90 days in, 30 lessons out

One of my favorite visualizations from Jack Butcher is the one above, expressing “Noise is what you say. Signal is what they remember.” If there’s anything I’ve heard the most over the last 90 days, it’s the importance of optimizing for high signal over noise.

Why is this important? One thing, the internet is massive. Over 4B people have access to the internet and millions of pieces of information is being distributed every day. We all have a part to play in consuming the right information that suits us as well as contribute to the betterment of the internet for others’ consumption. When you’re trying to find the highest signal information or trying to differentiate yourself on the internet amidst millions of people, the two important traits you practice are patience and consistency.

In an effort to distill my initial 90 days in venture into a concise list of 30 lessons, I reflected on conversations with the Greylock team, founders, and colleagues I’ve had the pleasure to work with and learn from so far. The following includes brief takes with the highest signal and resonance to my recent personal experiences.

Here’s to the next 90+. Thoughts, always welcome.

  1. Venture is as much a sport as it is a game, you are balancing competitiveness with participation - you can’t win if you don’t participate, and you can’t participate if you don’t win.
  2. Investing is dynamic. The market, spaces, and companies change too frequently for you not to be constantly tested. The requirement is to never rest on your laurels and be humble enough to know when change is needed to stay competitive.
  3. You’re either gaining altitude or losing altitude. Prioritize where you’re continuing to gain altitude on a founder and an opportunity.
  4. Oftentimes, the market matters more than the team. Some teams are so well-equipped to win a market, but they often pivot to make it truly work for them. In other cases, market trumps team. As Marc Andreessen once put it, “the market needs to be fulfilled and the market will be fulfilled, by the first viable product that comes along.”
  5. Companies often align to one, two, or all of the following: 1) attention and connection driver: company aims to capture or sustain attention, 2) market maker and shifter: company aims to help someone do something they already do, immensely better, 3) democratized utility: company is offering access to something that was difficult or inaccessible before.
  6. Put another way, there are two kinds of companies: 1) ideas that have a clear line of sight for monetization and market adoption e.g. enterprise SaaS 2) crazy ideas that just might work considering the team, vision, and passion you have for both of those things.
  7. For some business (like marketplaces), creating new supply that meets existing demand is where you see long-term defensibility. Take Airbnb - in the early days, investors were skeptical of the TAM, but the founding team had the right mindset to create new supply in order to grow the pie that didn’t exist yet.
  8. Founders typically have the best combination of the following: integrity (strong morals), gratitude (appreciative and humble), grit (execution power), and curiosity (knowledge and feedback seeker).
  9. Never underestimate the companies executing in the background (e.g. picks and shovels business). These can serve as the critical glue between best-in-class consumer experiences and stable, secure, and reliable data.
  10. Generationally awesome businesses ($1B+) are typically only as awesome as the market conditions that lead to opportunities for constant growth or re-invention.
  11. There’s no such thing as relying on your gut instinct in venture. There’s only objective evaluation (path to PMF, profitability) and founder market fit (expertise, passion, vision).
  12. There are two models of ownership: own a lot of something that doesn’t have any traction (high ownership, high risk) or own a small amount of something that has proven traction (low ownership, low risk).
  13. For a consumer business to scale, the winning strategy is to hone in on a clear, organic-first acquisition plan for profitable unit economics. A losing strategy is requiring tons of capital to acquire users that don’t scale as your company does.
  14. The best products are built with community in mind (aka product-led growth). Take software unicorns like Figma or Stripe to internet brands like Snapchat and Instagram, adoption started from the bottom-up. As expressed by Linda Lian from Common Room, “Many of the fastest-growing organizations today know that partnering with their community is critical to their ability to build a better product, have happier users, and grow faster.”
  15. As a founder, always be self-aware to know what your top 3 killer strengths are and hire for your weaknesses. As an investor, evaluate founders on their ability to articulate this well at the early stage and execute this well at a later stage.
  16. There are two reasons why startups fail 1) they grow too fast before reaching product market fit 2) they never reach product market fit.
  17. Growth can wait, survival cannot. You’ll often hear from investors that in today’s changing environment, focus on the core inputs of your business that will lead to maximum gains. Don’t scrutinize the output (public valuation) of which you have little control over.
  18. You’re only as smart relative to the smarter people you should constantly be surrounding yourself with (be it friends, mentors, colleagues). The best founders know that their company is a product of people, cultivated and strengthened by the brand and ethos of the company’s mission.
  19. When you’re trying to become an expert in a topic, go straight to the source - find the experts that are open and willing to educate you on their expertise. As you get further along in your career and give back by sharing your knowledge, your accessibility to experts will grow.
  20. Go deep on first principles and foundational knowledge. Pick one or two spaces and have substance. This could mean trying out being a creator to learn about the monetization model or minting an NFT to learn about crypto. Developing a network of experts is a shortcut to information, but not first-hand experience.
  21. Having empathy is incredibly important as both a founder and investor. As a founder, you’re stronger the more empathy you have with your users and customers. As an investor, you’re valuable the more empathy you have with the founder journey. Empathy is a both a trait and a practice.
  22. Conviction can be created over time vs in a single meeting as it is developed in tandem with building personal relationships with founders and investors.
  23. You will never really know what it’s like until you do it as there’s no substitute for first-hand experience. Whether it be investing, operating, or founding a company.
  24. As a VC, you’re constantly playing two critical roles 1) being a steward of capital to your LPs that are counting on you to make the right decisions 2) being in service to founders to build relationships and offer support and counsel.
  25. Your reputation is seeded with every new opportunity and managed closely by the ways in which you do good work, respect your peers, and provide value through shared knowledge and experience. It’s hard to build and easy to lose.
  26. Venture is about reducing signal to noise. Train yourself to be intentional about the opportunities you pursue based on objective first principles (ingenuity, market timing, team fit, technical advancements, retention) vs vanity metrics (marketing spend, short-term growth).
  27. Founding a company is an endeavor that will take 10+ years to fully come into fruition. When deciding what to focus in on, spend days, weeks, months, with the concept to experiment with what you’d like to spend the rest of your time on. Then fundraise as such to get it off the ground. Investors can only help you as much as they can relative to the progress you want to make in your company.
  28. The things you build show the dedication you have to a certain interest. Track record shows you’re putting your thoughts and ideas together and surfacing it to be tested in a public arena.
  29. The best way to evaluate product and company growth at every juncture is to know the core metrics to track and the milestones to achieve traction in each across each stage starting from seed to growth.
  30. The best investors are your partners - they not only understand your vision, but have a unique take on why your vision is the winning outcome. What’s more, they should be able to project out the trajectory of how you achieve milestones along the way and be equally excited and willing to partner with you on every step.
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