VENTEUR spoke with Jeffrey Zuckerman, chief executive officer of Main Street Events, a leader in fashion industry and trade show events. Zuckerman leads a dynamic team of live events professionals, offering personalized trade show experiences. One of them is ILOE STUDIOS, an expertly curated fashion event that works directly with the women’s apparel and accessory market to create a unique exhibiting and buying experience.

The Journey

The entrepreneurial journey is one of self-discovery. What have you learned about yourself while building your business?

As the leader of a family-owned business, my entrepreneurial experience has been deeply personal and formative. Growing up in the business allowed me to contribute to its success and experience its challenges from an early age. But I also gained valuable business perspective in law school and through collaborating with other brands that I could then share and help advance our work in meaningful new ways.

In all these experiences, I learned that I needed to develop a strong gut for change – in other words, being comfortable with being uncomfortable. If there is one thing entrepreneurs all agree on, it is that there will always be uncertainty and change. No matter how great the business strategy, product, or message, no one is immune from what I call the “sucker punch,” an unforeseen challenge that changes the game. COVID is a prime example that challenged many entrepreneurs and business executives alike.

While these moments in time are often stressful, I learned that they could also be clarifying and to embrace challenges as opportunities for innovation. I also learned to maintain focus on the big picture as a leader and that I enjoy motivating and collaborating with specialists throughout our business to achieve our vision across multiple pathways. 

The entrepreneurial journey is often lonely. Have you experienced loneliness as an entrepreneur, and why? 

Many entrepreneurs, myself included, experience loneliness because of the sheer magnitude of the responsibility we carry on behalf of the business. I think it is hard for people to truly understand what it is like to build a business and have a team that is depending on you to achieve success. There is pressure to be “always on” and to have all the answers. But there isn’t always another product line or business unit that can absorb slow growth or a failed launch, for example. Unless you’ve sat in the captain’s chair yourself, it can be hard, if not impossible, to truly empathize with the entrepreneur navigating their team through such a sea of uncertainty. 

I’ve found that having a trusted confidant is critical but much easier said than done. You never want to express self-doubt or doubts about the business, and many people are counting on you to be the perpetual optimist to maintain their motivation through tough times. It’s important to find someone who can be a sounding board to help you see the forest through the trees in these situations.

What role has intuition played in your success as an entrepreneur, and why do you think this is the case? 

Trusting your intuition is imperative. There are rare occasions where you have all three gifts of time, money, and information to develop a perfect solution or plan to the many challenges and opportunities that come with entrepreneurship. You are often required to take decisive action quickly and without all of the necessary information to maintain your competitive advantages. You must be prepared to make the call regarding whether a decision must be made now or if a second look is needed. In either case, you need to develop a strong gut and learn to ask the right questions to adequately assess your risks and make the most of any situation.   

The Psychological Warfare

Entrepreneurs generally sleep less, work more, and let their health slip. This combination, combined with loneliness, often results in insecurity, self-esteem issues, and low self-worth. Have you experienced any of these issues as an entrepreneur, and why?

Your work life is omnipresent as an entrepreneur. You’re investing your time, money, body, and mind into the business, making it hard to focus on other aspects of your life. There is also a lot of pressure on the entrepreneur to regiment their lives for the sake of the business. The truth is that there isn’t a one-size-fits-all solution to entrepreneurial work-life balance. You have to find a routine and lifestyle that prioritizes your business and integrates into other areas of life that bring you fulfillment.

Entrepreneurs can become easily disconnected from other things that should matter to them when they are hyper-focused on their projects and business. Moreover, entrepreneurs lack the security of a big corporation and are required to fully own these projects in ways that friends and family may not understand. Imagine getting a good night’s sleep with this kind of weight on your shoulders! It can be tough and lead to even tougher days. That’s why an all-or-nothing approach to entrepreneurship rarely works. You must find ways to care for your physical and mental well-being as diligently as you care for the business.  

What is the most unrelatable part of being an entrepreneur, how does this impact your mental health, and why?

It’s not unusual for entrepreneurs to center their business and leadership as central to their personalities. Entrepreneurs often derive their self-value from their success in business, which means setbacks can be deeply personal and devastating. Losing perspective on the other aspects that make you successful in life can leave you isolated and feeling like a failure when things inevitably go wrong. Building a business isn’t easy, but when your identity and value come from the business, you can get a disordered view of your life and become quite jaded.

The Mistakes

What is the most significant mistake you made early on as an entrepreneur, what did you learn from it, and how can others avoid it on their journeys?

The truth is that I’ve made a ton of mistakes building our business, but one hiring mistake stands out. I learned that relationships and skills are only part of the puzzle regarding aligning your business with the right individuals. What I had overlooked was in prioritizing a cultural fit for our team.

Everyone you hire is an extension of your business and, thereby, an extension of yourself. You must make sure you have great specialists around you to effectively serve as a leader. Still, it’s equally important to ensure those specialists can work together as a team, find shared understanding and commitment to the business strategy, and make the business stronger and more effective. If a person is great at their job but otherwise deficient in working as a team or brings a negative attitude, they can gum up your systems and become significant detractors. 

What do you see that is often overlooked by entrepreneurs you encounter, and how can other entrepreneurs be aware of this from the beginning?

As a licensed attorney, one of the biggest mistakes I see from other entrepreneurs and business leaders is overlooking the value of building their businesses and, importantly, business relationships on a strong legal foundation. Failure to create a shareholder agreement could spell the doom of the business if and when partners disagree.

The Successes

What seemingly insurmountable obstacles have you faced as an entrepreneur, and how have you overcome them? 

COVID-19 and its broad financial impacts are likely the largest obstacles that every business owner – large and small – has faced in recent history. To survive, we went back to our roots as a company, made some hard decisions, and doubled down on our customer relationships, treating everyone with empathy and respect no matter the challenges we were facing at the time. That decision allowed us to maintain our position in the market and begin our recovery sooner than others. We are very grateful to all those who stood by us and allowed us to do the same for their businesses throughout such a tumultuous time. 

The Advice

What advice would have made your entrepreneurial journey easier, and why? 

First and foremost, find a confidant – someone you can trust to tell the truth and have them speak the truth to you no matter what. They will help keep you honest with yourself while also helping you expand your perspective and challenge your preconceptions. Also, find a good lawyer to help you navigate the legalities of starting and operating a business. Often, a good setup with solid contracts can make all the difference in the long run.

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