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Overcoming Self-Doubt: Essential Lessons from a CEO Who Grew Her Business 9x in 7 Years

When Jessica Moseley stepped in as chief operating officer of her mother's assistive technology and sign language interpreting company, TCS Associates, in 2008, it had five employees and generated $800,000 in annual revenue. By 2015, the Maryland-based firm had expanded to 62 employees and surpassed $7 million in revenue. That year, Moseley restructured the business, separating its technology and interpreting divisions into two entities and taking the helm as CEO of TCS Interpreting. Her secret to success? Trusting her decisions—even when it wasn't easy. A member of Entrepreneurs' Organization since 2015, Moseley reminds fellow entrepreneurs that failure is part of the journey.
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“There are definitely many times of loneliness and doubt,” she says. “Learning to trust my decisions and be comfortable making mistakes is an acquired trait—which I am still learning—but it keeps me humble.”

Q: Tell me about your business and how it started.

TCS Interpreting was founded by my mother, Myrna Aiello, in 1982 as Technical Computer Services (TCS), a retail computer store focused on assistive technology. After earning my master's in human resource management and working for other companies, I joined in 2008 as COO following discussions with my parents. We had five employees and $800,000 in revenue then. By 2015, when I became CEO, we had 62 employees and $7.2 million in revenue.

Q: What challenges did you face growing your business from 2008 to 2015?

The biggest hurdle was building a strong identity and culture amid 200% annual growth. We lacked time for processes, procedures, or a defined culture. Balancing staff readiness for surging workloads without burnout was key—and I'm still learning.

Q: What personal challenges have you encountered on your entrepreneurial journey?

Like most entrepreneurs, I've faced loneliness and self-doubt. Trusting my decisions and embracing mistakes is a skill I'm honing; it keeps me humble. I'm hard on myself but recognize my limits—and I'm proud of that.
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Q: What sets your brand apart?

Our employee-focused programs, like mentorship, professional development, scouting, and recruitment, create an engaged workforce. Our four core values—transparency, growth, equality, and collaboration—guide everything we do with integrity.

Q: How did you first hear about the Entrepreneurs' Organization?

A West Coast family member, who was a member, urged me to join for over a year before I applied. I've been in for two years and haven't looked back.

Q: Why is a mentorship process vital for your company?

In interpreting, bridging graduation to national certification takes years of practice. Mentorship shows commitment to growth and the industry. It boosts confidence, satisfaction, loyalty, and innovation.
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Q: What challenges arose in developing your mentorship program?

Finding time for mentor training was tough initially, but we prioritized it with video trainings and calls. We aligned it with our growth and collaboration values. Other hurdles: choosing a philosophy (we selected Vygotsky's zone of proximal development), framework, mentor selection, scheduling, challenging assignments, and fostering a mentorship culture across departments.

Q: What advice for entrepreneurs building mentorship programs?

Anchor it in your values—ours emphasize growth and collaboration. Though costly upfront, rewards in loyalty and values-driven work pay off. Gain buy-in by asking employees for mentor suggestions and intern needs. Standardize but customize. Use multiple mentors for diversity. Track what works, require signed contracts outlining expectations.

Q: What's next for you and TCS Interpreting?

We're expanding nationwide in business and government sectors, growing remote video interpreting, and refining our mentorship to bridge education-service gaps.
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This article originally appeared in the November 2017 issue of SUCCESS magazine.