Going All In with Henry Rollins - Gambling Tips and Life Lessons

Most people know Henry Rollins as the scary, angry, and intense lead singer of the Rollins Band. But there is a lot more to him than the screaming metal icon that was the man behind the song Liar. Rollins is a modern-day renaissance man. He’s a poet, author, radio host, journalist, political pundit, producer, and actor but most of all he’s a gambler.

Not a gambler in a traditional sense. He has come out and said that he doesn’t even understand the concept of gambling in an article he wrote in LA Weekly. But, in his life, he’s a guy that is willing to risk it all to try and win it all. Which is pretty amazing knowing his beginnings. As a child, Rollins suffered several life-altering experiences.

The first experience was a medical diagnosis of hyperactivity (now referred to as Attention Deficit Hyperactivity Disorder or ADHD). In the 1960s this was an uncommon diagnosis. Children with this disorder were generally considered troublemakers, unfocused, or, in some cases unteachable. Rollins mother had the insight to take him to a doctor to have him tested. The doctor decided that he should take Ritalin, a new drug used to treat hyperactivity. Rollins would go on to take the drug until he finished school.

The next experience that would alter his life was being grabbed off the street, pulled into a van and molested at the age of 10 by a man in Greece. The third experience that shaped Rollins was his time at the Bullis Preparatory School in Potomac, Maryland . This school would form the backbone of Rollin’s incredible discipline and strong work ethic. And it was the place where Rollins wrote his first songs.

Making that First Big Bet

After high school, Rollins and his friend Ian MacKaye heard their first Ramones album. This was the start of Rollin’s life-long love of punk rock. Because of this, Rollins started working as a roadie, setting up equipment for local DC bands. One band, in particular, was the Teen Idles.

As he worked with the Teen Idels, he learned their music and how to present himself on stage. He also developed an intimate knowledge of their behaviors. One of the band members stopped appearing at practice sessions. When this happened, Rollins “rolled the dice” and asked the band to let him take the helm as the lead singer. The band eventually agreed. As the singer for the Teen Idels, Rollins gained a reputation in the DC music scene as an energetic and somewhat scary front man. A great combination for a punk rock band.

Betting to Build Your Bankroll

After a year with the band, Rollins took his new found reputation and took another gamble. He formed his own band called State of Alert (SOA). Using money he earned as an assistant manager at a Häagen-Dazs Ice Cream store in Georgetown, he financed the recording and pressing of SOA’s only album.

After the album was released, the band did about a dozen shows and broke up. It would seem that all the money that Rollins spent was a bad bet. But Rollins knew better. It was about this time that MacKaye and Rollins first heard Black Flag’s Nervous Breakdown EP. Rollins would become a huge fan. He started writing and sending his music to the band’s bassist Chuck Dukowski.

In his letters, he invited the band to stay at his parents’ house when they toured the East Coast. Dukowski and the band accepted his offer and stayed when they toured in 1980 and again in 1981. Rollins attended many of these concerts, and, at one of them, he was invited on stage to sing. The next day, the band asked Rollins to do an impromptu audition. The band wanted to add a new member so that the singer Dez Cadena could move from vocals to guitar. After the audition, Rollins was offered the lead spot.

Had Rollins never gambled made that SOA EP, he would have never had the credibility to approach Dukowski. By making the EP and then sending it to the band, Rollins then would wind up meeting them and auditioning for them. He took what seemed like a losing bet and turned it into a jackpot.

Going All-In

Rollins had a big decision to make. Accepting the Black Flag offer would mean quitting a steady job with some growth potential. He was a 19-year-old assistant manager of a new national brand restaurant. The choice was to scoop ice cream for the rest of his life or follow a dream.

For Rollins there was only one answer, he went all-in. He quit his job (his boss commented that he would be back in a few weeks), he sold his car, most of his possessions, and moved to Los Angeles to front the band. When he first arrived, he was so confident that the venture would be successful, he got the Black Flag logo tattooed on his left bicep and his neck.

Sometimes You Have to Grind

Poker grinders look for the small wins. They play long periods of time and only risk small amounts. Over the 6 years following Rollins joining Black Flag, he could be compared to a grinder. Rollins would tour the world with Black Flag. They would record 8 albums between 1981 and 1986, shifting gears with the culture moving from punk to metal. The band would see minor success, but not anything that made them millionaires.

