What Founders Teach Us

Lessons from those who choose to live by the river

Photo by kazuend on Unsplash

Most of my career has been spent inside founder-led companies. I have also had the privilege of working with many founders through angel investing, advising, and mentoring as their companies scaled. When I joined PayPal and later Facebook, both were still in their early, scrappy stages. They were founder-led, and that energy was everywhere. It was contagious. That anything-is-possible attitude made you want to push harder, take bigger bets, and keep going even when things got tough.

Being around founders taught me something important: they see the world differently. And if we pay attention, even those of us who are not founders can learn from the way they think and lead.

Over time, I have seen up close what makes them extraordinary. These traits let them believe they can beat the odds, even knowing that 90 percent of startups fail. They pour everything into what they are building. They risk financial stability, endure wild swings in fortune, and handle stress most people would not choose. But they all share one thing: a kind of unshakable optimism.

Fearlessness

Nate Silver describes these types of risk-takers in his book On the Edge. He writes about two types of people: those who live in the village and those who live by the river. The villagers live stable, predictable lives. They farm, trade, and build within the safety of their routines. The river people are different. They thrive in uncertainty, living and dying by the river’s bounties and dangers. They gamble, betting that when the river rises, they will be the ones who catch the current. Most of us choose the village. Founders are almost always the ones by the river.

They are willing to put everything on the line for something they believe in. They see a problem and will not rest until they solve it.

One founder I know is relentless about asking for what she needs. Her fearlessness makes her an incredible evangelist for her company and the problem she wants to solve in the world. Her enthusiasm is infectious, and her willingness to put herself out there gets results. She certainly hears “no” often, but she moves forward undeterred because the next “yes” is right around the corner. That is an X factor that is difficult for others to replicate.

Learning Mindset

Founders are constantly flooded with new information. The data says one thing, a customer says another, and the market tells them something else entirely. They must know what to listen to and what to ignore.

The best founders actively seek out opposing views. A CEO I know regularly invited contrarians into the room because he felt his team agreed with him too much. He understood that dissenting voices, while uncomfortable, would make him a stronger leader.

I have written before about the value of reframing questions to uncover new possibilities. Founders often do this instinctively, shifting their perspective to find the signal in the noise.

Execution

Founders understand the saying, “Execution eats strategy for breakfast.” Two companies can have the same plan, but the one that out-executes will win. A team that grows a little faster every day, invests in the right things, and adapts quickly will leave competitors behind. Momentum is hard to catch up to once you lose it.

I often think about Andrew Wilkinson’s story of Flow, his team task management app, which was overtaken by the better-funded but later-to-market Asana. Wilkinson bootstrapped while Asana raised millions, built a bigger engineering team, and blanketed the market with marketing. Wilkinson summed it up best: “Good product with great marketing beats amazing product with no marketing.”

Execution is about more than a product. It is about building a machine that works: marketing that resonates, sales that scale, messaging that connects, and iteration that keeps you ahead. Founders who master that full picture are the ones who survive the river.

Imagination

I spoke to a founder recently who shared that someone in his industry told him his idea would never work. His response was, “I love it when someone hates the idea. That means less competition and more opportunity.”

The best founders do not need everyone to believe. They only need to find the people who do. They see a future where their company thrives, even before anyone else can picture it. That conviction, whether it leads to failure or triumph, is what makes them exceptional.

Ignoring the Right Things

Founders know how to tune out the noise. They do not react to every piece of feedback. They stay curious but resist overcorrecting.

One founder I worked with was told by an investor that there was no room in the market for what he was building. He felt disappointed for a moment, then shrugged and said, “I just need to find the right investor who believes as much as I do.”

Inside big companies, we are constantly judged by peers, managers, and executives. We tailor our messages to keep as many people happy as possible. Founders cannot do that. They need a vision and the persistence to keep going, even when few people agree.

And often, it is not the first mover who wins. Zoom was not the first company to tackle video meetings. WhatsApp was not the first messaging app. OpenAI was not the first company to build large language models. Success often comes to the one who keeps going, not just the one who arrives first.

Attracting Great Talent

The best founders know their most important job: recruiting. People want to work with A players, and the best founders are the ones who can bring those people in. They are evangelists and visionaries. They can see the future, but they also know how to build the team that will take them there.

One founder told me that recruiting felt like his full-time job. And that was exactly how it should be. I agree. You are only as good as the team you put on the field. The right hires can change a company’s trajectory. The wrong ones can stop it in its tracks.

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Founders live by the river, where the currents are unpredictable and where opportunity and danger are often the same thing. Watching them has taught me that the ones who thrive there are the ones who build extraordinary companies. For the rest of us, their lessons are a reminder that while we may choose the village, carrying a bit of that river energy can change the way we lead, grow, and build. Sometimes, that is what turns an ordinary career into something remarkable.