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.

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 […]

If you are in the northern hemisphere, happy first day of summer! Today is also the summer solstice when the Earth’s north pole is at maximum tilt toward the Sun, resulting in the longest day and shortest night of the year for the northern hemisphere. This year, the exact moment is Friday, June 20th at […]

At Sequoia we are privileged to work with daring founders on a quest to put a dent in the universe. Tanay Tandon, founder & CEO of Athelas and CEO of Commure after the Commure/Athelas merger, is one such founder. He emailed his whole team the following and it was so good, I asked him for […]

At Sequoia, we frequently have a company of the week case study. The exercise usually starts by showing some financial information about a company and having everyone guess what the company is or some other facts about the company. There is always some story or point behind the exercise that we reveal afterwards. Here is […]

February is an early litmus test for the rest of the year. We discover we are reaching a new operating rhythm and executing at a higher gear, or we realize we have settled back into the habits we wanted to break, but haven’t figured out how. If you are on the former path, keep pushing forward. If you are on the latter route, your job is to break out of Groundhog Day.

While we were all locking down our 2025 plans in January, the most significant technological development came from DeepSeek. The future is undoubtedly bright, and we are only limited by our imaginations. While true, let’s not forget the lessons from Deepseek.

The best moments of life can be found within the lifelong learning or quest itself. It’s doing something so fulfilling that the work is its own reward. As we kick off 2025, may you be a late bloomer and find yourself on a meaningful and impossible quest.

Since joining Sequoia, I’ve heard many examples of using finite game thinking on infinite games. Remember that we play a combination of finite and infinite games on any given day. Apply the appropriate tools to each.