Are you allowed to do that?

A friend asked, “Are you allowed to do that?” after I gave him creative suggestions for his YC application. It reminded me of the one quality that separates great founders from the rest: High agency.

Paul Graham describes it as being “relentlessly resourceful.” More generally, he called it the opposite of being hapless, where you just let things happen to you.

It’s the ability to see the world not as fixed but as flexible, where obstacles are just problems waiting for creative solutions.

Some people see rules as rules. A deadline is a deadline. The price is the price. And a no is a no. But great founders see things differently.

Instacart didn’t get into Y Combinator when it applied. The first problem was that the founder, Apoorva Mehta, applied two months after the deadline. But that didn’t stop Apoorva from using up his network to get intros to the YC partners. Despite that, he still got a rejection. So he pulled one more trick out of his hat.

He used his own product to deliver drinks to the office of the partner that rejected him to show him how Instacart worked. The partner called Apoorva immediately to invite him for an interview. Instacart is now worth $11 billion on the stock market.

Sometimes, founders will push the bar further into the gray zone between legal and illegal, preferring to ask for forgiveness instead of permission. This is not really an option in healthcare startups where you have to make sure everything is above board or risk your license. But in other industries, challenging the status quo is the only way to solve a systemic problem.

Travis Kalanick of Uber is a famous example of toeing the gray line. He was threatened with up to 90 days in jail for each ride Uber offered in San Francisco in the early days, in addition to thousands of dollars in fines. Most people would quit when faced with those challenges. But he had the confidence to push through.

Healthcare startups face a unique challenge. Progress often requires questioning inefficiencies like insurance delays, drug pricing, or outdated workflows, while staying compliant with strict regulations. High agency founders find creative ways to navigate these constraints without compromising their integrity.

Dr. Alex Oshmyansky, founder and CEO of the Mark Cuban Cost Plus Drug Company, decided to challenge the status quo of pharmacy benefit managers (PBMs) jacking up prices of drugs. He established a business model that bypasses PBMs. His company negotiates directly with drug manufacturers to offer medications at transparent, low prices, adding only a flat markup to cover costs.

Y Combinator famously asks founders to tell them about the time they most successfully hacked a non-computer system to their advantage. Hacking here doesn’t mean doing something illegal. It means creatively solving a difficult problem or “beating the system.” The application question came from Sam Altman, long before he created OpenAI, as a way to identify high agency founders. This is one of the most important questions on the application.

Throughout the early days of our startup, my cofounder showcased these skills daily. Whether it was getting lawyers to work for us for free, getting an important software contract we couldn’t afford renegotiated from $120k to $20k, or finding creative ways to create press for the company, he always made sure we punched above our weight class.

Rules exist for a reason, and disregarding them entirely would invite chaos. But progress often comes from studying which rules deserve to be questioned. Startups are born from this discomfort. Whether it’s Airbnb challenging housing laws or Stripe simplifying the complexity of global payments, these founders saw outdated systems as opportunities rather than immovable walls.

Steve Jobs said, “When you grow up, you tend to get told that the world is the way it is, and your life is just to live your life inside the world. Try not to bash into the walls too much. Try to have a nice family life, have fun, save a little money. But life, that’s a very limited life.”

Then, he makes a powerful observation:
“Life can be much broader once you discover one simple fact, and that is: Everything around you that you call life was made up by people that were no smarter than you. And you can change it. You can influence it. You can build your own things that other people can use.”

Founders aren’t anarchists; they’re builders. Whether you’re tackling systemic challenges in medicine, building a startup, or applying to YC, remember that the rules aren’t always fixed.