Form 4: Airship AI Director Plans Future Stock Purchase

Airship AI Holdings Director Louis Lebedin has filed a Form 4 indicating a future acquisition of 50,000 common shares at $3.18 per share on November 18, 2025, under a Rule 10b5-1 plan.

Summary

• Director Louis Lebedin plans to acquire 50,000 shares of Airship AI Holdings, Inc. common stock at a price of $3.18 per share on November 18, 2025.
• Following this planned transaction, Lebedin will directly beneficially own 100,000 shares of common stock.
• Lebedin holds 200,000 Non-Qualified Stock Options (NQSOs) with an exercise price of $1.65, expiring on March 3, 2029.
• These NQSOs vest quarterly over a four-year period, with 12,500 options vesting on March 31st, June 30th, September 30th, and December 31st each year.
• Additionally, Lebedin holds 50,000 options with an exercise price of $4.25, expiring on September 3, 2035.
• These 50,000 options also vest quarterly over a four-year period.
• The reported common stock transaction is made pursuant to a Rule 10b5-1 plan, indicating a pre-arranged purchase.

Sentiment

Score: 7

Explanation: The planned future purchase of a significant block of shares by a director, coupled with substantial option holdings, indicates strong insider confidence, which is a positive signal for the company's outlook.

Positives

• The planned future purchase of 50,000 common shares by a director at $3.18 per share signals strong insider confidence in the company's future prospects.
• Significant holdings of both common stock and derivative securities (250,000 options in total) align the director's interests with long-term shareholder value.

Risks

• The value of the acquired shares and options is subject to market fluctuations and the company's performance.
• The vesting of the stock options is contingent on continued service to the company over the four-year vesting period.

Future Outlook

Director Louis Lebedin's planned future stock purchase and substantial unvested option holdings indicate a long-term commitment and belief in the company's future growth. The vesting schedules for the options suggest a continued alignment of interests over the next four years.

Industry Context

Insider buying, particularly by a director, is often viewed by the market as a positive signal, suggesting that those with intimate knowledge of the company believe its stock is undervalued or has strong future prospects. This planned purchase could be interpreted as a vote of confidence in Airship AI Holdings' strategic direction and operational performance within its industry.

Related Party Transactions

• Director Louis Lebedin's planned acquisition of 50,000 common shares from Airship AI Holdings, Inc. on November 18, 2025.
• The granting of 200,000 Non-Qualified Stock Options and 50,000 additional options to Director Louis Lebedin.

Stakeholder Impact

• Shareholders may view the director's planned purchase as a positive indicator of future company performance and management's belief in the stock's value.
• The increased direct beneficial ownership by a director aligns management's interests more closely with those of other shareholders.

Next Steps

• The planned acquisition of 50,000 common shares by Director Louis Lebedin is scheduled for November 18, 2025.
• The vesting of 200,000 NQSOs and 50,000 options will continue quarterly over a four-year period.

Key Dates

Recommendation

The planned future purchase of a significant block of common stock by a director, executed under a Rule 10b5-1 plan, signals strong insider confidence in Airship AI Holdings' future prospects. This proactive investment, coupled with substantial existing option holdings, suggests management believes the stock is undervalued or poised for growth, making it an attractive signal for potential investors.

Keywords

Airship AI Holdings, AISP, Insider Trading, Stock Purchase, Director, Options, Common Stock, SEC Form 4, Rule 10b5-1