The Jack of All Trades

April 29, 2024

My whole life I’ve had a voracious appetite for learning. This manifests in a lot of different ways, but there is one in particular that I seem to share with a lot of other entrepreneurs.

​My friends used to describe me jokingly as a professional hobbyist.

​When something new catches my eye, whether it be a sport, a particular author, or a new skill, I go all in.

​Once something has my attention, I tend to become obsessed with learning everything I can, as fast as I can.

​Sometimes, the new obsession becomes a lifelong hobby, like when I first learned to snowboard when I was 13. 30 years later, I am just as in love, and still push myself to progress. My fascination has evolved over time, from being a park rider in my 20s to navigating the backcountry today, but there is always something interesting that keeps me coming back. The longevity of my love affair with snowboarding is, however, the marked exception rather than the rule.

More often, the story looks something like this:

  1. Try something new
  2. Enjoy it more than I thought
  3. Dabble for a month or two
  4. Unleash the beast
  5. Practice, study, and train with pro-level commitment
  6. Progress rapidly
  7. Reach some arbitrary level of success
  8. Reach a plateau
  9. Love fades
  10. Give it up forever

This cycle typically lasts anywhere from 6 months to 3 years, but almost never longer.

​When I read Tim Ferriss’s 4-Hour Chef (an oft-forgotten gem that may be my favorite), he nearly perfectly captured how I felt about learning new things—and even better, he gave a framework for doing so.

​And so, over the years, the list of once-loved hobbies gathering dust on the ash heap of my personal history is long and distinguished: wake surfing, Crossfit, road bike racing, bass guitar, aviation, Buddhism, meditation (currently on again!), theoretical physics, psychedelics, ping pong, pinball, car racing, cyclocross, biohacking, wine collecting, video games, whitewater paddle boarding, and a few others I can’t be bothered to remember.

Sometimes, I dust off a piece of forgotten equipment and give it a quick revisit, but even then, it’s often half-hearted and more nostalgic than anything else.

​From a neurochemical perspective, this pattern of diving deep and then moving on from hobbies makes total sense. As high performers, we often experience a powerful rush of dopamine—a key neurotransmitter associated with pleasure and learning—when we encounter new challenges or skills. This rush is particularly intense when the challenges align with personal passions or curiosity. Essentially, our brain rewards us for stepping out of our comfort zone and conquering unknown territories.

​However, as we continue to engage with the new hobby, what was once an invigorating challenge becomes more routine, and the learning curve flattens out. The initial surge of dopamine diminishes, and so does the engagement. This phenomenon is akin to a kind of “neurochemical conquest,” where once the thrill of the conquest wanes, so does the interest. It’s not merely a loss of interest — it’s a search for the next cognitive high.

​This pattern doesn’t indicate a lack of commitment or perseverance but rather a manifestation of a high-performance mindset. High performers are not just thrill-seekers; we are also efficiency seekers. We intuitively understand that the greatest gains in skills and abilities happen in the early stages of learning. Thus, our subconscious drives us to optimize our time and effort for maximum growth, which often means moving on once incremental gains require disproportionately high effort.

​The cycle of rapid engagement and disengagement also speaks to a deeper, perhaps evolutionary, trait of adaptability. By diversifying interests and skills, we essentially prepare ourselves for a wide array of challenges and opportunities. Many of the most distinguished historical thinkers were indeed polymaths – think Leonardo da Vinci, Isaac Newton, and Thomas Jefferson.

This pattern allows high performers to cross-pollinate ideas and skills between seemingly unrelated areas. For example, the strategic thinking developed in chess could enhance problem-solving skills needed in business, or the discipline from marathon training might translate into better focus during long projects at work. This transfer of skills often occurs subconsciously and is one of the unsung benefits of having varied interests.

However, there’s a flipside to consider.

​The constant pursuit of new interests can sometimes lead to a scattering of efforts that might hinder achieving mastery in one area.

​Put another way, our tendency toward distractions and quick wins comes at a price of excellence.

​When it comes to my investing career, I’ve seen the same pattern play out over the years.

​When I started investing outside of my primary business in 2013, I had no cohesive investment thesis or criteria. I had money, and all I knew was that I wanted to make more. My investment list reads a lot like my list of forgotten hobbies.

​From 2013 to 2021, I invested in early-stage tech, fintech, health tech, hard tech, crypto, commodities futures, SaaS, e-commerce, medical equipment, hotels/hospitality, oil & gas royalties, drilling oil wells, commercial real estate, residential real estate (LTR), short-term rentals, and even an automotive restoration company.

​It was not until a few years ago, when I was going through a significant crisisthat I realized my jack-of-all-trades strategy was costing me dearly. I was falling prey to the dopamine cycle and sabotaging my wealth in the process.

​When it comes to building wealth, we often hear that there is safety in diversification. The idea is that if you spread your dollars over enough investments, if any one fails, it won’t affect the overall performance of the portfolio.

​However, I’d argue that correlation risk is a bigger threat than concentration. If you diversify across many investments that are all susceptible to the same economic conditions, then you haven’t really diversified at all.

​For example, if the stock market crashes, history tells us that the real estate market isn’t far behind. Look no further than 2008: being equally spread between real estate and equities was an equally losing proposition.

​Instead, I believe that the best way for most of us to generate long-term wealth is to become experts in one specific area. For most of us, this would be our primary business. (Once we eventually sell, the problem becomes slightly different, but I believe the same principles still apply.)

​After all, we know our primary business inside and out—we are the experts. This should be our highest-leverage activity, our proven system to beat the market. A post-exit founder or professional investor should seek the same level of mastery. Find an investment thesis that works, validate it, and set forth on the path to 10,000 hours.

​Any investments we make outside of our primary expertise should have only one function: to create safety and hedge risk from our main efforts. For most business owners, this may be as simple as a basket of index funds or a fixed-income portfolio.

​I see so many founders taking time, resources, and effort that they could be applying to their primary skill and seeking alternative investments. I know because I used to be one of them.

What if it was as simple as focusing on your primary business and pouring any profits you make into one or two simple strategies? 

​I imagine many of us would buy a lot of time back.

​And so, as you consider your best path to wealth, it may serve to remember the plight of the proverbial jack of all trades:

He is a master of none.

​Diverse is worse,


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