Convertible securities carry with them a good mix of debt and equity financing combined in one which makes it more versatile both for investors as well as founders. Yet, their intricate character implies that attention ought to be paid so incentives are in sync.
Convertible Securities Explained

Conversion options: Debt securities convertible into equity at prices in conjunction with conversion values of the underlying common stock. It provides investors the equity like upside, with a debt-like safety net. A great way to raise capital for founders that does not immediately dilute them.
How do you balance investor and founder interests?
The secret for a winning convertibles trade is proper securitization, yielding satisfactory structure to both sides.
• Investor Perspective:
o Risk Mitigation: By having a debt component, convertible securities reduce the potential of completely losing money.
o Upside Potential - Conversion option eligible to participate in the Company's growth.
Liquidity: Although certainly not as liquid as publicly traded stocks, convertible securities are often more liquid than private equity.
o Valuation: Early-stage companies present difficulty to defining fair value so that the investors)}}
o Control Rights: Depending on relative investment size, investors may look for some board representation or control rights.
• Founder Perspective:
o Capital Organization: Convertible securities is an alternative source of capital without the immediate dilution.
Valuation Control - The founders keep control of the company's valuation until conversion occurs.
o Time Flexibility: The repayment of debt is optional in nature which relatively provides a more relaxation to the cash flows.
o Dilution: Convertibles can be structured to reduce dilution for an exit event.
o Growth Oriented: It allows founders to focus merely on the growth of business with no immediate future obligation about the equity financing.
Real-World Case Examples

The following are some high-ranking companies who have successfully employed convex securities:
• Facebook (Meta): By issuing a convertible security, Facebook gave its IPO investors an enormous return potential.
Uber: Uber ended up raising tons of capital with its use of convertibles, while giving it valuation control during growth.
Airbnb: By using convertible notes, Airbnb made it through the early days of the business and won flexibility in converting to equity when needed as for a more mature company.
Convertible Securities, Conversion Ratios:

• Conversion Price — Engaging proficiently to get the conversion price accurate and balance investor returns with founder dilution
Conversion Trigger: Establish that a conversion will only happen under certain conditions (e. g., common stock reaching/share by DATE).
• Interest Rate–Determine the interest rate to charge which should be a good return for investors, but at levels that do not crush balance sheet.
Establish a reasonable maturity date to provide for investors liquidity needs, while allowing flexibility for founders (yet another place where the right balance is key).
PREFERENCE: Define the order for being paid in case of liquidation to protect early investors.
-: Make anti-dilution provisions to guard towards dilution in future rounds.
When done right, these are a powerful feature for investors and founders. Through in this way, the interests of all parties can be taken into consideration to make profit from it with minimal risks. To get to a deal that works for everyone, you need good communication and negotiation.
Specific scenarios or parts of Convertible Securities you want me to discuss more on?
Reproduced below is a partial The Art of Negotiation post which discusses some critical convertible security and term sheet points.
Negotiating Convertible Securities: The Delicate Corporate Balancing Act Between Investors and Founders This negotiation is based on the term sheet, a non-binding document describing the investment terms.
Convertible Securities - Key Negotiation Points
Valuation: it is very difficult to know what the real in value of a pre-revenue or early-stage company Founders are likely to value the business too highly (overclaim) while investors normally undervalue it. Widely used methods A popular method is a combination of several methods comparable company analysis (CCA), discounted flow cash (DCF) and method venture capital.
The conversion price is a key factor as it determines potential dilution to the existing shareholders. On this basis, a high conversion price benefits founders as well while a low rate favors investors.
• Cap and Floor: A cap establishes an upper bound price at which the note will convert (to avoid over-dilution of early investors). The floor establishes a low valuation, providing some protection against this scenario as well.
• Discount: Provides investors who convert a lower price than later rounds, incentivizing early investment.
Interest Rate: Convertible securities have equity-like characteristics and typically pay interest. That rate should be measured against the potential equity upside.
Liquidation Preference: determines who in what order investors and owners get paid if the company is liquidated. The structure can further complicate with multiple tiers of liquidation preferences (participating/non-participating).
-Protective Provisions: Investors will want a protective provision to include board representation, veto rights or information right by participants. These provisions also lead to loss of founder control and reduced operational flexibility.
