📶 99 brutally honest takeaways from working in venture capital

Our updated list of non-obvious things we've noticed

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Good morning 👋

I published my list of 50 takeaways about working in venture capital around this time last year.

It’s still the most popular piece of content we’ve ever shared.

Here’s an updated version of that list with more things I’ve learned or noticed over the past year.

If you think I’m right, wrong, or anything in here resonates with you, let me know in the comments.


  1. There are not enough good companies out there to justify the amount of venture funds in existence.

  1. It used to be a requirement for VCs to have company-building experience, but that has gone away as more funds have popped up. The advice you get from most VCs today is based on something they read and not personal anecdotes. Do not take this advice as gospel.

  1. The best founders spend the least time fundraising. If you make your diligence process a burden on the founder, you’ll have to settle for bottom-tier deals.

  1. VC Twitter is the worst place on the internet. Avoid unless you want to lose brain cells.

  1. You'll constantly hear the line "Where can I be helpful?" Most people cannot offer you help. Accept this, and move on.

  1. The most interesting investors I’ve met have the most unique backgrounds. Not saying it’s impossible to become a great investor by following the standard path, but more lived experiences equate to broader mental models. On that note, if you want to be more interesting, do interesting stuff outside of work.

  1. Everybody in VC claims to want to be your friend. It's up to you to figure out a) who you want to work with and b) who you can actually do business with.

  1. It is way easier to 3x your money at a $10mm fund than it is at a $100mm fund. It is also way easier to 3x your money at a $100m fund it is at a $1b fund.

  1. Over the past five years, I’ve known many funds that have invested based off of hype alone. No diligence, no reference calls, no thought out thesis - only an expectation that somebody else will bid higher in 12-18 months. That is changing, but it still exists.

  1. The VC tech stack for nearly every fund is ironically horrible. Spreadsheets and email are the standard. The bar is low for being “tech-driven”.

  1. Building an audience is overrated. Building a skillset is underrated.

  1. You will not build any skills on the job as an analyst or associate at a venture capital fund (unless you consider outbound prospecting as a skill).

  1. Most junior VCs are glorified business development reps.

  1. The larger the fund, the more focused your job is on sourcing. The smaller the fund, the more you'll have to be a jack-of-all-trades.

  1. Proprietary deal flow is a myth.

  1. You can raise a fund on influence, but it is very hard to scale one on clout alone (Ashton Kusher + The Chainsmokers are a few of the only ones that have proven this wrong).

  1. “Partner track” roles are not as popular as you’re led to believe. Most analyst / associate roles are two-year positions, then you're expected to find something else after that (preferably joining a portfolio company or starting your own company).

  1. If you earn carry at your fund, consider yourself lucky. 90% of junior VCs get no upside for their work.

  1. If you want to be rich, working as an employee in VC is one of the worst fields to do that.

  1. If you want to work directly with founders, you’re better off joining an actual startup. Your involvement with the founding team will peak during the diligence process, and then it will wane off from there.

  1. Selling a product or service to VCs is incredibly difficult. These people are some of the most selective people in the world, and they say "no" for a living. If these are your target customers, de-risk your business by selling to another audience.

  1. Venture capital rewards being solely focused on your job for long periods of time. If you have any plans of being multi-faceted and not obsessed with your work, there are better careers for you.

  1. Spray-and-pray seed funds do more harm than good to companies that require large amounts of capital. If a fund isn’t able to follow on into your next round of funding, it sends a bad signal to other investors.

  1. Most VCs are extremely lonely in their day-to-day. Small teams and saying “no” all day will do this to you.

  1. Venture capital is an apprenticeship game. Because of this, you’ll be expected to be in the office to get facetime. It’s tough to find roles that are open to remote work.

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