(I wrote a prior version of this post a few years ago. As my thinking has evolved, felt it’s time for a more current version).

1. The scarcest thing in the game of startups and venture capital is the force of nature founder who can will a company into durable success.

2. Building a company to scale over a decade is very, very hard. Someone can gamify the venture game for a couple of years to get high valuations but you can’t hype your way to $200M+ in revenue with high gross margins and a high growth path ahead. A lot of things need to go right beyond getting to product-market fit. A LOT of navigation needed over a decade-long timeframe.

3. Since startup success is such an improbable outcome, I need to invest in founders who are capable of improbable outcomes. We use this specific phrase because it makes our internal deliberations more pointed and aware of the uphill journey ahead. Most of our internal discussion and diligence post first meeting is focused on - is this person capable of improbable outcomes? (More to come in a later post on this specific point).

4. A question that deserves more attention than it gets from founders when evaluating an idea: is there urgency at the buyer’s end to solve this problem?

5. Market sizing a specific use case in a rising tide is a futile exercise. Better to be betting that this founder pointed at this market is something I'm very excited about.

6. Earlier in my VC career, I used to think a lot about structural moats. What I realized over the years is: structural moats mostly (only?) exist at scale. What comes before, and often is the moat itself, is the founder’s ability to create an org that relentlessly executes (on both product and distribution). I now spend much less time thinking about defensibility and more asking questions on differentiation and accumulating advantages.

7. Product-market-fit can be a fleeting thing if you don’t have the right team to scale the company around that PMF. In the words of Vinod Khosla - “The team you build is the company you build”. Probably the best startup advice ever.

8. Recruiting an A+ team is way harder than people think. It’s a multi-faceted problem: need to find a pipeline of high quality talent for each role to be filled, need to filter through the folks who can interview well vs. the real deals, need to close them. None of these is easy. You miss on any of these steps, you will end up with a sub-optimal outcome. Recruiting a strong team needs both intentionality and relentlessness on each of these steps.

9. A DNA of urgency and moving fast constantly has multiplicative positive impact at startups. As Sam Altman says: “Move faster. Slowness anywhere justifies slowness everywhere.”

10. In VC investing, rules and frameworks are useful but only if you also know when to break those rules. The next outlier will not check all the boxes that were put together based on the last 20 outliers.