The question I ask about every market

What should investors really look for in a founder?

It’s one of the hardest questions to answer well. Beyond the pitch, the market and the numbers, what tells you how a founder will actually build?

One signal I look for is how they see the market around them. Are they building into open space, or spending much of their energy fighting what already exists?

That distinction came through clearly in our latest Majlis conversation with two founders building in The GCC. It also points to a broader question we’ll explore in our next House of Arāya Academy: how do experienced investors evaluate a founder before they have the full picture?

When I assess a company, one of the most useful questions I ask is how much of the founder's energy will go into fighting the old way of doing things, versus building into open space.

Some companies spend years displacing what's already there. They have to rip out the tool a customer already uses, retrain people, win against incumbents with deep relationships, and work around infrastructure built for a different era. That fight is winnable, but it's slow and expensive, and it eats the runway a startup can least afford to lose.

Others build where there's little to displace. The customer has no established alternative, the workflow is new, and adoption asks no one to unlearn a habit. Those companies tend to move faster and compound sooner, because their energy goes into building rather than into prying customers away from something they already have.

One isn't always better than the other. But knowing which you're looking at tells you a lot about how hard the road ahead will be, and how much of your capital will go toward progress rather than toward overcoming inertia.

The GCC makes this easy to see, because so much of the legacy isn't there yet. One founder, Zade Al Borshaid, is building a real estate brokerage that runs on data. In Dubai, the land department already exposes APIs for rental contracts and permits. In much of the world, he pointed out, the same request means a fax, or a PDF if you're lucky. The rails are being laid new, and laid digital, so a founder there builds forward instead of building around the past.

You can find that same quality in pockets of many markets. A category with no default incumbent. A workflow AI has only just made possible. A customer who's never had a tool for this before. Those are the places where a strong product meets the least resistance.

Next time you look at a deal, ask where the company sits on that spectrum. How much of the plan depends on customers abandoning something they already rely on? How much of the first two years goes into displacement rather than building? A company delivering into open space can move at a speed a company fighting legacy rarely matches.

The best opportunities can sometimes look almost too early, where the canvas is still blank and most investors haven't thought to look yet.

I get into this with both founders in this episode of Majlis, filmed in the UAE.

What should investors look for in a founder?

This week’s idea of legacy drag is one example of the kinds of signals that can tell you more about a founder than the pitch itself. How they see the market, where they choose to build, what they recognise that others have missed, and how they navigate the constraints around them can all reveal how they think as an investor.

That is the focus of our next House of Arāya Academy session: how to evaluate a founder before you have the full picture.

We’ll unpack the questions experienced investors ask, the signals they look for, and how to distinguish genuine insight from a compelling story.

House members can join the next Academy session →

Not yet a member? Explore the House and apply to join →

Warmly,
Rupa

P.s. When you're ready, here are 3 ways I can help: