Cheri’ Benjamin of The Benjamin Group On Becoming Free From The Fear Of Failure

An Interview With Savio P. Clemente

Savio P. Clemente
Authority Magazine


Find other avid learners who take action. Surround yourself with people who are always seeking knowledge and implementing what they learn. A lot of people get stuck because they don’t take action. Expand your circle with people who do what they set out to do.

The Fear of Failure is one of the most common restraints that holds people back from pursuing great ideas. Imagine if we could become totally free from the fear of failure. Imagine what we could then manifest and create. In this interview series, we are talking to leaders who can share stories and insights from their experience about “Becoming Free From the Fear of Failure.” As a part of this series, I had the distinct pleasure of interviewing Cheri’ Benjamin is the CEO of The Benjamin Group, Village Premier Collection (VPC), and Weinsure Jag companies.

Cheri’ Benjamin is the CEO of The Benjamin Group, Village Premier Collection (VPC), and Weinsure Jag companies. She began her journey in Real Estate as a Loan Officer in 2000 and became a real estate agent in 2006. Since then, Cheri’ has worked diligently to have VPC recognized as one of the top 5 commercial real estate brokerages in Metro Atlanta and ranked #676 on INC 5000. VPC is also the largest minority veteran and female-owned real estate brokerage in Georgia with over 470+ agents and 22 loan officers.

Cheri’ has been featured in several national and local publications, podcasts, radio, in-person speaking engagements and online interviews. As a national real estate coach, she remains passionate about helping others flourish and is currently mentoring five brokers from around the U.S. Her vibrant personality and drive to get things done well makes for a pleasant, and always professional, real estate experience.

Cheri’ is also a proud US AIR FORCE Veteran, values being active in her local community and is a family-oriented individual. She and her husband have 5 sons.

Thank you so much for joining us! Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’?

From a very young age, I was encouraged to work hard and speak my truth. I graduated high school when I was 16 with a 4.0 GPA. While I was offered scholarships to every college I applied to, I decided to join the U.S. Air Force where I knew my limits would be challenged in ways academia couldn’t. I quickly rose through the ranks and received top clearance, but because I was outspoken my growth was restricted and I left my military career behind. My husband at that time and I moved to Colorado for a fresh start. I tried to be a stay-at-home mom, however, I craved more challenges and couldn’t do the stay-at-home mom thing anymore. I accepted a job as a loan officer, and in three months I broke the record for the most amount of transactions in one month, which still stands today. Just as baby number three was making his way into the world, I moved back to Atlanta to be near family. A few years later, I got a divorce and that’s when my real estate career took off. I started on a team and it expanded to 48 agents. I became a National Real Estate Coach in 2016 helping teams scale from $200,000 to over 2 million in profit. In 2019, I purchased a real estate firm in Atlanta, which is where I held my license. This was a bold move because I was actually living in Las Vegas. In three years, we’ve expanded into 10 different states and several markets. Village Premier Collection is currently the largest minority, veteran female-owned real estate brokerage in Georgia with over 400+ agents and 22 loan officers.

Can you share with us the most interesting story from your career? Can you tell us what lessons or ‘takeaways’ you learned from that?

The offer to purchase Village Realty, which I renamed Village Premier Collection, arrived in an email. It was a complete shock because I hadn’t seen myself in that role, especially living so far away from the corporate office. I thought it odd to receive such an important opportunity in an informal manner. The owner wanted me to partner with someone else whose work ethic differed from mine. I had to create a strategic argument that would inspire the other party to back out of the deal. I explained to him that owning a business would take more than leadership skills. It would also require drive, stamina and a new structure that was not currently in place. He decided against purchasing the company and I learned two important lessons. The first is to go with your instincts. When you can clearly identify the direction you want to take, remove any obstacles and make it happen. The other party was a great team leader, however, I felt he didn’t have the desire to take ownership of his actions nor did he possess the vision needed to grow the company. From my coaching experience, I knew what the foundation had to look like and I didn’t compromise.

The second is to build a team that is as driven and willing to learn from their mistakes as you are. I expect those I hire to mess up because we all do. I ask them to let me know when it happens because even if they’re in the wrong, and even if they haven’t learned the lesson yet, we can find a solution. This includes working on their emotional intelligence to handle high-stress situations without freaking out in front of clients. If they can do their role 80% as well as I can, I let them do it and can train them to master the other 20%.

