It’s been just about four years since my first post here, just before my 49th birthday in 2010. So at the end of this week I turn 53. I’m still not making a living playing poker, but as I wrote in my first article for PokerNews.com earlier this year, that’s not an easy task, mathematically. (On a related subject, there’s an interesting long thread on 2+2 that I just ran across yesterday).

I’ve always been interested in games, but due to disposition and a lack of money in our family, nobody I knew was ever involved in gambling or ‘gaming,’ so I never played poker until I was in my early 20s, when I hosted a five-card draw game at my house where the guys I worked with in a book warehouse got together after work once in a while after our weekly payday for some nickel-ante cash games. No casinos in Oregon at the time (or much of anywhere else in the West outside Nevada since this was before the Indian Gaming Regulatory Act). I hadn’t ever seen poker played outside of movies and TV. But I liked the social aspect of it, and I was just as enthusiastic about it as I had been a couple years earlier when I set up spreadsheets to manage a baseball fantasy league back at the beginning of the craze, even though I have never had any interest in sports. After I moved out of Eugene, I didn’t play poker again for nearly twenty years.

The Moneymaker book completely missed me. I was completely oblivious to Texas Hold’em and tournaments though I’d worked on some prototype online video poker and casino games in the late ’90s. Didn’t watch sports, didn’t see ads for the online sites, just went my own way until I was talking games at a holiday party with the husband of one of my cousins, and he invited me to a little bi-weekly $30 home tournament. I played infrequently through most of 2008, and didn’t cash in any of the one or two-table events until the spring of 2009. By that time, while I’d been working as a freelance programmer for over a decade, had written several programming and multimedia development books, and gave presentations at national conferences from time to time, I hadn’t had a steady paycheck for more than two years, and I had a fair amount of time on my hands, so I’d set up accounts online, playing qualifiers to live events (I ran across an email to a friend mentioning I’d made it to 77th place in a 7,500 player field on PokerStars in May 2009). I started winning in the home game. I took 2nd in a 200 entry Full Tilt tournament in July 2010 for nearly a 40x prize. But I wasn’t that good and kept shooting for big money which increased my variance more than I knew. And I was broke, so when I cashed out and then ran my online bankroll down, there was no way to prime the pump.

As a self-improvement project in late 2008, I’d started learning iOS programming, eventually releasing a game on July 4th weekend in 2009 (you can still get the free version). As my second act, I started doing something poker-related, mostly to have something to show to prospective employers. I wrote a tool that an accomplished user could manipulate while their iPhone was in their pocket, which would give audio feedback on the hand’s strength. So you could hit a button that specified there were 9 players, tell it you had an ace and a king and that they were suited, and it would repeat back the particulars and that it was a 22% favorite against eight random hands all in, with a 2% chance to tie, all without anyone knowing you had that info, assuming you hadn’t forgotten your headphones. First, I had to generate the hand equities, so I wrote a program to play out half a million hands between two players and twelve players (just to be thorough). Not really marketable, but an entertaining exercise.

I worked on that, off and on with breaks for paying projects, until the summer of 2010. I’d been following more and more poker news, and as the World Series of Poker got under way that summer, I kept an eye on the reports. Early in the series, skimming over the list of final tableists, I ran across a name that was very familiar to me from my work as a programmer, as someone I’d first met a decade earlier at conferences developing  extensions to the software tools I used. I hadn’t talked to him for several years, and I wasn’t sure it was the same guy, but a quick email led to a confirmation that it was, indeed, the same Tomer Berda I knew who’d placed fifth in a $1,500 NLHE event. I had no money, but I did have some frequent flier miles and went down to Las Vegas to have lunch, catch up, talk about my goofy tool, and learn a lot about playing poker for a living. Then I did my best to sweat Tomer from afar through the rest of the series, where he had a tough time of it until the day the Main Event began, when a 1,941 player field in the last preliminary event turned it into a four-day affair, which he won. I was hooked. Not because it looked like easy money or because I thought I’d win big early on, but because at that point anything looked good as an option for making a little money, even something my family and my wife considered degenerate gambling.

