In this episode of Beyond Barriers, Charles Smith, an extraordinary leader, shares his inspiring journey from delivering mail to directing boardrooms. With grit, determination, and an unwavering commitment to equity, Charles recounts his rise from humble beginnings on Chicago’s west side to becoming the CEO and Founder of CS Insurance Strategies, a thriving national insurance brokerage.
Charles opens up about his childhood on Chicago’s west side, where he learned the power of community, love, and grit. He reveals how his ability to cultivate relationships, align values, and embrace resilience propelled him forward—even when others doubted his potential. As a champion for minority-owned businesses and equity-driven leadership, Charles highlights how businesses can thrive by fostering inclusive and transparent practices.
This episode will inspire you to take charge of your career, find strength in challenges, and create lasting change in your community and beyond.
Key Takeaways:
- Resilience in Action: Discover how determination can turn obstacles into stepping stones.
- The Value of Relationships: Learn how cultivating genuine connections opens doors and drives success.
- Inclusive Leadership: Explore the importance of equity and community-driven growth in leadership.
- Seizing Opportunities: Uncover practical ways to prepare yourself for success, no matter your starting point.
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Highlights
The key moments in this episode are:
[00:00] Introduction to Beyond Barriers Podcast
[00:27] The Power of Patience
[01:23] Charles Smith's Journey Begins
[03:43] Early Life and Influences
[06:05] Navigating Challenges and Building Relationships
[11:00] From Mailroom to CEO
[15:28] The Importance of Mentorship
[19:30] Balancing Multiple Roles and Reflection
[27:50] Reflecting on Teenage Parenthood
[30:27] Setting and Achieving Goals
[34:17] Navigating Relationships and Mentorship
[38:09] Challenges and Opportunities in Business
[41:07] Lightning Round and Final Thoughts -
Lightning Round
Q: What book has greatly influenced you?
A: Boss: Richard J. Daley of Chicago by Mike RoykoQ: What is your favorite inspiring quote or saying?
A: Patience is a virtueQ: What is one word or moniker you would use to describe yourself?
A: ResilienceQ: What is one change you've implemented that made your life better?
A: Working OutQ: What power song would you want playing as you walk out onto a stage?
A: Lucky - EverygreenQ: What do you want your legacy to be?
A: I want my legacy to be the creation of a circular economy that empowers Black businesses, fosters growth, and connects small enterprises with large corporations to drive community investment and job creation. -
Quotes
What I found out over time is that it didn't matter how successful the company was. It didn't matter what customer service did, what the sales guys did, or the CEO, if brokers who are our clients didn't get their checks, which was my responsibility, nobody would be happy. Because of that, I've always seen value in every single role in the company, and that's how I built my company.
Charles E. Smith
I am a true believer that what is for me is for me. If I don't get something, it is because it's not for me, it's not because I failed, it's not because I'm not good at this or that, it literally means that there's something else better waiting for me.
Charles E. Smith
You can’t say no to an opportunity if you don't know the details.
Charles E. Smith
I learned early on that success and fear go hand in hand. Pushing myself to do uncomfortable things, even when I felt nervous, often led to outcomes that boosted my confidence and sense of self-worth.
Charles E. Smith
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About
Charles E. Smith is Founder and CEO of C.S. Insurance Strategies (CSIS), a commercial insurance brokerage providing employee health and benefits, business insurance and risk management consulting across the United States. CSIS serves clients of all sizes in every industry with specialized expertise in municipal, non-profit, and minority-owned businesses. Charles, who started his career in the CNA Insurance mail room, has more than three decades of experience in health care and insurance--experience garnered through high performance roles in several other national insurance companies.
"I am passionate about advocating for progress through the demonstrated values of equity and inclusion. I place high priority on good corporate citizenship and I am dedicated to making a positive impact in all our communities."
Deep commitments to success and social responsibility are the driving forces for Charles who believes that CSIS should not and cannot exist without both. He invests his time, energy and financial resources in building his company while supporting other minority-owned businesses and community-development efforts.
Civic Engagement and Recognition:
Charles is Vice Chairman of World Business Chicago and a member of the Executive Club of Chicago, The Economic Club of Chicago, The Chicago Club, The Shedd Aquarium Board of Trustees, and the President's Advisory Board of the Museum of Science and Industry. Charles also is Executive Commitee Chairman of the Business Leadership Council, the area's premier association of Black business leaders and entrepreneurs.