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Tim and Tom Investment Firm beginnings
Circa 1999

You’ve Dreamed Before, Haven’t You?

You’ve had that big idea and thought what if? That’s how it all got started for Tom Taylor and Tim Mudd nearly 25 years ago.

Tim saw a book on Tom’s coffee table and asked, “Is that a Series 65 book?”

Tom responded with a “Yes, and I’m starting an investment firm. Do you want to join me?”

And there they were, 27 years old with a VISION. So, in a car ride up to Long Island, the dream became a reality and the what if became Chesapeake Financial Advisors.

The Closet Days

We got started in a car but quickly graduated to a closet on the fourth floor of 401 Washington Avenue in Towson. We paid $25 a month in rent and needed to vacate every time our landlord wanted to access his file cabinet! But our VISION remained.

After a year, we relocated our office around the corner to 31 Allegheny Avenue where the Zagat’s rated Café Troia 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 and you know who you are. We will always remember that suite because the early foundations of our firm were built there with some sweat equity, long hours, and many ups and downs. It’s where we watched 9/11 unfold on CNBC and the tech bubble burst.

401 Washington Avenue

In 2004 we moved back to 401 Washington Avenue. For many reasons really. It’s a great building with a rich history in Towson. Charles Schwab calls the building home and we knew we wanted to provide easy access for our clients. We were on the 8th floor for a long time. We had great views of Towson and great memories meeting with you in our chopped-up suite.

It is the place where we hired Katie, our first employee, and brought on additional employees to support your growth, as well as ours. It’s where we baby sat for a client in a bind, provided office space to a client who needed a spot to work, experienced the great Maryland earthquake 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 the 12th floor and we added a satellite office in Columbia. We still had great views and made many more memories. We added additional services like tax preparation; all to better serve clients and build upon our VISION. In 2019, we opened our second satellite office in Frederick to serve the Western regions of the state.

401 Jefferson Avenue

401 seems to be good luck for us. In December 2019, we purchased 401 Jefferson Avenue. It offers private much more space for our growing team, multiple conference rooms, and the best part… PARKING! It is in the early stages of renovation to become completely modernized with the latest technology, state of the art conferencing abilities, and a comfy client lounge.

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 with us and the market. 401 is our home and it’s yours as well.

Thank You

With your loyalty and continued confidence in our services, with growing our client family, we continue to watch our VISION come to life. A VISION to build a 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


The roadtrip to Long Island and the dream.


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.


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.


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


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


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.


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


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

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