• Patrick O'Shaughnessy
  • September 18, 2018
    Read, recorded or researched
Patrick is the CEO of O’Shaughnessy Asset Management and founder/host of the popular business podcasts, Invest Like the Best and Founder’s Field Guide. He is also a co-founder of Colossus, a media company, and Positive Sum, an early stage VC fund.

The Best Points

Patrick O'Shaughnessy
Invest Like the Best


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Original experiences

Looking back on the guests I’ve had, I realize now the common mindset that unites them. Even though my guests have come from just about every conceivable background, investing and otherwise, they are all in persistent and consistent pursuit of original experience. I now think often: am I doing this because its conventional, or because I’m watching what other people do? I think if you do the same exercise, you’ll be alarmed by how often the answer is “yes.”

Deep curiosity

My take on curiosity after meeting all these people is that it works best in two ways: through building units of exploration, and through embracing strange intersections. I often see people using seemingly unrelated interested, ideas, or strategies together to produce something different. I encourage everyone to think about strange ways of combining their areas of expertise and interest.

Persistence through randomness

Sometimes when I talk with people about the importance of curiosity, they say it sounds easy and fun. The good news for the sceptics is that more often than not, it’s not fun, it is a total slog. The journey of discovery is often tedious, filled with dead ends, and above, totally random.

Risk management

It is tempting to view uncertainty as a sort of risk, but I think that is a large mistake. All the good stuff is found in places that haven’t been mapped already. In fact, to take the idea of original experience a step further, what is common across the best people I’ve met is not just having the experiences, but then bringing some sort of order to the chaos they found in uncertainty. Many of my guests have a clear focus on downside risk protection. Several people have told me that there are common ways that things go wrong, but many more unknowable reasons things go right. So instead of trying to predict what will work, focus on avoiding the common pitfalls.

Trail magic

What hikers call the acts of kindness and goodwill bestowed upon them by strangers along their journey. Food, shelter, a quick lift, a homemade cookie. Consider how incredibly positive-sum trail magic is. The givers and the receivers of the magic both come out ahead.

Follow your own way, always

In summary. Figure out the right units of exploration, embrace strange intersections, and carefully consider what could go wrong. Rest when you need it, be dogged and aggressive when the situation calls for it, but just keep going. Do it all with respect for others and as much trail magic as you can muster.