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15 Tables to Mastery

Within a reasonable period of time, and without extravagant resources, how can one reach a level of expertise in business high enough to consistently produce growth in any business? An experiment begins.


In the summer of 2019 I took a startup I was advising down to Melbourne Australia for a series of short pitches at a startup accelerator. The job was to make 15 minute pitches to 10 tables of professionals on day 1 and another 10 tables on day 2. Because I was an advisor myself and not pitching, my job was pretty easy. All I had to do was observe how my team was pitching, the response to the pitch, and the questions that were asked. After each pitch, during a five minute break, I would tell the team what I noticed and suggest some things to improve on. They did a great job implementing those changes and improved with every pitch.

What happened at a macro level, I think, was pretty interesting. By the end of day 1 (10 tables), I had pretty much learned the spectrum of reactions to the pitch and the list of questions that would come up. My team and I huddled that evening and the next morning and discussed a series of overall improvements we'd make in response to those findings. On Day 2, for the first five tables, we continued to make micro-adjustments, and then for the last five, the pitch was on autopilot. By then, they had it wired.

My main takeaways from that experience were:

  1. I felt the distinct feelings of knowing when we were close, and then knowing when we had it. At those points, it wasn't a guessing game around what was working and what wasn't. We had learned enough about the process to produce consistently positive results.
  2. It required not one, but several tables worth of professional perspective, in order to have a complete enough landscape of the possible reactions and questions.

Earlier today, I thought about how business is the art of producing value: people want or need what you make, and they choose to buy it from you. It is probably governed by the same laws as everything else in humanity, and therefore, patterns would emerge. (Pareto's law, Parkinson's law, etc.) On that premise, I wondered if I could retool my learnings from the pitch event to better learn these principles of business. What could I do 10 or 15 times over to get the understanding of how to consistently, reliably, systematically produce growth for any business?

The most obvious answer was to go start and run 10 or 15 different businesses. I'm sure it would work, but I don't have enough time in my whole life to do that correctly, let alone this year, so I need something a little more efficient.

I came up with some alternate ideas:

  • Take 10-15 semesters of collegiate business courses
  • Listen to 10-15 full series of business podcasts
  • Read 10-15 carefully chosen business authors' répertoire (i.e. books)

Personally, the last option appeals to me the most because I feel that (most) books tend to have the best concentration of good ideas, and you can use online reviews, endorsements, and summaries to point you to the best ones. I've also found books to generally be the best tool to advance any aspect of my career so far.

So as I welcome in 2021, I'm planning now to set aside time every day to read: enough time to read through one author's worth of books every month. If I follow through, I figure that by summer I should know pretty well if this idea is going to work, and ultimately lead me to the full set of skills I seek.

It all sounds great at first, but I also need to address a few other problems I've run into in the past:

  1. As someone currently running a couple of businesses, how can I be sure I'll find enough free time every day to read enough?
  2. How will I choose which authors to read?
  3. How can I not only retain what I'm reading but also put it into active practice?

The good news is that I've been doing a fair amount of poking on effective reading and time management in the past few years, and I think I have some pretty good ideas. As I figure it out, I'll share more about what's working and what's not.

Prior Art#

While in pursuit of a similar goal, Tim Ferriss almost went to Stanford Graduate School for Business before instead using the tuition money to make 15 different angel investments over the course of two years. After the 15 investments, he notes that he didn't lose money, but also that it would take him a few years longer to really understand how his experiment went. (In the end, he won handily.) On that note, it seems like if I can set my foundation of understanding of business this year, and see the results actualized over the course of a few years, that would be a major win.