Gambling Edutainment · The OG Guru

AGAINST ALL ODDS

"Everyone said Fold. I Raised."

Luck runs out. Experience cashes in.

25+
Years at the Table
6
Original Shows
Stories Left to Tell
Scroll

"I didn't study the game. I lived it."

— Kenna James · 25+ Years on the Felt

Professional Gambler · Poker Coach · Contrarian · Storyteller

The OG Guru

The Guy Who Actually Did It

Twenty-five years ago, everyone said it couldn't be done. You can't make a living gambling. You can't beat the house. You can't back yourself against those odds.

Kenna James did it anyway. For 25+ years he played, coached, won, lost, and came back for more — building a life most people are too afraid to even dream about.

Now 54 — a full deck plus jokers — he's giving it all away. Every strategy, every tell, every hard-won lesson from the table, delivered with the wit of someone who's seen it all and still raised anyway.

See The Shows ↓
🔥

Rebellious

Built a life doing what others said was impossible. That IS the show.

🎯

Authentic

Real losses. Real wins. Real strategy. No script, no filter, no apology.

🧠

Educational

Every laugh lands a lesson. Every story hides a system worth knowing.

Unshakeable

Nothing rattles the OG Guru. That calm is the most powerful thing on camera.

Private Coaching

Private 1-on-1 Coaching with Kenna James

Play at a Higher Level

You've got the fundamentals. Now it's time to close the gap between the player you are and the player you know you can be. Kenna James brings 25+ years of professional poker experience directly to your game — identifying leaks, sharpening your reads, and building the mental discipline that separates competitors from champions.

Sessions are private, personal, and built around your game. One hour. One coach. No fluff.

1-on-1 Zoom Sessions
Personalized Game Analysis
25+ Years of Pro Experience
Mentorship Programs Available
Apply for Private Coaching →
Content Slate

Six Shows. One World.

Every format designed to hook, teach, and keep you coming back. From 60-second edges to full storytelling deep-dives — there's a show for every mood.

Flagship · Weekly

The Long Game

Deep-dive storytelling around a real hand, pivotal decision, or defining moment. Strategy buried inside a war story. Always personal. Always a lesson you won't forget.

Strategy· Storytelling· Weekly
Viral · Short Form

The 60-Second Edge

One tip. One minute. Delivered like a secret being passed down from someone who's paid for it the hard way. No fluff. Pure gold. Stop scrolling.

Tips· Quick Hit· Daily
Live · Interactive

Sweat It With Me

Real-time play with a live Decision Dashboard overlay. You vote every hand — fold, call, or raise — then watch exactly what happens. Skin in the game, zero risk.

Live· Interactive· Community
Episodic · Storytelling

Scars & Chips

One true story per episode from 25+ years on the felt. Funny, honest, occasionally painful. The kind of stories that make you pause the video to tell someone else.

Stories· Legacy· Episodic
Reaction · Collab

Young Blood, Old Rules

React to how younger players approach the game — with genuine curiosity, sharp wit, and the kind of correction that only comes from someone who's been there.

Reaction· Collab· Humor
Community · Viewer-Led

Stack or Bust

You submit your real hands and worst gambling decisions. Kenna analyzes them live — ranked from genius to what were you thinking. Coaching that actually entertains.

Community· Coaching· Weekly
The 60-Second Edge · Pilot Episodes

The Edge Starts Here

Four pilot episodes. Four angles. All killer, no filler. This is what 25+ years at the table sounds like when it's distilled into sixty seconds.

60 SEC Episode 01

"Set yourself up for Success!"

Why these 3 core elements need to be in place before you even play the game! Hungry, Healthy and Happy!

60 SEC Episode 02

"The Most Expensive Seat in the Room"

Why most gamblers lose before they even sit down. The casino built an entire industry around one type of player. Is it You?

60 SEC Episode 03

"The Insiders Secret"

"Seriousness with fluidity is concentrating without effort! Take what you're playing for out of play!"

60 SEC Episode 04

"The House Always Wins... Until It Doesn't"

How to find the edge. The house maximizes profits by selling YOU the Experience. Make that Experience Finding your Edge!

Group Coaching

Live Training in Real Time

The Against All Odds Group Coaching Session

Join a small group of serious players for a live, topic-driven coaching session with Kenna James over Zoom. Each session focuses on one specific area of the game — deep, practical, and immediately applicable at the table.

$50
Per Session
8
Seats Max
WED
Nights · Zoom

Wednesday nights. 8 seats. When they're filled, the lesson happens.

Reserve My Seat — $50 →
Find Your Player Type

What Kind of Player Are You?

How do you approach a high-stakes situation — at the table or in life? Pick the one that's most you.

"Kenna helped me take control of my mind and learn how to stop spinning out of control. I've learned to approach each hand with a strategic perspective, turning seemingly random events into calculated moves. The emphasis on decision-making has not only improved my poker skills but has had a positive impact on my overall mindset and approach to challenges."

Craig Gubert - Detroit, MI

 "I wholeheartedly endorse Kenna James for coaching.
Kenna possesses an extraordinary ability to diagnose issues swiftly and provide effective solutions. His keen insight into the intricacies of the game and life itself has been invaluable to my personal and professional development.

Brian Battistone - Las Vegas, NV

 

Get in Touch

Let's Talk Poker!

Questions about coaching? Ready to take your game to a competitive level? Reach out directly and Kenna will get back to you personally.

The Insider's Edge — Free Weekly

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