Masters of Moments

By Jake WurzakSociety & Culture Business Investing Places & Travel

Masters of Moments episodes

February 25How to Develop Profitable Boutique Hotels - Ethan Orley - Managing Partner at Oliver Hospitality
In this episode of Masters of Moments, Jake Wurzak sits down with Ethan Orley to unpack his unconventional path into boutique hotel development and management. What started as a post-GFC leap of faith on a 28-room hotel in Knoxville evolved into a design-driven hospitality platform focused on secondary and tertiary markets. Ethan shares how creativity, operational intensity, and disciplined real estate underwriting intersect in his approach to building distinctive properties that stand out without overextending on risk.
From bootstrapping a speakeasy with six frat guys and free beer to navigating brand partnerships, third-party management, and the realities of food and beverage, Ethan offers a candid look at what it really takes to create and operate memorable hotels. He reflects on design storytelling, the importance of basis and incentives, and why sometimes the best opportunities are found off the radar.
They discuss:
How Ethan went from distressed debt and apartments to boutique hotels in secondary markets

The role of design narrative and storytelling in creating differentiated hospitality experiences

Why basis, incentives, and downside protection matter more than chasing hot markets

Lessons learned from building and operating in-house management versus using third parties

The hard truths of hotel food and beverage and what separates a struggling outlet from a profitable one
Connect & Invest with Jake:
Follow Jake on X: ⁠https://x.com/JWurzak⁠
1 on 1 coaching with Jake: ⁠https://www.jakewurzak.com/coaching⁠
Learn How to Invest with DoveHill: ⁠https://bit.ly/3yg8Pwo⁠
Links:
Oliver Hospitality - https://www.oliverhospitality.com/
Ethan on LinkedIn - https://www.linkedin.com/in/ethanorley/
Topics:
(00:00:00) - Intro
(00:0:22) - Why hotels: operations, design passion, and real estate upside
(00:06:02) - Winning in secondary & tertiary markets
(00:12:54) - Betting on ‘mixed’ markets
(00:16:44) - Indie vs. branded hotels
(00:27:20) - Finding deals without a fund
(00:32:17) - Design & storytelling
(00:36:03) - Crafting the hotel’s storyline
(00:42:03) - When to use third-party management
(00:48:50) - Outsourcing accounting & SOPs
(00:52:40) - Food & beverage reality check
(01:02:05) - Non-negotiables in new builds
(01:07:13) - Favorite hospitality experience
1 hr 10 min
February 04How Omni Aligns Real Estate, Operations, and Guest Experience - Kurt Alexander - President of Omni Hotels & Resorts
In this episode of Masters of Moments, Jake Wurzak sits down with Kurt Alexander to unpack how Omni Hotels has built a differentiated hospitality platform by staying deeply rooted in ownership, operations, and long-term thinking. Kurt shares his unconventional path from accounting and investment banking into hotel operations, including the formative experience of working every frontline role at Omni early in his career. The conversation explores why hospitality is fundamentally about people, how ownership mindset shapes better decision making, and what it takes to build hotels that feel both authentic to their destination and durable over decades.
They discuss:
Kurt’s transition from finance into hospitality and the lessons learned from working in frontline hotel roles

Why Omni’s owner-operator model drives better operational, design, and capital allocation decisions

How in-house design, construction, and food and beverage teams create differentiated guest experiences

The role of programming, amenities, and experiences in winning group, leisure, and business travel

