Up Close With Author and Ironman Poker Record Holder Damon Shulenberger

Contributor: Marissa Sayno

damon shulenberger

Freelancing is like playing a hand at poker… or, is it?  In this exclusive interview with freelance writer and Ironman Poker Record Holder, Damon Shulenberger, you may just learn that ‘everything happens for a reason’.

Q1: How did you start as a freelance writer?

It was a gradual process, to say the least. It began when I was an eikaiwa teacher in Japan and gained an interest in Nihon-no culture and language. A little burned out from teaching, I looked around for avenues as a writer. I joined the Society of Writers, Editors, and Translators (SWET) in Tokyo and, under the guidance of Lynn Riggs, began writing articles for the SWET Journal, including Editing in Japan: Three Perspectives. Returning to the United States after 6 months of manning the desk at a youth hostel in Waikiki, I completed a graduate degree at the Monterey Institute of International Studies (MIIS). During that time, I authored articles for the school newsletter, the Foghorn.


Meet Damon: Freelance Writer & Author

Having pursued an internship in Washington D.C. at the International Trade Commission, I simply could not find any job openings––this was in 2009, at the height of the economic crisis. I had mountains of graduate school debt to pay off and was a month or so away from being out on the street. I felt that my talents in language were strong, so (through Craigslist) started freelancing for a Silicon Valley startup that needed writers who could compose large quantities of search engine optimized (SEO) materials for business clients. In addition to anonymous SEO content on every topic under the sun, I authored a couple dozen articles promoting (I am interested to see if some scholar from future generations follows the Internet cookie-trail of anonymous articles I wrote, to wherever they lead. Similar to Hemingway’s old journalistic exercises or Jimi Hendrix’ mid-60s session work with R&B artists like Little Richard. The material is strictly commercial, but not without interest to forensic literary sorts.)

Q2: What is the toughest challenge you’ve ever faced freelancing?

The biggest hurdle was psychological: trusting that I could produce quality content and get paid fairly. Before 2010, I had never attempted a Digital Nomad lifestyle and I found it hard to believe that the work would not simply dry up at some point. After 6 months of writing marathon prose (10 pages a day) and earning a consistent salary, I took that leap of faith and started to travel while writing. I chose the Philippines because I love tropical beaches and the friendly, unpretentious culture.

Q3: Would you say that freelancing is like playing a hand at poker?

One thing I noticed covering the World Series of Poker (WSOP) in Las Vegas over 6 weeks this summer was that poker and freelancing are very similar. You have to live by your wits and there are a lot of sharks. No one is totally secure. The gig economy keeps you on your toes and ensures that you live life to the fullest. I feel I have lived 20 years in the past 4 years. Amazing experiences, many of them by the beach, in countries from Jamaica to the Philippines. One other thing that poker has taught me is how to read people, wherever I go. I rarely wind up in uncomfortable situations because poker has given me insight in reading people’s true intentions––such as when they are bluffing or telling lies. I have met good people in many locations around the world, and been burned surprisingly few times.

Q4: Did you have a strategy before you started your nearly 49 hour Iron Man poker run and did you stick with it? If not, what were the reasons for deviating from that strategy. What are some key strategic lessons that we can learn from your Iron Man Poker win?

damon4My basic strategy was to take lessons learned from being a freelancer and apply them on the felt. While working with, I gained a reputation as an endurance writer. I churned out many pages of professional content, seven days a week. I was told my nickname, among the in-house editors and production managers, was “King Kong.” This has not stopped me from losing the ability to make a full time living at the job in the past year. The reality of freelancing is that wages are getting continually pushed lower as companies cast their nets wider for qualified applicants. Company loyalty, unfortunately, means very little. On the other hand, this system does encourage creative types like me to scramble and strive to fulfill their dreams. Self publishing A Very Dark Game, a ringside book on high stakes poker (my current leap of faith) would not have been as possible a decade ago.

As far as practical Ironman strategy goes, having lived in Asia extensively I had an acute awareness of how people at the Manila APT-Resorts World event viewed me at the table. I have lived between cultures for so long, I embraced the fact that there were players from the Philippines, Korea, Germany, Malaysia, Singapore, Australia, and England. Poker is a social game and I conversed with everyone. I tried to project a tight-aggressive image, such that I could get away with a major bluff occasionally. Taking calculated risks was easy, staying awake for nearly 49 hours straight was the hard part. Outwit, outlast, endure. Somehow I did it, winning the most challenging competitive endeavor of my life.

Q5: During the world record-breaking Iron Man Poker tournament, you must have felt mentally drained. How did you overcome doubts and tiredness, and persevere? How did you remain positive?

For the first day or so, I was having the most fun I had ever had in my life. Endless hours of ultra deep-stacked poker, where the most complex strategies come into play. Let me put it in perspective– the $1 million buy-in One Drop, which I covered in Vegas, starts with 3 million chips and plays extremely deep stacked at first––but blinds progress quickly and it turns into a “shove fest” by Day Two. With a fast structure, a lot of high level poker strategy is lost. The Ironman was the most insane tournament ever devised– the same hour-long structure as the WSOP Main Event, with 3 times the number of chips (each player had a 100,000 starting stack). Blinds never came into play, during the entire 49 hours of play––it was like playing in the fabled Big Game in Macau. The Chairman there despises “hit n’ go” professionals and players must play continuously for at least 24 hours (or until they are down $1.5 million) or they are never invited back.damon3

Q6: Tell us more about the books you’ve written so far.

