The day after my good friend Greg proposed the idea for Teacher Hub to me, I was sure we had a hit on our hands. 7 months, 1354 lines of code, and one “pivot” later, I called it quits and moved on.

Chronologically, from the beginning

Greg’s wife is an “early-stage” teacher (a few years in), and given the horrendous job-security that newly minted New Jersey teachers have currently, she’s dealt with having to teach entirely new classes year after year. All new classes => all new needs. New classroom supplies (largely teacher-purchased or teacher-subsidized), new curriculums to learn (and inevitably update), and possibly a new school to get used to.

Her itch: wouldn’t life be better if there were an online destination where all those things could be found easily and cheaply? It would be a place where teachers could trade, barter, sell, or share their wares, skills, and advice. A place where teachers could meet other teachers from their area. A place where teachers could write about their experiences — the good, the bad, and the ugly.

A “Teacher Hub,” you could call it.

I loved it. It seemed like a real need in an interesting industry. And I was desperate to step into the startup ring once more (my first startup, back in 2006, was a movie social network called Reel Critics that never launched).

Start coding, talking, coding, talking

First thing I did was start coding the boilerplate and basic multi-column layout. I had been simply writing new SQL code and the occasional unordered list for the past year, and was just excited for an excuse to build something from scratch.

We scheduled weekly meetings to keep things on track (keep on what track? we hadn’t laid any tracks at all), which one of us usually showed up late for. I was 37signals-crazy, shoving all my clients and projects into Basecamp, writing roadmaps in Writeboard, tracking life tasks in Ta-da List. So of course, our meetings were in Campfire. Text-only. So the rate of conversation-to-useful-work was diminished for us by the very nature of our communication medium.

One of our first goals was to get Greg up-to-speed on programming. We weren’t sure how much he could contribute code-wise, but I was hoping to get one more person coding. The last time I was the only coder on a large-ish project, I got tired after a few months. Nobody to talk to and pump me up creates a tough gig.

Let’s get something out of the way. If you’re starting a startup and someone wants to teach themselves programming in the process, don’t expect good results. This is not a knock on those people. My advice is to look at the priorities of the business and the priorities of the person. If either of those points away from a need or desire to be a programmer, then this could be a waste of time for everybody and for the business. There’s a school of thought that if you have a startup idea, you should teach yourself to code, or that everybody in the startup should be able to code, but the fact remains that there is a lot of stuff that needs to be done at a startup, and if someone’s motivations aren’t conducive to programming, don’t get hung up on that. Do something that you can do already, and do it now.

So those first few months, while I was still living in Venezuela (Greg was in New Jersey), we’d spend our time doing the following: coding, setting up Greg’s RoR dev setup, setting up the staging server on my Media Temple VPS, talking about doing research on the industry of teacher-oriented websites, doing some nominal research on said industry, and debating with gusto about the financial aspects to our business model.

Let’s Align our Interests

All of this meeting stuff was an attempt to align our interests to the goal of building Teacher Hub. We were trying to get on the same page so that we could work on the same thing (programming our Minimum Viable Product), but our differing skill sets kept us drifting apart throughout the week and then struggling to re-align our interests and goals during our weekly meetings:

Instead of what we were doing, we probably should have specialized in what we were each capable of already, keeping our end-goal in sight and on the same page, but not concerning ourselves with making sure we were both contributing the same things in the same amount as each other:

Next time on “Startup Gone Wrong”…

We’re only 2 months in, and Edyta and I are about to realize that Venezuela is just not going to work out. Find out what happens to Teacher Hub (and my programming life) as we start our journey back to the USA.

This post was graciously edited by Marc Ubaldi

Around my internet1, there’s been a recent meme concerning dedication to starting your own business. It’s not unique to our time, but over the past week it feels like everything I read, watch, or listen to is talking to me about the need to devote yourself fully to whatever it is that you believe your business to be, otherwise it will likely never get done.

Dan Benjamin and Merlin Mann talked about it on the latest episode of their podcast Back to Work, Jim Coudal implored us to build your beer cozies today, and… those are the only two I can remember right now, but it feels like I’ve been pestered with these messages for the past week non-stop.

Listening to these smart, successful exemplars in my industry, I realized that I had essentially followed their advice. I spent all of 2010 as a full-time self-employed freelance programmer, and now, in 2011, I work a “corporate” job while relegating projects of passion to my off-hours. What happened?

Some backstory:

When I finished my Master’s degree (you don’t have to call me “Master” if you don’t want to) at the end of 2009, I knew exactly what I was going to do. I was going to take my 2 current freelance (programming) clients, find a few more, and eventually hire employees and sit back while they make me lots of money. I was even going to expedite the “retire on a tropical beach” part of it by setting up my business in Porlamar, Venezuela. By my back-of-the-napkin calculations, between my current meager freelance income and Edyta’s doctoral scholarship, we would live quite comfortably in relative solitude and peace in the tropics, given the expat-favoring pricing in Venezuela.

The plan was to stay there for 1 year. We lasted 3 months.

Then, 6 months after we moved back to the U.S., I was looking for a “normal” job.

What happened? Why?

Well, our general reason for leaving Venezuela was that we couldn’t get a reliable internet connection — a vital tool in both of our fields of work.

But in general, I found that while many of the aspects of freelancing were empowering, other aspects were putting my brain’s anxiety receptors on high alert. You’ve heard about the empowering aspects already — no boss, working on what you want, etc. — so I’m only going to explain how the empowering aspects lost out (for the time being) to the anxiety-inducing aspects.

• I loathed searching for new clients. I would stare for hours at the 37signals gig board (defunct) and the Authentic Jobs freelance listings, thinking to myself that I couldn’t possibly sell myself as capable of doing those jobs. Or maybe the jobs had weak descriptions, making me wonder if the clients would be flaky.
• Lonely. That’s what I felt while working in my home office on sites with no designers or programmers other than me. When we moved to New York, I had no excuse not to put myself out there at hackathons or conferences, but I convinced myself that sitting at home working was time better spent.
• Once you’re locked in at an hourly rate, it’s hard to raise your rate. I had almost 30 hours per week of work to do, but I was still charging my cheap college-student rates to my most trusted clients. Not a good thing when you consider my lack of new clients.
• You still have to find time to do the things you love. Despite having the luxury of setting all my own hours, I still found that I had to make time for my projects of passion outside of client-work time. If you’re not working on your startup full-time, then you’re just not working on your startup full-time. Not much different than working a “normal” job and coming home to startup work.

Overall, these things (and other, less explainable things) contributed to my anxiety over running my own business. And this doesn’t even get into the anxiety of an exciting startup project turning sour (another post, another time).

So I suppose this is where I put in a little warning to all the would-be self-employers out there. Be as aware as you can be. Which is probably not enough. You can do it if that’s your goal. But the alternatives are not so bad, if you ask me.

This post was graciously edited by Marc Ubaldi