The Five Most Dangerous Things You Can Do As An Entrepreneur

The Five Most Dangerous Things You Can Do As An Entrepreneur

From taking that first step, to the complacency of success, these are the lethal challenges every successful entrepreneur will face.

If I’ve learned anything in my short time one Earth it’s that there is no success without taking risk–even if it’s only taking on the perception of risk. That’s exactly what stops most people; the sense that standing still is safer than moving forward. We end up stuck on the shoreline as we wait for some untold future to arrive with a nicely wrapped package called “opportunity.”

No, it doesn’t work that way.

I was reminded of that as I stood on a beach this weekend looking at rip current warnings and listening to an old Semisonic tune on my iPhone. (Don’t worry, I’ll bring it full circle by the time were done.) It struck me that as an entrepreneur you need to accept that there are periods during which you will be swimming against a current that is nearly impossible to overcome. And just like the real thing you have only two choices; swim parallel to the shoreline, get out of the current and back to the safety of the shore, or swim with it out into a sometimes terrifying future.

I’m not going to judge the choice anyone makes. This is your life. But what I will share with you is that if you do decide to go with the current there are five mistakes that will just about insure you’ll never make it to any coastline.

    1. Don’t Take The Plunge– This is the single most terrifying moment in the life of a soon to be entrepreneur. It’s that moment just before deciding which way to go; do I head for the safety of where I’ve been or venture into the unknown. It comes with all sorts of unanswered questions; how will I pay the bills, will I have a safety net if it doesn’t work, is it the time right? All good questions, but here’s the rub, there are rarely definitive answers. The better question is, “Can I live with myself if I don’t do this?” What I can tell you, from my own experience and that of others I’ve talked to, is that most of what you fear is taking that first step. Trust me, once you’ve made that commitment the process of swimming like hell takes over and you don’t look back.

      “The better question is, ‘Can I live with myself if I don’t do this?'”



  • Don’t Question The Plan– Once you’ve taken The Plunge you’re in execution mode. The problem is that people often get so wrapped up in succeeding with The Plan that they miss the really big opportunity. My first company had been planned out with extraordinary detail. My partner and I were convinced it was bulletproof. But after working 20-hour days for a year it finally dawned on me that the real opportunity was not at all what we had expected. Had we both not been open to throwing out the first plan we never would have caught the current that allowed us to build an Inc 500 company.



  • Don’t Build The People– So you’re well on your way and you can see the vision evolving. It’s real and it’s achievable. The question now is, How do you capitalize on it? This is where so many entrepreneurs miss the chance to transform vision into value by focusing too much on themselves rather than on building a team of the best people. Yes, you’ll be working harder than ever but your team is everything at this stage. Turn your focus towards them. Find people who are not clones of you but who instead balance and supplement your deficiencies. Having shared values and commitment is key, but so is having a broad spectrum of skills that can be quickly reconfigured to address changing market needs and support a growing organization.



  • Don’t Change The Potential– It may seem odd that I’d put Potential towards the tail end of this lisy (perhaps I just ran out of “P” words..) after all you already have potential, that’s how you got this far, right? Yes, but the potential of your organization will change over time. What you once thought of as its potential and scale may one day become limits to growth rather than targets. Organizations, like people, need to have the bar raised in a very conscious manner in order to achieve more. I recall having to convince one of my sales people that they really could sell $3 million dollars worth of services, rather than just $500,000. They had been with me from almost the outset and just didn’t believe it was possible. They were right, it wasn’t possible–past tense. They were stuck in a potential that we had outgrown, and they needed to outgrow it as well!



  • Don’t let Go Of The Past– At some point you will need to lose sight of the shoreline; forget that it ever existed. You are creating a new reality that undoubtedly could never have fit into the confines of the past–for you, your team, or your marketplace. When you truly arrive at that place it’s very sweet because now you’re the one creating the rip current that others have to swim against. And, ironically, this may be the ultimate challenge, that of complacency. Nothing has devoured more successes than the sanctimonious feeling that we have arrived, when in fact all you’ve done is built a new shoreline from which your next biggest competitor is already contemplating the plunge!


So, ready to take the plunge? As the song says, “every new beginning comes from some other beginning’s end.” (Yes, that was the Semisonic reference…and, no, I didn’t go swimming. This time I took a boat.)

Tom Koulopoulos is the author of ten books and founder of the Delphi Group, a 25-year-old Boston-based think tank and a past Inc 500 company, which focuses on innovation and the future of business. He is also an adjunct professor at the Boston University Graduate School of Management, an Executive in Residence at Bentley University, the past Executive Director of the Babson College Center for Business Innovation, and a frequent keynote speaker. The late Peter Drucker once said of his writing, that it challenges not only the way you run your business but the way you run yourself. Tom’s latest book is The Gen Z Effect: The Six Forces Shaping The Future of Business.This post was originally published on

The opinions expressed herein or statements made in the above column are solely those of the author and do not necessarily reflect the views of WTN Media LLC.