Gary Vaynerchuk & Ryan Harwood: Pickleball, Omakase, Web3, & Media

Partnerships, though intricate, occasionally manifest magical unions. In early 2017, Gary Vaynerchuk, renowned as Gary Vee and the driving force behind VaynerX, executed the strategic acquisition and merger with PureWow under the banner of a new enterprise, Gallery Media Group. PureWow, an influential women’s multimedia platform founded by Ryan Harwood, catered to women in their 30s and 40s but found engagement from women aged 25 to 54. With an impressive overall reach of 90 million across all platforms, PureWow created content and experiences spanning every facet of active women’s lives. Under the Gallery Media Group, they also added ONE37pm, a countercultural community for men, with a reach of 20 million. The goal is to empower through shared content, experiences, and retail.

“I met Ryan many years ago through a mutual friend, Ben Lerer, as he was just entering the Internet publishing business at a Gawker Rooftop, New York City event and I got into a conversation about why he was coming into this world from the finance world. I just really liked his temperament and who he was. I got to know him on a personal level more over the next two or three years,” said Vaynerchuk. “I decided to personally invest in one of his funding rounds for PureWow because I had a good sense that he was building a real business and he was a real guy. I got closer to that business and to him as an investor, which led to me purchasing his company in January 2017. This obviously led me to really getting to know him as an operator, as a person. To me the two variables I look for are: is someone capable as an operator? And do I like them as a human being? Ryan is exceptional on both fronts, which has led to more and more opportunities.”

PureWow served as the conduit that brought these two remarkable entrepreneurs together. The journey from there to establishing a flourishing empire rested on the foundations of mutual respect, shared interests, and unyielding determination. Harwood elaborated on the matter, stating, “VaynerX serves as the umbrella for all our marketing, communications, and media enterprises. However, ventures such as the Jersey 5s, a Major League Pickleball team we acquired, and the hospitality company, reside outside of VaynerX’s purview.”

The decision to initiate a women’s community may have appeared unconventional for a man like Harwood. After graduating from Wharton, he embarked on a journey that involved playing D1 Tennis for UPenn and a brief stint in professional tennis before delving into finance. Disenchanted with the corporate world, he sought counsel from individuals in various industries. 

“I kept gravitating toward media and technology,” Harwood said. “I had a few friends that started businesses in this space. They were having a lot of fun and the space was growing fast. There was a lot of venture money pouring in at the time and I felt like this is interesting because I like technology on the surface — I’m not a coder, but do I like technology. I can be a business person but I can flex some creativity in this world as well — I never was able to use that in my finance job.”

Initially intending to launch a media company catering to men, Harwood recognized the saturated competitive landscape dominated by established digital media companies such as Vice, Bleacher Report, and Thrillist, which were competing with media giants like Condé Nast and Hearst. Pivoting his focus, he observed a relatively untapped market in the women’s space, with Vogue, Cosmo, and Marie Claire reigning supreme. However, companies like Refinery29 and PopSugar were beginning to emerge, competing intensely for the attention of young millennial woman. He began conducting comprehensive focus groups with women of varying age groups. 

“It was very clear that once women reached a certain age that they were being put in the category of mom regardless of whether they were a mother or not,” Harwood said. “It was interesting, and they didn’t like that. Even the ones that were moms weren’t happy about it.”

Harwood’s understanding of the women’s demographic, stemming from his close relationship with his older sister and upbringing around numerous women, enabled him to recognize the white space that existed. Thus, in 2010, he launched PureWow, employing content creators within the target demographic to develop captivating content. For the initial year and a half, he remained the only male among the team, reflecting the trust he placed in his team to maintain the integrity of the content.

Eight years later, Harwood decided to revisit the men’s space. At this time he felt that the space had an opportunity to be disrupted a bit, while carefully utilizing Vaynerchuk’s audience, which includes multi-millions of followers.

“Now I had Gary Vaynerchuk as my business partner and he had a massive audience of young men that worshiped him, and I knew that I could siphon that audience over to One37 and create a media property because while Gary technically is a media property of his own with all his following, it’s about his personal brand and what he believes in. I knew that I could take that audience and start writing about streetwear, emerging musicians, crypto, and sports cards and create an actual publication out of it using the base of his audience as a starting point,” Harwood said. “So it was both an opportunity to innovate after eight years of seeing a crowded market combined with the resources I now had at my fingertips. It gave us an advantage in the men’s demographic.”

Remarkably hands-off in matters concerning editorial direction and content curation, Vaynerchuk emphasized that as the chairman of the organization, he considered such involvement unnecessary. When asked about his involvement with the content of his brands, Vaynerchuk said, “Practically zero. I have no interest in really dictating the editorial. That is on the people who run those departments in Gallery Media Group and One37 specifically. Of course a couple times a year I might be excited about something that’s happening in the world but usually I put that out on my social media first anyway so there’s no competitive advantages for my publishing arm. So I would say I’m incredibly hands-off in that department. As the chairman of the organization, I feel like that’s the appropriate place to be. I’m aware that a lot of people use some of their publishing arms for advancing the way they see the world. I’ve got my own personal platform to do that and so I don’t need my publishing arms to do that for me.”

