The Road to Bustoville
Lessons from Winning at Poker Tournaments for 16 Years and Ending Up Broke
Prologue — October 26th, 2008
My heart was pumping. It was just after Midnight and the second NOS energy drink was starting to kick in. After battling online for 12+ hours thru a starting field of 3605 players, I found myself as the chip leader of the Full Tilt $216 750K Guaranteed tournament with 12 players to go. But I had been in this position just four months before, holding the chip lead in the same tournament before succumbing to a few mistakes and run bad to finish in 11th place for $7200. Would today be my day to breakthrough?
The eliminations came pretty quickly and I found myself sitting in second place with five players remaining. I picked up Ace Queen Off-Suit and raised from the late position Cut-Off spot, the super aggressive chip leader re-raised me from the Small Blind (one of the two forced bets to drive the action, generally considered the worst starting position). Our chip stacks were pretty close — I had 40 times the Big Blind (the larger forced bet, typically twice the Small), the chip leader had 45 BBs, while the rest of the players were bunched around 20 BBs.
The payouts were massive. 5th place was guaranteed $31K. 4th $41.5K, 3rd $52.5K, 2nd $80K, and 1st $132.8K.
I was facing a decision — how should I play it? AQo is very strong hand for five-handed play and this player was very capable of re-raising light (with a weaker hand) here to put pressure on me. It’s a close spot with the pay jumps. I make a decision, this guy is full of shit, I’m going to jam All-In here and pick up this pot. He snap calls … he has Pocket Aces (the best starting hand in poker). Nooooooooooooo!
Still, a $31K win in a day on $900 in buy-ins would be a huge boost to my bankroll. Before seeing the flop (the first three community cards), we have an 8.48% chance of survival with a win on chop (tied pot). The flop is J83 of all different suits, our chances dwindle to 3.54%. Turn is a … 9, small glimmer of hope. River is the … 10 to give us a Queen High Straight! Holy Crap, what the hell just happened?
With that pot, we had more than half the chips in play and go onto steamroll the other players in route to victory. Wow, what an amazing feeling, to turn a $216 buy-in into $132.8K in the span of a day. I had been grinding poker hard for five years to get to that point — building small bankrolls and busting them countless times, often studying and playing up to 15 small/mid stakes ($55 and under) tournaments at a time for 70+ hours a week. I felt on top of the world a month just shy of my 29th birthday. I felt I was destined to crush it in my 30s and do big things. Bad Read.
Chapter 1 — Starting Stack
As last call beckoned on a turbulent decade in America (Watergate, Vietnam, Disco) and the World was on Edge as 52 American diplomats and citizens were being held hostage in Tehran for a crisis that would end up lasting 444 days, I was born on November 21, 1979, in Baltimore, Maryland.
I was a child of technology — my parents being two of the first people in the country to graduate with a degree in the emerging field of Computer Science (from The Ohio State University in 1969/1970). At the age of five, I would start using my first computer at home, the IBM PCjr. Games like Number Munchers, Agent USA, and Where in the World is Carmen Sandiego? would strengthen my math/critical thinking skills and foster a lifelong love for geography. My older brother (David) and I even had a HERO (Heathkit Education RObot) Jr. that would talk and play games with us. At school, I would try to replicate the trek of early American pioneers, attempting to traverse from Independence, Missouri to Oregon City via The Oregon Trail, while doing my best to fade drowning or dysentery.
I grew up in semi-rural Western Howard County Maryland (our mailing address was Sykesville, but the town was about a 5-minute drive away), in an area surrounded by cornfields and small forests. Our home was located about 25 miles West of Baltimore and 40 Miles North of Washington, DC. My father (Howard) worked as a computer systems manager for various government contractors and sub-contractors. My mother (Eileen) worked at NSA (The National Security Agency) in Ft. Meade, Maryland doing all kinds of interesting stuff that we weren’t supposed to talk about. In her spare time, she somehow managed to write or co-write and get published over 40 books ranging from computer learning books (MicroAdventures) to young adult adventure (Charisma Inc.), to romantic suspense (43 Light Street) and other genres as well. Throw in the fact that my parents had two boys that played travel sports (baseball, basketball, and soccer) and it boggles my mind how they were able to pull it all off.
