In the last five years, I’ve spent a lot of time evaluating founders. Through my podcast, Seedscout, and Mat Capital, I’ve met thousands of founders, and it was my job to decide who I should introduce to my network of angels and VCs—and who I shouldn’t. Usually, it was pretty easy to know whether I was going to make the intros or not. If they previously worked at a hot startup, went to Stanford or Harvard, or had a startup with explosive traction in a strong market with good margins, I generally opened up my network. If a founder wasn’t technical, was just getting started, or wanted to raise before building, it was an easy "pass for now”. But then there was this one type of founder—the ones I always got stuck on.

They were technical, smart, working on an interesting problem, and had already made progress. Maybe the startup wasn’t blowing up, but the progress was notable or seemingly impressive. These were all positive signals that a founder was a winner. And yet—almost every time I tried to help this type of founder, we didn’t really get anywhere. I could never figure out why. I have pattern recognition. I can identify talent. I have an excellent network. So why couldn’t I help them? Then It finally clicked. I needed to look beyond just talent—I also needed to evaluate one simple question.

Are they a high-context founder?

The best way to tell if a founder is high context is whether you can talk shop with them, and they can hang. It’s when you name-drop insider terms, and they already know what you mean. It’s when you mention a less well known VC, and they already have an opinion on them. It’s when you bring up a podcast, and they tell you they just listened to the latest episode. A high-context founder isn’t just smart or skilled—they understand the culture of tech. They are in the world.

Why does this matter?

Anyone who can keep up a conversation about niche topics that aren’t widely understood can likely do the same with investors, operators, and customers. A high-context founder has already positioned themselves—consciously or not—to understand the monoculture of tech. Either they were born into it, or they figured out that it was important and made the effort to absorb it. Regardless of how they got there, a high-context founder is less risky to bet on than a low-context one.

• A high-context founder knows South Park Commons, HF0, and AI Grant. A low-context founder only knows YC, Techstars, and Founder Institute.

• A high-context founder knows what bad terms look like. A low-context founder thinks any terms are good terms.

• A high-context founder builds their startup. A low-context founder builds their local scene.

• A high-context founder knows who tier-one investors are. A low-context founder thinks the investors in their (non SF/NYC) city are the tier one investors.

• A high-context founder calls it SF. A low-context founder calls it San Fran.

Being a high-context founder reduces your beginner mistakes, decreases your odds of following bad advice, and increases your chances of survival. It’s still brutally hard. But I’d bet on one high-context founder over 10 low-context founders any day.

How do you become a high-context founder?

The only way is to spend time with them. The most obvious way? Go to school in a high-context environment—Stanford, Harvard, MIT. Or work at a company full of high-context people—Stripe, OpenAI, Anduril. If that’s not attainable, the advice is still the same: find the most high-context people around you and spend time with them. Learn from them. Ask them questions. Adopt a beginner’s mind. Figure out what they read, what they listen to, and where they go. Then read the same things. Listen to the same podcasts. Go to the same events. Meet the people they hang out with. Through osmosis, you will build context on this industry.

Yes, There Are Levels To This

Everyone is on a different level of context. I am high context to some and low context to others. You think I’m high context to Jeff Bezos? Probably not. But I’m high context to almost every founder and VC in early-stage startups. And if I keep doing what I’m doing, hopefully, my context window grows until one day, I could be considered high context to even Jeff Bezos.

The moral of the story: if you aren’t getting anywhere in your founder career, maybe it has nothing to do with your skill, talent, network, or idea. Maybe you are simply a low-context founder. And if you can admit that to yourself, you can start to improve your context.

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