Imagine you logged the outcome of many casino visits where you played roulette until you were up at least $20 or lost $1500. You would naturally end up leaving ahead most of the time, and occasionally would lose a lot. Here’s one possible outcome over 100 casino visits: As expected, most times you win a small amount, and occasionally—3 times in this case—you lose a lot. You want to improve your system, so try to figure out how to avoid those big losing days... (more) →

Governments, and thus us as upstanding Homo politicus beings, are accustomed to thinking about common infrastructure: organizations and structures that promote further wealth-building, but don’t always have a natural market-based mechanism to exist. We can think about them as “resource enablers”, providing economic benefit while being agnostic about value capture. Not all of these are anti-market. For example, the electrical grid facilitates nearly the entire modern economy, and charges roughly the cost of production instead of value. We have a ton of these: communications networks, safety regulations, clean air/water infrastructure, sewage and sanitation systems, environmental productions, vaccination programs, financial regulatory frameworks, and the public postal system... (more) →

I once read a book that shattered my core. It was beautiful, effectively breaking down and building up my model of the world. Without hyperbole, how I viewed my place among others changed such that many of my life perspectives before this book seem adolescent. Naturally, I became a That Book evangelist, telling everyone I knew about how good the book was. It was long, yes, but be patient — it’ll change the way you see the world. I won’t tell you what it was, the reception was less enthusiastic... (more) →

We’re accustomed to social network dangers: doomscrolling, the media feedback loop, polarization, etc. Their currency is attention, and thus are naturally designed to addict by providing spaced dopamine hits. Many social networks also have incredible value, but self-control in the moment fails. Instead, it’s up to you to control them so that you pick what you get out of them. I’ve spent the past several years building systems to maximize social network value, while minimizing natural feedback loops. I’ll start with YouTube, which I consider the most valuable social network to have ever existed... (more) →

My default disposition is fairly rationalist—or at least, rationalist-informed—and have a gut distaste towards “the woo”. I also have plenty of curiosity and believe that wisdom is often lossily encoded in culture, so have tried and experienced quite a few things that I initially met with a wave of skepticism. Many have become significantly meaningful in my life. Scientific reductionism is the modus operandi of thought in Western, educated circles. For it’s flaws, this approach has pushed the boundaries of our knowledge of how the world works, but consistently has blindspots between domains, with significant consequences... (more) →

Angel investing is—for most people—a bad investment. As such, accreditation is rarely the limiting factor to being able to realize outsized investment returns, because variance is incredibly high while median performance is tepid. However, it can have very net positive externalities that include networking opportunities, learning about venture, getting involved in exciting companies, and honing your startup skillset. If you’re interested in angel investing, but don’t yet have a portfolio large enough to support diversified meaningful bets, there’s a few options to start down this path and capture a lot of the value you’re after... (more) →

For several years, I’ve developed a strategy that I use to stay on top of all my personal and work projects, while not getting overwhelmed by infinitely-growing lists. Using this strategy, I’m able to regularly surprise people about how I remembered to do some passing request they had, and am able to bring back concepts after weeks of dormancy. It’s quite simple, and adaptable to many different tools. Guiding Principles: When a task arises, it’s hard to know the absolute priority and allocate time effectively... (more) →

Eric Bahn, general partner at Hustle Fund, gave a talk about pitching investors, focusing on pre-seed/seed companies. Here’s my editorialized notes of his talk. .. (more) →