10 November 2013
Wasting Time as a Career Manager


(cross-post from Medium)

I’m fascinated by history, especially American history. Recently, I finished a book called Six Frigates: The Epic History of the Founding of the U.S. Navy, about how a young United States established its maritime presence to protect its trade interests.

Back then, a naval officer could expect to climb the ranks after leading a mission to burn a captured ship, as Stephen Decatur did, for example, in Tripoli Harbor in 1804. Or he could ascend the ranks by taking command of and successfully sailing a commandeered enemy vessel to a friendly port.

And all officers sought captaincy of a vessel. A captain, at least in the early days, was a man in control of the destiny of his crew and his ship. He made decisions about where to sail, whether or not to run from or engage an enemy, where to set to port and what the crew should eat. All captains were capable seamen, understanding the mechanics of their ships, navigation, rules of engagement, strategic objectives of their governments, and how to manage a crew. Captains often led boarding parties when attempting to seize an enemy vessel with sword and pistol in hand. Respect of the crew was earned. The Captain, after all, was a sailor, just like them.

I recently entered the job market after leaving my position as CTO of popexpert. Before that gig, I spent five years climbing the corporate ladder at a company in San Diego, where I left with title of Senior Director of Software Development.

At one point I managed around 70 software developers and was responsible for the technology behind 12 products. I got very good at managing relationships, doing performance reviews, hiring, firing, and structuring teams. But I did not write code. I did not lead any boarding parties. By design, my job was to lead my crew from land, letting them sail without me. This, being in-line with the philosophy of accomplishing through others. Give them direction and trust the crew to execute. And career-ascension was dependent on my ability to do this well.

I had become a career manager. I had become better at managing politics and organizational structures than technology.

When a Google recruiter contacted me by phone, she asked me a total of zero questions about my time as Senior Director of Software Development. She was interested in my ability to sail a ship. She focused entirely on my time as CTO of popexpert.

I had the same experience with other companies, AirBnB, AngelList and GoldBely, among them. They were interested in my technical aptitude. How well could I code? How would I solve architectural problems? Could I do FizzBuzz?

I realized, through this experience, that technology companies (the good ones anyway) value technology leaders who are still good technologists. If you dis-engage with technology, like I nearly did, you are killing your career.

1 October 2013
Bright, Green, Slim-fit Pants - A Strawman

(cross-post from Medium)

I have a great idea. I’m going to make bright, green, slim-fit pants and sell them. I’ve done market research, too, and have figured out that if I can get the people who shop at The Gap and Banana Republic to buy my pants, I’ll create a bright, green pants cultural revolution and huge business.

So how do I get the people who shop at The Gap and Banana Republic to buy my bright, green, slim-fit pants?

Option 1: Start marketing directly to them. My aim with this approach is first to make them interested in bright, green, slim-fit pants and second, to buy a pair once interest (demand) is established.

Option 2: Find an adjacent market where I don’t have to engender interest, and market to them instead. My goal here would be to work out the kinks in my product, generate early sales, and get feedback from real people.

After deliberation I go with option 2. While early on this option exposes me to a much smaller market, it allows me to get things right before I go for the “big kahuna”. And who knows, option 2 might even be a gateway to the Banana Republic and Gap market I covet.

So I do some research, and I find a market comprising people who wear bright, purple, slim-fit pants. I also find an adjacent market of people who wear bright, green, slim-fit shorts. And I identify a third group of people who don’t particularly care what they wear on their lower body, but they consistently wear shirts with epaulettes.

I go all in targeting these people with my new marketing campaign and find that, indeed, demand exists and some of them buy my bright, green, slim-fit pants. Trying to understand this group of early adopters more I do some analysis. One consistent trend emerges: my early adopters are “fashion forward”.

After a few months, I start seeing sales happen from a few less fashion-forward people. Has a new market found my bright, green, slim-fit pants? It would seem my early, fashion-forward buyers started talking with their less-fashion-forward friends about their awesome pants. This, plus observation of my bright, green, slim-fit pants being worn at trendy parties, has generated demand from a new group of people.

Further analysis shows the not-so-early-early-adopters represent a bigger market opportunity. So I focus my marketing efforts on them and go all in on this newer, larger market.

After success with this new tactic, I start getting a trickle of sales from a third group of people. It would seem that the not-so-early-early-adopters have mainstream friends who shop at The Gap and Banana Republic. And these mainstream friends have taken notice of the not-so-early-early-adopters wearing bright, green, slim-fit pants in public.

Boom! This is the market I had originally envisioned selling my product to. This is how I create a bright, green, slim-fit pants cultural revolution.

1 April 2013
Talk to me on popexpert


It’s been about 5 months since I left my corporate job to co-found popexpert. And man, we’ve been humming along.  popexpert connects people who are hungry to learn something new with people who have something to teach.  It’s all done over live video (thanks to WebRTC).  If you’re interested in chatting with me about what its like to leave a (relatively) secure job, move to San Francisco, and have a new baby boy three weeks later, or if you’re just curious, book some time with me:


You’ll have the honor of being one of our first users. I’m looking forward to talking with you.


21 March 2013
Campfire Sounds

One of my favorite features of Campfire is the the sounds you can play to get people’s attention.  But apparently not everyone would agree with me:

Screen Shot 2013-03-21 at 9.21.51 AM

And if you’d like to play sounds of your own,  check this out, https://gist.github.com/davist11/1204569.

