Anthony Stewart once aspired to a career in sales and marketing, believing it would offer better financial opportunities. However, he never had the chance to break into this field. Instead, he reluctantly ventured into financial services – a path that has led him to remarkable success and his true calling. Today, as President of American Classic Agency (ACA), Anthony leads an organization dedicated to helping independent life insurance professionals thrive while ensuring financial security for Middle America.
Anthony doesn’t just lead – he inspires. He wishes to be an example that inspires others. For him, true success is also about inspiring others and helping them do things they never thought possible. “Success, to me, also means having the freedom to do what you want, when you want, and how you want — without needing permission from anyone,” he says.
Anthony wants to leave the world a better place through his efforts, vision, mission, and purpose. “As President at ACA, my vision is to change the financial trajectory of Middle America while bridging the wealth gap in America,” he says.
The Humble Beginnings
Anthony grew up with nine siblings on Maryland’s Eastern Shore. He and his siblings saw education as their way out of country life. Anthony proudly shares that all ten of them earned college degrees, with most going on to obtain advanced degrees.
“However, with ten children in the family, someone was always in college,” Anthony recalls. “Money was never just lying around.” He saw his parents work incredibly hard, and he himself started working hard at a young age. According to him, he was the hardest-working sibling in the family. “I used to cut the neighbor’s grass and do other things,” he recalls. “This made me develop an entrepreneurial spirit early on.”
Anthony is calm, gets along with everyone, has immense patience, and believes in serving and sharing. He credits these qualities to his growing-up years with his siblings in a three-bedroom house. “You’re going to learn to share, get along with everybody, and be calm and patient when you’ve ten siblings,” Anthony says.
Transitioning from Xerox to Financial Services
When Anthony was working at Xerox Corporation, he wanted to pursue something that didn’t put a ceiling on his income. “At the time, sales and marketing seemed like a perfect fit,” he says. Multiple times, Anthony tried to switch to sales and marketing at Xerox but didn’t succeed. Then, a friend of his suggested that he explore opportunities in financial services.
Anthony recalls that at Xerox, although his working hours were long, he was not earning much money. Also, there was not much freedom. But, when his friend told him to take a look at financial services, he remembers saying, “I don’t know anything about financial services. And I’m broke.”
“That’s why you need to get in,” Anthony’s friend replied. He also pointed out that if Anthony, being college-educated, didn’t understand finances, there were probably many others who didn’t either – and Anthony could help them. This is how he started working part-time in financial services – with no intention of ever going into it full-time. But after about three years, his part-time income began to match his full-time income at Xerox.
Despite earning well from his part-time job, Anthony was afraid to leave his secure nine-to-five job. He then thought: if he were giving Xerox 40 hours a week, what would happen if he gave himself 40 hours a week? In July of 1993, he finally took the leap and completely moved to financial services – and he has been in this field ever since. “And I love it,” he says.
Anthony also says, “I think this is my calling — to be doing exactly what I was meant to do.” He now believes that this is why things did not work out for him at Xerox in terms of getting into sales. “I think God had planned a bigger calling for my life,” he says. “He didn’t want me selling copiers; He wanted me to influence and inspire others to do what I do. And that’s what led me here today.”
Journey with American Classic Agency
ACA is the solution for aspiring and experienced independent life insurance professionals who desire to serve Middle America. It is a company that cares, an open-door company where everyone supports one another. “One Team, One Dream,” Anthony says. “We teach each agent to mentor another agent.”
He was introduced to ACA after he outgrew the other organization. He started out as a regular agent and then began recruiting and building his own Stewart Financial Services within the organization.
Anthony never had aspirations of becoming President or Co-Owner of ACB. “It was something I never even sought out to do,” he says. His loyalty and high-level performance drew the attention of the former President, who believed in Anthony’s potential to lead the organization. Anthony says, “When we first took over his ownership in July 2018, I was just the Chief Marketing Officer and Co-Owner.”
When the key leaders retired, the remaining two partners chose Anthony as President of ACA, recognizing his clear vision and focus. Anthony began his fourth term as President on January 10, 2025. Since he stepped into this role, ACA has been growing about 25 percent a year. Its female sales force has been growing as well; according to Anthony, it is because of the shift to virtual operations following the COVID-19 pandemic.
Also, ACA now recruits all across the country. “People no longer have to drive around like I did when I first started,” Anthony points out. “They can conduct business from the comfort of their homes.” He believes that this has significantly contributed to the growth of the organization, especially with more women joining them.
As a leader, one of the most memorable stories Anthony witnessed happened a few years ago. One of their top agents asked him to go to Pennsylvania to deliver a one-million-dollar check to a family. “The husband had passed away at age 44,” Anthony shares. “He only had the policy for five months, but the insurance company paid the claim. There was not a dry eye in the house.”
Writing a Book
A former business partner asked Anthony to consider writing a book about ACA’s work and the services they provided. Initially, he was hesitant, thinking it would be too time-consuming. However, once he started, he became passionate about the book, “Saving Middle America: Securing Financial Dreams,” which he has co-authored. This book’s language is simple – it does not have difficult-to-understand fancy words. While writing the book, Athony’s goal was to ensure that everyone understood the message.
