Prioritization or the art of not caring

The art of not caring is really about prioritizing what’s important in your life and what isn’t.

While this might sound harsh, the simple truth is that we all have a finite amount of emotion and focus. While the total amount may fluctuate over time, it’s still static at any given moment. If we’re able to describe why something or someone is important to us then we’re able to prioritize it. But if we’re unable to identify that definition then it’s time to stop caring ™ and move on.

Sure, it makes sense to care little bit about the things that require only a little attention and care–you can certainly have a gradient of value vs. care–but forcing yourself to take stock of what matters in your personal and work lives will allow the things that really are important to flourish. In our lives at home this is closely tied to our personal values, and at work, these factors are closely tied to what will move the business forward.

The art of not caring also shouldn’t be moralized. It’s not about laziness. It’s not about doing something because we should. It’s not about bucking perfectionism. It’s about allowing the best parts–the areas where we truly feel we’re meeting the values we’ve set out for ourselves–to come to the forefront so that we focus on and prioritize them. And if you don’t truly care about someone or something, then you have no business bothering them or it.

Too often we feel compelled to “finish” something, or see something (or someone) out because we’ve already sunk so much time, or feel compelled to drag ourselves along due to some other cognitive bias that keeps us stuck in the past and unhappy. But the truth is that the sooner you quit something, and the sooner you stop caring, the sooner you’ll be able to prioritize what gives you deep happiness and success over all else.

The rest falls away and the foundations for a good life can flourish instead.

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Software startups take over your life

Software startups take over your life. This isn’t a bad thing. Rapidly growing a company including simultaneously building an incredibly skilled team, fundraising, and writing code requires laser focus and surgical allocation of time. 

It’s not a journey most are able to take. But if you do, meditating on your personal life is just as important as how you think about your company, team and product. 

Brad Feld is a legendary startup investor who is not only incredibly skilled from a technical and business perspective, he’s widely known as one of the best writers about life in general on his blog Feld Thoughts. His thinking about philosophy as it relates to work in startups is incredibly compelling, as is his unafraid approach to openly discussing mental health, personal life, etc. 

Learning from the best, I hope to do even a small fraction of the same. 

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I’m not above bad code

red and white wooden door

In startups there is this over-engineering ethos that exists sometimes among pie-in-the-sky-brained developers that your stack has to be perfect and pure from day 0 as a startup.

This couldn’t be further from the truth, and a majority of the most successful software companies of all time all started out with crap code.

The winning focus–the way to actually execute–is to build something people want, and to build it fast. Polishing your stack and coding styling early on only distracts your team from focusing on the only thing that matters in those early days: shipping features that move the business forward to increase revenue and keeping engineering velocity up.

All hail shitty code.

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red and white wooden door

I’m a fucking software engineer

There have been times in my life when I’ve been pulled away from the core work that fulfills me most in life: building software companies that grow extremely fast. This is a dangerous lull and valley for an engineer to be in. We’re naturally antsy, aloof, and easily bored. And whenever the topic of burnout comes up I always share that working too little–facing too little of a challenge and staying stuck in complacency–can lead to even more severe burnout than being overworked. At least in the case of office jobs.

Pulling yourself out of this type of mud is hard work, even for highly motivated people or engineers (engineers are sort of people, but sometimes we’re quite rude and could definitely be a little nicer). This is especially true if you’re doing “ok enough” financially or in your career trajectory.

We all go through seasons and changes in our lives that can take us by surprise and if we do not have extremely firm, confident footing in both our relationships and our work before we head into an unexpected storm, we’re bound to find ourselves stuck in the muck even as previously incredibly accomplished people.

My therapist and coach has told me that anger can be motivating. I don’t get angry, but I do try to summon it sometimes to motivate myself in interesting ways.

So when I’ve found myself stuck in the depths of Mordor, I rip myself out and say to myself, “I’m a fucking software engineer, and I can literally make life-changing technology out of ‘nothing.’ And that’s fucking magic.”

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Don’t talk about the work: do the work

In startups and tech, the most successful people in the industry have an incredible bias towards action and execution. Execution ability is the only way to delineate those who will succeed and those who will crash and burn before they ever get out the door.

I’m often amused by friends and acquaintances who come to me with startup “ideas” and ask me not to “steal” them. I chuckle in my mind, and keep myself together because I very much like and want to keep my friends, but there’s no easy way to tell someone who’s never written a line of code in their life that there is essentially a very narrow, almost impossible path to executing on even the most profitable of B2B startup ideas.

A successful path to execution relies on a mixture of enormous luck in your existing network (university, engineers you work with and who trust you), connections to not only many different potential angels and venture capitalists through the lifecycle of your startup—but really good ones you can trust to not rip your company from underneath your feet unexpectedly and who can add real value—and excellent skills in recruiting, retaining, and nurturing incredible teams.

People are extremely difficult to understand on average. This is why there are so many terrible managers in the world, and why the pantheon of hilarious office comedies exists. Startup management strategy also varies wildly as you scale. The team you hire from day 0-100 will look and act nothing like the team on day 500 or even on day 200.

Execution is many things, all at once. Can you not only create a product road map but actually build each feature efficiently and quickly? Are you meeting the needs of real customers in what you build or the whims of your engineering team? Can you ship code efficiently and quickly? Can you rely on and motivate every member of your team–including yourself–to take deep ownership of the every part of the business? Can you move fast, iterate, learn and adapt better than any over your competitors?

So, all you need is a bias for action. And an ability execute while delicately managing 50 different spinning plates between teams simultaneously building and selling an incredible product that customers actual want (and that beats out your competitors, too).

Sounds easy, doesn’t it?

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On blogging and writing late night: Hello Again

I’m building a new startup in the SaaS space. I don’t work in public, but I will tell you that the company is called Codespeed and we’re working on something really big in the developer tools space.

Our addressable market is massive. It’s essentially any company that leverages code or software. Which, conveniently, has been eating the world exponentially for years as Marc Andreessen so famously said in the most legendary and historic tech essay of the 2010s (originally appearing in WSJ). In non-tech-history-jargon, what he means is that there are exponentially fewer and fewer businesses that do not leverage software in some way to get their products or services out the door, and in fact, I can’t think of any at all. Even the local hardware store uses some of the same point of sale software as Soho’s hottest boutiques. Incredibly high quality software is now finally universal and accessible. How cool is that?

Anyway, the point of this post is actually to demarcate my return to blogging. I’ve tried to start back up over and over again in recent years, but don’t get it twisted: I built my first custom blog in 2004! I was amused for years back then at how random posts of mine would hit the top of the search engine results pages on Google for random song titles, and other bits of pop culture, driving enormous amounts of traffic to me, ultimately helping me sell my first startup at age 14. (Really.) But now that domain is dead and gone, and the SEO lost to the ether!

So, as with many things, we begin anew. I’m going to continue to write most of these posts late night, when I need to throw some of the ideas knocking around in my head onto the screen so I can actually go to sleep! I have an enormous amount of intellectual energy piled up at the end of the day, and this, much like working out for me, does a good job at tiring me out.

I’ll be blogging here mostly about my work, but it will be mixed with a healthy number of amusing tangents and bits of color and context from my life as a professional software engineer since the age of 15. (Really.)

Oh, and I probably won’t edit this much as I get started and into a nice cadence.


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