For those who never truly saw themselves working in a traditional 9-to-5 desk job environment, the thought of opening a business has probably come to mind throughout the search for a ‘dream job.’ Today, social media makes entrepreneurship look effortless, and while many resources have become available for those daring to take on the challenge, the “aesthetics” of the business owner lifestyle certainly blur the line between expectations and reality. The truth is that opening a business is hard work…and a lot of it. As much as one should have high hopes for their business and strive for success, entrepreneurs have to face failure – and more importantly, find ways to overcome it. In fact, there are many women entrepreneurs within the Hampton Roads community who have faced the struggles that accompany business ownership and found ways to triumph over them. To learn more about the entrepreneurial experience, I reached out to some of these women to gather their best advice for other aspiring business owners.
TAO Beauty – Tesora Overstreet – The Beauty Industry
Founded in 2024, TAO Beauty has become a primary representation of success within the entrepreneurial journey for women at Old Dominion University (ODU). Its founder, Tesora Overstreet, started her journey making skincare products as a hobby in 2021, before growing her passion into a business at only 18-years-old. At TAO Beauty, diversity is celebrated, their skincare products are catered to all skin types and tones, and their focus is on building an inclusive environment that promotes self-love and empowerment. With body mists, oils, scrubs, and butters, alongside a new line of comfortable clothing, TAO Beauty is a prime example of a growing beauty business in the Hampton Roads area.
Wild Works of Whimsy & Southern Branch Nursery – Trista Imrich – The Horticulture Industry
Since 2023, Trista Imrich has taken on the responsibility of both Wild Works of Whimsy and Southern Branch Nursery, sister companies that not only create functional and beautiful landscape designs but support local wildlife conservation efforts. While Southern Branch Nursery focuses on providing a wide range of Virginia native plants, nurtured in recycled pots from locally-collected seeds, Wild Works of Whimsy offers plant consultation and landscape design services that provide solutions to local home and property owners with a focus on conservation landscaping and stormwater management.
Imrich’s involvement with Lynnhaven River NOW, a local watershed nonprofit, the Virginia Conservation Assistance Program (VCAP), and the Chesapeake Bay Preservation Area (CBPA) have enabled her to become a prominent sustainability and horticultural advocate within Hampton Roads. Having partnered with Tidewater Compost, she has even worked to create a local drop-off kiosk at the nursery for composting. Additionally, since serving as a Surface Warfare Officer in the US Navy, Imrich has used her business as a means of empowering both women and veterans through employment and mentorship.
Sinful Treats – Stephanie Rolla – The Food & Beverage Industry
Founded in 2013 by Stephanie Rolla, Sinful Treats is a woman-owned and family-operated business. Starting her journey with custom birthday and wedding cakes, Rolla has since made impressive strides with her business, now operating multiple business locations throughout the Hampton Roads area. With homemade baked goods and dog treats, this business is working to the bone to satisfy the sweet tooth of every person and pup within the local Hampton Roads community.
Social media is an extremely helpful resource, but also be sure to trust in yourself!
Social media has become a major tool for small business owners around the world, however its effectiveness in drawing in customers isn’t always accurately represented. When it comes to the role of social media in TAO Beauty’s business operations, Tesora Overstreet commented that, “the reality for many smaller business owners is social media takes quite a bit of effort before it becomes fruitful…[in-person sales] creates a genuine connection and trust that social media can’t foster, especially when it comes to building a trust strong enough for someone to take a risk on your product.” Despite this, she hasn’t disregarded the usefulness of social media in progressing her business.
She notes the different useful tools that platforms such as Instagram and Facebook offer to business owners by saying, “I greatly appreciate the ability to create ads to get more eyes on a post, channels to let my audience know directly where I will be for a pop-up market, the product and website linking feature, and other analytics…once you master the algorithm you have the ability to reach THOUSANDS of potential customers or business opportunities!”
While many influencers comment on the massive audience growth that social media sparks, it’s important for aspiring entrepreneurs to remember that audience members don’t necessarily equate to customers. In addition to this, social media can often be a source of negativity and a place where individuals vocalize opinions rather than express legitimate business concerns. Sinful Treats owner, Stephanie Rolla, does an amazing job in illustrating this point by saying, “…you’re not going to make everybody happy, and everybody is not going to say nice things all the time…” Throughout her experience, she’s learned to utilize social media but ultimately doesn’t allow it to control the decisions she makes in regard to her business and products.
Networking is a skill best utilized intentionally, with a strong support system.
Naturally, challenges emerge with business ownership, and the uncertainty that accompanies these challenges can easily become too much for an individual to navigate on their own. For business owners like Overstreet, her faith is one effective support system that helps her to stay grounded throughout her entrepreneurial journey. Rather than taking challenges and failures as a sign to quit, her faith has allowed her to see the brighter side of every hardship and recognize the growth these setbacks have enabled. She says that, “…through any problem I pray and ask God for guidance, this especially helps when I get in my own head about the future of my business…Through each unfavorable experience I am able to build resilience, determination, and grit…Now I have the maturity to see past my negative rhetoric and continue moving forward despite any fears I may have.”
