Hi, I’m Taylor Pearson

Welcome to my home on the interwebz.

I have spent the last decade researching and writing about how you can better invest your time and money in an uncertain world. In geek speak, how to be more antifragile.

Over 31,704 founders, investors, business owners, and executives subscribe to my Interesting Times newsletter on how to make better decisions in a complex world.

If you’re interested in joining them, you can sign up here or browse my most popular essays to learn more.

I was a principal at a long volatility and tail risk focused hedge fund, as well as the author of The End of Jobs. My work has been featured in dozens of media outlets such as NBC, Inc, and The Financial Times. I live in Austin, TX.

If you’d like to say hello, I’m on Twitter.

What I’m Up To Now…

• I’m researching portfolio construction, trend following, long volatility and tail risk.
• I publish my research as essays and in my Interesting Times newsletter.
• I advise and invest in small businesses and startups. Primarily, my work is with internet-based cashflow businesses ($500k-$5 Million revenue) and seed-stage startups.
• My current interests include investing in small businesses (micro private equity), bitcoin/blockchain, complexity science, and volatility investing. (If you can recommend any events, books, resources etc in these areas, please drop me a note at taylor@this URL!)
• I’m not very good, but I play a lot of golf (down for a round if you’re in Austin!)

Updated September, 2024

The Long Version

How can you better invest your time and money in the face of uncertainty?

How can you become more antifragile?

All we are is investors. We invest our time, our money, and our energy.

Our lives are the sum of our investments – job investments, health investments, and relationship investments. How and with whom we make those investments determines the quality of our lives.

The job of investors is the same as the job of an entrepreneur: to move resources from a lower area of yield to a higher area of yield. Lower and higher need not be viewed in purely economic terms (though they can be), but also in human terms.

How can we be our higher selves? How can we invest in ourselves, our families, our communities and our humanity in a way that makes the collective better?

Antifragility is a word for things that benefit from disorder. They thrive and grow when exposed to volatility, randomness, disorder. They love adventure, risk, and uncertainty.

Antifragility is behind everything that has changed and survived with time. This includes biological evolution to technological innovation to cultural and economic success.

The world we live in is growing more complex and uncertain every day. We must make better decisions about how to invest our time and money in the face of uncertainty. But how?

The 2008 financial crisis was the trigger for me of how important it was for us to build more antifragile systems. It was the year many retirees or near-retirees had to rethink their futures. Many people in what they thought were stable jobs and career paths found out that those jobs weren’t so stable.

My belief at the time was that thoughtful experts captained the world around us. The 2008 financial crisis made it seem no one was at the wheel. No one knew what they were doing. How did something as insignificant and esoteric as an underwriting error in the U.S. housing market bring the global economy to its knees? And how did almost nobody see it coming?

I remember the moment when it clicked for me. I was reading Nassim Taleb’s book Fooled by Randomness on an old blue couch I’d bought for $100 off Craigslist. In his books, Taleb argues that humans tend to create environments where extreme events are more likely. They then use incorrect models and bad assumptions which leave them exposed to large, unpredictable black swan events.

It became clear to me that we had to reimagine the way our models view the world in a fundamental way. We must build more robust, if not antifragile, systems.

There was a small little corner of the world that had come to a similar conclusion and was attempting to study it. The core idea comes presented in many forms including: antifragility, black swans, complex systems science and ergodicity. They all take similar approaches and reach similar conclusions.

Understanding the logic of this new world view is a fundamental skill for our time. To be successful as a developer, designer, marketer, CEO, or investor, you must understand how to become more antifragile.

I first started writing this site on the weekends to detail what I was learning. The first time it got any meaningful amount of attention was when I posted my notes from Nassim Taleb’s book, Antifragile. The concepts in the book were fascinating and all dealt with how to better deal with uncertainty. Yet, there wasn’t much in the way of applications.

In 2015, I wrote and published a book, The End of Jobs. It showed how to make your career more antifragile. It looked at ways in which the world of work was becoming more uncertain, but also more full of opportunity. How can individuals leverage technological change to have more freedom and control over their lives and careers?

My essay on Antifragile Planning looked at how we could apply complex systems thinking to our own productivity. Instead of rigidly defined plans, knowledge workers today need flexibility. I turned this article into a popular course with over a thousand alumni today.

I studied how business owners could apply this type of thinking to grow their business. I published what I had learned in essays including Focus on the Fat Tails and Jesus Marketing. I used this antifragile approach to grow an eCommerce startup in California by 527% in 18 months and to sell tens of thousands of copies of my book.

My consulting work with startups lead to research on Scaling and The Business Production Function. I looked at how entrepreneurs and executives could build more antifragile companies. Companies that grew quickly, while still being robust, if not antifragile.

I dove into the work of John Boyd, a military strategist who pioneered the OODA Loop, a framework for winning in a complex world.

I started researching how to apply this antifragile mindset to investing.

One outgrowth of this was a deepening interest and research on Bitcoin. In my research, I saw that Bitcoin exhibited interesting antifragile properties. The financial system that created the 2008 economic meltdown appeared centralized and fragile. Bitcoin’s design was far more decentralized and robust.

Yet, from an investor’s perspective, Bitcoin remains a speculative and unproven asset.

And so I set out to see if I could actually build an investment strategy in traditional financial markets. I partnered with an investor with twenty years of experience in markets and an award-winning investment firm managing billions of dollars. Out of that process, a hedge fund was born which I ran for five years.

Over 31,704 founders, investors, business owners, and executives subscribe to my Interesting Times newsletter to get research-backed systems on how to make better decisions in an uncertain world, and, in so doing, make themselves more antifragile.

If you’re interested in joining them, you can sign up here or browse my most popular essays to learn more.