One year after joining Khosla Ventures I felt totally lost.
I was used to insanely long hours and high expectations from my time in private equity at Silver Lake. I was used to chaos and rapid changes of direction from my time at Square during its hypergrowth phase. But I was not used to having near total freedom to spend my time however I thought most valuable.
That may sound surprising: why, as a junior member of the investment team at a Sand Hill Road venture capital fund, did I have such an unbounded role? Isn’t the whole point to work your way up the ladder to become a Partner?
It’s because before I even joined the firm I was knew there was no promotion in my role — no ladder to climb. The Associates and Principals who preceded me started incredibly successful companies after their time there but they did not get promoted to Partner.
The Tyranny of Freedom
Vinod, to his eternal credit, is a straight shooter. He made his expectations clear during my final interview: I would be at the firm for a few years then I would either start a company or join one of the startups in the portfolio. The role was a 3-year paid apprenticeship in startups and my job was to learn as much as possible, then leave and apply that knowledge. While I was there I was expected to do the leg work for Partners in analyzing, making, and supporting investments, but as long as I kept up it was up to me to maximize the rest of my time.
Vinod knew what he was doing. My role at Khosla Ventures was preparing me for the ambiguity and structurelessness of entrepreneurship. I no longer had a set of expectations to meet for promotion or a clear example of what “doing a good job” looked like. Helping the partners was table stakes; actual success was entirely up to me. I had to create it myself, on my own terms. It was like preparing a thesis with no set word count.
If no one is telling you what to do or shaping what you aim for, how do you figure out how to spend your time?
Starting With an Experiment
One Friday morning the fall after I joined Khosla Ventures, I walked 10 minutes to my favorite coffee shop with nothing but my wallet, a Moleskine, and pen. I ordered a cappuccino, sat down, and journaled on four simple questions:
- What is my goal?
- What did I do, or what experiments did I run, this week in pursuit of that goal, and what did I learn?
- Will my goal next week remain the same, or will it evolve?
- What are the 3 most impactful things I can do next week?
The purpose of the exercise was simple: to create a system to give me feedback and ensure I was always making some kind of progress. Every week I would learn something. Sometimes I learned I needed a more specific goal. Other times I learned that I needed to dig deeper on my current path. And still others I found myself hitting a dead end and needing to reverse up my decision tree a few steps to pursue a different direction. But no matter what, the simple, steady drum beat of this routine ensured that I was always progressing.
This is the problem entrepreneurs encounter every day. A company is not built in a week, but ultimately it is the steady accumulation of week after week of work, relentlessly compounding.
By the end of my time at Khosla Ventures two years later, I had helped incubate 2 companies that achieved 9-figure valuations and was in the process of germinating a third.
Why This Works
What began as a simple experiment turned into an essential tool I use with every founder I coach. I even use it with my partner. Why does it work?
- It’s a ritual. Do it at the same time every week and choose a setting that creates physical separation from your normal day-to-day life. The routine makes it easier to commit to and make a habit, and the destination frees you from existing mental patterns, creating space for mindfulness and creativity.
- It’s simple and clear. It’s four questions that result in three crystal-clear priorities. I tried out dozens of permutations and found that deeper analysis didn’t yield better results. The output is stark: just three things to do in a week — the three things that you know matter the absolute most. You’re either doing them or you’re not.
- It creates accountability and momentum. Every week you’re confronted with a visceral reminder of whether you did what you said you would do. If you do what you said you would, you’re guaranteed to learn something — and learning is progress, regardless of whether the outcome was positive or negative from the perspective of achieving your intended goal. A negative outcome is just an opportunity to adapt your course. And if you didn’t do what you said you would, you’re confronted with something different: why didn’t I do it? The answer to that may yet be revealing: maybe you’re avoiding confronting something (e.g. a fear of failure), or maybe you’re pursuing the wrong goal entirely. You can invert the exercise and turn it into — “If what I did this week was reflective of my goals, then what does that imply my goal actually is?” No matter the outcome, you won’t remain stuck for long.
Every week you can learn something about your journey, and every week offers an opportunity to course-correct and continue moving. Even if you feel stagnant, there’s still a written record of how far you’ve actually come.
Small Habits, Big Outcomes
While one week’s work may not feel like a lot, nothing meaningful was ever built without stacking single weeks of not-miraculous work on top of one another. A surprising amount of success is just showing up: simple steps, executed repeatedly, compounding. It doesn’t actually take miracles — just persistence and intention.
One cappuccino a week is all it took to completely change my life. What can it do for you?