All About Capitalization Structure

Debt or equity: Which is the better choice for raising funds? This post discusses the complexities of capitalization structure, the ideal balance between debt and equity in your total capital, and the implications of these decisions.

Farheen Shaikh

22 April 2024

Table of Contents

When starting up, founders may initially use their personal funds to finance the business. However, they might also raise capital by selling ownership shares (equity) or obtaining loans (debt). This combination of funding sources shapes their capital structure, and achieving a correct balance here is critical.

For instance, a company with too much debt might struggle with high interest payments. On the other hand, a company with too much equity financing might dilute ownership stakes.

What is capitalization?

Capitalization refers to the total amount of capital invested in a company, encompassing both equity (such as common and preferred stock) and debt (such as bonds and loans). It serves as an indicator of the financial structure of a business, reflecting its ability to finance operations and fuel growth.

A company's capitalization is typically monitored and managed using a cap table, which lists all equity shareholders and their ownership stakes. However, it's important to note that without considering debt, one cannot fully grasp the true financial health of a company. 

Read more about cap table management.

Types of capital structure

The way a company finances itself plays a critical role in its success. Understanding the different types of capital structure allows companies to make informed decisions that optimize their financial health and shareholder value.

a. Debt capital

Debt financing involves borrowing money from lenders with a fixed obligation to repay principal and interest. It is often constrained in the early stages of a company due to the inherent risk and the lack of substantial assets that can be used as collateral. However, as companies mature and demonstrate viability, they may become eligible for debt financing options like bank loans, lines of credit, or equipment financing.

Debt comes in various forms

- Short-term debt (working capital loans) provides financing for day-to-day operations.

- Long-term debt (bonds, debentures) offers financing for larger projects or acquisitions.


- Tax shield benefit: Interest payments on debt are often tax-deductible, reducing a company's taxable income.

- Financial leverage: When used strategically, debt can magnify returns for shareholders if the company invests borrowed funds in profitable ventures.


- Debt creates a fixed obligation to repay, even during downturns.

- High debt levels signal a potentially risky investment for investors.

b. Equity financing

Equity financing involves selling shares of ownership in the company to investors.These investors become shareholders with varying rights depending on their share class. Common stockholders typically possess voting rights and are eligible to receive dividends. In contrast, preferred stockholders often have limited or no voting rights but may enjoy priority in dividend payments and company assets in the event of liquidation.

It is common to raise money through equity financing in the initial years of a business because of a lack of accessibility to debt.

For example, a biotech startup may raise equity financing from venture capitalists to fund clinical trials and regulatory approval processes for a new drug candidate. These investors provide not only capital but also expertise and strategic guidance to help the startup navigate complex regulatory pathways and accelerate its growth.


- Shared ownership fosters a strong 'skin in the game' partnership and alignment with investors.

- Equity financing doesn't create a fixed obligation to repay, reducing financial risk.

- Potential for high returns for shareholders if the company performs well.


- Issuing new shares dilutes ownership for existing shareholders.

- Equity financing can be expensive compared to debt. For example, Giving away 2% of your company, which could be worth 40 times its current value at liquidation, is more expensive than taking on debt at 12%.

c. Hybrid instruments

Hybrid securities, such as convertible debt (also known as convertible notes), combine features of both debt and equity. With convertible debt, investors extend a loan to the company with the option to convert it into equity shares under specific conditions. This enables investors to partake in the potential growth of the company without committing to a fixed share price upfront.  Convertible debt holds particular appeal for early-stage startups, affording founders the flexibility to postpone assigning a value to their company shares until later stages, when there's greater traction to support a higher share price.


- Convertible debt can be a good option for startups or companies with limited financial history to raise capital from investors without setting a share price.

- Convertible instruments such as Convertible debt or SAFEs attract lesser paperwork and statutory compliances upfront when compared to issuing stock, therefore shortening the fundraising period

- Documentation can be fairly standardized, for example, YC’s SAFE notes.

- Compared to equity financing, convertible debt can be a less expensive way to raise capital because the conversion can be tailored to higher valuation ranges, often defined by a floor and a cap.


- It’s difficult to provide upfront ownership visibility to the incoming investors depending on the complexity of these securities

- The accounting treatment of hybrid securities can be complex.

- Convertible debts may include an interest-rate component that accrues over time and converts into additional share issuance, apart from the principal, upon maturity.

