Outlier’s Path

Having spent more than a decade as an operator at LinkExchange, Tellme Networks, and Zappos, and then the last decade representing Sequoia on the boards of some exceptional and legendary companies, I have learned much from outlier founders.

In the past few weeks, I’ve spoken with several founders about how much AI coding tools are creating enormous leverage for the people who actually take the time to master them. We need new frameworks for development. Waterfall was used for the mainframe and PC era and gave way to agile in the internet and […]

This past Friday, I posted on X: “As a founder, you can get a lot of things wrong. But if you’re unwilling to die, it will eventually work out…Be optimistic, and try to be right. But even if you’re not right, don’t die.” I expected modest engagement. Instead, it struck a nerve. Many founders reached […]

Ravi Gupta’s office is sparsely decorated, with a single handwritten index card on his desk that reads: “Bring Joy.” It is simple, almost austere, but deliberate. This past week, Alysa Liu returned to the Olympic stage, skating with unmistakable joy, radiating it to admirers around the world, and winning gold. Growing up, my family dutifully […]

My son, who spends his free time on YouTube and Netflix, recently asked me why Blockbuster disappeared. To him, the idea of driving somewhere to rent a movie and then driving back the next day to return it sounded almost fictional. I tried to explain the joy of wandering the aisles, the serendipity of stumbling […]

At a young age, my parents often complained about how fearless I was and the trouble it caused. There were bumps, bruises, and more than a few trips to the emergency room. There was this one time (and no, not at band camp) when I climbed to the top of a dresser and jumped off, […]

I’ve spent most of my life working in tech and largely ignored the haters. I started building clone PCs in junior high to fund my obsession with nerdy gadgets, back when being “into tech” was decidedly uncool. In high school and college, many people went out of their way to avoid the techy or nerd […]

In every company’s journey, founders feel pressure from investors, competitors, their team, and even themselves to capture more market share. It sounds rational. It sounds ambitious. It sounds like progress. Market share becomes a convenient scoreboard: simple to track, simple to compare, and dangerously simple to misunderstand. History is full of companies that numerically dominated […]

Recently, Nueva (my son’s school) rented The Guild, and each grade assembled a band to perform on stage. My son’s group called themselves the Imagined Order. Before they performed, they stepped up to the mic and explained the supposed origin of their name. They had read Sapiens last year, loved the chapter titled “Imagined Order,” […]

During Thanksgiving Break, I found joy at several friends’ and family gatherings. I’ve learned to sit between the adults’ table and the kids’ table. The conversations at that intersection are always more interesting. The adults bring experience. The kids bring possibilities. Together, they create a broader aperture of the world. This year, AI and our […]

Stripe Press has earned wide praise for its mission and the quality of its books. They are beautifully designed to speak to the “innately curious, to “the tinkerers and builders” drawn to ideas that challenge and provoke. After browsing their site, I ended up buying almost all of their titles. Over the weekend, I found […]