MattMaroon.com

Demo day was Thursday. Oddly enough, it started with me almost getting arrested. Late Wednesday night Chad and I decided to go grab a couple beers at a great little neighborhood bar called the Orleans (my favorite thing about Boston is the beer selection) and on the way back (technically Thursday morning) nature started calling. I decided to answer it right there at a building that I think is part of Tufts’ campus. Within seconds of me dropping trou by the nearest tree, Chad started yelling “cops, dude, cops”. It’s been a while, but I’ve heard that call enough to know how to react.

I immediately zipped back up and started walking home like nothing out of the ordinary was going on. I was quite a distance from the sidewalk when they spotted me, and I was more than a little buzzing, so it definitely wasn’t good. Two cruisers pulled into the parking lot and one started asking us questions. “You weren’t pulling on doors were you?” Luckily I was a fairly well-dressed white guy, with a shiny Movado on my wrist, so when I said “nope, we’re just checking out the area” he at least pretended to buy it. That was good enough for me.

I got a good night’s sleep, thankful not to be in the tank. In the morning I found myself oddly nervous. I’m not used to public speaking, since I’ve really never done it before, and I knew I’d be presenting to 50 investors. At the very first Y Combinator meeting they passed out two t-shirts, one of which said “strap on some plums”, referring to, of course, the courage needed to speak to investors. So I decided to strap on some liquid plums, with a couple shots of Don Julio Reposado (the finest tequila known to man). Alcohol in very small quantities (I’m a semi-professional drinker, so two shots to me is basically non-existent) is a well-known performance enhancer in the poker world, and I knew it wouldn’t disappoint.

Despite the fact that it had more or less worn entirely off by the time we demoed (we were 6^th in the order) I feel like I nailed it. John had a bit of a problem with the mouse and left me hanging on one slide for what seemed like a minute but was probably more like 10 seconds. Other than that (and I don’t think it detracted much) our presentation kicked ass. As I said earlier, we avoided text (we had only one frame with bullets) and instead stuck with relevant pictures, with which we told a story. The logical flow of the presentation was, I feel, very strong, and as a whole it was very well-received.

The buzz seems to be that we were one of the top few Y C startups from the batch. I thought we’d fair better with actual investors than we did in the internal polls we had at practice days, given our geek-unfriendly subject matter. So far I think I was correct.

Building that demo took a tremendous amount of effort. John and I did it together, and we argued over the finer points for hours (though we both agreed on the general principle) but I think it ended up all the stronger for it. Working with John is often like that I think. The process is a giant pain in the ass, but the end product is amazing. And we can’t ignore the fact that without Chad’s hard work, we wouldn’t have had much of a site to show, since we do flick from PowerPoint slides to a live demonstration and then back again. He also made some of the technical magic of the presentation happen. All in all, we all came together and made a demo we were extraordinarily pleased with.

And so, apparently, was the audience. We’ve had tons of feedback from them so far, and it’s all been good. One of them actually shot us an email saying “let’s talk” in the middle of our demo, and multiple others have expressed interest in talking.

One angel met with us the next day. He was a guy Paul Graham knew well and spoke highly of. We took time out of packing to meet with him Friday, and he seemed very enthusiastic. He has a lot of startup experience, was extremely understanding of our total lack of knowledge of the logistics of the industry (we have a ton of experience relevant to our business, but the tech world is, in many ways, alien to us) and struck us a genuinely nice guy. He didn’t pull any of the tricks we’d been warned about (exploding term sheets, etc.) and, in fact was quite the opposite, wanting merely to be kept in the loop as we put together a round of angel investors. He seems like a great guy (and John and I are both phenomenally good at reading people, so we’re pretty confident when we say that) with a lot of value to add beyond money, so we definitely hope he will be part of the eventual team.

We’re pretty sure at this point that an angel round is the way to go. Not positive, but definitely leaning that way. From what we’re hearing through the grapevine I suspect we could get VC funded, but giving up a smaller percentage of the company and having a more favorable board and other such terms seems to be the way to go. This is the sort of business that I wouldn’t feel comfortable with someone else having control over, and I think any savvy investor will agree with me on that, since it plays to our experiences very well. I also think we can become profitable very quickly, so one good angel round might be all it takes.

I’m writing this on a plane now to San Fran. We’ve got a hell of a lot to do on this trip. We’re hoping to meet with two other potential angel investors (we’re trying to put together what amounts to a medium to large sized angel round, so we’re going to need a group of them). We’re also looking for a place to live, since we plan on moving out in early September. I’m hoping to meet with a few different marketing/PR types I’ve met along the way to get an idea as to what services they offer and at what prices. We might meet with some attorneys too. And on top of that we need to practice the demo a few more times to stay on top of it and try to keep advancing in terms of code.

We moved everything back to Ohio on Friday and rearranged the flights so we could leave from and return to Cleveland. After this trip it’s back home for a little over a week, and then off to Silicon Valley indefinitely. Hopefully once we’re there we’ll be able wrap up the funding process quickly and get back to making something people want.

This entry was posted on August 15, 2007 at 2:24 am and is filed under Startup . You can follow any responses to this entry through the RSS 2.0 feed Both comments and pings are currently closed.