As a kid, I lived for sports, with baseball being my favorite. I would watch every Orioles game on TV from the start of Spring Training (while going to the ballpark a few times each year as well) and the Cal Ripken Got Milk Growth Poster hung on my wall (alongside Eric Davis 44 Magnum and Kevin Mitchell Batman). In Middle School, my parents would drop me off at sports card shows with a friend, where we would each man a booth all day buying and selling cards. I remember once buying a 100 Count of ’90 Classic Mike Mussina Rookie Cards for like 25 cents a piece off Prodigy or one of those monthly print guides and selling them for $3 a pop. Easy Money. My Grandma Fannie (an entrepreneur herself who had run a clothing store starting in the 1950s in Warner Robbins, Georgia, with my grandfather Karl), sparked my interest in investing by sending me a few shares of stock in Disney or Coke each birthday.
While I was one of the best athletes in my class in Middle School, I soon found myself getting cut from these same sports when I got to High School. I had yet to hit my growth spurt (which wouldn’t happen until I grew 10 inches as a Freshman in college) and now all the other boys were stronger and faster than me. So, I had to find sports/activities where you could not get cut. I joined the Tennis Team, Mock Trial Team, and It’s Academic (a trivia competition between schools televised on local TV). After my Junior year, they announced they were starting an Ice Hockey team. Great, so I learned how to skate so I could join the team. Unfortunately for me, I never learned how to stop, so I would just crash into the boards to stop my momentum.
During school, I was often tired because I would stay up until 2 or 3 AM most nights playing Sid Meier’s Civilization (just so hard to quit mid-game) and since I lived out in the boonies, the Big Cheese would come bright and early each morning at 6:15 AM. I did manage to find some energy to run March Madness Brackets and Pools, and even convinced some of my teachers to wheel in a TV during class so we could watch the games.
During my years at Glenelg (High School), there were multiple driving fatalities involving students and teachers. As a community service project, my mom and I started TeenDriving.com, a website with tips and info for new drivers. The site has gone thru a few iterations and we only work on it from time to time, but I’m proud to say it’s been live for 25 years.
Chapter 2 — Chipping Up Early & Punting It Off
In the Fall of ’97, I went off to college at The University of North Carolina — Chapel Hill, living in a dorm just steps away from the Dean Dome. Since I grew up a big fan of Maryland basketball and idolizing players like Walt Williams, Joe Smith, and the Late Great Len Bias, I had already developed an animosity for Duke Basketball that fit in very nicely at UNC. When not going to class or sporting events, my suitemates and I would order in pizza and play spades tournaments (it’s safe to say I wasn’t going on many dates my Freshman year).
That year, my roommate and I started a business building desktop computers from component parts and selling them. We sold a few computers and he did most of the heavy lifting, but it was too difficult to grow. I was also buying stuff like computer DVD drives in bulk and selling them individually on eBay.
After my Freshman year, I started to notice a trend of internet stocks going crazy. Some bookseller in business for like 50+ years would announce they were going to start selling books online, and the stock would go from about $3.50 to $15 in a day (and often back to where it started a few days later).
So I decided to jump in. I sold all the Disney and Coke stock I had accumulated from my Grandma Fannie’s birthday gifts, about $2K worth, and opened a trading account with Datek.
During the dot com stock bubble, information was power. I would be in mIRC chat rooms getting stories from the news feeds and making quick decisions on what stocks I thought would get mentioned on CNBC. As stocks were pumped after getting mentioned on the network, I would exit my position. I would rarely get in right at the bottom or sell right at the top, but I had developed a pretty good low-risk system. Some picks ended up losers, but the winners more than made up for it.
Fast forward a couple of years and I’d be in the back of my business class making a trade on my laptop and then I would have to sweat it out while we were taking a quiz or doing a group project (in hindsight — probably not optimal conditions for trading). I remember one day coming back to my laptop after about 20 minutes and my account balance had increased $30K to an all-time high of $900K. Selllll!!!
Once the market started turning, I made some huge mistakes. With the volatility disappearing, I abandoned my winning strategy of starting and ending each day in cash. I bought some companies like Apple and Berkshire Hathaway with the intention of holding long-term but got impatient as they went down and sold them off. I started to get more greedy/reckless with my trades. I knew the end of the dot com boom was coming, so I made a huge bet on put options (betting against a stock) in companies like Juniper Networks, Broadcom, and Excite. If I had made the expiration dates for longer than a year, I probably would have made $2-$3 Mil. But I went for the monster score with 3–6 month expiration dates and got crushed.
