Marco Piemonte readily acknowledges he is still coming to grips with getting recognized outside Illinois.
Already known throughout Chicago for running one of the city’s largest auto dealerships, Piemonte grew accustomed to the attention early through his father. Commercials for the Al Piemonte Auto Group aired on WGN-TV, the flagship station of the Cubs that was also one of the country’s first superstations. Marco Piemonte recounted people approaching the family dinner table when out in Florida, asking for his dad’s autograph and taking the occasional picture with him.
The son is now the one getting attention, but for reasons beyond selling cars. He is known on social media as “Million Dollar Marco,” the guy who places large bets and parlay wagers — that occasionally hit for six- and seven-figure payouts — and for his connection to Betr, an upstart sports wagering platform that counts reality star and aspiring pro boxer Jake Paul as its biggest social medioa influencer.
“I was trick-or-treating with my kids and I [was with] 15 kids, and how these kids know who I am, probably because of the Jake Paul stuff, and they’re ‘Hey, you’re from social media can we get a picture with you?’” Piemonte told Sports Handle. “I’m like, ‘I’m not that big yet,’ and then I go out of state and I’ve got 150 people who want to take a picture with me and it freaks me out. That’s where we’re at now.”
Paul is an undeniable presence — he has more than 21 million Instagram followers, another 4.5 million on Twitter, and 70 million social media followers overall. Piemonte has nearly 175,000 followers on Instagram and 51,000 on Twitter, but hit a $3 million payday like he did in late September, and people learn about you as fast as a new hashtag.
Piemonte is trying to make the most of his newfound megaphone and presence. His parlay wagers are the initial access points to him for the public, but he’s also someone who wants to make the sports wagering social media space and sports wagering through Betr, well, better.
Five-card poker, scratch-offs, and sports bets
— betr (@betr) October 19, 2022
Both of Piemonte’s parents worked, which meant he spent much of his time as a child with his grandmother. She provided his first exposure to gambling playing games of five-card poker with him and introducing him to scratch-offs. Piemonte’s introduction to sports wagering came in high school, when he was making wagers of $50 and $100 through a bookie. He recalled it being “big money” at the time.
Growing up in his father’s footsteps meant there were multiple formative and teachable moments in his life as a teenager and young adult forging his own path. The younger Piemonte had known what his profession would be since he was 12: “Little Marco’s going to be a car dealer!” he said with a laugh.
He left automotive marketing school in Michigan after one year and attended college for one year before joining his father’s company. The automotive industry exposed him to people from all walks of life, something Piemonte says “makes the car business a cool business.”
“It can be ‘Tommy T,’ who has a bachelor’s degree in marketing and whatever else, and someone has a Ph.D., and there’s a guy who just got out of prison,” he explained, “and they all melt together for one kind of cause, and it’s to sell cars and make money.”
This eclectic group in his professional orbit also taught Piemonte the ins and outs of sports betting. His bet sizes gradually increased from $100 to $3,000 as a young adult, noting the increases came as he was earning more money at work. Sports wagering, Piemonte said, was “my way to still be a kid again” after working 12-hour shifts.
Not that he found early success. Piemonte lost and lost big, at one point estimating his losses to be $200,000 — all of it his money, none borrowed — due to stretches of losing picks that sometimes spanned from weeks into months. He recouped some of those losses at the age of 19 when he finished fourth in a Full Tilt Poker Sunday tournament and won $43,000. The losses provided lessons about wagering and about the emotional peaks and valleys that come with it.
“It’s like, ‘Oh my God, you always make money when you gamble,’ and I’m like, ‘When I was younger I didn’t,'” Piemonte said. “I didn’t know how to bet, I didn’t know how to be smart about it.”
Marco’s business and the family business
Al Piemonte, whom Marco described as “an old-school Italian,” never approved of his son’s sports wagering. Marco Piemonte tried to rationalize his betting as entertainment considering he did not pursue other vices, but he also kept his wagering low-key around his father, whom he called his best friend. A military school upbringing contributed to Marco not drinking alcohol and staying clear of drugs, and also gave him the structure and discipline he still carries with him, a remnant of requirements for hard corners on his bed and highly-shined shoes.
