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I’m a Dying Entrepreneur
How successful entrepreneurs fail

2016 was a banner year for me as an entrepreneur/venture investor, and 2017 is looking to be as good, if not better. Naturally, with success comes a hectic schedule. I’ve been away from home five of the last eight weeks and can’t count how many cities across the continent I’ve traveled to this year. I’m in an insanely busy time for work, and life in general (I have two young boys at home ages 1 and 4). Certainly not complaining, one must make hay while the sun shines after all, but I’ve discovered a chink in my entrepreneurial armor. Let me explain…


Why Successful Entrepreneurs Fail

Getting to my record year as an entrepreneur in 2016 began with my 2014 New Year’s goals. I made plans to transform my online marketing business into a more wide-reaching publication; shifted my personal startup investing strategy from a commodity focus to tech, and I was on the verge of starting a very innovative and disruptive technology company (I intended to complete its structuring and initial funding requirements within the calendar year). The theme I gave the year was “make don’t take.” This was intended to keep me focused on building, not reaping profits. If I built what was intended, the money would take care of itself…

It was a one-year plan, but by spring 2014 it became apparent this strategy would not bear fruit until at least mid-2015, if not later. And it needed linear goal completion, one step to the next or none of it would work.

I carefully monitored the growth in all businesses on a weekly basis and put in actionable metrics – progress was my obsession. Every month each business was tweaked to continually improve on the growth rate so to hit my lofty ambitions at the end.

Just to keep my receding hairline moving in the wrong direction, by the start of 2016 the market had completely tanked, and my 2014 mission still hadn’t proven a lucrative one. But at that point, I was pot committed and wasn’t backing down. By spring 2016, thankfully, the market turned bullish, very bullish, and all my hard work over the prior two and a bit years began paying off. Frankly, it turned into a tidal wave of success; and it led to my banner year in 2016…

The planned seed funding round for our tech company in 2014 was wrapped up in early 2015. A $30,000 investment in our company at that time is, as of Friday, worth approximately $1.2 million…

The problem now is, I, and this is no excuse, have become so busy from the seeds planted in 2014 that I now have no definitive plans relating to NEW opportunities. I’m so busy in ‘management-mode’ because of this success that I haven’t maintained the fundamentals behind starting new ventures which got me into this position of strength in the first place.

As an entrepreneur/investor, we must constantly be looking for new opportunities. They’re all around us. Unfortunately, success has a way of blinding us. When wrapped up in our latest win, we’re susceptible to missing great opportunities. Consistently missing opportunities is how entrepreneurs die. The renowned self-improvement author Robin Sharma once wrote, “nothing fails like success.”

I don’t think this phase I’m going through is unique. In fact, I’ve seen it many times from other entrepreneurs awash in success. Thankfully, I have good friends and a wife to keep me on track, forcing me to be introspective. Writing you guys helps with that too. Can’t forget what got me here.

I’m dubbing this the “success trap.” For me, thankfully, the solution is simple: Hire more great people. And that is now my latest entrepreneurial goal. Many hands make light work… I want to hire three more people to help me delegate, spend more time opportunity spotting and taking meetings with startups, as well as focus on ‘visionary’ ideas – my passion. I need that creative time, every day.

As entrepreneurs, we sell great products, close lucrative deals, grow our customer base, not for what we’ve done today, or last week, or even last month. It often starts with the foundation we laid years prior. So, to continually grow and keep the momentum rolling, we must always be laying new foundations. Innovate or die.

Stay hungry,


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