I had the pleasure of sitting down with the charming, elegant and insanely driven Jennie Enterprise, founder and CEO of the ultra-exclusive CORE: club in mid-town Manhattan. Home to an array of personalities from billionaire tech CEOs all the way down to mere millionaires from the world of fashion film and finance, CORE: founding members include Blackstone chairman, Stephen Schwarzman, real estate mogul, Steven Roth and agent to the stars (and Entourage inspiration), Ari Emanuel. Our interview took place in Jennie’s ‘office’, which also happens to be the best corner table at the club’s second floor dining room.
For a woman who’s never taken orders in her life – she established her first business at 13 – Jennie was the perfect hostess, making sure I was well fed, watered and generally taken care of throughout our interview. It’s easy to see why the great and the good flock to CORE as a sanctuary of peace and beauty in the middle of this uncompromising city.
For those with shorter spans of attention, I’ve included a summary of Jennie’s advice up front – but see below for a larger slice of the interview.
Jennie Enterprise’s five steps to entrepreneurial success:
1. If you want your idea to succeed you have to be fanatically obsessive about it
There’s a chance others may view you as delusional, there’s a strong likelihood that your version of reality will differ from the established view, but for your idea to succeed you need a complete commitment, an obsessive commitment, a fanatical commitment to the mission and a notion that your view of the world is one that needs to be to pursued.
2. Couple velocity with reflection
Move fast and with unshakable determination in the pursuit of your vision, but make sure to pause once in a while and stress test the heart and soul of your mission.
3. Ask the right questions:
Part of this reflection exercise is to make sure you’re asking the right questions. Never wonder whether you can do it and never ask anyone else if they think you can do it! Ask them instead, “how can I optimize the value of what I’m creating?” So I would always want to understand how CORE: could make a difference in somebody’s life. Ask them what isn’t working in their lives currently, ask them what will make their lives better, ask them how they think about their lives within the context of your idea. This will help you reflect and evolve your vision.
4. The idea is important but inspiration and execution are more important:
There are three components to implementing a successful idea: the strength of the idea itself, inspiring others to buy into it, and executing against the idea. Ultimately you need a little bit of all three but the underlying idea is actually the least important piece. You can have the strongest idea in the world, but it’s meaningless without meticulous execution and people who are motivated by the mission and want to be a part of it.
5. Success comes with peripheral vision. Be humble and have a sense of humor:
Yes you need to be obsessive, yes you need to be fanatical, but you also need empathy and fundamental kindness. Simple as it may sound, you cannot overstate the importance of being nice, staying humble and having a sense of humor. This will get you and your team through the hard times when it may be difficult for those around you to stay positive.
Check out more of Jennie’s insights and wisdom below:
Dan Simon: What was your inspiration for starting this business?
Jennie Enterprise: I seem to have a predisposition for business models where I can unleash the magic of emotional engagement. As I found success in this space, I continued to move in the direction of subscriptions and memberships. I believe that if you are ultimately and authentically passionate about what you’re doing and that enthusiasm is contagious, you can essentially deliver against any need. I have always been captured by the imagination of bringing a sense of community through interesting spaces, compelling programming, and inspired food and beverage platforms. There are these elements of activating other people and creating a level of happiness and in many ways of seamlessness to their lives that I feel is important. I think the ultimate inspiration for many of the businesses that I created is what I call “experiential architecture.”
Simon: What qualities do you have that have helped you make this successful?
Enterprise: I have always had a fascination with accomplished people. I think the interest for me was the idea that there were people on this planet that were able to somehow gain enough power and influence to make a difference. I had an awareness that I could control my own destiny from a very young age, and I think that that was really exciting for me. I was naturally drawn towards accomplishment. I have always been a respectful person and the feeling of mutual respect is something that I have fostered at CORE:. We really don’t have rules. We actually provide conditions for transformation, which means that people can conduct the business of life here. There’s a real natural organizing principle of respect.
Simon: How important is it to come from a humble background?
Enterprise: I believe that challenges are gifts and puzzles you have to solve. I wouldn’t trade my background for anything because I have learned from the example set by others that hard work is critical. I grew up with an incredibly hard working father, and I was very fortunate to have that example. I also learned throughout my life that it is just as important to see behavior that you may not want to emulate. I think that it is just as profound and powerful to say, “You know what? That doesn’t make me feel good and I don’t want people to feel that way, so I’m not going to do that.” I definitely feel like a large part of who I am is really rooted in hard work, humility, and being really grateful for the opportunity to get to do what I do every day. Most of your day is filled with puzzles, and yet it can be a really fun thing to do when you realize that’s what you chose to do.
Simon: Having never worked for anyone else, how do you solve problems?
Enterprise: In a business environment you are never doing anything by yourself. From my experiences in college to when I was a part of the team that created Reebok Sports Club, I have realized that you don’t get to do what you want to do every day unless you are making people happy with the experiences you are creating. The experience you’ve created is just as important for your team as it is for your audience that’s buying it. We have two communities here at CORE:. We have the CORE: partner community, which is employee-based, and we have our member community. The puzzle I have to solve is “How do I make the experience for both of these groups extraordinarily compelling?” I’ve thought about that similarly throughout every company that I’ve created. I think that a true entrepreneur has to feel like they are on a mission. Even if you’re creating a product, you still are working with people and you’re inspiring them in different ways. Steve Jobs may not have inspired people the way I would have, but he was extremely successful at bringing out greatness in people.
Simon: What are some of the most important elements to starting your own business?
Enterprise: You have to actively shape your idea; nothing is just going to happen. I think there has to be a fanatically obsessive approach to evolving an idea and bringing it to life. The underlying idea is probably the least important, and the execution is probably the most important. I think the connective tissue is the inspiration for others who want to be a part of it. You can never overstate the importance of being nice, being humble and having a sense of humor in my opinion. You have to be an eternal optimist. This will get you through the dark times when it may be hard for those around you to stay positive. The key is an unwavering commitment to that vision and a relentless inspiration to emotionally connect everybody to that vision.