use a lot of the open APIs out there to bring in additional content. So in this case, we ask you what was the starting point of your road trip and what was the end point, and we create a great-looking Google map for you. Then we prompt you around that, and ask why you were going on that trip. That gentle encouragement makes all the difference.
WR: It sounds like coming up with the daily prompts—which is currently the job of your brother Grant Shellen—is a lot more involved than just sitting down and coming up with a list of random questions, one for each day. You need to pick questions that lend themselves to this multimedia enhancement.
JS: Yeah, the idea was always that the interface can change on a daily basis. It’s difficult—it’s a lot of plates to keep spinning all at once. But we’ve come up with a templatized system behind the scenes to help with that. Today’s prompt fits roughly into our mapping interface. Maybe tomorrow’s will be an offshoot of our image template.
The other part that makes this interesting is that when you look at the individual prompts themselves, people can post their answers to their blogs or to Facebook or Twitter. And we have an aggregated “Most Popular” view, an algorithm that looks at how many times an answer has been viewed, commented, or favorited. We are focusing quite a bit right now on making those aggregate pages more fun, something that would keep you contributing.
WR: Right now, you have to go to Plinky.com to enter your answer to a prompt. But given your focus on integration with other Web services, can you envision having Plinky widgets that would let you write answers directly from your blog or from Twitter or wherever?
JS: Absolutely—we have most of that spec’d out. The idea all along was to make sure this is a portable interface. If you just look at the card-and-stack metaphor we use on the site, you can see it’s something that could easily be placed into a gadget or a widget. The other day, we did release a Google Gadget that people can drop onto their Google home page. But for right now, it’s just delivering the daily prompt. The user still needs to come to Plinky to respond.
WR: How do you think you’ll be able to make money with Plinky?
JS: Obviously, we are a seed stage company, and we have some plans around the business model. You can see that we’re experimenting with some ads on the sight right now. It’s a fairly high-engagement site, and we find that people stay on the site and want to read friends’ answers, so advertising has always been a piece of the business model. But we have a couple of other things we’re not quite ready to talk about that we think should be interesting for businesses and advertisers.
WR: Tell me about your relationship with Polaris Ventures and Sim Simeonov. How did that come about?
JS: When I left Google, as I mentioned, I had a couple of different ideas percolating, and I was pointed to Mike Hirshland at Polaris as somebody who was good to sit down with. I told him about a few ideas, and he said they sounded like good ideas but that they didn’t sound fully baked. And he said “You know who might be interested—Sim, who happens to be in town and I’m sure he’d love to grab dinner with you.” So we sat down over a beer. Sim thinks in business models, and he’s incredibly smart, and we hit it off.
Over the course of the next few weeks and months we met a few more times. I briefly jumped into another company, but decided that was not for me and that I should really pursue my own path. And by about March or April of 2008 I gave him a call and said, “Are you still thinking about this?” and he said, “Absolutely.” So we started putting together the business plan. Obviously, Sim is at Polaris, and he knows the process, he knows what VCs are looking for, and we pitched a few folks inside Polaris and we got a deal done with them. They put in $1.3 million, and we took another $300,000 from angels and other folks. They seem to be big believers in giving people the ability to create. They’ve been a fun company to be involved with.
WR: $1.6 million is on the low end of things for an initial investment round. Do you envision going out for more money at some point?
JS: It is on the lower end of things, but this was only for the seed stage. The things we had hoped to prove by this spring are falling into place nicely, and we absolutely will be going out for another round of funding soon.
WR: Plinky is similar in some ways to Twitter or the status update field on Facebook. Of course, the prompt on those services is always the same: “What are you doing right now?”—whereas your prompt changes every day. But how else are you different?
JS: Early on in the press, we were characterized as “yet another microblogging service.” So some people thought that was what we are. But as my brother Grant is fond of saying, we are only a microblogging service if you don’t like to write very much. There are people who will respond to a prompt like “Defend your vice” and they’ll just say, “Smoking. Never going to quit.” But there are just as many if not more people who are
