Jason Calacanis has hit a few home runs as an angel investor. With companies like Uber and Tumblr on his resume, Calacanis says he’s freerolling on life.

One of the things he likes to do with that freeroll is play poker.

Calacanis is an avid poker player who started playing low stakes games in Los Angeles and is now facing one of the world’s toughest fields in the $111,111 Big One for One Drop.

The six-figure buy-in event drew around 170 players and nearly every one of them is a threat at the table.

Calacanis: Poker is Good Analogy for Angel Investing

Calacanis, who mostly plays cash games, says he’s had a good year and has improved considerably thanks to some mentoring and a few tips from Phil Hellmuth.

Calacanis, who’s built his career on internet startups, also sees poker going through a renaissance if online poker gets federally legalized in the United States. It’s something he sees happening in the next handful of years.

But for now, Calacanis wants to put his poker skills to the test against some of the world’s best players. The goal is to make it through the day; cashing or making the final table would be another home run.

PokerListings: What made you want to play the One Drop?

Jason Calacanis: I think the charity is the number one reason and number two is to play with the world’s best players and see how you do.

I’d qualify myself as a serious amateur and it’s just a thrill to play with the world’s best players. 

The structure is also very nice because it only takes three days. I used to play the Main Event which is a lot of work for a 10K buy-in. This is a little bit more, you know, in my zone in terms of focus.

PL: What kind of games do you play throughout the rest of the year?

JC: Cash games, I don’t play tournaments. So I have to change gears pretty severely for this.

But we have a group of guys who play in Silicon Valley and LA. You probably know some of them here. Chamath, Roger Sippl, Brigette Lau, who is Chamath’s wife, they’re all good friends.

And Phil Hellmuth too. 

PL: Do you guys plan on how you’re going to take on the pros at the One Drop?

JC: Basically, when I play in this tournament, I know that I’m at a severe disadvantage. I don’t expect to be plus EV coming in, but I’ve done fairly well in cash games so this is just like a little treat.

It’s fun to play with the world’s best. The table is really just great players. There’s no civilians here, these guys are animals and they don’t seem to operate at the same level as civilians when they’re playing.

There’s only one rebuy so you can’t really get too cute here. You gotta play with a serious level of focus. That’s what I like about it. This is the first time I’ve played a tournament this big. 

PL: So how are you feeling about the tournament so far?

JC: I’ve been playing poker for probably seven or eight years now. I started in LA playing very low stakes, $200 buy-ins and worked up to $10,000 buy-in games.

I’m pretty comfortable with playing with $50k or $100k in front of me. I feel like I’m at a significant disadvantage, but not an insurmountable one.

So if I think I play my best poker, there’s a chance I could cash. I play with Phil Hellmuth and he’s given me a lot of great tips.

Phil has helped me fixed a couple of leaks in game over the last couple of years. He’s been a real mentor to me on a poker basis, and I think without Phil I wouldn’t be confident enough to play in this.

That’s probably a side of Phil that people don’t see. He’s very generous with amateurs like myself.

I’m probably twice as good a poker player just from playing with him.

PL: There’s been a lot of failed attempts to sportify poker. Now the GPL is trying with The Cube. What do you think is the biggest challenge poker faces in getting a wider audience?

JC: Obviously, people not being able to play online for real money. It’s very hard I think for the sport to expand without it.

So until we get poker legally online, I don’t think it’s going to be able to break out. I do think that’ll happen in the next three to four years though. I think that little dip you saw in interest will go right back up.

It’s sort of like the internet. Like when the internet bubble burst, sure there was a dip in the stock market, but eventually, broadband just connected the dot and the chart just went up and to the right.

So I think poker will have that moment when it becomes legal again online. And then I think it can become like it was in the glory days. 

I think there are major trends going on in the USA that are very positive too. So if you look at the legalization of marijuana, gay marriage and the acceptance of gambling, all of these, you know, puritanical concerns that the country had are going away.

And the next generation of millennials, they don’t care about race, they don’t look at marijuana as something horrible and I don’t think they look at something like gambling as something horrible.

Adam Silver from the NBA saying we should readdress this was a major moment for poker. Because if the NBA and the NFL can get comfortable with the Draftkings and if they put professional sports teams in Las Vegas the industry is going to tip over.

It will be great for everybody. Having it be legal in three states is the same as it not being legal anywhere. Until we have one understanding, it’s going to be very hard.

PL: Social media has also been playing a big role in poker…

JC: Yeah, It wasn’t always like that. I remember coming here and playing when I was a Full Tilt Red Pro and we had to have a discussion. Like, can I Tweet?

Now I’m sitting here and everybody’s Snapchatting without even asking anybody’s permission.

If you took a camera out and put it on somebody 10 years ago, you’d literally get punched in the face.

This next generation, they don’t care, nobody cares anymore. I think for the Rio they realized Tweeting and people doing social media helps them.

So the more they can embrace technology, the better it’s going to get. I think the live streaming and what Twitch is doing might do wonders for poker. Poker will go through a renaissance.

PL: How does high-stakes poker compare to investing? 

JC: The level I invest in startups I’m usually one of the first five investors. I look out and see that maybe it’s a little awkward and rough around the edges but say, “Yeah, fuck it I’ll put $25k in.”

So I’m an angel investor. Someone like Chamath is a venture capitalist and then David Einhorn is a public markets guy.

If you look at those three phases I’m like the pointguard, you know, I bring the ball up court. Someone like Chamath might be a small forward and Einhorn might be a center.

When I invest there’s like two or three people in the company. When Chamath invests there’s like 10 or 20 people, but when someone like Einhorn gets involved there are hundreds or thousands of people in the company.

Poker is a real good analogy for angel investing because of implied odds. It’s sort of like playing really bad cards with a very deep stack and seeing a lot cheap flops.

I put $25k or $250k into a company and own one to five percent and most of them fail. So that one to five percent times is usually, 8 of 10 times, worth zero.

Then one hand you kind of chop it. Then, hopefully, one hand out of 50 becomes Thumbtack or a Wealthfront.

Then sometimes you hit the royal flush like Uber.

I was the third or fourth person to invest in Uber and it only takes one of those to kind of make your career.

Those are the equivalent of a 5,000 to 10,000 times return.

PL: Have your investing skills helped you in poker?

JC: They’re very analogous and I think reading people is a skill of angel investors.

It’s also what Chamath does a lot, reading people understanding people. Understanding motivation and then also trying to solve problems with limited information.

When you look at poker you’re trying to uncover this riddle and you don’t have complete information. 

PL: What would winning this event mean to you?

JC: My life is really, really good right now. I don’t want for anything and have gotten so lucky in my career.

I have like three or four hits so I’m kind of freerolling on life.

But to me on a personal level, if I were to final table or even cash, it would be better than anything else in my life right now with the exception of my family. Literally for me, to make it to day 2 with this type of group, with Antonio and Phil, would be incredible.

I cant imagine what it would be like to final table this. One of the great things about poker it’s an open sport anybody can go up and you can get a chip stack.

It’s one of the most open communities, that’s one of the things I like about it. It’s also constantly changing, so I think it keeps you very mentally sharp.

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