How I like to work

I just stumbed on an old email I wrote a while ago to a prospective employer. I’m posting it because I’m curious how much it matches other people’s preferences.

> We didn’t get a chance to talk much about culture, but there’s just a few questions that I’d love to hear more from you on:

> -What kind of environment do you want to work in? What kind of environment do you work best in?

I’m happiest when I understand the big picture and can participate in the conversation about what to build. I know some programmers hate vague requests, but I thrive on talking with clients, especially when they don’t know a damn thing about how computers work.

I start with some rough sketches and then iteratively, we design the product together.

> -How do you like to be managed? How do you manage others?

The best managers I’ve had made it seem effortless. I knew my work mattered, I got a chance to learn things and work on cool projects, and when we had meetings they felt more like kids designing secret hideouts rather than a trip to the principal’s office.

How did they do that? I don’t really know, but I think it was a function of what we were working on, who we worked with, and how we did it.

When I lead teams, before each day starts, I spend a good amount of time by myself, planning what I want each person to do.

Then I’ll tell each person what I expect them to get done. That’s a starting point though — I’m happy to have a conversation and then reassign and reorganize tasks.

After that, I try to handle as much of the tedious stuff as possible, so that my team can think deeply about big problems. That means I’m happy to handle the tasks for stuff like changing labels on buttons,or debugging some non-core system, or replying to clueless customers.

I don’t think of management as a reward for paying dues. I think of running a team of developers as sort of like programming, but at a much higher, more abstract level.

The other thing I aim to do is make myself redundant. There’s nothing worse than feeling like you can never take a vacation because everything will fall apart. I encourage everyone else to share knowledge and cross-train each other, even if it means it costs us throughput in the short run.

> -Can you tell me a bit more about remote working in your experience? What’s worked well / not well?

Emailed screenshots can save a lot of time when there’s some layout bug that needs to be fixed. And I like IM for discrete questions, like “what is the URL to the testing box”.

But really, I’m a big fan of talking on the phone. I find that a 15-minute phone conversation where both people are totally focused on that conversation is often way more efficient than two people just barely paying attention.

Generally, I think regularly talking through stuff is key to keeping everyone invested and focused on the real goal.

That’s it!

Looking for a few CLE pythoners for a quick project

I can build it myself, but it’s going to take a lot longer. I’m looking for a few people to help me build a geographical search app.

If you’re smart, live near me, and have at least eight hours a week to work, let me know.

This will be for some combination of money up front and equity.

I expect to launch in anywhere from six weeks to three months after the start.

I have no patience for ideologues, jackanapes, or freeloaders.

Moving on

Last week marked the end of my employment with OnShift Inc. What started off as possibly the worst idea for a business conceivable (I’ll justify this claim later) is now an enterprise.

It has been a really good experience. I got to build something all myself. I had some really patient customers that politely filed bug report after bug report, and met with me over and over again to discuss their frustrations.

And then the business crossed one of those inflection points.

We started getting sales. Customers became happy to be references. More than once, people offered to pay for the product out of their own salary after they sat through a demo.

Some fantastic developers and designers joined the team.

In March I sat in the back of the room during a training. At the end, the trainer pointed me out. Usually I take that moment to do my little talk about how this is a new product, and these users are going to run into bugs or things that just seem goofy. I tell them I really want to hear about them, so that I can fix them as soon as possible.

But before I started my speech, everyone started clapping.

So that’s why I have to / get to / want to / need to leave. For about four years now, I’ve been banging rocks together trying to start a fire. And now I got one. So now I’m going to take a break, and perhaps more importantly to OnShift, get out of the way.

I’ll be happy if the business makes it big. I’ve been fully vested in my shares for a while now and I keep those after I leave. But this was never about getting rich. This was about proving something. I aimed to prove that I could design a product and then start a business around it.

I’ve been focused on getting that fire lit for the last four years. Now it is lit.

As for that worst possible biz plan, I’m not going to spell it out. Instead I’ll cram all the bullet points from my partner’s slides into one run-on word salad:

Orthodox Judaism SMS location-based time of Sunset on Friday mobile microblogging opt-in advertising

A few iPhone or android app ideas

Just like my post with some web app ideas, feel free to steal any of these.

A fake lottery game

This has already been done several times. You would start with some money (fake money) then buy some tickets and scratch them off. Some would win (more money) and most would lose. Maybe I would hide silly messages in the tickets. The gimmick would be the activity of scratching off the tickets, or maybe spending money on other side treats. Like cigarettes. While smoking, maybe the screen would be hazy. Or maybe you could buy crystal meth, too, and you could scratch tickets really really fast.

And so forth. On to idea number two!

Pick a scab

If you want high-brow, go somewhere else. So, the idea here is obvious, right? The screen shows an ugly scab. You can pick at it. Then it bleeds. Then maybe it heals, and the cycle starts again. Probably been done before.


Pop the pimple

Yeah, so apparently this has already been done too, damnit. But what if the pimples could be superimposed on top of the photos in your album?

