One-Time ‘Bro’ Gary Vee’s All Grown Up, But Can DraftKings Marketing Keep Up?

DraftKings is getting the best version of Gary Vee. I’ve been around Gary Vaynerchuk, more commonly known as Gary Vee, since he was shilling wine. Then he became a marketing thought leader and in-demand keynoter. Finally, he became a cultural phenomenon. This is where DraftKings, daily fantasy giant turned sports betting and casino operator, picks up the ball in Vee’s storyline.

On Sept. 10, DraftKings announced its new NFL show, GaryVee’s Die Hard Dialogue.

My first thought was:

Uh-oh. That’s not good. Does this mean DraftKings is changing into yet another ‘bro’ sportsbook?

I’m happy to report that I was wrong.

However, DraftKings hasn’t yet reached the end zone. With a few more tweaks, maybe Vaynerchuk can help get them there.

Why I was wrong about Gary Vee’s impact on DraftKings

Vaynerchuk’s show is inclusive in almost every way – from gender to race representation and from professional sports commentary to fan opinion. The one place the show falls short in this regard is that most of the female guests are young, even though Vaynerchuk himself is 45. Online sportsbook bettors are generally younger men, so Vaynerchuk could argue he’s designing the show for DraftKings players, but the male guests weren’t quite as young.

Vaynerchuk has said he has learned the most about the zeitgeist from younger people. He mentioned teenagers, specifically, during a marketing keynote which I attended about 10 years ago. He told marketers that he liked to look over teenagers’ shoulders to see what they were doing, because they were almost always the first ones on a trend. In his example, they were early adopters of Instagram.

However, DraftKings Sportsbook got the new version of Gary Vee. He’s not the same guy who used 40 to 50-year-old women on Instagram as fodder for a cheap joke. Here’s the before-and-after:

At a 2014 Q&A session with The Lamp Post Group in Chattanooga, TN, he told an audience member that her mom was now on Instagram. He warned her not to spend her marketing dollars there, because her product was for younger people. That social media platform no longer catered to the audience she was trying to reach. To make his point, Vaynerchuk’s punchline was:

Cougar selfies, everywhere!

On the new show, hosted on the DraftKings YouTube channel, he also emphasized the age of his co-host, Jessie Coffield. She’s 30. However, unlike previous times in his career, he wasn’t invoking a lazy stereotype. This comment was relevant to the show and the subject. It had to do with Coffield becoming a New England Patriots fan as an adult.

Gary Vee and DraftKings are more intertwined than the show

In June, the podcast and YouTube video series Props & Drops debuted – starring DraftKings Co-founder Matt Kalish and Gary Vee. As of Tuesday, there were six, one-hour-long episodes on Spotify and the DraftKings YouTube channel.

In July, Ad Age reported DraftKings hired Vaynerchuk’s marketing agency VaynerMedia, which touted its ability to up the online gambling giant’s social media game. That, even though DraftKings Social went live the month before.

On Aug. 10, DraftKings Marketplace began, selling the NFTs that are among Vaynerchuk’s current passions. The marketplace can accept credit card deposits, but not cryptocurrency. However, DraftKings “is exploring” the possibility of processing cryptocurrency itself. It’s not clear how it hopes to do this while remaining in compliance with US regulations, but perhaps the company can find a workaround.

Few repeat viewers for Die Hard Dialogue

While the Spotify statistics for the podcast weren’t visible, the YouTube ones showed Episode 1 garnered 3,279 views, despite its warning that “This video may be inappropriate for some users.” I watched it: The warning seems mainly due to some salty language, and of course the gambling connection.

Because GaryVee’s Die Hard Dialogue follows the NFL schedule, there were three shows available as of Tuesday. During its first week, the 39-minute show heavy on New York Jets talk had 14,716 views.

As of Tuesday, the most recent podcast and show had 853 and 862 views, respectively. Of course, viewership of most shows declines over time, so some of the drop can be chalked up to natural causes.

Alternatively, it could be that the audience is tired of hearing about the Jets. (Vaynerchuk is a lifelong Jets fan who says he eventually wants to buy the team. However, he’s “only” a multimillionaire. The team’s current owner, Woody Johnson, is a billionaire. Forbes values the team at more than $4 billion.)

