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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Entrepreneur Cheerleaders

EasyReally this is about entrepreneur cheerleaders and success cheerleaders, people who sell hope and, this is the important part, make it sound easy. I’m a realist and nothing worth getting is easy. It might be enjoyable but it’s not easy. These cheerleaders remind me of the Geico commercial with Pinocchio as a motivational speaker, as he points to people he says have potential, his nose grows. Not everyone is going to be a wild success, not everyone can run a successful business. If a cheerleader like Anthony Robbins was Pinocchio his nose could hurt someone.

I’m not saying that having confidence is a bad thing or that being positive is a waste of time, I’m not telling you success isn’t worth working toward. I’m an advocate for curiosity, for adventure, for pushing yourself to your limits in order to discover what you’re good at, to find what excites you. Do all of those things but understand what you’re getting into, what you’ll likely face. I saw a tweet yesterday that is appropriate here:


Successful people are very good at managing risk, at understanding the odds and finding ways to tilt the odds in their favor.

You might think you’re good at that too and that’s where self-awareness comes into play. The cheerleaders out there will tell you you’re great, that everything will work out if you just believe but that’s not necessarily true. Belief only gets you so far.

This is why I’m a big fan of Gary Vaynerchuk, he puts a lot of value on self awareness, he’s not a cheerleader in the sense that he’s honest with himself and has no problem being honest with his advice.

Listen to the cheerleaders for inspiration, get fired up, but then get real. Look at your What Next from every angle and anticipate as many problems from the start. Be an optimist in the dream phase and a pessimist in the implementation phase.

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The Right Answers

We all have the right answers but do we have the right actions to use those answers?

I spoke at a Youth Leadership Summit last week and in my presentation I held up very successful people as examples and asked the attendees what traits led to these people’s wild success at various stages of their career.

The answers were all correct with terms like perseverance, creativity, passion, and motivation. I added a few such as curiosity, flexibility and a sense of adventure.

GarfieldLazyThe point is that we all know what it takes for others to achieve big things but we’re often afraid to do those things ourselves. Worse than being afraid we’re often lazy.

I don’t mean lazy like we sit on a couch watching TV, eating chips rather than working (everyone at the summit had a career and took the additional step of attending the summit). I mean lazy in comparison to the examples I held out, people like Richard Branson, Ted Turner, Gary Vaynerchuk and many more who have enough energy and drive to keep them moving toward success.

I don’t have nearly as much energy as the previous examples and yet I work a full time job (which I have progressed in over the years), own rental properties, own and operate a retail service business, write books, and blog. I want to do more but I have to work my way up to it. Just as running a marathon takes conditioning, so too does the marathon of success take conditioning. How many of us are willing to do the work to build that base of conditioning?

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Gary Vaynerchuk Knows Himself Well

It’s no secret that I believe strongly that curiosity is essential for success. If you read this blog or read my book, you’ll find curiosity hailed throughout. You will also find that I speak of other traits that amplify curiosity and lift ordinary success to higher levels. Those traits are a sense of adventure, willingness to try things, a healthy understanding of risk, and self-confidence, to name the ones I think are most important.

Gary_1In my interview with Gary Vaynerchuk he added one trait to this list that is often needed to balance out the others, that trait is self-awareness. You have to be a good judge of your own strengths and weaknesses and that requires self reflection. Listen to the conversation about self-awareness here:

 Vaynerchuk SelfAwareness

In my book, What Next, I interviewed an entrepreneur, Scott Loughmiller, who, when I thanked him for answering the questions so thoroughly said, “That’s ok I like this self-reflective kind of stuff.” That’s why he’s successful, because he is able to take stock of his own abilities and concentrate on the things he’s good at while hiring the people to do the things he’s not.

Loughmiller was trained as a programmer, a coder, but he doesn’t code much any more because he has the bigger picture to worry about. He knows there are people who are better at coding and can devote all their energy to it so that he doesn’t have to spread himself too thin and micromanage the project.

Gary said something that I suppose would sound ridiculous to a normal person. He said there was a time that he thought he should win an Emmy, Tony, Grammy, and Academy Award, really believed that he had it in him to do it. That made sense to me because I’ve had those grandiose ideas myself (In What Next I call them delusions of grandeur). It was self-awareness that brought Gary back to reality.

Do you take the time to think about your strengths and weaknesses? Do you understand yourself more than anyone else? If not, why not? Please share your thoughts in the comments below.

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Lessons from Juggling

Juggling BallsIn my last post on juggling life I asked you to watch a video that was at the bottom of the text and apply what Michael Moschen was saying to life, not physical things. In this post I’ll do it for you, give you my perspective on his talk. I understand we’re all busy and watching a 38 minute video might not be possible or practical.

The first lesson Mr. Moschen gives is knowing where the ball is in time and space, being aware. Where are you in time and space? Have you achieved the things you want when you wanted them? Too many people don’t know, don’t keep track of their progress, of their goals. Too many people are not aware.

The next step, once you know where you are in time and space, is adding complexity. But notice that he only added the complexity of vertical movement, he didn’t add several items, he added one! How many of us add complexity before knowing where we are in time and space? How many of us add several layers of complexity at one time? Too often, I think, having children comes first then we figure out how to make ends meet. Too often people start businesses and quit their job before they figure out how to make a profit.

