FROM RESTAURATEUR TO FINANCIAL ADVISOR & ADVENTURE PROFESSIONAL
If you’ve landed on this page, you’re probably curious about what I do professionally. At my core, I’m an adventure professional—someone who chooses lifestyle and location over luxury and “stuff”. I split my time between Maine and Montana, and I’m proud to be a local financial advisor in both places. Whether I’m hiking the mountains of Bozeman or enjoying the coast of Freeport, I serve clients equally well in either state. When I’m in town, I’m always happy to meet in person, and when I’m not, video calls make it easy to stay connected.
My Path into Finance
Like many entrepreneurs, my career didn’t begin in an office. I worked as a waiter, restaurant manager, and eventually café owner. My wife and I ran a café at 100 Middle Street in Portland, Maine, serving the brokers at the Dean Witter office downstairs. With a son on the way at 29, I needed more stability, and my lifelong interest in the markets pointed me toward finance.
I joined Dean Witter—which was acquired by Morgan Stanley shortly after I was hired. In those early years, I discovered that success in the industry was often about selling, but my real strengths were in portfolio management, personal finance, analytics, business, and marketing. The first few years were challenging, but they laid the foundation for everything that came after.
Founding Harborview Investments
In 2002, I returned to entrepreneurship and convinced a couple of brokers (that’s what we were called back then) to launch Harborview Investments with me. Like many businesses, we had our ups and downs, but over 23 years we built a strong and lasting firm. We began with a mix of commissions and advisory fees, but today we’re proudly fee-only fiduciaries—meaning we don’t earn commissions and are legally bound to put clients’ interests first.
From 2002 to 2021, I served as Chief Operating Officer, and from 2014 to 2021, I was Chief Compliance Officer. These roles gave me a deep understanding of both the operational and regulatory sides of the business. Today, I’ve stepped back from daily operations to focus on what I enjoy most: helping clients plan their futures and combining finance with creativity through digital storytelling and marketing.
Serving Clients in Maine and Montana
I live and work between two of the most beautiful places in the country—the coast of Maine and the mountains of Montana. Being a local financial advisor in both regions allows me to meet clients where they are, whether that’s in Portland, Freeport, Bozeman, or Big Sky. Many of my clients prefer face-to-face conversations when I’m in state, while others work with me entirely through video calls. Either way, they get the same level of clarity, service, and commitment.
Today
I work from my home offices in Freeport, Maine and Bozeman, Montana—but I stay connected no matter where I am. Whether I’m flying or off the grid, I’ve built a system that keeps me accessible to clients from virtually anywhere.
I love helping people turn dreams into real lifestyle goals. I believe personal finance and creativity go hand in hand—because when money is a source of stress, it’s hard to think clearly or build anything meaningful.
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🎯 It’s not about working with me—it’s about learning how to work for yourself.
Until next time…
Daryl