We caught up with the brilliant and insightful Will Cunha a few weeks ago and have shared our conversation below.

Hi Will, thanks for joining us today. Let’s kick things off with your mission – what is it and what’s the story behind why it’s your mission?

When we first started Oscar’s Coffee we knew it had to be both unique and part of the neighborhood. We spent weeks developing criteria about our location, how it would integrate with the community and not increase friction, and how it would best serve our neighbors and the business. We defined our values as: We’ll be a good neighbor, We’ll always nail the basics, and you’ll always matter. For us, these values embody our mission – to change our neighbor’s morning routine. Centered around the walkability and neighborly vibe of Eastport, Oscar’s was created to give our neighbors a place to meet each other, have a friendly destination for their morning walk, and generate new friendships based on a few shared common joys – dogs and good coffee.

Will, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

Spoiler alert – Before Oscar’s, I really didn’t drink coffee. I graduated from the Naval Academy in 2011 and served on two ships based out of San Diego, CA and Yokosuka, Japan. Although I spent hours on watch, I never really was a coffee drinker. After leaving the military and graduating from grad school I moved to DC where I met my (now) husband, Garrett. On NYE of 2022, we were hanging out with my parents in 30A Florida when we started talking about coffee in Eastport (or the lack thereof). My Mom used to travel around the country in their family’s Shasta trailer when growing up so we thought, “That’d be cool!” Long story short, here we are!

Oscar’s Brand is unique, but familiar. It’s about being comfortable but also a bit refined. Our goal is to change our neighbor’s morning routine by getting their day started with a good cup of coffee surrounded by their neighbors and their neighbors’ dogs. What could be a better start to the morning?

Can you share a story from your journey that illustrates your resilience?

The journey to just get Oscar’s open was long and laborious. From the challenges we faced getting the trailer refurbished (it was almost destroyed on its way down to be restored) to working with the City on obtaining permissions and permits to open, not one part of the process or journey was easy. However, there are a few rules I’ve learned about any project:

1. It always takes longer than expected
2. It is always more expensive than expected
3. Never underestimate the importance of the proper tool
4, Never be afraid to ask for help
5. It is always worth it

Can you tell us the story behind how you met your business partner?

Garrett and I met in DC the old-fashioned way – online. When COVID hit we were traveling to Annapolis almost every weekend to work on our sailboat, so we finally just decided to make the move to Annapolis full-time. When we first moved here our goal was to meet as many people as we could to establish a new home for both of us. Whether it was grabbing a beer through the window at Forward or social distance eating at Davis’, we slowly were able to meet some great people. We met our business partners actually at Forward while doing what neighbors do, sharing a drink and enjoying the community. Our partners Lee, Katie, and Joshua have become not only business partners, but friends who we have shared big life moments with, from our opening day at Oscar’s, our wedding, and many others to come.

Contact Info:

• Website: https://www.wheresoscar.com
• Instagram: https://www.instagram.com/wheresoscars/
• Facebook: https://www.facebook.com/OscarsCoffeeEastport/

Image Credits

Lee Snead
Garrett Harper