Stop Grinding Away: Win Big at the Tables That Matter
Are You Playing It Safe or Taking Your Shots? Communication Skills Are What Separates Legends from Grinders
In New York’s underworld, Joey Knish is a legend.
He’s been earning money playing illegal card games for 15 years. Starting at 19, Knish operated with a simple playbook. Play it safe, treat gambling like a job. “That’s how you make a living playing cards in Manhattan,” he’d advise the young guys.
He’d see new faces once in a while. Somehow, these dudes would find their way into basements and breakrooms for these “off the books” games. They dance into the shadows looking for glory. Most of them, Knish knew, won’t last long.
The underworld isn’t for everyone. It smells funny and there’s a lot of illegal shit happening.
Knish is comfortable here. He finds it fun and exotic and rhythmic. He hears interesting stories from many of the “regulars.” Conversations about gambling, cheating, and stealing while bets are raised. Being a grinder beats hustling away at some corporate job.
Knish’s life philosophy was formed in these rooms. These rooms have been his best teachers, no doubt. Especially, playing Texas Hold ‘Em. Grind it out, hand by hand, for hours on end. Learning how to spot people’s tells.’ The way to move their lips or look to the left gives away their cards. Learning when to bet and when to fold, on the fly while the game unfolds around you.
Knish is an exceptionally skilled card player. He has the endurance to play well into the morning hours. His ability to adapt on the fly is sharp. He liked that Bruce Lee quote, “Be water.” Words he kept as his phone background for a year.
Knish loved the challenge of a table full of skilled poker players. Everyone has different cards and a different method to play them. That’s why he grinds it out, week after week. Playing conservatively, spending long hours behind the table. Rain, sleet, hail, snow. Trying to win one big pot an hour.
That damn alimony check thought Knish.
Still pissed at himself for that. His marriage fell apart because he misread the table. He thought he had the better hand. He was wrong. Now he’s paying for it, grinding out another $500 extra a week. Spending even more hours in these smoke-filled rooms.
Someone recently asked him, “How are you?”
“The same,” he said, stonefaced. Exactly how he wanted to be. He wished Mike understood this. Knish had been mentoring Mike for a couple of years. Teaching the kid his playbook. Develop your skills, one game at a time, and play your game. Understand which games to play, smart risks to take, and how to win.
“My kids get to eat,” Knish bragged, feeling satisfied and a little bit smug. Mike was one of these glorychasers. He has frosted blond hair and studies law. He had to admit Mike had “stones” to take risks. His stones got him into a mess.
“I play for money,” Knish continued his lecture, looking down his nose at Mike through stern brown eyes. “I have the stones enough not to chase cards, actions, or stupid pipe dreams.”
Mike was back at the big table with the red felt with three stacks of high society. Across from him is a guy they call “KGB.” No one could beat KGB. Mike tried one year ago and lost 30 thousand dollars. On top of that, Mike now owes KGB $15k, due in full by morning.
The debt isn’t even his. Mike vouched for the wrong guy, a friend who wormed his way out of trouble. He’d skipped town, leaving Mike all alone to handle his debt. “Didn’t I tell ya,” Knish lectured Mike. “But, ya didn’t listen, you never listen.”
“When are you gonna learn?”
“You know what I learned, Knish,” asked Mike. “I’m going to keep taking my shots.” Now, Knish was looking at Mike from across the room. He looks a little rough. Knish first looks at Mike’s busted nose, then he sees the massive cut on his forehead, right between his eyes. That had to hurt. So will this game.
Owing the Russians money can be deadly, Knish heard enough times to stay away from KBG’s table. If Mike loses again, KGB will own him, and Mike’s face will look a lot worse. They are playing high-limit Texas Hold ‘Em, head-to-head.
Knish had hoped Mike learned to stop “chasing pipe dreams” at this very table with the red felt, underneath the yellowish hum of the overhead lights. Apparently not.
Knish looked through his orange-tinted glasses at Mike’s stack of chips. Three times the size of KGB’s.
Mike’s blue eyes sparkled as if he’d figured something out. He’s confident and in control. Pushing KGB against the ropes. Knish rubbed his face nervously as Mike went all in just as he had a year ago. Maybe Mike did learn.
Each player had two cards, face down. Three cards lay face up in the middle of the table. Chips are spread everywhere. This pot must be worth $60 grand. Enough to cover Mike’s debts and get him to Vegas for that pipe dream.
Too risky for this grinder.
The room, hidden behind a green steel door with a weird sliding peephole, was thick with anticipation, waiting for the reveal. When the cards were turned, KGB didn’t have it. Mike did. After a few minutes of turmoil, the energy in the room settled.
“Well played, Mike,” Knish said.
“Thanks, Joey,” Mike replied. “Turns out, you did teach me a lot. I learned that if you’re not careful, your whole life can become a grind. You gotta keep taking your shots. That’s what legends do.”
As the two shook hands, Knish thought about how much life mirrors the poker table. Playing it safe keeps things consistent. But, turns out, when you play it safe, you end up settling. You don’t give yourself a chance to win big if you don’t sit down at the big tables. Grinding is choosing security over your dreams. Mike took a risk a year ago and lost. But that experience taught him how to go all in on himself.
Something Knish never did.
Which character are you?
Which do you aspire to be?
Joey Knish is consistent and stays “the same.” Mike bets big on himself, showing up fully, knowing his losses inform him.
In this room, we develop communication skills to use at the big tables, like poker players, to win more pots and achieve our goals.



Great story, Rob. I was just having a similar conversation with a wise old man using this same poker metaphor - not about careers, but about how we help people. I appreciate the opportunity to bring both together here.
I think the real difference isn’t just safe vs. bold. It’s percentage thinking.
In poker, you play the hand that wins 85% of the time, even though you’ll still lose sometimes. But smart players also know not to keep betting into a hand with no chance to improve.
Life works the same way. Whether it’s business, opportunities, or helping others, we’re always putting chips on the table - our time, energy and resources. The skill is knowing:
Is this a high-percentage moment?
If yes - push chips.
If not - fold without guilt.
I’ll be honest, I haven’t mastered this. My instinct is usually, “Sure, I’ll carry the whole hand.” I’m still learning where the odds actually justify the bet.
Boldness gets attention.
Percentage decisions build careers, judgment, boundaries and the energy to keep showing up where it truly matters.
That’s the real skill in life and leadership - not “always say yes” (bold) or “never get involved,” (safe) but knowing when your effort actually creates forward movement (%). ❤️
That Joey Knish vs Mike contrast hit — “play it safe” can quietly become a life sentence.
I love the way you tie taking shots to communication at the “big tables,” because the risk is often saying the thing you actually mean (or asking the real question), not just staying agreeable.
Curious: when you’re coaching someone to “take a shot,” what’s your favorite *small* move (one sentence) that changes the whole table dynamic?