Run the Room

What if you’re not risk-averse, but leverage-blind?

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There's a lot of hullabaloo about the billions of dollars now flowing into philanthropy from the AI boom.

And while there's plenty of speculation about where it will go, there's also an emerging consensus: a lot of it (a lot!) will go toward "GiveWell"-style giving: interventions with strong evidence, measurable outcomes, and a reasonably clear answer to the question, “What did this dollar buy?”

And this prompts a much larger question:

Why do people who spent their working lives making enormous bets under extreme uncertainty become so conservative when they allocate their wealth?

Think about what it took to build an AI company: you bet years of your life on something that might not work, make decisions without knowing the answer, spend money before you know whether the market exists, and build before you have proof.

And if you're successful, you might even do it again!

These aren't people who need certainty before they act. So why do AI founders who bet a decade on “maybe” now want a receipt at point of purchase when it comes to their philanthropy?

I don't think the answer is that they've suddenly become risk averse.

I think the nature of the uncertainty has changed.

When you're running a company, uncertainty sits inside a mechanism founders know how to operate: form a hypothesis, build something, put it in front of someone, watch what happens, change it, and try, try, try again.

You don't have to know whether the company will succeed. But you usually know what to do on Monday.

In other words: the uncertainty is enormous, but the next move is usually available.

But try to change how a government provides services. Or why some people get left behind in the economy. Or how power gets distributed between the people making decisions and the people living with them.

You can't just build a better product and see what happens.

There are employers, governments, regulations, incentives, norms, history, and people with competing interests all tangled together.

And that’s a much harder thing to put money behind.

So we retreat toward what we can see: the intervention with the known evidence base, measurable outcome, and straight line to what your dollar bought.

Nothing wrong with any of that.

The problem is when we start treating what we can measure confidently as what will have the most impact.

And I think we do this at work all the time.

We say the consequential thing isn’t moving.

So we push harder: have another meeting, make another deck, send another email, get more people in the room.

All of those things feel like action because we understand how to do them.

But we’re often skipping the harder question:

What’s actually keeping this stuck?

If you don’t know the answer to that, you can’t know where to intervene.

The answer isn’t to become more comfortable with uncertainty, but to make the uncertainty navigable:

Figure out what conditions are holding the thing in place.

Find where you have leverage.

Make a hypothesis about what might move it.

Decide what would tell you you’re wrong.

Then test it.

And do it again.

You don't need to choose a simpler problem. You need to make the path through the hard one easier.

Try this

Think of one piece of work you've been saying is important but isn't moving. Then look at your calendar from the last month and ask:

How much of that time was spent figuring out what is keeping it stuck?

And how much was spent trying to push it forward anyway?

Now write down your best hypothesis about what's holding it in place.

What would have to change for movement to become easier?

Pick one thing you can test this week that will give you information you don't already have.

Not a plan.
Not another conversation about the plan.
A test.

🌿 Don't retreat from the difficulty. Make your route through it easier.