The Unchecked-In Podcast

15 Years of Hotel Turnarounds: What Actually Works vs. What Doesn't | with Benjamin Gray

How do you turn struggling hotels into market leaders?In this episode, Bobby Marhamat sits down with Benjamin Gray, co-founder of Henlopen Hospitality and a seasoned hotel operator with more than 15 years of experience transforming underperforming properties into thriving businesses. Recognized as the AHLA National General Manager of the Year and featured in outlets like The Wall Street Journal and CNBC, Ben shares the real operational strategies behind successful hospitality businesses.Ben’s journey into hospitality started unexpectedly—after leaving law school and landing a part-time night audit job at a Hampton Inn. Just eight months later, he became a General Manager, launching a career built on leadership, culture, and operational excellence.In this conversation, Ben breaks down what actually drives hotel performance—from aligning ownership vision with frontline teams to identifying overlooked revenue opportunities that can dramatically improve profitability.In this episode, you’ll learn: How Ben went from front desk to General Manager in 8 months The biggest leadership mistakes hotel operators make  Why people and culture matter more than systems alone  Simple operational tweaks that can add major revenue The importance of aligning ownership vision with the teams executing itBen also shares unforgettable stories from the field—including the realities of hotel operations, lessons learned from early career mistakes, and why every GM should keep a “go bag.”Connect with Benjamin Gray: Benjamin on LinkedIn: https://www.linkedin.com/in/benjamin-gray-16703b142Company website: https://henlopenhospitality.com/Connect with Bobby Marhamat:Website: https://bobbymarhamat.com/Facebook: https://www.facebook.com/bobbymarhamat/LinkedIn: https://www.linkedin.com/in/bobbymarhamat/Instagram: https://www.instagram.com/bobbyhabaneroAI Hotel Revenue Management Software | TakeUpTakeUp: https://takeup.ai/LinkedIn: https://www.linkedin.com/company/takeup-ai/Instagram: https://www.instagram.com/takeupforhospitalityFacebook: https://www.facebook.com/takeupforhospitalityYouTube: https://www.youtube.com/@TakeUp-for-hospitality

Building A Hotel Brand for Outdoor Leisure Markets | with Keir Weimer & Jonny Jost of Weekender Hotels

What does it take to build a fast-growing independent hotel brand in today’s market?In this episode of The Unchecked-In Podcast, Bobby Marhamat sits down with Keir Weimer, CEO of Northbound Capital and Founder of Weekender Hotels, and Jonny Jost, Director of Growth and Investor at Northbound Capital.From growing up in the 6-million-acre Adirondack Park to scaling an 11-property outdoor hospitality portfolio in just five years, Keir and Jonny break down what it really takes to build, renovate, and scale independent hotels in outdoor leisure markets.Here’s what you’ll learn:How Weekender scaled from 1 to 11 hotels in 5 yearsWhy outdoor hospitality is outperforming traditional hotel modelsThe power of off-market hotel acquisitionsWhy digital detox travel is becoming a health & wellness movementConnect with Keir & Jonny:Keir LinkedIn: https://www.linkedin.com/in/keir-weimer-a2a93145Jonny LinkedIn: https://www.linkedin.com/in/jonny-jost-17ba1a204Weekender Hotels: https://weekenderhotels.com/Northbound Capital: https://northbound-capital.com/Connect with Bobby Marhamat:Website: https://bobbymarhamat.com/Facebook: https://www.facebook.com/bobbymarhamat/LinkedIn: https://www.linkedin.com/in/bobbymarhamat/Instagram: https://www.instagram.com/bobbyhabaneroAI Hotel Revenue Management Software | TakeUpTakeUp: https://takeup.ai/LinkedIn: https://www.linkedin.com/company/takeup-ai/Instagram: https://www.instagram.com/takeupforhospitalityFacebook: https://www.facebook.com/takeupforhospitalityYouTube: https://www.youtube.com/@TakeUp-for-hospitality

Overcoming Challenges in Hotel Tech Adoption | with Jacob Messina, CEO of Stayntouch

