Startup Weekend Lesson Learned #1 – The Pitch

Startup WeekendThis last week was crazy, mostly because I spent all last weekend coding, marketing, pitching, and navigating the intense and creative atmosphere of Startup Weekend SF (#swmobile). If you haven’t been to Startup Weekend, you should because it’s the best place to get a quick feel of what it takes to run a startup and one of the best places to find a co-founder for your next business. (Aside from startupSQUARE of course!)

startup weekendOne of the great things about Startup Weekend is the amount you can learn in a short time. It’s really a lean startup practicum. So I’ll write a few quick notes about what I’ve gotten out of it, starting with the big pitch at the end of the event. My team was called KissMobs and we made a mobile dating app to create a flash mob singles scene.


Some people get nervous and talk fast because they’re trying to pack a lot into a five minute presentation. This can be mitigated by a lot of practice and we did so while timing the presentation. It clocked in at 4 minutes, which should have been plenty of time. But there are always kinks.

I started out too fast, then noticed it by my second sentence and regained the pacing I’d rehearsed. Then I went one step further and slowed down another notch to “compensate” for my nervousness. The result? “ONE MINUTE LEFT!” and I wound up rushing the last part of the presentation.

Another tactic is to have convenient hyperlinks interspaced in the presentation so you can skip sections easily if you’re running behind. I used to do this all the time and completely forgot about it for this one.

Button Pushing

This one is simple, we had six people in our group but I wound up advancing the slides myself. This locked me to the podium and more importantly, distracted me instead of allowing me to focus on the audience. If you don’t have a clicker, it’s great to have someone else in your team advance the slides for you.

It does take a bit of rehearsal because the timing of slides is a lot like the punchline of a joke. Bad timing can ruin it.

Pitching deck slides are like punchlines. Bad timing can ruin it. Share on X

Best is to lead into a slide so that the slide augments what you’re saying. If you advance to the “Problem” slide before the speaker has introduced it, the audience isn’t listening to the speaker, they’re reading the slide. That’s not good.

Have a Plan ‘B’

Everything at Startup Weekend is rushed, so it shouldn’t have been a big surprise that our demo went from “almost done” to “totally screwed” to “it actually works!” within the last two hours.

But of course, the presentation had to be modified to account for this and I wasn’t prepared. So I spent the last hour or so creating slides to fill in the blanks for part of the demo and then deleting some.

Better would have been to assume that we’d have no demo at all, then just cut out slides depending on what we actually finished. As is, I could have cut a lot more out but got frazzled at the last minute and didn’t adjust properly.

Get a Second Projector

If you’re doing a demo, odds are that you’ve got admin screens, a mobile client, and a ppt. You can’t fit all that on one screen let along one projector. Flicking back and forth between screens is time consuming and distracting. Have a second projector to show the demo while you reserve one screen for your presentation.

Rehearse the Demo

We did rehearse the presentation, but not the demo. Granted, the demo only got finished a couple of minutes before hand but still…big mistake. The demo is the key part of a Startup Weekend presentation and I definitely wasn’t polished enough. We could have shown a lot more cool stuff and as is, I don’t think we conveyed the awesomeness of what the KissMobs development team was able to accomplish in 54 hours.

Leave Room for Questions

Our presentation was funny (or so we thought) and the laughs in the audience seemed to agree. I was flying high by the end of the presentation. Sure, things could have been better, but I was excited for the Q&A since I could elaborate on some of the points I had to rush through. “Questions from the judges?”


Silence is the death knell. It says your presentation wasn’t interesting enough to ask more about.

We only got one question which was pretty straightforward and had three minutes left which we had to abandon. In our case I think we failed on two points here.

First, our presentation was perhaps too funny. It had stick figures in inappropriate poses and honestly, our business concept was not exactly trying to solve global warming. It was a mobile dating app. So one thing that could have gone wrong is that people thought we weren’t being serious enough.

Second, we didn’t leave any room for questions. We had a solid business model proven many times over (basically we created a flash mob ladies night with a mobile app). We had a very basic customer problem (people are lonely and looking for a date). There was nothing mysterious about it.

A good tactic to avoid this crushing silence is to leave some details out, or better yet, insert a controversial statement into the presentation. You can have a prepared answer to the presentation and if you’re lucky it’ll distract people from a controversial aspect of your business plan that you haven’t quite worked out yet.

Summary of Lessons Learned

  • Practice, practice, practice… including the demo
  • Watch your pacing
  • Get another projector
  • Be prepared to skip sections
  • Plant a slide to provoke questions

Discussion (0 comments)

  1. Pingback: Startup Weekend Lesson Learned #2 – Customer Development | startupSQUARE's blog

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