In the end, I cashed out about $250K from my stock trading account. While certainly a good ROI (Return on Investment) for a $2K starting bankroll, losing over $650K from my peak definitely shook my confidence as a 21-year-old and set me back. Between paying taxes and unnecessary spending (I bought a Mercedes SLK320 Convertible in college and threw myself a pretty sweet 21st Birthday Party at the Club — dumb smart kid lol), I would predictably find myself out of money within a couple of years.
I did still attend some classes while I was day trading, although I certainly wasn’t trying to go heads-up against the toughest teachers. While I majored in business and enjoyed most of my classes (especially statistics and accounting), my favorite classes at UNC were those in the History department. I’ve always been fascinated by stories of the past and how we can use those lessons to improve our future.
I’d like to say I had learned some valuable lessons from day trading about diversification of assets and bankroll/risk management, but as wise men say … No Gamble, No Future.
Chapter 3 — Grinding It Back Up
After the dot com crash, I wasn’t sure what I wanted to do. I had an undergraduate business degree from a good school and a bunch of trading experience, so I probably should have tried to get a job on Wall St and learned how to make money with other people’s money. But for some reason, I decided to move to Arlington, Virginia and be a Real Estate Agent. Maybe I wanted a change of pace from trading in front of a computer, but overall it was not a good fit for me. This was in 2001–2004, before the housing meltdown. I worked pretty much exclusively as a buyer’s agent with first time home buyers. The market was out of control and we would go in with an offer/escalation clause for 25K over asking and get blown out of the water by an all-cash 100K over asking offer. How could this not end well?
While not closing many real estate deals, I found myself with a lot of free time. Poker (specifically No-Limit Texas Hold’em) was gaining popularity on ESPN as they were showing the player’s hole cards (starting hands) for the first time. An accountant from Tennessee named Chris Moneymaker would soon turn an $86 online entry on PokerStars (a popular poker software/game client) into winning the 2003 WSOP (World Series of Poker) $10K Buy-in Main Event for $2.5 Million. The Poker Boom was On.
My friend Vic started hosted a weekly small buy-in game at his place. When I got home, I would crank up my TIVO and watch the latest episode of the World Poker Tour on the Travel Channel. I soon found myself playing on PokerStars and doing pretty well from the start. Back then, nobody knew what they were doing (and neither did I really), and there weren’t much-published materials on online poker, so I kind of had to figure it out for myself thru trial and error. I found initial success in turbos (faster tournaments that reward pre-flop aggression) and satellites (smaller buy-in tournaments that award tickets to larger buy-in tournaments).
After the 2003 WSOP, PokerStars announced they were going to host the PokerStars Caribbean Adventure on a cruise ship in January of 2004. That sounded pretty cool, so I played a bunch of satellites to the event and eventually won my ticket in a Double Shootout (a format where you have to win your table, then beat another table full of round 1 winners). The package included a $7500 entry to the event, cruise accommodations, and $1K cash for travel expenses. The tournament (my first live one ever) had 221 entries and I managed to outlast 193 of them over three days. Unfortunately, that made me the bubble boy and I finished in 28th place for zero dollars (27th got $11605). After busting the tournament, I did hit a Four of a Kind in Let it Ride for $1500 while hanging out at a table with Chris Moneymaker’s dad, so all was not lost. Live Poker was very stressful and tiring, so I was glad to get home and playing online again in Arlington.
In the spring of 2004, I felt the West Coast calling. I moved to San Diego to work as a fundraiser for the DNC/Grassroots Campaigns during the ill-fated John Kerry Campaign. That was a pretty tough job as you were hitting people up for money as they were coming out of grocery stores like Whole Foods or Gelson’s. Most of the people just blew you off. It was commission based, so some days I made less than it cost to put my Golden Retriever (Jordan) into doggy daycare.
After spending the last two weeks of the campaign canvassing around neighborhoods in Denver (Colorado was a swing state) while freezing my butt off, I returned to Sunny San Diego to get my poker grind on. Over the next couple years, I played full-time, putting a lot of time into improving my game and grinding small stakes under the name tarheelkid23 on PokerStars, tarheelkid on Full Tilt, and similar names on other sites. While I was making some money, I wasn’t making enough, so I constantly found myself broke or near broke. I moved up to Los Angeles in 2006 to be closer to family (my brother had moved to Santa Monica a few years earlier) and to give myself more Live Poker options.