The subsequent years since the beginning of their partnership has witnessed Harwood and Vaynerchuk’s expansion into various experiential ventures, including PureWow’s House of Wow in Tribeca, where they host editorial events, thought leadership panels, client events, and shoots for influencers — to name a few.

With the media company doing well and growing, they began curating the applied side of the company. “We’ve gone very deep into experiential,” Harwood said. “So we have a whole events arm. We actually have a massive experience going on in the Hamptons from August 1 through Labor Day where we rented a house for Gallery Media Group, which is called Gallery Beach House. And we’re going to have rotating creators like musicians, athletes, artists. We have two pickleball courts. We’re going to have exclusive dinner parties with chefs and celebrity wellness instructors in the morning that we’re going to create tons of content out of.”

Among the innovative endeavors that merged hospitality and sometimes blockchain, Harwood’s silent partnership in the VCR Group stands out. The group launched ITO, an exceptional Omakase sushi restaurant, and Fly Fish, an innovative multi-level NFT membership restaurant in New York City offering exclusive reservations and access to entertainment events beyond dining, which is slated to open soon, as well as an upcoming project in Vegas.

Central to their partnership is Vaynerchuk’s expertise and prominence in the blockchain and NFT realms. His NFT offerings, collectively known as VeeFriends, reflect his “personality and legacy,” characterized by soft traits such as Empathy Elephant, Aspiring Alpaca, and Ambitious Angel. Through these characters, he aims to prioritize soft traits to counter the notion that success requires trampling others. 

“Gary wants people to prioritize kindness and empathy,” explained Harwood. “All these traits that he thinks are the things that make people successful, not the things that from the past we’ve always emphasized in order to get ahead — you’ve got to step on someone, for example. He wants to share that message through these characters.”

Building on Vaynerchuk’s extensive audience, they organized VeeCon, a super-conference uniting world-class speakers and thought leaders to shape the future of the industry through transformative experiences. The massive experiential endeavor was recently held in Indianapolis to much praise.

Undoubtedly, one of the most captivating dimensions of their collaboration has been their investment in the New Jersey 5s, a Major League pickleball team symbolized by their mascot, the Competitive Clown. The team name is sentimental. When Vaynerchuk was 5 years old he wanted a NY Jets jersey but his mom couldn’t afford to buy him one, so she knit him a jersey with the number five on it. 

While Vaynerchuk remained cautious about comparing the sport’s future to that of, say, Major League Baseball, he believes that pickleball’s potential for tremendous growth over the next five decades is undeniable.

“To be as big as MLB, I think is an incredibly big stretch,” he said. “I mean tennis is not as big as MLB. But do I think it could be extremely big over the next five decades? The answer is yes. I do play very rarely these days. I’m incredibly busy with family and business, but I do love the sport. I like playing it. I’m a hacker when it comes to tennis and ping-pong, so I’ve always liked racket sports. I watch them. I play them. And it was so easy for me to be involved because I’ve always paid attention to trends and I was aware that pickleball was starting to boom and I was watching the behavior amongst many people — not just the elderly like people like to think. And I also thought that the early videos I saw on social media and the early matches I saw on MSG Channel felt like a sport that people would want to watch — all of this was leading me to feeling confident that I jumped in.”

And they’re not the only ones jumping in. The league has garnered much attention recently with the likes of supermodel Heidi Klum, NFL’s Larry Fitzgerald, actor Eva Longoria, and “Shark Tank”’s Mark Cuban, holding ownership in their own respective teams.

Harwood said, “We were fortunate enough to know a guy named Amer Delic, who was a professional tennis player. He called me up for marketing help for MLP a couple years ago. And in passing he mentioned that they were selling teams and Gary’s always wanted a sports team. This was a perfect opportunity for us to own a sports team and understand how it works. So, we bought a Major League Pickleball team. Here we are a year-and-a-half later since buying a team. It’s like a whole new world from when we did it. Gary and I are co-owners in the New Jersey 5s and I operate the team. We already had the first season and had the number one female in the world on our team — her name’s Anna Leigh Waters, a 16-year-old female and unbelievable athlete. She’s going to be wildly famous someday.”

The partnership between Harwood and Vaynerchuk has organically matured, branching out into a myriad of exciting directions, thus nurturing a remarkable journey that both entrepreneurs cherish through mutual respect and friendship.

Ty Wenzel

Co-Publisher & Contributor

Ty Wenzel, a recent breast cancer survivor, started her career as a fashion coordinator for Bloomingdale’s followed by fashion editor for Cosmopolitan Magazine. She was also a writer for countless publications, including having published a memoir (St. Martin's Press) and written features for The New York Times. She is an award-winning writer and designer who covers lifestyle, real estate, architecture and interiors for James Lane Post. She previously worked as a writer and marketing director for The Independent. She has won multiple PCLI and NYPA awards for journalism, social media and design, including best website design and best magazine for James Lane Post, which she co-founded in 2020. Wenzel is also a co-founder of the meditation app for kids, DreamyKid, and the Hamptons social media agency, TWM Hamptons Social Media.