What this chapter covers
How the choice between debt and equity follows from what the capital finances: visible repayment capacity, the real cost of dilution, hybrid answers and the balance sheet the company already carries.
Key takeaways
- Start from what the capital is financing, not from the instrument.
- Debt works when the repayment path is visible in the cash flows.
- Equity is appropriate where the outcome is uncertain and the horizon is longer.
- Dilution is one cost among several; covenants and control are costs too.
- The existing balance sheet limits what the next financing can look like.
When a company needs capital, one of the first questions is usually whether to raise debt or equity.
The answer is often treated too simplistically. Debt is described as cheaper because shareholders are not diluted. Equity is described as safer because it does not need to be repaid. Both statements can be true, but neither is enough to determine the right structure.
The real question is not which form of capital is better in general. It is which form of capital the business can realistically support, given its cash flows, growth plan, risk profile and objectives.
A company can raise the right amount of money through the wrong instrument and still create a bad transaction.
Start with what the capital is financing
The intended use of funds should normally come before the choice of financing.
Consider two companies both seeking €10 million.
The first is a mature industrial business generating €5 million of stable annual EBITDA and wants to finance a new production facility supported by existing customer demand.
The second is a technology company still investing heavily in growth, with limited current profitability, seeking €10 million to expand into several new markets and develop new products.
The amount is the same. The financing problem is completely different.
The industrial company may be able to service debt from existing and incremental cash flows. For the technology company, requiring fixed interest payments and principal repayment before the expansion has produced predictable cash flows may put unnecessary pressure on the business.
Capital structure should therefore follow the economic profile of the investment being financed.
When debt makes sense
Debt can be attractive because existing shareholders retain ownership and, if the investment performs well, the upside remains with them.
But debt is not simply capital without dilution. It creates contractual obligations.
Interest must be paid. Principal must eventually be repaid. Financial covenants may need to be respected. Security may be required. Certain corporate actions may be restricted without lender consent.
For that reason, lenders will focus heavily on the company's ability to generate cash.
A company with predictable revenues, stable margins and strong operating cash flow is generally better positioned to support leverage than one whose future performance depends on assumptions that have not yet been tested.
The key question is not whether management believes the company will grow.
It is whether the business can continue servicing its obligations if growth is slower than expected.
A financing structure that only works under the management team's most optimistic forecast is usually too aggressive.
The repayment path needs to be visible
One of the most practical questions in a debt transaction is also one of the simplest:
where does the money for repayment come from?
If a company borrows €15 million for five years, the lender needs a credible answer.
Repayment may come from operating cash flow, refinancing, asset disposals or, in certain structures, a bullet payment supported by a clearly identifiable liquidity event.
What matters is that the repayment strategy is connected to the actual business model.
For example, financing a property development with debt can make sense where repayment is expected from identified asset sales. Financing continuing operating losses with short-term debt while assuming that “the next round” will repay the lender is a much more fragile proposition.
The debt product should also match the timing of the investment. Long-term capital expenditure financed with a facility that must be repaid before the asset starts generating cash creates an obvious maturity mismatch.
When equity is more appropriate
Equity is generally better suited to capital needs where the return is uncertain, the investment horizon is long or the business needs flexibility before generating meaningful cash.
An investor accepts that capital may remain at risk for several years and normally expects compensation through participation in the future value of the company.
For the business, this removes the immediate repayment burden. But the cost is different rather than absent.
The founders are giving up part of the ownership and, frequently, part of the control.
An equity investor may request board representation, information rights, vetoes over certain decisions, anti-dilution protections or specific exit rights. Future dividends and sale proceeds are shared with the new shareholder.
A founder considering equity financing should therefore look beyond the valuation.
Selling 25% of the company is not simply “raising €10 million at a €40 million valuation”. It means introducing another shareholder into decisions that may affect the company for many years.
The right investor can add expertise, credibility, relationships and additional capital. The wrong investor can create strategic friction that is difficult to reverse.
Dilution is not always the most important cost
Entrepreneurs often reject equity because they do not want to dilute their ownership.
That instinct is understandable, but percentage ownership should not be considered in isolation.
Owning 100% of a company worth €20 million is economically different from owning 70% of a company that, with the right capital and execution, becomes worth €100 million.
The opposite is equally true: raising equity at an unnecessarily low valuation can permanently transfer substantial value away from existing shareholders.
The relevant question is therefore not simply how much ownership is being given away, but what the capital is expected to create in return.
If €10 million of new equity allows the company to enter a market, acquire a competitor or build capacity that would otherwise be impossible, dilution may be economically rational.
If the capital merely covers recurring losses without a credible path to improvement, the same dilution may only postpone the underlying problem.
Sometimes the answer is both
The choice is not always binary.
Many transactions combine debt and equity.
Suppose a company needs €20 million to acquire a competitor. Funding the entire amount with equity may cause unnecessary dilution. Funding the entire amount with debt may create excessive leverage.
A structure combining €12 million of debt with €8 million of new equity may produce a more sustainable balance.
Other forms of capital can sit between traditional senior debt and ordinary equity: subordinated debt, mezzanine financing, convertible instruments, preferred equity or vendor financing.
Each comes with a different combination of return, control, priority and risk.
The purpose of structuring is not to select the most sophisticated instrument available. It is to create a capital stack that the company can actually sustain.
What the balance sheet already looks like matters
A financing decision cannot be made without looking at what is already there.
A company generating strong EBITDA may appear capable of taking on additional debt, but the conclusion may change if it already has significant bank facilities, shareholder loans, leasing obligations and short-term liabilities.
Similarly, a company with little financial debt may still have large working capital requirements that absorb most operating cash flow.
Investors and lenders therefore look at the business in context.
How much leverage exists today? When does existing debt mature? What security has already been granted? Are there covenants restricting new borrowing? How much cash does the company actually generate after capex and working capital?
These questions determine the capacity for additional financing far more reliably than a headline EBITDA figure alone.
The advisory role is to challenge the initial request
Management often begins a financing process with a predetermined view: “we want €15 million of debt” or “we want to sell 20%”.
That view should be treated as a starting point, not necessarily as the final structure.
A proper advisory process tests the request against the business.
If the company cannot support the proposed debt, the solution is not simply to search for a more aggressive lender. It may be to reduce the debt component, add equity or redesign the investment plan.
If the company can comfortably support borrowing, selling a large equity stake simply because an investor is available may not be optimal either.
Sometimes the best advice is to raise less capital. Sometimes it is to raise more but for a longer period. Sometimes the right recommendation is to delay the transaction until financial performance supports better terms.
The objective is not merely to obtain funding. It is to obtain funding without damaging the company that the funding is supposed to help grow.
Capital should fit the business, not the other way around
Debt and equity solve different problems.
Debt works best where the company can demonstrate a credible ability to service and repay capital without compromising the business.
Equity works better where the company needs risk-bearing capital, flexibility and time before the expected return materialises.
And in many cases, the right answer is a combination of both.
The most important point is that financing should not begin with the instrument.
It should begin with the company: its cash flows, its objectives, its existing balance sheet, its risks and the investment it is trying to make.
Only then does the real financing question become clear:
not “debt or equity?”, but “what capital structure gives this business the best chance of succeeding after the money arrives?”
