Intellectual Capital

With the meteoric rise of cryptocurrencies and a new generation of crypto-millionaires, I keep thinking back to this epic tweetstorm by Sizhao Yang and how relevant it is for the rest of my life.

Financial capital comes and goes but intellectual capital retains forever.

The wrong mindset is to get caught up in the hype and dream about get-rich-quick scenarios. The right mindset is to remember to continue accumulating knowledge along the way.

Accumulating knowledge and the right mental models allow you to make the smartest decisions and invest in the right areas at the right time.

Even if you missed the crypto boat this time around (unlikely as all ships continue rising in this rising tide), investing in your mind and learning from this experience will pay off dividends in the future.


Learning Days

Most of my workweek tends to quickly fill up with sporadic founder meetings, company diligence, and portfolio company support. Rarely can I find the luxury of uninterrupted work blocks to sit for hours on end and properly study anything I want to learn.

In light of this year’s theme around deep work, I’ve been experimenting with the concept of “Learning Days” where I pick any topic I’m interested in and spend a full day (Saturdays or Sundays) deep-diving into that topic.

My first two learning days (Artificial Intelligence/Machine Learning & Blockchain) were relatively unstructured as I’m still figuring out the best approach to these going forward.

So far, I’ve kicked off each learning day in the following manner:

  1. Wake up and head to the gym for a run (a healthy body is a healthy mind)
  2. Shower and make tea
  3. Create a new Google Doc and throw it up on my second external monitor to document the day’s notes / learnings
  4. Look for a Medium article where someone has already aggregated the best links / resources for learning the topic of choice. For example, my buddy Sam DeBrule compiled a massive list of curated AI / ML links which drastically helped to cut down the time I needed to spend digging around the web.(obviously you’ll want to do your own research but these types of aggregated resources provide a launching point for mapping out what you know / don’t know)
  5. Go through each article I find: read and reflect. Each article should provide foundational knowledge for the next but I try to question / probe everything I’m reading. I want to develop a sense of which authors know what they’re talking about vs. those that are regurgitating information / filling my head with incorrect information.
  6. In my first hour, I try to first understand the history behind the topic (i.e. when and why did AI / ML first come into existence, what worked and what failed, what catalysts are leading to breakthroughs now)
  7. Now that I have better context around how we got to this point, I’m better able to understand the current state of AI / ML as well as map out a hierarchy of subtopics (i.e. AI -> Machine Learning -> Deep Learning -> Neural Networks) that I’ll need to prioritize my learning around for the next few hours
  8. For each subtopic, I try to understand: what it is (literally, what is deep learning), how it works (deep learning uses neural networks? ok, how do neural networks work?), and how it’s used in practical business / life (Google Photos uses deep learning for face recognition? much wow). I was never a great academic and this last part helps me tie concepts I’m learning to the “real world” so I don’t forget them.
  9. I’m also careful to include my source links next to all of my Google Doc notes so I can easily reference them at a later time.
  10. At the end of the day, I’ll revisit all of the raw notes I’ve taken and take some time to organize / structure them in a readable format – the hope is that someone completely foreign to the topic could pick up my notes and easily understand what I’ve learned that day
  11. As an additional forcing function, I’ve tried to “Feynman Technique” the whole process by teaching my significant other everything I’ve learned. Teaching the subject matter helps me quickly figure out which concepts or subtopics I need to spend more time on. It also helps that she likes to play the “why why why” question game which really forces me to simplify each complex concept. After teaching the topic, I have a list of follow-up questions for myself that I need to dig into since I couldn’t easily explain them.

I’ve got a long ways to go with these Learning Days but I’m loving them and they’ve spurred a new love of learning that makes me even more excited to wake up every morning.


Define Your Strike Zone

In one of my early middle school English classes, I had a seat next to the teacher’s desk where he had taped a poster of hockey athlete Wayne Gretzky and the quote “You miss 100% of the shots you never take.”

If I managed to submit a quiz early, I would lay my head down sideways on my desk and stare at that poster’s quote while waiting for the recess bell to chime.

At such a young age, my brain was especially malleable and I grew to embody that quote into everything that I did. There was no such thing as a fearful moment or a lost opportunity. Everything was a shot that I needed to take and there were no regrets.

Volunteer to present our projects in front of class? My hand was up first. Everyone scared to take the first leap while cliff-diving in Hawaii? My feet took control and I’d be the first over the cliff into the water.

That quote built an insatiable and intrinsic desire to always be pushing forward. Unfortunately, this desire also meant that I often had too many toes dipped in too many projects.

As a result, a finite amount of time and focus meant that I often lacked the ability to follow-through with each new opportunity.

In hindsight, it’s easy to see how I misinterpreted that Wayne Gretzky quote. Wayne didn’t line up a thousand crappy shots and take them all because he could. He had years of practice and instinct that allowed him to optimally line up his hockey stick, rack up the courage, and take the right shots.

