"To venture causes anxiety, but not to venture is to lose one’s self...and to venture in the highest sense is precisely to become conscious of one’s self."
In November 2013 I traveled to Morocco. I had just sold my company and survived thirteen challenging years of building four startups. I wanted to clear my head by picking a fight with something purely physical. I climbed to the top of Mt. Toubkal, sat on a rock, looked out over the clouds and listened to Eminem. It was one of the happiest moments I can remember.
I reflected upon the promise I’d made to myself when I was 21.
I had just returned from two years in rural Ecuador. It was there, living and working with people who were shackled by extreme poverty, that I decided to devote my life to improving the lives of others. I spent a lot of time thinking about how I could do it. I decided I would become an entrepreneur, build a successful business and retire by 30 with an abundance of resources and time.
Everyone has a plan until they get punched in the mouth (*Mike Tyson). My first startup was a small success, allowing me to pay for college. The second ended in flames…as did the third. By then, I had a young family to support and was going through some intense personal struggles.
I desperately needed money to pay bills and the people who had lent me money. I took the only gig I could land: a commission-only sales job selling credit card processing door-to-door. Shop owners complained about how they had been swindled and ignored in the past.
The industry was a mess. The technology was years behind and customers were plagued by complexity, unscrupulousness and terrible service. This was my opportunity. I was going to build a better solution.
The beauty and promise of entrepreneurship is that you get to author the world you live in. You determine the people you hire, the culture you create, the products you design and your reason for existence.
In January 2007, I founded Braintree. More than anything else, I wanted to build an enduring company with a soul—one that we all loved, one that was worthy of frequent love letters from our customers and one that would improve the industry. My team and I poured our hearts into the effort.
For the first five years, I bootstrapped the company. During this time, we acquired thousands of the world’s most discerning and disruptive companies as customers, including Uber, Airbnb, OpenTable, and GitHub, and we created the critical infrastructure to power the industry-wide shift to mobile commerce. We were twice named one of the fastest growing companies in America by Inc. Magazine. Our outspokenness and practices on price transparency and credit card data portability dramatically improved industry practices.
We acquired Venmo, and in 2013, eBay/PayPal bought Braintree for $800 million in cash.
I’d never worked so hard nor cared so much. No professional experience in my life has been as challenging or rewarding.
At 36, I finally achieved what I set out to do. After selling my company I began to meet other entrepreneurs. As I opened up and told my story—chaos, dreams and all—they told me theirs. I learned that many of them were going through the same things and had similar goals. I began working with entrepreneurs who had a shared vision about the world, and the OS Fund was born.
In October 2014, I launched the OS Fund—$100 million to invest in entrepreneurs and scientists who are working on quantum-leap discoveries that promise to rewrite the operating systems of life.
In the same way that a computer has an operating system at its core — dictating the way it works and serving as a foundation upon which all applications are built — everything in life has an operating system.
OS Fund companies are developing new solutions to fundamental problems and improving the lives of billions of people around the world for generations to come.