Founders - What is your Number?

Over the years, many founders have asked me the same.

 “At what personal number is it okay to stop, exit or walk away?”

I usually joke that they should aim to be richer than their VCs and angel investors.

Then I give the more serious answer: it is deeply personal. It depends on your ambition, your family situation, your health, your mental state, why you started the company and what you want the rest of your life to look like. There is no single correct answer.

My usual advice is to listen to many stories especially stories with very different outcomes and then decide what works for you. The important thing is to make the decision consciously, so that you are less likely to regret it later.

But after investing in founders for many years, I have also become more opinionated about this.

From an investor’s perspective, I want founders to think bigger for themselves. I will admit that this generally produces a better outcome for me too. But it is also better for the founder.

Founders who do not think deeply about their personal number and who do not revisit it periodically can leave far too much on the table for other people. They may become less driven because the personal outcome no longer feels meaningful. Or they may make short-term decisions without understanding what those decisions will mean for their eventual ownership and wealth.

So today, I am going to be a little more pushy. I am going to suggest an actual number, at least for founders who intend to continue living in Singapore.

Why founders should aim higher

Building a startup is an unusually risky and draining activity.

Many founders pursue it obsessively for five, ten or fifteen years. The business occupies their thoughts at work, at home and on holiday. The uncertainty affects not only them, but often their spouses, children and parents too.

If you are going to commit such a large part of your life and expose yourself and your family to that much risk you should aim for a genuinely meaningful personal outcome.

You should also review that target every few years.

This is not simply about greed. For many people, their preferred standard of living only becomes clear in their late thirties or forties. By then, they have experienced more of the spectrum: different homes, holidays, restaurants, schools, healthcare choices and ways of travelling. They have a better idea of what they value, what they do not care about and where they can happily settle.

Your benchmarks may also change as you meet more people and observe more outcomes. The number that felt life-changing at 28 may look very different at 40, particularly after marriage, children and ageing parents.

Your number affects the decisions you make today

The real value of defining a personal number is not motivational. It is strategic.

If you know roughly what outcome you are trying to achieve, you can work backwards and make better long-horizon decisions about:

● how many co-founders you should have;

● how much dilution you can reasonably accept;

● how many rounds of capital to raise;

● which investors and investment terms to accept;

● whether secondary liquidity makes sense;

● when to buy back or claw back shares;

● how to structure employee equity; and

● how much ownership you must retain as the company scales.

I have seen positive examples of founders who realized that they had given away too many shares early, then found opportunities to buy back or earn back ownership at key moments as the business grew.

I have also seen founders who did not think far enough ahead about their future selves. By the time the company became valuable, they owned only a low-single-digit percentage of the business. Sometimes that still produced a good outcome. Sometimes it did not adequately compensate them for the years of risk and sacrifice.

Ownership decisions that appear small in the early years can become enormous later. A deliberate and patient strategy, careful investor and cofounder selection can make a huge difference to the end result.

So, what is the number?

Friends will tell you that I am not actually the most ambitious person by entrepreneurial standards. I exited relatively early, in my late thirties. I benchmarked myself against successful corporate leaders (not billionaires or centimillionaires) and, fortunately, managed to stop raising my mental bar after I exited.

Having now spent more than ten years as a semi-retiree in Singapore, with a reasonable understanding of what most things cost and how investment returns work in practice, my suggested target is:

At least S$20 million in cash to you

By that, I mean personal, liquid proceeds not a headline valuation and not the paper value of shares you still cannot sell.

I am not going to unpack the full mathematics here: early-retirement portfolio construction, inflation, sequence-of-returns risk, the cost of a good home in Singapore, family obligations, healthcare, education and what a top 1% to 5% household lifestyle can cost over several decades.

But my S$20 million figure bakes those considerations in. I would describe it as a conservative minimum only if the founder knows how to invest sensibly and manage spending. A safer target would be S$30 million or more.

Of course, S$20 million is not necessary for a happy or meaningful life. That is not the argument. The point is that startup entrepreneurship is an exceptionally demanding and concentrated gamble. If you are choosing to run that gamble for a decade or longer, your target outcome should reflect the risk, sacrifice and opportunity cost involved.

Having a number does not mean you must sell

This is important: defining your number does not mean you should automatically exit the moment you reach it.

The purpose is to revisit the number, plan ahead and protect the ownership required to give yourself a fair chance of reaching it.

In fact, the best entrepreneurs often reach their number many times over and still retain ownership of their businesses. Many of the world’s great business families built their wealth precisely because they found ways to create liquidity, diversify and continue owning the core assets across generations.

So if you are a founder and have never defined your personal number, perhaps it is time to do so.

Write it down. Explain why it is enough or why it is not. Work backwards from the likely value of your company and the percentage you may own at exit. Revisit the calculation every few years, or whenever your life and the company change materially.

The precise number matters less than the discipline of thinking about it.

Because if you do not plan for your own outcome, everyone else around the table will still be planning for theirs.