Andy Trattner

January 18, 2024

Second in Command

The concept of career moats has been on my mind for nearly 4 years thanks to Tiger. I take keen interest in things that inspire the professional lives of people I find impressively accomplished yet unusually humble and thoughtful.

Interestingly, other people's religious texts don't always resonate with me directly, in the same way Seth doesn't resonate with many of my friends and readers. Nevertheless, by keeping in touch with Tiger, I'm reminded from time to time of Commoncog (I just paid $250 to subscribe while writing this blog post).

Perhaps the career moat framework hasn't resonated because I'm so bad at deliberate practice, or really any form of discipline. My use of the term "funemployed" to whimsically describe my current professional state of existence (since 2020, h/t Hattie) communicates this deliberately "suboptimal" approach. Or it could be that I simply enjoy discovering things on my own.

I received a little hug from Michael Sipser just before I received my MIT diploma in June 2018. Even more astonishing than him jumping down from the academic bleachers to greet me in line for the stage, was him in the math department's food tent, afterwards. I will always remember those couple brief moments speaking about my (lack of) plans post-graduation, and him telling me: "Andy, you remind me of a student I had who went to San Francisco and tried to become a comedian... He did not tell good jokes."

I was flabbergasted and shocked at the frank feedback. Time stopped as Sipser paused and stared at me. I did not know how to respond except to smile and laugh. He continued, "...But now, many years later, that guy eventually became the CTO of a company of some sort and seems to be doing well enough." Huh, thanks, I guess? But his remark turned out to be prescient.

As reported in my recent end of year reflection, collaborating with Austin on Shuffle has been great. I support Austin's CEO focus on growth and marketing by taking care of everything else as COO + CTO: product, engineering, customer support, event ops, legal, investor relations, recruiting, contractor management, etc. I often say "yes master" as a joke when Austin asks me to do things, or even when he's just making statements or observations. We get along well.

A few people have recently told me I'm in an envious position, that many people would probably love to live the flexible life I lead, and hold the exciting role I do. This is an entirely new experience for me professionally, and seems to be a reaction to our revenue chart (finally can pay the bills! maybe).

I counter that most would not be willing or able to go through a 3+ year stint of zero income, randomly living in a foreign country. I checked and have been burning around $50k/yr for the past few. On top of that, I threw away a million dollars at the outset to go on this journey. And in addition to the crazy financial risk, there's also significant responsibility: employees depending on a weekly paycheck to feed their families, terminal escalation point for customer interactions, etc. Last Sunday, I unexpectedly had to drop everything, change my social plans with just a couple hours notice, and do a 4-hour chunk of urgent work.

It's the life I chose because I'm not well-suited to being an employee—much to the concern of Michael Sipser, my grandfather, and at times, my sister. But I always thought my vocation would end up being that of a CEO, and probably a founder since I'm unlikely to be hired. All my previous ventures (going back to 2015) have had me in the driver's seat. Now, however, I'm wondering if I'm actually a better 2nd in command.

I'm not particularly skilled at generative or creative work. I'm not a hacker who ships cool side projects nights and weekends. I don't have a pointy edge to dive into a particular field and emerge with a business. Perhaps most importantly, it's simply hard to find tractable market opportunities. At best, my rate is to stumble upon a half-decent company idea every 4 years, but that's probably too generous. I was slapped in the face with the need for Senseg, and earlier for Lean On Me, but neither was well-positioned to actually make any money.

In the process of shutting down Senseg, I knew my main search mechanism for inspiration would be to talk with smart people doing interesting things. Now, I'm finally articulating that this is a particularly good strategy for me. It's so much easier to skip the whole 0 → 1 idea question, if I can.

That said, it's very hard for me to go below founder-level, as even being an early employee with tons of ownership doesn't necessarily feel like the point of maximal leverage. I am very cross-functional, combining experience with an analytical mind and the (occasionally manic) energy to simultaneously
  • define strategic business objectives,
  • form relationships, build trust, and empower people,
  • proactively initiate projects and important conversations,
  • think systematically on behalf of the customer,
  • dive into technical weeds, and
  • execute, while
  • driving towards a first-principles understanding, learning, and assessing progress realistically.

I'm not necessarily the best at any particular thing above, but I have a pretty good depth such that the overall combination of skillsets is probably rare and valuable.

Cedric talks about how the market indicates your worth in other employers trying to poach you. I've experienced this first-hand when jumping from Scale AI to Readme with a nice signing bonus and pay bump. I also have been recruited, less formally, to help with other folks' restaurants in Ecuador, and contractors have referred me to their friends as a good source of work and career progression.

When it comes to this new "2nd in command" role, I'm just getting started. Poaching offers have not really rolled in yet. But a fun upshot of identifying this niche, and continuing to operate at a cofounder level, is that in the future—if all goes well—I will get to poach myself.

About Andy Trattner