Should I Pursue My Passion or Business?

What if they lead in opposite directions?

The best advice I ever received:

“Do what you love, in the place you love, with people you love,” said my friend Brad Feld. Since then, I have relentlessly chased this vision: leaving the company I founded, traveling, giving up most of what I own, and moving to San Francisco.

I came here to build a new company. But after wandering the hipster cafes of SOMA for 31 days meeting amazing people, I failed to find something I love. While I dreamt up ideas for a company, my personal passion tugged at me. I ignored it because I judged it to be too risky. Too impossible to consider. Too ambitious to be sane. For someone who has told thousands of entrepreneurs to follow their passions, my denial felt hypocritical.

“Is my pursuit of success stopping me from doing what makes me happy?” I wondered. So I sought to appease the heart. I figured if I spent a few days on it, I would find a reason to put it aside for good and get back to starting a company.

I met up with Y Combinator partner Adora Cheung with a few ideas to help her project. An hour later, I walked out with my heart overflowing with hope and my mind filled with ideas. Unfortunately, I’m still an idealist.

For the next 6-months, I am joining YCombinator Research’s New Cities project as an Explorer. My goal? Create an open, repeatable system for rapid cityforming that maximize human potential. It is a vastness and complex challenge — and one that makes me so happy that I want to tap dance to work. Like any other epic journey, we’ll start small and learn fast.

I am not giving up entrepreneurship. This is just another form. I am trusting that amazing experiences will teach me to be a better entrepreneur.

I can’t do this alone. YC can’t do this alone. This is our problem to solve together. To be successful, we’ll need investors, industries, governments, charities, citizens, and critics. I know many of you have been waiting for a project like this. (If you have lots of land for a new city, let us know.)

Why now?

I’m done complaining about cities. I want to be a part of a solution. I want cities for the poor and the rich, the locals and the transplants, the freaks and the geeks, and the young and old.

Marina Bay Sands Hotel in Singapore: A thriving city-state.

Housing prices in urban environments have skyrocketed due to poor policy decisions and NIMBY-ism. Because cities are so expensive, we live far away and drive for hours, contributing to climate change and trade in our quality of life. Generations of Americans are unable to live in cities that can harness their amazing creative and intellectual potential. Exorbitant housing empties the middle class and drives record-breaking inequality. That’s just in the United States.

65.3 million people around the world have been displaced from their homes due to conflict and persecution. Once middle class, future Syrian refugees face the prospect of being born, raised, married, and having their own kids in squalid refugee camps. (We’re headed to Jordan to visit the Zaatari Refugee Camp in November.) Central American families are risking their lives to seek asylum at the US border because they are being threatened with death by gangs at home. And this is just the tip of a melting iceberg compared to the human displacement and suffering climate change can create.

The benefits of a healthy, affordable city are undisputed. Density drives up productivity. Walkable cities improve health. Urban dwellers release 20% less carbon. Access to education improves. Lifespans go up — particularly in developing countries. And there’s no shortage of space to build new cities. The US is still mostly rural, and globally, less than 3% of land is urbanized. As a bonus, increasing city density keeps rural lands rural. Everyone wins. Affordable, dynamic cities are a sustainable solution to a world thirsting for innovation.

Shibuya Crossing. The busiest (and orderly) intersection in the world. Tokyo, Japan.

And cities are resilient. Rome. Tokyo. Istanbul. Lagos. Cities often outlast kings and empires. City-states were the original superpowers. Yet, mass migration to mega-cities have only occurred in the last 50 years. Cities are young trees of life that have just started to bear fruit.

Every great city benefited from historically advantageous starting conditions that cannot be recreated. But I believe technology can seed fertile starting condition across nations and geographies.

What got us here won’t get us there. As technology advances, cities must adapt to new realities of life. Ancient towns were designed for beasts and wells. In the last century, cities were built for cars and concrete. Let me make an understatement: Changes are a comin’. People are challenging old ideas of what makes a great city and demanding a high quality of life and affordability. We can have both.

This is the biggest challenge I can find

Many will say it’s impossible and that our cities are too crowded, too dirty, and try to build a wall to shut out newcomers and auction off the best places. Many will wonder why a guy known for cat pictures and memes is running a project to build the cities of the future. I’m here not only to prove them wrong, but to include the naysayers in the future of improving our cities. We’ll kill skepticism with inclusion.

The problem-scape is vast. It’s difficult just to catalog and sort all the systems that a city needs to get started. To call a city a system or a platform underestimates the complexities. The size of the challenge excites me, and we’re putting options on the table.

My heart could not pass up an idea whose time has come.

I ❤ Cities.