- Some convertible debt instruments come with a "call provision" that allows the company to repurchase the debt at a predetermined price under certain conditions.

Factors determining capital structure

When choosing companies between debt and equity financing, companies must assess their business status and the costs of each option to decide. Here are a few things they usually consider:

1. Discounted Cash Flow (DCF)

When you're trying to decide between equity financing and debt financing, you want to see which option makes the most financial sense. Discounted Cash Flow (DCF) helps you do that by comparing the costs and benefits of each.

DCF is a method used in finance to estimate the value of an investment by forecasting the future cash flows it will generate and then discounting those cash flows back to their present value. The basic idea is that a dollar received in the future is worth less than a dollar received today, due to factors like inflation and the opportunity cost of not having the money available to invest elsewhere.

Let's say you're starting a lemonade stand and need $1,000 to buy supplies like lemons, sugar, and cups. You're trying to decide whether to borrow the money (debt financing) or find an investor who will give you the money in exchange for a share of your profits (equity financing).

For debt financing, let's say you can get a loan with a 10% interest rate. You'll have to pay back the $1,000 plus $100 in interest after one year.

For equity financing, let's imagine an investor offers you $1,000 in exchange for 20% of your profits. So if you make $500 in profit, you'd keep $400 ($500 - 20% of $500 = $400) after paying the investor their share.

Now, let's use DCF

a. Estimate future cash flows

You predict your lemonade stand will make $500 in profit each year for the next 5 years.

b. Discount to present value

We'll discount each year's profit back to its present value using a 10% discount rate.

Year 1: $500 / (1 + 0.10)^1 = $454.55

Year 2: $500 / (1 + 0.10)^2 = $413.22

Year 3: $500 / (1 + 0.10)^3 = $375.66

Year 4: $500 / (1 + 0.10)^4 = $341.51

Year 5: $500 / (1 + 0.10)^5 = $310.46

c. Compare financing options

For debt financing, you'd have to pay back $1,000 plus 10% interest compounded annually over 5 years, which comes to approximately $1,610.51. 

For equity financing, considering the present value of profit shares over 5 years, it amounts to approximately $379.07. We arrived at this by adding up the discounted present value of profits over the next five years and then taking 20% of that total.

What will you choose?

2. Debt-to-equity ratio

The debt-to-equity (D/E) ratio is a financial metric used to evaluate the proportion of debt and equity financing in a company's capital structure. It compares a company's total debt to its total equity, indicating the extent to which a company relies on debt to finance its operations and investments relative to shareholders' equity.

Mathematically, the debt-to-equity ratio is calculated as follows:

Debt-to-equity ratio = total debt/total equity

1. Total debt: This includes all the financial obligations of the company, such as bank loans, bonds payable, and other forms of debt. You can usually find this information on the company's balance sheet under the liabilities section.

2. Total equity: This represents the ownership interest in the company. It includes the initial investment by shareholders plus retained earnings (profits reinvested in the business). You can find this information on the balance sheet as well, under the equity section.

D/E ratio below 1 indicates that a company has more equity than debt, which is considered risky. When the ratio is between 1-2, it is a balanced capital structure and above 2 indicates high financial leverage.

The debt-to equity ratio impacts a company's financial structure in many ways:

1. Risk exposure: A higher debt-to-equity ratio increases financial risk by signaling greater leverage. This could lead to heightened vulnerability during economic downturns or difficulties in meeting debt obligations.

2. Cost of capital: A higher debt-to-equity ratio typically lowers a company's cost of capital as debt is often cheaper than equity due to interest tax shields, but excessive debt increases financial risk and cost of capital.

3. Investor perception: Investors closely analyze the debt-to-equity ratio to gauge a company's financial health and stability. A high ratio may spark concerns about debt management and meeting financial commitments, potentially influencing investor confidence. This is also a concern for investors because creditors are prioritized during liquidation.

3. Cost of debt

The cost of debt refers to the interest rate a company pays on its borrowings, including loans, bonds, or other debt instruments. It's a crucial component in determining a company's overall cost of capital.

For example, let's consider a manufacturing company planning to expand its operations. To finance this expansion, the company decides to issue corporate bonds with a face value of $10,000 at an annual interest rate of 5%. This interest rate represents the cost of debt for the company.

