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Zachary Lezberg of Small Business Expo: “Preparation”

Preparation: be prepared for things that will go wrong. Have backup plans, backup plans for those backup plans, etc. A successful entrepreneur will always have multiple routes to the same final destination. Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, […]

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Preparation: be prepared for things that will go wrong. Have backup plans, backup plans for those backup plans, etc. A successful entrepreneur will always have multiple routes to the same final destination.


Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Zachary Lezberg.

Zachary Lezberg was born an entrepreneur. At the age of 11, he started his first business (a DJ company) and hasn’t stopped since. Today he is the Founder and CEO of Small Business Expo, America’s biggest networking and educational event for business owners, start-ups, and entrepreneurs.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I’m pretty sure being an entrepreneur is in my DNA, but I’ll get into more of that later. I went to the University of Miami, was a double major in film and theater with a minor in business management. My Mom was a well-known event planner in Boston. I got my creativity from my Mom and my strong business sense from my Dad.

While I was at the University of Miami I started a huge organization called Quantum Entertainment which involved film and theatrical productions on campus. It received one of the largest budgets from the University of Miami to a student-led organization and it is still flourishing even 17 years later. It’s actually one of the largest organizations on campus now and produces shows like “The Rocky Horror Show,” “West Side Story,” “A Chorus Line,” etc.

I fell in love with producing and was hired by one of the largest Broadway production companies in New York City which produced blockbuster hits like, “Wicked” and other great shows. I also did casting for NBC’s hit TV show, “Fear Factor,” and also worked for Universal Studios production group, so I guess you could say I’ve been around creativity and production my entire life.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

After working for the Broadway production company in New York, I realized there needed to be a big business networking event to bring together small businesses. When I was in New York, I launched a show called ShowBiz Expo in 2008/2009 which took place in New York and Los Angeles and it was the largest national networking event for show biz professionals (directors, producers, actors, writers, etc.). Just like I saw what happened with COVID, I noticed many people losing jobs who were trying to start their own small businesses. So I decided to launch Small Business Expo and it took off like wildfire. It was a perfect fit for my production experience and I started it in New York, and then took it to Los Angeles, Dallas, and Miami. And it continued to grow. Now it is in 45 cities across the country and we have an email list of 1.2 million passionate business owners. Small businesses need a place to network and build relationships.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

There’s no doubt I am a natural-born entrepreneur. I have always had a passion for running a business. In fact, I started my first business when I was 11 years old. It was called Dreams To Reality and it was a DJ company where we would DJ at events like high school pep rallies, dances, birthday parties, bar mitzvahs, etc. At one point I even had three dancers. I think being an entrepreneur is innate for some people. Others have great ideas but are unwilling to take that risk. You have to have passion, patience, and persistence to be a successful entrepreneur.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

I got my creativity from my Mom and my business sense from my Dad — I still go to my Dad for business advice. Though my mom passed away, I still know she is there giving me her guidance and expert creative advice. She always told me to go with my gut! The combination of having my Mom and my Dad as parents to guide me in my business endeavors was perfect. I remember the time I was producing and directing a huge production of “A Chorus Line” at the University of Miami, and I would go through my budgets and creative plans with my parents. They always offered valuable advice. Did I always listen? No. But hey, I was in college, and what better place to make mistakes?

What do you think makes your company stand out? Can you share a story?

What makes Small Business Expo stand out is that we are really the only big business event for small businesses in the country. There is nothing else like us on this scale. We operate like a franchise restaurant in that we always produce the same quality events. Regardless of what city we are in, people know exactly what they are going to get. Our model has proven to be successful.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Passion — you have to have passion for what you want to do. Believe in yourself and never get discouraged. Running a small business has major ups and downs. I’ve had times where I’ve gotten so discouraged that I asked myself “is it worth it?” In the end, it is. You just have to remember the passion that drives you.
  2. Doer — You have to execute your ideas. Lots of people are dreamers but are they doers? Are they willing to put it all on the line to make their business successful? If I had never acted on my idea of bringing small business owners together, I would never have had this successful company. It was taking action on my idea which created my success.
  3. Risk-Averse — Starting a small business is stressful. You have to be willing to take a leap of faith. You’ll have good times and bad, but the committed entrepreneur keeps moving forward no matter what is thrown at them. It is scary starting a new endeavor. There is a lot of risks involved. But that’s what separates entrepreneurs from wantrepreneurs, right? I took a risk leaving my full-time job in NYC to start my own company.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