Case Study: The Zenefits Epidemic
Zenefits was supposed to be a star among HR software startups, but it ended up serving as an expensive example of how not to structure convertible securities. The company did this by raising convertible notes at very investor-friendly terms. But when the price crashed, investors converted their notes into equity - but at a valuation much lower than every other financing after that - leading to massive dilution for early seed-stage backers and founders. This incident highlights the need to look at convertible securities in a more nuanced manner from their long-term viewpoint.
The Startup Lifecycle and Convertible Securities
Convertible securities structure depends on stage of company:
• Seed Stage: The use of convertible notes is common given the valuation ambiguity at founding and founders also seeking quick capital. To cover the risks, investors demand higher interest rates or discounts.
• Series A: Companies increasingly employ convertible preferred stock as they ramp up. Investors can bargain for liquidation preferences, board seats and other protective provisions.
“Last Week: As companies mature and their valuation dynamics become more certain, traditional equity financing generally supplants issuance of convertible securities. Nevertheless, convertible preferred stock is still a useful choice for bridge financing or where investors prefer it.
Convertible securities provide an excellent means of company financing with ample flexibility for young startups, but they must be negotiated and underwritten very carefully. With a framework of common terms and issues to avoid, founders and investors benefit from win-win situations. If you want to make sure your convertible security agreement will be successful, then effective communication and legal counsel are required in addition of keeping long-term perspective.
If you would like to explore an even more in-depth look at any one specific part of convertible securities, whether it be valuation methodologies or the different importance levels that liquidation preferences hold as they change over time and event risk, please leave a comment below!
Convertible Security Valuation, Simplified (Not Really)
Valuing a private company is always particularly difficult, especially in the early stages. Convertibles - which are hybrid security types so their valuation brings 1 more layer of uncertainty.
Valuation Methodologies
Convertible securities are typically valued using one of the following techniques: -
Option Pricing Models: These models, which are most appropriate for publicly traded convertibles; view the conversion feature as if it were a derivative. The most well-known is the Black-Scholes model although it tends to not be as directly applicable to private companies given their lack of liquid markets.
Comparable Company Analysis (CCA) — By comparing the company to publicly traded peers with similar business models, investors can estimate a potential valuation range. But early-stage companies are hard to find a good comparable for.
venture Capital Method (VCM): This approach multiplies forecasted revenue or EBITDA against a valuation multiple While that is generally suitable for the seed-stage company, there are many assumptions made about unknown events of the future.
• Discounted Cash Flow (DCF): A method which is complex to apply and requires significant financial projections, DCF can nevertheless furnish a far more fundamental valuation. However, the quality of this estimate can only be as good as its underlying assumptions.
Convertibles: The role of valuation
Convertible security terms are fundamentally impacted by valuation.
Conversion Price: The higher the valuation, the steeper a company's conversion price will be and more beneficial it can prove to founders.
• FYI — Cap and Floor: The cap (price maximum) at which conversion kicks in is closely tied to the initial price.
Discount- The discount applied to the future valuation is a function of risk and growth attributes witnessed by investors on the company.
Liquidation Preferences: Two Sides of the Same Sword
Liquidation preferences help determine the priority and amount of distribution upon liquidation or sale They affect investor returns - and founder dilution - hugely.
•Conversion; Participating Preferred Stock: The holders receive their preferred return but upon the pay-out of this amount, these stockholders participate in all remaining proceeds (after payment to common) as if they were instead a holder of common. The structure provides maximum protection for investors, but can trigger enormous dilution to common stockholders.
Non-Participating Preferred Stock: Holders receive their preferred return but no more of the proceeds. Ticket. This is less investor-protective but prevents common stock ownership from being diluted.
Convertible securities can carry multiple tiers Liquidation preferences where different class of investors have preference over others. This may result in a complicated capital structure.
Product: Convertible Securities and M&A
When M&A gets complex - convertible securities How the conversion terms, liquidation preferences and anti-dilution provisions can affect both valuation & deal structure. When negotiating an M&A transaction, these factors should be weighed carefully.
Convertible securities are notoriously difficult to value and structure, but it is crucial for both your investors and you as a founder. A thorough understanding of available methods, the implications for various forms of terms and what this means in context can be critical to a successful negotiation. Rather than try to figure things out on your own, many people find its more worthwhile to discuss the complexities with financial and legal experts.