You are a successful 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. Dominance — I command attention and speak with authority when I’m talking business. I trust myself and there’s no need to compromise that.
  2. Analytical — I can see holes in business strategies and scale a property until I have the tools to overcome any roadblocks slowing our growth. When I purchased Village, I looked at the budget and immediately changed the overhead which was way beyond their growth trajectory. The cost to staff the original 118 agents I acquired is equivalent to our current staff supporting over 470.
  3. Chameleon and Listener — I was encouraged to explore many different cultures growing up and can adapt to almost any situation. I’ve learned to mirror the way a person speaks to me by matching their body language and vocal cadence. It creates a level of trust and a feeling of comfort and ease. That causes people to open up about their wants and needs. This approach helps when I’m coaching an agent because as soon as I see that glimmer of light, I pour kerosene on it and help them turn their dial all the way up on their hopes and dreams. It benefits clients because I can decipher what they truly desire and develop a strategy to make it happen. That’s my purpose in life, to help amplify what people want and gain faith in their own abilities.

Ok, thank you for all that. Now let’s shift to the main focus of this interview. We would like to explore and flesh out the concept of becoming free from failure. Let’s zoom in a bit. From your experience, why exactly are people so afraid of failure? Why is failure so frightening to us?

It’s frightening because failure means we’ve quit. The reality is, if you are persevering, then you’re not failing, you’re learning a lesson. You’re shifting from identifying with failure to understanding something new or different. Think of it like giving birth. When you’re pregnant, you’re growing something inside that you deeply love even though you don’t know what the future holds for that life. The experience is painful, you grow in ways you don’t like and sometimes you’re physically sick. It’s frightening because you don’t know exactly when the baby will come, even if it’s scheduled. You don’t know what it will be like, but it doesn’t mean you’re failing. It means you’re carrying something new. When you finally give birth, you meet a new version of yourself, another part of you.

My first husband was an abusive person. I stayed with him because I didn’t want to fail my family and have my kids come from a broken home. I thought of divorce as a failure. But, when I finally left, I kept learning. I learned how to take care of myself first, build myself and my family up and how to live as an unmarried person again. It may take time and there’s no imaginary thought-bubble that will pop up and show you the lesson. Every experience, even if you fall, is an opportunity to learn to get up and run with it. Dr. Martin Luther King, Jr. said, “If you can’t fly, then run. If you can’t run, then walk. If you can’t walk, then crawl, but by all means, keep moving.”

What are the downsides of being afraid of failure? How can it limit people?

The downside is that you’re stuck. The fear of failure comes when you’re overwhelmed and you end up freezing, just sitting there. To move past it you have to create some distance from the problem and figure out the first step to solve it. Eliminate everything else, zone in, put blinders on and execute it. That’s it. All you need is the first step because once you execute it, the rest of the staircase opens up.

Forward progress is how we stay in alignment with our purpose. If you don’t understand what your purpose is, that’s okay because it comes to you as long as you’re moving forward. Release the pressure to know the outcome. Have grace with yourself and understand that you are learning. Say it as many times as you need to: I’m not failing, I’m learning. Then ask yourself: What am I learning? Be sure to look back and evaluate your process and progress.

Athletes always look at game film. Why? To gain a closer look at every error and see where improvements are needed. If a lineman steps back on the wrong foot, he might not protect the quarterback the right way. Athletes evaluate and practice their actions so they can learn. It’s why we sing the ABCs to our kids until they can identify each letter. At first they sing LMNOP as one letter, but as we guide them, they learn to differentiate the sounds of each letter until they reach the next level in learning. We can move from grammar school to high school to college, but none of us have PHDs in business because it’s always evolving and changing and we’re constantly learning new things. If I gave up because I noticed I was saying LMNOP instead of learning the correct way to say it, I would have been stunting my growth. Not even Elon Musk has figured it all out. He’s always seeking more information to improve his skill set. If he stops, then he fails. Keep the momentum going, that’s how you grow and succeed.

In contrast, can you help articulate a few ways how becoming free from the free of failure can help improve our lives?

There is no freedom from failure, there is only freedom from identifying with it. Once you embrace that reality, it changes the way you think all the way around. It improves your parenting skills because you’re able to relate to your children when they’re frustrated or feeling defeated and can encourage their growth. It makes you a better spouse or partner because you can offer support when they feel like giving up. In business, you can redirect those you lead to show them what they’re learning rather than failing. You become a rock for others. When they think they’ve lost, you’re able to show them the opportunity and the lesson. It’s so powerful to see them become reenergized and go back out into the world.

We would love to hear your story about your experience dealing with failure. Would you be able to share a story about that with us?

