How to Become a Millionaire Playing Fantasy Sports

Working in finance might be a quick way to make a buck, but for these three lucky gamblers, fantasy sports have been even more lucrative. 
Avatar:
Author:
Publish date:
Social count:
3
Working in finance might be a quick way to make a buck, but for these three lucky gamblers, fantasy sports have been even more lucrative. 
placeholder title

Peter Jennings is a busy man these days, so you’ll understand when he asks politely if he can wait until he’s home in Denver to do an interview. After all, he is partying at the Playboy Mansion right now.

There was a time when lifestyles of the rich and famous applied only to professional athletes — not professional fantasy players. Times have changed. Jennings is one of a growing group of full-time daily fantasy sports players. The two leading industry sites, FanDuel and DraftKings, were valued at $1.5 billion and $900 million respectively in April, according to The Wall Street Journal. Disney, owner of sports megapower ESPN just formed a partnership with DraftKings. When speaking to DraftKings CEO Jason Robins, he wouldn’t comment on the reported deal.

And the money is trickling down. At its core, daily fantasy sports are simple: Buy in to a game, choose your real-world players according to salary cap numbers from the site and whoever performs the best wins prize money.

“We like to gamble on things we have an edge on,” says Adam Levitan, a fantasy sports writer for Rotoworld. “Like sex, everybody thinks they’re good at it.”

The Fantasy Sports Trade Association pegs the number of fantasy sports players in the United States and Canada at 41.5 million in 2014. But only about 2.5 million are playing daily fantasy sports. The rest play season-long leagues in which there is little, or most commonly no, money to be won. Yahoo!, an industry leader in season-long leagues, announced in April they would launch daily games later this year. As the number of players continues to rise, so does the prize money. Talk to Jennings and he’ll use the word “bullish” a lot to describe the landscape.

“It’s going to hit a tipping point, or plateau,” says Al Zeidenfeld, a fellow professional daily fantasy player, “But we’re nowhere near it.”

“This is the first inning, maybe even spring training,” Robins says.

Jennings knows plenty about growth markets. The 27-year-old grew up in Littleton, Colorado and now lives a short drive away in Denver. He’s spent much of his short professional life chasing growth markets. Jennings graduated from Colorado State where he studied real estate. He planned to be discussing the merits of Denver’s booming housing market, not the Broncos’ booming passing offense. But you’ll find a common thread with many daily fantasy sports players: poker. Jennings played online poker at a professional level throughout college. He continued after he graduated in 2010, making a healthy living while also working in finance for Charles Schwab.

Then came April 15, 2011, a date known as Black Friday to the online poker community. It was on that date when thousands of poker players, including Jennings, found their favorite sites — Poker Stars, FullTilt, Ultimate Bet, etc. — suddenly shut down by the U.S. government.

“What do I do?” Jennings said of his sudden loss of income. “Poker was much more lucrative than anything else, including finance.”

He debated moving to Las Vegas and playing poker professionally — until he discovered the burgeoning industry of daily fantasy. He’d played year-long fantasy as a hobby, but daily fantasy began to consume more and more of his time.

“You couldn’t get the volume to do it every day [in the early days of daily fantasy]. I was actually bringing an iPad into work [at Charles Schwab] and setting my lineups from work,” Jennings says with a chuckle looking back.

Eventually Jennings decided the financial markets weren’t for him as daily fantasy picked up in popularity. But the breakthrough that allowed him to go full-time didn’t come until December 2012 when he took home a $150,000 prize in a FanDuel football contest.

“I literally quit my job two months before [winning],” Jennings says. “I was really bullish on the business side as well. I was very fortunate to win that tournament.”

And no, Jennings does not sit in his parents’ basement, contrary to outdated, keyboard-warrrior stereotypes. He got engaged this year and will get married next summer. He’s been with his fiancee since before he started playing daily fantasy, and while she may not have been fully on board with fantasy when he quit his job, she is now.

“She wasn’t that supportive until I won that big prize,” Jennings jokes. “She’s great. Not everyone is that supportive I imagine.”

