In 2004 I got the chance to move to California to work as a caddy at the world famous Pebble Beach golf resort. The next two years were some of the best of my life as I got to work in a job that didn’t feel like work at all. The money was good, the clientele was amazing (sometimes famous) and it certainly didn’t hurt that this was my view every day when I went to work:

You don’t have to be a golfer to appreciate that.

What’s more, during my time at Pebble I learned a lot about who I am. I had spent the previous few years learning what I didn’t want to do – crossing things off the list so to speak. But this was the first time I started to see what it was that I wanted to do with my life.

I found that I really enjoyed the role that a caddy played with their golfer. It was this perfect combination of expert, adviser, coach, cheerleader and friend. They knew I was on their side, sharing their goals of playing their best golf that day and having tons of fun doing it. When my time there drew to an end, I began looking for ways i could find a similar type of working relationship with people in the “real world.” Since I already had an interest in personal finance (I had been reading books like Rich Dad Poor Dad and The Richest Man in Babylon and applying the principles found within) I decided to look at careers that involved working with people and their money.

I started out in the Mortgage biz, but as a brand new loan officer in 2006 with no clients and no clue, that was destined to fail. After working a normal job for a few years I decided to venture out again, this time in the area of insurance and financial planning. I moved through various aspects of each, from Life Insurance to Property and Casualty, then on to an all inclusive company that offered insurance and retirement planning. I even mixed a little training in tax preparation in there. Ultimately, I found that I kept getting burned out but I couldn’t figure out why. I believed in everything I was doing – people need all this stuff – but something kept me from committing fully to any of them.

It wasn’t until I left the industry entirely to help a friend build a tech company that I realized what the problem had been. In each area – mortgage, insurance, investing, tax prep – I had to sell a product in order to get paid. Like I said, I believed in everything I was selling, but I found that people needed something more than just an insurance policy or a retirement account to really address their financial concerns. What they needed was a better understanding of what was really happening with their money, and tools to help them conquer it.

And so, after more than 10 years seeing the struggle from multiple angles, I decided to take all of my experience and combine it into one basic service that would address the fundamental need many people have – how do I make my money make sense?

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