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Equity And Debt Instruments

Understand Your Options Regarding Equity And Debt Instruments

An equity instrument can be titled common stock, preferred stock, LLC membership interest or LLC membership unit, warrant or option, each having a particular meaning and typically not interchangeable. Here, we discuss the various types of equity instruments.

LLC Membership Interest Or LLC Membership Unit

An LLC membership interest or LLC membership unit refers to the general term encompassing equity ownership in a limited liability company (LLC). Within the framework of an operating agreement, LLC members define various classes of equity and specify the associated rights and preferences for each class. The structure of an LLC is highly adaptable, allowing for diverse sets of rights and preferences—both financial and non-financial—for different classes of equity, akin to those available for common or preferred stock.

Common Stock


Common stockholders occupy a subordinate position compared to preferred stockholders concerning the entitlement to receive dividends. In the hierarchy of rights, common stockholders are behind both preferred stockholders and creditors in their claims to receive payments in the event of liquidation. Common stock is the most prevalent form of equity security. While common stock typically carries voting rights, especially in publicly traded equity markets, it can be categorized as either voting or non-voting. Common stock lacks fixed dividends or specific rights and preferences, distinguishing it from preferred stock.

Preferred Stock


Preferred stock is a widely utilized investment instrument owing to its versatility. It can be structured to encompass a spectrum of characteristics from both equity and debt, both in financial and non-financial aspects. The flexibility of preferred stock allows it to be tailored to meet the specific requirements of a given transaction. The following outlines various features that can be incorporated into a preferred stock designation:

  1. Dividend Preference: Preferred stockholders may have priority over common stockholders in receiving dividends.

  2. Convertible or Non-Convertible: Preferred stock can be designed to be convertible into common stock or remain non-convertible.

  3. Cumulative or Non-Cumulative Dividends: Accumulated unpaid dividends may be carried forward for payment in subsequent periods for cumulative preferred stock.

  4. Redemption Rights: The issuer may have the option to redeem preferred stock after a specified period.

  5. Voting Rights: While common stock is typically associated with voting rights, preferred stock may or may not carry voting privileges.

  6. Participation Rights: Preferred stockholders may have the right to participate in any remaining proceeds after the common stockholders receive their share.

  7. Liquidation Preference: In the event of liquidation, preferred stockholders may have a specified claim on the company's assets.

  8. Adjustment Provisions: Preferred stock terms may include adjustments based on certain events, such as stock splits or mergers.

  9. Callable or Non-Callable: The issuer may have the right to call or redeem the preferred stock under certain conditions.

  10. Exchangeable Preferred Stock: Preferred stock can sometimes be exchangeable for shares of another company.

The flexibility in structuring preferred stock allows for a wide range of possibilities, making it a versatile investment choice.

Dividends

A dividend in the context of preferred stock represents a fixed amount agreed upon to be paid per share. This amount can be determined based on either the face value of the preferred stock or the price paid for the preferred stock, which often coincide. Dividends can take various forms, including:

  1. Return on Investment: Expressed as a fixed percentage (e.g., 8% per annum) of the face value or purchase price of the preferred stock.

  2. Return of Investment: Involves returning a portion of the principal investment, such as 25% of all net profits until the principal investment is fully repaid.

  3. Combination of Both: Dividends can be structured as a combination of a fixed return on investment and a return of investment.

Despite the similarities between dividends and debt instruments, legal constraints may hinder dividend payments. Creditors typically have priority over equity holders, and state corporate laws often dictate that an issuer must be solvent (able to meet its obligations to creditors) before distributing dividends. This legal requirement ensures that the issuer can fulfill its financial obligations before making distributions to equity holders.

Therefore, even if an issuer has a contractual obligation to pay dividends, its ability to do so may be constrained by legal or financial considerations. It's crucial to consider these factors when evaluating the feasibility of dividend payments.

The payment of dividends may or may not occur as initially promised, and the treatment of dividends can vary:

  1. Accrual and Cumulation: In some cases, if a dividend is not paid as scheduled, it may accrue and cumulate. This means that each missed dividend is owed to the preferred shareholder and must be paid in the future.

  2. Non-Accrual: Alternatively, dividends may not accrue, and if a dividend is missed, it is not carried forward to future periods. The expectation is that the shareholder did not receive the dividend for the specific period but may receive it in subsequent periods.

Dividend payments can be structured to occur at various intervals, but they are commonly arranged to be paid no more frequently than quarterly, and often annually.

