Going Big with Tyler Cowen, the Information Billionaire: The Future Belongs to the Non-Complacent

Why Going Big Today Often Looks Small, Uncomfortable, and Ambitious

One of the most counterintuitive ideas to emerge from my recent conversation with Tyler Cowen is this: going big today often has very little to do with size.

We’re living in a moment where a single person, a tiny team, or even one voice paired with the right tools can exert influence that once required massive institutions. A solo YouTuber can reach millions. A small research group using AI can outperform entire departments. Reach has been decoupled from scale.

That shift should be liberating. But it also exposes a deeper challenge that many leaders, organizations, and institutions struggle to confront.

When Everyone Around You Is Comfortable, You’re Probably in Trouble

Tyler offered an observation that should make every ambitious leader uneasy: if everyone around you is happy with how things are going, something is wrong.

That doesn’t mean you should provoke conflict for its own sake. Alienating people is not a strategy. But meaningful progress—real progress—almost always creates friction. The organizations, movements, and ideas that actually change the world rarely feel smooth on the inside.

Think about Apple under Steve Jobs. The Beatles at their peak. Michael Jordan and the Chicago Bulls. OpenAI today. When you look closely, you don’t find harmony. You find tension, disagreement, internal debate, and people pushing one another beyond what feels comfortable.

Strife, handled well, is often the byproduct of ambition.

The Trap of Scale Without Courage

Many leaders assume that going big means getting bigger: more staff, more committees, more process, more layers. But growth without courage often produces the opposite of impact. It produces bureaucracy. It produces risk aversion. It produces environments where people optimize for internal approval instead of external relevance.

Tyler’s point cuts against that instinct. In a world where reach matters more than size, the limiting factor is no longer capacity. It’s ambition.

Do you have the ambition to say something unpopular but true?Do you have the ambition to try something new before there’s consensus?Do you have the ambition to tolerate discomfort—your own and other people’s?

Most people don’t. And most institutions quietly reward those who avoid it.

Why Small Units Are Winning

One of the most important structural changes of our time is that very small units can now matter enormously.

Technology—and especially artificial intelligence—has lowered the cost of experimentation, publishing, research, and creation. You don’t need permission. You don’t need a gatekeeper. You don’t need a massive platform to start.

What you do need is clarity, persistence, and the willingness to be misunderstood for a while.

This is why so many of the most interesting ideas today are emerging from the edges rather than the center. They’re coming from individuals who are curious, disciplined, and ambitious enough to keep going long after the novelty wears off.

Productive Conflict Is a Feature, Not a Bug

One of Tyler’s most subtle but important insights is that conflict, when rooted in seriousness of purpose, is often evidence that something real is happening.

People attack what threatens complacency.They criticize what challenges existing narratives.They push back when the stakes feel high.

That’s true in media, in business, in nonprofits, and in public discourse. Free Press, which Tyler referenced, is a good example. The intensity of the criticism it receives is not a sign of failure. It’s a sign of relevance.

The absence of criticism, on the other hand, often signals irrelevance.

Ambition Is More Available Than We Think

Toward the end of the conversation, Tyler made a point that deserves to be underlined. Most people dramatically underestimate how much ambition they are allowed to have.

There is no authority figure handing out ambition permits. No one is going to stop you from thinking bigger, trying harder, or building something more meaningful—except the quiet internal voice that tells you to be reasonable, to wait your turn, to not rock the boat.

But boats that never rock don’t go anywhere interesting.

Going Big in a Hinged Moment

We are at what Tyler described as a hinge moment in history. Artificial intelligence is advancing at a pace few predicted. Institutions are under strain. Global uncertainty is real. The future of freedom, education, and work is very much up for grabs.

That reality should make us nervous. But it should also call forth courage.

Going big in this environment doesn’t require reckless risk-taking. It requires clarity, fortitude, and ambition. It requires staying curious. It requires surrounding yourself with people who challenge you, not just those who reassure you.

And it requires the humility to recognize that if everyone around you feels perfectly comfortable, you may not be aiming high enough.

The fruit is still on the tree. The question is whether we’re willing to reach for it.