21 February 2013
Ideas vs. Execution

steve-jobs-lost-interviewI re-watched “Steve Jobs, the Lost Interview” a few nights ago on Netflix while I was cutting a little code. About half way through my interest piqued when Steve was asked about product development at Apple. His answer summarizes a position I’ve long held but until now have not been able to fully articulate. And I was fortunate enough to find a Fortune article about his answer to this particular question.

The beginning of Steve’s answer goes like this:

"You know, one of the things that really hurt Apple was after I left John Sculley got a very serious disease. It’s the disease of thinking that a really great idea is 90% of the work. And if you just tell all these other people "here’s this great idea," then of course they can go off and make it happen.

And the problem with that is that there’s just a tremendous amount of craftsmanship in between a great idea and a great product. And as you evolve that great idea, it changes and grows. It never comes out like it starts because you learn a lot more as you get into the subtleties of it. And you also find there are tremendous tradeoffs that you have to make. There are just certain things you can’t make electrons do. There are certain things you can’t make plastic do. Or glass do. Or factories do. Or robots do.”

You can read his full answer at http://tech.fortune.cnn.com/2011/11/11/steve-jobs-the-parable-of-the-stones/.

I’ve worked at companies that suffer from this “disease” before but could never put a finger on what it was that bothered me about them.  Now it’s clear to me.  In general terms, mediocrity occurs when companies lose focus on craftsmanship.  I’ve talked with many high-level executives in the past who think they can pick up an engineer on the street to implement an idea.  All it takes is a few code monkeys, right?  This kind of mindset is indicative of the “disease”, as Steve describes it.

Get your shots so you don’t contract the disease.

19 July 2011

The philosopher in me found this interesting.  Alan Watts, a famous British philosopher, talks about nothingness:

16 July 2011
Netflix Envelopes

I have come to loathe these removable seal covers that come with Netflix envelopes.  I have them lying all over the place in my house.  Garbage cans are always inconveniently distant when I take these things off in order to ship my DVD back to Netflix after watching it.

Yes, I’m lazy.

19 June 2011
A Little Side Project


I’ve been reading a book called “Managing Humans" by Michael Lopp.  Michael is a Software Development Manager, and his book is more anecdotal than anything describing his experiences managing people and the conclusions he’s come to as a result.  They teach you in "Management Class", as you climb the corporate hierarchy, that Software Development Managers should put away their IDEs and stop coding.  As the thinking goes, the temptation is just to great to dive in and write code to fix a problem when, instead, that problem should be delegated to those being managed.

I’m at a point where I manage Development Managers.  And I’ve made “stop coding” a goal for many of them.  They struggle with this.  And frankly I miss programming too.  I miss creating tangible output each day.

So back to Managing Humans.  Michael points out that he was wrong to tell his managers to put down the code.  Instead, he says it’s important to keep programming.  It’s important to stay up to date on new technology.  It’s important to understand the source control system, the IDE, the build process that the team is subjected too.

And frankly, I like the idea of being more like Alexander the Great.  He was in charge of half the known world in his time and yet he went charging into battle, with his troops, sword in hand.

Or how about this analogy.  In Cricket, the Team Captain (akin to a Manager in Baseball), plays with the team.  He bats.  He fields.  And sometimes he bowls (pitches).  But he also manages his team orchestrating them around the field strategically, or instructing them to swing away or bat more defensively.

I decided earlier this year that I would dust off my home computer system and get code fit once again.  While the opportunity isn’t there at work, I thought I’d create my own opportunity and launch Kompilr.  Kompilr is a small website, running in Ruby on Rails, that allows people to visualize their careers.  My Kompilr is http://www.kompilr.com/jeremythomas, for example.  Through this experience I’ve shot right back into relevancy.  I know how to do an automated deployment with Capistrano.  I understand why GitHub is so awesome.  I know how to write client-side libraries to integrate with Oauth providers.

So to all you Software Development Managers out there, code on.  Don’t listen to anyone who tells you to stop.  Software is your passion, it’s what you’re good at.  0.003% of the world’s population can write code.  Use your skill to create new things and inspire your teams.

11 May 2011
We Are Software engineers

Here’s a video I put together for my teams at Active.com:

31 January 2011
Your Guys’s

Inspired by an article in the December issue of The Economist about business cliche words, I thought I’d add my own phrase to the list.  And that phrase is “from a ______ perspective”.  It is ludicrous how often I hear that phrase in my professional life .  A marketer, for example, might be giving a talk and say:

"From a consumer acquisition perspective we’re at our goal.  We need to strive harder to hit our goal from an ad impression perspective.  But we’re on the mark from an overall perspective".

There are several other words that can substitute “perspective”, namely “standpoint” and “regarding” (if placed before instead of after the point being made).  But more importantly, we need to be more creative about how we deliver our thoughts.  We might rewrite the talk above to read:

"From a consumer acquisition standpoint we’re at our goal.  We need to strive harder to hit our ad impression goal.  But overall, we’re on the mark."

This is a bit more succinct.

The other phrase I’ve noticed people saying recently is “your guys’s”, as in “What is your guys’s release date?”.  A piece of the linguist in me dies every time I hear this phrase. It would be better to say “What is your release date?”, where “your” implies “all of you”.

What are other work phrases that you hear?