In early 2007, I got into the startup scene in Santa Monica, working first to help launch Twiistup (an early Silicon Beach networking event) and then managing a virtual team for EduFire (an online platform for connecting teachers and students). While working on the startups, I was still grinding poker on the side, playing a lot of PokerStars 180 Man Sit-n-Go Turbos and Full Tilt 90 Man KOs (where you get a bounty for each person you knockout) to build up my bankroll.
Things started to go my way in late 2007/early 2008. I won the Bodog Sunday 100K for $25K along with multiple 5-figure scores on PokerStars and Intertops. I also found a new website/community called Part-Time Poker Staking (a site way ahead of its time that would unfortunately not survive subsequent events). On Part-Time, I could buy pieces (a percentage) of a player in a tournament or package of tournaments and offer full stakes to players as well. The site managed the whole process with features for reporting results, bankroll tracking, and calculating makeup (a method to align the interests of the player and investor).
After my breakout win for $132K in October 2008, I now had a bankroll to build my staking business. For the next two and a half years, I would continue to play, but the majority of my time was spent on the staking side. Often times I would back up to 40 players a time, working with players to develop effective strategies to get them from low states to mid stakes. While the business was super swingy, I really enjoyed it and had a few big staking scores (including a $100K+ score in a Full Tilt Online Poker Series) that made it profitable.
I was married (I had met my wife two and half years earlier at a UNC alumni event in Santa Monica) in October of 2009 in a beautiful ceremony at the Red Rock Resort in Las Vegas. Things were going well with online poker. But sometimes the heater has to come to an end.
Chapter 4 — Bad Beats and Bad Decisions
On Friday April 15, 2011 (a day that become known as Black Friday in the poker community), the US Department of Justice unsealed an indictment against the three biggest players in the US Market (PokerStars, Full Tilt, and Absolute/Ultimate Bet) accusing them of bank fraud, money laundering, and violating the Unlawful Internet Gambling Enforcement Act of 2006. While the UIGEA didn’t make online poker illegal in the US, it did forbid businesses from making financial transactions to gambling websites, making it very difficult for customers to deposit and withdraw funds. In response to the UIGEA, some sites like Party Poker decided to leave the US market. Others like PokerStars and Full Tilt stayed in the grey area and used workarounds and offshore payment processors to fund transactions.
In response to the Black Friday indictments, PokerStars and Full Tilt immediately pulled out of the market (Absolute/UB soon followed). The US was by far home to the most online poker players, so the whole industry was brought to a screeching halt. Hundreds of Millions in customer account funds were frozen by the US government and it turned out that Full Tilt had been using the money in players’ accounts to fund operations and take profits and was short over $300 Million. Some players had hundreds of thousands or more tied up for years and others never got all their money back — it was a mess.
After Black Friday (I had about $20K frozen in various accounts), I was faced with a choice. It didn’t seem like online poker was coming back to the US anytime soon. I could move to Mexico or Canada (as many American poker refugees would soon choose to do) to continue playing and staking, but I didn’t think that was a good option with my marriage and the state of online poker. I would take an occasional road trip down to Rosarito, Mexico over the next couple years to play a big series online, but the options left to play online in the US were pretty depressing. Looking back, this would have been a great time to see the writing on the wall and do something a little less insane with my life, but instead, we opted for door #3 — becoming a Live Poker Pro.
For my first 8 years in poker, I had played live tournaments only occasionally. I would win a trip package online to a place like Aruba or St. Kitts and go punt a $5K entry in the islands. Since moving to LA in 2006, I had played one or two live tournaments a month, recently taking second in a $125 Turbo Event at Commerce Casino for $52K in February of 2011. So, I decided to go for it. And it started out really well after Black Friday, chopping a $220 buy-in for $55K and taking second in the Cal State Poker Championship $2575 Main Event for $94K two weeks later in May 2011. I had a huge staking score in a live tournament in Oklahoma later that year — I started to think this Live Poker thing wasn’t too bad.