I received advice from someone who was very wealthy at the time. He told me that if I wanted to do something, I should go out and get a bunch of credit cards and max them out and hope for the best. That was awful advice and I didn’t agree with it. It doesn’t teach you to be financially responsible, learn how to manage profit and loss, or properly invest toward your future. Had I taken his advice, I would have started my company with so much debt and would have been living in fear that I could not pay the bills.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Everyone has a hot button, if you will — something that motivates them whether it is money, recognition, verbal recognition, public recognition, a gift, contest, lunch, time with the CEO, anything. Learn what everyone’s hot button is and use that to your advantage to keep them motivated. Also, set small goals, celebrate small victories even if it is buying pizza for your team one day or letting them leave early on a Friday. I also find it is helpful to send a note to a team member on occasion to let them know that you are thinking about them, you think they are doing a great job and that you appreciate them. It’s also helpful as a business owner/manager to not set huge goals that are so unattainable your staff gets discouraged. Unrealistic super goals are overwhelming. And with every “super goal”, set mini-goals along the way that you can celebrate when achieved.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Don’t be a hard seller and don’t be pushy for sales. Build integrity with your audience by providing them with a product — in my case it is content — that is needed by your target audience and that they are interested in receiving. After building integrity and providing quality content, they are more likely to buy from you because you are then perceived as the industry expert.

Can you help articulate why doing that is essential today?

People are bombarded with ads everywhere in the form of texts, social media ads, etc. You need to show that you are different from everyone else. Be there to show them valuable content and be an authority in your field so they will be interested and want to buy information from you. In the end, they will place more trust in you than the person who is just trying to do a hard sell on them.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

In today’s world, it is already so difficult to stay in business. Many people move too quickly and are not fiscally responsible. For example, if you open a pizza franchise and things go really well with the first store, it is a common mistake to immediately try to expand into more locations. Expanding too quickly or over expansion is the death of many businesses. Also, not having processes in place that can be replicated and scaled is a common mistake. Once you figure out processes, you need to document them so they can be scaled. This enables you to replicate success and build on it. I do videos for training, audio recordings, or even the old-fashioned way on paper to record everything we do. I also think a big mistake is to buy things because you want them — not because they are a necessity. You should only buy out of necessity. Always think of your bottom line.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

The number one thing I can say about being a small business owner and entrepreneur is that it is a gigantic rollercoaster. As the saying goes, everything that goes up must come down….but that’s not to say it won’t go up again! You can have an amazing success one day and then two hours later feel like you took two steps back. As in Newton’s Theory, I agree that “every action has a reaction.” I am a big believer that the Universe tries to balance itself out — so for something really amazing to happen, there have to be a few not-so-amazing things happen. As a leader, it’s important to have thick skin. You can’t let things bother you. Always think about what might go wrong and be prepared. Don’t let things drag you down. Make the time to take a walk and reset.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

For Small Business Expo, it is a huge win for us when we have a major company participate and join us as a sponsor. There is nothing better than working with a reputable company and it results in a very large sponsorship sale. For me, this is an amazing high because it gives you a good feeling that you earned the trust and loyalty of a big client. It shows you those customers believe in you and your idea. This is my hot button — gaining new customers and clients. This is what makes me feel unusually high and excited. When we sign a new sponsor who is a major household name, it just feels so amazing. It is so rewarding to know they want to join the Small Business Movement and be a part of something great.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

We had a large prospective sponsor that we went back-and-forth with for months. We were in the final stages of signing the contract. Out of nowhere, their newly appointed head of marketing decided on a big brand “pivot” and put the “kibosh” on all new marketing projects. This was a huge disappointment. I had spent months of my time on calls, meetings, and presentations. Though it had nothing to do with us, it definitely was a low point for me and truly upsetting. There are always going to be highs and lows. It’s how you manage those highs and lows that define you as a leader.

