Today we’d like to introduce you to Courtney Smith.
Hi Courtney, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstory with our readers?
I think I knew I was going to be an entrepreneur from a very early age. When I was still in single digits, I was picking flowers from the neighbors’ yards and trying to sell those same flowers back to them as bouquets (zero operational costs!) . I wasn’t just the kid with a lemonade stand — I had a mobile lemonade stand. I sold anything and everything I could because I was fascinated by the idea of creating something that people would actually pay for. I made jewelry, did craft shows, and loved every part of the process.
After college, I landed in marketing for luxury hospitality — at the InterContinental Montelucia Resort & Spa in Scottsdale, Arizona. I was part of the pre-opening team, which meant I got to help build that resort from the ground up. I loved that job, but in 2009, my grandmother was diagnosed with cancer, and I decided to move back to Maryland to be closer to her.
It was bittersweet. I loved what I was doing, but I had also been working 80-hour weeks to open that property for 2 years. I remember thinking, If I can work 80 hours a week for someone else, I can definitely work 80 hours a week for myself.
So I went from an incredible office and marketing role to bartending at Armadillo’s in downtown Annapolis to pay the bills while building my own business on the side. That’s when I opened my first marketing agency — back then it was called CS Creative Suite. I focused on hospitality clients: bed and breakfasts, restaurants, bars, and local fundraisers. Little by little, I built a client roster and a reputation.
Eventually, I got into SEO — Search Engine Optimization — and that changed everything. I briefly worked at an SEO startup in Gaithersburg before realizing I truly wanted to work for myself. Once I understood how to rank things on Google, I realized SEO was the key that could unlock almost any online business. It became my superpower.
That skill led to my next venture — a startup called Bashelorette. The idea came from my own experience planning bachelorette parties, which often felt like herding cats. I wanted to make the process easier and more organized. I pitched investors, found sweat equity partners, and launched the site in early 2013. We had early success, earning about $30,000 in B2B ad sales, and then Shark Tank called. We made it to the finals — twice. The first time, they said we were too early. The second time, we were invited to film a major competition show in L.A. (I can’t share who the celebrity host was), and I ended up winning prize money there.
Those experiences were AMAZING! I learned how to pitch my startup, how to fundraise and what can happen when I dreamed big. But I was also a full-time single mom with a six-month-old, and while the startup world gave me amazing opportunities, it wasn’t paying the daycare bills.
I was invited back to Arizona to consult for a boutique luxury hotel in Sedona. I needed stability and benefits, so I packed up and moved back west with my 16-month-old son. I eventually became VP of Marketing and PR for an asset management company in Scottsdale that oversaw hotels, golf courses, spas, and land investments. They allowed me to keep my marketing agency on the side, which was a dream scenario.
Eventually, I returned to Maryland again to be closer to family and rebranded my agency as Smith & 7. The agency specialized in SEO, lead generation, Facebook and Google ads, and WordPress design. I grew quickly, balancing client work with bartending gigs to keep extra cash flowing.
Those bartending gigs sparked another idea. Back in 2013, I’d casually started Apothecary Mixology to book private events, and in 2019 I reimagined it as Chesapeake Bartenders & Events (CBE). I thought it would be a small side hustle — just a way to earn and invest extra money as a single mom. But between my SEO background and the lack of luxury mobile bar services in the area, it exploded.
CBE took off immediately. Even COVID couldn’t stop us — it slowed things down (and was challenging to say the least), but we adapted. Today, we’re one of the premier mobile bartending companies in the Mid-Atlantic, known for weddings, corporate events, nonprofit galas, and private celebrations. We have 1 full time employee and a roster of 20 bartenders. We’re now expanding into catering in 2026, which I am really excited about!
In 2022, I opened 1631 Venue on Kent Island — originally meant to be an office for Chesapeake Bartenders. But when I saw the natural light, the hardwood floors, and the character of that little space, I realized it could be so much more. It became a DIY-style event venue for small gatherings — bridal showers, baby showers, rehearsal dinners, and micro weddings. It’s 1,000 square feet of charm in historic Stevensville, and we offer optional event planning, bar, and catering services. I wanted to venue to be very affordable to locals, as the area already has its share of expensive and large venues. I am proud that the venue has been successful and hosts a variety of special occasions for our customers at a price that is approachable. I even won “Entrepreneur of the Year” in 2022 from Queen Anne’s County’s Chamber of Commerce.
Everything was moving full steam ahead — until early 2024, when I was diagnosed with breast cancer.
