TSQ Townsquare Media, Inc. Insider Trading

EVP Scott Schatz buys 980 TSQ shares at $6.61; stock up 33.8% in 30 days but down 25.4% from 52-week high.

Schatz purchased 980 shares at $6.61, bringing his holdings to 58,051 shares. The stock has rallied 33.8% over the past 30 days, though it remains 25.4% below its 52-week high of $9.28. His same-ticker trading history at TSQ shows a 3 of 4 pattern of well-timed trades at the 90-day mark, including a prior buy on 2025-11-03 that gained 4.3% over 90 days. However, this context must be weighed against Townsquare Media's fundamentals: the company posted negative net income of $-5.9M in its latest quarter, full-year results were unprofitable, and annual revenue declined 0.7%. The buy occurs in the context of a stock that has recovered sharply from recent lows but in a company with persistent profitability challenges.

EVP Schatz buys 855 TSQ shares at $6.30; holdings rise 1.6% amid -40.6% 52-week decline and unprofitable FY.

Schatz Scott, EVP of Finance Operations and Technology, purchased 855 shares of Townsquare Media at $6.30 on 2025-11-03, bringing his holdings to 54,920 shares. The transaction occurred while the stock is trading 40.6% below its 52-week high of $10.48, and the company posted negative full-year net income despite $115.4M in latest-quarter revenue. His prior trades at TSQ showed mixed results: a May 2025 buy posted a 90-day return of +6.7%, but an August 2025 buy declined -11.5% over 90 days. The current buy is modest in size relative to his existing position and occurs as the stock has fallen 6.3% over the past 90 days. Context includes a depressed valuation (P/E of 3.29) and flat revenue growth (-0.7% year-over-year), though the company remains marginally profitable on a quarterly basis.

Director Kaplan buys 10,000 TSQ shares at $6.92; stock now $6.82, down 37.7% from 52-week high.

Stephen A. Kaplan, a director of Townsquare Media, purchased 10,000 shares at $6.92 on 2025-08-22, expanding his holdings to 208.6K shares. This is his second consecutive buy in August (following a purchase on 2025-08-11), and his third open-market purchase overall at this ticker. However, his prior buy at TSQ on 2024-09-20 at a similar price level delivered a 90-day return of -7.2%, and his cross-ticker track record shows 0% win rate across 2 prior buys with an average 90-day return of -7.2%. The current price of $6.82 is now 37.7% below the 52-week high of $10.94, suggesting the stock has deteriorated significantly since his prior entry points. Townsquare's fundamentals are concerning: the company was unprofitable over its most recent full fiscal year, annual revenue growth is negative at -0.7%, and while the latest quarter showed $115.4M revenue, net income was only $1.6M. The P/E of 3.61 is suppressed by minimal earnings, not valuation attractiveness. Kaplan's repeated purchases into a declining stock with deteriorating fundamentals and a pattern of poor subsequent returns presents a contrarian signal rather than a vote of confidence.

Director Stephen A Kaplan purchases 46,509 shares of TSQ at $6.77; position grows 30.6% to 198,618 shares

Director Stephen A Kaplan purchased 46,509 shares of Townsquare Media at $6.77 on 2025-08-11, increasing his holdings by 30.6% from 152,109 to 198,618 shares. The purchase occurs in a stock trading 39.1% below its 52-week high and down 16.5% over the prior 30 days, but Kaplan's historical track record at this ticker offers limited confidence: his prior buy at TSQ on 2024-09-20 resulted in a -7.2% return over 90 days, and his cross-ticker open-market buying history shows an average 90-day return of -7.2% with a 0.00% win rate across 1 prior buy. The company faces structural headwinds—annual revenue declined 0.7% year-over-year, it posted negative full-year net income despite a latest-quarter profit of $1.6M, and the stock's severely depressed valuation (P/E of 3.69) reflects fundamental concerns that a director purchase alone does not resolve.

EVP Scott Schatz buys 743 TSQ shares at $7.05; stock down 42.7% from 52-week high, company unprofitable.

Scott Schatz, EVP of Finance Operations and Technology, purchased 743 shares of Townsquare Media on 2025-08-01 at $7.05, expanding his holdings by 1.4% to 54.1K shares. The purchase occurred as TSQ trades at -42.7% from its 52-week high of $12.08 and while the company reported a net loss of $2.0M on $98.7M in quarterly revenue. Schatz's prior trade at TSQ (a buy on 2025-05-01) delivered a 90-day return of +6.7%, and his cross-ticker track record shows 100% buy win rate over 90 days, suggesting consistent execution timing. However, the company's recent unprofitability and significant year-to-date decline temper any single-trade signal; this modest acquisition warrants monitoring relative to broader operational trends at the company.

EVP Finance Scott Schatz buys 788 TSQ shares at $6.57; stock down -45.1% from 52-week high, now $7.03

EVP Finance Operations and Technology Scott Schatz purchased 788 shares of Townsquare Media at $6.57 on 2025-05-01, raising his holdings to 51,322 shares. The purchase occurred as TSQ trades at $7.03, representing a -45.1% decline from its 52-week high of $12.80 and a -14.4% drop over the prior 30 days. Schatz's cross-ticker track record shows 1 prior sell with a 100.00% well-timed rate at the 90-day mark, though that outcome came on a different ticker. At TSQ specifically, Schatz executed 1 prior trade—a 2024-04-04 sale that was well-timed (the stock subsequently declined -12.6% over 90 days). The company posted net income of $10,847,000 in the latest quarter on revenue of $115,311,000, but reported negative full-year results in its most recent fiscal year, and annual revenue growth stands at -0.7%. The modest transaction size ($5,177.16) and the company's unprofitable fiscal-year backdrop limit the evidential weight of this buy relative to the broader stock price deterioration.

CEO Wilson Bill purchased 165 shares of TSQ at avg $9.37, marking first buy after prior sale; stock down 30.7% from 52-week high

Wilson Bill, CEO of Townsquare Media, executed 2 separate purchases totaling 165 shares for $1,545.63 on 2024-12-27 at an average price of $9.37, starting a new position from zero prior holdings. This purchase occurs in a deteriorated market context: the stock is trading 30.7% below its 52-week high of $13.11, down 10.0% over 30 days and 12.2% over 90 days. The company's fundamentals show recent strain, with annual revenue growth of -1.9% and a full-year fiscal result that was unprofitable, though the latest quarter generated $10.8M in net income on $115.3M revenue. The insider's cross-ticker track record shows 1 prior sell (his only open-market activity elsewhere) that was well-timed at the 90-day mark, indicating a history of selling before downturns—a pattern that provides no direct read on his buy discipline at this ticker. At TSQ specifically, his only prior transaction was a sale on 2024-04-04 that returned -12.6% over 90 days (well-timed against a declining stock). The timing and magnitude of this new buy—in a material sector downturn after prior profitable exit—invites examination of whether it reflects opportunistic accumulation or scheduled activity.

Director Kaplan buys 50,000 TSQ shares at $10.41; stock now at $10.29, company unprofitable with -$49.2M net income.

Director Stephen A Kaplan purchased 50,000 shares of Townsquare Media at $10.41 on 2024-09-20, increasing his holdings from 87,808 to 137,808 shares—a 56.9% increase in position size. The timing comes as the stock has declined 21.5% from its 52-week high of $13.11 and currently trades at $10.29, near the transaction price. Notably, the company reported a net loss of $-49.2M in its most recent fiscal year, with annual revenue declining 1.9% year-over-year. This purchase by a director into a financially distressed company with negative earnings and declining growth warrants examination of the company's underlying business trajectory and restructuring efforts.