Jennifer Holmes
Jennifer Holmes is a multi-entrepreneur, founder of Boss Up Digital, and owner and partner in multiple business ventures focused on empowering others through marketing, technology, and business education. She has been working in digital marketing for about a year, though her entrepreneurial journey spans more than 26 years. Alongside her husband, she has helped build and sustain a retail business that evolved over time—from traveling trade shows across the country, to operating brick-and-mortar locations, and now participating in flea markets and trade shows as consumer behavior and the economy have increasingly shifted toward digital commerce. With a lifelong interest in technology and computers, Jennifer was naturally drawn to the rise of artificial intelligence, viewing it not as a challenge but as an exciting opportunity to help make work and business processes easier for others.
As the founder of Boss Up Digital, Jennifer teaches entrepreneurs how to use AI and digital marketing tools in practical, approachable ways that reduce overwhelm and create real business results. She is also a partner in Crystal Forge Tech with two other women entrepreneurs, where they provide AI education, digital marketing support, sales funnel strategy, back-office systems assistance, holistic medicine insights, and additional services such as tax-related guidance. In addition to her business ventures, Jennifer serves as the Public Relations Manager for the Sister Can You Hear Me Foundation in Jacksonville, Florida, an organization that supports domestic abuse survivors, and she is preparing to join the organization’s board of directors. She is also involved with Farmasi, a 75-year-old health and beauty company based in Turkey, where she introduces products to her community through in-person interactions at flea markets, combining digital knowledge with personal, relationship-driven marketing.
Jennifer is passionate about helping others succeed while staying rooted in her personal values of deep faith, positivity, resilience, independence, and service to others. She believes her work is a calling and is grateful for the opportunity to wear many professional hats while making a meaningful impact in her community. Guided by her faith, she embraces the belief that through God all things are possible and is committed to helping others break barriers, learn new skills, and build more sustainable futures through entrepreneurship and technology.
• Sister Can You Hear Me Foundation - Supporting Domestic Abuse Survivors
What do you attribute your success to?
My faith in God is absolutely the key to my success. I hold a very high faith in God, and without Him, I would probably be in a mental institution or dead right now, because I've seriously been through a lot in my 58 years on this earth. My faith in God has definitely steered me through a lot, and without it I would definitely be lost. He has helped me through many, many, many storms, and I'm sure that he will continue to help me through many more to come, because that's just life. I don't dwell on the past and I don't let it hinder me at all, because I can't change what's happened. I don't waste positive energy on negative thoughts. I try to remain very positive as much as possible, and I'm grateful for all the little things. I've been through homelessness, living in a park for an entire year when I first met my husband, and I've survived multiple abuse since I was a child - but that doesn't define who you are. I'm a survivor, and I'm determined. I determine my outcome, and people have to make their own outcome. They can't let the things in their life determine what they do. You have to make those determinations yourself.
What’s the best career advice you’ve ever received?
The best career advice I’ve ever received was from my husband, who encouraged me to move our family business into the digital space. That early guidance pushed me to embrace online business strategies and explore emerging technologies, including AI tools, which helped modernize our approach, expand our reach, and increase efficiency. His encouragement taught me the importance of staying adaptable, continuously learning, and being open to innovation in order to remain competitive and grow professionally.
What advice would you give to young women entering your industry?
Just do it. Don't be scared. The thing that I run into a lot with my students is they're scared of failure, and you cannot be scared to fail. Do not be scared to fail. Just do it. You're never gonna know what you can succeed at if you don't try. Don't be afraid to fail - we fail every day. You get up, and you start over, and you try again, and you learn from your mistakes, and you do better the next time, and before you know it, you're a millionaire. Nobody's perfect, so we all make mistakes, and we all have to learn through them. Even the gurus with all the certificates, the woman in her kitchen just like myself - we all learn from them, and eventually, we find our groove. So, just do it. You don't need fancy certifications or education - I'm not educated, for real, for real, I don't have certifications and all that carrying on, but I'm out here doing it, and there's nothing stopping anybody from doing it. I have been broke, living in a park for an entire year, I've been homeless, I've survived abuse since I was a child - it doesn't define who you are. I'm a survivor, I'm determined, and I determine my outcome. People have to make their own outcome. They can't let the things in their life determine what they do.
What are the biggest challenges or opportunities in your field right now?
The biggest challenges and opportunities in my field right now stem from the decline of brick-and-mortar retail, which creates both urgency and opportunity to transition businesses to digital channels. At the same time, AI is evolving at a rapid pace, presenting the chance to educate others on its potential while also requiring me to continuously stay ahead of new tools and technologies to remain effective and relevant.
What values are most important to you in your work and personal life?
The values that are most important to me in both my work and personal life are deep faith, positivity, resilience, and independence, alongside a strong commitment to helping others and breaking generational cycles. These principles guide my decisions, shape my interactions, and motivate me to create meaningful impact in everything I do.
Locations
Boss Up Digital
Jacksonville, FL 32204