It was a shock. I’m a triathlete, an Ironman finisher. I take care of my body and pay close attention to my health. But cancer did not care. Suddenly, my focus shifted from growth and expansion to survival, both personally and professionally. I had to find a way to maintain my businesses while undergoing a double mastectomy, chemotherapy, and radiation at Mercy Hospital in Baltimore.
The team at Mercy was extraordinary — compassionate, supportive, and so empathetic. That experience tested everything I thought I knew about strength. It wasn’t easy on me, my son or my family. But I got through, and am now cancer-free! I even have a full head of hair and some eyebrows again 🙂
I learned after decades of hustling that I could not keep grinding without integrating strategies to calm my body and create space for healing. Are the businesses still going? Yes! I am so proud that despite cancer treatment being a full time job for almost a year, the businesses forged on, and my amazing team is why we are thriving. I could not have done it without them. While I am happy we are busy, especially in the current economic climate, I have but back on marketing clients and have been more picky about what I take on. It used to be “more clients, more bookings, more growth.” I think I have hit a place where I am more mature in my entrepreneurship journey, and I value consistency, building a great team and delivering exceptional results. I don’t say “yes” to everything anymore. I say “yes” to things that are aligned with my personal and professional goals and mission.
I hope this helps provide some insight into my wild journey as an entrepreneur. I would not trade it for anything in the world, despite the fact that it is often unpredictable and there are speed bumps along the way. I am immensely grateful to have the opportunity to lead an incredible team and help people say “I do” and celebrate some of life’s biggest milestones.
Thank you for your consideration!
Courtney
We all face challenges, but looking back would you describe it as a relatively smooth road?
I don’t know any entrepreneurs who have had a smooth ride! So no – it has not been smooth. But that is part of the process. In my humble opinion, an entrepreneur’s job is to solve problems – in the form of products or services. However, often we get the products and services right, not knowing that we will be solving all sorts of other problems along the way. For example, when I launched Bashelorette, is was the first bachelorette party planning website. It was a hit right out of the gate, but the barrier to entry was low. So copy-cats started popping up and literally copying our press releases, website content, etc. It was heartbreaking. We did not have the startup funds to scale as quickly, which is why you see successful bachelorette party sites today, and Bashelorette is no longer around. I think we were a little too early, and we were cash strapped. It was hard to walk away from something that so many people believed in. I have also had private challenges as a single parent. I have been a full time single parent from day one, and although my family and friends have been my village, there have been times I knew if I had a partner or more funding, I would have been able to scale and build bigger businesses. However, all these challenges formed the entrepreneur I am today. I have no regrets and I would not do anything differently. I have learned more through this process than I could ever have imagined!
Can you tell our readers more about what you do and what you think sets you apart from others?
We’ve talked a lot about business (which I love!), but I have found that being active and competing in endurance sports has also provided “moving meditation” and a healthy outlet for me. I think it is really important for entrepreneurs to take good care of their minds and bodies. Often, we work so hard on our businesses that we neglect ourselves. I joke that I chose triathlon, because it is so hard and it will force you to workout – especially if you have a race on the calendar. So triathlon and running has been the thing that forces me to stop working and go for a run, ride or swim. This ensures that I avoid burnout (which has happened to me before). It also sets a good example for my son to show him that Mom takes care of herself too. In 2019, I became an Ironman at Ironman Maryland. I swam 2.4 miles, cycled 112 miles and then ran a marathon. It was one of the hardest things I have ever done, but I am so glad I did it. My son was at the finish line and I proved to myself that day that I can do really hard stuff! I think too, when I was diagnosed with breast cancer at age 43, being a triathlete helped me approach it “one mile at a time” which is always my mantra during races. I knew how to put my head down and be patient with the process. So I try to recruit others into triathlon because it has truly been a force of positive in my life!
What’s next?
I am really excited about the future. For now, I am so happy to feel like myself again and be healthy. Even after treatment, I really struggled and felt pretty bad/tired. Now that I feel better, the plan involves expanding catering operations to Chesapeake Bartenders and Events offerings. I just passed the certification to apply with the County and obtained our commercial kitchen, which is a requirement. So catering is a big step for us!
I do want to get into public speaking in order to help other women facing challenges such as health challenges or because they are single moms. I really don’t know how to get into public speaking but maybe in 2206 I will explore that, as I really like helping others.
Pricing:
- Chesapeake Bartenders: pricing is custom but our average invoice is $1000
- 1631 Venue Rental – Starts at $400 for 6 hours on weekends
Contact Info:
- Website: https://www.chesapeakebartenders.com/
- Instagram: https://www.instagram.com/smithcourtneymarie
- LinkedIn: https://www.linkedin.com/in/courtneymsmith
- Youtube: https://www.youtube.com/@courtneysmithtriathlon
- Other: https://1631venue.com/
