Shutting Down a Dream

When I was 17 years old, I wrote a little Applesoft BASIC program to help myself memorize vocabulary for my Spanish class. When I went to college, I wrote a new version for the Mac, adding special features for Japanese. Senior year I wrote two new versions – one for my senior project, another for a class in which we were supposed to learn the basics of five ancient languages (I adored the professor, but he was a little meshuggah). Another version when I started studying French. It became a bit of a joke – every time I started studying a new language, I’d first spend a lot of time rewriting my vocabulary drill software – if I’d only spent that time on the languages themselves!

And so, a decade ago, when I left the video game industry and had some time on my hands (thank you, San Diego real estate market!), I used this project to teach myself web development. Every version up until then had been for an audience of one – fine for my purposes, but completely unusable by anyone else. So I set out to build the version for the masses, the final version – the version that would allow me to stop writing and rewriting the damn thing.

I didn’t mean to make it into a company, it just kind of happened. Well, OK, I incorporated three weeks after quitting my job, but it wasn’t what I was planning originally. I really just wanted to get it out of my system. And so, all of the learnings from the prior decade and a half, poured into a product that no one would ever pay for. Who (other than me) would pay for a flashcard system? Sure, there are a couple of them out there (God love ’em), but not anywhere near enough even to get ramen profitable. So I went back to the drawing board, and went after a market I thought would be interested.

Teachers. They could get it for free and have their students pay – everyone wins! The teachers set up homework, the students learned vocabulary, and I got paid. Somehow, though, the teachers didn’t find me on their own, so I ended up doing a lot of cold calls. 100 calls to talk to 10 people to get 1 in-person demo, frequently in another state. I got in the car, put on the suit, and did the demos. I put together some signage, set up a booth at ACTFL, IALLT, and military linguist conventions. My parents saw a lot of me (they live near a lot of colleges), I stayed in a lot of cheap motels, and slowly, I built a list of customers. Not a lot, never enough. Harvard, Yale, Brown, and other top schools were among my customers, but I never made the “big score” – the state school with tens of thousands of students.

I integrated with PayPal and Authorize.net. I spent a huge amount of time doing data entry – I promised the teachers I’d enter all of their vocabulary lists into the system, and record audio for all of their words, before that critical first fall semester – and there’s an entire summer of my life that’s missing, lost time. Princeton Spanish reneged at the last minute, which taught me the value of communicating progress along the way. The rest followed through, and became some of my best customers, but with one or two exceptions, I wasn’t able to leverage one language department to get an entire school.

It was growing, but too slowly. I was down to the bottom of my life savings. I stopped dating. I ate a lot of canned soup and peanut butter sandwiches. I borrowed money from my parents. I lost weight. I had insomnia for a month and a half.

In 2006 I started talking with a potential acquirer. But there was a blizzard, and we missed a crucial meeting, and in the meantime I got in contact with an old boss who was interested in getting involved. So I followed one path instead of another.

We got some angel funding, brought on some additional people, and tried to make a run for it. I won’t go into the details, other than to say that we made huge mistakes, and didn’t get lucky. After two and a half more years of trying, the money ran out, and the world economy suddenly collapsed. And so I went out and got a job.

I kept the site running – what was I going to do, shut it down? It was making some money – not much, but it was paying for itself – and though I was married, we didn’t have kids, so there was time to do stuff after work. And then we did. And still I kept it going. The teachers who depended on it were friends – I’d known them for years now, they were real people, not just users. And there wasn’t anything remotely like it out there, so what would they do? I felt like a TV executive pulling the plug on a great series that couldn’t make the numbers – how do you face the fans? How do you respond to their emails?

And then my father passed away. This was a wakeup call that took a long time to ring. I decided to shut down the site, but had to give people enough warning. The date was set for the end of the year. I put up the notification. I desperately tried to ignore the pleading emails. And at the last minute I blinked. Maybe it could still work out. Maybe if it just made more money? I raised the price on students, and started charging teachers (which I had always balked at, before). Maybe I could still make this make some kind of economic sense? The teachers were relieved, and happy to have their school districts pay. Strangely, though, this caused more trouble. The combination of checks, credit cards, purchase orders, temporary enabling of accounts while waiting for checks to arrive, etc., took more and more of my time. And then I had a second child.

When you have children, you can have exactly one hobby. Anything else is an exercise in futility, self-deception, and ineffectiveness. Cooking healthy food is a hobby. Exercising is a hobby. Maintaining a website is a hobby. Writing a blog is a hobby. Bringing work home is a hobby. You have time to do exactly one thing after your kids go to sleep, if you want to do it well. The pointless waste of time had to go.

It was time. A new date was set. That date was June 30. I’m a little late, but just because I need to provide a vocabulary export tool, and I haven’t gotten around to it. This time it’s going down, and that’s that.

I suppose this is part confessional, part apology, part cautionary tale. Am I glad I did it? I’m glad I had the courage to try, and I’m grateful for the insight it gave me into what it takes to build a business. If I could go back in time would I do it again? No. Perhaps some other startup, some other time, but this took too long, and was too painful. My love for the product didn’t blind me to its failure, but it did prevent me from failing faster. It’s taken such a long time to die – I decided to start looking for another job five years ago this month – that I no longer feel more than a small ache. It’s long since passed from beloved child to albatross.

And so, shutting it down. It will stick around for another month or so (so that teachers can get their materials off of it), and then it will be gone. There are other things I dream of doing with more time, and less mental energy spent worrying about this. Getting back in shape. Translating ドグラマグラ. Writing some one-off iPhone and Android apps. But first, I need to clear my plate.