Tips From High Stakes Poker Players: Tom Dwan And The Importance of Asking ‘Why?’

Not everyone reaches the apex of high stakes poker. Why do some become such stars that people want busts of them in their garden, while others ping pong between the stakes never settling on the side where millions of dollars are won and lost, daily? In ‘Tips From High Stakes Poker Players’ Lee Davy brings you the common principles and practices he has found in the stars of this ever-evolving hierarchy, beginning with the importance of asking ‘Why?’

Tom Dwan is an intensely private person. Interviewing him is challenging. Interviews are a dish better served hot. If you don’t include the right blend of ingredients, then it quickly goes cold. One of the most crucial elements of a memorable interview comes in the form of questions, and it’s ‘the question’ that sets this private man apart from the many who have tried and failed before him. 

Amongst the high stakes tribe, you find some incredibly creative people, and creativity is a primal aspect of humanness. It doesn’t matter if you are Walt Disney, Steve Jobs or Tom Dwan – humans are at their creative best as children. 

As children we are aware of the noise of passing insects, find incredible beauty in the form of pinecones and seashells, and make the most fabulous art with our food (very often on the floor). 

It’s at this early age that we are still unaware that we are adhering to a blueprint of life. The ‘zombification model’ handed to us by our parents, the educational system and early employers. 

With children, pregnant with fire, we encourage the behaviour of asking questions, but as we enter the educational system things change. The operatic way in which we get curious about the world is knocked out of us by the need to ‘fit-in’, and the constraints of the classroom clock and cockeyed curriculum.

Dwan shifts uncomfortably in his chair, looks down, prepares to answer my first question, looks directly at me, and a lopsided smile breaks out on the right-hand side of his face, one end almost touching his earlobe. Then his mouth opens for the first time.

“I always had this thing about me,” says Dwan with a pause. “I would ask, “Why?” If I had to do some work at school, or whatever it may be, I could do it, but I need to ask why? It needs to make sense to me.”

Paradoxically, as children there is a biological drive to become part of a tribe; not just any tribe, but THE tribe. We feel it in every organ, breath and cell. At the same time, this tractor like drive to be in someone else’s gang can also lead to a lack of character. 

It’s as we approach our teenage years that creativity, and being different begins to feel weird. We start to feel ashamed of who we are. We don’t want to ask ‘why?’ because we feel judged by our classmates. We fear to ask questions because we don’t want people to see who we are. If the mask slips slightly, we are out on our arse. Anyone who has pressed the intercom only to be greeted by silence understands the crushing insanity of loneliness.

Even those brave enough to ask ‘why?’ – People like Tom Dwan – are oppressed because the teachers don’t have time to deal with all the raised hands. There is a schedule to follow, and answering questions isn’t in the curriculum.

And it’s for these reasons that we slip into the zombification of life, taking orders from the thumb and forefinger of unimaginative people; quickly forgetting about the internal war that raged throughout our teenage years as a defensive mechanism for keeping the cognitive dissonance at bay. 

High stakes poker players don’t fit into that blueprint.

People like Tom Dwan found a way to escape.

They realised there was a price to standing out, and they were happy to pay for it.

As the author of Feck Perfuction James Victore puts it:

“Knowing that you don’t fit in is your first glimpse of greatness.”

Having an Opinion

Victore believes the point of life is to have an opinion, and the artist extraordinaire once said that ‘normalcy’ is barbed wire to the soul, and that questions are the wire cutters’.

There is nothing ‘normal’ about Tom Dwan.

 “I think there is a reason that I gravitated towards poker,” Dwan told me. “It’s because I got to pick my version of what made sense to me. I would choose the games that were more fun, or seemed like I could make money; picked the hours that I wanted. I didn’t realise any of that when I got into poker, but I think that’s part of the reason I stuck with it and was able to be pretty good at it.”

I have a two-year-old, and an eighteen-year-old, and I have realised that as a parent, I encourage the nipper to ask questions about life, and yet with the boy becoming a man, I slip into a modus operandi of forcing my opinion on him. 

There are times when my son has voiced controversial opinions, and rather than explore the reason why I have taken out my Nunchuks and smashed every word to bits the moment it leaves his lips. I see him in me, and why not – he trusts me and wants to emulate me in many ways. 

Speaking to Tom Dwan and many other high stakes poker players I see the value of raising children to trust their opinion so that they can share it with the world either verbally or through a form of artistic impression or creative endeavour. 

We have to feel the fear that other people will not like what we have to say and to say it all the same, and we do this by training our voice and allowing it to evolve, and most specifically, to sing, because if it doesn’t create a crescendo then how will anyone ever hear it? We need to replace the dulcet tones of zombification with a chorus of hues that illuminates the chandeliers of life. 

Why We Care.

Bernadette Jiwa is a marketing genius, author of a myriad of top-notch books, and the creator of The Right Company. Jiwa believes the ability to ask the right questions is the key to a successful company, and I will further that by replacing ‘company’ with ‘person’. 

Jiwa wants marketers to ask: “Why will people care about this?” 

I believe Dwan and many of his peers, have become accustomed to asking the question, “Why should I care about this?” It’s a question that created a cumulonimbus of speech bubbles that led to the world of high stakes poker.

Why does this idea matter to me?

Why should I give this my priority?

Dwan learned from a young age the compelling need to ask the right questions at the right time and to discern and prioritise essential tasks that emerged from these questions. 

In becoming a ‘question-asking machine’ Dwan also dug deeper than most, mining the gold that appeared on the face of the root cause rather than dilly-dallying with the symptoms like so many of us do. 

The secret to creativity is curiosity.

The secret to curiosity lies in the questions. 

And it couldn’t have been easy for Dwan and his peers. Nobody likes a rock, and some teachers are no different. The kid with no curiosity, the one who never raises his hand, is no problem at all. The Rocks are easily managed when compared to the kid who can’t keep still, and won’t stop asking, ‘why?’

It’s the same in the workplace.

Managers want you to follow orders, not ask questions. 

Without the ‘why?’ there is no thought of ‘how can we improve this?’

We think that asking a stupid question is risky, but it’s dangerous not to ask the stupid question.

“The worse thing you can do is deny who you are, try to be someone or something you’re not, and live a life bent and molded by others.” James Victore.

What I have taken away from my conversation with Dwan and some of his peers is that resurrecting our ability to ask great questions is a crucial skill in life. But Dwan’s success comes down to the way he acts once he receives an answer. There has to be a genuine interest in the response you receive. Let’s not question things for the sake of it. That will win us no favours. Be honest with ourselves about the ‘why?’ Poker is a game where you need to be several steps ahead of your opponent, and this is no different – be prepared with how you are going to respond to the answer to your why?

I suggest to Dwan that he must have been a royal pain in the arse in school, because of his refusal to fit into their box. He thinks about my statement for a second and then shakes his head. 

“Not really,” says Dwan. “It was more about WHY do I need to be in this box? If this box says, ‘You can’t quit because the fish wants to keep playing,’ I will play for 50-hours. But I need the reason to make sense to me. That’s the thing I like about poker. There is a lot of freedom in certain respects.”

There isn’t a player competing in the highest stakes of the game, professional or businessperson, who contorted to fit into a box, square or office cubicle. The world has enough boring, bland, bullshit. Tom Dwan and the men and women of poker who followed the same path are artists; geniuses, people who don’t fit in, and from the very outset, didn’t even try.