Alright – so today we’ve got the honor of introducing you to Gwendolyn Young. We think you’ll enjoy our conversation, we’ve shared it below.
Gwendolyn, thanks for taking the time to share your stories with us today So, let’s imagine that you were advising someone who wanted to start something similar to you and they asked you what you would do differently in the startup-process knowing what you know now. How would you respond?
Wow, this is such a great question. For me, there are a few things I would have done differently based on the insights and experience I have now. The top three that come to mind:
– I would have built and leveraged strategic relationships and partnerships. My business has been largely referral based for years, which is amazing, because it shows that our clients value our service, work and relationship so much that they want to tell others about us. These partnerships have been integral to our business being able to grow, hire more team members, and increase our brand visibility.
– I would have joined some of sort of community on day one. Largely because of the the relationships, but also because of the access to experienced mentors and business owners who have gone through the building phase already. Being able to cut the learning curve in my business was super helpful when I decided to go the agency route. I truly believe if i had not gone at it so long solo, I would have eliminated some mistakes, not hesitated on opportunities, and increased our positioning faster.
– I would have leveraged social media and other low-cost marketing opportunities! When I first started working in my business, I was so focused on delivering client work and implementing systems, that I did not really market my business. Now that I understand the power of visibiity and positioning yourself as an authority in your field, I know that this strategy would have definitely allowed me to grow faster.
I am already a systems thinker and I love processes, so implementing systems was easy for me. Coming from a corporate background it was natural for me to think in terms of standard operating procedures, budgets, policies and all the backend things; however, being visible, networking, and branding were all new to me. I know these three areas would have definitely contributed to a faster growth rate.

Gwendolyn, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I was a late bloomer. I always tell my children that I didn’t really start living until I was nearly 30 years old. At the age of 28, I started my first real job and quickly fell in love with administration and operations. I held several positions in corporate america working for a large healthcare system where I had the privilage to serve and support some of the most amazing executives, physicians, staff, and patients. However, in 2013, I was diagnosed with Systemic Lupus and had to retire from my corporate job to focus on my health and recovery. It was during recovery that I said “Lord, what am I supposed to do? How can I take care of myself, do something I love and still contribute to my family financially?”
I heard his response clearly, “it’s in your hands.” I didn’t really understand what that meant at first. So I started thinking about all the admin and operations work I did in the corporate world for nearly 15 years and began researching if that was possible to do in the virtual space, and found there was an entire industry online doing what I was good at.
I had no plans or desire to become an entrepreneur, but I had a choice to make. Go back to Corporate America and deal with the bureaucracy when it came to needing time off, doctor’s visits, etc., continue fighting the social security administration to prove I needed support, OR create a business that had the potential to replace my corporate income, give me the freedom and flexibility I needed to take care of myself, and work with amazing people across the globe. I chose #3.
And then I put my head down and went to work. I created a website, created job profiles on every job site I learned about, and started telling my friends and family that I was in business. And then my mother became my first paying client. Six months later, I got my first non-mom client lol. It was a psychologist in Florida who found me on one of those job sites and she took a chance on me. And since then, I have been providing administrative support to visionary CEOs, executives and business owners across the globe, helping them to solve two of their biggest problems: redeeming their time and staying focused on strategic decision-making and leading their organization.
It’s so rewarding to understand both sides of the equation with the work that I do. I am a CEO and I’ve supported CEOs for decades; so I understand exactly what they need. This is what sets me and our team apart in this industry. It’s easy to be a virtual assistant; it’s not so easy to be a strategic partner who understands how to provide administrative support to help executives advance their mission and goals.
I am most proud of the fact that I have built something that supports harmony between work and life, provides jobs for other women, gives me an opportunity to work with my family, makes a significant impact in our clients’s lives, and has the potential to thrive long after I exit the business.
It’s important to me that our community, whether that be clients, followers, fans, team members, etc., know that this isn’t just work for me, it’s what I have been purposed to do and I don’t take it lightly. My wish is that our core values are felt and seen when our community engages with us.
I’ve done some other cool stuff too like:
Studied at some of the top private institutions in Illinois.
Earned a Masters Degree in Organizational Leadership from Lewis University.
Earned a Bachelors Degree in Business Information Systems from DeVry University.
Been recognized as one of the most influential women in business by the Daily Herald Business Ledger in partnership with the National Association of Women Business Owners – Chicago Chapter and the Women’s Innovation Network.
Received the Elizabeth Timpton’s Girls Mentoring Award for my work in the community by Passages Alternative Living, Inc.
And was one of twenty emerging leaders in the US selected as the receipient of the 2012 Judith O’Connor Scholar Award for Emerging Nonprofit Leaders by BoardSource.

We’d love to hear a story of resilience from your journey.
The leap into entrepreneurship with the diagnosis of a life-changing health challenge, limited capital, and no experience running an entire company was frightening, And yet, I chose to keep going. I used my background in administration, leaned on my expertise from managing two ambulatory care centers, supervising a team of 20+ staff, and strategies supporting high level C-Suite executives to build a results-driven virtual assistant agency, which is now a multi-six-figure company. I embraced every hosptial stay with hope and determination, and used it to identify gaps of where systems were failing and to set my business up in a way that would really support what I needed most; flexibiity and really great people to work with.
I leveraged automation because I knew that hospital stays would most likely become part of my new normal for awhile, so I perfected ways to keep alot of things going; even when I couldn’t.
I got really clear on who I wanted to work with and I took the risk of being transparent with my clients about my health struggles, so there wouldn’t be any frustration on days when I could not show up. They were amazing at helping me to implement slack time into deadlines for the unexpected just in case moments.
I leveraged my support system. My family’s support made all the difference.
The most important thing about my journey has been remaining flexible and open, committed to implementing systems, keeping a positive attitude and leaning on my support system.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?
I had to unlearn the mindset that doing it all myself was the only way to maintain control and ensure success. I realized that in order to scale and truly grow my business the way I envisioned, I had to delegate responsibilities, build a team, and empower them to take ownership of their roles. The turning point came when I lost a great a client and a contract opportunity that could have transformed my business. I wasn’t able to keep up with the all the meetings the client needed; the workload was increasing, and he needed more support. He also wanted me to hire a virtual assistant and manage them and take on more of a management role. I unforuntately didn’t have the capacity for more work and I also had not thought through the process of hiring another virtual assistant, training them, and transitioning them to support the client. And as such, I lost the client and the first opportunity to become the administrative service partner for his entire real estate development company. I had come to a crossroads, either continue trying to do everything myself or start trusting others to deliver services to clients and find someone to help me manage other parts of the business.
It was enlightening, humbling, and a great learning opportunity for me as a business owner. AND we now have a great seamless process for sourcing, recruiting, hiring, training, and transitioning support staff for clients.
Contact Info:
- Website: https://www.yourvirtualadminexpert.com/
- Instagram: https://instagram.com/youradminexpert
- Facebook: http://www.facebook.com/youradminexpert
- Linkedin: https://www.linkedin.com/in/youradminexpert/
- Twitter: http://www.twitter.com/youradminexpert
- Youtube: https://www.youtube.com/@leadingbehindthescene
- Other: Podlink: https://pod.link/977257750






Image Credits
Photographers:
Tina Mason
Shanel Romain
Randell Williams

