I Had Ten Dollars

I started a blog for showcasing cool side projects three weeks ago and it’s been a great learning experience so far. I’m so lucky to know people who are willing to volunteer their time to this project and work through the interview process with someone who’s still figuring it out.

Thanks to Ryan Wolf, Greg Leppert, Carlo Flores, and Jen Lowe for getting me started.


After spending almost a month with this design I’ve realized that I have a few issues. For one, I’m using a lightly modified version of The Setup from when Daniel was using Jekyll as his static site generator instead of Salt. The Setup is a great design for interviews focusing on individuals. I think I Had Ten Dollars is suffering from a tension between my desire to show off the creators and the concept’s emphasis on projects. Right now, while the interviews themselves are project focused, there isn’t really any detail about the project in the homepage view and the only images on the site are portraits of the creators. I’m not sure how that’s affecting browsing behavior, since there are only four interviews up right now and the average pages viewed per session is about three. Still, I’d like to make it easier to browse and for the site to have a more elegant internal logic to it.


I’ve also gotten some feedback that the site’s content feels a little disjointed because my questions are different for each person and there’s no real tie between the I Had Ten Dollars name and the interviews themselves. I’ve tried asking people about the domains they have sitting idle, but the people I’ve gotten feedback from tend to gravitate towards a theme section where I’d have the interviewee register a new domain on the spot or provide a domain and have them figure out what type of project it would be for.

I haven’t figured out how I want to address this yet, but I do know that I like varying the questions. I would be really bored if I just had a set of a few questions to ask and could email them out. Which brings me to interviewing!


All of the interviews that are up now were done over email, which allows my volunteers to answer them when it’s convenient. For the most part, I think email has worked out pretty well. I can’t really react to answers for followup questions, but I can organize my questions in a way where I think the subjects kind of cascade nicely. I can try to predict their answers and build with transitions in mind. Occasionally I produce big chunks of text because I’m trying to create context for my actual question. I think that looks kind of weird on the site, and isn’t necessarily that useful for the reader, but I’m unclear on the ethics of editing an email transcript since the person answering expects it to run more or less as they saw it.

I’ve been toying with the idea of breaking up my interviews into two emails, one for background and then one for follow up questions. If anyone who conducts interviews over email has tips, I’d be interested in hearing from you.

Helpful Resources

I’m using Jekyll and GitHub Pages for I Had Ten Dollars. One thing that created a decent amount of consternation for me was that Pages doesn’t accept Jekyll plugins. Charlie Park has a good post explaining the issue and how deploy just the generated content to Pages.

This is my second time using Pages, and I’ll probably use it a bunch in the future. As someone who’s kind of a dummy when it comes to DNS stuff, I’ll probably be using David Ensinger’s post that tells me exactly what to type and where to type it a bunch too.