Maybe you want to dig deeper into something like anti-dilution provisions or how convertible securities perform in other industries, and whether econometrics has established the extent of impact on a convertible security investment when an economic downturn occurs.
Preventing Dilution: Protecting Investors
First introduced in the 1950s, anti-dilution provisions are a fundamental part of convertible securities and serve to counter acts that result in subsequent issuances or increases outstanding shares. It is vital for investor; this clause and these positions keep the investment phase in its economic level.
Categories of Anti-Dilution Provisions
• Full Ratchet This brings down the conversion price to a dilutive event and in turn lower them further at suspension events. The ordeal although is one faced with the maximum protection can be a nightmare for founders.
More common and typically considered as the more fare of the two: Weighted Average Otherwise it computes a new conversion price as a weighted-average of the prices at which all shares have been issued, with higher weight assigned to lower-priced issues.
Broad-Based Weighted Average – a variation of the weighted-average calculation that includes all equity securities issued, which also include options and warrants •
Anti-Dilution Provisions Effects
Potential dilution to existing Shareholders - depending on the governance of anti-dilutive provision chosen
Investor Perspective: Full ratchet provision offers the most protection, but may be a nonstarter for future investors due to its level of harshness. A weighted average provision is a little more balanced.
Founder Perspective: Full-Ratchet is probably worse, weighted average better for the founders (in a down-round)
Convertible Offerings Across Sectors
Like the tech sector, usage of convertible securities may also vary by industry.
• Technology: The tech industry leans heavily on convertible securities given its ability to benefit from the high-growth potential and valuation uncertainty associated with early-stage companies.
o Biotechnology — many companies within this sector are premature to the stage where they can confidently be advised on how conversion would affect the value of their businesses, but biotech usually presents a higher-level risk comparison so attracting investors with high yield GIC preferences in exchange for potential company growth-confidence share values may seem attractive.
• Other sectors: the use of convertible securities is less widespread but may still occur where a company has high growth prospects or operates in an industry where valuations are uncertain.
Economic Downturns
Convertible enforcement is not a perfect process as opposed to economic downturns in:
• Complexity Of Valuation During Downturns: The task of valuing companies in a trough economy is inherently cumbersome, leading to disagreements about valuation and potential re-pricing or resetting negotiations as they relate to convertible security terms.
Higher Risk: Investors may demand better terms, like higher interest rates, discounts on the purchase price or stronger anti-dilution protections.
• Delayed Conversions: Businesses may struggle to meet the conversion triggers and be burden by continued debt obligations.
It notes that convertible securities provide a tail-priced financing feature but whether they succeed is always determined by thoughtful structuring and negotiating. This way, companies can strike a win-win situation and cover their asses by balancing the interests of concerned parties such as investors & founders.
If you do, would you like us to discuss particular case studies of companies who used convertible securities well or deeper into the legal and tax implications?
Clinical Case Studies and Related Issues
Case Studies
• The Uber example: One of the most notable cases in which convertible security was effectively used, this rideshares giant will likely raise more than US$300m via convert-debt to get a significant funding boost without diluting itself prematurely. Which allowed the company to man oeuvre through its early growth spurt quite nicely.
Airbnb: Like Uber, Airbnb used convertible notes to grow. The flexibility provided by these securities gave Airbnb options to work with depending upon the market conditions at any given time and where investors were interested in investing.
Legal and Tax Implications
The legal and tax implications of convertible securities are not only complicated, but differ in every country. Key considerations include:
Security Classification — Whether a convertible security is classified as debt or equity for regulatory and tax reasons.
• Conversion Taxes: A walk-through of what it will cost to transform the securities into fairness.
• Deductibility of Interest: Evaluation whether tax deduction should be provided on interest payment.
• Contractual Terms: Ensuring the terms of the convertible securities fit within the applicable framework✍
Conclusion
Convertible securities convert at devices (another round of funding), offer a flexible way to finance startups that can be quite investor-friendly if structured and negotiated properly. Understanding how valuation, anti-dilution provisions and the regime of law & tax work best together in utilizing convertible securities can help companies more successfully deploy their growth objectives.
The practice of using convertible securities is probably only going to increase as the startup ecosystem matures. Being privy to the latest trends and best practices will enable companies to make most of this financing instrument.
Perhaps you want to focus on one area of convertible securities such as the effects using different legal jurisdictions, or their use within Venture Capital Funds?
Comments