Long Odds, High Hopes, and “Crazy Ones”

One week ago yesterday the scariest decision I have made in a short life full of bold and brazen life-changing decisions was officially final.

My Co-founder Holden and I had moved across the country from Louisiana to Santa Monica. We officially had no “normal” jobs. We are now employees of a company that had been created less than a month ago. But being one of the “Crazy Ones” is something I always knew I was, even from an early age.

Most of my childhood was spent listening to my Dad talk about the business he wanted to start. He had an idea, he had the means, heck he even had a name (KBZ Enterprises – The initials of his children in order of age, I’m the youngest of the three so it stood for Karlie, Ben and Zach).

But the one thing I didn’t watch was my Dad actually starting that business. #

By the time I left high school I knew that starting a business was nothing my future children would ever hear me talk about in a wishful sense. I started my first LLC before I had even gotten out of high school. I had literally no idea what I was doing and it was the most fun I had ever had.

I had been selling golf clubs on online forums and ebay since I was a Freshman or Sophomore in high school and by the time my Senior year rolled around I guess you could say it was a “profitable endeavor”.

I sourced clubs from some of the world’s largest golf club manufacturers during the day and spent my nights chatting with providers in Japan trying to bring over quality brands that had not yet reached the US markets.

I didn’t know what the hell I was doing – but I knew I wanted to do it forever. #

As time passed golf clubs got boring for me and I decided to try my hand at a different craft. I’d had a computer since childhood, written my first flashcard games with a book on C that my grandfather had given me and had only begun to realize what computers could do.

The next few years would change my life for good. What started as a copy service making physical copies of paper morphed into a service scanning thousands of pages(and eventually millions) and making those documents instantly searchable. The system was a set of Sharepoint plugins which used indexed OCR data to truly find the data instantly, even though this wasn’t magic it sure seemed like it to our customers.

Even though this wasn’t magic it sure seemed like it to our customers. #

That company eventually sold and I ended up getting to take some time and do some important things, I spent some time working with my Dad on the company he FINALLY started.

I met my co-founder Holden. She also happens to be my girlfriend and life-long co-founder if I have my way. ;)

I was able to work for a company which was eventually sold to Groupon and was fortunate enough to be accepted into a Y Combinator with another company I helped found.

All of this means that at 26 I have been a lot of things.

Lucky. Overworked. Tired. Excited. Happy. Sad #

Last Monday was different. It was the beginning of what I hope I can look back on one day and call my life’s work. We’re building a tool that can save our users hundreds of hours over their lifetime and give them the freedom to make the best decision for their finances once and for all.

More importantly we’re building something that should change our users’ lives for the better. Last Monday was a big day, but I have a feeling the biggest are yet to come.

Because while the odds are long, the hopes are high.

As for Holden and I… well, we are two of the “Crazy Ones”.

If you have read this far, you should follow me on Twitter.

More importantly if you hate paying bills and want some of your valuable time back you should definitely sign up for our beta at Cloudbill.


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