Lost In The Midlands

In this episode, we sit down with Bill Douglas to hear how his roots in retail grocery shaped his work ethic, leadership style, and people-first approach. Bill shares how those early lessons carried him through his professional career and ultimately led him to his role at Seawright Roofing. From stocking shelves to leading in a new industry, his story is a testament to adaptability, hard work, and the surprising ways our paths prepare us for what’s ahead.#LeadershipJourney #CareerGrowth #BillDouglas #SeawrightRoofing #BusinessLeadership #CareerPath #Adaptability #ColumbiaSC

Courtney Boomer built Scale Up with Courtney, a Columbia, SC–based agency that helps service businesses automate, streamline, and scale—with clarity and heart. After a background in corporate analytics and virtual assistance, she leaned into systems, CRMs, and marketing strategy. Today, she builds automation, CRM workflows, and tech support for service-based entrepreneurs—while homeschooling four young kids.In this episode of Lost in the Midlands, Wright Brennan and Courtney dive into how systems can eliminate chaos, why boundaries matter, and how scaling doesn’t have to equal burnout.Lost in the Midlands tells real stories from entrepreneurs shaping the Midlands—with strategy, grit, and community.Learn more at ScaleUpWithCourtney.com Subscribe for more stories from Midlands business owners Listen wherever you get podcasts

We sat down with Holly Sanson from Seawright Roofing about the real challenges she’s faced in the roofing industry and how she pushed through them. Holly opens up about the lessons she’s learned, the wins along the way, and how her leadership has helped shape the future of Seawright Roofing. Learn more about Seawright RoofingListen wherever you get your podcasts Subscribe for more conversations with Midlands entrepreneurs

Behind the chair, she built a salon focused on lived‑in color, extensions, bridal services, and client care. Known for mentoring and growing her team, Rachel is rooted in community and quality. Lost in the Midlands is a show about the business owners and entrepreneurs who bring Columbia to life—real stories from right here in the Midlands. Learn more about The Velvet Edge Salon Listen wherever you get your podcasts Subscribe for more conversations with Midlands entrepreneurs

Randy Freeman runs Midlands Dumpster Service—one of the most recognized dumpster rental companies in Columbia, SC. He shares how he grew the business, what it’s like working with contractors and homeowners, and why customer service has always been at the center of it all. You’ll also hear how he got involved in local business networks like BNI and what it takes to keep a service-based business running in a fast-moving market like the Midlands. Lost in the Midlands is a show about the business owners and entrepreneurs who make Columbia, SC what it is. Each episode features a local story worth knowing. Learn more at midumps.com Listen wherever you get your podcasts Subscribe for more conversations with local business owners