What Omni has learned from joint venture partnerships, challenging deals, and long-term capital stewardship
Links:
Kurt on LinkedIn - https://www.linkedin.com/in/wkurtalexander/
Omni Hotels & Resorts - https://www.omnihotels.com/
Connect & Invest with Jake:
Follow Jake on X: ⁠https://x.com/JWurzak⁠
1 on 1 coaching with Jake: ⁠https://www.jakewurzak.com/coaching⁠
Learn How to Invest with DoveHill: ⁠https://bit.ly/3yg8Pwo⁠
Topics:
(00:00:00) - Intro
(00:02:48) - From finance to frontline
(00:05:37) - The calling of hospitality
(00:09:49) - Omni's unique ownership model
(00:17:07) - Design and construction innovations
(00:27:18) - Programming for group and leisure travelers
(00:34:08) - Competing in the hospitality industry
(00:37:25) - Omni's brand identity and signature experiences
(00:39:12) - Independent positioning of Omni Hotels
(00:39:48) - Leveraging loyalty and unique experiences
(00:41:04) - In-house culinary expertise and challenges
(00:43:45) - Balancing culinary innovation and simplicity
(00:45:46) - Adapting to market demands in f&b
(00:52:06) - Creating a culture of ownership and excellence
(00:55:52) - Incentivizing leadership and sales teams
(00:58:33) - Omni's business model and financial strategy
(01:02:15) - Lessons from jv partnerships
(01:05:01) - Navigating challenges and learning from mistakes
(01:07:31) - The importance of long-term thinking in hotel investments
(01:09:37) - Favorite hotels and closing remarks
1 hr 12 min
January 07Wrapping up 2025: Wins, Losses, and Predictions for The Hospitality Industry
In this solo year end episode of Masters of Moments, Jake Wurzak reflects on the highs, lows, and hard lessons from 2025 across his hospitality portfolio and broader business journey. He walks through recent acquisitions, operational wins, and exits, while candidly unpacking mistakes around debt timing, goal setting, and team management. Jake also shares how shifting guest preferences, declining RevPAR, and rising costs are reshaping the hotel industry, and why experiential and luxury assets continue to outperform. The episode closes with a forward looking view on 2026 and what has him re energized about hospitality.
He discusses:
Key wins from 2025 including the White Barn Inn acquisition, early distributions, and high ROI operational improvements

Lessons learned from debt maturities, refinancing risk, and how market timing can dictate outcomes

Mistakes around goal setting, performance measurement, and acting too slowly on underperformance

Why experiential and luxury hotels are outperforming amid declining RevPAR in other segments

How changing guest behavior, supply constraints, and brand dynamics are shaping 2026 opportunities
This episode is especially valuable for operators, investors, and entrepreneurs looking for an honest, experience driven perspective on navigating cycles in hospitality and building with intention.
Connect & Invest with Jake:
Follow Jake on X: ⁠https://x.com/JWurzak⁠
1 on 1 coaching with Jake: ⁠https://www.jakewurzak.com/coaching⁠
Learn How to Invest with DoveHill: ⁠https://bit.ly/3yg8Pwo⁠
Topics:
(00:00:00) - Intro
(00:01:15) - Highs of 2025: acquisitions and successes
(00:07:03) - Lessons learned and mistakes made
(00:17:02) - Looking ahead to 2026: trends and predictions
(00:28:57) - Conclusion and exciting news for 2026
(00:29:51) - Closing remarks and podcast information
31 min
November 05, 2025 Experience is the New Asset Class - Sean Hehir - President & CEO - Trinity Investments
In his return to Masters of Moments, Sean Hehir joins Jake Wurzak for a deeper dive into the future of hospitality, technology, and investment strategy. Building on their first conversation, Sean shares how his firm has embraced AI to transform operations and asset management, using data to predict market shifts and enhance efficiency across a global portfolio. He also discusses the evolving landscape of hotel investing, from luxury experiential travel to large-scale renovations, offering candid insights into leadership, culture, and the importance of partnering with the right people.
They discuss:
• How AI and predictive data are reshaping hotel asset management
• The rise of experiential travel and why it’s redefining hospitality investment
• Strategic lessons from major hotel renovations like The Diplomat and The White Barn Inn
• The balance between people, culture, and technology in scaling a global firm
• The future of hospitality investment, from Europe to experiential and wellness-driven models
Links:
Sean on LinkedIn - https://www.linkedin.com/in/sean-hehir/
Trinity Investments - https://www.trinityinvestments.com/
Connect & Invest with Jake:
Follow Jake on X: ⁠https://x.com/JWurzak⁠
1 on 1 coaching with Jake: ⁠https://www.jakewurzak.com/coaching⁠
Learn How to Invest with DoveHill: ⁠https://bit.ly/3yg8Pwo⁠
Topics:
(00:00:00) - Intro
(00:01:32) - AI in business: Transforming operations
(00:04:06) - Asset management and predictive analytics
(00:05:16) - Hospitality industry trends and adaptations
(00:10:22) - Luxury vs. commodity hotels
(00:14:12) - Strategizing hotel acquisitions
(00:23:22) - Navigating challenges and maintaining culture
(00:24:54) - Capital strategy and market dynamics
(00:41:35) - Challenges of raising a first-time fund
(00:42:15) - Finding a niche in hospitality real estate
(00:43:17) - Balancing fundraising and deal focus
(00:44:40) - Sourcing deals: Marketed vs. off-market
(00:46:35) - Choosing the right partners
(00:48:16) - The Standard in London deal
(00:50:24) - Maintaining entrepreneurial culture
(00:54:39) - Biggest mistakes and wins in asset management
(00:57:40) - Impact of politics on investing strategy
(00:58:38) - Innovative renovation strategies
(01:00:52) - Exploring new opportunities in hospitality
(01:03:39) - The importance of service in luxury hotels
(01:09:12) - Future aspirations and gratitude
(01:10:35) - Favorite hotels and unique experiences
1 hr 16 min
October 22, 2025Elevating Hospitality Through Light, Sound, and Space - John Grossman - CEO of Grossman Company Properties
In his second appearance on Masters of Moments, John Grossman joins Jake Wurzak for a deep dive into the philosophy behind his company’s approach to design, operations, and long-term ownership in hospitality.
John discusses why “not fighting the building” remains a guiding principle for every renovation, how his team balances creativity with practicality, and the mindset that drives their additive development strategy. The conversation explores the Arizona Grand Resort renovation, the rebranding of Laguna’s Casa Loma Beach Hotel, and how music, lighting, and landscaping are used to create emotionally resonant guest experiences.
They discuss:
The “Hippocratic Oath” of design and how to avoid overbuilding