“Not that you want to hide stuff from your parents, but I know gambling wasn’t the best thing for me at the time,” Marco said. “I know I wasn’t profitable, so justifying it was tough. It wasn’t until I got in my mid-20s that I started to have a lot of success with it and I started to buy stuff — whether it was jewelry, or go on trips, and I was funding it with the gambling money.”
Marco Piemonte is responsible for 470 employees spanning the five car dealerships that bear his father’s name. This extended family, plus his wife Allie and three daughters, come first. He wants his children to have “an easier kind of grow-up than I did. The kind of grow-up I wanted.”
He says he has no problems walking away from sports betting if it ever affected the day-to-day life of his family or employees.
The legal challenge for control of the dealership that started shortly before his father’s death as well as the actual passing of Al Piemonte in 2014 remain touchstones because there is an unflinching intensity to the 33-year-old Piemonte — he is constantly in the moment. And he’s unapologetic for what he was given during his upbringing in terms of material comforts and those he has since earned.
“People see the lifestyle I’m living, but they don’t understand I had a really good, comfortable start and was able to gamble with no fear. When you gamble with no fear, you don’t have any risk,” Piemonte said. “A lot of people have used that against me. And what I try to explain to people is that there are positives and negatives in growing up in the life I was given.
“There’s a lot of luxuries, but until somebody can live the life that you lived completely and feel the pain of losing their dad young, and some have … but try being 24 years old, your dad dying, and then a bunch of grown-ass men trying to rip everything that your dad did away from you and trying to be thieves at the same time. All these people that were around my dad were a bunch of snakes at the time and they all tried to attack my mom and I and take us down.”
Getting on board with Betr
“‘You’re friends with Jake Paul!’ No. ‘Oh my God, you’re best friends with [Betr founder and CEO] Joey Levy!’ No,” Piemonte says while breaking into laughter. “Have you met Joey and I? We’re opposites! He’s the smartest guy in the room and I’m the guy who’s being a class clown.
“Jake’s a very cool guy, we got along very well, we have very similar personalities. I didn’t know him until I met him in Miami when I already signed an investment deal with Betr.”
Betr came onto Piemonte’s radar through Mike Denevi, who previously worked with Piemonte at Bleacher Report with Turner Media. Piemonte specified, regarding his relationship with Betr, that he is not an employee, but a signed personality. He is an investor in the company, and Betr sponsors the 100x Club podcast he does with long-time friend Anthony Damato.
Betr recruited Denevi to be head of media, and he recruited Piemonte. Damato entered the picture soon after, and Piemonte is quick to give him credit for their success.
“He’s a human form of Xanax when I’m with him, helps me navigate different personalities I don’t want to navigate,” Piemonte said of Damato. “It’s like ping-pong when we’re with each other, it’s really nice to have someone who can talk a game out with you and just go back and forth. Even when you’re not on the same page, it’s nice to hear other people’s perspective.”
Damato and Piemonte’s upbringings were similar — they’re only children, have gambling grandmas, and are Chicago through and through, especially Damato’s accent. He had been covering Chicago sports and working on a podcast, and the two had long known each other when he reconnected with Piemonte at Gibson’s, a famous Chicago steakhouse.
Piemonte expressed interest in doing a podcast with him, something Damato called a “timing godsend” because he had long wanted to pivot more to sports gambling. They did it for a short while on Facebook Live, drawing up to 5,000 viewers at one point, and reconnected once more after a short hiatus.
“He’s the one person that I can spend every single day with and not get annoyed or aggravated,” Damato said of Piemonte. “We just gel. We’re very similar, we’re both very outgoing, we both love to gamble, we both love sports to death.”
There is a simmering intensity between the two, but it gets expressed in a jovial way. Piemonte and Damato are constantly in conversation — scanning potential plays, talking numbers, checking odds, and exchanging ideas — and their confidence in letting the other fill the conversational space quickly sold Denevi. The trick was getting Damato, whose day job was his primary source of income at the time.
“What everyone doesn’t understand is that when you’re launching something like this, the people that are next to you are the most important, but they need to be secure,” Piemonte said. “Not mentally, but emotionally and financially. And it’s hard. I’m looking at [Anthony] like, ‘We’re going to fly to this game,’ and he’s like, ‘Bro, I have work. How can I do this?’”
