Empowering Women Entrepreneurs Through Mentorship and Business Education With Monica Smiley

Monica Smiley is the Publisher and CEO of Enterprising Women, a print and digital magazine reaching more than one million entrepreneurs worldwide, and the President and Founder of the Enterprising Women Foundation. With a background in journalism, publishing, and entrepreneurship, Monica has dedicated more than 25 years to recognizing, connecting, and supporting women business owners. She leads the Enterprising Women of the Year Awards Celebration and Conference, which honors accomplished women entrepreneurs, and oversees the foundation's three signature programs: Young Enterprising Women, Peace Through Business, and Entrepreneurs of Purpose. Through education, mentorship, recognition, and international outreach, Monica helps women entrepreneurs strengthen their businesses, develop leadership skills, and create lasting economic and community impact.

Here’s a glimpse of what you’ll learn: 

• [02:49] How Monica Smiley's publishing career inspired her to launch Enterprising Women magazine in 2000.
• [05:12] How the Enterprising Women of the Year Awards evolved from a small recognition program into an international celebration of entrepreneurship.
• [08:29] Why Monica created programs that introduce young women to entrepreneurship, STEM careers, and mentorship.
• [11:52] How financial literacy education helps students develop practical money management skills.
• [14:32] How the Young Enterprising Women National Leadership Conference creates opportunities for students from underserved communities.
• [17:47] How Peace Through Business provides training and mentorship to women entrepreneurs around the world.
• [21:33] Why supporting women-owned businesses creates economic opportunities and stronger communities.

In this episode:

What does it take to build an organization that empowers women entrepreneurs across generations and around the world? For many women business owners, access to education, mentorship, recognition, and meaningful professional connections can make a significant difference in their entrepreneurial journeys. Yet these opportunities are not always readily available, particularly for young women and entrepreneurs in underserved communities. Creating lasting change requires more than recognizing success. It requires building programs and support networks that help women develop the knowledge, confidence, and relationships needed to pursue their goals.

Monica Smiley has spent more than two decades creating opportunities for women entrepreneurs through Enterprising Women magazine and the Enterprising Women Foundation. What began as a publication dedicated to sharing the stories of successful women business owners has expanded into an international network of recognition, education, and mentorship programs. Monica explains how the Young Enterprising Women program introduces high school students to financial literacy, STEM careers, and successful women leaders, while Peace Through Business provides established entrepreneurs with practical business training and mentorship. She also shares how these initiatives continue to evolve through strategic partnerships, volunteer involvement, and a commitment to helping women create economic opportunities for themselves and their communities.

In this episode of Systems Simplified, Adi Klevit is joined by Monica Smiley, Publisher and CEO of Enterprising Women and President and Founder of the Enterprising Women Foundation, to discuss the power of mentorship, entrepreneurship education, and purpose-driven leadership. Monica shares how she launched Enterprising Women, developed its annual awards program, and expanded the organization's impact through educational initiatives serving women around the world. Adi brings her perspective as an Enterprising Women of the Year award recipient, advisory board member, and Entrepreneurs of Purpose participant, highlighting the value of meaningful connections and community involvement. Together, they explore how structured educational programs, strong partnerships, and supportive networks help women entrepreneurs build businesses, develop leadership capabilities, and create lasting legacies.

Resources mentioned in this episode:

• Adi Klevit on LinkedIn
• Business Success Consulting Group 
• Monica Smiley on LinkedIn
• Enterprising Women Website
• Enterprising Women Foundation Website

Quotable Moments:

• "We just wanted to be a voice for women entrepreneurs at that time."
• "We love shining the spotlight on the women who are there and really creating a top-notch educational program as well."
• "We see that it's really changing behavior."
• "The resilience of these women is just phenomenal."
• "We see that the need is greater than ever there."

Action Steps:

1. Build meaningful professional relationships through mentorship. Seek opportunities to connect with experienced entrepreneurs who can provide guidance, encouragement, and practical business insights. Consider becoming a mentor yourself to help emerging leaders develop confidence and navigate the challenges of entrepreneurship.
2. Invest in financial literacy and practical business education. Strengthen your understanding of budgeting, financial planning, marketing, and other essential business fundamentals. Support educational initiatives that introduce these skills to young people and aspiring entrepreneurs, helping them make informed decisions about their financial futures.
3. Create opportunities for recognition and professional connection. Participate in entrepreneurial organizations, conferences, and awards programs that celebrate business achievements and encourage collaboration. Use these opportunities to build relationships, exchange knowledge, and connect with potential partners and mentors.
4. Develop partnerships that expand your organization's impact. Identify businesses, educational institutions, nonprofits, and community organizations that share your mission. Collaborate on programs that combine resources, expertise, and networks to reach more people and create sustainable opportunities for growth.
5. Connect business success with a larger purpose. Consider how your company's resources, experience, and relationships can support your community or help other entrepreneurs succeed. Incorporate mentorship, volunteering, or philanthropic initiatives into your long-term vision to create a legacy that extends beyond financial results.

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