For a pro, poker tournaments are like playing the lotto with an edge, over and over. For your $1100 entry buy-in, $100 goes to the house as rake (for a smaller buy-in, this could be 20–25% of the total amount) to run the tournament, while $1000 goes to the prize pool. Typically, payouts are given to the last 10–15% of the field remaining (a min-cash may be 1.5X or 2X the buy-in, while first place could be 100X or more). Players are given a starting stack of tournament chips (let’s say 25K). Throughout the tournament you are (hopefully) accumulating chips and your stack is increasing in equity of the prize pool. But unlike cash games (where you can leave anytime you want), you can’t cash out your full equity in a tournament until you win or chop (make a deal with other players at the final table) the prize pool. So, it’s very possible to build your stack from 25K to 500K (your stack is now worth $20K to use a simple method of calculation), get into a hand that is an unavoidable 50/50 coin flip situation, and you lose and bust for a $4K payout. This happens a lot. You are constantly building equity and not realizing it — but occasionally you keep building equity and win/chop the tournament
Tourney payouts are extremely top heavy. For example, the WSOP $10K Main Event had 7,874 entries last year for a total prize pool (after rake) of $74 Million and change. The Final Table of 9 players received 38% of the entire prize pool. Your whole year (and possibly your career) could come down to a flip deep in a big tournament. In the long run, if a pro puts in enough volume and keeps making +Ev (Expected Value) decisions, they should be profitable. In reality, the long run can be a long time.
Poker is both a game of skill and luck. How much of each? It’s impossible to calculate. While you can control your actions (how much to bet, when to fold, when to call, etc.) and what games to play, so much is out of our control as poker players. Between flips, coolers (running a really good hand into a better hand), starting hand distribution, table draw, and the actions of other players, there is so much left to the poker gods. And even if we manage to navigate through 99% of the field, we may still be pretty tilted (super frustrated) to finish 10th in a 1000 person field just on the cusp of big money. It’s a tough way to make an easy living!
While I was playing the same game (No-Limit Texas Hold’em) live as I was online, they are in fact two entirely different games. Online I could use stats collected in a HUD (Heads-Up Display) to make effective data-driven decisions in seconds with action pending on multiple tables. Live, I had to be my own HUD, and collect all the information manually thru observation. Online a hand may take just a few seconds up to a couple of minutes, while live a hand can take from two minutes up to five minutes or longer. An online tournament with 5000 entrants might be done in 12–15 hours, a live version could take a week.
At the time, I was living in Studio City (in the San Fernando Valley). I would have to battle traffic (up to an hour and a half each way) to get to the casino, so I was often on tilt before I even started. While I enjoyed getting to meet other players from all walks of life and hearing their stories, there are also lots of players that can annoy the crap out of you (casinos do tend to attract their fair share of scumbags and miserable people).
Patience, a skill I had never really developed online, is crucial in live tournaments. To give yourself the best chance of success, you are going to have to bring your A game for 10–12 hours a day over multiple days. As you get deeper in the tournament, decisions have more and more equity on the line. You have to battle not just your opponents, but also sleep deprivation and mental exhaustion. Making mistakes and costing yourself the chance to win hundreds of thousands or millions of dollars is devastating. As I describe it, it does sound pretty crazy to pursue this type of game for a living, but there is huge upside in the ability to win life-changing money.
After the initial success as a Live Pro, I started to struggle. The slow pace, grueling physical/mental nature, and low volume made it very tough to grind thru the downswings. After playing well for what can be months or longer at a time and just losing every day, it’s very easy to question whether you were any good in the first place. You begin doubting your confidence and start to play passively, which is a really hard way to win at poker tournaments. You do this day after day, and you’re going to get worn down. Once you start running out of money and have to ship a tournament to pay the bills, you’re in trouble.
Over the next couple of years, I eked out a small profit each year, but was making way less than minimum wage with all the hours I was putting in. I tried cash games and had some success, but just wasn’t passionate enough about the format to put in the study time and volume required to succeed. I traveled to a few places to play tournaments, but the double hit of LA and travel expenses was difficult to overcome. Some pros travel the circuit without a home — living out of a suitcase in places like Cherokee, NC, and Durant, OK. I do think this is a smart approach, but a tough lifestyle to maintain. You may ask why I didn’t just quit? It’s hard to give up on a dream when you feel so close (but in reality may not be close at all).