Lessons from large-scale repositioning projects like Arizona Grand

Creating timeless design through restraint, light, and color

How thoughtful landscaping and lighting can redefine a property’s atmosphere

Integrating music and art as central elements of hospitality design
Links:
Grossman Company Properties - https://www.grossmancompany.com/
Connect & Invest with Jake:
Follow Jake on X: ⁠https://x.com/JWurzak⁠
1 on 1 coaching with Jake: ⁠https://www.jakewurzak.com/coaching⁠
Learn How to Invest with DoveHill: ⁠https://bit.ly/3yg8Pwo⁠
Topics:
(00:00:00) - Intro
(00:01:01) - The Hippocratic oath of physical space
(00:03:38) - Investing in existing assets vs. pure development
(00:05:49) - Arizona Grand Resort renovation
(00:09:52) - Balancing cost and design in hotel renovations
(00:26:43) - The importance of landscaping and exterior experiences
(00:37:09) - Changes in hospitality industry
(00:42:58) - Challenges in the current market
(00:44:47) - Inspiration from Consortium Holdings
(00:55:07) - Repositioning iconic hotels
(01:13:51) - Innovative music programming
(01:19:42) - Closing thoughts and recommendations
1 hr 22 min
October 15, 2025Inside Dovehill's Latest Acquisition - Charles Paloux - Chief Investment Officer - Dovehill
In this episode of Masters of Moments, host Jake Wurzak sits down with his colleague and DoveHill’s Chief Investment Officer, Charles Paloux, to discuss their firm’s recent acquisition of the White Barn Inn in Kennebunkport, Maine. Jake and Charles take listeners behind the scenes of the deal, from the story of how it came together to the strategy behind investing in luxury experiential hotels. They also share how the property’s unique history, location, and design make it one of the most compelling additions to the DoveHill portfolio.
They discuss:
Charles’s career journey from France to leading hotel investments in the U.S.

The strategy behind DoveHill’s Opportunity Fund II and focus on experiential assets

Why Kennebunkport and the White Barn Inn represent enduring hospitality value

Key elements of the property’s success, from its iconic restaurant to the innovative houseboat suites

How thoughtful capital improvements and community engagement can enhance both guest experience and investment returns
Connect & Invest with Jake:
Follow Jake on X: ⁠https://x.com/JWurzak⁠
1 on 1 coaching with Jake: ⁠https://www.jakewurzak.com/coaching⁠
Learn How to Invest with DoveHill: ⁠https://bit.ly/3yg8Pwo⁠