Jennings took his biggest prize last summer when he won a baseball tournament — and pocketed $1 million. Make no mistake, Jennings — and every pro — is dealing with big sums of money. And while he preferred “not to talk about net profit,” he’s not throwing down in $1 or $5 leagues where the prize is a few hundred dollars.

“During the fall, I’ll have six figures down [in one day]. Five figures during the summer,” Jennings says. “Definitely there’s a lot of volume out there. From November to December, I’m on my computer for like 12 hours a day. I try to get up and move around, but I’m basically constantly working. … I basically eat, sleep and play fantasy.”

Oh, and hang out at the Playboy Mansion, where FanDuel was hosting a fantasy basketball tournament the first weekend in June. (He finished eighth out of “a couple thousand,” which was “all right.”) Jennings says the Mansion was “pretty cool” and suggested “you should come out.” He also casually mentions playing in a charity poker tournament in May where he sat between Mavericks owner Mark Cuban and some golfer named Tiger Woods.

“I talked a lot of basketball with Mark Cuban; he’s a great guy,” says Jennings, who adds Cuban is a big fan of daily fantasy. “I have four TVs. I try to make sure I watch every [NBA] game,” Jennings said. “I’m really into advanced analytics. We hit it off because we’re both big basketball nerds.”

●                      ●                      ●

If Jennings is the Kevin Durant of daily fantasy, Al Zeidenfeld is the Tim Duncan. The 42-year-old Zeidenfeld approaches playing fantasy sports like an accountant approaches a spreadsheet.

“Why are some people better at playing the stock market?” Zeidenfeld asks. “We all have access to the same information, some people are just able to see a better result.”

Zeidenfeld was born, raised and still lives in Los Angeles, but he saw his life going much differently. He planned to be on the other side of the broadcasts he watches obsessively each night. He left sunny Hollywood to go cross country to snowy Syracuse University where he majored in speech communications at the school’s prestigious S.I. Newhouse School. He wanted to follow in the footsteps of Bob Costas and Marv Albert as a sports broadcaster. Instead, like Jennings, he found professional poker. He played professionally for seven years before eventually making fantasy sports more than just a hobby.

“It’s always been this huge part of my life,” Zeidenfeld says of playing fantasy sports long before the Internet revolutionized the pastime. “We started a league [with some friends] which is now going into our 21st season this fall. I was the guy in your fantasy league who took it a little more seriously. I would wonder why other people didn’t take it as seriously as me.”

Zeidenfeld has found a like-minded community in daily fantasy. During the summer he’ll put down $2,000 to $10,000 per night, with more on football Sundays in the fall. It’s a lot of money, but Zeidenfeld approaches it as an investor more than a sports fan. He plays daily fantasy full-time — more than 40 hours per week truthfully — but points out he’s been smart with his money and has other sources of income so losing on a given night “doesn’t take food off the table tomorrow.”

Zeidenfeld is direct about daily fantasy being a zero sum game, saying “if I’m making $1.25 on every dollar I put in, someone is making $0.75.”

A 25 percent return on investment isn’t bad — unless you’re the guy playing against Zeidenfeld. He’s been making that ROI for over two years now, playing full-time after he took a $50,000 basketball tournament prize — the largest non-NFL payout ever at the time — in February 2013. It was a wake-up call to the potential money to be made, and not just for Zeidenfeld.

“My wife said, ‘Ya know what, you’re pretty good at this. We’re going to carve out some time for you to do this,’” Zeidenfeld says. He has two sons, 5 and 3, and doesn’t play fantasy on the weekends outside of football season so he can spend time with his family.

He’s leveraged his success into an advice industry. He’s the founder of DailyFantasyBootcamp.com, where he doles out daily advice to paying customers, and regularly hosts bootcamps in person, including ones in New York, Atlanta and Chicago this summer.

●                      ●                      ●

When you live in South Florida, it’s hard to spend all day inside on a computer. Unless you’re Drew Dinkmeyer. Dinkmeyer, 33, lives in Fort Lauderdale, Florida, majored in Psychological and Brain Studies at Dartmouth, worked at Morgan Stanley and is now one of the five pros sponsored by DraftKings. (Zeidenfeld and Jennings are as well. FanDuel doesn’t use “brand ambassadors,” as the players refer to themselves.)

