He set out to become an actor.

Which meant (like every aspiring Hollywood actor in the 80s) he did whatever it took to stay on stage. Mime. Clown. Magic shows for kids. Waiting tables on Rodeo Drive while serving $800 bottles of wine to people who actually made it in Hollywood.

For more than a decade he chased roles. Soap operas. Stage plays. Commercial auditions. The trunk of his car full of clothes for quick costume changes between auditions.

And when that dream started to fade… poker showed up.

Not in a casino.

In a garage.

Kenna was 14 years old, pockets full of paper route money, when his friend’s dad invited him to sit in a game with a bunch of Army guys playing a brutal little game called Guts.

His strategy? Simple.

“If I never let go, I can’t lose.”

It wasn’t exactly solver-approved strategy. But it did something more important. It gave him the bug.

Then poker disappeared from his life for almost twenty years.

Until a friend handed him a book: David Sklansky’s Hold’em for Advanced Players.

Kenna read it. Then read it again. Started writing down every hand he played in a notebook. Went to dealer school at Hollywood Park. Dealt cards during the day. Played $0.50/$1 limit hold’em at night.

The actor became the student. The student became the pro.

And suddenly the guy who used to vacuum department store windows as a mime was traveling the world playing poker. Austria. Amsterdam. Moscow. Final tables. TV cameras.

One moment from that era still sticks with him. The 2003 WSOP Main Event, the year Chris Moneymaker changed poker forever. Kenna made a deep run and found himself suddenly sitting on the feature table under the lights.

He went on break, walked into the Binion’s parking garage, called his brother… and broke down crying.

Not because he lost.

Because he realized how big the moment was.

Poker does that sometimes.

If you’re new around here: every week (or so) we pull a gambler straight out of their seat at the table and ask them how they got there… and what happened when the heater cooled off.

This week’s episode is Kenna’s full arc—from mime and actor… to traveling poker pro… to surviving the poker boom… to losing almost everything in 2008… and rebuilding his life from the ground up.

Along the way he: ran one of the first major poker tournaments in Moscow… played poker with the writer of Rounders and watched Ed Norton walk into the card room… got stacked by Gus Hansen… and won a bet that somehow cost him $500,000.

Yes. You read that correctly.

Kenna won the bet.

And it still cost him half a million dollars.

Poker is weird like that.

Kenna’s story also happens to double as a time capsule of early poker. The era when tournaments had 150 players and folding chairs. When nobody studied the game. When limit hold’em ruled the card rooms. When the poker boom hadn’t quite happened yet but you could feel it coming.

We talk about the garage poker game that started it all… the Sklansky book that changed everything… dealer school and the Hollywood Park card room… running the first poker tournament in Russia… the emotional moment during the Moneymaker WSOP… getting knocked out by Gus Hansen… and the legendary Mike Sexton prop bet that turned into one of the greatest hustles ever pulled.

Kenna now spends most of his time coaching players—not just on poker strategy, but on life. His belief is simple: poker is a mirror. Whatever weaknesses you have in life—impatience, ego, fear—they show up immediately at the table. Fix those, and the cards often take care of themselves.

Reply and tell us the strangest job you had before poker. Kenna’s might still win the prize.

🎧 Listen / Watch

YouTube: https://youtu.be/uAGp4Ee5Ri4
Spotify: [processing…] (Check the channel when it goes up!)

See you next week!
— Art & Justin
🃏 @artparmann & @justinyoung07

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