There’s a big difference between playing the game and winning the game.

Getting investment lets you play. Exiting your business is how you win.

It sounds simple, but the line is easily blurred – sometimes by founders, sometimes by investors, and often by the noise around the industry itself.

Playing the game

Raising money is not the goal. It is not “winning.” It is simply a mechanism to stay in the game.

Yet the startup echo chamber often makes it feel otherwise. Headlines trumpet the latest £20m Series C or the billion-pound valuation, as though these events are the prize themselves. Founders are celebrated for the size of their raise, not the substance of their outcome.

The reality is that fundraising buys time. Nothing more.

It funds growth.

It extends runway.

It validates ambition.

But it does not deliver value back to the people who took the risk of founding in the first place.

Winning the game

Winning usually means selling your shares.

Not issuing new primary shares in exchange for capital. Not paper valuations that say you’re worth £90m because someone bought in on certain terms.

Winning means a buyer is willing to write a cheque for your equity. That’s the moment theoretical value becomes actual value.

And it’s a much higher bar. It requires:

• A business model that works without endless outside capital.

• Evidence of scale, not just promises of it.

• A market buyer who sees strategic or financial value in owning the whole entity.

This is why it’s far harder to win than to play.

The illusion of winning

Plenty of founders look like they’re winning for years.

They raise large rounds. They post impressive bank balances. They appear in the press with enviable valuations. On paper, they look like success stories.

But paper is deceptive. The money is often locked inside the company, earmarked for headcount, marketing, or international expansion. The founder’s equity is still illiquid. Their personal outcome is still zero.

Vanity makes it worse. “We’ve just closed a £10m round at a £90m valuation.”

That’s not winning. That’s prolonging play. And often it means you’re no longer playing on your terms. Each successive round dilutes your control and increases the minimum bar for what counts as a “good” exit. In some cases, the game becomes unwinnable — at least in the sense of a clean, founder-rewarding exit.

Why the distinction matters

This difference between playing and winning isn’t just semantics. It shapes behaviour.

If founders equate fundraising with success, they risk optimising for the wrong milestones. Bigger rounds. Higher paper valuations. More headlines. All while drifting further from an actual, bankable outcome.

Investors, too, can be complicit. Valuations are talked up, follow-on capital is celebrated, but when the music stops, the underlying question remains: who actually realised value?

What it takes to win

To win, you must be able to get out. To move value from your shares into your account. To transform theoretical equity into tangible reward.

That means thinking early about:

• Exit pathways: who might actually buy this business, and why?

• Deal dynamics: how much leverage will you have when the time comes?

• Cap table discipline: are you still in a position to benefit personally from an exit, or has the game moved beyond your control?

Winning isn’t about raising ever-larger rounds. It’s about keeping your options open, and ensuring that the story you’re telling ends with someone writing you a cheque, not just another term sheet.

The hard truth

Raising isn’t winning. Raising is facilitation.

Exiting is winning. And contrary to the noise, it’s harder – much harder – to win the game than to play it. Because not all players can be winners.