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Anthony Gruppo UnPeeled

Updated: Jul 11, 2020

by Shannon Peel as seen in the APeeling Digital Magazine

In January 2019, I had the opportunity to talk with Anthony Gruppo and when I did, I discovered a man who is unique and has a lot to teach the world about what it means to be a leader. In February, we started on a ten-month journey to construct a book to help others learn the lessons he learned throughout his career. As we peeled back the layers of his story, I got to know a man whom I respect and admire. But, is he the man in his stories or is there a disconnect between who he thinks he is, and the man others know?

Too often people tell one story about who they are and behave in a contradictory way because they construct a personal brand based on whom they want to be instead of who they are. In the wake of publishing his latest book, Pushers of the Possible, I decided to find out if Anthony C. Gruppo Sr’s personal brand matches the man he says he is. Let’s find out.

Humble Beginnings

He started life in a little backwater town in Pennsylvania, the son of blue-collar workers who gave him and his sister a wonderful life. His loving parents instilled a hard-work ethic into him through example and expectations, which has served him well throughout his career.

During our chats, he was quick to give others the credit or remind me, he is far from perfect with many flaws to overcome. In an interview with Paul Lucas of Insurance Business Magazine, Anthony described himself as, “a small-town person from a working-class family,” noting, “I am not impressed by myself – I am impressed by humanity.” Is this a true statement? I went to the internet to find out.

When I look at his LinkedIn activity, he is always congratulating others on their successes and praising them as talented leaders, regardless of their position within a company. His posts are not - look at how wonderful I am – posts. They are stories about his visits to the many Marsh Commercial’s branches to get to know the people he leads.

His posts celebrate other’s talents and give back to the community by engaging with it, both virtually and in the real world. He thanks people for the work they do and for spending time with him. All his posts are similar to this recent LinkedIn post, “Being with colleagues in Witham is a great way to end the week. A Talented group asking challenging informed and thoughtful questions. Well done and thank you for spending time with me.” His posts tell a story about a CEO who stands in the midst of the people he works with and applauds their successes, not his own.

When he arrived in London to take the helm, a young woman at Marsh Commercial, Jody Oxford, asked if she could shadow him for two days and write about the experience - “There is no ego, nor selfish motivation – at the core of every decision is the individual’s affected and the effect on our business. How will it affect them? What can I do to make it easier? Can I do it differently to create less impact?”

Her article describes him as a man who cares and is committed to helping the people he leads by being open to their opinions, ideas, and suggestions. It also tells the story about how he works harder than most, “He was ready to recharge and refocus, but having undertaken five town halls in less than 48 hours, and travelling over 300 miles, it was intense. Still, Anthony was able to give his all to every meeting, every call, every query without hesitation or lack of focus.”

He does not stop working, he gets up early works through his routine, goes to the office and works all day, then in the evening, he goes to events to make connections for the good of the company. He never stops. He would call me at a late hour, in NY or London, and I could hear the fatigue in his voice, however, he still moved forward to do what he needed to do to get the book done.

Considering his responsibilities, restructuring a large organization, visiting all 63 branches, writing a book, and being there for his friends and family, I do not think he sleeps.

While working on the project, I noticed he stays focused on what he needs to do at the time. He responded to messages and texts from me after his work day, when he had a moment to answer my questions. If he was with his family, he would get back to me afterwards, to focus on his family time. When we talked, he focused on the project with purpose, rarely straying from the task at hand, and only took a call if it was urgent.

Motivational Leader

Anthony tweets motivational and deep thoughts, which are insightful, and his followers engage with regularly. When I read his Tweets, I learn even in his struggles and disappointments, he finds the inspirational lessons to share with the world. However, does he actually keep a positive attitude no matter what?

I never heard him complain, even when the workload of writing the book added hours to his weekly responsibilities, which are already beyond most people’s weekly demands. He might have complained to a trusted friend, but not to me and not online. He ensured I felt secure in my role in the project, even when I made mistakes. He never pointed a finger, blamed me, or made me feel I was not good enough to continue with the project. He did what needed to be done and kept moving forward with me in tow.

When I look at his social media posts, they are always upbeat, always positive, always motivational. There is never a time of doubt, pain, or a pessimistic outlook. He does not post about negative or controversial topics. He chooses to focus only on positive and insightful messages.

I searched the internet to see what others said about his positive outlook and found many people agree, he is inspirational, motivational, and upbeat.