Or perhaps Vaynerchuk’s social media fans pay attention to him for non-sports-related reasons. He is considered a truth-telling, energetic and inspirational entrepreneur who shares career and life advice on social media. Vaynerchuk’s video with Tony Robbins, for instance, has more than 1.8 million views.

Gary Vee’s social media fame hasn’t rubbed off on DraftKings yet

If all of Vaynerchuk’s followers had tuned in to watch GaryVee’s Die Hard Dialogue, it would be a much larger audience. That crowd amounts to:

  • 15 million Twitter followers,
  • 9 million Instagram fans,
  • 9 million TikTok followers,
  • 5 million Facebook followers, and
  • 3.25 million YouTube subscribers

It seems that almost none of these are migrating over to the DraftKings shows.

DraftKings’ own social media engagement still leaves something to be desired. The DraftKings Twitter account has over 300,000 followers, and there are 121,000 subscribers to the company’s YouTube channel. However, those numbers are still only a fraction of the millions of players who use DraftKings Casino, DraftKings Sportsbook and DFS.

So it looks like Vaynerchuk’s still got a lot of work to do to get DraftKings more social media traction.

Gary Vee and DraftKings do have young audiences

While Gary Vaynerchuk and DraftKings do have younger audiences, they don’t necessarily overlap yet.

I met one of Vaynerchuk’s fans on Monday afternoon.

Philadelphian Reginald was my driver when I took a Lyft ride into Center City. Reginald, 28, said he started following Gary Vee on Instagram in 2017 or 2018, because he was “real” and helped motivate him to continue to strive to create his own clothing line.

Reginald knew about Vaynerchuk helping him achieve his business goals. He didn’t know about the DraftKings show, Vaynerchuk’s own apparel line or the social media influencer’s past. Out of the three subjects, Reginald was mainly interested in learning more about Vaynerchuk’s fashion line, which includes knit hats bearing Gary Vee’s quotes.

That’s the advantage of having younger fans. They don’t know about your past.

‘Attractive females and models only’

Reginald hadn’t even known about the time in 2016 that Vaynerchuk’s misogyny made it into Yahoo News. He was dismayed to learn that a party invitation to an event at the Cannes Lions International Festival of Creativity in France, hosted by VaynerMedia and Thrillist, included the following:

Please be aware this specific list is for attractive females and models only… Ladies, if you are interested in attending, please send us recent untouched photos and or your Instagram/Facebook links for you and each of your additional female guest [sic]. Once we have reviewed, we will send you specific entry details.

Reginald said the person who’d first told him about Gary Vee was a woman. He was relieved to learn Vaynerchuk had ultimately taken responsibility for the party invitation and apologized.

“That sounds more like him,” Reginald said of Vaynerchuk.

Online sportsbook demographics

DraftKings also has a young demographic. However, it’s less diverse than Vaynerchuk’s target audience.

According to Statista, as of March 2021, DraftKings Sportsbook had the whitest of all major online sports betting platforms, at 86%.

Quite the opposite is true of sports bettors across other channels. Only 19% are white, according to a March 2021 survey by the National Council on Problem Gambling (NCPG).  Asian-Americans hold the pluraity at 33%, followed by Black bettors at 32%, and LatinX at 25%. Granted, Asian-American sports bettors are more likely to place their wagers in person, but even by the standards of the online sportsbook world, DraftKings has a remarkably homogenous audience.

NCPG said the median age of online gamblers was 34 and 67% were male. About 73% of online bettors played DFS, while 41% bet on “traditional sports.” About 46% of sports bettors were under 35.

As DraftKings most likely wished when they hired him, maybe Vaynerchuk can help them change that. While Gary Vee’s specialty is social media, its users are aging – as he pointed out about Instagram, albeit in an unfortunate way.

Vaynerchuk explained:

Because my language isn’t a demographic, it’s a psychographic.

Heck, he’s aging, too. But he’s almost six years into his transformation into a more socially aware person.

Gary Vee, before he turned 40

When he was 35, Vaynerchuk was still looking for easy laughs, calling business attitudes “half pregnant.”

He made his cougar comment when he was 38. 

The sexist party invitation arrived in inboxes when he was 40 – but he took full responsibility for the faux pas.

