1. Venturing Out

Why I left my job to start a company

Intro

The objective of this post is to articulate the decision-making process around my recent life change: leaving my job to start a company, and also this blog in the process.

This is, in part, a reference for my future self, who may find himself without stability and/or with stress, and needing the assurance that decisions were made deliberately and logically, with as much information as was present at the time.

I’m also sharing this on the interwebs, not in an attempt to defend my decision to others, but in hopes that something I say is relatable, informative, or at the very least entertaining for someone who cares to give it a read. None of those things can be promised, though.

I’ll structure my thoughts around decision-making using three sub-decisions (why leave, why entrepreneurship, and why blog), that together explain the simultaneous pivot, and I will try to cover each in a bit more detail.

A few caveats before beginning…

I recognize that venturing out on one’s own is a privilege not everyone has, so I would be remiss if I did not state how lucky I am to be in a position that allows me to do so. I have been afforded freedoms and privileges, both overt and covert, earned and unearned, that enabled me to choose my own path and make my own decisions with a degree of security. Many have acted more boldly than I have, from less favorable circumstances, and those people have my utmost admiration.

Also, people leave companies all the time, so I hope this does not sound too much like an “I’m taking my talents to South Beach” announcement. I have been a little off the grid recently, enjoying new-found freedoms post job and post vaccination, and thought this would be a symbolic start to the new adventure.

Let’s dive in…

Why leave

I will preface this section by saying that my decision to leave had very little to do with the company, position, or leaders I had. Quite the opposite, actually - they are what kept me around for so long (over 5 years in fact), and I owe many of the skills and much of the confidence that enabled this pivot, to the people and experiences during that time.

Explore vs Exploit

And one more preface. For those who don’t know, I was a senior data scientist in my previous position. So, naturally, that in part directs my decision making processes. Because to study optimization problems and learning algorithms without attempting to apply those concepts to other areas of your life just seems like a missed opportunity. Like being a fruit farmer but never trying to make a berry crisp.

Explore vs Exploit is often referenced in reinforcement learning algorithms, and more specifically in the multi-armed bandit problem. This problem is best represented by a gambler at a row of slot machines, each with different probabilistic payouts, with the goal being to choose the amount and order in which to play the different machines to generate the maximum return. Generally, the gambler’s strategy should be to experiment (explore) more at the beginning, in an attempt to gain information, so they can choose (exploit) the most optimal decision later in the process.

Translating that to my life, as a logical gambler, I am still in the process of gathering information. My previous company was the only slot machine I had really played on, and I know there are other options to explore. It may be the optimal machine, but until I have more information, I cannot be sure. Therefore, I would like to accelerate the rate at which I am learning, and that means playing a new game.

S Curves

As is typical in the field of data science, I like trying to represent the dynamics of situations using curves (equations). This serves to understand what variables are important or to predict what may happen in the future. One sneaky relevant curve is the S curve (sigmoid function), which is often used to model conditional probability and has applications in neural networks, but shows up in a lot of other places. It’s mostly saying that, between two different groups, there is continuity that can be described in some generalizable way. Like when you flip a light switch, although it appears to be an instantaneous step change in behavior, it is actually more gradual if you really really zoom in. Learning curves are a much better example of this. You don’t instantly go from not knowing something to knowing it, but oftentimes the learning starts out slow, experiences a period of high acceleration, and then decelerates and plateaus.

In reference back to the multi-armed bandit problem, paying attention to where you are on the learning curve helps you determine when you have enough information from a given machine to move on.

Luckily, I was on a number of teams within the company (different sub games of the larger machine) that reset my position on the learning curve a bit, but overall I felt like my learning had hit an inflection point and was starting to decelerate, and thus I decided I should seek a new challenge. Growth comes from having the curiosity to explore different learning curves, the discipline to overcome the barriers to entry (initial flat part), and awareness to understand when you are plateauing.

Potluck Problem

Working at a big company is kind of like going to a big potluck. You’re at the grocery store trying to decide what to bring and needlessly stressed about striking the right balance between not disappointing others and not wasting effort. But as an above average performer, you decide to play it safe and double the recipe, only to show up with the third dip and all of the dippers gone. So you’re stuck eating leftover spinach artichoke dip for lunch all week. This happens when you aren’t very close to your customers, you don’t have a good measure of success, and responsibilities are loosely defined.

It is the lack of a 1-to-1 relationship between effort and value that makes large potlucks and large corporations generally inefficient.

Smaller potlucks that take the form of a tasteful summer BBQ (like 8-12 people), are great, though. They allow people to specialize while still getting a diverse range of dishes, and impressive chefs get the credit they deserve.

A questionable segue at best, but alas.

