Jon Aguiar made the jump from poker to the sports gaming world, and he’s fitting right in
Logan International Airport in Boston is hardly the place where life-changing decisions are normally made. Sure, people come and go every day — arriving from or leaving for the adventures they’ll spend the rest of their days reminiscing about — but few of those stories will match up with the one former professional poker player Jon Aguiar will tell.
It was just two short years ago that Aguiar sat in departures area of Logan, waiting for a flight to take him to Europe so he could play WSOP Europe and a couple of European Poker Tour events. It would be terribly cliché to say that Aguiar’s life was at a crossroads but the events of Black Friday had taken a toll on the then 28-year-old.
He’d left the United States and traveled around the world to continue to play online poker. Mexico, Portugal, Canada — all were places Aguiar called “home” while grinding. During that time, he’d discovered daily fantasy sports and was instantly hooked. Daily fantasy sports sites are legal in the United States — ironically, thanks to the UIGEA, the 2006 law that was the first crippling blow for online poker — and allow players to draft a new team each day in any of the major sports and play against other players for money. One of the sites Aguiar was playing on — DraftKings.com — was in need of some feedback — or, at least that’s how he saw it.
“I just started playing a bunch, starting winning a bunch,” said Aguiar. “I saw a few things that I’d like to have seen changed, so I shot an email to support.”
While DraftKings was a growing player in the daily fantasy sports industry, it was still in bootstrap start-up mode. So the support emails were being answered by one of the co-founders, Matt Kalish. The pair became friendly after discovering they both had poker backgrounds. In one email, Kalish mentioned the site was based in Boston.
“I was like ‘Oh, you’re in Boston? I’m going to be in Boston on my way over to play WSOP Europe,” said Aguiar. A few days before leaving for Europe, where Aguiar would win his first and only career WSOP bracelet, Aguiar met with Kalish and Jason Robins, DraftKings’ CEO.
While waiting to board his plane at Logan, Aguiar was thinking about his lunch with Kalish and Robins and if it could expand to more than just an operator-customer relationship. At that lunch, the trio bounced some ideas around about how to improve the product, mostly focused on the customer experience. Even while he was in Cannes, France, winning his bracelet, Aguiar was still in communication with Robins and Kalish.
“When I came back, we had lunch and (Robins) offered me a consulting gig,” said Aguiar. “That’s basically what I did at first, spending maybe five or six days a month in the office for a better part of six, seven months.”
Things took another turn for Aguiar in May 2013 when DraftKings took on a $7 million investment from Atlas Venture. With some capital to work with to build out its operations, one of the first things it did was offer Aguiar a full-time gig. The job offer meant Aguiar would have to move his life to Boston — something he wasn’t sure he was down for.
“Back then, it was a little questionable whether I was going to move up to Boston and ship out all my stuff and get an apartment and, basically, change my life and leave poker,” said Aguiar. “I guess having won my bracelet at that point, even though it was just a WSOP Europe bracelet, against 100 people, it’s far from my crowning achievement, but it’s a lot easier when you tell people you’re retired from poker that you’ve won a bracelet.”
But that’s exactly what Aguiar did. He left poker behind, put his life into a bunch of boxes and made his way out to Beantown to work with DraftKings as its VIP manager. He’s since changed roles slightly and is now the director of customer experience. The title sounds fancy, but it’s actually purposefully vague — defining what he does on a day-to-day basis isn’t all that simple.
“I work with a lot of different departments based on what’s going on that week, so a typical day for me doesn’t really exist,” said Aguiar. “I may spend some time with our product operations team on a strategy and philosophy behind the mix of games that we offer for any sport or promotion that’s coming up.”
Even though he’s retired from poker, his experience there, particularly the online game where he first cut his teeth, plays a big part in his job now. For those who haven’t had a chance to try daily fantasy sports yet, some of it might seem familiar.
Just like online poker, players enter daily tournaments with a buy-in and compete against fields of between two and thousands of players, with top finishing players winning prize money. The tournament formats offered are taken directly from the online poker scene: sit-n-gos, head-to-head, qualifiers, step tournaments and probably most importantly as the industry enters a hyper competitive stage: guaranteed prizepool tournaments.
While all of that is an important part of Aguiar’s daily life, he claims it was lessons learned as an online poker player that he focuses on all the time.
“Just making sure that everybody, number one, has as much fun as they can on DraftKings, and number two, that they trust us as much as possible, which is one of the big things coming over from poker is just laying down that trust is the most important thing we have as a company,” said Aguiar, who also works directly with marketing and customer service reps to properly frame policies and responses to situations that come up.
Some who remember much of Aguiar’s time in the poker spotlight might find it surprising, maybe even ironic, that he’s in a customer service role. He was outspoken, some might have even say brash, on his Twitter account when it came to challenging the way poker companies treated players. Aguiar is fully aware of the role reversal.
“I find it a little bit more challenging, and I understand how hard it is to put the customers first in everything that you do as a business. But I still do understand the value in that and how, over a matter of years — and hopefully decades — that DraftKings exists, that the narrative about us needs to be ‘they always make things right,’” said Aguiar. “If something happens with Amazon, for example, you feel a lot more comfortable that they’re going to take care of you than if something goes wrong with your Comcast service. Being much closer to Amazon than we are to a Comcast in terms of the way people look at our company, it really just all comes down to trust.”
A little more than a year into his “real job,” Aguiar doesn’t regret the decision to stop playing full time. The challenge that DraftKings offers him has him motivated and while it’s allowing him to use some of his experience as an online poker customer, it’s also allowing him to use a skill set he didn’t get to when he was clicking buttons. There is one thing though that Aguiar does miss.
