Brendon Thomas on Building Wings From IT Manager to Entrepreneur – Episode 82

Today’s episode Phil and I get to talk to Brendon Thomas, our dear friend from Milwaukee, Wisconsin. We ran into a few technical blips so we have not included the video version of today’s episode. In the podcast, we were able to remove some of the dead space so today’s show is definitely worth the listen. Brendon takes us through the fear he felt after jumping out of a lucrative career in IT to startup his first software company.

We’ll find out what Brendon has been up to the last 3 years since leaving corporate to live his dream of doing meaningful work as a software entrepreneur. There was a lot of failure, a lot of grit, but a lot of success that followed.

Listen to the podcast

Share Some Shut Up Love –> I had jumped. There was no way of going back to the top of the cliff. – @ThatBrendon #shutupshow (click to tweet)

Fun Facts:

  • Brendon Thomas was recently named the President of Okanjo in December 2013.
  • Through the creative community in Milwaukee, Brendon found Berni and hired her as a business coach, which sparked his leap from a corporate IT management position in 2011 to becoming a serial entrepreneur.
  • Brendon spent most of the last 11 years helping build technology products that solve increasingly interesting problems, such as how to make buying and selling social again.
  • Brendon co-founded Soarce Technologies, worked in healthcare technology, was Founder and CEO of Shindig, and Chief Product Officer at Okanjo before taking on his current role.

Defining Shut Up Moment:

Berni and I first met in January 2011. During our first coaching conversation, I worked at a local healthcare company. I remember that day. I was 26 at the time, feeling on top of the world. I was the youngest IT manager at the company. I was on the phone with Berni at 5:30pm. It was dark out and I was sitting in my corner office. My thoughts were, I kind of got this but what’s missing? What am I not connecting here? By many definitions of success, I was on my way if not having arrived. But it didn’t seem as meaningful. It wasn’t what was going to ignite that spark in me. Through that conversation it became apparent I need to make a change, a big change. Let’s really chase what I’ve known has been something meaningful to me in the beginning.

Six months was my timeline to make this happen and it involved a software startup. I’ve got 10 years in healthcare technology. My initial thought was to go to the Valley or New York. So I started to look for consulting jobs in those areas to fund myself while I start this company. The next few months I did this and what I found was, there’s a very strong creative community right here in Milwaukee. People who really had that spark. So I took a consulting job to work locally to fund myself while building this company.

You would think this is my shut up moment because it led me to launch Shindig, my first company, in June 2011. During the four weeks between leaving one competitor for the other, I got to spend heads down time working on my project that was so meaningful to me, I decided I couldn’t work the consulting job. I thought if I don’t chase this opportunity, I’m going to regret this for the rest of my life.

Shut Up Tips:

My plan did not account for a period of not having income. The period of jumping off the cliff and not having anthing there to catch me. – Brendon

A scary moment is when you realize you have one week’s left of payroll and your investors aren’t able to continue keeping things afloat. – Brendon

Realize if you put yourself out there and the opportunity is right and you do the work, the net will appear. – Brendon

I knew I wouldn’t be able to duplicate that feeling of flow, that moment of creativity and productivity where you’re utilized to your maximum extent. – Brendon

I had jumped. There was no way of going back to the top of the cliff. – Brendon

One of my investors taught me, “What better way to spend what you have than a life experience that is going to set you up for success with the next one.” – Brendon

Most people have to learn by failing a dozen times and doing it rapidly. – Brendon

Keep things moving, keep the energy going. – Brendon

Brendon Recommends:

Okanjo Debuts Powerful Cloud Commerce Solutions (read more)

Find Brendon:

Twitter: @thatbrendon