5 Leadership Lessons from Entrepreneur Larry Levy

By Bill Rudnick, Senior Partner and General Counsel for Cresset

Most people know Larry Levy as the Co-Founder of Levy Restaurants, the largest provider of sports and entertainment catering in the country (if you’ve been to a professional sporting event, you’ve likely enjoyed Larry’s food). But Larry is much more. He is not only a visionary entrepreneur, he is also an ethical business leader, a charitable philanthropist, and, to me, a friend of many decades.

One of my favorite memories of Larry is from 10 years ago when I was his guest the first time the Yankees played the Cubs at Wrigley Field. It was memorable not only to be sitting behind the Yankees’ dugout during a historic game, but also to see a man in his element … to be surrounded by his passions in life. Indeed, the only thing missing was a rock concert during the 7th inning stretch.

Cresset recently hosted a virtual program as part of our Cresset Founder Series during which I had the chance to ask Larry for his thoughts about his journey from entrepreneur to CEO to chairman. Passion was clearly a theme. I am pleased to share my five takeaways from that conversation:
1. Culture matters

As Larry says, “Culture is the single most important thing in a company, and it starts with leadership.” Culture isn’t just some “nicety” you reference during new employee orientation and then forget about. It should guide everything you do as an organization. Larry stresses the importance of understanding and communicating organizational culture, and then only hire staff who embrace and embody that culture. He is a believer in hiring people who are attracted to an entrepreneurial atmosphere. As Larry puts it, “Growth and entrepreneurship are aphrodisiacs. People love working for the winning team.”

2. Be open to new opportunities

Larry didn’t set out to create the largest sports and events catering company in the country. However, he was (and still is) an entrepreneur at heart. Forty years ago, when he and his brother saw the opportunity to revitalize a Jewish delicatessen on the seventh floor of Water Tower Place in Chicago, they did it for the challenge, not because they wanted to run a deli for the rest of their lives. That opportunity would be the genesis of what would become Levy Restaurants, which today is an international organization with more than $2.5 billion in annual revenue and over 35,000 employees.

There have been many other examples throughout Larry’s life when he seized on unexpected opportunities. Larry reminds us to be open to them. Look around corners. Be excited for what could be, even if it doesn’t necessarily align with what is.

3. Be prepared to evolve as your business grows and scales

Going hand-in-hand with embracing new opportunities is the need to evolve as your business grows. Larry didn’t know what that delicatessen in Water Tower Place he first walked into 40 years ago would one day become, but he did know it couldn’t stay what it was. As he searched out new opportunities, new markets, new business ventures, he ensured that the structure and operations of the business evolved, too. Levy Restaurants would not be what it is today if Larry hadn’t been willing to challenge the status quo and let go of tried-and-true ways of doing business. Yes, change can be unsettling, but it is the lifeblood of any business that wants to grow and thrive.

4. Know what you’re good at … and what you’re not so good at

No person can do it all, certainly no one in a business that is growing and expanding. Larry understands that reality well. As Larry explains it, he is the “ultimate delegator.” He has learned what he’s good at … and what he’s not good at.

For example, Larry knows he’s good at selling, but not so strong as an operator. He long ago learned to delegate and trust his colleagues to own those responsibilities (such as operations) that are not his strong suit. His business thrived because of it.

But for delegation to work, trust must be earned … just as there has to be a willingness to place trust in others. That foundation of trust goes back to company culture, and a sense of shared ownership in a company’s mission and vision. Everyone on the team must be heading in the same direction, with a sense that they are in a position to help move the company in that direction. When employees feel that, they are all in.

It all comes down to doing what you love. As Larry says, “When people ask me what I should do, I always say, ‘What are your passions?’” That has been Larry’s guiding light throughout his career.

5. Be vulnerable

Just as no one leader can do it all, nor can they know it all. Admit when you’ve made a mistake. Own (and share) your failures. Ask for help and ideas. In short, be human. Teams like strong leaders, but they love leaders who are honest and real.

For Larry, that vulnerability took the form of knowing he wasn’t emotionally ready to sell his business when first approached by the eventual buyer (Compass Group). He had poured himself into Levy Restaurants for decades. He knew it would take time to emotionally prepare to let go. It took him nearly two years to get ready, but when that day came, both he and the business were prepared for the transition. That honesty resulted in everyone involved being better off in the end.

During our discussion, Larry also showed another vulnerability. When I asked about his mom, he choked up. He shared the impact she had on his business and how much he missed her. In short, he shared that he is human.

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About Cresset

Cresset is an independent, award-winning multi-family office and private investment firm with more than $45 billion in assets under management (as of 04/01/2024). Cresset serves the unique needs of entrepreneurs, CEO founders, wealth creators, executives, and partners, as well as high-net-worth and multi-generational families. Our goal is to deliver a new paradigm for wealth management, giving you time to pursue what matters to you most.

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