Words come easily for Teddy Greenstein — as they should for a sportswriter with more than 20 years of experience with the Chicago Tribune. But it’s not just the written word. Converse with the long-time scribe, and you’ll hear a smooth voice capable of providing facts and figures across mediums that include radio and television.
Those entwined parts of Greenstein’s skill set are now center stage for PointsBet, which announced a partnership with Front Office Sports this week to create “Hustle,” a sports wagering newsletter that will be published three times weekly starting next Thursday. Greenstein, whose full title with the Australian-based sportsbook is senior editor and player development manager, has final editorial say for Hustle, accountability he relishes.
“The challenge is you want to give a lot of good info, but you don’t want it to be too long. Nobody has any time,” Greenstein told Sports Handle last week at Hawthorne Race Course. “In the span of three minutes, can I give people information, arm them with info, get a chuckle out of them?
“I’m just trying to make as great an issue as I can. That it’s my baby and they’ve given me so much leeway is exciting. Instead of writing it myself with PointsBet staff, we have professional writers who can do a lot of the heavy lifting.”
Hustle will be the national public-facing part of Greenstein’s expanded role — the newsletter is expected to reach approximately one million people via email — but being director of player development could provide additional resonance for him and PointsBet as they look to gain market share in Illinois, the sportsbook’s top-performing state.
‘It was like meeting your work spouse’
Incredibly excited to team up with the PointsBet team to launch a multi-day newsletter for their audience!
The newsletter, created by our in-house content studio, will launch three times a week (Sunday, Monday, and Thursday) starting on September 8th. pic.twitter.com/avSfFeFOcD
— Adam White (@FOSAdam) August 30, 2022
Greenstein had long wanted to write about sports wagering while at the Chicago Tribune. Long before the U.S. Supreme Court struck down PASPA in May 2018, he was already incorporating point spreads into his weekly column picking Big Ten games, insisting they be inserted because the interesting question was not “that lame ‘Is Ohio State going to beat Akron?’ It’s ‘Is Ohio State going to cover the 33 points?'”
Even before Illinois legalized sports wagering in June 2019, Greenstein had a typical Chicago resident’s wariness when it came to state government and a new source of tax revenue.
“Oh, I know what’s going to happen — Illinois loves to tax everything,” he jokingly recalled, “so it’s going to be -117 on both sides and nobody’s going to do it anyway because they’re going to find a way to ruin it.”
PointsBet came into Greenstein’s orbit late in the summer of 2020 when he received an email with the PR pitch that Devin Hester would be the sportsbook’s brand ambassador for Chicago. Greenstein recalled it being one of a select few pitches he responded positively to — “Reply, yes!” — and his subsequent write-up started the chain of events that altered his professional trajectory.
“They were looking for somebody in Illinois who can write a little bit, be on air, maybe bring some other skills to the table,” he said, recalling meeting PointsBet CEO Johnny Aitken and talking shop at a sports bar near the United Center on a separate occasion after the Hester unveiling. “I was looking to get into the industry — not eager to leave newspapers, but very open to leaving newspapers.
“They made me a very nice offer and it was the easiest decision of all-time to join PointsBet.”
Sports knowledge ≠ gaming industry knowledge
Greenstein enjoys being an ongoing student of sports wagering. He recalled the surprise of PointsBet’s trading desk sticking to its guns with the Tampa Bay Buccaneers for Super Bowl LV and not moving the line to create a more balanced handle, which contributed to operators winning big in Illinois given the lopsided action on the Kansas City Chiefs. “I want to know what works, what doesn’t work” was said more than once during the interview.
He has been part of BetCast, PointsBet’s wagering-specific telecasts in cities where the sportsbook can leverage its deal with regional NBC Sports networks, including Chicago and Philadelphia. Greenstein says he has taken more out of BetCast than traditional telecasts because it provides “the insight I crave, so I hope there are a lot of people out there craving it too. The more, the better.”
Greenstein is willing to lean into parlay wagering, which now comprises a sizable portion of operator revenue. PointsBet mirrors that trend to a degree in Illinois, where those bets account for approximately 20% of handle and more than 40% of revenue. Its win rate on parlays this year is 15% compared to 6.8% for all wagers.
He thinks bettors know parlay wagering is not conducive to building a bankroll, but he’s not going to dissuade them from placing those bets.