In this episode of The Unchecked-In Podcast, Bobby Marhamat sits down with Jacob Messina, CEO of Stayntouch, a cloud-native PMS helping hotels streamline operations and deliver exceptional guest experiences.Jacob shares insights from his journey across hospitality—from working in restaurants as a teen, to leading operations at Lowe’s Hotels and MCR Hotels, to now driving innovation in hotel technology. He dives into the real challenges hotel operators face with tech adoption, why independent hotels often outperform big brands in flexibility and guest experience, and how AI and automation can enhance—but not replace—the human touch in hospitality.What you’ll learn in this episode:How to approach hotel technology without fear of choosing the “wrong” systemThe balance between automation, AI, and personalized guest experiencesKey operational processes that drive the biggest impact on staff and guest satisfactionLessons learned from mistakes early in Jacob’s career and how they shaped his leadershipThe philosophy behind roadmap planning, prioritizing customer requests, and standardizationInsights on change management and making technology actually work for your teamLinks:Jacob on LinkedIn: https://www.linkedin.com/in/jacob-messina-b6361311Company Website: https://www.stayntouch.com/Connect with Bobby Marhamat:Website: https://bobbymarhamat.com/ Facebook: https://www.facebook.com/bobbymarhamat/LinkedIn: https://www.linkedin.com/in/bobbymarhamat/Instagram: https://www.instagram.com/bobbyhabaneroAI Hotel Revenue Management Software | TakeUpTakeUp: https://takeup.ai/LinkedIn: https://www.linkedin.com/company/takeup-ai/Instagram: https://www.instagram.com/takeupforhospitalityFacebook: https://www.facebook.com/takeupforhospitality YouTube: https://www.youtube.com/@TakeUp-for-hospitality

Speckled Hen Inn's Heather Shannon on Why Creating a Niche Beats Competing on Features

Heather Shannon runs Speckled Hen Inn with a pricing strategy that contradicts what most revenue management systems recommend: she ignores competitor rates completely. After nine years of building a working farm operation with 35+ organic crops integrated into daily service, her approach centers on creating experiences competitors can't replicate—guests return years later naming the specific lambs they bottle-fed, not comparing room rates.Her operational framework came from expensive failures. An emergency renovation during peak season cost 45 days of revenue and nearly broke the business, leading to a specific capital reserve formula she now considers non-negotiable. Year three brought an operational crisis when dietary restrictions exploded—handling five simultaneous special diets for 10-12 guests at one table forced a complete service model redesign from traditional single-plate breakfast to menu-based operations. The contractor relationships that saved the business during the renovation crisis were built through a simple daily feeding program that converted transactional vendors into long-term partners offering emergency discounts.Topics discussed:Capital reserve calculation using 30 days of highest room rate revenue as emergency fund baselineSingle-plate to menu-based breakfast transition for handling gluten-free, dairy-free, keto, vegetarian, and vegan simultaneously without separate prepDaily contractor feeding program that converts vendor relationships into partnership discountsRate-setting approach that eliminates competitive comparison in favor of unique value positioningOperating 35+ organic crop farm-to-table model without additional kitchen staffSuccession planning realities for aging owner-operators without exit buyers

Black Pearl Cove's Nicole Casino on 5 Steps Forward, 3 Steps Back: The Operational Reality of Luxury Glamping

Nicole Casino built a hospitality brand generating 3-4 daily booking inquiries without paid marketing by documenting her three-year journey from RV glamping influencer to island resort owner on social media.Her Black Pearl Cove property in Georgia challenges industry norms with 1pm Friday check-ins and optional 8pm Sunday checkouts, addressing the fundamental flaw that most vacationers spend more on transportation than accommodations.After discovering glamping operators were replacing moldy canvas four times yearly while maintaining full occupancy at premium prices, Nicole spent four years at glamping conventions researching structures that could deliver Ritz Carlton-level experiences in nature without the maintenance burden.Topics discussed:Canvas tent replacement four times yearly revealing unit economicsLiving two weeks in each unit before opening methodologySocial media documentation driving 3-4 daily booking inquiries pre-launch1pm check-in, 8pm Sunday checkout solving weekend compressionPrivate plane charter integration for family reunion marketVirtual butler and treasure hunt platform launching 2027Unplug challenge charging $25 for early phone retrievalFive forward, three back operational acceptance philosophy