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Becoming a Founder

I closed my law office after 8 years to found a startup. Why?

I had wanted to be self-employed for as long as I can remember. I was lucky to grow up believing that entrepreneurship was even a possible career path. Both my father and my grandfather were self-employed and I saw the benefits and learned that setbacks were inevitable, but temporary.

The United States is the richest country in the history of the world and capitalism seemed to have opportunities for anyone who wanted them. Truly, why would I ever want to work for someone else?

I decided to enroll in the accounting program of University of Orgeon's Lindquist College of Business, a top 100 ranked business school. I had two reasons. First, accounting is the language of business and I believed (correctly) that it would be a lifelong asset in whatever career I ultimately chose. Secondly, becoming a CPA was the most direct path to being a self-employed professional.

CPA candidates are required to practice a certain number of hours of before qualifying for a license. I did my time first at a regional firm that serviced closely-held companies, and then at a Big 4 firm where I worked with public companies and securities.

As a senior accountant, I was assigned to a different project every two weeks. My job was to thoroughly analyze the industry and the business operations of nearly a hundred companies. This included interviews with CEOs, CFOs, Controllers and Treasurers who oversaw hundreds of millions of dollars of revenue. This experience was invaluable.

I passed the CPA exam and was licensed in 2002. I started a solo practice shortly afterwards.

After a couple of years and careful consideration, however, I decided to enroll in law school. Strange as it seems, I minored in philosophy and yet was fascinated by tax law. It proved to be a natural extension of my accounting and philosophy background.

I graduated, passed the bar and started my law practice in 2010 with a laptop and $2,000 - enough to keep the lights on and pay next month's rent. By 2017, my revenues had grown to hundreds of thousands of dollars. I felt my practice was a success by any measure I could imagine.

However, I discovered that I had enjoyed building my law practice as a business as I much as I enjoyed practicing law. I was starting to think about something new.

I found an opportunity in Engage. I had struggled with tax preparation engagement letters as a persistent, annual pain point in my practice. Inspired to solve this problem, I designed a solution that automated the workflow. Other accountants wanted it and it seemed like the idea had commercial value.

This six-part series explains how I evaluated the concept, the market opportunity, and recruited a team to build the app. Its been three years and the company is growing. We are negotiating a handful of licensing agreements that will mostly take the company out of my hands, so I am moving on and re-starting my law practice.

My tenure with the company is coming to a close. It started several years ago when my co-founders and I agreed that whatever the result, there was no doubt we were going to learn something.

And I did. I learned how to be a founder.