Additionally, dividends on preferred stock typically hold a preferential status. This means that any accrued dividends on preferred stock must be fully paid before any dividends can be distributed to common stockholders or holders of other junior securities. The preferential treatment ensures that preferred stockholders receive their owed dividends before other shareholders or security holders receive any distributions. This feature enhances the attractiveness of preferred stock to investors seeking a stable and predictable income stream.

Voting Rights

Preferred stock can be set up to establish any level of voting rights from no voting rights at all, voting rights on certain matters (sole vote on at least one board seat; voting rights as to the disposition of a particular asset but otherwise none), or super-voting rights (such as 10,000 to 1 or 51% of all votes).

Liquidation Preferences

A liquidation preference refers to the right of preferred stockholders to receive a distribution of funds or assets in the event of a liquidation or sale of the company (Issuer). While creditors typically have precedence over equity holders in liquidation scenarios, preferred stock can be structured in a manner similar to a debt instrument. This structure allows the liquidation preference of preferred stock to be secured by specific assets, giving preferred stockholders priority over general unsecured creditors concerning those particular assets.

In addition to prioritizing preferred stockholders over common stockholders and holders of other junior equities, the liquidation preference is often defined as an amount per share. This amount is usually tied to the initial investment plus any accrued and unpaid dividends.

Preferred stockholders may also have the opportunity to participate in liquidation profits in addition to the liquidation preference. For instance:

  1. Participation with Profit Share: The preferred stockholder may receive the entire investment amount back, along with all accrued and unpaid dividends, plus a percentage (e.g., 30%) of the profits from the sale of the company Issuer.

  2. Participating Liquidation Preference: Alternatively, the preferred stockholder may receive the full investment amount, along with accrued and unpaid dividends, and then participate pro rata with common stockholders on any remaining proceeds. This is known as a participating liquidation preference.

These structures provide preferred stockholders with a level of protection and a defined financial benefit in the event of a liquidation or sale, contributing to the appeal of preferred stock as an investment.

Conversion Or Exchange Rights

A conversion or exchange right grants the holder the ability to convert or exchange their existing securities into a different form, typically common stock. Here are additional details about conversion rights:

  1. Conversion Price: The conversion right includes a conversion price, which can be determined using various mathematical formulas. Examples include a discount to the market price (e.g., 75% of the average 7-day trading price immediately before conversion), a fixed price per share (e.g., preferred stock with a face value of $5.00 converts into five shares of common stock, making it $1.00 per share of common stock), or a valuation-based approach (conversion at a company valuation of $30,000,000).

  2. Optionality for Stockholder: Generally, conversion rights are at the option of the stockholder, meaning the stockholder can choose to exercise the conversion. However, issuers may also retain conversion rights, often triggered by specific events, such as a firm commitment underwriting for a significant IPO.

  3. Establishment of Timing: The timing of conversion rights must be defined, indicating when conversion can occur. This could be at any time after issuance, within a specified timeframe (e.g., between months 12 and 24), or within a certain period following a significant financial event (e.g., within 90 days of securing a firm commitment for financing exceeding $10,000,000).

  4. Whole or Partial Conversion: Conversion rights often specify whether they can be exercised in whole or in part. For public companies, there are often limits set to ensure that the conversion does not result in the holder owning more than a certain percentage (e.g., 4.99%) of the outstanding common stock at the time of conversion.

Understanding and carefully defining these aspects of conversion rights are crucial in structuring agreements and providing clarity to both issuers and stockholders regarding the conditions, timing, and limitations of conversion.

Redemption/Put Rights

A redemption right in the form of a put right is the right of the Holder to require the Issuer to redeem the preferred stock investment (to “put” the preferred stock back to the Issuer); the redemption price is generally the face value of the preferred stock or investment plus any accrued and unpaid dividends; redemption rights generally kick in after a certain period (five years) and provide an exit strategy for a preferred stock investor.

Redemption/Call Rights

A redemption right in favor of the Issuer is a call option (the Issuer can “call” back the preferred stock); generally, when the redemption right is in the form of a call, a premium is placed on the redemption price (for example, 125% of face value plus any accrued and unpaid dividends or a pro-rata share of 2.5 times EBITDA).

Anti-Dilution Protection

Anti-dilution protection protects the investor from a decline in the value of their investment due to future issuances at a lower valuation. Generally, the Issuer agrees to issue additional securities to the Holder, without further consideration, if a future issuance is made at a lower valuation, such as to maintain the investor’s overall value of the investment; an anti-dilution provision can also be as to specific percent ownership (Holder will never own below 10% of the total issued capital of the Issuer).

