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Hard Truths: Why I Quit 7 years of Launching Profitable Businesses and Got a Job at Amazon [Hint: It's not about $]

15 months ago I quit 7 years of launching profitable businesses and got a job at Amazon. 

This was despite selling my B2B SaaS business and marketing agency with enough cash to live years without an income (and I have two kids to support). It would have been easy for me to start another business, but my heart wasn’t in it.

Over 7 years of entrepreneurship I went from being too scared to pick up the phone and talk to prospects to becoming a builder who could sell [you can read my gut-wrenching 1st year story here]. 

In my first year of business I lost about $40,000 in my best year the company did over $1M in sales. To many people I was “free” from the 9 to 5. I had divorced my income from my time. I could work as little as 2 hours day and earn a six-figure salary. 

At the beginning it was great. I cooked better food, worked out, traveled, took language classes and read widely. But something surprising happened... 

After a few years of “freedom”, something struck me. Freedom turned out to be little more than optionality. The question quickly became what do I do with my freedom? 

For me the answer was clear. I wanted to take care of my children and give them opportunities I never had. I wanted to continue to enjoy my marriage. I wanted to take care of my health and I wanted to have a career where I could build and sell with autonomy. 

This stuff was more important than “keeping my options open”. 

So I traded some of my freedom for something more important; commitment. 

For me freedom is a means to an end. If you know the “end”, then skip to it. Commit. Take the good with the bad. No need to start a profitable business, unless you consider it "play".

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Manning the booth at an industry conference and selling my B2B software.