Lessons on pitching from one CEO who attended Techstars’ Demo Day.

By Sarah Press (CEO, Project Fixup)

Last week, I was up on stage introducing my startup Project Fixup to a packed house of 500 investors at the House of Blues. It was the culmination of months of preparation, mentorship, and a fair bit of stress that started when Project Fixup was one of 10 companies accepted out of over 900 applicants into the Techstars Chicago summer accelerator.

I learned a number of things in preparing to condense my entire business into a 10-minute presentation. Here are five that stand out:

Tell a story

There’s a reason presentation coaches agree that incorporating stories into your delivery is an effective tactic. While charts, numbers and statistics are essential, it’s the narrative around those numbers that really drives the point home and makes your story stick.

In my case, I led with the problem Project Fixup is solving – namely, that people waste too much time browsing through online profiles. I then shared the experience of a particular couple that met through our service, and each subsequent point referred back to this couple. By the time I got to the rest of the numbers, the audience could grasp the context behind them.

Practice, Practice, Practice. Then repeat.

It takes a surprising amount of preparation to come off as effortless and confident. During the month of August, I met with Troy, the Techstars Chicago Managing Director, every single day to brainstorm, revise, dissect, and practice my pitch to make it the best it could possibly be.

Pouring 60-plus hours of preparation into one ten-minute presentation may not sound like the most enjoyable way to spend the last month of summer, but the difference between my practices one week prior to Demo Day and the night of the event made it all worth it.

Remember That One Size Doesn’t Fit All

Every company and pitch is different, and the content and tone of your pitch should reflect the business. In my cohort, TradingView and WebCurfew highlighted their deep domain expertise. SimpleRelevance and Nexercise showed their incredible existing traction. Pathful and SocialCrunch emphasized the impressive complexity of their product. Sqord and CaptureProof explained how they were literally changing the world. FindIt showed how their product just really was that awesome.

All these story lines can work (and they all did – everyone did a great job). In our case, I run a dating startup. We highlighted all those elements in our speech, but did so in a way that was lighthearted and fun because of the nature of our business. And that worked for us.

Seek Out People Who Make You Better

By mid-August, I had put together a presentation that I thought was pretty good and was fully prepared to coast for the rest of the month. About ten days prior to Demo Day, I showed it to Zach Kaplan, the CEO of Inventables and my favorite mentor throughout the Techstars program. He told me on no uncertain terms that he didn’t like it, that I could do much better, and that we needed to start over. And we spent the next five hours on that Sunday rewriting the entire story.

That’s what real mentorship is. It’s not about telling you that you are good. It’s about telling you that you can be great and helping to get there; even if it means scrapping your entire pitch and starting from scratch -multiple times.

Have Fun With It

For all the work and planning, you never really know what will happen when you actually get on stage. You’ll mess up a line, the audience will chuckle when they aren’t supposed to and be silent when you’re expecting a laugh, the lights will momentarily blind you, and more. The real secret of a great presentation is to not stress or worry and just enjoy being up there.

At the last minute, I decided to add the line “But never fear, single universe, for we are Project Fixup!” into my pitch right before explaining how my product worked. It was undeniably silly, but it made me smile (seriously, try saying it, it’s impossible not to smile) and kept me smiling throughout the rest of my speech.

Throughout the entire process, the best advice I got came from Sam Yagan, who said: The difference between a good presentation and a great one is energy and confidence. Be confident that you know what you’re talking about and have a great energy and enthusiasm for your company and the audience will definitely catch on.

Know what? He was right.

Think you’re ready to pitch? Sign up for our PITCH competition. The deadline is Sept. 15. APPLY HERE.

Photo by Andrew-Hyde / Flickr.

sarahpress (1)About the guest blogger: Sarah Press (@spressto) is the co-founder and CEO of Project Fixup, one of ten companies in the 2013 Techstars Chicago class. Project Fixup is an offline dating company, focused on getting members away from their computer screens and out experiencing their city with someone new!