Based on your experience can you tell us what you did to bounce back?

I’ve learned to roll with the punches. Know that bad thing will happen and you have to expect them. Also, learn from these bad experiences. Learn from them and see if there is anything you could have done differently the next time.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

  1. Passion: it is what drives you to keep going. Love what you do and really believe in your idea. If you don’t, then why would anyone else believe in it? People can see right through you if you don’t believe in your own ideas.
  2. Leadership: be cool, calm, and collected. Don’t be a “hot head”. Accept that things will go wrong, people will disappoint you, and learn to deal with it. Show your team that you have things under control. Your team needs to be able to look up to you. Be confident. You are the captain of the ship.
  3. Preparation: be prepared for things that will go wrong. Have backup plans, backup plans for those backup plans, etc. A successful entrepreneur will always have multiple routes to the same final destination.
  4. R&R/Rest & Relaxation: know when you need to take a break and re-energize. If you don’t, it’s a quick way to burn yourself out. You can experience R & R by doing many things, such as taking a walk, traveling, shopping, cooking, etc. I like traveling. I’ll take a weekend trip away, and by the end of the weekend, I’m really excited to get back to work.
  5. Vent/Have Advisor: have someone to talk to whether it’s your mom, your dad, best friend, or a therapist. Have someone in your life that you can trust and bounce ideas off of. Know they will offer advice or simply listen to you, whether it’s good or bad. My Mom passed away in 2009 and it has been nice to still be able to talk to my Dad to vent and get advice when possible.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Resilience is being able to bounce back from both the highs and the lows. This is the absolute definition of an entrepreneur: being resilient. Entrepreneurs are able to get through difficult situations, then bounce back — especially in front of your team or vendors. It shows confidence and leadership. Vent to your trusted advisor or a friend — not to your employees. It helps your team to remain confident when you don’t show fear, which is an everyday emotion for a small business owner.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

In 2015, I was diagnosed with cancer. I was in shock. I was scared for my life…literally. I kept thinking to myself, how the hell am I going to go through this…chemo, radiation, surgery….and stay in business and employ 18 people!? I’m not going to lie, it was one of the toughest challenges I’ve ever had to face in my life. But I got through it. I pushed through it. I knew I had 18 people relying on me, 18 livelihoods and families, not to mention a strong business that I put my heart and soul into for nearly eight years at that time. I was honest with my team about what I was going through. But I showed confidence. I put even more trust into my team. I told them “I needed them.” I needed them to come through for me and help keep the business going. Regardless of how I felt each day, I stood strong, held my chin up, and was always there to lead my team. And, I feel that we came out stronger in the end. I was very proud of my team and their accomplishments while we went through that very challenging time.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Yes, I do keep a positive attitude….but I’m also human. My emotions can certainly come out. This goes back to my comment about rest and relaxation. It’s important to recognize when you are about to lose it and go take that break. You don’t want it to wear off on your team. It is important to keep a positive attitude at all times.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

Emotions easily show — to your team, clients, vendors. I see it all the time when my sales team is excited about the product they sell over the phone, that energy passes on to the client. I always tell my team to try to leave their personal life at the door. We are all human. We all have things going on in our lives. But it’s important not to mix personal and professional. It can easily affect your work and others around you. And again, we are all human. But that is why I feel so strongly about what I said about R&R. You have to know when your body needs some time away to rejuvenate.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

I’d say one of the most inspirational quotes for me was when I read Walt Disney’s quote: “All our dreams can come true if we have the courage to pursue them.” Ain’t that the truth! That has driven me since I was a kid….to when I started my DJ business at 11 to take the leap of faith to leave my full-time salaried position in NYC and starting my own small business.

How can our readers further follow you online?

They can visit us at theSmallBusinessExpo.com or follow us on Facebook (https://www.facebook.com/SmallBusinessExpo), Twitter (https://twitter.com/SmallBizExpos), or Instagram (https://www.instagram.com/theSmallBusinessExpo/) or LinkedIn (https://www.linkedin.com/company/small-business-expo/).

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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