Techstars Demo Day: Well Choreographed Process of Insanity At Its Best

My alarm went off that morning at around 6am. Normally, through the entire Techstars program which began in late June, my alarm would be set at 7:30 or 8am. However, this day was Demo Day. This day was the culmination of everything we had worked for during most of September.

For those not familiar, Techstars is a top-tier accelerator program meant to help early stage businesses navigate the treacherous waters of building and growing your business to a point that can help you raise another round of funding. It’s also a program to help Entrepreneurs learn the ins and outs of business in a highly compressed and fast-paced program lasting 12 weeks. During this time, Entrepreneurs get access to some of the country’s best business people through mentorship and guidance. The entire program ends at a large scale event in which all of the companies demo their companies in front of several hundred investors, business people, and press with the goal of celebrating their completion of the program.

For us, the goal of the event was to garner enough interest from some investors that could help us go back to Portland, OR. with the ability to close out our seed round. As such, we knew our demo day pitch had to be polished, well thought out, and well rehearsed.

As I left my apartment in the West Loop area of Chicago I have been calling home all summer, I found myself reciting my pitch over and over. I was meeting my Co-Founder Phil at the Sheraton where we would spend most of the morning going through 10 different suites which contained up to 8 individual Investors representing firms or themselves. This process of pitching 10 times in a row before even getting to the main event was meant to do two things. The first was obviously to get you used to pitching your demo day presentation so many times in a row that it was simply muscle memory once you made it onto the big stage. The second was to enable you to answer questions in front of people who have cut checks to other Techstars companies in the past.

As we entered what would be known as our “home room” we worked to set up the room the way it would best work for someone awkwardly presenting in a large hotel room. We set up the chairs, connected our laptop to the TV, and ensured the snacks were all organized to greet our guests when they arrived. Then we left. We headed to our first room where we would be pitching about 30 minutes later.

The morning began with us pitching to a small, but friendly group of Investors. Most were there to genuinely look at what they could do to help through an investment, but some were there to just be friendly members of the audience should anyone start to be aggressive. These were called “friendlies.” These people were strategically placed to help guide the conversation if we missed anything or to simply be the loudest person in the room clapping.

Room by room we made our way through the 10 suites. We pitched to rooms filled with somber quiet groups and to some that we more gregarious. We got some great questions, some awesome feedback, and even an investor who let out a “Holy fuck!” in the middle of our pitch.

By the time we had gone through all 10 rooms, we knew we had the pitch down without needing to do much more practicing. So we did what most Founders did that day, we jumped back on our laptops and continued to do more work.

Later in the afternoon we headed down to the House of Blues in Chicago where the actual event was taking place. Phil and I jumped in our Lyft and began the short ride over to the venue. When we arrived at the venue the doors had already been opened to the public. We sat our gear down and headed to the area in the venue our MDs had informed us we needed to hang throughout the event.

As the event began, more and more people began to pour in. Everything kicked off with Chris Gladwin of Cleversafe touting the toughness of Chicago and outlining his own path as an entrepreneur.

As the demo day pitches began the energy in the venue continued to build. Each company went through their 8 minute pitch with no real hiccups to speak of. Then it was our turn. We made our way backstage to get mic’d up and get ready to step on stage for our turn to present. This was our moment to shine.

We had a great mentor by the name of Joel Grossman who is the CTO of Leapfrog Interactive who introduced us on stage before we presented. It was such a great experience to have someone we respected and got to know of through the program introduce us to the crowd.


(from left to right: Phil Taylor (CTO), Joel Grossman (CTO @ Leapfrog Interactive), Josh Carter (CEO))

After Joel made the intro, I stepped on my mark on stage. The place had thinned out a bit after the break, but it was still a great audience who were super receptive to my pitch. In fact, during my presentation someone let out a “Holy shit!” right in the middle which I happily called out. After my 8 minute pitch, I had felt a great sense of relief. It was over. All of the practice, the frustration, the time spent trying to tweak our pitch was done. We had made a small misstep at the beginning, but for the most part we did great.

Looking back on that day I can honestly say it was such a thrill to go through that endeavor. It’s almost like going through a rite of passage. We had been tested, gone through a tremendous amount of stress, and made it through the other end better. I feel like Phil and I have the skills needed to better tell our story and give ourselves a better chance to build a business with a great chance at success.

Even today as we sit three weeks removed from demo day, we’re about to pitch to an investment group and going through our pitch I still feel like I could go through it with zero issues. We’ve learned a life skill that will be with us forever.

Josh Carter

CEO/Co-Founder @ BrightWork (Techstars Chicago '16), ex-Twilion, Father, US Navy Vet.

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