The book’s target market is Middle America “We’re not going after the 1% of wealthy people, although we do have some of them as our clients,” Anthony says. “Our focus is Middle America because it’s the most underserved population.”
Dealing with Challenges
Initially, finding clients was a major challenge for Anthony. After quitting Xerox, he no longer had a regular salary and was working only on commission. The thought that “there’s only one of me” made him worry about what would happen if he fell sick. “The inconsistency of pay was a challenge until I built a solid client base,” he says. “Then, things leveled out and gave me some form of security.”
Now, the challenges he encounters are not about finding clients for himself but about helping some of the agents acquire clients. Anthony explains that this is why they are currently exploring different lead sources. “It is a big challenge to help agents get clients and get them up and running quickly,” he points out.
Anthony knows that fast pay makes fast friends, but it is a challenge to ensure that agents get paid quickly. “If that happens, they are more likely to stay,” he says. And, at ACA, agents do stay for a long time. Anthony shares that some of their key leaders’ average tenure is over 17 years, which is unheard of in the independent space. According to him, normally, such longevity is only seen on the career side, with companies like New York Life or State Farm.
A President’s Work Schedule
Anthony begins his day with exercise, followed by breakfast, and then arrives at the office around 9:30 a.m. The night before, he prepares his to-do list and notes the people he needs to contact. As President, he checks on his leaders to see if they are doing well; he takes care of his personal clients as well. At the office, he discusses with his office manager what they need to do. After that, he proceeds with his day.
Anthony’s role requires him to be involved in seeking recruitment opportunities. He also says that his team makes calls to set up seminars where he presents to churches and different civic organizations. In addition to that, he and his team also conduct extensive training programs, which play a critical role in their success.
Anthony normally wraps up his work at around 5:30 or 6 p.m. He then stays at the office for another hour or so preparing for the next day. “I think preparation is the key to effective leadership,” he says.
When he is not leading ACA, Anthony loves to spend quality time with his family. He also enjoys watching sports. He is involved with various ministries at his church, the Omega Psi Phi Fraternity, Incorporated, and the local alumni group at his alma mater, Bowie State University.
The leadership philosophy that Anthony follows is: “Treat everyone on your team with respect and honor, from the top producers down. Treat people how you want to be treated.” At ACA, he often stresses, “It’s not about me, it’s about us.”
Drawing Motivation From
Anthony draws his motivation from a number of things. First, it is from their vow to make a difference in their communities. “We’ve all vowed to improve the financial lives of the people in our communities and truly change their financial trajectory,” Anthony says. “That’s what motivates me every day.” He is also motivated by the thought of never becoming broke again.
“Being an example for my family, children, and grandchildren is important to me,” Anthony shares. “I want to show them that if you work hard, stay focused, and remain committed, you can accomplish great things.” This motivates him as well.
Anthony loves seeing their agents achieve their goals, and he pushes them to keep moving forward. “This is what drives me every single day,” he says.
Plans for the Future
Anthony wants to continue growing personally by working on himself, becoming a better person, and getting better at leadership. That’s the main thing I want to focus on personally — continuing to become better while also growing the organization.
As President of ACA, he has promised three things. First, he wants to protect the brand. This is why he makes sure to choose the right people. He explains that everyone can’t work with them, as they demand a certain level of commitment from their people. According to him, individuals with certain characteristics do not align with the organization’s values. “We only want to work with people who are going to do the right thing – that is it,” Anthony says.
He not only wants to protect their brand but also elevate their profile in the community. He wants to see ACA becoming a household name. “When people want to get into financial services,” Anthony says, “I want others to tell them, ‘You’ve got to call this company called American Classic Agency’.”
The third promise he made was “to grow the organization.” He says the only way to achieve this is by continuing to serve and bringing on new agents to work with them.
Anthony believes he still has more to achieve in his business. “I want us to become a $50 million organization,” he says. “That’s my three-to-five-year plan.” He believes they can get there with the systems they are putting in place today.
Message to Aspiring Leaders
“Find a mentor and learn from them,” is Anthony’s first piece of advice to aspiring leaders in the financial sales industry. He also advises them to be honest with their mentors and open to receiving honest feedback about what they need to be doing on a daily basis to succeed as entrepreneurs in the financial service industry.
He also tells aspiring leaders not to enter the industry only for the money. “Strat thinking long-term,” he points out. Anthony encourages them to find their niche early on, adding they should not try to be everything to everybody. “What I mean by that is, we have some excellent products at American Classic, but there are certain things we would rather not do,” he explains.
“And collaborate with people who are operating at a higher level than you are,” Anthony adds.
The Legacy!
Anthony wants to be remembered as a leader who really cared about his people — someone who not only talked the talk but also walked the walk. “I want my legacy to be one of the highest levels of integrity, involvement in the community, and servant leadership,” he says. “That is who I am.”
