There's s story behind every entry on this list. I'm writing these down so that I hopefully don't repeat them.


  1. The job: make something people want. Like many engineers, I've screwed up the "people want" part by:
    • Trying to automate something (scheduling) when (a) the customer already had a low-tech workaround, or worse, (b) the process needed to be manual for specific reasons (e.g. an opportunity to sell)
    • Developing a great solution for an unimportant problem (What specific individual has this problem? Why is it important to them?)
  2. Tradespeople start from the work ("I'm a lawyer"); businesspeople start from the customer.
    • Trades: "How do I invoice more work?" Business: "How do I sell more product/service (at X margin)?" Note how the second doesn't assume you're doing the work yourself.
    • Pre-Internet, "business owner" was the better bet. Today, writers with 10,000 readers are earning millions/year without "owning" anything, while Main Street struggles to scratch out a living against Amazon.
  3. Democracy isn't conducive to fast decisions or rapid change—most entrepreneurial ventures. Strive for consensus, but prepare for disagreement, and make it clear who has the final say. Equal partnership/co-CEOs is usually trouble.

Management and work

  1. Letting people go is part of running a high-performance organization. Unless you're willing to drag the whole organization down, don't hire someone you won't be able to fire (e.g. family, friends).
  2. If you're equally excited about two opportunities, pick the one with the better people. You'll learn more, and good teams tend to stick together long after they've worked together.


  1. Around 2010, value investing was dominant—and made Buffett miss Amazon. It's still dominant in 2020, but cracks are showing.
  2. The ability to create new markets (new spending where none existed before) is rare, and valuable; I was too caught up in the numbers (the value paradigm) to see how much commerce Square and Stripe could unlock, how much Facebook would reshape communication, or how willing people would be to pay $1200 for a new iPhone.
  3. In Silicon Valley, picking the right place to work (especially in your 20s/30s) is ~10x as important as worrying about your 401(k).
  4. With few exceptions (e.g. structuring), originating creditors don't sell performing loans or leases. If it's for sale, look for the problem.

Money and status

  1. Poor and middle class people compete over money; the game changes when everyone's a millionaire.
    • Who's richer, Michael Jordan or the person who invented the COVID vaccine? Nobody cares.