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Pimpin’ Ain’t Easy

I am a pimp. Not in the traditional sense, but I am a pimp. The majority of my job is trying to pimp our company and games to anyone willing (or unwilling) to give the time of day by every possible means. Spending each day writing emails, posting on Twitter, Facebook & Instagram, making cold calls, participating in press calls, responding to forums… it never ends. As Big Daddy Kane wrote, “Pimpin’ Ain’t Easy”. His words especially ring true when it comes to startup contests where you strut yourself for a group of judges in hopes of being selected to sell your services.

We have just recently made the finals for a local startup contest and more than winning we want redemption. Less than a year ago we entered our first startup competition. It was sponsored by the Sacramento Kings with a cash prize for the winner. We had forgot what cash looked like and were excited, but entered with a low bar. Half stunned when we received our ‘you made the cut’ email we quickly transitioned from surprised to overconfident. The selection email explained how each company would deliver a 5 minute pitch to potential investors in a March Madness type of bracket with the final four delivering their final pitch at a Kings game. Piece of cake. We had never entered anything like it let alone created a 5 minute pitch, but that didn’t have any bearing on our blind optimism as we talked about how we should spend the prize money and what to wear to the Kings game.

Once we got started on our pitch optimism was replaced with frustration as our underlying issues quickly surfaced. Three of us started AppA11y and not until recently would I say we were all on the same page. This exercise, like most everything resulted in three people heading down three different paths. While we started working on our pitch together, we were soon each working on three separate “perfect” pitches. We tried to come to a consensus at the end, but the final product was every bit the dumpster fire you would expect.

And really, dumpster fire doesn’t do it justice. We were the only company who hit the five minute mark without completing their slide deck (we still had 6 slides) and due to our extended answers, the only company who didn’t allow enough time for each judge to ask their questions in the Q & A that followed. The first judge summed it up with their question/apology when they asked, “I am sorry, can you tell me what you do?” No prize money, no Kings game. It was a dumpster fire on a freight train that wrecked into a shit show.

So here we are nine months later ready to redeem ourselves in our second startup contest. Like the Kings contest we will have 5 minutes to pimp ourselves and then be scrutinized by those we hope will pick us up. Kind of feels like Tinder for startups. Our bruised egos have since healed and after going through process have a better understanding of how the game works. Investors want to know what you do and how you are going to make them money. Everything else is noise.

As painful as our first pitch was, it was the bump in the road we needed to confront and address our internal issues. We are a better company for it and am thankful for the opportunity even if we did throw-up on our shoes in a public forum. We are much more candid and to the point now. We are too busy to operate any other way and anything else feels disingenuous. If we fall on our faces (hopefully just figuratively), it won’t have the same sting as the first time. I am confident we are on the right track and if it doesn’t happen this time hopefully they will swipe right the next time.