Third was balance illustrated by a broom perched on his chin, forehead, and even his ear. Balance is making sure you’re the center. If the broom begins to list left, move left, to center yourself under it. As you begin to learn balance the movements are dramatic but the better you get the more still you become, the more you realize the power in small adjustments. Are you making small adjustments in life or are you waiting until the broom has almost fallen over?

The last items, not mentioned by name but clearly evident, were curiosity and experimentation. These are themes I talk a lot about in What Next, the book, and in this blog. Curiosity and experimentation is what leads to discovery. Seeing things in a different way is what inspires Michael Moschen to put movement to inanimate objects creating stunning visuals. Most of us look at the same things, in the same ways but the few who can look at the same things in different ways or who find new things are the most successful.

Here’s a similar type of juggling that I just had to share – and it’s much shorter than 38 minutes!

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You Have More Than You Think

You have more time, money, knowledge, stamina, desire, influence and ability than you know. Those that recognize this fact are more likely to succeed.

You have the power!When faced with an impossible task you either rise to the occasion or you don’t. I think of the rare stories of people being lost at sea or while hiking, people who have survived difficulties none of us prepare for. These people found stamina they never would have imagined they had sitting in the comfort of their homes which means you have much more than you think as well.

There are everyday situations that require extraordinary commitment and focus, that many people either don’t have (I don’t believe that) or aren’t willing to put forth (all too common).

I’ve always considered myself entrepreneurial but I’ve been that way on my terms, meaning I’ve been somewhat conservative. My latest project has me taking on moreCash risk financially than I ever have and while it is daunting, I’m having the best time I’ve had in a long while. The joy I have from working harder than ever before comes from my confidence, I believe I’ll do well, and my sense of adventure, I want to explore my abilities and discover new strengths. These things, confidence and adventure, often lead to flow, a mental state in which a person in an activity is fully immersed in a feeling of energized focus and full involvement. In flow, times flies and before you know it, hours have passed.

So many people complain that they need more of something, more time or money but it’s there if they only look more carefully. You would be amazed how much money you could find if you just figure out where you’re spending it or prioritize things and give up the less important expenses that cost money but give you little benefit. You can find more desire by really exploring what it is you want to do, what you love to do, what excites you.

When we began our latest business journey, Julie was rightfully concerned that with our already busy schedules, we wouldn’t have enough time for this project, and that if we found the time, then we wouldn’t have enough time for each other. So far, I’m happy to report, we’ve found the time to devote to this adventure and, since we’re doing it together, we still have each other’s company – a win-win! But time is only one aspect and we’ve seen that we need more than we thought when it comes to money, knowledge (I’ve done more research for this than I ever did in college), and patience.

We need more of everything but it’s there if we’re willing to do what it takes to get it. In the case of money, maybe we have to give up somethings for the more important stuff and so we reduce discretionary things like cable tv or stop one type of investment in favor of another (which is what we’ve done).

As for time, this blog has suffered. I haven’t been writing new posts in a while but something has to give. As we move forward with this project I’ll blog more about it but that will happen when I’m finally ready to reveal this latest What Next. Stay tuned and check back here often (and explore – there are lots of posts with lots of good information if I do say so myself).

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Creativity Begets Creativity


Creativity begets creativity. If you want to be more creative then hang out with creative people, or read about them, or watch them on TV. If you want to be creative find a way to experience other people’s creativity.

I’ve seen a few tweets about something called World Creativity and Innovation Week. I’m too busy to look up what that is because I’m exploring how it can help me. A friend tweeted this:

Creativity Tweet

Curious exploration

Being a curious person I clicked the link and then clicked the second story in the list which took me to a post by Mike Brown. In his post Mr. Brown told a story about seeing a poster called Peter’s Laws which he modified and turned into questions to spark creativity.Peter's Laws

Again being curious I wondered what the origin of Peter’s Laws was. A Google search later I had my answer with this webpage. Peter Diamandis is the founder and chairman of the X PRIZE Foundation which is most famous for their $10,000,000 Ansari X PRIZE for private space flight which Burt Rutan won.

Back to Peter’s Laws

A couple of the laws caught my eye because they fit so nicely with the concepts in What Next.

One law reads “When given a choice…take both!!” and that is an essential part of asking What Wext. You can walk multiple paths in life – we all do it as spouses, parents, employees, business people, and friends. What successful people do is excel on multiple paths and that takes dedication and work. If you aren’t dedicated and/or aren’t willing to work, then you won’t succeed.

The Peter’s Law that immediately follows the one above is “Multiple projects lead to multiple successes” and again we have the key point of What Next. The do one thing well concept is just as wrong as the jack of all trades master of none concept. Who says you can’t do lots of things really well or at least hire people who can?

Back to Creativity

I wasn’t sure what I was going to write my next blog post about but reading Mike Brown’s post and being curious enough to do a little research sparked my creativity and led me to write this, proving that creativity begets creativity. The same can be said about the other traits of What Next: curiosity begets curiosity, adventure begets adventure, action begets action, and success begets success. If you want any of those things then get to know people who exhibit those traits and start spending time with them.

