Mahalo’s Jason Calacanis Q&A: ‘I Want to Play the Big One Next Year’

Jason Calacanis
Jason Calacanis

Entrepreneur Jason Calacanis has made millions in the business world but was more interested in just making it though the day at the WSOP Main Event on Monday.

Calacanis is one of the biggest players in the online business world and has an impressive resume that includes founding Weblogs, Inc. and human-search engine

The 41-year-old is a huge poker fan and even appeared on the PokerStars Big Game with Doyle Brunson and Daniel Negreanu a couple of years ago.

Calacanis is never scared to share his opinion and gave us some interesting quotes about the WSOP BIG ONE, the state of the online poker industry and why he loves poker.

PokerListings: So Jason how did you get into poker originally?

Jason Calacanis: I started playing poker in New York City, which basically translated into buying in for $40 and buying a lot of scotch. It was basically just coinflipping.

Then I moved to L.A. and everyone was still playing cards but it was a $500 buy-in. I lost like $10,000 the first year.

I was absolutely addicted at that point. People took poker seriously and I’m a very competitive guy so I got into it pretty quickly.

Jason Calacanis
Jason Calacanis

PL: What did you do to improve your game?

JC: It was very simple. I got very frustrated going back to my wife and telling her I lost $500 or $1,000 every time I played. I would just stare at the ceiling.

That amount of money isn’t that big of a deal to me but I’m ultra competitive and grew up very poor so if I lose $500 I’m grinding my teeth until 3 a.m.

I bought every poker book, listened to every audio book and started taking the game very seriously.

I began playing ultra low stakes at Commerce Casino and Hollywood Park like a degenerate. I would play at the $1/$2 table where people were playing with food stamps. True degeneracy.

I loved it though. I would try different styles. I would pretend I was Barry Greenstein or Phil Ivey.

PL: Where did you go from there?

JC: I played a few tournaments and eventually played a couple WSOPs but I couldn’t play last year because of a family commitment. I’m back this year.

This year I sold 60% of myself to my fans for equal equity. Just to give them a sweat. Everybody wanted to buy a ton but I tried to keep it to one point for each one.

I’ve got like 50 fans on Twitter who have a piece, so hopefully we win a lot of money.

I love poker, it’s the ultimate rush. It’s the ultimate sport for businessmen and Hollywood guys too. There are a lot of internet guys and a lot of Hollywood folks in L.A. so it’s sort of the Internet donks versus the b-list actors.

Chamath Palihapitiya
Jason Calacanis's close friend Chamath Palihapitiya

PL: What did you think of the $1 million buy-in BIG ONE this summer?

JC: I was up until 1 a.m. watching the really shitty stream but I would have paid $25 a night, or $50 a night or $100 to have an HD stream of the entire thing and let me pick the table.

WSOP if you’re listening there is a big opportunity, cause everyone I talked to was watching that horrible security camera stream.

I love it and next year I think I’m going to try and play in it by crowd-sourcing it because I have a big fanbase. Get them all to chip in $1,000 or something.

I was salivating like a rabid dog that was chained up with 800 pounds of meat inches away from its nose. God I wanted to play that tournament so bad.

PL: You seem like a huge poker fan, Jason, what is it you like about the game?

JC: What you’re trying to do in entrepreneurship is try and figure out if there’s a market somewhere and to exploit it and to capture it.

In poker it’s the same thing with a hand, you’re trying to develop a hand. You want to start with something good. In start-ups that’s starting with a market like social or mobile for instance.

Once you pick a market you try to develop it and other people are competing against you in that space. You have to constantly try and raise the stakes. You gotta raise and you gotta push people around but you’re dealing with partial information.

Poker is also one of the few things where I’m absolutely in the moment.

Day 2

PL: Do you have any goals in poker?

JC: I think I was a really bad player for a couple years and now I think I’m OK.  Sometimes I’m good. I think I’ve got a couple more years to learn. I keep doing better and better.

Ultimately I’d love to make a final table at the World Series. I don’t have time to play a lot of events but in the future I hope I’ll be able to take June and July off and play 10 or 20 events.

PL: You’re obviously very involved with social media. Social media is very prevalent in poker, do you have any thoughts about that?

JC: I think it’s great. It definitely opens the lines of communication and leads to a lot of fun. This way I can keep up with guys like Phil Hellmuth and see how they’re doing.

PL: What do you think of the poker lifestyle?

JC: I’m into the whole thing. I’m a degenerate. I love gambling. Risk-taking is my thing.

Society has a very bad view of risk-taking but that’s because they’re donks. Those are the people that don’t change the world. The people that change the world are the ones that take risks.

Look at the Elon Musk. That guy was all-in on Tesla, he was going to lose his entire fortune. Hundreds of millions of dollars.

He shoved, blew up three rockets and was almost wiped completely out. He was negative and then Tesla goes public. The car is a hit. Everyone is buying them.

The risk-takers like Steve Jobs, Elon Musk or Doyle Brunson, Phil Hellmuth and Daniel Negreanu – are totally inspirational to me.

I carry a lot of my poker experiences into the poker world. I think of my company as my chip stack. I think, “What’s the most aggressive thing I can do here? Can I take out these competitors. Can I hire these employees from the other competitor?”

I really use the poker metaphor a lot in my life.

Las Vegas Strip

PL: Obviously you’re involved with a lot of start-ups, do you have any interest in the online poker market, especially now that regulation in the U.S. looks eminent?

JC: Not really but I’m monitoring it. It’s a very tough market. In the poker space you have to have a network effect, so if you can’t get to PokerStars or Full Tilt levels then obviously no one will go to your site.

It’s going to be largely government regulated so it’s going to be hard. When it does happen, I wouldn’t rule it out.

PL: Do you see the big players in Las Vegas controlling the market?

JC: I think it will be the big players in Vegas and also the big Internet players. You’ll see Facebook, Yahoo, Zynga and Google will make alliances with either casinos or independent sites.

Do not be surprised at all if there’s a gaming section on Yahoo.

Perhaps Google wouldn’t go for it. Facebook certainly would. It’s absolutely conceivable that people around the world on Facebook could be playing in the world’s largest casino.

Once one of them goes for it, all of them have to go for it. They’ll get all this profit from it that they can reinvest in other things.

I would predict Zynga becomes the number one player in online poker. It will be a race between Zynga and PokerStars. Maybe whoever buys Full Tilt if they refund the players money.

This could change everything for Yahoo though. Yahoo has hundreds of millions of people on a global basis and their email addresses, if they flip on poker… Boom, they flopped the nuts.

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