Medium: Stephen Roth Of Limestone Financial Group: How My Experience in Athletics Trained Me to Become a Better Leader

Stephen Roth |

An Interview With Vanessa Ogle

Vanessa Ogle


Vanessa Ogle



Published in

Authority Magazine


13 min read

Sports teaches you to be mentally “well calibrated”. An opponent could be a competitor in business. You could link a presentation with an audience to any performance. You must prepare offensively and defensively. You could relate that in sports to a scouting report that you have a special strategy or scheme for that catches the opponent off guard. This falls under the domain of due diligence. Overall, it is a strategy to win. But keep your emotions calibrated especially, you can’t be overly confident or pessimistic.

The world of sports is not just about physical prowess or competition; it’s an incubator for leadership qualities such as discipline, teamwork, strategic planning, and resilience. Athletes, from amateur levels to professional arenas, often encounter situations that test their limits and require them to step up in ways that mirror the challenges faced by leaders in various fields. As part of this series, we had the pleasure of interviewing Stephen Roth.

Over his 17-year career in the financial services industry, Stephen has helped many clients understand how and why their emotions lead to negative, impulsive financial decisions and how a positive relationship with money can help lead you to a more fulfilling and prosperous life.

He thrives in building an in-depth understanding of those he serves through active engagement and meaningful connection from the start in order to understand what matters most to them. Through education and professional analysis, he aims to inspire meaningful change while working toward protecting and growing his client’s wealth.

Stephen started in financial services in 2003. After being a top producer and financial planner for Prudential, and 7-time MDRT qualified, he left to focus on financial planning. As the founder of Limestone Financial Group, he helps people identify and overcome their bad habits so they can live a life of purpose. As a lifelong learner, he works to stay at the forefront of wealth management by collaborating with other professionals, sharing ideas, and building a deeper understanding of how to work toward turning his clients’ visions into reality.

Beyond his work, Stephen enjoys spending time with his family, snowboarding, tennis, and golf.

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 share with us the backstory about what brought you to your specific career in athletics?

Ilearned how to catch and throw a football from my father in the back yard growing up in NJ. He was into sports and crewed at Iona College in school, His dream was eventually to be a head coach on some level. But Mom wasn’t risking being married to a gym teacher. So, he got a sales job in the flavor industry and coached me in youth basketball, baseball, and football 5& 6th grade. He started coaching my sister and girls, then asked to coach at Paramus Catholic High School in Bergen County,

Being a player and his son, it felt like he was harder on me. As a coach, you recognize talent in players & areas that need development. He showed me drills to do in our driveway to improve my game that I did. This had a positive effect on my performance in the games and fueled a continuing desire to strengthen and improve my athletic ability. This paved the way for high school athletics in NJ for me playing varsity tennis as a sophomore qualified for the all-state selection. I got good enough to play at Division III level in college, in a small minority of student athletes at colleges.

Can you share the most interesting story that happened to you since you started your career?

It’s an interesting tale which is about the 4 years in Colorado spent prior to starting my career as a financial planner. The story is about the shift in thinking that occurred about what I thought would make me happy in life. A real circular journey because I did not think I’d want my father to have a life in NJ with the same responsibilities. After graduating college, I felt like moving to Colorado was something I had to do before a career or a corporate 9–5. I wasn’t ready for those responsibilities and liked the powdery mountains not the burbs. I didn’t think I would be coming back.

Ripe at age 26 after 4 years of elevated living in the Rockies and my sanity, I was ready for something else. My parents took me back in where I had to share my old bedroom with my younger brother about to graduate college. I didn’t have too many options for employment, it was 2003 and the economy was not good.

But being a winning coach has perks that I did not appreciate as perks or think were perks as a coach’s son. He amassed wins and championships, but he was most proud of the scholarships and financial aid he helped his players get from colleges to attend. This saved parents a lot of money in tuition, and they were thankful and respected him.

Through a player’s dad, a longtime Prudential agent, I got an interview and opportunity to be hired into their financial planning program. Now I live in a house in NJ, am married raising a family and coaching my son too. (and am loving it)

Which three-character traits do you think were most instrumental to your success? Can you please share a story or example for each?

