The Power of Preferred Stock: A Primer for VC, PE, and Founders

Preferred stock is a key financing instrument in the world of private equity (PE) and venture capital (VC), frequently used to balance the interests of investors and founders. Issued by corporations, preferred stock confers specific rights and privileges — often outlined in the company’s certificate of incorporation — making it distinct from common stock. These attributes, encompassing both economic and governance factors, can also be replicated in other business entities, like limited partnerships (LPs) and limited liability companies (LLCs), offering flexibility to investors. Below is an overview of the key features of preferred stock, particularly in Delaware corporations, which is the favored jurisdiction for incorporation due to its business-friendly legal framework.

What is Preferred Stock?

Preferred stock sits between debt and common equity in a company’s capital structure. Investors holding preferred shares receive preferential treatment compared to common stockholders, particularly in liquidation events and dividend payouts. Unlike common stock, which often focuses on capital appreciation through company growth, preferred stock can offer more stability and protection, making it a favored instrument in PE and VC deals.

Economic Attributes: Dividends and Liquidation Preferences

One of the primary appeals of preferred stock is its economic advantages.

Dividends

Preferred shareholders may receive dividends, which can be cumulative or non-cumulative. In a cumulative structure, missed dividend payments accumulate and must be paid out before common shareholders can receive any dividends. In non-cumulative arrangements, if a dividend is skipped, it’s not owed in the future. Dividends on preferred stock may be fixed or floating and, while less common in early-stage startups, they are more typical in PE-backed companies with stable cash flows.

In some instances, preferred stock may come without special dividend rights, meaning that preferred shareholders receive dividends on the same basis as common shareholders. This means that if a company decides to pay dividends, preferred shareholders are treated equally with common shareholders in terms of payout amounts and timing. This structure can provide potential upside for preferred shareholders if the company performs well and chooses to distribute dividends (while at the same time, preserving preferred shareholders liquidation preference, discussed further below). However, it also means that preferred shareholders lack the added security of a fixed dividend, relying instead on the company’s discretion, similar to common stockholders.

Liquidation Preferences

The liquidation preference governs the order in which investors are paid in the event of a liquidation, acquisition, or other exit scenarios (like a deemed liquidation, discussed further below). Preferred stockholders often enjoy the right to receive their investment back before common stockholders get any residual value.

Key concepts within liquidation preferences include:

• Senior Preference: Senior preferred stockholders are first in line during a liquidation event. This ensures they receive their investment back before any lower-tiered equity holders.
• Pari Passu: This structure treats different classes of preferred stock equally in a liquidation, meaning they share the proceeds proportionately.
• Junior Preference: Junior preferred shares rank behind (or are subordinate to) other preferred stock classes but ahead of common stock.

Liquidation preferences are often expressed as multiples of the original investment (e.g., 1x, 1.5x, 2x, etc.). For example, with a 2x liquidation preference, an investor would receive twice their original investment before common shareholders see any proceeds.

In addition to seniority and liquidation multiples, liquidation preferences can be structured as either non-participating preferred or participating preferred, each offering different payout scenarios in the event of a liquidation.

• Non-Participating Preferred: In a non-participating structure, preferred shareholders typically receive the greater of either their liquidation preference (e.g., 1x or 2x their original investment) or what they would have received if they had converted their preferred shares to common stock. This structure ensures that investors are protected on the downside while allowing them to participate in the company’s success if the liquidation event results in a payout higher than the liquidation preference. For example, if a liquidation event provides a higher return on an as-converted basis (i.e., by converting their preferred shares into common shares and participating in the overall distribution), they can elect that option instead.
• Participating Preferred: In a participating preferred structure, preferred shareholders receive their liquidation preference first, and then they also participate in any remaining proceeds alongside common stockholders. This offers more protection to investors but can reduce the overall payout to common shareholders. Some agreements include a cap on the participation, limiting the additional amount that participating preferred shareholders can receive once a certain threshold is reached.

