(UPDATED 2020): Entrepreneurs are risk takers.

We often appear reckless. Fearless. Maybe even crazy!

One of my favorite quotes of all time is Steve Jobs’ talking about the crazy ones:

“The people who are crazy enough to think they can change the world are the ones who do.” — Steve Jobs.

So YES, it takes a special breed to be an entrepreneur. That is a fact.

However, many people really don’t really understand how smart entrepreneurs take risks. It might not be what you think.

Let me be clear. Smart entrepreneurs don’t put on a blindfold and jump off a cliff, even if it looks that way (and sure, it often looks crazy).

But what you don’t see is what really matters… and that is that the entrepreneur going off the cliff is wearing a parachute and has on spring loaded shoes. They might have a trampoline or huge net just out of view of the camera. They have mitigated most of the risk so that what looks crazy, isn’t really that crazy after all. They are doing something others won’t do, but that’s because they fully understand the risk – and have reduced most of it out of the equation.

This is certainly true from me. I have often characterized my career as “sprinting into the fog,” but that may unfairly represent my full approach.

A better way to describe it is likely that I am comfortable sprinting through fog BECAUSE I have studied the landscape, reviewed the maps, measured and calculated. I’ve talked to others who have been where I want to go. I’ve gotten advice. I’ve done test runs. Then, yes, I sprint right into the fog… into an area others aren’t or weren’t willing to go.

If you are reading this and thinking, “What the heck is Mac talking about?”, let me be clear.

– Smart entrepreneurs actively mitigate risk.

You have to consider alternative outcomes.  You need to have contingency plans and backup plans. If Plan A doesn’t work, you move to Plan B. So before you even start you need to have Plans A through at least D…

How do you mitigate risk?

  • You plan.
  • You do market research.
  • You stress test your assumptions.
  • You run countless scenarios.
  • You get support from mentors.
  • You get beta customers before you go to market.
  • You triple check and make sure you are ready.

Now this ^^ doesn’t mean you move slow or waste time. But it does mean you do your deep work to actively mitigate risk.

Then when it is time to go… you GO!

Jump in and don’t look back. Sprint into the haze and the fog.

Don’t keep your resume updated or your tie hanging on the doorknob.

If your heart says go, your gut says go (and you did all your homework), you give it 110%.

So, remember, great entrepreneurs take risks. They look fearless and crazy BUT smart entrepreneurs look that way because they’ve done the work. While the rest of the world was distracted or sleeping they studied so now they can put on their blindfolds, and jump.

Here’s to the “not so” crazy ones.


Here is a great by Malcolm Gladwell on the subject…

The Sure Thing (Malcolm Gladwell)


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