It’s 6 o’clock and I’m on a bus headed to Chicago. Our destination? 1871, Chicago’s premier digital startup incubator. But you might be wondering why we’re commuting at this time. After all 1871 does get pretty quiet after 6pm. While we do work there occasionally, this isn’t to perform regular company activities. We’re going to compete in a business competition!

In reality our business is competing every day, there’s just no judges or press releases about those competitions, just value and clients (which are prizes that give life to the company). This time there were a few judges and cameras. The event was sponsored by J.P Morgan Chase and tip of the hat to them for not using any event time to promote their agenda like so many other sponsors!

There was some pretty stiff competition this year as well. Always a good sign that the event is worth participating in. Previous winners of Power Pitch went on to do some incredible things. Some started other successful companies (tldrLegal, Xcube) and others went to prestigious universities (Berkeley, Stanford, etc). Needless to say, I was nervous. But one of my teachers offered me some sage wisdom that has stuck with me and always cures my anxiousness.

Being nervous is good. It means you care. It means you’re prepared

So actually, I should be more worried if I’m not nervous. Incredible. With that in mind, I continued to practice reciting the pitch awkwardly at the 1871 auditorium while other people were mingling. They had the best pizza in the world there, Lou Malnati’s* which made it easier for me to relax.

Every year, Power Pitch is run a little differently, a tradition which I hope continues. Here’s the rundown:

6 minute pitches

1 powerpoint

3 cash prizes ($3000, $2000, $1000)

When it was my turn, I walked up to the stage and waited for the cue to start. I had practiced this for a few weeks. I knew I had a pretty good shot since I was one of 3 businesses who actually had a working product at the time of the competition so I made sure to emphasize that. I also went through the classic business stuff: market size, how we make money, customer segments, etc. Thanks to the Powerpoint, explaining natural language processing was significantly easier with the visual aid for the audience.

The questions were pretty easy to answer except one (and it wasn’t even a technical question!) It was posed by none other than Troy Henikoff, Managing Director of Techstars:

How would bigger names/brands find this useful enough to pay you?

This was something I thought about, but not something I focused greatly on at the time. The question pertained to my business model. I mentioned how currently we had users and a stream of visitors but we would scale by offering natural language processing services to enterprises. I knew that they needed it, but I had yet to do the exact math on how much they would pay Tweetsense and what amount of money Tweetsense could make for them in return. So like many good presenters, I made something up real quick. Thankfully now we have the answer. The answer is that we are saving those brands upwards of hundreds of thousands of dollars in consulting fees from brick and mortar social media management consulting firms the same way Salesforce replaced god knows how many people in customer service. Note that at the time, we weren’t even thinking of doing this in the political space.

After my pitch I was able to sit down and listen attentively to the other pitches (they were pretty good). Soon the judges convened and deliberated for about 15 minutes while the audience got a chance to talk to the businesses. Then one of the judges walked up to the stage holding 3 giant checks. They were going to announce from 3rd to 2nd to 1st place. How should one feel at this moment? It’s a little confusing. On one hand you want your business to be called later to get the highest honor, but at the same time if it doesn’t get called on early, there’s the uncertainty that it didn’t win anything.

Third place,



Well what do you know? A thousand dollars! I’d call that a good night! (You can go to the original post linked at the bottom of this page to see the other competitors)

Little did I know that this victory would be the first of many and that as a founder I would need to achieve 10x more if I wanted Tweetsense to be more than a project. I had competed twice before but never even made it to the final eight. The reason? It had always been somebody else’s idea. Somebody else’s vision. Unfortunately for those times, that person/cofounder (while brilliant) just didn’t care enough to execute. This year was different. I competed with my project, actually developed something and gave it my all. I realized the difference between doing something for completion versus doing something for passion. In the world of founders, there is no 80%, no B+, nobody cares if you completed the powerpoint or not. Being a founder takes long term commitment and sacrifices that few can make and even fewer want to make.

After the ceremony we walked out of the Merchandise Mart and looked in awe at the city. It was surprisingly quiet, but then again it was a weekday. I had never seen this part of the city at night before so it was really a beautiful view. Other cities should take a page out of Chicago’s book if they ever want to do architecture right.

*To those of you who say New York has the best pizza. I’m sorry for your lack of good taste. It’s thin, weak and incapable of delivering the proper amount of flavor with its weak construction.

Photos from the event. Original post/source on website


Author Convey

More posts by Convey

Leave a Reply