I played (necessarily) small stakes online tournaments, with and a lot of satellites to live events like the Irish Open, then went up to Seattle to watch Tomer grind some games and play $1K pots on $25/$50 cash tables. I was doing a self-analysis of pretty much every tournament I played, with a write-up of at least a sentence or two (sometimes much longer) here on the blog (shout out to Brad Smith, one of my other former multimedia colleagues, for encouraging me to put it together). Despite having some excellent advice, I wasn’t playing smart, playing bigger than I was bankrolled, and then Black Friday happened in the spring of 2011.

I’d played a few small tournaments at the local Portland poker clubs before Black Friday, first at the daddy of the clubs: Portland Players Club, the late Aces Players Club, then Encore Club in February. After accounts were closed on PokerStars and Full Tilt, I started making the rounds a bit more often, spiking first place in an 80-player freeroll in early May on my first time back at PPC after a year. Our home game season was drawing to a close. I’d been in the lead for Player of the Year for the middle of the season, in the winter, but by spring I’d dropped to third place in the running for a seat in a 2011 WSOP side event, then needed everything to run my way in the season ender in order to make enough points to win. They didn’t. My first month of concentrating on live play turned out about even.

The end of access to the big online poker sites in the US was good business to the poker clubs, which started to ramp up their game selections. I played my first live $10K guarantee just over a month after Black Friday, my second a week later, and cashed for 7th place in a 141-entry $10K (my fourth) by the two-month mark. My recording here started to go down. I kept notes as well as I could during live games at the time, but found it difficult to follow action as well as I wanted to when I was typing about the last hand played.

Played poker for the first time in a casino on a vacation trip to the Washington beach that summer. That might seem odd for someone who’s been working towards a life of poker, but I hadn’t ever been in a casino before I was in my mid-forties, and that was only because  I did a presentation on podcasting in Vegas, and they’d put me up at the Rio. Stayed at the Stratosphere one night a couple years later before my wife and my parents headed off for a trip to Bryce, Zion, and the Grand Canyon. Didn’t have any time to play when I went down to visit Tomer on a one-day trip. So it was a new experience.

Luxury view at the Stratosphere

Got back home, took second place in a 140-player invitational at Encore for winners of their daily tournaments, then went into a long slump through the summer, as I was working my way up to my 50th birthday, trying to steamroll my way to the European Poker Tour Prauge event that ran through December. A rare business trip to Boston gave me a chance to see (and fail at) Foxwoods, which was a bit bigger than the little coastal casino in Washington state or Spirit Mountain here in Oregon, where I’d just played a tournament. It wasn’t until almost exactly three years ago that I had my first big win, in the Encore $10K. Only 75 players, but good for more than $4,000 in profit.

Regrettably, while I’d learned a lot about poker, I hadn’t learned much about bankroll management. The $4K represented a big chunk of money to someone without a job, but I was kind of fixated on running it up for a trip to Prague. and blew it on a last-ditch (with my 50th just a couple weeks away) effort by flying down to Vegas within a couple hours of my win, regging for a Venetian Deepstack Extravaganza Main Event, and busting out after about five hours.

For a short time, my Encore win was the largest prize in regularly-scheduled Portland events, because most of them ended in deals.

It was a few months before I had another four-figure cash (in fact, nothing in-between November 2011 and February 2012 over $200) and I took off to Vegas again to catch part of the DSE I at the Venetian without any success. In the spring, Tomer invited me down to play a WSOP Partners tournament with him, and I started putting together plans for a longer trip. Did some more trips out of town, first to the Tulalip Poker Pro Challenge in March, then my first trip out to Pendleton for the Wildhorse Spring Poker Round-Up, neither of which was successful. Met Brad—who’d read my blog—over the table; he and his friend Steve have become my live-play poker buddies.

That summer was the beginning of some of the deep number crunching I’ve been doing, based on in the money percentages, prizes, and volume for tournament players. Mostly it’s been an attempt to determine whether or not I can actually make a living playing poker as opposed to just having it as one of my revenue streams.