Alongside having a steady internal support system, individuals should make themselves aware of the resources available to them within their community, and take advantage of their services in order to build a strong external support network. Trista Imrich, owner of Wild Works of Whimsy and Southern Branch Nursery, reflected on her own experience navigating these uncertainties by saying, “There were so many questions around regulations, compliance, and best practices that weren’t obvious and that uncertainty could be overwhelming. I learned the hard way that not all advice is equal, but over time, I’ve built a strong network of knowledgeable advisors, accountants, and attorneys to support the business. I also took advantage of great local resources, like the ODU Women’s Business Center and the SBDC [Small Business Development Centers], to help me find my footing.” Alongside sharing her experiences with networking, however, she also shares her concerns. Her advice reminds aspiring entrepreneurs to bring intentionality to their networking practices, as not every individual’s advice is credible or suitable for every (or any) business.
In addition to utilizing the resources provided by organizations with the goal of empowering entrepreneurs, aspiring business owners should also consider the experience that other local entrepreneurs have to offer. To not only gain a support system in the progression of her small business, but also provide support to others, Rolla has been able to form relationships with fellow business owners within her local community, saying, “[Business ownership has] definitely made me more of a service-minded individual and making sure that I’m supporting the people who are supporting me…We do a lot of stuff with a lot of other businesses in the area, and we’ve actually developed a small group of us that get together and find other ways to support each other.”
Financial considerations are a major source of small business ownership stressors.
To help ease the daunting shadow this aspect casts over the idea of business ownership, these entrepreneurs have shared the best advice they’ve learned while figuring out what works for their respective businesses. When it comes to vendor opportunities, TAO Beauty remarks that, “There are many licenses you need to get, each of them costing $20-$100. It seems like once you get the license they tell you, you need another. Additionally, I’ve been to a couple of markets where the foot traffic was terrible and I’ve sold absolutely nothing, I lose the $50-$100 I spent on the vendor fee, and another $20 to buy food to eat during the event. It’s extremely discouraging.”
One reality of owning a business is that not every opportunity will be profitable, and it’s important for any business to consider the costs that are associated with the risks of certain opportunities. Understanding the impact of these risks is crucial for decision-making, and any business owner should consider their financial flexibility before jumping into action. To further illustrate this point, Imrich adds that, “One of the biggest challenges has been figuring out when and how to bring on help…hiring comes with real costs and administrative complexity, and it wasn’t always clear if the timing was right…I’ve had to adjust and streamline, and I now operate with a smaller, more intentional team…It’s a constant balancing act between the benefits of extra help and the financial realities.”
Success must be defined on your own terms, not built on the foundation of other’s expectations or experience.
One major point that each entrepreneur made within their interview is the need to ‘follow your gut’ throughout entrepreneurial endeavors. Oftentimes, individuals rely on those around them to contribute their opinions, however this might not always align with business goals. For TAO Beauty, she addresses this topic by saying, “I can’t count how many times I’ve had a product idea and didn’t pursue it because the people around me said they didn’t like it…in the end, I went with my idea, and my customers loved it. Taking risks is so important because you never know what will work until you try; the money will come back, and one mistake won’t stop you.”
Uncertainty can have us wanting to turn to others for advice, however nobody knows the business better than the owner. Imrich shared a similar viewpoint on this topic, commenting that, “…growth isn’t just about doing more or getting bigger – it’s about making the right decisions at the right time…what matters is building something meaningful, sustainable, and aligned with what you care about.” At the end of the day, entrepreneurs have to have a strong sense of what their long-term goals are and what they want their business to personify. Rolla mentions another important aspect of business growth in saying that, “…having a clear vision is great, but also being very flexible with where you see things going is very important, and figuring out how to make what’s currently going on work for you – but not sacrificing what your true to with your business model and plan.”
Invest in yourself; Many people aren’t open minded to women in male-dominated spaces.
This reality is especially true in the field of entrepreneurship. Within Imrich’s experience, she comments that, “…one of the biggest differences has been access – to funding, to networks, and to opportunities…In the green industry specifically, it’s still somewhat unexpected for people to encounter a fully woman-owned and woman-run nursery and design business. That surprise can sometimes come with assumptions – like clients talking down to me or feeling the need to prove my credibility. I’ve responded by investing heavily in my education and certifications…so I have concrete qualifications to stand on.” Through her advice, she reminds other young women of the importance of having a solid foundation of both education and credibility, but also remaining confident in your own experience.
In addition to Imrich’s advice, Rolla offers a similar experience and statement for other young women saying, “In everyday life I think you run into speed bumps for a number of different reasons, being a female [is] one of them…If I had to give advice to anybody it would just be to stay true to yourself and always put your best foot forward in all circumstances because networking is so important in business…I’m always out there, involved, trying to be informed about everything that’s going on, so that when I want to do something or make a change I have the means to speak intelligently on whatever it is.”
Opening a business comes with a series of uncertainties, but the experiences of other entrepreneurs offers insightful guidance that can help to prepare individuals for navigating these challenges. Although the endeavor may be daunting, there are a multitude of community resources available for aspiring business owners to create a stable foundation for their business to build upon. Thankfully, gracious business owners, such as these women within Hampton Roads, do their best to provide experiential advice that prevent others from juggling these uncertainties alone.