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:

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

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:

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

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:

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

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:

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

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:

Topics:

(00:00:00) - Intro

Links:

Adam on LinkedIn - https://www.linkedin.com/in/adam-crocini/

Connect & Invest with Jake:

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:

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

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:

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

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

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

This episode is a repost of Jake's appearance on the Street Smart Success Podcast, hosted by Roger Becker. You can learn more about Street Smart Success here - https://www.streetsmartsuccess.com/

Jake shares his journey from working in his family's hotel business to building a portfolio of unique, experience-driven hotels. The conversation explores why commoditized limited-service hotels have become riskier assets, and why independent lifestyle hotels are now some of the most defensible real estate investments. Jake also explains DoveHill’s current focus on preferred equity and bespoke equity investments, the operational insights that drive performance, and the long-term value of brand, location, and customer experience in the hospitality sector.

We discuss:

Why limited-service hotels are becoming riskier due to oversupply and commoditization

How Jake evaluates hotel investments through revenue, profit, and guest satisfaction

The value of great operators and how they can distinguish themselves with food and beverage, accounting, and margin control

Why DoveHill is shifting away from new development and instead prioritizing preferred equity and opportunistic repositioning

The importance of humility, persistence, and attention to detail in long-term success

This episode is ideal for anyone investing in or operating within the hospitality space who wants a deeper understanding of today’s market dynamics.

Topics:

(00:00:00) - Intro

Ian Ross founded SomeraRoad in 2016, bringing a fresh, entrepreneurial approach to opportunistic real estate in growing secondary cities nationwide. He has since led the firm’s rapid expansion, overseeing nearly $2.5 billion in acquisitions of 25+ million square feet in more than 70 unique markets. Ian has also augmented SomeraRoad’s core value-add business, building new verticals in industrial net lease, distressed debt, and opportunity zone investing and creating a robust ground-up development practice. Today, SomeraRoad is arguably the fastest-growing commercial real estate investment and development company in the USA.

On this episode, Jake and Ian discuss:

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:

SomeraRoad

Ian on LinkedIn

Topics:

(00:00:00) - Intro

(00:03:50) - Ian’s entrepreneurial journey

(00:06:27) - Biggest lessons learned on someone else’s dime

(00:08:37) - Do local operators tend to miss out on macro trends?

(00:15:09) - Early decisions to make when considering entering a new asset class

(00:20:05) - Raising capital & funds

(00:28:47) - Focusing on neighborhoods instead of cities

(00:31:13) - Setting up local offices

(00:34:36) - How has your thoughts on placemaking changed?

(00:41:45) - What’s your approach to hospitality?

(00:46:23) - How much do you think about competitors in your local market?

(00:50:58) - 1 Hanover Square

(00:56:51) - Keeping teams interconnected and hiring, 

(00:59:39) - How do you keep the pulse on whether you’re hitting goals?

(01:00:45) - The industrial net lease space

(01:02:26) - Where do you get inspiration?

(01:04:41) - What are your goals for the next 5 years?

(01:05:29) - What’s been your favorite deal?

(01:08:27) - What’s your favorite hotel?

This episode originally aired in February of 2024