The Paradox of Ambition

In Silicon Valley, ambition matters more than financial success.

The interestingness of your ideas matters more than the size of your bank account. The culture is built to support companies and entrepreneurs who want to pursue moonshot ideas.

Silicon Valley culture is a perspective shift. In school, it helps to fit in. In the Valley, it helps to stand out. Where school teaches you to pursue guaranteed success, the Valley teaches you to pursue projects with exponential upside; where school teaches you to follow the rules, the Valley teaches you to ignore them carefully; and where school teaches you to pursue well-defined targets, the Valley teaches you to pursue lucrative goals that others can’t see.

The wilder your target, the easier it is to find your place in the Valley. The motto is simple: If you want to thrive in Silicon Valley, raise your ambitions.

The Paradox of Ambition

Ambition is a paradox. We’re taught that hard goals are hard and easy goals are easy. In entrepreneurial environments, the inverse is true. Paradoxically, hard goals can be easier to accomplish.

Ambition is like free money. The more you have, the faster you can progress.

Elon Musk understands the paradox of ambition better than anybody. His ideas are so ambitious that employees will move across the country or take a pay cut to be involved. Likewise, investors will invest at higher revenue multiples, and journalists will write about the company because they know their Elon Musk profiles attract clicks.

In that way, ambition is a virtuous cycle. The more you have, the more you succeed, and the more you succeed, the higher your ambitions become.

But before we move on, I’d like to qualify my thesis. Ambitious projects are much more likely to attract support if they improve the world. They can’t be trivial, and they certainly can’t be evil. They should be distinct, innovative, and inspiring.


Personal Introductions

Moments of tremendous progress often come down to the quality of a first impression. You meet an investor, and they make a large seed investment. Or perhaps, you meet a big-name journalist who writes a profile of you in the New York Times.

No matter the opportunity, moments of serendipity begin with accelerating heartbeats. The strength of a memory is tied to emotion. Ambitious ideas are easy to remember because they raise the hairs on the listener’s skin. Novelty helps too. If you share an ambitious, mind-expanding idea, your chance of attracting support skyrockets.

Ambition inverts the calculus of personal introductions.


When you make a social introduction, you put your reputation on the line. You burn some hard-earned social capital in the name of doing a favor for a friend. But when you make an introduction for a talented and ambitious friend, the calculus flips.

It’s cool to know ambitious people. Rather than lowering your status, making an introduction for an ambitious friend can raise it. Instead of taking somebody else’s time, people see you as “in the know.” And if ambitious people hang around you, then you must be doing something right. The more you work on ambitious projects, the easier it is to meet the people you want to meet.

I recently hosted a 19-year-old kid from Ireland at my apartment in New York City. Jeff found me through my newsletter and cold emailed me last year. He was visiting New York and asked me to dinner. Based on the quality of his cold email, I said yes.

While dining over a Margarita pizza on the Lower East Side, he told me that he built a nuclear fusion reactor in his dad’s basement when he was 15 years old. To do it, he studied explored high vacuum equipment, high voltage electronics, neutron detection, and plasma physics.

Hearing his story widened my eyes and raised my heartbeat. In the weeks that followed, I encouraged him to apply for a handful of grants. Speaking over WhatsApp, I helped him refine his story and raise his ambitions. Six months later and I’m proud to report that he received every grant he applied for.

As part of the Emergent Ventures grant, Jeff recently visited Silicon Valley. Based on his story and a handful of cold emails, he met some of the biggest names for coffee, including Patrick Collision and Daniel Gross. Another person he met on Twitter was so inspired by his story that he introduced him to Sam Altman, the Chairman of Y-Combinator.

As he said to me with a wink: “Not bad for a rural kid from Western Ireland.”

Lessons from Stripe

Of all the companies in Silicon Valley, Stripe has raised the status of ambition the most.

The ambition flows from the top. I once read that Stripe CEO Patrick Collision ends every meeting by asking two questions:

  1. Is this the most ambitious plan you could come up with?

  2. What would you propose if you had unlimited resources?

Based on conversations with friends who work there, Collison’s questions have rippled through the organization. The leadership begins at the top. In recent years, the company’s has increased its ambitions from building a world-class payments processor to “Increasing the GDP of the Internet.”

As Mark McGranaghan, an employee at Stripe, wrote:

“Stripe’s insight was that tackling ambitious problems doesn’t just make the potential prize bigger. Ambitious efforts are often more feasible than smaller ones, because the strongest people want to work on the most ambitious efforts. In our experience this positive talent effect was stronger than the negative effect of problem difficulty. So, paradoxically, tackling a bigger problem could be both more rewarding for the company and in a sense more tractable.”

Stripe runs on the Paradox of Ambition.

In the software industry, recruiting is hard, but very important. The best engineers are 10-100 times better than average ones, and in Silicon Valley, the best ones leave sexy companies for even sexier ones.They want to work on hard and energizing problems that impress their friends and families. Therefore, the more ambitious the vision, the easier it is to build and recruit the best software engineers.

Raising the Level of Ambition in Society

We should raise the level of ambition in society.

Ambition is a non-rivalrous good. Consider a car. If I own a car and I give it to you, I no longer own the car.

But ambition works the opposite way. It’s positive-sum. We can both have more ambition. That’s why ambitious people attract other ambitious people like an N52 magnet. Better yet, when two people with inspiring ambitions meet, they can support each other and pursue their ambitions in tandem.

Instead of exhibiting diminishing returns, raising the level of ambition in society has increasing returns. I’m reminded of a quote from Tyler Cowen:

“At critical moments in time, you can raise the aspirations of other people significantly, especially when they are relatively young, simply by suggesting they do something better or more ambitious than what they might have in mind. It costs you relatively little to do this, but the benefit to them, and to the broader world may be enormous.”

Ambition is a self-fulfilling prophecy. Raise your sights and waltz along the fine line between impossible and transformative. If your heartbeat is rising, you’re doing it right.

Learn from Silicon Valley and take advantage of the Paradox of Ambition.