I just got back from Y Combinator Demo Day, Summer 2008. For a startup
fanatic like me, it’s hard to imagine a more fun use of a few hours. I got to
watch 20 back-to-back, rapid-fire startup demos. 
Here are some of my initial reactions and thoughts on the newest cohort of YC startups. Note: Like most OnStartups articles, this article focused on the entrepreneurial perspective (not the investor perspective). The folks that should (hopefully) get the most out of this are the YC startup founders themselves.
Notes From The Y Combinator Summer 2008 Demo Day
1. Best Cohort Yet: Overall, in my (highly subjective) opinion, this is the best batch of YC startups yet. I think I have a bias (which has been tempered over time) for startups that have demonstrated some thinking around things like monetization and revenue, and that might be influencing my thinking. The current cohort, on average, seemed to have a stronger emphasis on not just making something people want, but something that will yield revenue, and (gasp!) profits. Good stuff.
2. Presentations were better than what I’ve seen in the past. More fluid, more polished, more effective. My hat’s off to all the YC startup founders that presented today. You guys did a great job! Having said that, it’s not a totally fair comparison. You guys do have the advantage of many more YC founders before you that you can learn from. I’m guessing that Paul, Jessica and the rest of the YC crew are also getting better and better at nudging you in the right direction when it comes to Demo Day presentations.
3. Tip: Use your precious minutes: The Y Combinator team did a great job keeping things moving, and I think the format of Demo Day works well (6 minutes per presentation, no audience questions). One quick tip for the presenting team: If you are doing the presenting, you should begin with your message even while your team member is setting up. Don’t wait for the slide deck to come up on the screen. Don’t shift the focus to your buddy who is switching out the cabtes and stuff. Don’t wait. Just start delivering your message. In your preparation, come up with introductory remarks that don’t rely on your first slide being up yet. When you only have a precious few minutes, 30 seconds counts.
4. Don’t use gender stereotypes: This one’s going to be a little touchy. A few of the startups today used examples and screenshots that were um, a little too “gender-stereotypical” (that’s a semi-polite way of saying they were too far down the spectrum towards being sexist). I can understand and appreciate that most of the YC founders are young males in their 20s. But, my advice would be to resist the temptation to use scantily clad women in demos. It’s both inappropriate and sub-optimal.
5. Answer the question you know people are asking themselves: Once you start doing presentations a lot, you begin to realize that there’s a “pattern” to the kinds of quesitons people have in their heads. The same themes recur. Do what you can to make it as difficult as possible for people to dismiss you because they’ve got that one big “obvious” question/objection/whatever. For example, I thought the Fliggo team did a smart thing by closing with this nugget: “I know you’re asking yourself, how are these guys going to make money…I’m glad you asked…”. You don’t necessarily have to answer the “how do you make money” question (though that’s not a bad thing), and you don’t even have to frame it as a quesiton. Just try and address the most obvious things people are likely to wonder about.
6. Tip: If you’ve got traction, share it earlier in the presentation: There were several startups that had pretty impressive early traction (like users and revenues). They didn’t talk about this until later in the presentation. I’d suggest possibly getting this message out earlier in the presentation, because it will grab people’s attention and cause them to listen more intently to the rest of your story. Imagine an opening sentence that is something like this: “Hi, we’re XYZ. We launched just a few weeks ago and we’re getting some encouraging early evidence that we’ve built something people want…Here’s what we’ve learned from our 14,000 users…”. I’m not suggesitng you use that exact sentence, just a thought. When dealing with investor types, remember that folks have short attention spans and you’re best served by grabbing them as early as possible with something they care about.
7. Memorable sound-bites are not just for TV: I’m generally not a big fan of over-preparing for presentations (more often than not, sounding natural is more important than sounding polished). Having said that, some clever, funny, well-crafted sound-bites thought of in advance and added to the presentation are a good thing. They’re particularly good for bloggers and media types that might cover you. For example, the PopCuts folks had this great snippet: “The only way to get famous on BitTorrent is to get arrested.” Simply brilliant.
8. Audience participation/engagement works: A couple of the startups were able to work their demo such that the audience was “involved” in the demo itself. Although this is hard to do, it’s valuable. It also helps a lot when you get audience members to do something (instead of just sit there and listen).
That’s all I have for public consumption. However, I have notes from each of the presentations. If you were one of the startups that presented today and want my quick thoughts or feedback, feel free to email me.
I just noticed a great summary write-up of today’s event on Scott Kirsner’s Innovation Economy blog. If you’re not yet reading Scott’s blog, you should be.
Best wishes to all the Y Combinator startups. It was great to see you all and chat with many of you at the close of the event. Knock ‘em dead next week. In the meantime, some closing advice: Get some sleep!