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.

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 […]

In the last two weeks, I’ve been ruminating on a post from Sam Altman: “A thing often in common among great startup investors, founders, and researchers:Trading making a lot of small mistakes in exchange for getting a few giant wins.(Surprisingly many people seem to prefer a few big mistakes in exchange for a lot of […]

Pat and I sent the below this week to Team Sequoia. This is Our Sequoia. It has always been Our Sequoia. It was never Don’s Sequoia, nor Michael’s, Doug’s, Jim’s, or Roelof’s. From the very beginning—when Don chose to build a partnership and name it after the longest-living tree on Earth—Sequoia was meant to endure […]

On November 4, 2025, Sequoia announced that Pat Grady and I would be succeeding Roelof as Co-Stewards of Sequoia Capital. Before I met Roelof, I had heard stories about this remarkable CFO — the one who took PayPal public at just twenty-eight, sold it to eBay, and then joined Sequoia as a new partner. When […]

For the past three months, I’ve stepped away from my weekly ritual of writing before the start of the week. In that brief pause, the world of technology seemed to move at warp speed. We often say we live in an age of accelerating change. What we speak about today wasn’t even in our conversations […]

We want to believe that we are data-driven, logical, and rational. We are less so than we like to think. In particular, the tech industry is tribal, and Silicon Valley is a mecca for many religious leaders. People need to believe, belong, and behave consistently with their belief system and the tribe to which they […]

A reductionist investment framework involves reducing complex investment opportunities into a few variables: the size of the prize, the probability of success, the investment cost, and the time to exit. Most of us are very good at estimating the investment costs. For static investments, that’s simple. Even when there is some variable component, such as […]

In the last few weeks, I have observed how humans tend to be reductionists. We reduce our thoughts to an X post. We take a 500-page book and summarize it by its title. We take a whole CRM of customers and reduce them to a handful of personas. We make a detailed strategic plan and […]