Part-Time Poker Player, Full-Time Entrepreneur: Jason Calacanis
Internet CEO and entrepreneur Jason Calacanis has pursued a career of building companies out of nothing and this has spilled over to his poker game. Having successfully founded start-ups such as Mahalo, a human-powered search engine, and Weblogs, Inc., a network of blogs that would eventually sell to AOL, Calacanis has a knack for recognizing patterns and trends that has enabled him to be successful in the board room and on the felt.
According to Calcanis: “When you look at entrepreneurship and starting a company, there are a lot of similarities (to poker). You have to recognize trends and patterns in both areas. A lot of what you do as an entrepreneur is the same thing that happens at the poker table. How you are perceived at the table is very important. It’s the same thing when you go to a venture capitalist to raise money. You have to be able to put on a show with your hand to get other people to fold and give you your money. Concepts such as strength, intimidation and strategy play a big role in both areas. In a way, sitting at a poker table is just like starting a company. You start with some seed money and see if you can make it grow.”
While working on launching a company in New York, Calacanis was introduced to poker and quickly caught the bug. “A friend of mine started a game featuring Internet CEOs. It really was more of a chance to get together than a game. People didn’t know what they were doing. It was a $1/$2 game that often had five players in a showdown. We pretty much checked it to the river every time. There really was no skill involved.”
Despite the lack of prowess in his home game, Calacanis was hooked. He eventually moved to the West Coast and found that players took the home game to a whole new level. “When I came out to LA, people started inviting me to poker games. It was a whole different level of play as people were buying in for $500 or more. These people knew what they were doing and I found it fascinating. I started playing at Hollywood Park and Commerce once or twice a week.”
According to Calacanis, he immediately started finding patterns in people’s games at the casinos and he decided to jump in head first. “About three years ago I started taking the game seriously. I bought every audio book on the subject and I started reading poker books as well. I read Barry Greenstein’s book. It was very influential on me. His concepts on how people act when they are not at the poker table helped my game dramatically. I started seeing patterns in the people at Hollywood Park. They were tired from work or tilted because they were behind. I started recognizing these patterns and I’ve learned how to take advantage of them. I started playing at different times in the day and I started recording wins and losses to try to figure out how to maximize my chances of winning.”
Although he is constantly on the run thanks to his hectic schedule, Calacanis makes sure he has time to get in some action. “I probably play two to three times a week. Usually they are four to five-hour sessions. I’ve recently been playing a lot of cash games. I started playing at the big table at Hollywood Park ($5/$10) and at Commerce. I seem to have found an undeniable pattern and I’m trying to leverage it. Lately I’ve started playing at 2:00 in the morning. It’s a weird time to play, I know, but it is working for me. I try to take a cat-nap during the day and then head over to Hollywood Park to play. Everyone is either tilted or behind, playing catch-up. It’s awesome. I come in fresh at 2:00 and I feel I have a big advantage because I’m fresh. It’s like going into a basketball game and playing only in the last quarter. Everyone else is tired while I’m ready to play.”
When he’s not at the casinos, one can find Calacanis playing in his home game, which features a mixture of Internet CEOs and entertainment figures. “We play $5/$10 No Limit because it leaves some room for aggression. Every once in a while we play $10/$25, but people tighten up and the game isn’t as much fun. I’ve been lucky enough to become friends with actors like Kevin Pollack and Danny and Chris Masterson. Plus, I have a bunch of friends from the Internet that come and play. I try to keep a good balance between the two. These are interesting games to watch. The actors don’t care about the money so they donk off chips and the Internet guys do the same thing. Each group thinks the other is dead money. It is the perfect action game as people are usually $2,000-$3,000 behind. Some people definitely get hurt. I tried to start it as a $500 game but that didn’t work. Everyone would try to buy in for more than the other people. Once people started bringing checks, that’s when I had to put a limit on the game.”
After playing in the 2009 World Series of Poker Main Event as a Friend of Full Tilt, Calacanis found himself jonesing for another shot at WSOP glory. “That was the highlight of my last year. The caliber of play was better than I have ever seen. When you sit down at a table, you usually recognize a couple of guys you can take advantage of. By the second day of play, I couldn’t figure out who to pick on because the players were that good. I had four people at my table with over $100,000. That made things even tougher. I made it to the middle of the second day. When I busted it was probably the most disturbing thing in my life. I’ve never felt so much frustration.”
Unlike most celebrities or athletes, Calacanis is looking to take the next step in his poker career as he prepares to spend some time on the grind. “My wife and I have discussed me playing professionally several times. When I sell my next company, I am thinking about taking the next year to play full time. I am going to try to play poker five days a week just to see how good I can get.”