Rollins made enough to survive. He lived in a shed in a friend’s backyard (by choice as he liked the solitude). All the while, he was working towards his next big step. Know When to Leave the Table and Try Playing a New Game. In 1986, Black Flag disbanded. It was time for Rollins to play a new hand at a new table. This time, Rollins became a solo act. In 1987 he released his first 2 solo albums Hot Animal Machine and Drive by Shooting under the pseudonym Henrietta Collins and the Wifebeating Childhaters.

Neither one of these albums were commercially successful. But you don’t win every hand that you play. Rollins knew this. Rollins decided that he would change his strategy. This strategy would not be one that would give him immediate success but would lay a foundation for a consistent string of wins.

Starting Your Own Game at Home

Playing at a casino is exciting. It has all the action you could ever want. But sometimes it’s fun to set up a table in the basement, invite some friends over and play a few hands. It can also be a great way to end a string of bad luck by grabbing a few wins and gaining confidence. That would be the case with Rollins. While he still was recording music and had a record contract for his music, he created his own record label 2.13.61 (his date of birth). He used 2.13.61 to make records in his new medium: spoken word.

His first album Short Walk On A Long Pier was a compilation of performances in Los Angeles, San Diego, Baton Rouge, Denver, New York City, and Amsterdam. Rollins stated in the liner notes of the re-release of the album that it was “just awful.” Despite his dislike of Short Walk, he released a second spoken word album Big Ugly Mouth. It was recorded during various tour dates in 1987 at Madison, WI, Chicago, IL, Minneapolis, MN, Denver, CO, Los Angeles, CA, and New Brunswick, NJ.

Musically, he added more members to band lineup and rechristened them as the Rollins Band. All of the gambles had a big payoff. He was invited to participate in the biggest touring festival of 1991, Lollapalooza. He also signed a major record deal for the Rollins Band with Imago Records.

No Matter What Your Strategy, Bad Things Happen.

There are times at the roulette table that you bet on red or black and green comes up. There are times at blackjack that you hit on a 12 and you get a face card. That’s life. You can make the decision to play the next hand or leave the game. This was a choice that Rollins had to make in December 1991. Except, it was a much harder decision for him.

Rollins and his best friend and former Black Flag roadie Joe Cole were returning from the Whisky a Go Go where they just attended a Hole concert. They had reached the outside of Rollins home when 2 armed robbers attempted to mug them. They only had $50 between them. Angered, the muggers ordered Rollins to go inside and get more money. Rollins went in and out the back door to alert the cops. While this happened, the robbers wound up killing Joe Cole with 2 gunshots to the head. Rollins wasn’t injured.

Due to Rollins image as a loner who liked to get in fights and start trouble, police suspected him as the assailant. The police would bring him in and questioned him for over 10 hours trying to get him to admit he was the killer. To this day the Rollins keeps the bloody clothes and the dirt from where he died in a plastic container to remember him by. The murder remains unsolved. If it was poker, Rollins could have folded, walked away and never played again. Instead, Rollins would channel that anger and frustration over his best friend’s murder and double down on everyone.

Hitting the Jackpot

1994 would be the year Rollins would truly break out. Rollins would release his most successful commercial band album Weight featuring the hit song Liar. He also appeared at the show that would be a launching pad for many 90’s bands, Woodstock ’94.

Rollins would win a Grammy for his spoken word album (and my favorite of all his work) Get in the Van: On the Road with Black Flag. This 2 CD set chronicled his days from the time he substituted for the Teen Idles to the end of his stint with Black Flag. The album beat out a spoken word version of the Bible read by Gregory Peck, Kenneth Branagh’s version of Hamlet, Ben Kingsley’s reading of Schindler’s List, and Ken Burns spoken word version of his documentary Baseball.

Rollins would also show his range by landing an acting role. He appeared opposite Charlie Sheen in the 1994 movie The Chase. He played, of all things, a police officer.

Playing a Different Game

While he still was performing with the Rollins Band and still recording spoken word albums, Rollins made a major foray into acting. Much like a poker player might switch to blackjack now and again, Rollins made appearances in 3 movies over the following year. They were:

Heat starring Al Pacino
Johnny Mnemonic starring Keanu Reeves
The David Lynch film Lost Highway starring Bill Pullman

He was like the player who went all-in at the World Series of Poker, won all his games and walked away with the grand prize.

Tired of the Game. Time to Bet on a New Game.

By 2004, Rollins had lost interest in making new music. He had done it for over 25 years and had done all that he thought he could. But he still loved the thrill that came with the game. So he would look not for a new table, but new games to bet on himself with.

He had appeared in a few movies, but they were just brief spots. He wanted to challenge himself. So much like a poker player learning to bet on craps for the first time, Rollins studied the game. When he was ready, he stood at the table. And while he knew he wouldn’t roll a 7 the first throw, he knew that he wouldn’t roll snake eyes either.