In late 2013, the Bicycle Casino in LA decided to launch a new concept, the Quantum Reload. They wanted to create a tourney where you could take a small buy-in like $240 and potentially win over $200,000. They would have 10 or so starting days with two sessions a day, so you had ample chances to qualify for Day 2. If you didn’t qualify on or didn’t want to bother with Day 1, you could buy-in directly for Day 2 for a higher buy-in/rake amount and get an average Day 2 stack (often 10X-15X your starting stack). At first, I liked the idea. This would give me more chances to build stacks against weaker players. The problem is that no matter how many chances you have to qualify for Day 2, when you’re constantly playing fields with 5K+ entries that can take up to two weeks to complete, you’re going to go broke in the long-run unless you hit the Mega Million Balls and ship a tournament. One time, I managed to fire 17 bullets (entries) into one Quantum tournament without cashing, quite an accomplishment. And by the time they added the ability to bust and re-enter on Day 2, it was beginning to feel like a rake tarp. While I don’t expect much from a casino other than maximizing profits, I do think they have a responsibility to protect the long-term interests of the game and not suck out every last dollar of rake from the system. But I did decide to play these super lottos for a living, so I have to hold myself responsible for my poor decisions.
Even during my online days, I would have issues with sleep. It’s just really hard to shut the brain down and relax after being so intensely focused for hours upon hours. Hands would replay in my mind in an endless loop. When you’re on a downswing and on the verge of going broke, the anxiety can be debilitating. I tried stuff like Ambien, Klonopin, and Trazodone to get to sleep. Sometimes they knocked me out but would leave me too groggy the next day to think. Many days I could not make it out of bed. When you don’t have the energy to improve your game and grind, you’re going to get crushed. Sleep is so important, without it we are pretty much drawing dead.
By late 2014, my marriage was heading for the showers. Relationships and playing poker are two very difficult things to balance. It’s almost impossible for a downswing not to affect your personal life and day to day happiness. By that point, I decided I’d had enough of being a full-time poker player, so I went back to school at UCLA-Extension to complete a certificate program in Technical Project Management. After completing the program in a year and playing part-time, I landed an IT Consulting Job thru one of my brother’s connections. The job was interesting (working on IoT/Big Data initiatives) and I enjoyed being in an office every day with some really cool colleagues, but after 14 months decided I wanted to travel and give being a poker pro one more shot (you would have thought I would have known better by this point — but poker players can be pretty stubborn sometimes and don’t like to fold easily).
Over the past two years, things haven’t really turned out as I planned. While I do think I worked hard enough to potentially succeed, I also could have put in more time away from the table improving my game. In the end, living in LA and not making enough/spending too much did me in. Spending based on what you made in the past or expect to make is a really bad idea because past results do not guarantee anything in poker. I also made some bad choices on traveling for poker on too small a bankroll and not grinding smaller stakes online where I could get in more volume.
While I’ve never had a losing year playing poker (which is possible for any live tourney pro) and had some really good years, I’ve also had years where I made $3/Hr (and in the red when factoring in expenses). The unpredictable nature of poker income (especially in tournaments) makes it really difficult to play for a living. I have huge respect for the tourney and cash grinders who have the discipline and work ethic required to make a living at it year after year. While I do think that live poker tournaments make for a great hobby due to their social/competitive nature and that you can improve your game and make money from them, grinding them 5–6+ days a week as a job is a whole different animal.
Going busto again is certainly humbling. Although I may be liferoll/bankroll challenged at the moment, I am feeling good overall and important things are starting to come in focus. In my 20s and early 30s, I was very much obsessed with hitting the big score and striking it rich. Now I’m starting to think that success can be measured in different ways — i.e. the impact you can have on other people’s lives. My sleep is improving (meditation and journaling help with brain data overflow) and I’m ready to get back and start grinding again for my life.
Chapter 5 — Finding a Balanced Strategy
Pro poker players are very much entrepreneurs. We have to decide not only what games/formats to play and where to play them, but also how to spend our time away from the table (preparing for a session, studying, planning travel, researching opponents, recovery time, etc.). We are constantly adjusting our game and overall strategy to maximize profits and lower the risk of going broke.
