I write this as a founder, an exited founder, and an investor. I’ve sat on all sides of the table, and here’s a truth that’s rarely said aloud:

A good exit for a founder might not be a good exit for an investor.

In the swirl of valuations, pitch decks, and endless acronyms, the reality of life-changing sums of money often gets overlooked.

A thought experiment

Meet Jo.

Jo earns £30k a year. She has a mortgage, a credit card, and the occasional dilemma over whether to save for a modest family holiday or buy a new boiler. In other words: normal life.

She founds a company with a starting valuation of £1m, raises £250k, and gets going.

Twelve months later, a competitor comes knocking. They like what she’s built, want to move into the space, and put a clean offer of £1.5m on the table.

Should she take it?

On a purely personal level, it seems almost absurd that she wouldn’t. After tax and her investor’s share, Jo might clear £1m. In twelve months. From living month-to-month, she’s suddenly financially secure. That’s not just a “good outcome.” It’s life-changing. It’s practically the lottery.

Yet founders regularly turn this down. Perspective blurs. Future valuations and investor expectations take over. And sometimes – just months later – the company folds.

Could you live with walking away from the million in order to chase the mirage of ten?

The investor’s lens

For investors, Jo’s £1.5m exit is underwhelming. They bought in at a £1m valuation. On a £1.5m sale, once you account for fees, tax, and timing, they might scrape a modest return. More likely, they just about break even (and they won’t get EIS tax relief if this happens within the first 3 years).

If Jo had told investors up front that her ambition was to sell for £1.5m within 18 months, they would never have backed her. It’s simply not worth it from their perspective.

And this is the unspoken conflict:

– For Jo, the exit is extraordinary.

– For her investors, it borders on pointless.

The conundrum

This isn’t about who is “right.” It’s about recognising the mismatch.

Founders often have the chance to secure life-changing sums early in the journey. Investors, meanwhile, are playing a longer game – hunting for the rare multiples that make their model work.

The tension is obvious: founders may end up walking away from transformative money because it doesn’t suit the investor profile, or because the narrative tells them to “hold out for bigger.”

For Jo – earning £30k a year, mortgage to pay, life on hold – passing on £1m in order to preserve investor returns is arguably irrational. If that bigger exit never materialises, the regret will linger long and hard.

The unspoken truth

This is the quiet contradiction at the heart of founder–investor relationships. What looks like a “bad exit” to one party may look like salvation to the other.

We don’t talk about it much. But we should.

Because until we acknowledge this conflict openly, founders will continue to pass up life-changing outcomes in pursuit of investor returns – and investors will continue to quietly shake their heads when those outcomes land on the table.

So here’s my question to angel investors: “Would you accept a disappointing return, if it meant a founder could secure the outcome of a lifetime?