The Unchecked-In Podcast

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

The Unchecked-In Podcast — Tue, 24 Mar 2026 11:02:41 -0400

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 it

Ben 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-16703b142

Company 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/bobbyhabanero

AI Hotel Revenue Management Software | TakeUp
TakeUp: https://takeup.ai/
LinkedIn: https://www.linkedin.com/company/takeup-ai/
Instagram: https://www.instagram.com/takeupforhospitality
Facebook: https://www.facebook.com/takeupforhospitality
YouTube: https://www.youtube.com/@TakeUp-for-hospitality

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

Bobby Marhamat — Tue, 03 Mar 2026 15:03:44 -0500

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 years
Why outdoor hospitality is outperforming traditional hotel models
The power of off-market hotel acquisitions
Why digital detox travel is becoming a health & wellness movement

Connect with Keir & Jonny:
Keir LinkedIn: https://www.linkedin.com/in/keir-weimer-a2a93145

Jonny LinkedIn: https://www.linkedin.com/in/jonny-jost-17ba1a204

Weekender Hotels: https://weekenderhotels.com/

Northbound Capital: https://northbound-capital.com/

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

Bobby Marhamat — Wed, 18 Feb 2026 06:00:00 -0500

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” system
The balance between automation, AI, and personalized guest experiences
Key operational processes that drive the biggest impact on staff and guest satisfaction
Lessons learned from mistakes early in Jacob’s career and how they shaped his leadership
The philosophy behind roadmap planning, prioritizing customer requests, and standardization
Insights on change management and making technology actually work for your team

Links:
Jacob on LinkedIn: https://www.linkedin.com/in/jacob-messina-b6361311

Company Website: https://www.stayntouch.com/

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

The Unchecked-In Podcast — Thu, 08 Jan 2026 22:00:00 -0500

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 baseline
Single-plate to menu-based breakfast transition for handling gluten-free, dairy-free, keto, vegetarian, and vegan simultaneously without separate prep
Daily contractor feeding program that converts vendor relationships into partnership discounts
Rate-setting approach that eliminates competitive comparison in favor of unique value positioning
Operating 35+ organic crop farm-to-table model without additional kitchen staff
Succession planning realities for aging owner-operators without exit buyers

Stellara's Meredith Garrett on Why Your Occupancy Problem Isn't a Pricing Problem

The Unchecked-In Podcast — Thu, 08 Jan 2026 21:00:00 -0500

Meredith Garrett operates Nashville party properties and remote Smoky Mountains resorts including 45-foot treehouses and glamping domes. She reveals why 8 units isn't enough to make remote hospitality profitable, the specific staffing math that changes at scale, and how to price experiences where no traditional comps exist, plus the misalignment between marketing and service delivery that most operators miss when occupancy drops.

From navigating spiral staircases with guest luggage to managing expectation gaps between luxury glamping and actual camping, Garrett shares the operational frameworks that determine when to deploy staff versus recalibrate guests remotely. She also breaks down her crowdfunding launch strategy that created founding members at permanent discount rates who now bring full-price friends, solving both launch revenue and repeat business simultaneously.

Topics Discussed:

Why 10-12 units is the minimum threshold for remote property profitability
Consecutive 12-hour on-site shifts versus dispatch-based staffing economics
Pricing unique properties through market learning when direct comps don't exist
The service delivery-ADR alignment framework for diagnosing booking problems
Deploying staff after-hours versus remote expectation recalibration decision matrix
Crowdfunding founding members at permanent discount rates who bring full-price guests
Builder inexperience costs on unique products requiring larger financial buffers
Operational complexity creating ADR floors regardless of occupancy pressure

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

The Unchecked-In Podcast — Thu, 08 Jan 2026 21:00:00 -0500

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 economics
Living two weeks in each unit before opening methodology
Social media documentation driving 3-4 daily booking inquiries pre-launch
1pm check-in, 8pm Sunday checkout solving weekend compression
Private plane charter integration for family reunion market
Virtual butler and treasure hunt platform launching 2027
Unplug challenge charging $25 for early phone retrieval
Five forward, three back operational acceptance philosophy

From Space Force Engineer to Boutique Hotel Owner: Jordan Malara’s Playbook for Buying Undervalued Inns and Building a Brand

The Unchecked-In Podcast — Mon, 08 Dec 2025 11:00:00 -0500

In today’s episode of Unchecked In, we sit down with Jordan Malara, owner of Springs Hospitality (Colorado), to unpack his transition from a U.S. Space Force engineer to boutique‑hotel operator—and the real estate and hospitality lessons he’s learning along the way.

