improving margins and sustained user growth supporting the stock’s longer-term narrative.

Glossary

Disposition: The act of selling or otherwise transferring ownership of a security.

Indirect holdings: Securities owned through an intermediary, such as a trust or partnership, rather than held directly.

Affiliated trusts: Trusts connected to an individual, often used for estate planning or indirect ownership of assets.

Derivative securities: Financial instruments whose value is based on the price of another asset, such as options or warrants.

Class A common stock: A category of common shares that may have specific voting rights or privileges compared to other classes.

Exchange of partnership units: Converting ownership interests in a partnership into shares of a corporation.

Form 4: A required SEC filing disclosing insider transactions in a company's securities.

Weighted average purchase price: The average price paid per share, weighted by the number of shares in each transaction.

Direct ownership: Securities held in an individual's own name, not through intermediaries.

Derivative transaction: A trade involving financial instruments whose value is derived from an underlying asset.

Liquidated: The process of converting an asset into cash by selling it.

TTM: The 12-month period ending with the most recent quarterly report.

Jonathan Ponciano has no position in any of the stocks mentioned. The Motley Fool has no position in any of the stocks mentioned. The Motley Fool has a disclosure policy.