As I said, my definition of failure is quitting. The only thing I can truly say I’ve ever quit was my first marriage and, even then, I learned so much about myself. My ex was a womanizer. He was mentally and physically abusive. Most people don’t understand how I could’ve remained in that relationship for 17 years, but the manipulation was slow. He would double down on my insecurities, reinforcing them by telling me parts of me needed to go away. I was depressed and angry all the time. I didn’t recognize myself anymore. I couldn’t find Cheri’. I was afraid to leave because I didn’t want my children to grow up in a broken home and to leave would mean I’d have to put myself and my needs first before my children’s. That’s very hard for a mother to do. I finally left. At some point, I realized that putting my needs first was putting my family first. I quit him, not my family and not myself.

How did you rebound and recover after that? What did you learn from this whole episode? What advice would you give to others based on that story?

I started going to Barnes & Noble and spent the little money I had on self-help books because I knew I needed to rebuild my mind. I understood that I wasn’t controlling the negative self-talk going on between my ears. I needed to feed myself with positivity to push it out. Dr. Martin Luther King, Jr. said, “Darkness cannot drive out darkness; only light can do that.” I had to focus on the light. I got rid of my TV and cable. I stopped watching the news. There were no apps at the time to distract me. I had to silence the noise, learn to listen to that person inside of me that had been pushed down and gave her space to grow.

I needed to carefully choose who I’d allow in my life. I realized my kids and I needed a larger circle of people around us; my circle was a dot. I had three children and a good friend of mine who would later become my husband. I decided that I wouldn’t ask my parents for advice because I needed to learn this for myself. I had no other family to call. I cut out girlfriends because I didn’t want any outside influences. I didn’t want to hear what my divorced friends had to say because they had failed marriages too and couldn’t tell me what a good relationship should look like. As much as I wished I could, I couldn’t talk to Gandhi, MLK and Mother Theresa, but even they weren’t perfect people. I realized there were no perfect humans and I needed to start giving myself grace and stop asking others for their advice. That’s when I understood I truly was learning. My first marriage was not a failure, it taught me a lot of lessons. I have three beautiful children. I understand and can relate to people who have a fragile state of mind. Once I shifted my own mind, I found more driven people like me. Even though I started out believing divorce was my biggest failure in life, was it really? I look at where I am now and I know that I didn’t quit on myself, so I didn’t fail.

Fantastic. Here is the main question of our interview. In your opinion, what are 5 steps that everyone can take to become free from the fear of failure”? Please share a story or an example for each.

  1. Identify your first step. It will help you create a plan.
  2. Once you have the first step, block out distractions, get in your zone and stick to it.
  3. Tell someone you trust about your plan and give them permission to hold you accountable.
  4. Find other avid learners who take action. Surround yourself with people who are always seeking knowledge and implementing what they learn. A lot of people get stuck because they don’t take action. Expand your circle with people who do what they set out to do.
  5. Shut out the noise. You have to listen to what’s between your ears, bring in the light and honor who you are.

The famous Greek philosopher Aristotle once said, “It is possible to fail in many ways…while to succeed is possible only in one way.” Based on your experience, have you found this quote to be true? What do you think Aristotle really meant?

I think it’s the other way around. There are so many ways to succeed and only one way to fail.

Failure is quitting, and there’s only one way to do that — you stop. In my opinion, that means you’re dead because you can always keep on trying as long as you’re alive. If you’re learning lessons, where is the failure?

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. :-)

Be authentically who you are and who God made you to be. Turn up the light within you, grow it and walk in that freedom. That’s what we do at Village Premier. That’s what I’ve built my company to be — a place where people are welcome no matter who they are, who they love or how they identify. It’s about growing ourselves while deepening our professional skill set. We need to be the change we want to see.

We are blessed that some very prominent leaders read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them :-)

Oprah Winfrey. She is devoted to being her most authentic self and hasn’t shifted away from her purpose. From the time we have seen her on television, she has not walked away from who she is. Even when she made declarations that she didn’t want kids or to get married and the public challenged her on that, she chose her own direction and stuck with it.

My best friend, on the other hand, would be Serena Williams. Her drive is insane. She is so sweet, fierce and strong like a bodybuilder. She could be everyone’s friend and will do anything for those she loves, but you don’t want to mess with her. I identify with people who are strong and driven, people that won’t shatter. People who don’t bend even if others try to break them down.

How can our readers further follow your work online?

FACEBOOK @VillagePremierCollection

INSTAGRAM @VillagePremierCollection

LINKEDIN @VillagePremierCollection

This was very inspiring. Thank you so much for the time you spent on this. We wish you only continued success.

Thank you! It was my pleasure working with you.



Savio P. Clemente
Authority Magazine

TEDx Speaker, Media Journalist, Board Certified Wellness Coach, Best-Selling Author & Cancer Survivor