Form 4: TLSS CEO Acquires Convertible Preferred Stock in Settlement

Transportation & Logistics Systems, Inc. CEO Sebastian Giordano acquired 10,007 shares of Series J Senior Convertible Preferred Stock as part of a settlement agreement.

Summary

• Sebastian Giordano, Chief Executive Officer and Director of Transportation & Logistics Systems, Inc. (TLSS), acquired 10,007 shares of Series J Senior Convertible Preferred Stock.
• The acquisition took place on December 15, 2025, and was made pursuant to a settlement agreement between Mr. Giordano and the Issuer, resolving certain liabilities.
• The Series J Senior Convertible Preferred Stock is convertible at any time, at the holder's election, at an initial conversion price of $0.001 per share of common stock.
• This preferred stock is perpetual and does not have an expiration date.
• A contractual limitation prevents Mr. Giordano from converting Series J preferred stock if, after conversion, his beneficial ownership would exceed 4.99% of the outstanding common stock.
• Following this transaction, Mr. Giordano beneficially owns 15,332 shares of derivative securities, which underlie 1,000,700,000 shares of common stock.

Sentiment

Score: 5

Explanation: Neutral. The settlement of liabilities is a positive, but the issuance of convertible preferred stock with a reported 1,000,700,000 underlying common shares introduces significant future dilution risk for existing shareholders. The lack of detail on the 'certain liabilities' also adds uncertainty.

Positives

• The company has settled certain liabilities with its CEO, which can resolve outstanding financial or operational issues.
• The CEO's increased beneficial ownership aligns his interests more closely with those of the company's shareholders.

Negatives

• The issuance of Series J Senior Convertible Preferred Stock, which underlies 1,000,700,000 common shares, presents a significant potential for future dilution of existing common stock shareholders.
• The specific nature of the 'certain liabilities' settled is not detailed, which could obscure underlying issues.

Risks

• Potential for substantial dilution of common stock if the Series J Senior Convertible Preferred Stock is converted, given the reported 1,000,700,000 underlying common shares, which could negatively impact per-share value.
• The 4.99% beneficial ownership cap on conversion limits immediate dilution but the long-term potential for dilution remains.
• Lack of transparency regarding the 'certain liabilities' settled could indicate undisclosed past financial or operational challenges.

Future Outlook

The filing does not provide explicit forward-looking statements or guidance beyond the nature of the convertible preferred stock and its conversion terms.

Management Comments

• Sebastian Giordano acquired the Series J Senior Convertible Preferred Stock pursuant to a settlement agreement between himself and the Issuer, dated December 15, 2025, in exchange for the settlement of certain liabilities.

Industry Context

This Form 4 filing is specific to an insider transaction and does not provide broader industry context or trends. However, the issuance of convertible preferred stock to settle liabilities can be a mechanism used by companies, particularly in the transportation and logistics sector, to manage debt or other obligations without immediate cash outflow, potentially indicating financial restructuring or a need to conserve cash.

Related Party Transactions

• Sebastian Giordano, as CEO and Director, is a related party to Transportation & Logistics Systems, Inc. The acquisition of Series J Senior Convertible Preferred Stock by Giordano from the Issuer as part of a settlement agreement constitutes a related party transaction.

Stakeholder Impact

• **Shareholders:** Potential for significant dilution of common stock if the Series J preferred stock is converted, given the large number of underlying common shares reported. This could negatively impact per-share value.
• **Company:** Resolution of 'certain liabilities' through a non-cash settlement, which could improve the company's financial position by removing obligations without immediate cash outflow.

Next Steps

• The Series J preferred stock is convertible at the holder's election at any time, subject to the 4.99% beneficial ownership limitation.

Key Dates

Recommendation

While the settlement of liabilities is a positive step for the company, the issuance of Series J Senior Convertible Preferred Stock to the CEO, with its significant potential for dilution (1,000,700,000 common shares underlying the derivative securities beneficially owned), introduces substantial uncertainty and risk for existing common shareholders. The explicit statement of 1,000,700,000 underlying common shares, despite a stated conversion price of $0.001 per common share, creates a significant discrepancy that warrants caution. Investors should hold and monitor for further clarification on the conversion terms and the impact of potential dilution before making further investment decisions.

Keywords

Transportation & Logistics Systems, TLSS, Sebastian Giordano, Form 4, Insider Transaction, Convertible Preferred Stock, Settlement Agreement, CEO Stock Acquisition, Dilution Risk, Corporate Governance