After 16 years of playing poker tournaments (8 mainly online, 8 live), I hope I’ve been able to learn a few things that may be helpful to other poker players and entrepreneurs. Q the Tips:
Don’t Go All-In
Going All-In is a strong move, you’re pushing all of your resources forward into battle. But when you’re All-In, you may also be at risk. The idea that entrepreneurs should have to risk everything by not taking a salary while building a business doesn’t make much sense to me. Failure rates among startups are huge (upwards of 90%) — the pressure is even tougher if you can’t pay the rent. It’s almost impossible to make optimal decisions under these conditions. Going broke can be a disaster — you can easily lose a decade of your life trying to recover from a bad decision or series of decisions.
If you don’t have money saved up and are raising seed capital via Friends/Family, Equity Crowdfunding, or Angel Investors, negotiate a salary that will allow you to stay focused on the business. In poker, good bankroll management is one of the most important keys to success. While the media likes to hype unicorn startups with billion-dollar valuations, I do think there is value in growing a business slowly and being cautious with business and personal expenses (you may have to sacrifice some luxuries to get you where you want to go). If your business starts to have success, begin selling off equity pieces at regular intervals and diversify your asset portfolio.
Punts Happen
As a pro poker player, I try to bring my best effort every day. But as a human, for whatever reason, some days I just can’t bring it. I might get tired and lose focus and make a huge mistake that costs me heaps of equity. But once the punt is done, it’s done. If you still have chips left in the tournament, the past is irrelevant (other than as a learning lesson for later), and you have to focus on the present moment.
Poker players often like to talk about their bad beats. But, what we rarely talk about is the two or three hands we screwed up prior to get us to that point of vulnerability. Life, like poker, is a game of imperfect information. No matter how much we learn from our mistakes, we’re bound to make new ones. Own up to your mistakes, embrace them. Since mistakes are inevitable, it is pointless to get frustrated by them. Improve your process, stay positive, and try to make fewer mistakes than your opponents.
Plan to Adjust Plans
In my favorite TV show growing up, Colonel John “Hannibal” Smith would come up with a sick plan, they would run a pretty cool montage with music, blow torches, and other stuff, and then the A-Team would execute flawlessly for the most part (and somehow use machine guns and grenades and no one would die — but that’s another story). As someone who spent much of his 20s and 30s thinking about the future, it’s never turned out like I imagined (which I think is a good thing). It’s great to have a general plan of where you’re heading, but be flexible on how to get there and continually update the plan as you learn and discover more. That being said, I do love it when a plan comes together.
Get Locked-In
In poker, there is a huge difference between playing your A game and just showing up. When you are locked-in, you’re not thinking about what you’re getting Mom for her birthday or trying to make sense of the Thrones finale you saw last Sunday. You are 100% focused on the task right in front of you, collecting information and making +Ev decisions.
Planning/expecting to get lucky and bink a tournament is a terrible strategy. The best poker players in the world are the ones that work the hardest, both on the felt and away from it. Figure out what’s most important to you and then drive all your energy and decisions towards that goal. As entrepreneurs, we are given almost unlimited freedom and so many options on how to use our time. Build structure in an unstructured world by creating daily routines and time blocking activities. Pile all your non-essential activities and distractions to the end of the day.
Write Your Story
While my story is unique as everyone’s is, I don’t consider it that remarkable in the poker world. Others have won and lost 10 times or more what I have playing in high stakes tournaments and cash games. In a game where showing emotion at the table can be a sign of weakness, I can only imagine the roller coaster of emotions for those individuals.
As poker players and entrepreneurs, we have a lot of stuff bouncing around in our heads. Try your best every day to get that stuff out of your head — whether that’s in the form of notes on your phone, journaling in a notebook or online, discussing your thoughts with family and friends or seeing a therapist.
Spend time reading or listening to stories about people that inspire you. Some of my favorites are Richard Branson: Losing My Virginity, Nelson Mandela: Long Walk to Freedom, and Ben Franklin: An American Life. I encourage other poker players and entrepreneurs to write out their stories (being honest with the good and bad). Even if you don’t throw it out to the world like me, I think there is huge value in recording your history and organizing your motivations.
