About Me
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Samantha Bentson, Founder
Entrepreneur. Operator. Now Your Operations Partner.
After spending more than 20 years building and leading my own companies, I now work alongside business owners to help them grow stronger, more efficient organizations.
Experience That Elevates
Samantha Bentson is an entrepreneur, operator, and business strategist with more than two decades of experience building and scaling successful companies. As the founder of Elevate, she now partners with small businesses to strengthen operations, improve efficiency, and help leadership teams turn big goals into practical execution.
Samantha previously served as the Chief Executive Officer of Cashland Holdings, LLC and Borrow Money Now, companies she led for over 20 years after taking over operations from her father, who founded the business in 1987. Under her leadership, the company experienced significant growth, expanding to ten retail locations across Oklahoma and evolving its financial products from traditional payday lending to a revolving line of credit model—an approach she helped pioneer in the industry.
Recognizing the shift toward digital services, Samantha launched the company’s online lending platform in 2010, now known as Borrow Money Now. The online division gained strong momentum beginning in 2013 and grew into a significant part of the company’s operations, with Samantha remaining closely involved in day-to-day management, including overseeing call center operations and customer experience.
In 2025, Samantha successfully sold the business to a larger multi-state operator. Following the sale, she launched Elevate to share the operational insight, strategic thinking, and hands-on leadership experience she gained from building and scaling her own companies.
Samantha remains deeply committed to entrepreneurship and the small business community. She is an active member of the Entrepreneurs' Organization (EO), a global network of nearly 20,000 business owners in more than 60 countries. Within the Entrepreneurs' Organization Oklahoma City chapter, she currently serves as President and Membership Chair.
Samantha is a graduate of the University of Oklahoma, where she earned a Bachelor of Arts in Journalism with a minor in Communications, and later completed her MBA at Southern Nazarene University.
A lifelong Oklahoma City resident, Samantha is passionate about helping entrepreneurs grow sustainable businesses while maintaining strong operational foundations. Through Elevate, she brings both strategic perspective and real-world execution to the businesses she serves.