A few web app ideas

I read somewhere that having a good idea for a business is like finding your sneakers before running a marathon. I’m convinced that focusing on coming up with an awesome business idea is a waste of time. In other words, it isn’t the quality of the idea that separates successful entrepeneurs from all the failures out there. If you can learn to program, you’re smart enough to come up with an idea for a web application that is good enough. The hard part is building the prototype, selling it, training your customers, adding new employees, etc.

Anyhow, since I don’t believe ideas are all that precious, I’m sharing a few side projects I’m thinking about. Feel free to take them. In fact, I’d be flattered.

Just to be clear, these ideas are released into the public domain. When I have some free time I may do a few of these.

Idea 1: make something that helps teachers keep track of grades over the semester

I don’t mean some elaborate tool like blackboard. I mean something that tracks attendance and grades. And maybe a few other things, but not much more. I’ve been teaching for about four semesters now, and it’s a big hassle to keep track of this mundane stuff.

Idea 2: Graphical cash flow / burn rate projection tool

At work, I have to deal with scenarios like paying an extra 10% for some outsourcers to finish a product release that then might lead to increased sales. I want to be able quickly see effects of lots different possible rates of return.

At home, I wonder about stuff like paying an extra $100 toward the mortgage versus putting the same money to the car note.

I want to be able to enter in stuff like recurring payments, starting balances, interest rates, etc, and then see some pretty charts that show the results.

Last idea: workout tracker

I have a hard time remembering workouts. I know I could carry around a notebook, but that’s no fun. I would prefer that after each set, or when I want to take a break, I could send in a text from my phone to some shortcode. The message would have some details of part of my workout, maybe using some shorthand like:

dbp 12 120

meaning that I did twelve reps of dumbbell bench presses with one hundred and twenty pounds.

Then, at the next workout session, I could send in a text message and the system would figure out what I should do.

The system might adjust up weights by 3% for example, or make sure I vary exercises.

There could very easily be some facebook extension that brags to my friends with the details of my workout.

My favorite software quality metric is the income statement

I’ve been working on an open-source project for the better part of a year. It is very complex, very fancy, and has no users except for me. But I love it. It sharpens my skills and gives me a chance to discover puzzles and solve them in the most elegant solution possible.

But in the business world, this approach is downright silly. Nobody writes blank checks to vendors. Nothing in nature works like this either.

When a shark chases down and eats an unlucky spring breaker, the shark burns some calories during the swim, and then gets some calories back during the meal.

On average, the shark has to extract at least many calories while eating as it burned during the chase.

So on to the income statement. The shark makes a good metaphor for a software business. The hunt is the process of acquiring customers. The calories are the firm’s revenues and expenses. A lot of the quality of a software team can be measured in the income statement.

The perfect product is written once and it solves all problems and never needs any updates or extensions or bug fixes. The worst product has to be rewritten from scratch for every new customer and requires lots of bug fixes. Really well-written software falls somewhere between. It supports extensions, but they are quick and safe to do. Bugs can be quickly patched.

It wasn’t obvious to me initially, but this aspect is easy to measure in the cost of goods sold. If a firm lands a deal for $60k, but burns 160 hours rushing some tweaks through, then those hours drive up the cost of goods sold and drive down the firm’s margins.

You can look at the firm’s margins over time and watch whether the app is getting better or worse. Sure, there are mitigating factors, but in the long run, you can’t maintain an attractive income statement and a shitty code base.

My thoughts on roles in software teams

My biz is growing. We’re going from a state where I did everything all by myself to a “real” company. I’ve been working on a mental model to define what developers do.

I’ve boiled it down to three different kinds of work: engineering, consulting, and management. In any real shop, individuals have to be able to wear all three hats depending on circumstances.


A great engineer builds real stuff out of blueprints.

The keyword for engineers is execution. They’re the ones that actually get shit done, and do it brilliantly.

Bad engineers

An engineer that doesn’t love building things is not going to be a good engineer. A bad engineer hacks shit together then hides from peer review.

Good engineers

A good engineer spends her free time reading manuals about obscure technologies. A good engineer gets physically ill when seeing bad design. A good engineer builds beautiful stuff and obsesses about skill mastery.

When a new problem comes up, a good engineer builds a tool that can be used to solve other problems.


This is the task of figuring out the next big thing. This takes a lot more work than just talking to customers and writing down what they say.

Good consultants

A great consultant is a lot like an investigative journalist. They know how to keep asking questions until they know exactly what really needs to be built. Then they write down what they figured out from all those questions in plain language, so the engineer can start working.

Good consultants go beyond transcribing what the customer said and figure out what the customer really needs. Great consultants are able to synthesize product ideas from unordered, generalized customer complaints.


Good engineers and good consultants free the manager from doing anything but planning for sustainable growth. A manager’s single responsibility is to keep the system running over the long run. Managers analyze performance problems and figure out what to do; usually the decision is a choice between training somebody or firing that somebody.

A manager makes sure that her team can handle a loss of a few engineers or consultants as people move around, get new jobs, get hit by buses, or win the lottery.

Good managers

A good manager is really the mom of the organization. She makes sure everyone is happy, working on interesting projects, and generally, reaching their potential. Good managers make sure that as people inevitably leave the team, the team can still function at high capacity.