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Tim and Tom Investment Firm beginnings
Circa 1999

You’ve Dreamed Before, Haven’t You?

You’ve dreamed before, haven’t you? You’ve had that idea and thought what if? That’s how it all got started for us nearly 30 years ago. Tom was asked about a Series 65 book on his table and responded, “It’s mine and I’m starting an investment firm”. He was 27 years old with a VISION and in a car ride up to Long Island, the dream became the reality that is now Chesapeake Financial Advisors.

The Closet Days

While we started in a car, we quickly graduated to a closet on the fourth floor of 401 Washington Avenue in Towson. We paid $25 a month in rent and had to leave whenever our landlord wanted to access his filing cabinet, but our VISION remained!

We relocated to 31 Allegheny Avenue where the Zagat’s rated Café Troia once called home and now Banditos calls home. The next time you dine there—and we recommend it highly—walk to the back of the dining room and look into the far right corner. That was where we met many of our first clients.

The early foundations of our firm were built in that suite with sweat equity, long hours, and many ups and downs. It’s where we watched 9/11 unfold and saw the tech bubble burst.

401 Washington Avenue

In 2004, we moved back to 401 Washington Avenue. It’s a great building with a rich history in Towson and amazing views. Charles Schwab once called the building home as well and why we chose the location to provide easy access for our clients.

We made great memories in our chopped-up suite, including hiring Katie, our first employee, and bringing on additional team members to support your growth and ours. It’s where we babysat for a client in a bind, provided office space to a client who needed a spot to work, experienced the great Maryland earthquake of 2011, and continued to build upon the foundation of our VISION.

Growing the VISION

We are guided by what is best for our clients, so in 2014 we moved to an updated suite on the 12th floor and added satellite offices in Columbia and eventually Frederick, Maryland. We also added additional services like tax preparation & planning — all to better serve clients and build upon our VISION.

401 Jefferson Avenue

With continued growth and an eye on our VISION, we knew we needed a forever home. So, on the eve of the COVID quarantine, we moved into our forever home at 401 Jefferson Ave. Equipped with onsite parking and level access, state of the art technology to communicate with clients all over the world, we knew our clients would come to value it as their home as well. If you are in the area please drop by and see us. We’ll show you around, grab a cup of coffee or a cold drink, and catch up.

Thank You

For without your loyalty and continued confidence in our services, without growing our client family, we cannot move forward on our VISION of building the best fiduciary-based, fee-only financial planning, investment advisory, and tax preparation firm that always puts you and your best interests first; where we are on the same team as our clients as they achieve their goals and realize their dreams; just as we are so blessed to have realized ours.

From a Car Ride to Now – The CFA/TC Family Timeline

1998

The roadtrip to Long Island and the dream.

2000

We quickly moved to a closet at 401 Washington Ave. in Towson. Rent was $25 a month, and we needed to vacate every time our landlord wanted to access his filing cabinet.

2001

Expanded to around the corner where Zagat’s rated Cafe Troia calls home. It’s where we watched 9/11 unfold and the tech bubble burst.

2004

Moved back to 401 Washington Ave. for more space and to be closer to Charles Schwab whom calls the building home.

2010

Still at 401 Washington Ave. We hired, Katie, our first employee, plus other team members. We also experienced the great Maryland earthquake here.

2014

We expanded our office space at 401 Washington Avenue. We opened an additional office at Columbia and added tax preparation services…all to better serve clients and build on our VISION.

2019

We opened a satellite office in Frederick and expanded our team to add a more personalized client experience.

2020

We have our own building! Perfectly social distant at 401 Jefferson Avenue in Towson.

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