Gamblers Who Don’t Gamble

Entrepreneurs are gamblers who don’t gamble and risk takers who aren’t risky.

Sparked by curiosity, entrepreneurs explore farther and wider than most people but they aren’t reckless (at least not the successful ones).

RouletteNothing happens without ideas, and curiosity is what leads to the best ideas. You have to go through a lot of ideas before you find that magical one that both excites you and works. That search can sometimes take a lifetime and the search is what many people don’t understand about entrepreneurs. In my interview with Gary Vaynerchuk he said he has ideas “24/7.” But he doesn’t blindly follow all of them or most of them or even some of them. He said that if the idea sticks around for a while, just won’t leave his mind, then he’ll follow it.

Which takes me to the idea of risk. Acting on any new idea has risk associated with it but there is a difference between being risky and taking a risk. Being risky is doing something without much thought or planning. Taking a risk is researching, learning as much as you can, turning the unknown into the known so that surprises are minimal, and then going for it. One approach is dangerous the other is smart.

A lot of people confuse this penchant for risk as gambling but gambling is a loser’s game, gambling is a game of chance and successful entrepreneurs work hard to reduce chance. You can’t eliminate chance but there comes a tipping point when risk has been reduced to the point that action makes sense. This is why I put the following quote in my book: “I have always found that if I move with seventy five per cent or more of the facts that I usually never regret it. It’s the guys who wait to have everything perfect that drive you crazy.” That was Lee Iococca, the former CEO of Chrysler and that is the difference between someone who sees entrepreneurship as risky, as gambling, and someone who understands risk and works to make it less risky.

The person who has to wait until all risk is eliminated will never be an entrepreneur, and the person who rushes in without thought or preparation won’t be successful, but the balance between these two extremes puts the odds in your favor. It’s why I ask What Next and why I work hard to answer that with facts.

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Is Gary Vaynerchuk a Risk Taker?

After a short break I’m back to my interview with Gary Vaynerchuk. There was one question I asked Gary that I wish I had followed up on more extensively, explained a little better and really discussed. With limited time, however, I chose to move on.

Warning! Risk AheadI asked Gary if he felt there was a difference between taking a risk and doing something risky. He didn’t see the distinction. It is subtle but it’s there. At just under 90 seconds this is the shortest clip from the interview but perhaps my favorite topic. Take a listen here:

Vaynerchuk Risk

Gary notes that he thinks someone who takes risks is dramatically happier but goes on to say that he doesn’t consider himself a risk taker. I have found that many highly successful people who other people describe as risk takers or gamblers disagree with that characterization.

In my book, What Next, I talk about risk and what I discovered is that the distinction between taking a risk and doing something risky comes down to management. Scott Loughmiller, an entrepreneur I interviewed for the book, said he doesn’t consider himself a risk taker but rather a risk manager.

When we look at the decisions of the highly successful we only see two points in time. The decision to act and the end result. What we don’t see from our perspective is the thought process, the many sub-decisions, the careful deliberations and strategizing that goes into what seems like a risky endeavor.

And that brings us to the difference between success and failure when it comes to risk. So many people don’t take the time for careful deliberation. So many people rush into really big decisions ill-prepared. That is doing something risky. On a personal level you need look no further than retirement planning. So many people put that on autopilot without enough thought.

When it comes to business, too many people put too much weight on the advice to follow their heart. That’s good advice but it must be backed up by resources, planning, and a strong dose of reality. Doing the research, exploring the many possible outcomes before acting is taking a risk but it’s not being risky and that is a huge difference.

Are you a risk taker or do you do risky things? Share some examples and your thoughts in the comments below.

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