What aspect of financial planning do you enjoy most?

I enjoy making a positive difference in others’ lives. Because of this, I became an advisor, which allows me to help people navigate tough financial decisions throughout their life. I find fulfillment in understanding what clients want from life and figuring out how to leverage their resources to bring them closer to their ideal lifestyle. I also truly enjoy getting to know people by learning about their families, their values, their goals, and their life stories. Ultimately, being a financial advisor is all about the people we serve.  

Can you tell us about your background and journey to joining Milestone? What inspired you to pursue a career in financial planning?

My path to financial planning is a bit unconventional. Initially, I aspired to be a high school history teacher, and I attended Bridgewater State University to study history. Toward the end of my junior year, I realized that this wasn’t the right path for me. I loved the idea of educating and helping others but wasn’t sold on a career in secondary education. Like many, I didn’t know what I wanted to do after college, so I figured the best way to find out was by getting into the workforce and trying out different career options. 

After graduation, I worked several different jobs until I landed at a company that organized trade shows and conferences in Boston. During long commutes into and out of the city, I began listening to personal finance podcasts to help myself with my own situation. This sparked an interest in financial independence and, more broadly, financial planning. I quickly became fascinated with finances and how the decisions you make with your resources can have a profound impact on your life. 

When trade shows were shut down due to COVID-19 and I was furloughed, I had time to reflect and decide what I wanted to do with my life. At this point, I decided to pursue a career in finance and enrolled in a master’s in finance program at the University of Massachusetts Dartmouth. As I worked on my master’s degree, I continued to search for what area of finance was the right fit for me. 

This is when I returned to my roots, listening again to the personal finance podcasts, and then I started looking into a career in financial services. Admittedly, when I researched what a financial advisor does for a living, much of the information was a bit disheartening. That’s because the first things that tend to come up center around sales jobs at large financial institutions. While I consider myself a fairly outgoing and personable person, I didn’t think this type of position was right for me. That’s when I decided to reach out to local advisors to learn more about their work. It was through these conversations and learning about how advisors are able to make a difference in their clients’ lives that I ultimately decided to start down that path myself. A month later, I found a job opening at a small advisory firm in Bedford, New Hampshire, named Milestone Financial Planning. And the rest is history. 

What do you enjoy outside work?

Outside work, I’m passionate about health and fitness. When I was in high school, I started going to the gym with my dad, and that sparked my love for weightlifting, which has stayed with me ever since. I’m very mindful of what I eat and love staying active, whether through snowboarding, hiking, playing sports, or simply a hard workout at the gym. 

Family is another cornerstone of my life; I’m incredibly close to my family. I consider my parents, siblings, and cousins to be some of my best friends. My dad was even the best man at my wedding last year. Spending quality time with them is incredibly important to me, and I cherish every moment. 

In addition to fitness and family, I’m passionate about learning. I’m always striving to expand my knowledge. This includes formal education, such as working toward my Retirement Income Certified Professional certification and pursuing a master’s in financial planning from Golden Gate University, as well as staying up to date with market trends and refining my skills as an advisor. By continually improving myself, I aim to be in a better position to help as many people as possible. 

What keeps you motivated or gives you purpose in your role?

I’m driven by competition, particularly competing with myself. I believe in my potential to achieve great things, which motivates me to reach those goals. For me, this means helping clients to the best of my ability. I’m always pushing myself to learn a little more each day—whether it’s through having discussions with other advisors, staying informed about current events, or recognizing areas where I still have room to grow. This constant learning helps me provide the most relevant and informed advice, which in turn builds my confidence in assisting clients effectively. It also enables me to help mentor some of the younger members of our planning team. This, in turn, allows Milestone to serve more families and make a greater impact on our community. 

What do you think sets Milestone apart from other financial planning firms?

What sets Milestone apart, particularly on a technical level, is our tax planning expertise. Our team of CPAs and tax professionals have decades of experience and an immense amount of in-house tax knowledge. Taxes are one of the largest expenses for most people, so minimizing that expense as much as possible is crucial. This allows clients to keep more of their money and use it to live the life they envision.  

Another strength of Milestone is our fantastic team of advisors with various specialties and communication styles. This allows us to try to match clients with an advisor who best fits their unique needs and situation.  

Are there any personal philosophies you have that you would like to share?

One of my favorite quotes comes from Yoda: “Do or do not; there is no try.” I’m a big believer in getting things done. It often requires consistent action and iteration to get those results. To me, saying “I tried” is often an excuse for giving up early and in the face of resistance. Most things have been done before, so before giving up, I find it’s important to learn from others, ask questions, and keep pushing forward. With that in mind, not everything is worth the constant struggle and effort. 

This is where the quote “The juice isn’t worth the squeeze” comes into play. While it’s important to persist in the face of adversity, not every goal is worth the time and effort required to achieve it. It’s just as important to recognize what’s truly worth pursuing and what isn’t. These two philosophies remind me that despite the importance of achieving results, they need to be pursued while also realizing what IS and what IS NOT worth the effort to actually get those results. 

What drove you to become an owner of the firm?

Becoming an owner at Milestone was an opportunity for me to have a direct impact on the direction of the firm and build upon the success of the other owners. I’m passionate about financial planning and truly believe in Milestone’s mission, so owning a part of the firm solidifies my commitment to these. It also ensures that my clients don’t have to worry about me leaving the firm to go elsewhere. Ownership gives me the responsibility and privilege to support my team and mentor interns and colleagues, helping them grow both personally and professionally. Being part of their success—and the company’s success—is something I take great pride in.  

What do you think are some common mistakes people make with their money?

One of the most common mistakes I see is having a lack of intentionality with money. People often let their money flow without a clear plan or awareness of where it’s going. While you don’t have to track every penny, having a general understanding of your spending and financial goals is crucial. Without a plan, it’s difficult to achieve the desired outcome. I believe this is often due to a lack of time or a feeling of being overwhelmed by financial matters. Many people hire us because they know it’s important to have a plan but are unsure of the best course of action. 

Another common mistake is making financial decisions based on emotions. We all have personal biases that influence our decision-making, and finances are deeply personal. I’m no exception; I’ve made emotional financial decisions in the past. That’s one of the key benefits of working with an advisor—having someone objective to talk through decisions with who knows you, your situation, and your goals can really help ensure your decisions and actions propel you in the right direction, whatever that means to you. 

What’s a trend you are seeing in personal finance and how have you adapted to it?

A trend I’m seeing in personal finance is a stronger emphasis on the personal side of financial planning. It’s not always about creating the most technically optimized plan; it’s about aligning the plan with the client’s true goals, capabilities, and bandwidth at this moment in time. It’s crucial to understand what clients really want out of life and what obstacles they may face along the way, whether financial, societal, or behavioral. By having these detailed conversations and understanding their goals and values, we can provide advice that helps them navigate challenges and achieve what they truly want. The key is to make sure the planning and actions taken are tailored to each client’s life and goals, with flexibility to adjust as those goals evolve. 

Kyle is an integral part of the Milestone Team, and we’re thankful to have him with us. Our team is committed to assisting clients in achieving their financial objectives while also building personal connections. If you need help with tax or retirement planning, please don’t hesitate to contact our team.