Jordan shares how he left engineering and the military, started by investing in short‑term rentals, and eventually decided “if short‑term rentals are messy, hotels must do things better”—so he bought and operates boutique hotels. He explains why he chooses to buy existing hotel properties (rather than build new), how he identifies undervalued assets through location and demand, and how he uses key metrics (ADR, occupancy, RevPAR plus online reviews) to evaluate hotel viability. He also dives into the operational side: balancing renovations and guest experience, where to invest (communal spaces, human check‑in, wellness), how to build a meaningful hotel brand (why many independents fail), how to recruit talent by offering autonomy, and the hard realities many first‑time hotel investors underestimate (seasonality, cash‑flow, hidden cap‑ex).

Here’s what we’re diving into:

Jordan’s pivot from military engineer to hotel investor
Renovation strategy: balancing guest experience, budget, and operations
Investing in communal spaces, wellness, and human touch rather than just rooms
Why branding often fails for independents—and what to do differently
How he attracts and retains talent by giving them meaningful space and autonomy
Misconceptions about hotel investing: “It’ll just run itself” vs the reality of seasons, cap‑ex, operational complexity

Connect with Jordan Malara:

Connect with Unchecked In Podcast:

Website: The Unchecked‑In Podcast
Spotify: Listen on Spotify
Apple Podcasts: Listen on Apple Podcasts

7-Ranch's Joe Marzahl on How To Evaluate Rural Infrastructure Costs To Avoid Financial Surprises

The Unchecked-In Podcast — Tue, 26 Aug 2025 12:26:51 -0400

From corporate strategic marketing executive to glamping entrepreneur, Joe Marzahl reveals how he built 7-Ranch Getaways from 130 acres of raw Oklahoma land into a profitable hospitality operation generating repeat bookings and premium rates. His systematic approach to market positioning and infrastructure planning offers battle-tested frameworks for independent property operators competing against established vacation rental markets.

Joe's transition from steady corporate paychecks to entrepreneurial revenue optimization demonstrates how strategic planning methodologies transfer across industries. His wife's ultimatum—"if you don't try this, I'll be mad at you"—provided the support structure that enabled his leap from corporate comfort to building a destination experience in non-tourism Medill, Oklahoma, drawing guests from both Dallas-Fort Worth and Oklahoma City markets.

Topics discussed:

First-mover advantage execution: Joe's research-driven decision to deploy geodomes and mirror cabins instead of oversaturated tiny homes, securing Oklahoma's first-to-market position in unique accommodation categories that command premium pricing
Rural infrastructure cost modeling: The systematic evaluation process for water well capacity, electrical pole installation costs (thousands per pole), and rural water line proximity that determines project viability before land acquisition
Distributed operations model: Joe's once-weekly property visits combined with dedicated local turnover staff enable remote management across multiple units while maintaining guest experience standards
Influencer partnership optimization: Moving beyond follower count metrics to engagement rate analysis and audience demographic alignment, plus the revelation that identical follower counts can produce vastly different booking conversion rates
Strategic planning methodology transfer: How Joe's corporate experience in market trend analysis, competitive positioning, and financial modeling directly applies to hospitality property development and customer targeting
Expansion decision matrix: The evaluation framework Joe uses in his dual role as operator and rural real estate agent, assessing infrastructure requirements, staffing implications, and revenue thresholds for scaling beyond current three-unit capacity
Content marketing resource allocation: The transition from inconsistent owner-generated content to dedicated marketing hire with monthly budget allocation, addressing the operational challenge of maintaining social presence while running day-to-day operations

