Feeding My Inner Willy Wonka

I’m 43. In some startup circles the ageist mentality is prevalent and it’s unfathomable a guy my age can have the same passion and energy as a recent grad with a kick in his or her step, a fresh degree in hand and supreme confidence they are the next big thing. I mean, I didn’t graduate from an MBA program, I didn’t take entrepreneurial studies and in fact I attended five different colleges (Yes, five) and am still seven credits short of my undergraduate degree. Why would I want to do this to myself? Because I need to feed my inner Willy Wonka and we all have one (I need to clarify that I am speaking of the 1971 Gene Wilder version not the recent, creepy Johnny Depp effort).

First Go Around

This isn’t my first rodeo. In 2005 me and a business partner Ben Saren started a local search company, Citysquares, that we bootstrapped for almost two years before a fateful final month of “If we don’t get funding after these last round of pitches we will shelve it and get regular jobs”. Well, we did get funding on that last tour, which was exciting to say the least but it’s funny looking back at saying if we don’t get funding “We will get regular jobs” What is a regular job? Until I jumped into that startup I didn’t understand the difference. I finally realized it when I found myself standing in front of a whiteboard at 7am on a Sunday morning in my boxers because I slept on an air mattress in the office the night before. I slept in the office often and I found myself happy and enjoying the creative process that I owned — and my sincerest apologies to the Harrison Ave. cleaning lady who unfortunately saw more of me than anyone should ever have to. That was the difference. It was about the creative process where anything was possible and there were no wrong answers, just pivots, and most importantly it was your recipe with unfiltered ingredients. This line from Willy Wonka has always stayed with me.

Invention, my dear friends, is 93% perspiration, 6% electricity, 4% evaporation, and 2% butterscotch ripple.

Going To The Darkside — Learning Lessons

After the acquisition of Citysquares in 2011 I decided to jump into the “regular job” world. Why? Well, I can’t say in a simple way. I was tired but also not sure of what was really next. I ended up going to work at a large payment processing company. Having some 9–5 steadiness was new and interesting. I had to adapt to a different kind of work beast. While I met some great people along the way and had some good experiences, dealing with a big company mindset just wasn’t for me. I had lost my passion and working around other people that lack passion is a back breaker. The lessons were different from my startup days but were just as, if not more, valuable. I absolutely needed this experience to outline what I didn’t want in my work life. My top 10 takeaways for working at a large enterprise company were this.

  1. Certain people are wired for large established enterprise businesses and others are not.
  2. Change is difficult for these companies, even if it’s for the better, they won’t and don’t adapt.
  3. Too much money was budgeted and spent on below average solutions.
  4. Meetings were scheduled for meetings to understand the last meeting so another meeting could be scheduled about that meeting so we could have a lunch meeting.
  5. Everything took WAY too long and tech and innovation were WAY behind.
  6. For every passionate employee that wanted to innovate and execute there were three that did just enough to keep their jobs.
  7. Mediocrity hides in large company infrastructures — even at senior levels.
  8. Fear made it difficult for people be honest and speak their mind to management.
  9. If you didn’t conform you were expendable.
  10. I couldn’t work on a whiteboard in my boxers.

Big Enterprise company work life was not for me.

Going For A Second Helping

So it’s 2014 and I have my generous severance package (See #9 above) and truth be told my head was about ready to explode and I was ready to get back into the startup culture again anyway (See #10 above). I had lost my mojo and I needed to get it back. I realized a big part of me was missing without that passion, creativity and urgency. Being in an early stage startup is unlike any adrenaline I have ever experienced, even on a sports field. I needed that juice, that energy to create and build again. For the last year or so I have been working diligently on my new startup. It’s called Jokkspot and I couldn’t be happier — minus all the canned tuna dinners. Without getting into too much detail (Another time, another post) Jokkspot is a youth sports platform that does robust team and league management and allows crowdsourcing from fans and parents mobile devices at live events to create game streams. Youth sports is a $26 billion market (Just in team revenue from fees alone) that has a few solid players but is still wide open for grab. It’s what I feel is the wild, wild west of market opportunity. It’s been such an exciting time with finding a co-founder to prototyping and being in the process of building the platform and web & mobile application. I feel energized again and am back to working passionately and being creative. It’s where I need to be.

Why Wonka?

I imagine everyone has seen at least one version of the Willy Wonka movies (Please see the original if you haven’t). See, Willy Wonka is anything but conventional. His eccentricities make his creative pursuits almost so absurd that you could actually believe they are possible. You have to have the same mindset when in a startup. You have to ignore distractions, make hard decisions, work tirelessly and sometimes just make shit up as you go. There is so much noise out there that sometimes you have to lock yourself away to truly create something special. That’s not to say market research, competitive landscape and things like value props and business model canvases, etc. aren’t valuable or needed. They are 100%. It just means that sometimes you have to create without somebody telling you how to do it from a book or seminar. Do it the way you want to do it. The less noise, the more creative and absurd you can be. That’s where some of the more wonderful ideas, creations and solutions come from. We all have an inner Willy Wonka inside of us and I hope you feed yours.

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