“Look, I’m a sports bettor too, and I can’t resist parlays,” he said. “Who can resist the concept of betting $20 to win $140? I construct these parlays and I’m like, ‘Of course that’s going to hit,’ and it does one out of eight times. The standard client, you get one single game [daily boost] and one anything you can think of [daily boost]. You can start to parlay and it’s +700, and you click that box, and then it’s +765. The math still favors us, but it tilts it in your favor.
“Parlays are a great part of betting, it’s unbelievably satisfying to hit them. Parlays yield great content, great stories too.”
When there’s still more hustle to be had
The Cats are up and @RichardERoeper and I are entertaining the masses at Hawthorne for @PointsBetUSA. Life is good. pic.twitter.com/pyKN1Hnhbm
— Teddy Greenstein (@TeddyGreenstein) August 27, 2022
Even as he brought Hustle to life, Greenstein felt he had more to offer PointsBet.
“As much as I’m a content guy and I love all this stuff, I find myself going to sleep at night and waking up thinking about player development,” he said. “In March, [Senior VP of Customer & Insights] Ron Shell said, ‘Hey, Chris Bukowski and I are creating this new development, and it’s player development.’
“Ron went, ‘Look, you have connections in Chicago, you’ve been there a long time, you know sports guys and golfers and all that. We think you can be great for this,’ and I’m like, ‘Sure, let’s give it a shot.’”
That sent Greenstein on a path of building relationships with some of PointsBet’s higher-handle bettors. The player development side of his role eases his occasional doubts about whether content is helping PointsBet’s bottom line because, as Greenstein put it, “If you’re bringing in the right guys, you know you’re helping the bottom line.”
Zach Stonewall, one of Greenstein’s clients, is unafraid to occasionally place $5,000 bets. After some back and forth via text and calls, the two built a friendship that took off in April 2021 when Stonewall accepted an invitation to join Greenstein at Wrigley Field. A whirlwind day ensued that started with a Cubs win followed by Stonewall hitting a wager of $4,300 and change on Baylor covering against Houston in the Final Four.
The “and change” part still provides laughter for the pair. Greenstein recalled asking Stonewall, “How did you come up with that number, is it some lucky number at the end?” to which Stonewall replied, “No, at the end I was just hitting numbers.”
That day is also when Greenstein appreciated just how dramatically his professional life changed.
“Instead of getting to Wrigley four hours before with a laptop — yeah it’s a great job, but you’re also stressed. What’s my notebook? Oh s**t, this is on Twitter, I gotta go check out this trade. Oh, the GM, I gotta get him to call me back. Oh, I’ve gotta book my travel, figure out what my game story is. All the things you do as a writer. Now, I’m getting to the game 15 minutes before, buying drinks, buying food, hanging out, talking betting. And I’m like, This is the way to go, this is how you live!”
For Stonewall, Greenstein can troubleshoot potential issues, such as a deposit that may not originally go through, questions about PointsBet matching offerings other books may have, or customary wagering advice. Greenstein prides himself on that service since he feels it’s important for bigger bettors to have “a guy” who will provide those answers in prompt fashion.
Growing a newsletter, growing market share
Golf is my therapy and also the reason I need therapy pic.twitter.com/4MkoEJO8Mx
— Paige Spiranac (@PaigeSpiranac) August 25, 2022
There will be some familiar names in Hustle, as Greenstein will be enlisting PointsBet USA Head of Trading Jay Croucher and former pro golfer-turned-ambassador Paige Spiranac to offer expert picks. Greenstein likes how their two personalities play off each other, a yin and yang of sorts when it comes to methodology.
Greenstein expects each newsletter to have six to eight betting items, with Thursday’s edition focused on college football, and the Sunday and Monday versions more NFL-driven. He will be plenty busy between Hustle and player development, but it’s clear he has found a comfort zone to be at his best in both roles.
“I’ll bring it on myself, I want to bring in more clients,” he said when asked how to improve PointsBet’s market share in IIlinois. “I want to bring in great bettors, guys who are going to bet a lot on NFL weekends and college football weekends. That’s one thing I can do. I can do my media hits as well as humanly possible and raise awareness.
“I take pride that Illinois is our best state in market share and [want to] get that into double digits and beyond. That would be a real point of personal pride.”