Part of Rollins issue was that he’s a loner. This is due to depression that he has battled over his lifetime. But he wouldn’t let it stop him from playing the game. He threw himself into roles and gambled that he would get them. And he has done quite well. He has appeared in movies and television as well as cartoons as a voice actor. What can this teach us? You are never too old to learn a new game and risk it all in that game.

Putting Your Heart into Your Game

Most casino games are games of skill. You learn strategies and odds and you place bets accordingly. But the thing that separates the guys who win here and there and the consistently big winners is heart. Rollins shows us that when you play the game, you play it with heart. Nothing says this more in life by exposing yourself to public scrutiny. Especially when you are a private person.

Over the years, Rollins has written and recorded several spoken word and autobiographical books. Each one about aspects of his life. He bet that you would care. He bet that you could learn something. He bet his heart. His books include:

Black Coffee Blues
Do I Come Here Often?
The First Five (a compilation of High Adventure in the Great Outdoors, Pissing in the Gene Pool, Bang!, Art to Choke Hearts, and One From None)
See a Grown Man Cry, Now Watch Him Die
Smile, You’re Traveling
Get in the Van
Eye Scream
Broken Summers
Roomanitarian
Solipsist

Occasionally, Someone Bets on You

In craps, you may be the shooter and you may be placing a bet on yourself, but others are betting on you too. That happened with Rollins as well. Vanity Fair magazine tapped Rollins to become a contributor to the Politics and Power section of their website in 2008. Known for his liberal views and acerbic treatment of the right and those on the left that act contrary to the public good, Rollins reporting jobs grew.

First, Vanity Fair expanded Politics & Power to include a special subsection for Rollins called Straight Talk Espresso in 2009. The next year Rollins began writing an online music column for LA Weekly. The 2012 Presidential election landed him gigs with alt news site Words with Meaning!, as well as The Huffington Post, and a YouTube series called “Capitalism 2012”. These publications bet that Rollins had something to say. And he did. They wanted him to hit point on the table and he did.

Don’t Be Afraid To Learn New Game Variations

I love Texas Hold ‘Em. It is my poker game of choice. But every now and again I get tired of waiting for spots to open up online or I don’t like the table at the casino. So I had to look for another poker game to play. It took a few years to get where I wanted to be, but now I play a lot of Omaha.

Rollins had been on the radio for years as a recording artist. He had done some acting. But he never did a live talk show. That changed in 2004. Rollins hosted his first radio show Harmony in My Head on a Los Angeles radio station. The show was an eclectic mix of rock, jazz, punk, blues, reggae, world music, and other genres. It focused on B-sides, bootlegs, and rarities. In 2009, the station that broadcast Rollins show went off the air.

A public radio station in Santa Monica announced in February 2009 that Rollins would be hosting a live show on Saturday nights. The show has since moved to Sunday nights. He was good at Texas Hold ‘Em, but he wanted to learn Omaha.

Conclusion

Did Rollins walk into the Bellagio and lay down $1 million and walk out with $10 million? No. Did he bet $100,000 on the Mayweather v. McGregor fight and walk home with a hefty sum? No. Did he buy a lottery ticket and win the big jackpot? Or any jackpot for that matter? No again. Rollins stated that he doesn’t understand gambling. But after reading this, we all know that isn’t true. He just isn’t a casino gambler. He gambled when he asked to sing with the Teen Idels.

He gambled when he jumped on the stage with Bad Brains. He gambled when he formed SOA. He gambled when he quit his assistant manager job at the Georgetown Häagen-Dazs Ice Cream store, sold his possessions, and traveled across the country to become the lead singer for Black Flag.

But the gambling didn’t stop there. He and Black Flag gambled when they moved from the punk to metal genres. He bet on himself when he started 2.13.61 and started his solo career. He was able to bet on himself again after the tragedy of the loss of Joe Cole. He channeled his pain into more albums, a producing career, an acting career, a Grammy Award, a writing career, a radio career, and a journalism career.

He took chances. He took measured chances, but chances nonetheless. He made what may have seemed like crazy decisions to those around him. But these were all logical extensions of what he was already doing.

When you bet, you make logical decisions based on strategy and mathematical probabilities. You may win or you may lose. But the chances of winning increase if you follow a plan. Rollins won in life at most of his gambles because he followed a plan. So can we learn about gambling from someone who hasn’t ever placed a wager at a table or dropped a coin in the slot and pulled the handle? Definitely.