A year later, Vaynerchuk wrote this:

If you’ve got the right DNA and you’re a 72-year-old female, you have just as good of a chance to win as a 27-year-old man. But, you’ve been trained and marketed to that a 50 year old can’t win.

(I would point out that you used to be one of those marketers, Gary Vee.)

VaynerMedia’s staff is half-filled with women, said Claude Silver, who appeared to be the only older woman in the International Women’s Day 2018 video about Vaynerchuk’s agency. It appears to be the only episode of the DailyShe – a pun related to DailyVee – about which former agency staffer Katherine Killeffer made some interesting comments.

DrafKings vs. the bro sportsbooks

Vaynerchuk has his work cut out for him in the online sportsbook space – especially when it comes to attracting women to the pastime.

Talking about US online gambling overall, Michael Daly – CEO of Catena Media – said online operators need to be careful about the influencers they pick, regarding what message that choice sends and whether it’s to their intended audience. He noted that influencers with “underage” fans might not be the best brand ambassadors, for instance. (Note: is part of the Catena Media network.)

Speaking during the same Sept. 13 webinar, Anna Sainsbury – chairwoman and founder of GeoComply – said operators must also think holistically about the market. They may not be the ones doing the inappropriate things, but they’ll have to answer for them. The public doesn’t compartmentalize its perceptions.

You see, there are online sportsbooks out there that make a specific effort to appeal to young males. Those efforts can appear sexist, perhaps alienating women bettors.

Sexism in advertising

Then there’s the DFS ad history of DraftKings and its longtime rival FanDuel. In 2015, our sister site – Legal Sports Report – wrote about how few women were in the ads and if they were, they were losing bets.

However, it’s even more difficult when a brand is fighting with itself.

For instance, MaximBet Sportsbook is a partnership between Carousel Group and the men’s magazine, Maxim. On Monday, though, Maxim reported this story, “Supermodel Nina Agdal Shares ‘Naked’ Mirror Selfie.”

A week ago, a MaximBet spokesman had happily contacted me to gain further coverage about the app, because:

MaximBet is announcing that every female student athlete in Colorado – across every division, school and sport – will receive an NIL [name, image, likeness] deal of cash + merchandise as a way to promote female athletes. That means every female student athlete in Colorado – Division I-III – will get paid for playing a sport in college. It’s the first time any brand has offered NIL exclusively to women’s sports across all divisions.

Online sports betting’s complicated relationship with women

Look, I get it. We’re not the online sportsbook demographic. Women don’t bet on sports in nearly the same numbers or the same dollar amounts as men.

NCPG said it:

Men are much more likely to bet on sports than women, by a margin of 28% to 12%.

However, I’m not sure if what’s the chicken here and what’s the egg. I don’t want to give my money to someone who treats me like a piece of meat – or worse, expired meat. (Remember: “Cougar selfies, everywhere!”)

Speaking with other women, I often hear the same sentiment. It’s cringeworthy, for example, for a woman to win a poker tournament and be congratulated by “booth babes.” Uh, thanks, ladies?

So as cool as it is to see actors and comedians Martin Lawrence, 56; and Kristen Schaal, 43, as the stars of the DraftKings Sportsbook commercials, that representation of  audiences other than young, white men has to be reflected elsewhere.

In general, online sportsbook marketing has to dig deeper if it wants to attract women, minorities and anyone over 34.

Step one: get some older women on the the show

In DraftKings’ case, I think that means at least having 50-plus year old women on GaryVee’s Die Hard Dialogue videos with the same frequency as men in that age group.

In other words, DraftKings and Vaynerchuk have to make their words match their actions.

Vaynerchuck has shown that he’s on his way.

Back when I encountered him at marketing conferences, he would tell me he couldn’t accept a speaking gig for less than $30,000, because of a promise he made to his wife to not accept jobs for less. Then he’d say something sexist and ageist during that expensive keynote.

Vaynerchuk’s actions now align better with his words than they once did. At this point, the ball’s in DraftKings’ court.

About the Author

Heather Fletcher

Heather Fletcher

Heather Fletcher is Lead Writer at Bonus, concentrating on online casino coverage. She specializes in breaking news, legislative coverage, and gambling marketing strategy overviews. To reach Heather with a news tip, email [email protected].
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