The digital world is a new place for me to engage. I am not on Facebook, never was, LinkedIn is one social platform I am on. I’m adapting to this day and age’s digital influence to grow, reach more people and engage through new channels. When I came into the business, people were cold calling, and it was all face-to-face meetings. You had to be able to talk to people and have a conversation about something interesting to create meaningful engagement with them. Having good communication skills is #1. I mentioned in a previous interview that my first job was as a caddy, which was misquoted. I was 15 years old when I began as a caddy. You had to talk to people, but it was important to listen as that is where you earned your tips, having somebody’s favorite drink waiting for them cold on the tee box goes a long way.

I keep a growth mindset. That’s something I developed through sports. I want to continue to improve in whatever I take on. That takes mindful practice, strength training, healthy habits, exercise, and a healthy diet. You need to work hard to be happy. Not everything goes your way. It’s through the negative experiences that often teach us the most, especially for growth.

Others rely on me for advice and guidance, so I seek others out that are smarter than me or have experienced what I’m going through for help and to understand what to do next. I’m not afraid to ask for help, in fact I’ve always worked to seek out mentors along the way.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Can you share a pivotal moment in your athletic career that taught you a leadership lesson you’ve applied outside of sports?

Growing up in the 80’s, tennis was not a popular sport for kids to play and my dad never played himself. Racquetball was something he played. Back then it was baseball, which I played up until sophomore year before switching to tennis. My dad still watches most, if not all Yankees games starting opening day till the end of the season. He grew up close to the stadium in the Bronx. I also played football until senior year of high school before breaking my collar bone twice, and basketball during the winter. I remember giving up baseball to pursue tennis competitively was a hard decision to make. My first job was as a caddy at an exclusive golf club in New Jersey, just outside of NYC. I was not a member’s son or “country club kid” raised with the privilege of “lessons from a pro” as member’s kids had been. I was given the opportunity to go play or hit with anyone and it was a lot of fun for me. If I wasn’t caddying, we would ride bikes and play on the hardcourts all day in Bergen County until I was exhausted. I liked the game, had good hand eye coordination, and became pretty good. But mostly, it was just good fun for me. That’s all it took to develop a passion, which fuels curiosity, ultimately driving me to focus and practice to get better and improve my skills. My parents never had to force me to do it because it was something I enjoyed. I was self-motivated. That was a “pivotal moment” in my teens. I realized I had to follow things I was passionate about and not worry about what the crowd was doing. If you do things you like, it’s easier to get better at doing them. I’m now a parent of 10-year-old daughter and 12 year old son. I coach 6th — 8th grade boys and it’s hard to motivate or get them to focus attention on anything these days with devices and distractions so prevalent.

How has your experience in team dynamics within athletics influenced your approach to leadership in the workplace?

This is a great question. One thing I’ve learned over the years interacting in groups and individually is that people want to win, which fuels all kinds of competition. People are trying to get past you on the roads driving like it’s a competition. Folks are competing for high-paying corporate jobs, which brings with it corporate competition and corporate backstabbing.

What I see a lot is aggression in people or other emotions that cause “meltdowns”. You must keep your emotions in check when you are playing on a team or competing in sports to win. Many people that never played sports don’t understand this rule because what they value in life is in disarray. They take a win-at-all-costs attitude and even resort to cheating. Look at things like the college admission scandal. People will stop at nothing to get what they want. Athletics taught me how to compete for the sport of the game. It taught me about integrity as well and how that can be applied through life.

In what ways has facing defeat or challenges in sports prepared you for handling failure and setbacks in your professional life?

A true champion has the right combination in both skill and attitude. Winning a game is easy. It feels good after, and I absolutely prefer it to losing. But real champions will win a lot of games and championships throughout their athletic or professional career. Champions don’t win every game, but they also learn to lose with grace. They are self-aware of this. It’s counterproductive to be angry at yourself or teammates. Champions learn the most about themselves from their losses. They use the experience for an opportunity to improve. Throw in the towel or keep persevering? It’s a hard career to become successful at. 90% of the people that start out as advisors do not make it. I always wanted a challenge in life, something that would be different each day and make me feel like I was building something. My career as an advisor offers all that to me as well as glimpses into the human psyche and scripts related to money inside their head.

How do you apply the discipline and training regimen from your athletic pursuits to your current leadership role?

