Paper Trails

Getting ready for the busy tourist season

This week on Small Business Big World: Getting ready for the busy tourist season – An interview with Mark Osborn

This is Small Business Big World, our weekly podcast prepared by the team at Paper Trails. Owning and running a small business is hard. Each week we’ll dive into the challenges, headaches, trends, fun and excitement of running a small business. After all, small businesses are the heartbeat of America and our team is here to keep them beating.

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Understanding seasonal hospitality management

Seasonal hospitality, like managing an inn, requires careful coordination of various elements—from staffing to property upgrades. In this week’s episode of Small Business Big World, we look at how Mark Osborn from the Topside Inn in Boothbay Harbor, Maine effectively prepares for the busy season to ensure smooth operations.

Preparing for the peak season

Key to getting ready for the busy season is the strategic offseason preparation. Mark Osborne highlights the importance of assembling a dedicated team and planning property enhancements when guest flow is low. This approach allows for addressing local market dynamics and setting the stage for high season demands. Training a cohesive team is crucial, as it enhances guest service and operational efficiency.  A key takeaway is that Mark leverages his current staff to bring friends and family members to the Topside Inn for work.  This allows his staff to grow, while knowing that his great employees will be bringing other great employees to join the team.

Local engagement and guest experience

At Topside Inn, the emphasis is on creating a memorable local experience. Osborn focuses on sourcing local cheeses and collaborating with area vendors, enhancing the authenticity of the guest experience. Regularly introducing new items each season keeps the offerings exciting and relevant, which is recognized in positive guest reviews and accolades like those from TripAdvisor.

Effective marketing and community connections

Effective marketing is essential when getting ready for the busy season.  Mark’s strategy involves understanding guest behaviors and engaging with the local community. This dual approach not only attracts guests but also creates deeper connections with the area’s culture and offerings, making the inn a more attractive choice for travelers seeking genuine local experiences.

Managing renovations to enhance guest comfort

Maintaining and upgrading the property is vital for keeping it competitive and appealing. Osborn takes a careful approach to renovations, ensuring that improvements like adding a luxury bar are done without disrupting guest comfort. These updates are not only about aesthetics but also about adding value to the guest experience, making the inn a preferred choice for travelers.

Conclusion: lessons from seasonal hospitality management

This discussion with Mark Osborn sheds light on effective strategies for managing a seasonal hospitality business. The focus on team preparation, local collaboration, strategic marketing, and thoughtful property enhancements are all crucial for success. For anyone involved in or interested in seasonal hospitality, these insights offer practical guidance on how to excel in managing an inn or similar business. Join us in learning from the experiences at Topside Inn, where seasonal preparation meets operational excellence.

This podcast is a production of Paper Trails. We are a payroll and HR company based in Kennebunk, Maine, and we serve small and mid-sized businesses across New England and the country. If you found this podcast helpful, don’t forget to follow us at at Paper Trails Payroll across all social media platforms and check us out at for more information. As a reminder, the views, opinions and thoughts expressed by the hosts and guests alone. The material presented in this podcast is for general information purposes only and should not be considered legal or financial advice. By inviting this guest to our podcast, Paper Trails does not imply endorsement of or opposition to any specific individual, organization, product or service.