The challenges, successes, and lessons learned operating and growing small and medium-sized businesses.

In this episode, Jamie Cusack, CEO of Keystone Access Partners, Shore Capital’s entrance and access control platform built on Dillard Companies and The Ritchie Group, shares how he came to the CEO seat by watching the Shore model work from the inside as a board member of another Shore company before betting his own career on it. He walks through what a growth-based partnership looks like from the founder’s side of the table: the open conversation about what each owner wants next, the leadership training his teams had never had access to before, and the promise that a process that works in the field is something to learn from rather than replace. Jamie also takes on the biggest assumption he hears in the market, that owners running on spreadsheets or pen and paper aren’t ready to sell, and explains why most are more ready than they think. Finally, he is direct about what Keystone looks for in a partner and why a good business isn’t enough: the people have to be good too.

In this episode, Josh Allen, founder of Companion Baking in St. Louis, Missouri, shares how he turned a love of baking discovered in the Bay Area into a frozen artisan bread manufacturer shipping custom products across all 48 contiguous states. Guided by his grandfather’s advice to listen to his customers, Josh built the business one customer and one product at a time, pivoted from wholesale to frozen manufacturing, and made helping customers tell their stories through bread the heart of what Companion does. He also reflects on why he always took the private equity calls out of curiosity, what made Shore different, and why partnering now rather than later lets him stay part of the journey as Companion builds its platform.

In this episode, Keith Caldwell, CEO of H2O Care Partners, and Sarah Longstreet, the company’s Chief Marketing Officer, share the story of building a national water treatment platform. It began in 2021 when Keith met Mark St. Hilaire, founder of H2O Care in Massachusetts, and saw an opportunity to combine doing good with the growth potential of a fragmented, family-run industry. Today the platform spans more than thirty brands across nearly twenty states, supported by a Boston-based resource team of over forty across marketing, finance, hiring, technology, and operations. Keith and Sarah reflect on the network effect that emerges when great local businesses come together, how each new partner brings superpowers that get shared across the platform, and why preserving local brands, community ties, and long-tenured teams is central to how they scale. They also discuss what makes the right partner, from founders approaching retirement to those just getting started, and what’s next as the platform continues to grow.

In this episode, Joe Rice, CEO of CXponent, shares how watching his father run a business sparked a lifelong pull toward entrepreneurship and building something of his own. He describes how CXponent cuts through the overwhelming noise of technology vendors and AI tools to help mid-market companies make better decisions, and why trust, not technology, remains the foundation of every client relationship. Joe reflects on his first company, what he learned from that exit, and what drew him back to build again. He talks candidly about what founders should weigh before joining a platform, the importance of readiness and timing, and why Shore’s focus on stacking talent and investing in organic growth made it the right fit. Throughout the conversation, Joe makes clear that even in a market being reshaped by AI, the work still comes down to people, presence, and being a partner clients can count on.

In this episode, Ryan Burke reflects on his journey from selling roofs in Colorado Springs to founding Bulldog Roofing at 23 and partnering with Shore Capital to help build Skycrest Roof. He shares how frustration with bad actors in the industry and a belief that customers and employees deserved better pushed him to take the leap and start the business out of his living room. Ryan discusses the rapid growth that followed, the chaos that came with it, and the hard lessons of moving from hustle to structure as the business scaled to sixty people and $30M in revenue. He talks candidly about his initial fears around private equity, why protecting his team of family and friends was his top priority, and how meeting the people at Shore shifted his perspective on partnership. Ryan highlights the importance of readiness, the value of building real processes and resilience into a business, and what Skycrest is looking for in the next generation of founders as it continues to grow.

In this episode, Ben Hayes, Nick Baxter, and Austin Bockwinkel share how Freestone Insurance Group is building a nationally recognized insurance platform rooted in relationships and entrepreneurial drive. Ben reflects on his journey from professional golf to founding a full-service brokerage, and how an unplanned conversation with Shore Capital opened his eyes to what Freestone could become. The team discusses why they chose partnership over exit, how investing in talent and technology transformed their business, and what they look for in agency owners ready to join the platform. They talk about preserving the brands and cultures entrepreneurs have built, why the most exciting time to join is at the beginning, and how insurance remains a people-first industry where Freestone’s future will be defined by the partners who choose to be part of the story.