Registration Rights

Registration rights refer to SEC registration rights and can include demand registration rights (the Holder can demand that the Issuer register their equity securities) or piggyback registration rights (if the Issuer is registering other securities, it will include the Holder’s securities).

Transfer Restrictions

Preferred stock can be subject to transfer restrictions, either in the preferred stock instrument itself or separately in a shareholder’s or other contractual agreement; transfer restrictions usually take the form of a right of first refusal in favor of the Issuer or other security holders.

Co-Sale Or Tag Along Rights

Co-sale or tag-along rights are rights of Holders to participate in certain stock sales by management or other key stockholders.

Drag Along Rights

Drag-along rights are the rights of the Holder to require certain management or other key stockholders to participate in a stock sale by the Holder.

Other Non-Financial Covenants

Preferred stock, whether stipulated in the instrument itself or outlined in a separate shareholder or contractual agreement, can encompass a wide range of non-financial covenants. Some of the most prevalent non-financial covenants include:

  1. Board Representation: Preferred stockholders often have the right to appoint one or more individuals to the Board of Directors, allowing them to exert influence over management and operational decisions.

  2. Management Control: The ability to assert control over management and operations, beyond board representation, may be granted to preferred stockholders.

  3. Prohibitions on Related Party Transactions: Restrictions may be imposed on transactions involving related parties to ensure fairness and prevent conflicts of interest.

  4. Information Delivery Requirements: Preferred stockholders may have the right to receive specific information, ensuring transparency about the company's performance and operations.

  5. Noncompete Agreements: The company may agree not to engage in specific competitive activities, protecting the interests of the preferred stockholder.

  6. Confidentiality Agreements: Agreements to maintain the confidentiality of certain information may be included to safeguard proprietary or sensitive data.

  7. Limitations on Management Compensation: Restrictions on the amount and structure of management compensation may be established to align with the interests of preferred stockholders.

  8. Restrictions on Capital Transactions: Limitations on future capital transactions, such as reverse or forward stock splits, may be outlined to protect the preferred stockholder's interests.

  9. Prohibitions on Sale of Vital Assets or Intellectual Property: Restrictions may be placed on the sale of crucial assets or intellectual property rights to maintain the company's core value.

In essence, non-financial covenants can encompass any rights that the preferred stockholder negotiates for, providing a comprehensive framework for their involvement in the company's governance and strategic decisions.

In addition to non-financial covenants, options and warrants represent another financial instrument. An option or warrant grants the holder the right to purchase equity, usually common stock, at a predetermined price within a specified timeframe. This mechanism allows investors to benefit from potential future appreciation in the company's value.

Debt Instruments
The terms "promissory note," "note," or "debenture" are often used interchangeably to refer to a debt instrument. This instrument may or may not be convertible into equity. Conversion in this context means that instead of receiving cash, the holder accepts an equity instrument, either in whole or in part, as payment for the debt obligation.

The essential elements of a debt instrument include:

  1. Amount: Specifies the monetary value of the debt.

  2. Term: Indicates when the debt becomes due. The due date can be a specified date, on demand by the holder, upon the occurrence of certain events, or tied to milestones.

  3. Interest Rate: States the rate of interest charged on the debt. It may also specify whether the interest is compounded.

  4. Transferability or Assignability: Defines whether one or both parties can assign their rights and interests in the debt instrument to a third party.

  5. Secured or Unsecured: Specifies whether the debt is secured by collateral, such as real or personal property, or other financial instruments (often referred to as a pledge agreement).

  6. Guaranty: Addresses whether a third party, like a principal of the issuer, is guaranteeing the obligations in the debt instrument.

  7. Prepayment Rights: Outlines whether the debt can be prepaid in whole or in part.

  8. Payment Preferences/Subordination/Senior Debt: Describes contractual preferences for payment, subordination, or seniority in relation to other debts.

  9. Convertibility: Addresses whether the debt can be converted into an equity instrument, specifying conversion price and type of equity.

  10. Default Provisions: Details conditions that would lead to default, which may be monetary or non-monetary, and typically results in acceleration of the debt.

  11. Non-Financial Covenants: Similar to preferred stock, non-financial covenants can be attached to a debt instrument. These can include provisions related to board representation, management control, restrictions on related-party transactions, information delivery requirements, non-compete agreements, confidentiality agreements, limitations on management compensation, and restrictions on vital asset sales.

Understanding these elements is crucial when structuring debt agreements, as they impact the rights and obligations of both the issuer and the holder.

Gayatri Gupta