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.


Consumer to Creator

SumoCon 2016 with Noah Kagan (SumoMe), Nathan Barry (ConvertKit), Ankur Nagpal (Teachable), Justin Jackson (MegaMaker)

In September 2016, I attended SumoCon, the first conference that SumoMe ever hosted in Austin, Texas. The photo above with Noah Kagan (SumoMe), Nathan Barry (ConvertKit), Ankur Nagpal (Teachable), and Justin Jackson (MegaMaker), represents one of the happiest and most symbolic moments of my life.

This was my first time meeting all of these guys in person, but I had already been using their products for several years. Without their products and companies, I most likely never would have become a “creator”.

Justin Jackson was one of the first “digital entrepreneurs” who I started following online. He had successfully launched a number of digital products including his popular ‘Marketing for Developers’ book and a lot of his writing taught and inspired me to think about how to create and sell digital products.

When I started Product Manager HQ, I used Noah Kagan’s SumoMe product to significantly improve subscriber opt-in conversions on my website. These subscribers became the foundation of my weekly newsletter list (a list that I’ve been sending weekly newsletters to for the past 3 years).

All of these subscribers are managed through my e-mail provider, ConvertKit, a company founded by Nathan Barry. ConvertKit helps me manage my website’s drip sequences, subscriber lists, automations, and newsletter broadcasts to make sure that I’m always engaging with my loyal readers.

Lastly, my entire online course, One Week PM, is hosted and managed by Teachable, founded by Ankur Nagpal. Teachable allows my entire course to be self-serve, where students can enroll and login to view lectures anytime they want.

Without these guys, Product Manager HQ most likely would not have existed or reached the scale that it is today. Their products enabled me to become a “creator” and for that, I am eternally grateful.

We’re trained from a young age to consume. Part of this is a result of our legacy educational system borne from the Industrial Revolution:

Mass education was the ingenious machine constructed by industrialism to produce the kind of adults it needed. The problem was inordinately complex. How to pre-adapt children for a new world – a world of repetitive indoor toil, smoke, noise, machines, crowded living conditions, collective discipline, a world in which time was to be regulated not by the cycle of sun and moon, but by the factory whistle and the clock.

The solution was an educational system that, in its very structure, simulated this new world. This system did not emerge instantly. Even today it retains throw-back elements from pre-industrial society. Yet the whole idea of assembling masses of students (raw material) to be processed by teachers (workers) in a centrally located school (factory) was a stroke of industrial genius. The whole administrative hierarchy of education, as it grew up, followed the model of industrial bureaucracy. The very organization of knowledge into permanent disciplines was grounded on industrial assumptions. Children marched from place to place and sat in assigned stations. Bells rang to announce changes of time.

The inner life of the school thus became an anticipatory mirror, a perfect introduction to industrial society. The most criticized features of education today – the regimentation, lack of individualization, the rigid systems of seating, grouping, grading and marking, the authoritarian role of the teacher – are precisely those that made mass public education so effective an instrument of adaptation for its place and time.

Source: ‘Future Shock’ by Alvin Toffler

Despite this fact, we should all aspire to break this consumption mindset.

99% of the world will be perfectly satisfied spending the rest of their life consuming, but only the bold will dare make that leap towards becoming a creator.

Any chance I get, I’ll always stand with a hand outstretched at that border, ready to catch the hand of any individual who’s willing to make the jump.

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