Townsquare Media, Inc. (TSQ) — Insider Trading

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This analysis covers the filing from 2026-01-16. New 10-K, 10-Q and 8-K filings are analyzed the moment they are released — exclusively in the app.

Earlier Insider Trading filings

Filed: 2026-01-16
  • Reporting person Gary L. Ginsberg has acquired 24,030 shares of Townsquare Media, Inc. (TSQ) Class A common stock, increasing his direct ownership to 129,938 shares.
  • The acquisition of these shares represents Ginsberg's ongoing commitment and alignment with Townsquare Media as a director of the company.
  • The transaction price of $5.41 per share suggests Ginsberg views the current stock price as attractive for investment.
Filed: 2026-01-16
  • Stephen A. Kaplan, a director of Townsquare Media, Inc. (TSQ), acquired 24,030 shares of the company's Class A common stock, increasing his direct ownership to 232,648 shares.
  • The acquisition of shares by a director suggests their confidence in the company's future performance and aligns their interests with those of other shareholders.
  • The transaction price of $5.41 per share represents a potential opportunity for investors, as it is below the current market price of the stock.
Filed: 2026-01-16
  • David Lebow, a director at Townsquare Media, Inc. (TSQ), acquired 24,030 shares of the company's Class A common stock on January 14, 2026 at a price of $5.41 per share.
  • Lebow's total beneficial ownership of TSQ shares increased to 129,920, including 95,890 unrestricted shares and 10,000 fully vested stock options.
  • This insider purchase suggests Lebow is confident in the company's future prospects and aligns his interests with those of other shareholders.
Filed: 2026-01-16
  • The reporting person, Gary D. Way, acquired 24,030 shares of Townsquare Media, Inc. (TSQ) Class A common stock on January 14, 2026, increasing his direct ownership to 50,712 shares.
  • This transaction appears to be a grant of restricted stock to the reporting person in respect of his services on the company's Board of Directors, with the shares vesting fully on the first anniversary of the grant.
  • The reporting person's increased ownership, combined with the vesting structure, suggests he has a long-term investment outlook and confidence in Townsquare Media's future performance.
Filed: 2026-01-16
  • The CEO Bill Wilson acquired a significant amount of Class A common units in Townsquare Media, Inc. through restricted stock units (RSUs), indicating his confidence in the company's future performance.
  • The RSUs include both time-based and performance-based vesting conditions, aligning the CEO's incentives with long-term shareholder value creation.
  • The insider buying, along with the large number of shares and options already beneficially owned by the CEO, suggests strong management alignment and commitment to the company's growth.
Filed: 2026-01-16
  • The reporting person, Stuart B. Rosenstein, an EVP and CFO of Townsquare Media, Inc. (TSQ), has acquired a significant amount of Class A common units and Class B common stock through restricted stock units and options, indicating increased ownership and alignment with shareholders.
  • The performance-based restricted stock units granted to Rosenstein are tied to specific stock price targets, which could incentivize him to drive the company's performance and shareholder value creation.
  • Rosenstein's total beneficial ownership of Class A common units and Class B common stock, including vested and unvested equity awards, represents a sizable position in the company, suggesting a strong commitment to Townsquare Media's long-term success.
Filed: 2026-01-16
  • Insider Erik Hellum acquired a significant number of Townsquare Media (TSQ) shares, including 92,421 time-based restricted stock units and 189,368 performance-based restricted stock units, indicating his confidence in the company's future performance.
  • The performance-based restricted stock units are tied to the achievement of specific stock price targets, suggesting management believes the company can generate substantial shareholder value going forward.
  • Hellum's total beneficial ownership in Townsquare Media now stands at over 1 million shares, further aligning his interests with those of other shareholders.
Filed: 2025-12-31
  • The COO, Erik Hellum, sold 5,693 shares of Class A common stock on December 29, 2025, likely to cover tax withholding requirements following the vesting of restricted stock units.
  • Hellum continues to beneficially own a significant stake of 754,798 shares, including 242,127 unvested RSUs and 402,194 vested stock options, indicating his ongoing commitment to the company.
  • The transaction represents a small fraction of Hellum's overall holdings, suggesting the sale was a routine personal financial activity rather than a broader indication of his outlook on the company.

Important Information

AI-generated analysis is for informational purposes only. Always read original SEC filings and consult with qualified professionals before making investment decisions.