A career spanning more than 30 years in financial services has positioned Robert Carpenter as a driving force behind Baltimore-Washington Financial Advisors’ growth into one of the most recognized registered investment advisory firms in the Baltimore–Washington region. As president and CEO, he oversees investment management, financial planning, tax advisory services and mergers and acquisitions, while also serving as a lead adviser and portfolio manager.

Carpenter earned a bachelor’s degree in political science from Hartwick College and holds a Wharton/SIA Management Leadership Institute Certificate from the University of Pennsylvania. He has been recognized on The Daily Record’s Banking and Financial Services Power List.

What is the biggest challenge facing your industry today?

One of the biggest challenges facing our industry today is the tendency to try to solve every problem with technology. There’s no question that advancements in artificial intelligence, data analytics and digital platforms have enhanced efficiency and access to information, but they can’t replace the human element that sits at the core of truly effective financial advice.

In my experience, the most meaningful guidance doesn’t come from an algorithm; it comes from understanding people. Every client brings a unique set of values, fears, goals and life experiences to the table. The real work is uncovering those personal dynamics and translating complex financial strategies into something that resonates on a human level.

Technology can process data, but it can’t fully grasp nuance, emotion or the deeper motivations behind someone’s decisions. Nor can it communicate with empathy or adjust its message in real time based on how a client is feeling or reacting. That’s where great advisers distinguish themselves, not just by what they know but by how they connect.

The challenge then is striking the right balance. We should absolutely leverage technology to enhance our capabilities, streamline processes and provide better insights. But we can’t let it become a substitute for thoughtful conversation, active listening and personalized guidance.

At the end of the day, the advice that truly changes lives isn’t just technically sound; it’s delivered in a way that inspires action. It’s about helping clients see what’s possible, building their confidence and guiding them toward decisions that align with their goals and values. That kind of impact doesn’t come from technology alone; it comes from human understanding and meaningful communication.

What is the best advice you’ve ever received?

The best advice I’ve ever received is simple, but it has shaped everything I’ve done: Do what you love, and you’ll never work a day in your life.

To me, that doesn’t mean work isn’t challenging or demanding; it absolutely is. But when you’re genuinely passionate about what you do, the effort feels purposeful. The long hours, the problem-solving and even the setbacks become part of something you care deeply about rather than something you’re trying to get through.

I’ve been fortunate to build a career around helping people make important financial decisions, and that sense of purpose has always driven me. When you enjoy the work itself and believe in the value you’re providing, it changes your mindset. You’re not just working; you’re contributing, growing and making a meaningful impact.

Over time, I’ve also realized that doing what you love isn’t just about personal fulfillment; it translates into better outcomes for the people you serve. Passion shows up in the way you listen, the care you bring to each relationship and the commitment you have to doing things the right way.

That advice has stayed with me because it’s not just about career satisfaction — it’s about building a life where your work aligns with who you are and what matters most.

How do you define success?

I don’t define success by recognition or accolades; it comes down to the impact I’ve had on others. I look at the thank you notes I’ve received from clients, the trust placed in me by the community I serve and the students I’ve had the privilege of teaching over the years. Each note represents a relationship built, a life positively influenced or a lesson that truly resonated. To me, success is measured by those meaningful connections and the lasting difference I’ve made in people’s lives.

With nearly three decades in financial services, Andrea Kirk, CFP®, CRPC™, APMA®, has built Inspire Confidence Group into a comprehensive wealth management practice within Ameriprise Financial Services LLC, where she serves as private wealth adviser and managing partner. A Certified Financial Planner, Chartered Retirement Planning Counselor and Accredited Portfolio Management Advisor, Kirk earned a bachelor’s degree in finance and management from Notre Dame of Maryland University in 1998.

Her practice focuses on retirement, estate planning and women’s financial strategies. Kirk serves on the investment committees of the Community Foundation of Harford County and ARC Northern Chesapeake Region, and chairs the governance committee of the Sexual Assault Resource Center — Maryland.

What is the biggest challenge facing your industry today?

Advisers aging out of the business. Many advisers are retirement ready but have not intentionally planned for the transition of their clients, culture or enterprise value to the next generation.

Using CEPA principles, we see this as a value acceleration issue. A practice is strongest when it’s transferable. When relationships, processes and purpose extend beyond the founder. Without early and thoughtful continuity planning, advisers risk eroding client trust, team engagement and the long-term value of the business they’ve worked a lifetime to build.

The opportunity is to treat succession not as an exit event but as a strategic process. One that aligns people, purpose and planning well before retirement is on the horizon.

What is the best advice you’ve ever received?

This was hard to pick just one. But first, “Do the hardest tasks first.” This applies to life, parenting, work. Give your best energy to the hardest tasks first and you will feel more effective.

And just as important, another golden nugget is “learning that rest is not the same as quitting.” I used to believe staying busy meant being productive, especially juggling work, family and responsibilities. Being reminded that rest is part of doing well, not the opposite, changed how I take care of myself.

How do you define success?

Success changes as life changes. At this point in my career and personal life, I define success by the well-being of the people around me: my family feeling happy and secure, my team being engaged and not overwhelmed, and me maintaining strong physical and mental health. When those pieces are in place, performance and fulfillment follow naturally. I no longer seek 10/10 in one focused area but rather 7/10 in all things, my health, my family, my team. This balanced approach means we are winning.