Entrepreneurship
I am the son of two entrepreneurs and grew up talking about entrepreneurship and business around the dinner table. When I was little, my brother and I would run lemonade stands outside of our house. In elementary school, I wrote book reports and did presentations on entrepreneurs for class projects.
I spent ten years building Uncharted, an entrepreneurial accelerator, before we sold it in 2022. We worked with hundreds of entrepreneurs and were our own startup: trying to figure out how to build a sustainable business with a world-class culture.
What has struck me most about entrepreneurship is how different it is from traditional school (I was never the best student and struggled to fit into the standard academic mold).
The rules of the classroom are sequential: first you study and only then are you evaluated.
The rules of entrepreneurship are dynamic: you learn by doing, by constantly iterating and testing and getting real-time feedback.
While traditional school is fundamentally about you and your knowledge, entrepreneurship is about the relationship between you and the world.
It invites each of us into a humble posture of continuous learning and curiosity. It reminds us that we are, like our businesses, constantly a work-in-progress.
If I learned anything as an entrepreneur and CEO, it's that being an entrepreneur is incompatible with being a perfectionist, but despite its imperfections and incompleteness, I see the process of building a company, a culture, and a team as a never-ending work of art.
Writing & Newsletters
At Uncharted, I started writing a monthly newsletter. It started small and was written right out of the inbox. Each month, I’d stare at a blank page and ask myself: what am I curious about this month?
Soon, themes emerged. I found myself writing about what I was learning as a CEO, reflections on entrepreneurship and leadership, technology, culture, climate change, social impact, and the future of work. At the end of every newsletter, I’d share something personal.
Looking back, carving out the space to write each month was one of the best things I’ve ever done, and I learned some powerful lessons:
Write for someone on the other side of the inbox.
Write content that’s worth a damn.
Pore over your words. Hold yourself to ultra-high standards.
Write with an uncommon honesty.
When they’re at their best, newsletters masquerade as emails, but they’re really products that solve problems and delight someone.
Over the years, a few companies asked me to ghost-write their newsletters for them, and I’ve slowly added clients. Today, I work only with brands I believe have something important to say to the world, and I focus on end-to-end newsletter-as-a-service: newsletter strategy, writing, producing, analytics, and growth.