How a good raise turns into a broken cap table, and the five decisions that keep you holding a meaningful share.

Founders assume the investor across the table wants as much of the company as possible for as little as possible. That’s the wrong model, and believing it leads to exactly the wrong decisions.

We asked Hlayisani Capital co-founder and partner Brett Commaille, who has spent around 15 years in SA venture, how founders should think about how much to raise…

The trap runs like this. You raise a lot at a high valuation early; the journey doesn’t go to plan, you raise again, dilution stacks, and by the time the business finally hits its stride, the founder has 10% left. At that point, investors have to clean out the whole cap table and get everyone to reset, which is a rough conversation nobody wants.

“I have one concern: that the business has enough money to reach the next stage.”

Work out what the business needs to reach its next real stage, and raise that. Not the maximum on offer, not what your peers announced. A small enough amount to get far enough down the line keeps your stake meaningful and leaves room for the rounds that follow, which is the whole game over a decade.

Chasing the biggest number backfires with a delay. When real metrics arrive, and they don’t support what you sold, you can be forced into a down round, which signals failure and makes the next raise materially harder. Thalia Pillay put the same point from the founder’s side at the same event: keep your valuation as low as long as possible, and ask whether you can actually grow into the number you’re being offered.

Brett has seen deals die because an angel took 60% for R1m and then wouldn’t let go of the equity. Nobody can invest behind that, because there’s no room left for the rounds the business actually needs. Cheap money early is the most expensive money you’ll ever take if it comes with a share of the company nobody can work around later.

Instruments like SAFE notes exist for a good reason: because pre-revenue, a valuation is essentially invented, and they let you defer it. The catch is what happens when several of them convert at once. Use them, but keep count, because stacking too many means paying the price on dilution later, all in one go, at a moment you don’t control.

An investor who takes 40% today and can’t participate in the next four rounds is a problem for both of you; Brett’s point is that they’d very quickly be handing shares back to the founder. What you want instead is someone who takes a modest position and follows on as you grow, because that’s where their real returns come from too. Ask directly whether they follow on, and whether they have the capital to do it.

Get this right, and you arrive at the moment the business finally works, still owning enough of it to care, with a cap table an investor can actually build on rather than one that has to be cleaned out first.

Brett’s full fireside from Founder Collab Live is available to members inside the Founder Collab, where he goes further than we could cover here:

You’ll also get access to 40+ masterclasses from SA founders and operators on sales, fundraising, UX, paid media and more inside The Founder Collab.

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