CENTREVILLE — Courtney Smith was genuinely surprised when the Queen Anne’s County Chamber of Commerce awarded her Entrepreneur of the Year at their annual Business Award Ceremony that takes place in October.
As a fresh-out-of-college graduate from Arizona State University in early 2008, Smith decided to take a risk after being “randomly” asked to join the pre-marketing team at a luxury resort that was run by InterContinental.
After a year of marketing the $300 million dollar property’s spa and restaurant to locals in the area, Smith would shift away to operate various account managing positions to support herself as she worked to eventually start up Smith & 7 SEO and Digital Marketing Agency in 2009.
“I decided to start my first business in a recession, which seems to be my trend,” Smith said, with a chuckle.
Like all entrepreneurs, Smith said it was difficult in the beginning. Along with her day jobs, working on securing clients for what was then called CS Creative Suite, she took up a bartending job in downtown Annapolis, using the cash to finance the budding business.
“Luckily, I had a good reputation in marketing, at least out in Arizona. I was [also] well connected in Annapolis just from bartending and you know, my first few clients took a chance on me, thank goodness,” she said. “I [thought] myself incredibly low as we all do in the beginning, [and] had some really rough lessons along the way.”
Smith started her business during the 2009 recession, but also during a time where graphic designing websites that offer baseline free services like Canva did not exist—businesses had to invest a few thousand dollars to a company that would develop a website for them.
And that’s what Smith did.
“So, I paid somebody $3,000 of hard-earned bartending cash to build my website,” she said. “I had saved [that] $3,000 to have somebody build my site which doesn’t sound like much today but in 2009, it was in a recession, and they took my money and never finished building my site.”
“That’s how I got into website development and SEO (Search Engine Optimization). I swore that would never happen again. For the next two years, I taught myself how to build websites and verse myself in the digital side of things,” Smith added.
Smith’s clientele consisted of mainly those within the hospitality business at first since that industry encompassed her background, but the more technical she became in SEO, the more she started to branch out.
“What we do now is work with clients that have a need for online lead generation, so most of those businesses are home-based service businesses,” she said. “These businesses range from patio contractors and power washers, I also work with a gym in Anne Arundel County; just anybody—any client—that needs to get to the top of Google in a very specific location.”
The only thing she does not do, Smith said, is e-commerce which is basically just the trading of goods and services via the internet.
Business did not stop at SEO work for Smith. In the next decade, she would own and develop three more companies from the ground up using her background in marketing and networking skills—one of which, despite falling flat, would offer the opportunity of a lifetime.
In 2012, Smith developed an idea to build a website that would optimize the bachelorette party planning process.
“Because I was in the luxury hotels and events industry, I’ve always seemed to always be the go-to girl to plan bachelorette parties, especially out in Scottsdale where I used to live,” she said. “Back in the day again, there was no Uber, things were very compartmentalized, and so it was a lot of work.”
“I planned my best friend’s bachelorette party, and she had very high expectations: book the limo, book the spa, book the hotel. It was like hurting cats,” she said. “ So, selfishly, when I figured out how to do websites I was like ‘I am never doing this again, if I had such a hard time doing this, other people must as well.’”
Taking the concept of the wedding planning websites, she thought of a bachelorette planning website—because the bachelorette party comes before the wedding—allowing planners to build their itinerary online for free.
Thus, Bashelorette was born. The online itinerary would gain a small following earning $36,000 in advertising before the site even launched. Trying to expand to other cities was difficult because Smith realized that in order to do that, they would need an in-person presence. Six months into the operations, an investor would later push Smith to take her product to Shark Tank.
Smith would rise to the challenge reaching the final round, but since the company did not even have a year under their belt yet, she couldn’t predict the trends of the business. Smith was eventually dropped from the popular Tv Show, but would be invited back again, rising to the finale with a potential film date; however, the services Bashelorette offered were ultimately deemed “unpatentable” the shows ‘sharks.’
“There’s no shortcut to waiting for a successful business,” she said. “Sometimes it absolutely sucks and you’re crying and you’re like ‘where did I go wrong?’”
Overall, Shark Tank was just a “huge time suck,” she noted. As a single-mom to her son, she wanted to be able to develop a work/life balance.
As of right now Bashlorette is still a business that exists, but Smith is not actively spending her energy building the company as she turned her endeavors to her two recent assets: 1631 Event Venue—a space in Stevensville that can be rented out for any type of event including baby showers and birthday parties— and Chesapeake Bartenders, a company that was form as early as 2019 that offers professional bartending services that stems from her connections with the Annapolis bartending scene.
They offer hourly bartending rates, all inclusive bartender for hire packages, mobile bars, signature drink creation, bar table and glassware rentals + beverage catering to help create a custom drink menu for your event.
Though she has only lived in the county for five years, she certainly has made a lasting impact on the community she does business with, according to the Chamber’s President Linda Friday.
“She’s very outgoing and has a great vision of being an entrepreneur, there was no doubt she’d win the Entrepreneur of the Year award,” Friday said.
For now, Smith said that the entrepreneurial side of her needs a break to focus on her personal life.
“I’m 41 now and my son’s 10, and like many people my age, I think that I’ve grinded pretty hard for a long time,” she said. “I’ve worked really, really hard ever since I started in the hotel industry, and I just want quality time with my son now. So, what I have found where my passion is now is teaching people.”
Smith has recently started to teach SEO courses to women, because in her words, a lot of women—especially solopreneurs— are very overwhelmed by marketing, and she has found that they don’t know how to build a website.
To help with this, she set up a class for three local Queen Anne’s County businesses to teach them the basics of SEO and website building for their business, she plans on developing a structured course that would be a available to other people online, charging a fee for the class.
She hopes that the course will launch in February of 2023.
“My dream in life is to be a motivational speaker, my big thing is, if it helps somebody, great, if I can motivate you and kind of break it down and simplify it then the goal has been accomplished,” she said.