A lower cost of debt can make debt financing more attractive for a company compared to equity financing.If the cost of debt is lower than the cost of equity, increasing debt in the capital structure makes sense.

4. Cost of equity

Cost of equity refers to the return a company must generate on its equity to satisfy the expectations of its shareholders. It represents the compensation demanded by investors for the risk they bear by investing in the company's stock. This compensation typically comes in the form of dividends and capital appreciation.

For example, let's consider a tech startup named Tech Innovations Inc. founded by two entrepreneurs, Emily and James. They each invested $100,000 of their own money to start the company. Since Tech Innovations is a private company, there's no profit-sharing arrangement currently in place.

Emily and James expect a return of 15% annually on their investment. This 15% represents the cost of equity for Tech Innovations. It's the minimum return they require to justify the risk of investing in the startup.

Impact of capital structure on equity value

Here are some key ways in which capital structure can affect equity value:

1. Increase in leverage

a. Financial risk: Introducing more debt amplifies the company's financial risk. Higher leverage increases the probability of default, particularly during economic downturns or adverse business conditions. Credit rating agencies may downgrade the company's debt, leading to higher borrowing costs and further eroding equity value.

b. Interest expense: The additional interest expense associated with higher debt levels reduces the company's net income available to equity holders. This reduction in earnings can lead to a lower return on equity (ROE) and decrease the attractiveness of the company's stock to investors, further depressing equity value.

c. Market perception: Investors may perceive higher leverage negatively, viewing the company as riskier and potentially overleveraged. This perception can lead to a higher cost of equity capital as investors demand a higher expected return to compensate for the increased risk, contributing to a decline in equity value.

2. Increase in cash

a. Risk reduction: Increasing cash holdings enhances the company's financial stability and flexibility. It provides a buffer against unexpected financial shocks, such as declining revenues or unforeseen expenses, reducing the likelihood of distress or bankruptcy. This reduction in financial risk can improve investor confidence and support a higher valuation for the company's equity.

b. Dividend payments: Cash-rich companies have the flexibility to initiate or increase dividend payments to shareholders. Dividend payouts signal financial strength and management's confidence in future cash flows, attracting income-oriented investors and potentially boosting stock prices. Higher dividends can lead to a higher dividend yield, enhancing the attractiveness of the company's equity to investors.

Different types of capital structure models

Capital structure models provide a framework for analyzing the complex relationship between debt, equity, and company value. They include:

1. Traditional theory

The traditional theory takes a conservative approach by prioritizing equity financing. The rationale behind this approach is to maintain stability and avoid excessive financial risk. It operates under the assumption that increasing debt levels can deter investors due to the higher financial risk associated with it. 

Investors may perceive high debt as a signal of instability and may demand higher returns, thereby potentially lowering the firm's overall value. While this approach promotes stability, it might limit growth potential as it may restrict access to capital, especially in situations where equity financing alone might not be sufficient to fund growth opportunities.

2. Net Income (NI) approach

The NI approach focuses on maximizing earnings per share (EPS) through the strategic use of financial leverage. This suggests that if the cost of debt is lower than the return on investment, using debt financing can amplify EPS and increase equity value, up to a certain point. 

This is because debt allows the company to magnify returns to shareholders. However, this approach disregards the risks associated with high debt levels, such as increased financial distress and potential investor aversion. Companies adopting this approach must carefully balance the benefits of leverage with the associated risks.

3. Net Operating Income (NOI) approach

Similar to the NI approach, the NOI approach emphasizes the benefits of financial leverage, but it focuses on maximizing the return on invested capital (ROIC) rather than EPS. By utilizing debt to finance operations, companies aim to enhance ROIC and ultimately increase shareholder value. 

ROIC measures how well a company uses all its capital (including debt and equity) to generate profit. EPS suggests how much profit a company generates for each outstanding share of common stock. 

However, like the NI approach, it may overlook the risks associated with high debt levels. Thus, companies must assess the trade-offs between increased returns and heightened risk when employing this approach.

4. Modigliani-Miller (MM) theory

The Modigliani-Miller (MM) theory, consisting of MM1 and MM2 propositions, challenges traditional notions of capital structure by proposing that, in a perfect market with no taxes or bankruptcy costs, a company's capital structure is irrelevant to its overall value. 

