25 years of investing distilled down to 3 minutes

I've been in the investment industry for nearly 25 years now and have learned a lot. Most of the lessons I have learned have come the hard way, as is the case with much of life.

Beginning in 2008, sitting in the middle of a disaster at a large investment bank, I started keeping a list of lessons I was learning about investing real time. Through the years, I've added to that list. Some of these come from mistakes I have made and some come from mistakes I've watched others make. The list arises from a collection of experiences that range from working on a NY trading desk to being a senior PM of a large global macro fund to running a large family office. I recently dusted the list off as a reminder and to also see what applied to the crypto space. I would argue almost all of it does. What do you think? Thought I'd share it with anyone who is interested. There's only 26 of them so it shouldn't take long to read!



  • I can’t see around corners and have significant doubts about those who think they can.

  • Math and history are useful guides but are incomplete without common sense.

  • In the long run, I believe humans + machines will get better results than either one alone.

  • Markets are reasonably efficient, most of the time.

  • There’s a difference between deal guys and investors.

  • Incentives affect human behavior-always.

  • The industry is great at figuring out how to repackage ideas that tripped up investors 1.5 generations ago.

  • Things work until they don’t. Sometimes they start working again.

  • For the most part, people are now throwing the same math at the same data.

  • Human emotions are a significant factor in the investment decision making process.

  • Tail risk is real, often underestimated, rarely prepared for, and highly catastrophic to long term goals.

  • Markets are forward looking.

  • Correlations are highly volatile, unpredictable, and backward looking. Treat them as unstable artifacts of history.

  • Investors, whether they know it or not, often have multiple goals.

  • I can’t call bottoms but am reasonably confident I know when there’s blood in the water.

  • I’d rather let others try to call the top.

  • Effective diversification is essential.

  • People often start talking about ‘over diversification’ at the end of a cycle, only to regret it later.

  • Having systems set up to minimize mistakes and encourage discipline is a good thing.

  • Risk needs to be diversified across different factor regimes.

  • Distributions are at least as important as averages.

  • Size is the enemy of great returns.

  • A mosaic, stepwise approach applied to the most important decisions usually pays off.

  • Great performance is damned hard work.

  • As long as fear and greed are part of the human condition, cycles will persist.

  • Be open to new ideas and innovation, as long as they don’t contradict anything on this list!

Have a great day!

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