Leading by example is key. That means staying up on industry topics and contributing to financial education through writing articles. I like to speak about problems couples face when retiring and strategies to overcome them. I’m always trying to establish myself as a thought leader. I have a process working with clients developed over the years. Once hired for an engagement a client can expect a service agreement that outlines the scope of the work, services provided, frequency of reviews, monitoring progress & performance. Having a clearly defined process and certain standards for service demonstrates my commitment to clients to manage their expectations.

Reflecting on your journey, what specific skills or attributes developed through athletics do you believe are most essential for effective leadership?

A chain is only as strong as its weakest link, which is an often-used cliché. When it comes to athletics that means each person on the team needs to do their job to the best of their ability because your team is counting on you to do your part whatever that may be. Usually, sports have offense and defense which means some players’ job is to score points and some is to play defense either way you need to effectively do both.

Based on your experience, can you please share “5 Ways That Athletics Can Help Train Great Leaders?”

  1. Athletics teaches and develops integrity and character in a person. Depending on what level one is seeking achievement or mastery… it’s for the love whatever you’re doing. You are doing something you enjoy and is interesting to you. Competing for the sport or love of the game is the intrinsic reason you do something. A sense of enjoyment or pleasure is experienced while doing the activity. It is not doing something to “be cool” or because of a request. It genuinely something you like and gain pleasure from doing. This assumes you play by the rules. Respect is complying with the rules of the game. Honoring the ethical values the game is played with shows integrity. You don’t give your golf ball a better lie when no one is looking. The only way to get better is practice and that happens when no one is looking. This applies to all professionals.
  2. Accountability is another and involves taking responsibility for your actions and performance. Teammates need to rely on you to do your job and perform at high levels. I consider myself to be very competitive. This translates to being in top mental shape, physically alert, aware of what’s going on in the economy, risks in market conditions, what’s going on in clients’ lives, and balancing their cash flow needs. They need to be able to trust me which is built on accountability and consistency.
  3. Sports teaches you to be mentally “well calibrated”. An opponent could be a competitor in business. You could link a presentation with an audience to any performance. You must prepare offensively and defensively. You could relate that in sports to a scouting report that you have a special strategy or scheme for that catches the opponent off guard. This falls under the domain of due diligence. Overall, it is a strategy to win. But keep your emotions calibrated especially, you can’t be overly confident or pessimistic.
  4. Leaders on championship teams and those leading organizations refer to their success as “collaborations”. It’s not about one person. Collaborations happen when people are comfortable being around each other. The leaders make people around them feel good about themselves and that their input is important to everyone on the team. In fact, since they are all talented professionals, they rely on each other to share feedback and communicate effectively with each other. It’s a cohesive unit and a thing of beauty to watch in action when a team is functioning at its highest levels. It’s not about one superstar or one person doing all the work or scoring all the points. The best teams have multiple ways to score and win. Think of it like portfolio diversification when investing. I take a collaborative approach in helping couples to make changes in their life. They need help, they want help, and I’ve helped other couples transition through the same thing they are going through.
  5. Athletics trains great leaders to be capable of strongly influencing others. A team captain’s role is to do exactly that. They are usually chosen by the team or voted into the role of captain, so they are usually chosen by the people. This aligns in reasoning for the captain being the individual to address the team if there is bad news to break. They are good at reading people so they can use different tactics for motivating others. You can’t always be critical or harsh on people or use bullying as an intimidating presence. To gain influence over others you must be good at engaging others to connect with them so are accepting of orders and guidance. You must give people good reasons to do things. If you are going to pay someone to help you accomplish something or achieve an objective, you want to know they have a conceptual framework for how to win. They must have a proven strategy and context for making decisions that align with your values.

    Using a financial professional that offers real planning and analysis work, makes recommendations on taxes and estate planning or benefits, and will help you prioritize things financially, can make a big difference. It’s beyond just investment advising and gathering assets. People have all kinds of issues and don’t even know what they are facing when they are about to retire. Watching retirees that are not clients get caught off guard by an IRMAA Medicare surtax without prior knowledge is terrible to witness. On or off the field these athletes are strong communicators given all the practice they have had it.

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

We need to change the conversation around aging and getting older. Don’t let it begin to depress you. There is a lot of good things to look forward to with aging. It’s already becoming a bit of a trend in media. Here are a few links,

How can our readers further follow you online?

They can get up to date financial information and tips for managing finances through my blogs on my website or you can sign up for my newsletter at

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!



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