MM1 assumes perfect capital markets where investors can create their own leverage through borrowing and lending, thereby negating any advantage of a particular capital structure. MM2 introduces corporate taxes, recognizing that debt interest payments are tax-deductible, providing a tax shield benefit that can potentially increase equity value.

However, it's important to note that real-world markets are not perfectly efficient, and factors like taxes and bankruptcy costs can influence a company's capital structure decisions.

5. Trade-off theory

The trade-off theory acknowledges the trade-off between the benefits and costs of debt financing. It suggests that initially, the benefits of financial leverage, such as tax benefits and increased returns to shareholders, outweigh the costs. However, beyond a certain point, increasing debt levels lead to heightened financial risk, which can result in higher borrowing costs, and a decline in equity value. 

Companies must strike a balance between leveraging debt to enhance returns and maintaining a sustainable level of financial risk.

6. Pecking order theory

The pecking order theory says that companies have a preference for how they raise money. They like to use their own profits first, then borrow money in a way that's not too risky, and only as a last choice, they sell part of their company to investors. This helps keep things clear between the company and investors because using profits or borrowing money doesn't send as strong a message to investors as selling part of the company does.

The Pecking Order Theory used to be a popular idea, suggesting that companies follow a specific order when raising funds. However, today, things have changed.  Raising money by giving away equity is considered a good option because VCs not only give you money but also help you strategically and unlock networks.

Why do capitalization structures get complex?

A company’s capitalization structure can become complex due to several factors:

1. Multiple financing sources

As companies grow, they often seek financing from various sources to fund their operations, projects, and expansions. These sources can include traditional bank loans, bonds, convertible securities, preferred stock etc. Managing multiple financing instruments with different terms, conditions, and covenants can add complexity to the capital structure.

2. Hybrid securities

Companies may issue hybrid securities like convertible notes that combine features of both debt and equity. Such instruments offer flexibility in raising capital but can introduce complexity in terms of valuation, accounting treatment, and investor rights.

3. Financial engineering

Companies engage in financial engineering to optimize their capital structure and capital costs. This can involve activities such as debt refinancing, debt restructuring, securitization, leveraged buyouts, or creating complex financial products. While these strategies can enhance financial efficiency and flexibility, they often result in intricate capitalization structures that may be difficult to understand and manage.

4. Global operations

Multinational corporations operating in multiple jurisdictions often face regulatory, tax, and currency considerations when structuring their capital. They may utilize cross-border financing, offshore subsidiaries, or complex legal entities to optimize their tax liabilities and access international capital markets.

5. Mergers and acquisitions

M&A activities can significantly impact a company's capitalization structure by introducing new debt, equity, or hybrid securities. Acquisitions may be funded through cash, stock issuance, debt assumption, or a combination of these methods. Integrating the capital structures of merging entities, managing debt levels, and optimizing post-merger financing arrangements can lead to complexity.

How to optimize the capital structure of a startup?

1. Risk analysis

- Conduct a thorough risk assessment to understand the company’s financial risk profile. Evaluate factors such as market volatility, revenue predictability, and operational risks.

- Use financial modeling techniques to quantify its exposure and determine the capacity to service debt obligations.

- Assess the impact of different capital structure scenarios on the company’s risk-adjusted returns and cost of capital.

2. Cost of capital optimization

- Calculate the weighted average cost of capital (WACC) by weighting the cost of debt and equity financing based on their respective proportions in the capital structure.

- Explore strategies to minimize the WACC by optimizing the mix of debt and equity financing. This may involve leveraging debt to benefit from its tax-deductible interest payments while balancing the associated financial risk.

3. Financial flexibility and liquidity

- Analyze the company’s liquidity position and financial flexibility to ensure it can meet its short-term obligations and capitalize on growth opportunities.

- Evaluate the trade-offs between maintaining liquidity reserves and leveraging debt to fund growth initiatives. Consider the access to alternative funding sources in times of financial stress.

4.  Recapitalizing

- Recapitalizing refers to the process of restructuring a company's capital structure by changing the proportion of debt and equity financing. This could involve issuing new debt or equity securities, repurchasing existing shares, or paying off debt. 

- It is typically needed when a company wants to adjust its financial structure to better align with its strategic objectives or to address specific financial challenges.

Hope you found this blog helpful. Remember, a well-crafted capitalization structure isn't just about raising funds – it's about setting the stage for long-term prosperity of your business. So choose wisely.