In some ways, Dinkmeyer took an opposite path into full-time daily fantasy than Zeidenfeld — starting as a writer and becoming a high-volume player. Dinkmeyer writes for dailyroto.com, a site he started with fellow writer Mike Leone, which was purchased by RotoExperts in summer 2013. He now spends everyday from 9 a.m. to 3 p.m. writing content for his site and the time from 4 p.m. to 7 p.m. setting his lineups for the night of action. The rest of the night he’s watching games. And he has a very understanding wife, one who “doesn’t like sports.”

“We have two TVs. Our big TV is dedicated to her. She watches whatever she wants,” Dinkmeyer says. “I get the little TV and flip around through games.”

On Sundays during the NFL season, she knows to steer clear. He was still working at Morgan Stanley in December 2012 when he won $25,000 in an NFL tournament on DailyJoust.com. Joust, which has since gone under, was one of a number of smaller sites jostling for positioning behind DraftKings and FanDuel.

Ironically, in order for Dinkmeyer to win that big prize, he had to root against his favorite team, the Bears, who were in a tight playoff race with the Vikings. Leading the tournament in the final seconds of Packers-Vikings, Dinkmeyer won the $25,000 by avoiding overtime (his opponent had Adrian Peterson) with a Vikings win. The Vikings’ win put them in the playoffs and knocked out his Bears.

He used the $25,000 to go on a trip with his wife.

●                      ●                      ●

Daily fantasy is causing as much controversy as success stories, though. If you’re wondering why any of this is legal — even though gambling in the United States is illegal — it comes down to a provision in the Unlawful Internet Gambling Enforcement Act (UIGEA) which allows for fantasy sports. The UIGEA is the same law that eventually ended the poker career of Jennings, but it opened a new industry.

The law, signed by President George W. Bush in 2006, states it does not apply to “participation in any fantasy or simulation sports game.” But no daily fantasy sites existed in 2006. Rotogrinders, a popular site for fantasy news, pegs the first daily fantasy site as Fantasy Sports Live, which debuted in June 2007. FanDuel launched in 2009; DraftKings started in 2012.

Former Congressman Jim Leach, who authored the UIGEA, told ThinkProgress in May the idea the law would protect daily fantasy was unintentional. But there isn’t much concern over a Black Friday redux in the DFS community.

There is a consensus among pro players that deals fantasy sites have made with MLB, NBA and NHL make reversing course unlikely. DraftKings logos were emblazoned on the saddle of Triple Crown winner American Pharaoh and occupy space on the blood-spattered canvas of the UFC’s Octagon.

“People want there to be controversy for their own means,” Zeidenfeld says. “It’s a conflict of interest. … There are people with may more invested in this than me. I trust their judgment.”

“I think we’re in a great place,” Jennings says. “I really was concerned about it my first couple years in it, before the big partnerships, but it is safer now.”

The only league holding out on signing a deal is the NFL, however, some individual teams have signed advertising deals. FanDuel signed deals with 15 teams, including the Washington Redskins, New York Jets and Green Bay Packers, in April. The money to be had in a deal with the NFL, far and away the nation’s most popular sport, would be astronomical.

“Can you imagine a FanDuel logo at midfield in the Pro Bowl?” Levitan asks. “I’m sure the sites — FanDuel, DraftKings — would pay any amount of money for that.”

●                      ●                      ●

The amount of people who play daily fantasy full time is still extremely rare. Professional players, even ones who promote DraftKings, play on every major site nightly because they literally can’t put down five figures on one site.

“You have to put in a lot of volume [to play professionally],” Levitan says. “Very, very, very few people can play full time because they don’t have the money.

“People thinking about doing this for a living should think twice before they try to become the next Al or Pete. … A lot are going to fail miserably.”

Jennings repeatedly used the word “blessed” to describe his experience.

“I feel honestly blessed to be doing this everyday,” Jennings says, sounding as shocked as many outsiders are. “Everything I wanted to do is now ‘work.’”

Interested in Fantasy Sports? Try Maxim's Fantasy Sports App

Photos by Jeremy Cowart / FX