Poker News Daily: When you first started playing poker, did you have any idea you’d become this successful?
Greenstein: I started when I was 12 years-old playing for quarters. I used to golf for money and play poker for money. When I started off, I just wanted to be able to pay for golf with my poker money. I always seemed to do well at it. I played a lot of games when I was a kid and also played a lot of sports. I was always successful at poker and I knew from the time I was a teenager that if I just stuck to poker, I’d be in good shape financially. I used to play on weekends when I was in college and picked up money to pay for things.
I did so many other things in my life and education was always my priority. I liked to learn outside of school. I was a scratch golfer when I was 18 and planned to be a professional golfer more so than a professional poker player. Poker was something I did on the weekends to make spending money.
I wish that some of the younger kids today would play poker a little bit a little more in moderation and carve out a life for themselves. I’m afraid for some of the younger kids, and especially the ones who dropped out of college, who will find that they want to do something more productive than just play poker. When they’re 30, they’ll say that they don’t have anything else they’re able to do for a living besides poker.
A lot of times, I blame the parents. They teach their kids that success means having a lot of money. If you’re an intelligent young kid, poker is probably the best way to make money. I made some money to be able to do things like travel around the world. However, players shouldn’t make poker the only thing in their lives.
You don’t have to be the best at poker in order to do well. You just have to be better than the people you’re playing against. If you’re a decent player, you should be able to find games that you can beat. If you look at the big picture, that will allow you to have a better life.
PND: What job would you have if you weren’t playing poker professionally?
Greenstein: I took some time off from poker to do computer programming when I was in my 30’s, but what I really wanted to do was go back to school, become a doctor, and do medical work. That’s what I was hoping would be my life’s work, but there were financial reasons why I was never able to do what I wanted to do. I always had to come back to poker as a source of income. When I needed more money, I played more poker.
PND: What do you like the least about playing poker professionally?
Greenstein: When you’re doing poorly, there are a lot of bad things about poker. It’s depressing. I’ve certainly laid in bed at night and wondered how anyone can win at poker. It seems so absurd to be playing cards for money when you’re not doing well. Even when I’ve done well and needed the money, I have to admit to myself that there are other people I’ve taken money from. I have to question the morality of that.
For my own children who asked me how to play poker, I tell them to have a passion for something else that’s more productive, more interesting, and more intrinsically fulfilling than poker.
PND: Explain the predatory nature of poker.
Greenstein: I like playing with wealthy, bad players who have enough money where I don’t feel like I’m hurting them or changing their lifestyle. I have, at times, quit playing against people who I knew I was hurting. I don’t have that killer instinct to destroy people. In the games that I play in, everyone is a professional. The way I rationalize what I do when I play against other professionals is I look at it like it’s any other capitalistic endeavor. It was the same way when I was writing software. I thought that I wrote better software than other people and, as a result of that, I might have put other people out of business. In capitalism, some people don’t succeed. In some cases, I could even rationalize winning by saying it’s a good thing that I’m putting other people out of business and forcing them to do something that’s better for them.
The times that I’ve had issues are when I’ve played against people who really can’t afford to play poker. I’ll never lend them money and I’ll let up on them. Other professionals will say that if I don’t take their money, someone else will. I always felt that I could find other spots that were more reasonable for me to make money.
PND: What aspect of playing poker do recreational fans not understand?
Greenstein: Most people have the impression that we’re all multi-millionaires. I don’t know how many times I’ve had people tell me when I’m playing that it must be great to never have to worry about money. I tell them that if I didn’t have to worry about money, I wouldn’t be sitting here playing. PokerStars doesn’t ask me to play in cash games like they do to a lot of other people. I play cash games anyway and I’m really trying to make money. I am paying the bills with my poker money.
I don’t have as much money as people might think. I’ve given money away. I’ve lost money in the World Series of Chinese Poker. People will often look at career winnings, but they forget that money goes to taxes and money goes to expenses. My expenses right now are about $100,000 per month, so if I sit and do nothing, I’m losing over a million dollars per year. I have to make a lot of money.
A lot of people asked me why I signed with PokerStars. With all of the tournaments going on, I couldn’t play in as many cash games. I wasn’t making the money I had been making. I get a monthly check from PokerStars and it helps allay the cost of living for me. I’ve got three kids in college. I’ve got a lot of expenses.
PND: What qualities are often overlooked when considering what it takes to be successful?
Greenstein: Some people don’t have what it takes. There are some people who are just competitive. The most important quality for a successful poker player is psychological toughness. You will go through some downtimes. Bad things are going to happen to you when you play poker. Some people are going to learn from them, whether it was because of their own doing or just bad luck. Some people can’t handle things going against them. I have always felt that I’m the toughest person I know psychologically.
PND: What mistakes are common as people move up in poker?
Greenstein: Most people, when they jump up, jump into much bigger games. You see people who win 20 times in a row and then go broke when they lose once. A lot of people leave at the wrong time and don’t realize that the game is good. The times that you should take a shot at a bigger game are when you’ve been doing well and that game looks juicy. Knowing when to take your shots at the bigger games is really important and I think a lot of people get it wrong. I also see people who are just lazy. When you’re making money, you should try to make as much money as you can.
PND: What are some strengths and weaknesses of online poker players?
Greenstein: The general weakness is that they play their value too much. A lot of that is the internet. You don’t get as many reads on your opponents. You get a lot of tells live and a lot of online players underrate that because they’re not good at it.
PND: Which online players have you been impressed with?
Greenstein: There are a lot of good online players and they’re only going to get better, especially in the live environment. I hate to single anybody out because we’ll see that some of the players who are skilled will destroy themselves in other ways like relationships, alcohol, or drugs. There are so many pitfalls when you play poker. Playing the cards is a small percentage of what it takes to be a successful poker player. We’re going to see some of these players who we think might become the greatest player in the world and, five years later, not hear anything about them. Among younger players, I look for the ones who handle themselves well.