Back to insights
Do You Have the Characteristics of a Winner?
What makes Lionel Messi the best in the world

I’ve met some serious ‘winners’ in my life – special people. From billionaires to Lionel Messi, an incredibly tough single mother who left her drug addict deadbeat husband with a toddler in tow and a bun in the oven, and several inspiring entrepreneurs who overcame ridiculous odds. They humble me just reflecting on what they’ve accomplished.

Not surprisingly, there are a few characteristics these winners have in common – and that’s the purpose of today’s entry. I want to share the common characteristics of winners.


Characteristics of a Real Winner

Remarkable ability to withstand the pain: Unless you were born with a silver spoon where the sun doesn’t shine, all roads to prosperity are dusty, lonely at times, risky, nerve racking and somewhat uncharted. That’s what makes the stories of real winners so inspiring – realizing what they overcame to get to where they are… these people make adversity an asset.

Real winners have an incredible tolerance for adversity. They persevere through situations most people run from. In fact, they love the fight. Being challenged fuels them. Knowingly or not, they completely buy into Marcus Aurelius’ philosophy:

‘The impediment to action advances action. What stands in the way becomes the way.’


Relentless pace: Winners are routinely in 6th gear – but always calm. They’ve trained themselves to be this way.

Winners start early and end late, and in between are tallying daily victories because they fear mediocrity. They see opportunities throughout a day, big and small, and act – regardless of what’s scheduled.

Here’s a real world example: Along with a group of financiers, I was invited on a private jet to Japan by a very successful Canadian entrepreneur to visit his new foreign business. He was seeking to fund, via equity, this relatively new venture. Two days before he flew us out of Vancouver he went over to Japan with his technical team for some business development related matters. However, knowing he had a group of financiers flying to Japan from Vancouver, he flew back commercial from Japan solely to greet and conversate with us on the plane. Astutely, he recognized the long flight over was an advantageous time to get to know and prep us for the pitch…

Many successful entrepreneurs would have just saved themselves the 27-hour journey (back and forth to Japan), got some sleep and waited for us to arrive. But not him. He saw an opportunity to gain another win – which was to build a rapport with potential funders during the long flight. His decision enabled a smoother and very effective pitch in Japan.

This is called always showing up, simple as that. We all flew back from Japan five days later, and you better believe he came back with us. The man crossed the Pacific four times in a week!! How about that for pace?

The guy is the energizer bunny. And that’s why he’s a multimillionaire with several buyouts under his belt.


Creatures of routine: Winners have routines they rarely deviate. From the time they go to bed to their fitness routine to daily dedication to personal growth, real winners are religiously routine. Growth-oriented daily habits are what separate winners from Joe Sixpack.

It’s the weekend, what did you do today to make yourself better?


Embrace responsibility: Most of us have responsibilities – be it our children, businesses and so forth. Real winners look for more. They want to help an endless amount of people. They realize life’s most valuable currency is helping others out of the struggle – and enabling opportunity.

Winners take on causes outside their lives solely for the sake of making this earth a little better. For winners, a life filled with responsibility is a rich and a free one.

“Most people do not really want freedom, because freedom involves responsibility, and most people are frightened of responsibility.”

– Sigmund Freud


Compartmentalize:  The world’s winners know how to compartmentalize. They don’t carry yesterday’s drama into the boardroom today. They are fully present and understand the task at hand requires laser focus and an all-in play.


Thrive under pressure: Pressure makes diamonds. Winners revel in pressure-filled moments because their daily routines are designed to make them excel in these scenarios. They hate to lose and constantly have something to prove – hence why they’re winners.


Tight circle: You certainly don’t have to be a recluse to be a winner. But they are very careful who they give their time to, and they rarely have a long list of cronies.

Winners are fiercely loyal, but only to a select few. Perhaps it is a consequence of success and being used in the past, but winners understand that many people suck their energy and give little to nothing back. Time is a valuable currency for winners, and while they’re givers, they also expect to get a lot back from the people they hang with.

“If you hang out with chickens, you’re going to cluck, and if you hang out with eagles, you’re going to fly.”

– Dr. Steve Maraboli


We can all be real winners and great entrepreneurs. But it takes commitment and a deep desire to develop these characteristics. Think of all the stand-outs in your life. You’ll see they share these traits.

Want to be a winner?

Stay hungry,


P.S. We’re all meant to be champions. Subscribe to my newsletter below to learn about ways to excel and get ahead as an entrepreneur. Only my best content will land in your inbox.