Topics:
(00:00:00) - Intro
(00:02:16) - Charles' journey in the hospitality industry
(00:14:04) - The White Barn Inn acquisition
(00:18:14) - Operational excellence and future plans
(00:35:25) - Revenue potential
(00:42:43) - Sourcing capital and investor strategy
(00:46:47) - Guest room enhancements and CapEx
(00:49:40) - Spa and guest experience improvements
(00:54:47) - Future investments and market strategy
(01:01:22) - Staff happiness and CapEx projects
(01:03:31) - Conclusion and contact information
1 hr 6 min
October 08, 2025 The Culinary Brilliance Behind Hilton & Wolfgang Puck - Adam Crocini, SVP of Global Design, Wellness, and Food & Beverage @ Hilton
In this episode of Masters of Moments, Jake Wurzak sits down with hospitality leader Adam Crocini for a deep dive into the intersection of food, beverage, and hotel design. Adam shares his journey from working as a teenage barback in Connecticut to shaping global hospitality experiences with iconic brands like Wolfgang Puck, Capella Hotels, and Hilton. Together, they explore how restaurant culture defines hotel success, the role of thoughtful design in guest experience, and why details, from lighting to linen color, can transform an entire property.
They discuss:
• The early influences that sparked Adam’s passion for hospitality
• Lessons learned from building and leading world-class restaurants and hotel programs
• How food and beverage can be the defining feature of a hotel brand
• The importance of design diversity and collaboration between hotel and restaurant designers
• Global labor and service culture differences shaping the future of hospitality

Topics:
(00:00:00) - Intro
(00:01:03) - Adam’s career and background
(00:05:57) - Challenges and failures in the restaurant business
(00:09:26) - The role of landlords and location in restaurant success
(00:12:19) - The impact of food and beverage on hotel differentiation
(00:14:53) - The evolution of hotel food and beverage
(00:20:02) - Designing successful hotel restaurants
(00:36:00) - Balancing independent and hotel restaurant operations
(00:42:39) - Reflecting on past experiences
(00:43:30) - Challenges and strategies in hospitality
(00:48:03) - Global perspectives on service culture
(00:50:09) - The evolution of Singapore's hospitality industry
(00:53:49) - Labor challenges in the U.S. hospitality sector
(01:02:00) - Transitioning to hotel management
(01:10:23) - The importance of details in luxury hotels
(01:15:55) - Future opportunities in hospitality
(01:25:39) - Favorite hotels and closing thoughts

Links:
Adam on LinkedIn - https://www.linkedin.com/in/adam-crocini/
Connect & Invest with Jake:
Follow Jake on X: https://x.com/JWurzak
1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching
Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo
1 hr 29 min
September 24, 2025Building the Boutique for the Outdoors - Ben Weinberg - Co-Founder & Co-CEO at Trailborn
In this episode, Jake Wurzak sits down with Ben Weinberg to discuss the intersection of entrepreneurship, hospitality, and real estate. Ben shares his journey from investment banking into building Trailborn, a brand focused on transforming three-star properties into four-star experiences in iconic outdoor destinations.
The conversation covers the strategy behind unlevered value creation, the complexities of scaling hospitality businesses, and the importance of design, culture, and people in creating memorable guest experiences. Ben also reflects on raising institutional capital, balancing investment returns with brand-building, and the lessons learned from operating across multiple properties.

They discuss:
How Ben transitioned from finance to hospitality entrepreneurship

The evolution of unlevered value creation in today’s higher interest rate environment

Trailborn’s approach to converting underperforming assets into distinctive four-star experiences

The importance of design, unified branding, and thoughtful guest touchpoints

Building a scalable team, culture, and reporting structure to drive growth
Links:
Ben on LinkedIn -https://www.linkedin.com/in/ben-weinberg-29644156/
Trailborn - https://www.trailborn.com/
Connect & Invest with Jake:
Follow Jake on X: https://x.com/JWurzak
1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching
Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:
(00:00:00) - Intro
(00:01:00) - Ben’s background and career
(00:03:25) - How unlevered value creation has changed
(00:05:48) - Learning the operating chops
(00:08:33) - Making the transition into entrepreneurship and hospitality
(00:15:02) - The Trailborn strategy
(00:24:13) - Site selection criteria + conversion example
(00:33:29) - Design theory and vertical integration
(00:37:22) - Learning timing and budgets the hard way
(00:39:34) - Keeping a pulse on the business
(00:44:37) - Staffing strategies
(00:48:03) - The power of thoughtfulness
(00:53:40) - Balancing investment returns and building an incredible brand
(00:56:32) - Raising capital
(01:03:00) - Investing in people
(01:12:41) - What is your favorite hotel?
1 hr 15 min
August 13, 2025Building a REIT in Hospitality - Jay Shah - Executive Chairman of Hersha Hotels & Resorts
Hersha Hospitality Trust (NYSE: HT) is a self-advised real estate investment trust in the hospitality sector, which owns and operates luxury and lifestyle hotels in urban gateway and regional resort markets. The Company’s 25 hotels totaling 3,811 rooms are located in New York, Washington, DC, Boston, Philadelphia, South Florida, and California.
Jay is involved in all areas of the business with a particular emphasis on strategic relationships, capital transactions, asset management, and acquisitions.
On this episode, Jake and Jay discuss:
The story of building Hersha into a publicly-traded powerhouse