“I miss being around my friends all the time and being able to just travel around. It’s like I can’t be down in Playa or up in Toronto or just leave for three or four weeks of WSOP Europe and EPT events on a whim,” said Aguiar. “But outside of that, it’s been a really enriching experience. It’s driven a lot of change in my life that I really realized I needed. I honestly think that spending too much time in the poker world is a really big mistake.”
Being a professional poker player is in many ways a solitary venture. Sure, the friends on the circuit are something that Aguiar misses but he’s genuinely excited about the opportunity to work with a team for the first time in his professional career.
“I’m not really exceptionally masterful at any of the things that I do on a day-to-day basis. I have a breadth of knowledge and I have an intuitive understanding of the gaming industry, just coming from being a participant in it for so long,” said Aguiar. “There are dozens of people at DraftKings that I wouldn’t be able to look good without. I think I get more credit than is due for anything at DraftKings just because I have a bunch of Twitter followers or something. I really appreciate everybody that I work with on a daily basis and all of their individual skills.”
“That’s something you just don’t get in poker. There is no team aspect, so learning to live and die with a large group of people. When you make a mistake, it doesn’t’ just let you down. It lets a lot of people down,” said Aguiar. “I think that sort of changes your outlook or perception on things. That’s an extremely valuable thing, moving on from poker, that you get. You know, some people naturally have that, some people develop it. I certainly developed it.”
Even though he’s not jetting all over the poker world to play big buy-in poker tournaments any longer, he’s still jetting all over the poker world to go to big buy-in poker tournaments. One of the areas that DraftKings and some of its competitors have targeted with marketing is poker players. Familiarity with the product — we all recognize a sit-n-go, and don’t need an explanation on why only the top 10 percent of the field is getting paid — is a big advantage when it comes to liquidity. A big part of DraftKings’ push has been two key partnerships: the World Series of Poker and the World Poker Tour.
Just like the good ol’ days of online poker, players can win seats to WPT events or the WSOP Main Event through DraftKings. If you do, you’ll be face to face with Aguiar when you get there. He travels to each event and makes sure the players have a good time and get taken care of.
“You get your tournament package. You get airfare, spending money, and you get your hotel for the entire trip. Then, for guys that win that aren’t hardcore poker players and want the whole experience, we get you seats at the Monster Bar for the filming of the (World Poker Tour) final table,” said Aguiar. “A few guys have won one (a WPT seat) for as literally five dollars. We’ve offered them for baseball, basketball and now in football. We’ll also offer them in golf once that gets going again.”
Aguiar also makes sure the players get the chance to meet WPT commentators Mike Sexton, Vince Van Patten and Lynn Gilmartin and see the final table set before filming begins. For many of the players that have qualified for these events so far, the opportunity to play a WPT or WSOP event is a once in a lifetime experience and seeing that approach to something Aguiar once took for granted has been a real eye-opener.
“It’s the thing I enjoy most about coming out on the trips is seeing people experiencing poker the way I did but so long ago that I can barely remember it,” said Aguiar. “They have a wide-eyed approach to the WPT where they look at the room, and they look at all those tables, and they see the trophy, and they see the cameras.”
Given the lack of poker experience of most of the players that qualify, an in-the-money finish is a rarity, but even more rare are the players that leave disappointed by the experience.
“Most of them don’t cash but I hear the same thing from all of them. ‘Oh, I don’t care man — I had such a blast. I’m going to tell all my friends about this,’” said Aguiar. “I’m like ‘You didn’t cash. How could you have fun?’ but it’s like wait a minute, for a lot of people they don’t have to win money to have a good time. It’s been very refreshing.”
The WPT and WSOP packages are one thing, but the daily fantasy sports market is pretty competitive and a bit of an arms race is developing with DraftKings and its only real competitor for top dog status, FanDuel, offering massive guaranteed prizepools each week and across each sport.
“This is probably the best year that there will ever be to be a daily fantasy player. If you miss now, in two or three years, you’re going to be kicking yourself because I think the industry will be a lot more mature soon,” said Aguiar. “We’re overlaying six figure sums on individual contests right now just to stretch and get some of the prizepools that we expect to grow into this year. For example, our Sunday Million — with a $27 buy-in — just doesn’t fill right now, but we’re going to keep running that game until it does fill.”
DraftKings recently raised over $100 million in funding and a lot of that money is earmarked for massive guaranteed prizepools that will probably come with some overlays.
“Yeah, we’re just spending a lot of money on getting new players. It’s just like the heyday of online poker. This is the best time that there will ever for be for the players for that reason,” said Aguiar. “Obviously the prizepools and stuff will continue to grow over time, but the amount of money that’s being spent by the sites, just competing to run the biggest games is crazy right now.”
Aguiar recently returned from a trip to the Atlantis Resort in the Bahamas where DraftKings held its Fantasy Baseball Championship which featured a $1 million first-place prize. Peter Jennings, who plays under the screenname “CSURAM88” and is a member of the DraftKings Pro Team, took home the title and seven-figure score. Jennings isn’t some luckbox though, he’s considered by most to be one of the five best daily fantasy sports players in the world.
So, is Pro Daily Fantasy Sports player something that the everyday sports fan can aspire to the way they do with poker?
“Absolutely, I think it will be a smaller percentage of the overall player pool that it was in poker. I think one of the issues that poker is struggling with right now is that the number of people that have committed to playing for a living is making some of the ,” said Aguiar. “I would say it’s a better tool for supplementing your income right now than it is for going full time. It’s probably a much more logical and reasonable way of approaching the industry for most people, especially because the time commitment isn’t like it is in poker.”
“You can still put your time into your teams and then go to work or do it after work.”