When it comes to investments, Warren Buffett often speaks of a taking a “Ted Williams kind of discipline.”

Ted Williams was a baseball player on the Boston Red Sox who analyzed and carved the baseball strike zone into 77 individual cells. He then created probabilistic results of successful bats for each cell based on his history of hitting in each of these strike zones.

By using his rigid method and waiting for the perfect pitches in his optimal strike zones, Ted Williams maintained a .344 batting average and was responsible for more than a fifth of his team’s runs over two decades. For context, a season batting average higher than .300 is considered to be excellent and an average higher than .400 is a nearly unachievable goal. Ted Williams even managed to hit .406 in 1941 (source).

Now that I’m a bit more self-aware of my flaws, I take more time to focus and think before proceeding to jump headfirst into each new opportunity.

Venture capital has been the perfect industry to maintain this level of discipline. While each new founder I meet is unequivocally infectious, passionate, and convincing (as they rightfully should be), I only have a limited number of shots. Now, more than ever, I need to be defining my strike zone.

The trick in investing is just to sit there and watch pitch after pitch go by and wait for the one right in your sweet spot. And if people are yelling, ‘Swing, you bum!,’ ignore them. Defining what your game is — where you’re going to have an edge — is enormously important.

-Warren Buffett

Formalize Your Mentor Relationships

When I was much younger, I never quite understood the advice friends gave me around formally asking people whom they respected to become their mentors.

In my mind, life wasn’t supposed to feel so transactional. I built relationships with people over time and I never felt a need to directly ask someone to be my mentor.

Asking someone to be a mentor felt like the awkward dating phase in high school where you’ve both liked each other for a long time and you’re pressured into popping the “will you be my boyfriend / girlfriend” question.

Recently, I’ve gone back to square one to question my own beliefs and I’ve come to realize what a big loss it was to never formalize these mentor relationships.

Pop the Big Question

A few months ago, I met someone in my product community whom I immediately hit if off with online, so we decided to grab some coffee given he had recently moved with his family to San Francisco.

After chatting for an hour, I came to the realization that I had a great deal of respect for him in everything he had accomplished personally and professionally.

And so, for the first time ever, when the meeting ended, I verbally asked him to be my mentor. After a week of careful thought, he agreed to my request and we kicked things off.

Prepare for the Meeting

The first thing we did was establish a regular cadence of meetings. I initially felt bad about taking too much of his time, so I threw out the option of quarterly meetings. He immediately pushed back by suggesting monthly recurring meetings and we could scale back if necessary.

I came to the first mentor meeting prepared with an agenda in my notebook. There were a couple thematic areas of my life that I couldn’t prioritize and I wanted some advice on how to proceed.

We spent the hour talking through each of these “themes,” and he asked me to rate each on a scale of 1-10 (1 = not interested in pursuing this theme at all). Based on my responses, he was able to provide some objective 3rd party opinions on how to proceed.

After helping me prioritize my areas of focus, he put me on the spot and asked me to think about my one core life goal.

His objective there was to force me to distill various goals into one overarching goal that would act as an umbrella and north star.

(side note: funnily enough, this is a common exercise I do with seed stage founders that I work with. I’ll often keep digging with questions until we get to the one core KPI they want to focus on and we’ll figure out how to maximize that KPI)

We talked about a few other topics but I wanted to give you a sense of the value that I immediately derived from that first formal mentor meeting.

Document the Learnings

After that first meeting, I immediately created a Google Doc and wrote a recap of everything we had discussed, separating my notes into:

  • Raw Notes Transcript: Data dump of everything I could remember
  • Discussion Summary: Key bullet points summarizing the conversation
  • Action Items
  • Possible Topics for the Next Meeting

Writing this document is important because it reinforces the learnings in your mind and serves as a point of reference for future meetings to show that you’re actually making progress.

To recap, I no longer believe that it’s enough to have an unspoken mentor-mentee relationship where you both meet whenever convenient and chat about whatever comes to mind.

If you want to take your mentor relationship to the next level and show visible progress, formalize your mentor relationships by doing the following:

  1. Mutually agree to a formal mentor-mentee relationship (pop the question)
  2. Establish a regular cadence of meetings (try starting with a monthly cadence)
  3. Come prepared for every meeting with an agenda or topics you’d like to discuss
  4. Document learnings in writing after every mentor meeting
  5. Act on these learnings (show your mentor that you can walk the walk)

How the Economic Machine Works

After finishing my previous post referencing Ray Dalio’s Principles, I ended up digging around the web and came across this 30-minute gem where Ray Dalio uses extremely simple principles to explain how the economic machine works.

The video is nicely narrated & visualized – definitely worth the 30-minute watch.