As another of Peter’s Laws states “When faced without a challenge, make one” this is your challenge, to succeed, so what are you going to do about it?

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Navigating the Wilderness


Whoever says they have the answer isn’t thinking big enough. THE answer implies there is only one way, one answer. There are more options than you can imagine to every question. This idea is why I hate books with titles like “The Eight Steps to…” or “The Six Secrets of…” Some people may need nine steps to complete what you do in eight, someone else could do it in seven easier steps. How does that make you look Mr. Eight Steps?

The idea of secrets is just stupid. There are no secrets. Everything can be discovered, nothing is being guarded, protected like a secret would be, it just may not be out in the open. I often say “discovery comes when you look in places not easily seen” not because there’s some secret out there but because digging around, exploring, is how you learn, how you uncover answers.

I keep coming back to this one trait that successful people share because I think it’s the most important; curiosity. I also come back to curiosity because I believe this is the one trait that is the easiest to develop. Can success be taught? No, but the traits that successful people share can be, leaving the rest up to you.

Try to learn something new every day, discover a new website, research an historic figure, take the long way home. If there’s a problem you’re dealing with write down as many possible solutions as you can and then investigate which one would work best. There are so many options that no one person can claim to have THE answer. You’ll find the answer that works best for you through curiosity and discovery.

I often feel lost in a wilderness of knowledge that I can’t access. When I realize that I just have to spend a little time and energy looking for the solution, I find it. It’s like when I hike in the actual wilderness, usually in the desert, and take the route that most interests me. Sometimes that’s high on a ridge and other times it’s in a valley, but each offers a unique perspective and that’s all I need sometimes, a different perspective.

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Be the Trail Guide


Whether you are beginning your working life or are looking for a change, you have more choices than you realize. Choice is not an either-or proposition, however. You can decide to go to work for an established company, a big corporation, or you could set your own path, be your own boss. You could also do both if you want to.

Not too long ago I went to an event at a bar in NY organized by Andrew Warner of The event was a mixer (of course) where entrepreneurs and aspiring entrepreneurs got a chance to talk and share ideas. I met a guy who just recently (six months ago) joined the workforce after graduating college. The thing that was interesting, though, is that he was already anxious for more. He was looking for his what next. The experience he was getting was valuable but he wanted to create something. There is no reason he can’t do both, continue getting great experience while creating something new.

Being at the event was a step in the right direction but to be an entrepreneur, he also needs to be a leader. He needs to be able to get others to follow him, to believe in his mission as much or more than he does himself.

He is like a hiker setting off on a trail others have been down before. Anyone can be a hiker but a leader is a trail guide who knows their way. In this case, only the entrepreneur with the idea, the sense of direction, can lead their team of hikers.

Entering a palm oasis

Leading the way.

Is it enough to simply declare yourself a leader, the trail guide? No. You have to demonstrate why you should lead, you have to give as much as you get. The authority is not yours to claim but is earned as your enthusiasm and belief in the project lights the fire of those you want to lead to success.

Now get out there and explore the trail so you can be an effective guide.

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The Q*bert Way of Life

The internet is built for curiosity, for following different paths and discovering new things. It’s called surfing the internet because you ride a wave of information that takes you in different directions. If a page you’re looking at has links to something else you might click them and the new page probably has links of its own and you might click them too. By the time you’re done you may have ventured far from where you began.  But what did we do before the internet?

Successful people have always viewed the world like an internet of tangible items. Successful people hyper-link through life because they want to understand, to learn how things work. My recent post about Leonardo da Vinci is a perfect example of that kind of thinking. Da Vinci’s notebook reveals that he wanted to learn about proportion, how the sun is measured, understand hydrolics, and draw Milan, among other things. Who knows what sparked those interests but he pursued them just as today we simply click a new link.


Remember the game Q*bert? The goal was to hop from square to square on a pyramid, changing all blocks to the same color. That’s how curious people approach learning, hopping from interest to interest. Unlike Q*bert, however, we can linger on something that really interests us.

When I read a book or magazine article, whether online or in print, anything that interests me becomes a link I can “click” on by doing my own research. If I’m driving and see some web site posted on a car (and I can’t figure out what it is on my own) I’ll check it out. It might be cool, it might be dumb, but it’s worth the two seconds it takes to find out.

OK, so here’s how the Q*bert theory of curiosity works for me. A person I follow on Twitter tweeted a link to an article on I clicked it and read it, but didn’t think it was that good. There were several links in the article, though and I clicked on two of them. One was for Academic Earth where you can watch videos of very smart people saying really useful stuff. I clicked on one video but didn’t like it much so I went back to poking around. Then I found another video and this one was great. It was from 2007 but who cares as long as I found something relevant in it. Now I’m going to tweet a link to this video and who knows who will watch it next. Then I turned my attention to the other link from the article and I spent about 20 minutes watching videos about probability. That is the definition of curiosity and the difference between me and someone else is that I clicked and others don’t.

So how many links in this post did you click on before reading this sentence? Be honest and let me know by adding a comment below.

Be curious!

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