Chapter 6 — Firing the Next Bullet
Starting about a year ago, I began teaching my girlfriend (Diana) how to play poker online. I figured if it was going to work in the long-run, she would have to understand the joy and pain that comes with poker. Seeing the game thru the eyes of a brand new player brought back much of my love for the game — the excitement of running deep in a live tournament and getting in the money for the first time, the agony of a fish (terrible player) gutting your dreams, the exhilaration of hitting your card on the river to stay alive. Even with all the ups and downs, I still consider poker tournaments to be a beautiful thing. How often in sports or most things in life do you get to fail so often for 16 years and still be in the game?
One of the things that makes poker great is that anyone can buy-in and win (if luck is on their side). Poker tournaments definitely take the great unknown to the next level. For no matter how small your bankroll is, you are usually just one or two wins away from where you want to be.
Earlier this year I started to get into Poker Channels on Twitch (props to MattStaples, ALLinPav, CrazySixes, Bill Perkins/TL Crew, and all the amazing streamers working to grow the game). I’ve started to play some online again myself and as I run deep in a small buy-in tournament and get closer to the final table, that feeling of anticipation and nervous energy brings me back to my days of discovering the game for the first time.
Between politicians, corporations, and special interests, the voice of the online poker player in America has been drowned out over the past decade plus. The fact that you have to play one of America’s favorite pastimes in 2019 on unregulated sites using software that is worse than what I started with in 2003, seems kinda well un-American. The federal government doesn’t appear inclined to do much. I hope states like Nevada, New Jersey, Pennsylvania, and California take the lead in creating a regulated shared pool market that enables a fair playing field for customers and promotes innovation from established and new businesses (located in both the US and abroad). I’m glad to see that Sports Betting and Daily Fantasy Sports are starting to gain more mainstream acceptance. Eight years after Black Friday, it’s time for online poker to be able to come home to America as well.
While my family has some reservations about poker (which is pretty understandable considering my current situation), they have always been supportive of me. I’m fortunate to have friends that believe in me and have helped me along the way. I certainly recognize how lucky I am to have been born into upper-middle-class America with parents that exposed me to technology at an early age. Most people in the US and Around the World don’t have these types of opportunities and this is something that I do not take for granted.
At its’ core, poker is an adversarial game where you utilize strategy (which may include deception) to take resources from your neighbors. While I have made incredible friends from poker, at the table they are my enemy. I have wrestled with the question for many years — should I be doing more with my life than playing cards for money? I’m still trying to figure out the answer, but I do think that living life by itself can be enough, as long as you treat others with respect and are in general not a shitty person. But for other entrepreneurs like myself, who are programmed/driven to take risks and challenge the status quo, we must do what it takes to turn our visions into reality.
So, after 13 years I’m saying goodbye to LA and hitching the proverbial wagon and heading Northeast with Diana to Vegas (or at least moving our stuff into storage in Vegas, we’ll figure out the rest after the WSOP). While my friends and poker players (both professional and recreational) from around the world are busy preparing for the 50th Anniversary of The World Series of Poker that starts next week at the soon to be demolished (for a baseball stadium or Hyperloop terminal, who knows) Rio Hotel & Casino, I’m taking a more measured approach. I’ll still sell action and play a few big weekend events like the Big Fifty and hope to be able to play in the $10K Main Event which had a first prize last year of $8.8 Million (I’ve played it eight times so far and have yet to cash, but I don’t count the first four times as I was just an internet kid clicking buttons). I’ll play some online sessions in the evenings and work to improve at poker, but I want to focus a good chunk of my energy on learning a new game.
As we move to Vegas, a city built on dreams and imagination, I want to take my poker grinder mentality and see if I can build something myself. I think the model for entrepreneurship in America is flawed. Great founders and ideas don’t just come from Harvard/Stanford dropouts and Silicon Valley. I believe there are tons of under-the-radar entrepreneurs who could do amazing things if given the right tools and resources. I hope to be able to help give them their shot.
As I approach 40 later this year and close a chapter on my life and start a new one, I’ve decided to do a career reboot and wipe the slate clean. So, I’d like to say good game/nice run to tarheelkid23 and wish best of luck to BuckBox (thx for the name Nik!). I still consider myself very much a work in progress with a lot left to learn — just a guy trying to solve this game we call life. But for all the close calls and massive fails, I’m still an optimist who believes in the same dreams as a kid from Maryland — to win the World Series and make My Mark on the World. Will success be in the cards for me? Only time will tell — but I’m hoping to win the flip.
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