Drove down to Vegas for a two-week stay in the summer of 2012 and—apart from a bounty I took in a game at the Venetian—bricked 21 live tournaments. I owe big to my fellow Portland poker player/Reed alum Mark who put me up in his condo the first week and to Tomer, who paid for dinner almost every night, which kept down the living expenses, at least. Played my first WSOP event, sitting down to a starting table with Ivan Demidov and Keven Stammen. And that Partners event that Tomer and I played? Well it wasn’t me who lost all our chips.

That fall was the night I won a seat into Wildhorse’s Fall Main Event a few hours before my wife had a heart attack at her sister’s house and had to have emergency surgery. The cash came in handy at the emergency room.

The spring of 2013 was pretty uneventful, until a trip to Spirit Mountain in May perked things up with my first cash in a tournament outside of Portland (I’d been down to Lincoln City in February for the first Deepstacks Poker Tour series there, as well as back out to Pendleton, with no results at either). Made a couple short trips to Vegas that summer, scoring my first cash outside of Oregon in a small Caesars Palace tournament and busting out of the first WSOP Turbo tournament in record time when I tossed in the wrong chip and had to follow through on my mis-click to stay viable. I put in a fair amount of time on Carbon Poker that summer, as well, doing reasonably well in 6-Max and Deepstack Turbo events and min-cashing in a $70K guarantee Poker Maximus event.

Two top-three finishes in Aces Players Club $10K events within a month sent me back down south in September 2013, where I had my first significant cash in Las Vegas at a small Caesars Palace Seniors tournament. A month later, I won a daily Venetian bounty tournament after changing my travel plans when Grand Sierra Resort in Reno cancelled most of a series when the first event fell far short of the guarantee. A couple weeks later, I min-cashed the Main Event at the second DSPT series on the coast, where I met Toma Barber, who was living in Vegas but is now a regular here in Portland. After another deep run in a Final Table $10K and an incredibly bad read in the first $2,000 High Roller tournament at the Fall Wildhorse series, I popped down to San Diego in December for my first (and only, so far) WSOP Circuit events.

Won another Final Table $10K in January this year and started playing on Bovada the same month (taking in my best-ever single-tournament ROI in mid-February), then went into a two-month slump where I didn’t win anything big in actual dollar value. I made it into the money in a Bovada $100K guarantee with over 1,200 entries, but nothing major until a second place at DSPT’s third series at Chinook Winds, in the HORSE tournament. Meanwhile, I tentatively passed an article to Martin Harris at PokerNews.com, which started me on the path to a lucrative sideline of poker writing as well as some vitriol and condemnation online.

My mother died in May, and I took some solace in the sort of meditative state I, at least, get into when I’m playing poker. I’d just taken second in an Encore $7K guarantee a couple days earlier, then I won a 65-player Bovada 6-Max, and topped that off with 3rd place in a $20K at Final Table and a fifth at an Encore Club $40K in consecutive weeks. Went back down to Vegas a couple times during the season, skipping the big buy-in tournaments and cashing small at Planet Hollywood and the Orleans. Got busted out of a tournament at the Wynn by a billionaire. Won a satellite seat into an $800K guarantee tournament at the Venetian and busted, then played a tournament at the Flamingo where I was all-in almost every hand.

The fall’s been pretty thin. I had some deep runs in the daily Bovada $5K tournaments (fourth, sixth, and twentieth in fields between 400 and 500), but had several long stretches without a cash through the fall.

The last week of November was pretty good, though, with seven profits in 13 tournaments, just missing the final table in a $10K at Final Table and in a $15K bounty tournament at Encore on consecutive nights, a couple of successful Bovada Quadruple Up PLO8 games, and a win in an 11-player Big O tournament at Portland Players Club, I even soon the home game where I hardly ever cash any more.

Looking forward this week to a couple of events at the 2Pair Poker Tour series in Eugene. It ain’t Prague, but it’s going to have to do for this year.