Woodmont Lodging’s Michael Blank on How To Integrate Service & Tech Without Losing Soul

The Unchecked-In Podcast — Tue, 15 Jul 2025 15:58:48 -0400

Michael Blank, Principal at Woodmont Lodging — with nearly 30 years across operations, consulting, investment banking, and a decade running his own investment firm — tackles the hospitality industry's most critical operational challenge: deploying technology to enhance profitability without sacrificing the human elements that drive guest loyalty. His portfolio experience reveals why most properties fail at tech integration and provides a tactical framework for implementing technology as operational leverage rather than service replacement.

Topics discussed:

Why the industry remains "woefully behind" in cohesive technology deployment, with most properties using piecemeal, one-off solutions instead of integrated systems that complement human touchpoints.
How delivering consistent basics combined with strategic human touchpoints that create memorable experiences guests will pay premium rates for.
A systematic approach to evaluating new hospitality technology, using properties as testing environments to measure impact on three critical metrics: profitability, customer service quality, and employee efficiency.
Why operators with big company experience often fail when buying from local sellers, requiring demand validation beyond basic market presence.
Pinpointing hidden capital requirements that branded property improvement plans miss, including HVAC systems, laundry equipment, and technology infrastructure.
Tactical implementation of gathering spaces that generate energy and repeat visits, such as a fireplace and wood design elements that create destination appeal within franchise constraints.
Identifying operational inefficiencies and revenue opportunities across multiple properties, moving beyond single-property optimization to institutional-level performance management that drives sustained profitability growth.

Black Bear Lodge’s Rachel Carlson on Year-Round Staffing in a Seasonal Market

TheUnchecked-InPodcast — Tue, 01 Jul 2025 11:52:21 -0400

Most independent property owners view seasonal markets as profit killers, but Owner Rachel Carlson has spent eight years proving the opposite at her 31-room Black Bear Lodge in Lake Tahoe. Her counterintuitive approach to staffing, community integration, and guest experience design demonstrates how owner-operators can leverage their personal involvement into sustainable competitive advantages. In this inaugural episode of The Unchecked-In Podcast, Rachels gives host Bobby Marhamat, CEO of TakeUp, specific strategies for transforming seasonal challenges into profit drivers while maintaining authentic hospitality experiences that generate consistent repeat bookings.

Rachel's analysis of how wedding operations prevent optimal daily room utilization provides crucial insights for property owners evaluating event strategies versus traditional hospitality models. Likewise, her "no ego amigo" philosophy emphasizes collaboration with local competitors and industry partners rather than isolated business approaches. Rachel's approach to community integration through wine tastings, local art partnerships, and neighborhood events demonstrates how independent properties can create authentic connections that franchise operations cannot replicate.

Topics Discussed:

The strategic decision to maintain year-round staffing in seasonal markets rather than cutting labor costs, minimizing turnover and ensuring property maintenance.
Why wedding venue operations fundamentally conflict with optimal hotel room utilization patterns and the revenue implications of booking entire properties for single-day events.
Community integration strategies that transform local neighbors into brand ambassadors through wine tastings, art gallery partnerships, and authentic local engagement rather than tourist-focused approaches.
The "no ego amigo" philosophy for independent property owners entering hospitality without traditional hotel backgrounds, emphasizing collaboration with local competitors and industry mentors.
Unique room design methodology that eliminates standardization in favor of personalized touches, different artwork, and distinct furniture selections that create guest loyalty and specific room requests.
Sustainability initiatives that simultaneously reduce operational costs through strategic amenity elimination and California rebate programs for energy-efficient equipment upgrades.
The competitive advantages independent properties possess over vacation rentals through personal staff interactions, local recommendations, and authentic hospitality experiences that justify premium pricing.
Destination market success strategies that require owner presence and hands-on involvement rather than remote management approaches, balancing personal lifestyle with business operations.
Converting first-time guests into repeat visitors through personalized staff interactions, local expertise sharing, and memorable experiences that differentiate independent properties from franchise operations.