My first book (Upon Breaking Out Of The Straits) was written in the mid 1990s, and photocopied and hand-stapled. It featured my own illustrations and I gave away maybe a dozen copies to friends. No one had anything positive to say about it, so I guess it was not so great. I next wrote two additional books of poetry: East To West, describes my experience living and teaching in Japan in the early 2000s. It is strictly available on Amazon at this point, although I would like to see a nice print edition someday.

More recently, I worked on the poetry-art project Earth Fabric with my friend, the Boracay artist April Jardine Limuran. This ambitious 2-year project had me writing a poem for each artwork April completed. Earth Fabric came together as a print edition in late 2013, directly because I won the Ironman tournament. We had just finished work on the final poem and artwork, and I promised myself that if I won, I would see the project through to completion. Earth Fabric is featured on the website my friend Nils Sens designed as a collectible hardbound edition. (It is also available on Amazon as an e-edition.) I have given copies out to friends and acquaintances and am satisfied with the results, though I am basically still a starving artist.

Q7: What projects keep you busy these days?

The poker book, A Very Dark Game, and the 400-page literary mystery thriller, Arisugawa Park. The latter book has an agent and I just need to complete revisions before it can be shopped to publishers. The poker book AVDG is one I am planning to self-publish as an e-book in late December, right around the time Daniel Colman is selected as poker’s Player of the Year. I have a lot of stuff in it that is only known to poker nerds, which I feel the general public will be interested in.

Q8: What was it like winning the longest continuous poker tournament, which earned you a Guinness World Record?

It was like a dream I never woke from, because I was nearly dead at the table when I won. It was like going from endless purgatory to poker heaven. And the poetry book gave me a sense of purpose and mission. Everything happens for a reason.

Q9: What’s the inspiration behind your upcoming books, ‘Arisugawa Park’ and ‘A Very Dark Game’ (AVDG)?

I began Arisugawa Park in 2005, during my last year teaching English in Japan. I was trying to capture a kind of Roppongi film noir feel that was haunting me at the time and I watched as it gradually expanded into a kind of Steinbeck meets LeCarre vision. I started AVDG a month before I won a mystery writer’s conference and met my current agent. I was desperate to transition beyond freelancing, you see. My salary had not gone up––had gone down significantly over the past year. I was living on the edge. The writing was on the wall: unlike with traditional jobs I would never earn any more than I was unless I “made it happen.”

Q10: How many years did it take you to finish these?

Many, many years. Decades. Until gaining an agent this year, I was basically unknown. Rejected so may times, by dozens of publications and agents. We live in a very odd time where Youtube hits are seen as an indicator of marketability and talent. Through a process of continual failure, I discovered myself. Now I hope to discover other worthy writers, who cannot easily fit through the traditional publishing doors.

Q11: Would you say that freelancing is ‘a very dark game’?

Not really. I gained the ability to write 10 pages of content each day, meeting the high standards expected by U.S. businesses and corporate executives. This was far from easy at first: as a freelancer, you must set daily goals and adhere to them strictly. There is no safety net if you stop working and no boss to tell you how much or how little to write. Wherever I travelled or lived, I brought my trusty Macbook Pro along and worked. I had fun, although I was by all accounts a workaholic. It was far from dark, but I was tired of staring at a computer screen at the end of each day.

Q12: In the past year, you’ve won a book conference scholarship and found a literary agent.  What advice would you give aspiring authors?

Writing is the ultimate endurance activity. Do not lose sight of your goal. This is for the freelancers in the house: with perseverance, you can transcend the confines of “content production” and become a true writer.

Q13: Would you consider yourself a digital nomad?


Q14: Your website,, is different from other websites, it flows nicely and it seems that after a 3 month endurance spell with your designer you came up with a product that is unique and worthwhile. Are you a perfectionist?

Yes, and my Manila design collaborator Nils Sens is also a perfectionist. (Incidentally, his partner Dr. Mendoza at InTouch Dentistry is my dentist.) Nils is currently working on the German translation of A Very Dark Game.

Q15: Just for fun: If you were asked to give up one thing – writing or poker?  

Writing is my life and I am extremely serious about it. Poker is somewhere down on the list, between hugs and hot baths.

Q16: What can we expect in the future from Damon Shulenberger?

Stay tuned to my website for blog updates related to my upcoming (December, 2014) book A Very Dark Game. And definitely watch for the mystery thriller Arisugawa Park, which has been 10 years in the making.

As for my immediate future––over the next year I expect to be on a tropical beach somewhere, working on my next book. If the Exit Bar in Boracay will allow me to do another impromptu DJ set, that will be cool. And I have been invited to start a freeform radio show on taintradio, which I plan to get up and running over the next couple months, My taste in music is pretty eclectic. For a guidepost, think Sam Rivers, early Floyd, Charlie Parker, Jimi Hendrix, Django Reinhardt, Nick Drake, Marley dub.

Q17: Any words of wisdom to freelancers out there?

Never give up––remember, writing is an art form, not a chore. Write meaningful words at all costs and let’s change the world.

**All images used in this post are courtesy of Damon Shulenberger

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