Masters of Moments

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

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

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

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

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