How Serial Entrepreneur Jennie Enterprise Builds Successful Membership Businesses

The mastermind behind one of New York City's most prestigious private membership clubs offers a few lessons on turning your business into a one-of-a-kind destination.
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Jennie Enterprise is not just the mastermind behind one of New York City’s most prestigious private membership clubs. She is also a serial entrepreneur who has created one successful venture after another.

As a teen, Enterprise noticed that her local community lacked a tennis program for kids, so she started one. She recalled that she borrowed $100 in May, and by September had made $10,000, calling the entrepreneurial experience addictive.

Later, as a student at Fordham Law School, she won a business competition, creating a coffee shop and entertainment venue concept. The venue not only booked solid but eventually expanded to multiple locations. This concept gave Enterprise her next idea, which would eventually become Reebok Sports Club.

Related: 5 Things the Best Leaders Do Every Day

Her most recent success, CORE: club, offers its 1000-plus members lodging, dining, culture programs, movie screenings and a home base from which to work, train with a personal trainer, get a spa treatment and more, for an annual fee of $17,000 plus a $50,000 initiation fee. For those of you running the numbers in your head right now, that’s almost $1.5 million in revenue each month. 

I recently met Enterprise at CORE: to discuss her entrepreneurial success. Here are a few lessons from her on turning your business into a one-of-a-kind destination, particularly for those with membership or subscription-based business models.

Be an observer.

During the internet boom, Entreprise noticed a major cultural shift, especially in New York City. Innovators and world changers were starting to come from everywhere, not just certain Ivy league schools or major cities. As “global citizens” emerged into the marketplace, so did their unique needs, such as a place to call home while abroad. This new breed of entrepreneurs and executives didn’t just need a place to sleep and eat, they also needed an inspiring, familiar place to hold meetings, exercise and take in culture. Thus, the idea for a new membership club was born. 

“We [created a place where] people can work and play and accomplish and change the world and interact and intersect with ideas and culture and a curated community of people,” said Entreprise.

Multiple industries are currently in disruption, which means plenty of new audiences and new problems for entrepreneurs to solve -- if they’re paying attention.

Seek out your ideal customer.

Enterprise had a specific global citizen in mind to join CORE’s “curated community.” With that person in mind, she began selecting 100 ideal candidates to not only become members but also partner in the creation and funding of the club itself. It was an ambitious idea, to be sure, but this was late 2001, and one had to be creative when fundraising in the months following Sept. 11.

Thinking of the specific world changers she wanted to invite -- and sell to -- Enterprise worked with a team of renowned designers, architects and writers to create a brand book to present to prospects. It would have been easier to lower her standards for the club or its members, but instead Enterprise took her time.  

“It wasn't easy. It took three years to get the founding membership together based on the economic environment and the meticulous nature of the [way we invited them]," she said, explaining she wouldn’t call herself patient, but she does consider herself very disciplined.

“We've really built the business one member at a time.”

Related: 5 Keys to Entrepreneurial Success in 2017

Be intentional from the start.

Enterprise didn’t simply send a pitch deck with brand messaging and architectural renderings. Insead, she worked with a team of artists to create a now-famous white box, in which the brand book was placed. The mysterious, unique, white boxes were then sent out to specific A-listers from someone they knew and respected, not from the CORE offices.

“Identifying 100 people from 13 different industries to represent the diversity we were looking for was critical.” she explained. “How would we, literally, get in front of them to capture their imagination? So we really created what is now an infamous white box that represented, essentially, a piece of art -- a really interesting manifestation of the brand.”

Whether you’re approaching investors for a brick-and-mortar business or trying to get early adopters to download your app, the initial ask needs to reflect the quality and experience of the product or promise itself.

Create their ideal experience.

CORE club offers the world traveler -- or even a New York commuter -- everything they could need to be able “to literally spend from early in the morning until late in the evening and, essentially, have a seamlessly integrated life.” Enterprise thought through literally every aspect of their life in order to provide a one-stop solution. She didn’t stop at function, though. Form was equally important, knowing her customers have an eye for aesthetics.

“The way we think of our world is we have the hardware, a collection of architecturally interesting spaces infused with culture, and then we have experiential architecture, so that's the activation of the space.”

If you want to create a go-to destination for your customers, online or off, make sure you think through the entire experience. A slow-loading home page or one grumpy hostess could be a deal breaker in today’s competitive market.

Assemble a stellar team.

Enterprise worked successfully with multiple architects, which is usually a recipe for disaster. The key to assemble a stellar, creative team -- and get them to work together -- is to focus on collaboration, she says. As the leader, you need to constantly calibrate processes and over-communicate to team members.

“You set a vision, but a lot of what you're doing is providing the conditions for bringing out greatness in others” she explained.

Now she manages a team of about 80 employees, all of whom have been educated on a set of essential “Core Love” guidelines on customer service. 

Related: 5 Ways to Build a Team that Cares

Stay mission-focused.

Enterprise explained it’s taken her all, for years, to get her operation off the ground, and now manage the many moving parts day to day. I asked her about work/life balance, wondering if she gets burned out.

“It continues to be exhilarating, and that's something that I think everybody should be privileged enough to experience in life,” she answered. “Every day you're super excited to wake up and super excited to attack the day. And that doesn't mean it's easy. It's quite the opposite of easy, but it's the way you look at your mission . . . . You just have to have this singular focus.”

Stay an observer.

Enterprise admits she may or may not have an information addiction problem. She has  TVs, spends her early morning scanning rss feeds and even has an intelligence program built around her members. She believes the key to retaining members and keeping them engaged is to have your finger on the pulse of how they are living their daily lives. That includes monitoring not only today’s news and culture, but also the industries and markets that matter most to them. This is one of her pieces of advice for aspiring membership/subscription-based entrepreneurs.

“Whether you're Netflix or you're somebody else that is looking for an addictive community of readers or eyeballs of any sort, I think [you need] a true authentic, relentless pursuit of relevance to your audience.” she shared. “And you always have to pay attention to your own cultural infrastructure so that you truly are in relentless pursuit of your mission.”

Watch more videos from The Pursuit on the show's YouTube channel.

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