Why entrepreneurship

Starting a company felt like the only logical path after leaving my job. And, in part, I did leave my job to start a company, so this deep-seated decision requires a bit of unpacking to understand why I am the way that I am.

Life Objective

To be fulfilled and acquire the knowledge necessary to provide the maximum amount of value to others.

That is the mission statement I came up with during a workshop at my previous company. While short, unspecific, and multiple years ago, I have held onto it and still use it as a reference at times. The first part, “to be fulfilled” represents the ongoing attempt to be internally happy with the life I create - by surrounding myself with friends, family, and the things I love. The second part addresses the external impact I would like to have on the world. For that, I believe, entrepreneurship is the best method of finding success. As mentioned above, I am still early in the process of acquiring knowledge, and I believe starting a company is a great mechanism to learn quickly. Also, by rough definition, starting a company means providing enough value to a group of people so that they will compensate you monetarily with an amount, greater or equal to the cost of providing that value. Thus, I feel like my entrepreneurial success will be directionally related to my life objective success, and aligned incentives are always a good thing in my perspective.

Expected Value

The expected value of your impact on the world is like a vector. It is defined by two things: direction and magnitude. That’s it.

This is a quote by Sam Altman, a person whom I respect very much, and someone who has made a large impact on the world in a relatively short amount of time. Having the freedom to venture out on your own means getting to choose the direction of your vector, and finding something that you are passionate about increases the magnitude of it. He also talks about expected value as it relates to the financial return of starting a company, and how the upside (high) multiplied by the probability of success (low) generally exceeds the financial benefits of a normal job. We could argue about how to value the excess stress involved here, but overall I trust his assumptions and thus his assertion: that one should highly consider taking the risk to start a company.

Regret Minimization

I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the Internet that I thought was going to be a really big deal. I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not ever having tried.

This is a quote by Jeff Bezos on his regret minimization framework for decision making. I appreciate this because it is both simple and a framework. It involves asking the question - in X years will you regret not doing this thing? If the question is yes, then you do the thing, if it is no, you don’t. Future regret is hard to quantify, so it can feel more like an innate desire than anything, which in some ways feels like a dilution of the other points I’ve articulated. In reality, though, I think it is like the activation function of all the other convolutional layers. When I am 40, I will regret not having ventured out to start a company, for a number of reasons, so therefore: yes.

Why blog

I am hoping that writing out and sharing my thoughts can provide value to myself (internally), to my future ventures (synergistically), and to anyone who cares to read (externally). The plan is to write posts weekly, biweekly, or monthly to provide updates on my ventures. Here are some more detailed reasons that can be grouped into those high level reasons above:

• Practice Writing (internal) - I’m currently not great at articulating my thoughts. I would like to be better at it. This blog should provide practice structuring ideas that are in my head and finding the words to put them down in writing.

• Be Vulnerable (internal) - I have generally been a bit more on the reserved side of things, so putting myself out there and into the public domain is uncomfortable but probably good preparation for whatever I’ll need to do in the future.

• Create Something (internal) - I feel like everyone has some sort of creative inertia inside them, and I would like to exercise mine more. There is a lot of satisfaction that comes from creating something unique, valuable, and lasting. I hope to create companies that fit this description, so this is me creatively diversifying.

• Stay Accountable (synergistic) - I’m a competitive person, and I believe social accountability is one way to create a competitive environment. Also one of my biggest fears is letting people down, so I’m going to try not to do that. Therefore you in some unknowing way will be helpful here.

• Talk to Customers (synergistic) - I realize that creating things in a vacuum isn’t helpful. At my previous company, I had a number of people willing to test my ideas. Those people are harder to access now. I realize that talking to customers is the only way to build something people want, so developing a mechanism to reach people seems to make sense. That said, I may use you for problem identification or product validation at some point, if you don’t mind.

• Inspire (external) - I feel like most inspirational people don’t set out to be inspirational. And creating a blog can at times feel cringeworthy. So why do I feel like I deserve to have an audience? I don’t really now, but maybe someday, and at the end of that day, I would like to be prepared. Aligned with my life objective is inspiring others to be entrepreneurial, so this blog could help with that.

• Entertain (external) - I’m sure there will be lots of ups and downs and I hope to be as transparent as possible with my successes and failures. The stories may or may not be humorous, but ideally they’ll make you feel something.

This ended up being a bit longer than expected. Maybe it resonated with you, maybe it didn’t. Regardless, I hope to improve things with practice and hope that you’ll be here to partake in the journey.

In the next post, I will dive into the approach of how I plan to build. Share, subscribe, or provide feedback if you’d like. In any case, thanks for making it this far!

Will