Governance Attributes: Protective Provisions and Board Representation

Preferred stock often comes with governance rights that influence the decision-making process of a company. These rights ensure that preferred shareholders have a say in major decisions, providing them with a layer of protection.

Protective Provisions

Protective provisions grant preferred shareholders veto or consent rights over certain actions. These provisions typically cover events that could materially affect the company or the preferred stockholders’ position, such as:

• Issuing new shares, particularly new preferred shares that could dilute existing holders.
• Amending the company’s certificate of incorporation or bylaws.
• Engaging in a merger, acquisition, or sale of assets.
• Changing the number of board seats or approving new key executives.

These provisions ensure that significant changes in company structure or policy do not adversely affect the investors’ interests without their prior consent.

Board Representation

Preferred stockholders often have the right to appoint one or more members to the company’s board of directors. This helps investors maintain oversight and influence over the strategic direction of the company. Board seats are especially common in venture capital investments, where active governance involvement is critical.

In addition to board representation, the certificate of incorporation may specify additional voting thresholds that require preferred director consent for certain actions, further enhancing their influence. For instance, certain corporate actions — like issuing new equity, incurring significant debt, or altering the company’s capital structure — may necessitate a supermajority vote from preferred directors or even unanimous consent of the board, depending on the terms negotiated.

Alternatively, if a full board seat is not available, preferred shareholders may negotiate for a board observer role. An observer does not have voting rights but can attend board meetings, receive materials, and provide input. This arrangement allows preferred investors to stay informed and engaged with the company’s operations without the full responsibilities of a board member, balancing their need for oversight with the operational dynamics of the company.

Redemption Rights

Redemption rights allow preferred shareholders to require the company to repurchase their shares under specific conditions, offering a path for liquidity if an exit is delayed or uncertain. These rights are particularly important in cases where a company does not reach a successful exit, such as an acquisition or IPO.

Redemption can be (and often is) tied to deemed liquidation events, which could trigger redemption rights under circumstances like a change of control or sale of the company (or its assets). This ensures that investors have the option to recover their capital (plus some agreed-upon return, in many instances) even if the company’s growth or exit timeline doesn’t align with their original expectations.

Anti-Dilution Protection

Anti-dilution provisions protect preferred shareholders from the effects of subsequent financing rounds at lower valuations (often referred to as a down round), which could dilute their ownership. Generally speaking, there are two type of anti-dilution protection.

• Full Ratchet: This form of anti-dilution protection adjusts the conversion price of preferred shares to the price of the newly issued shares, regardless of how many shares the investor originally held. This means that if a company issues new shares at a lower price, the conversion price of the preferred shares is recalibrated to match this new lower price. This mechanism helps protect investors by ensuring their investment retains its value even if subsequent rounds occur at lower valuations.
• Broad-Based Weighted Average: This more common form of anti-dilution protection adjusts the conversion price based on a weighted average formula that considers both the price of the new shares and the total number of shares outstanding. This approach provides a more balanced solution, allowing the company to raise funds while still protecting existing investors from excessive dilution.

It is important to note that anti-dilution provisions typically come with specific limitations. Often, the certificate of incorporation will include exempted securities, which are certain types of equity or convertible securities that do not trigger anti-dilution adjustments. Common exemptions may include shares issued in connection with employee stock options, mergers, or acquisitions. By clearly defining these exempted securities, companies can facilitate strategic financing and growth without unduly affecting the interests of existing preferred shareholders.

Conclusion

Preferred stock is a powerful tool for aligning the interests of investors and founders. Its economic and governance features help ensure that investors are protected in downside scenarios while retaining influence over major decisions. Ultimately, understanding the structure and rights associated with preferred stock is important for both founders and investors in private equity and venture capital transactions. Finally, with the flexibility to mirror these attributes for other business entities, like LPs and LLCs, this form of equity (and its economic and governance attributes) can easily be adapted for other business structures beyond Delaware corporations.

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