About
Habits for Winning
Our Team
Meet Our Hosts
Leighton Cubbage
Founding Partner
Chief Executive Officer
Leighton Cubbage is an entrepreneur, investor, and business leader based in the Greenville, South Carolina area. He is best known for founding and leading telecommunications, banking, and real-estate ventures, as well as for his involvement in civic, healthcare, and entrepreneurial organizations.
Early Life and Education
Grew up in Sumter.
Played football at Clemson University before pursuing business opportunities.
Later completed the Advanced Management Program at the University of North Carolina at Chapel Hill.
Business Career
Cubbage’s entrepreneurial career began in telecommunications. He founded or co-founded several communications companies, including:
Corporate Telemanagement Group
TelMan Communications
Serrus Telecom Investments
He later expanded into banking and real estate, becoming a founding figure in:
Southern First Bank
Serrus Capital Partners
Allie Capital, where he serves as Chairman.
Leadership and Public Service
Beyond business, Cubbage has held leadership positions with numerous organizations, including:
Greenville Health System (served two terms as chairman)
South Carolina Venture Capital Authority (chairman)
Greenville Chamber of Commerce
Greenville Technical College Foundation
Homes of Hope
Southern First Bancshares (director)
Recognition
His achievements have earned him honors such as:
South Carolina Entrepreneur of the Year
Inclusion in the Clemson entrepreneurial hall of fame
Boy Scouts regional Man of the Year recognition
Various civic and business leadership awards.
Philosophy
In speeches to entrepreneurs, Cubbage has emphasized lifelong learning, integrity, goal setting, solving real customer needs, and surrounding oneself with talented people. He has often described success not simply as financial achievement but as creating significance and helping others succeed.
Overall, Leighton Cubbage is regarded as one of Greenville’s prominent entrepreneurs, having built companies across telecommunications, banking, and real estate while maintaining a strong presence in community and economic-development leadership.
Dan Sterling
Founding Partner
Chief Sales Officer
Dan Sterling is a technology entrepreneur, growth strategist, and executive leader with more than 30 years of experience building high-performing sales organizations and scaling companies across the telecommunications, cloud, AI, and technology industries.
Throughout his career, Dan has led national sales teams, developed world-class channel partner ecosystems, and helped organizations accelerate revenue growth through strategic leadership, operational excellence, and customer-focused innovation. He has held executive leadership positions with some of the industry's most respected organizations, including Green Cloud Technologies, ScanSource/Intelisys, NuVox Communications, and Windstream, where he played a key role in expanding market share and driving significant business growth.
Today, Dan is the Co-Founder of Rhino Digital Solutions, where he is helping entrepreneurs leverage artificial intelligence, automation, CRM technology, digital marketing, and proven sales systems to grow faster while simplifying operations. His mission is to make enterprise-level technology practical and affordable for small and midsize businesses.
A passionate entrepreneur and mentor, Dan believes business success begins with leadership, discipline, faith, and daily habits. He is also the Co-Founder of the Habits for Winning podcast, where he interviews accomplished entrepreneurs, executives, athletes, and business leaders to uncover the principles, mindset, and habits behind sustained success.
Known for his energetic leadership style, competitive spirit, and ability to build winning cultures, Dan has earned a reputation for developing exceptional teams, mentoring future leaders, and helping organizations navigate periods of rapid growth and transformation.
Dan attended Christ Church Episcopal School in Greenville, South Carolina, and the University of South Carolina. He remains active in mentoring entrepreneurs (United Way Mentor of the Year) and business leaders while continuing to build companies that create lasting value for customers, employees, and communities.
Jeff Baker
Founding Partner
Chief Marketing & Technology Officer
Jeff Baker is a high-energy, intuitive leader whose rare combination of deep technical expertise and sharp business acumen sets him apart. Having partnered with global organizations to orchestrate multinational teams and drive measurable bottom-line results, Jeff brings an entrepreneurial mindset and genuine passion for emerging technologies to every challenge. His ability to translate complex innovation into practical, results-driven strategies makes him uniquely equipped to help businesses navigate today’s rapidly evolving digital landscape.
As co-founder, CMO & CTO of Rhino Digital Solutions, Jeff plays a central role in revolutionizing digital marketing for small and medium-sized businesses across the United States and around the world. The agency is built around GoHighLevel as its core SaaS platform while delivering meaningful added value through strategic services designed to accelerate growth. Jeff’s leadership ensures that every client engagement goes far beyond software — combining technology with high-touch strategy, creative execution, and ongoing optimization.
Jeff is also Co-Founder of the Habits for Winning podcast, a platform built for entrepreneurs by real-life entrepreneurs. Through the podcast, Jeff helps bring forward the stories, disciplines, setbacks, and winning habits of leaders who have built something real — not theory from the sidelines, but lessons earned in the arena.
Jeff is the driving force behind Rhino Digital Solutions’ signature offerings, including The Marketing Intensive (up to three hours of focused planning sessions that produce a detailed 12-month roadmap) and the comprehensive Digital Marketing Roadmap that dives deep into brand messaging, web technology, content strategy, reputation management, social media, meaningful metrics, and search engine marketing. He also oversees the agency’s state-of-the-art digital studio, delivering high-quality video content that strengthens brands, and is actively expanding custom AI solutions and cloud computing capabilities to give clients a true competitive edge. Through these initiatives and the flexible Annual Maintenance Program, Jeff helps ambitious businesses achieve unstoppable, sustainable growth.
We’re dedicated to providing insightful, engaging, and entertaining podcasts that connect you with real stories from entrepreneurs.
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