Renegade Ventures

Today, Ellie and Maggie are joined by Jenna Ahern of Guardian Owl Digital. As a college student, she and two other women co-founded Bluegrass Premier, a field hockey club in Louisville, simply because they saw a need for it. She did not view this as business ownership at the time but rather as a practical solution to an unmet demand. After setting up the club, she decided to focus on her career in the automotive industry. It wasn’t until later that she recognized her entrepreneurial tendencies. 

 The discussion turns to how both Jenna and Maggie began their careers in the male-dominated automotive industry. Recognizing the industry’s shift toward digital marketing, Jenna leveraged her expertise in Google Ads and analytics to help businesses optimize their digital investments. This led her to start Guardian Out Digital, a venture quickly grew, fueled by a demand for digital marketing expertise among small and mid-sized businesses struggling to navigate the online landscape.

Jenna admits that she did not originally plan to build a company with employees; instead, her business evolved naturally out of a need she identified. At just 24 years old, she took a leap into entrepreneurship. Jenna draws strong parallels between her experience as an athlete and her approach to business leadership. Jenna also discusses the challenges she faced as a woman in the automotive and business sectors, where pushing back against established norms was often unwelcome.  Early in her career, she had to learn how to strategically navigate workplace politics, often tempering her opinions to avoid conflict. However, this ultimately led her to realize that entrepreneurship was the best path for her.

 After taking full control of the company, Jenna faced the reality of sustaining and scaling the business. The conversation shifts to the nature of Jenna’s business, an SEO and digital marketing agency, and how many clients initially misunderstand the complexities of online advertising. Her motivation for starting the company stemmed from a desire to educate and guide small businesses toward smarter digital marketing strategies. The role of advisor and advocate solidified her purpose in the industry, helping businesses navigate an increasingly complex digital landscape. Jenna stresses the necessity for business owners to educate themselves on digital marketing fundamentals, even if they plan to outsource it later. By doing so, they can better understand how these platforms connect and when the right time is to invest in professional services. She emphasizes that SEO is a long-term strategy, not a quick fix, and that small businesses should only invest in it when it aligns with their financial and operational goals. Before investing in SEO or paid advertising, they need clarity on their customer base, their value proposition, and why their business exists.

GuardianOwl has refined its expertise in digital marketing across various industries, including e-commerce, B2B, manufacturing, and automotive. Over the years, they have tested different digital marketing approaches and partnerships, ultimately building a trustworthy, results-driven process. In closing, Jenna looks forward to the future of her women-led company. 

Key Topics: 

1:08 - Introducing today’s guest Jenna Ahern. 

5:03 - Jenna’s Experience in the Automotive Industry. 

10:16 - The progression into Business Ownership. 

13:32 - Navigating Male-Dominated Industries. 

17:32 - Forming a Business Partnership and its Challenges. 

20:58 - Building a Sustainable Business Model. 

24:19 - Laying the Foundation for Digital Marketing Success. 

26:34 - The Reality Behind Entrepreneurial Success. 

31:31 - Servant Leadership and Business Growth. 

39:12 - Building a Support Network for Women Entrepreneurs. 

42:22 - Rebuilding and Expanding GuardianOwl. 

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What happens to your business if something were to happen to you? Who takes over when you retire? If someone walked in today and offered to buy your business, what would the magic number be? If you don’t have the answers, we get it. And so does Jessica Fialkovich, whose business consulting work at Exit Factor is designed to prepare business owners for all the above.

Experiencing the layoffs of 2008 was an eye-opening moment for Jessica. She realized that no corporate job was truly secure and that she would rather take control of her future than be at the mercy of decisions made by corporate executives. This realization led her toward entrepreneurship, valuing the autonomy and risk-taking aspects of business ownership over the false security of traditional employment. After losing her corporate job, Jessica and her husband decided to open a luxury wine shop in Southwest Florida, using their savings and guidance from friends in the industry. Despite being new to the field, they embraced the challenge and foundsuccess by entering the market during an economic downturn when many competitors were struggling or closing. Jessica and her husband entered the wine business with complementary skill sets—Jessica’s expertise was in sales and marketing, while her husband had experience in finance and product buying from his family's fish business. At just 24 years old, they had the advantage of not having financial burdens like a mortgage or children. This minimized their risk and gave them the freedom to take a leap into business ownership. Jessica shares an important lesson for entrepreneurs: business success is not necessarily about industry expertise but about knowing how to run a business. After 39 months of owning the wine business, Jessica and her husband decided to sell the company and move back to Colorado. The experience selling her business exposed her to the flaws in the brokerage industry.

While their broker found a buyer, he did little else to support the transaction. Jessica’s frustrating experience with her own business sale inspired her to launch Exit Factor, a company that helps business owners prepare for their exit. Many entrepreneurs, like Jessica, do not plan ahead and miss opportunities to maximize their sale price. Exit Factor works with business owners to improve profitability, reduce dependence on the owner, and ensure the company operates efficiently, ultimately increasing its value and making the exit process smoother.

Jessica explains that franchising success depends on strong systems, leadership, and the ability to train others. Many business owners mistakenly believe they can simply convert their existing business into a franchise without considering the extensive support required. In closing, Jessica highlights how business owners can connect with Exit Factor for guidance in preparing for a successful exit. The company’s website provides resources, including a valuation calculator and a directory of franchise locations across the U.S. She also highlights her book, Getting the Most for Selling Your Business, available on Amazon, and teases an upcoming book that will focus on the early stages of exit planning, set for release in May.

Key Topics:

1:23 - Jessica’s Early Career Aspirations.

4:17 - Leaving the Sports Industry and a Career Shift.

8:42 - Venturing into Business Ownership.

13:35 - The Reality of Entrepreneurship and Industry Adaptation.

15:00 - Exiting the Wine Business and Moving Forward.

21:30 - Launching Exit Factor.

25:17 - Navigating Succession Planning Conversations.

29:12 - The Small Business Exit Gap and Its Impact.

38:14 -The Challenges of Franchising and Leadership.

43:23 - How listeners can connect with Exit Factor.

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Ellie and Maggie talk entrepreneurship with Rivergreen Cocktails' founder Danielle Mann.