Pros & cons of a REIT and starting one in the Hospitality sector

How to think about the market

Missed opportunities and biggest wins
Connect & Invest with Jake:
Follow Jake on X: https://x.com/JWurzak
1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching
Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo
Links:
Hersha Hospitality Trust
Jay on LinkedIn
The 4 Seasons Boston

Timestamps:
(00:00:00) - Intro
(00:02:39) Jay & Jake’s relationship and Jay’s first hotel in NYC
(00:09:30) Opening a hotel amidst the chaos of 9/11
(00:11:25) Was NYC a way to legitimize your business?
(00:31:33) What struggles are there in operating a REIT?
(00:40:33) How would you advise a Hospitality company before they form a REIT?
(00:43:34) Why did you transition into full-service and lifestyle operations?
(00:50:22) What do you think about as an owner and non-operator that you can influence?
(00:53:10) What do you look for when you visit your own hotels, competitors, or one you might acquire?
(00:57:14) What are your thoughts on spending Capex on renovations where you don’t see more upside?
(01:00:01) What have you found the best ways to structure F&B deals?
(01:06:25) How will you be investing in the future given the shifts from covid?
(01:09:53) What’s the most common ways people get smoked in the Hotel business?
(01:11:19)Jay’s growth mindset
(01:15:25) Growing a Management Company
(01:18:24) What makes a really good partner?
(01:21:28) What’s a market you’re interested in?
(01:22:49) What is your favorite hotel?

This Episode originally aired on May 31st, 2023
1 hr 28 min
July 30, 2025 Building a Scalable Hotel Brand in High-Barrier Leisure Markets - Matthew Mering - EVP of Hospitality - Waterton
In this episode of Masters of Moments, Jake Wurzak sits down with Matthew Mering to explore the evolution of lifestyle hotels and the founding story behind Outbound Hotels. From his early experiences in the hospitality industry, starting with bartending at Club Med to co-founding a nightclub while attending business school. Matthew shares how his path ultimately led to building a distinct hotel brand focused on outdoor destinations.

He and Jake dig into the nuanced thinking behind site selection, brand building, operations, and capital strategy, offering a masterclass in how to create hospitality experiences that resonate deeply with both travelers and local communities.

They discuss:
* Why Outbound Hotels targets seasonal, outdoor-focused markets with high barriers to entry
* How brand consistency is balanced with property-level flexibility using a “soft brand” approach
* The value of partnering with Gettys Group and CoralTree to stay lean yet vertically integrated
* Why strong local GMs and creative directors are essential to outperforming in independent hotels
* How AI and social media are disrupting traditional hotel loyalty and booking behavior

A must-listen for anyone building or investing in the future of independent hospitality.

Links:
Matthew on LinkedIn - https://www.linkedin.com/in/mattmering/
Waterton - https://www.waterton.com/

Connect & Invest with Jake:
Follow Jake on X: https://x.com/JWurzak
1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching
Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:
(00:00:00) - Intro
(00:00:42) - Matthew’s background and career
(00:15:06) - Launching Outbound Hotels
(00:17:59) - The importance of location in hotel development
(00:27:11) - Creating unique guest experiences
(00:30:46) - Challenges and rewards of remote hotel locations
(00:35:20) - Deal evaluations, renovation challenges and strategies
(00:40:59) - Navigating the pandemic: Jackson Hole project
(00:44:42) - Operational insights: The importance of good management
(00:54:53) - Marketing innovations: Embracing the outdoorsy campaign
(00:57:10) - AI and technology: The future of hospitality
(01:01:07) - Lessons learned: Mistakes and low leverage strategy
(01:04:14) - Favorite hotels and closing remarks
1 hr 7 min

About Masters of Moments

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Masters of Moments involves conversations with top entrepreneurs and business leaders about hospitality, Real Estate investing, and company building. We explore the ideas, strategies, and approaches…