Nikoleta Facey posted after her experience at Bristol life luncheon where Anthony was the keynote speaker, “It was an insight into his unique leadership and stimulating thoughts on how we should challenge ourselves delivered with great energy and enthusiasm.” Tom Webster mentioned, “Anthony Gruppo talked about Marsh Commercial and his approach to leadership, really inspirational stuff.” Jody Oxford, in her article, wrote, “Motivation is one of Anthony’s greatest strengths. He has the ability to bring out the best in people and help them to believe in themselves.” Chris Lay, CEO of Marsh UK & Ireland, said in a press release picked up by many insurance publications, “With his strong track record of delivering value to clients in our fast-growing US-based MMA business, I am excited to welcome Anthony to lead our UK commercial and consumer team. His experience and dynamism will help us strengthen and enhance our offering throughout the Jelf network,” (Jelf is now Marsh Commercial). The story I found online about Anthony describes him as a motivational, inspirational, and energetic leader.


Anthony’s personal brand is 100% professional. Except for one special piece of content when his granddaughter was a co-host for an episode of his podcast, the Roots of Leadership, there is not one post about his family or personal friendships. There is very little about his personal life online, in fact, I couldn’t find anything. All of his posts are about work, leadership, and motivation.

While working on his book, I learned he has been married for over three decades, he has two adult children, and two granddaughters. Beyond this, he kept his private life, private, and remained professional at all times. The stories he shared were about his career, servant leadership, his philosophy about becoming better, and to keep pushing ourselves to do greater things.

Even his digital image is professional, I could only find one casual photo of him online. All his posted photos are work-related with him posed, dressed to the nines in a suit with shined shoes, and a smile. His comments are well thought out and all his content is business-related, be it a blog post, his podcast, a tweet, or a Linkedin post. His personal brand is well crafted and he does not stray from it.

This does not mean there isn’t personality, the man exudes personality. He has a positive energy, a light-heartedness, and a composed image. The man I got to know during the project and the one I see online are very similar.

Servant Leadership

As a CEO and leader, he has a lot of people looking to him for direction, advice, and help. It’s part of the job, however, Anthony goes beyond most CEOs. He seeks out those he can assist. As he told Paul Lucas of Insurance Business Magazine, “I don’t manage from a spreadsheet in London, looking at financials and making a decision. I sit with people doing a job. That’s when you find out about organisational procedures. I want us to be more functional – when you listen to people and you fix that, then they really want to help you too. Now there is a groundswell of people across the country offering ideas – after one town hall I had 92 ideas submitted to me.” I know he is busy, but never too busy to be there for others when they need his help because he cares about the people he leads.

His dedication to being a servant leader is not lip service, as Jody Oxford discovered when she shadowed him and wrote about it on LinkedIn, “He isn’t afraid to push boundaries and challenge methodology and importantly, gives credit to those that deserve it. He is not here to solve every problem but to empower others to seek solutions and enhance their own personal development.” This behaviour is exemplified on both LinkedIn and Twitter in his posts and those posts he engages with.

Like a true servant leader, his ego does not come before those whom he serves.

He is cognisant of how everything he does reflects on his personal brand and is careful with the choices he makes personally and professionally, to ensure he protects the image he has crafted. Unlike most, who have a purposefully crafted brand, there is no disconnect between his behaviour and the story he tells about himself. He truly wants to do better every day and works hard to improve himself and support those around him.

Being a CEO is a tougher job than I imagined. Decisions are not made lightly, carelessly, or without a heavy heart wishing there was a different way. It isn’t easy being him, even though he makes it look effortless at times. I know the difficult decisions he is required to make weigh heavy on him because he cares and has a heightened sense of responsibility to those whom he leads.

From the other side of the world, I watched him, and others, tell his story and discovered an extremely capable man. Surprisingly, in his latest book, he admits he has confidence cracks and will turn to those whom he trusts to bandage him up and help him get back into the game. It is hard for me to believe a man so accomplished, intelligent, and self-assured has confidence cracks. It is easy to assume he has all the answers to life because of his confidence, his experience, and his values.

He constantly asks others for their opinions and listens to their thoughts to gather the data he needs to make decisions. He does not speak without knowing all the facts and looks at problems from different points of view to find the best course of action. He can be an effective leader because he believes in others to help him succeed and does not believe he is a one-man show.

I am fortunate he believed in me and my ability to help him with his book, Pushers of the Possible.

As happy as I am to see the book on my shelf, with my logo on the spine, I am sad this project is over. He made a big impression on me, helped me to believe in myself, and gave my business a new direction. The APeeling magazine would not exist if it was not for him, because I came up with the idea of the magazine to promote our project and give back to him by promoting his personal brand to the marketplace. Now, I am able to provide MarketAPeel clients with a product to get their stories in front of global and hyper-local audiences.

It is his belief in me as a writer and publisher, which gave me the confidence to take a step towards my Possible.

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