The show performed well enough — Damato said they had never done more than one take for each of their first eight episodes — that Betr brought Damato aboard as a signed personality, giving him a full-time paying job doing what he loves.
On parlays and responsible gaming
Piemonte wants Betr to be a place where responsible gaming is in the foreground, and he believes it can be done. He will have a seat on Betr’s board of directors and has already been successful in one key point of persuasion in talks with Levy: Betr will take no credit card deposits.
“A lot of people who are 25 and younger might be trying to bet outside their means, and we’re going to find a way to limit that,” Piemonte said. “How we’re going to do it, I’m not sure. … I do think about that often and I tell people don’t bet with money you can’t afford to lose.”
Despite being someone whose social media status has been elevated in the sports wagering space through his parlay wins — most notably that $3 million payout in September — Piemonte has taken pains with varying degrees of success to remind his followers there is more to sports betting than parlays. Perhaps most importantly, he has tried to impress that straight-event wagering is the better way to build a bankroll than pinning one’s hopes on a five-leg parlay.
“When I’m gambling, I’m putting myself in position for freerolls because I believe freerolls are wins,” he explained. “If you’re able to freeroll a bet, that’s the way it should be. I shouldn’t have to stress a four-team parlay to be even for the day.”
Piemonte has turned down offers from multiple sportsbooks to do promotions, though he did sign on with PointsBet for a “Bet Like Marco” promotion because the winner getting a $100,000 free bet meant “someone was going to make a bet just like me.” Pitching promotions is more about the free advertising for his car dealerships and brand-building.
Piemonte isn’t the only businessman who leverages an interest in sports and sports wagering to further his business interests. In Houston, Jim “Mattress Mack” McIngvale recently claimed the biggest all-time payout when his futures wagers on the Houston Astros to win the World Series across multiple states resulted in a $75 million payday that helped cover a furniture giveaway promotion at his Texas-based furniture store.
Piemonte acknowledges his giveaways of free bets, free cash, and the occasional Rolex or automobile are unorthodox ways of promoting responsible gaming, but it’s his way of giving back to “the community of people that support me.” He added he only does promotions that do not require a bet to win because he “doesn’t want to push people to gamble who shouldn’t be gambling.”
What the future holds with Betr and beyond
Piemonte, whose sports wagering persona changed dramatically in terms of attention following a $1 million payday in December 2020, may soon see another seismic shift.
This month, Betr gained access in Indiana through an agreement with Caesars Southern Indiana (CSI). It will also be in Ohio when the Buckeye State launches wagering Jan. 1, thanks to a partnership with the Pro Football Hall of Fame.
Betr will be CSI’s first online skin, but carving out market share against 15 other mobile platforms — even as a distinctive entry focused on microbetting — will be a challenge. Piemonte sees these as the first of many steps Betr will take, but he has yet to completely frame how the landscape will look in the short and medium term.
“I would be shocked if a year from now Betr is not launched in five or six states,” he said, ticking off other goals of Betr launching in all states currently with sports betting and having the 100x Club in the top 20 of all podcasts. “I will travel to those states to launch the brand. I will be doing whatever I can whether it’s seminars to help people understand gambling, tutorials online to coach them on how to do the things the right way or the wrong way.”
A focus on microbetting means a focus on in-play wagering, which includes solving the technological challenge of reducing lag time from live action for the next wager. It was something FuboTV attempted without success, shuttering its sportsbook in October. Piemonte noted the need for “working on the experience of watching the game” — to him that means cutting the lag to where the platform is 10 seconds ahead of a televised event — and hinted Betr may eventually purchase rights to events to help the media side grow at a faster pace than the sportsbook.
Piemonte and Damato appear poised to deliver that growth, with the latter confident Betr’s social media presence will prove a difference maker. But there is still some wide-eyed amazement in the moment. Both recounted being overawed with the attention they received during a recent trip to Arizona. Their time in the limelight left them realizing there’s a fan base looking to interact with them.
“I love sports betting. I go to bed looking at sports and I wake up looking at sports. It’s what I love,” Piemonte said. “That’s what I’ll always enjoy doing and I want it to be around for a long time, so it needs to be done the right way.”
In-story photos and videos by Chris Altruda