Capture the Flag With Dan O’Brien

Las Vegas-based poker pro Dan O’Brien is one of the game’s most consistent grinders. Over the years playing tournaments, he has amassed 114 cashes and roughly $2.7 million in earnings.

When he’s not traveling for tournaments, O’Brien plays cash games—anything from $5-$10 to $10-$25 no-limit hold’em can be considered his regular game. The 30-year-old Long Island native plans to be playing more cash in the future, as he wants to be traveling a bit less.

Card Player had the chance to speak with O’Brien about his poker career, as well as pick his brain about some basic cash-game strategy that would be applicable for anyone just beginning to try and get their feet wet in the smaller-stakes hold’em games.

Brian Pempus: Can you talk about your history with cash games? Did you start out as a cash game player or as a tournament player?

Dan O’Brien: I started playing cash games in my dorm lounge and then at other dorms at the University of Maryland College Park. I then moved to small cash games online and played about 95 percent cash games online until I final tabled my first World Series of Poker event in 2008.

BP: What was it about cash games that attracted you to them in the first place?

DO: I didn’t know any better, and it just seemed like the way I’d seen the game played in movies. Once we started throwing in some single-table tournaments in school, it became clear that I could make more playing cash games with less variance.

BP: Did you feel like the deeper-stacked structure also suited you better?

DO: The structure of cash games certainly allows for far more complexity and is more difficult to standardize with computer-assisted math. When I started, I just enjoyed being able to put more pressure on people with more money at stake, but now, as someone who doesn’t want to study and learn every chart and put in thousands of hours playing tournament poker, it’s hard to keep up with the world’s best tournament players and cash games allow for more creativity and on the spot decision making.

BP: What were some of the mistakes you made when you first started playing cash?

DO: I was raising too many hands from early position and not raising enough from later positions. I didn’t understand entirely the importance of board texture and when it made sense to run bigger bluffs. A lot of people ask how often they should be bluffing, but they don’t understand the moments when it is most profitable and wind up bluffing in nonsensical spots where it’s far better to just give up and move on to the next hand.

BP: Can you give some examples of nonsensical spots?

DO: I’ve seen people check-raise an A-A-x-x board and get called by what is always an ace, and then continue the bluff with a small river bet that has no hope of working. It seems that people sometimes just decide to bluff and don’t react to new information.

BP: Can you give any examples of situations where an under-bet bluff on the river is a good play?

DO: There are situations where it’s fairly evident that both you and your opponent are weak, where a smaller river bluff will make sense because you’d likely value bet that size and your opponent doesn’t have much to call you with. This will give you a better price on your bluff, but also a better price for your opponent to look you up, so it needs to be used wisely.

BP: Can you talk about some instances where you have a good read on a player that their overbets are almost always bluffs? Is this a rare tendency among cash game players?

DO: People typically don’t overbet the pot in general, but there are certainly players who use different bluff sizes for value bets and bluffs. Oftentimes, it is larger value bets and smaller bluffs since people aren’t comfortable risking as much without a quality hand, but some players go the other way and are consistently bluffing bigger than they’d ever value bet.

BP: How important is it to get a general sense of what a player is capable of with regards to that?

DO: It’s very important to gather as much information as possible regarding what your opponent is capable of in order to properly assess his range of holdings in a variety of situations. There are some players that are almost never bluffing in a given set of circumstances, while some others are bluffing with a high frequency under the exact same set of circumstances.

BP: Would you say that over the past five or six years people have been drifting more toward one way over the other? Would you say people have gotten more conservative or looser over the past handful of years in the cash games you play or observe?

DO: People have gotten better in just about every aspect of the game, so most are tougher to read and bluffing more appropriately. People are probably more conservative overall, playing fewer hands and not bluffing wildly as often.

BP: Can you talk about the state of online poker cash games on the US sites? What has it been like and do you think it will improve greatly with more states in the mix?

DO: The no-limit hold’em cash games on the Nevada sites are fairly tough at the $2-$5 limits and higher. The New Jersey games seemed softer because the player pool is larger, but I only played there briefly. The bottom line is that online poker in the US is being beaten down by government ineptitude, that will never stop, but hopefully it will start getting gradually better soon.

BP: What does the government just not understand about the way poker sites should be like?

DO: Well, clearly anyone outside the industry isn’t going to understand it nearly as well as industry experts, yet these people have a large hand in industry regulation decision making. This is typical for all areas of government regulation. The biggest problem is liquidity. Poker sites need a lot of players, and intrastate gaming just doesn’t allow any state to succeed and prosper. Look at what Spain, France, and Italy did to demand in their own markets by not participating in the global player pools. Now poker is brutal in those countries. They make less tax revenue than before, and yet they remain isolated markets. Government regulation is often devoid of any and all logic.

BP: Definitely. Can you talk about how liquidity affects cash games specifically?

DO: When there aren’t enough players, games don’t run consistently and it’s harder to get games started. There are also a higher percentage of professionals, since they are more willing to wait around for games and jump through the regulatory hurdles than amateurs are.

BP: What are your thoughts on all the training sites out there that coach people on how to beat cash games? Do you think they are somewhat problematic for the health of poker? Or do you think that they help promote poker enough to counteract any issue related to improving the skill level of the non-pros?

DO: They certainly aren’t helping poker, in my opinion. The skills they’re teaching don’t encourage enough amateur players to outweigh the increase in players’ profitability. To be fair, I don’t use any training sites, so I don’t know how effective they really are.

BP: If you could go back in time and tell younger Dan to do something differently with regards to playing cash games, what would that be?

DO: I’d say study harder, talk to more good players, and move up in limits. I was far too complacent and didn’t improve as much as I could have. I stayed at low stakes because I was happy winning.

BP: How important is it for cash game players to push themselves? Is this sort of a fine line that you shouldn’t get too carried away with?

DO: Everyone has his or her own goals and limits, so it really depends on what you want to get out of it, but it’s good for everyone to play against players who are better than them every now and then to pick up some new strategy and to remind themselves that they still have a lot to figure out in this game.

BP: What kinds of goals do you set for yourself for a given month or year or for your career?

DO: I’ve been playing mostly tournaments the past few years, so it’s nearly impossible to set goals other than to show up to a lot of them and play well. I’ll be playing more cash games going forward and traveling less, so I’ll have to set goals for sessions per month and make a reasonable goal for profit. ♠