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Hidden Gems: Meet Wylie Sawyer of Watershed Entertainment

Today we’d like to introduce you to Wylie Sawyer.

Wylie, we appreciate you taking the time to share your story with us today. Where does your story begin?
Even though I always dreamed of a career in music, where I am today looks very little like what I initially imagined. When I first picked up a guitar as a teenager, I became fascinated with learning as much as I could about music, but I discovered my true addiction when I began to help put together local shows and perform for small crowds. I was always fascinated by the explosion of energy that seems to happen in the audience during live performances, and once I experienced the excitement of getting a group of people going from the stage, I couldn’t get enough.

My first career aspiration was to be a rockstar, but as my high school band parted ways and I started looking into careers in music, I slowly realized that expecting to write a hit song can feel a lot like expecting to win the lottery. I had some moderate success writing music for cable television and tried to put a few different groups together, but nothing really clicked until I started performing with my current business partners Andrew Goldstein and Lee Cumberland. With a focus on vintage rock and soul that was always meant to be played live, we quickly found success as a cover band performing in local Baltimore bars. Each night we were starting with an audience of strangers and bringing them together with the collective energy of music, and we slowly learned which songs worked best and how to craft them into a set that builds to a climax on the dancefloor.

After our first year, a fan of the band asked us to play their wedding. We had no experience as a wedding band, but we scrambled to rise to the challenge and found that our energetic sets were a natural fit for a group of wedding guests that are ready to go all out for a reception. One wedding led to another, and with a few changes to the way we were presenting our business, it wasn’t long before we were an in-demand wedding band. We continued to hone our craft, but that same collective energy I felt performing as a teenager was present as we packed each dancefloor.

Four full years of weddings later, we started getting significantly more inquiries than we could handle. Weddings tend to be on the same couple of dates each year when the weather is perfect in Maryland, and we noticed that we were getting four or five inquiries on the same dates. By this time, we knew a large network of working musicians in Baltimore, and we recruited a few of our favorite bands to join us to launch Watershed Entertainment. By combining bands that have the right energy and song list to pack a dancefloor with our wedding and event experience, we created a musician-owned agency that can provide music-loving clients with polished productions from some of the area’s top talent.

While running an entertainment agency isn’t quite like being a rockstar, the core goal of bringing energetic music to an audience remains the same. As I’ve gotten older, my desire to be the center of attention has continually dwindled, but in its place is a passion for creating a collective experience through music. Each night we start with a group of people who have never all been in the same room together before, and for a brief moment in time, we bring them all together on an energetic dancefloor.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
The element of our business that has made the greatest contribution to our success is the relationship the three owners have with each other. General wisdom dictates that you shouldn’t start a business with your friends, but it has worked for us. The mix of trust, clear communication, and complementary skills helps the business run like a well-oiled machine, but the biggest asset is simply that we enjoy spending a lot of time together.

As you know, we’re big fans of Watershed Entertainment. For our readers who might not be as familiar what can you tell them about the brand?
Watershed Entertainment is a musician-run entertainment agency that provides high-quality performances to anyone that loves live music.

As performing musicians, we understand exactly what information a musician needs to give the best possible performance at an event. It also helps us evaluate fair pay. We don’t ask musicians to go out for less money than we would require, and our bookings come with a guarantee for musicians in case of cancelation. We also set up our artists for success by making sure an event allows them to play to their strengths.

While we are a for-profit company, maintaining a reasonable work-life balance is extremely important to us. We make sure that none of our operations are dependent on one person which allows for a flexible time off schedule, and we never add stress by going into debt or leveraging our assets. We are constantly practicing saying “no” to lucrative weekend opportunities when we have important life events like birthdays or anniversaries, and all three of us have passion for taking weeks off at a time for international travel.

If we knew you growing up, how would we have described you?
Growing up, I was always fairly soft-spoken, but I was always yearning for more social experiences. You could say that I was a shy extrovert, which can very naturally lead to unfulfillment. Once I started playing music, I put almost all of my free time into it. It helped me connect with others as a shared interest, and once I started playing in public, it became what everyone knew me for.

Contact Info:

Image Credits
Victoria Selman Photography Kirsten Smith Photography Krista Jones Photography

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