

Masters of Moments
Jake Wurzak
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 that brought them to where they are today. This podcast is for you if you are a seasoned investor, an upstart entrepreneur, or someone looking to break into the real estate and hospitality investing world. Jake Wurzak is the CEO of DoveHill Capital Management and Wurzak Hotel Group, a leading vertically integrated hospitality investment platform. Since 2011, he’s led the investment of $1.5 billion in hotel assets throughout the country. Follow Jake on Twitter: https://twitter.com/JWurzak Take the Hospitality Real Estate Investing Masterclass: https://learn.jakewurzak.com/ Subscribe to the show on YouTube: https://www.youtube.com/channel/UCzvzdJASDiEXhV9VhkaEoWA Learn How to Invest with DoveHill: https://dovehillcos.junipersquare.com/portal/view_lead_capture_form/MzhmOGE4MTUwMjZhNDZkNmU1MGE0NmYwOTdhZjk2MzAxYzE0MjIzMGdBV1ZEUUFBQUFBQUFBQW9UVzhJVFdzTlRrNkpkSlF1 DoveHill: www.dovehillcos.com
Episodes
Mentioned books

Oct 8, 2025 • 1h 28min
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

Sep 24, 2025 • 1h 15min
Building 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?

Aug 13, 2025 • 1h 28min
Building 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

Jul 30, 2025 • 1h 7min
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

6 snips
Jul 25, 2025 • 51min
The Street Smart Success Podcast - Jake Wurzak
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
(00:01:40) - Jake's journey in the hospitality industry
(00:04:18) - The evolution of hotel investments
(00:05:29) - Challenges and opportunities in boutique hotels
(00:08:53) - Focus on independent lifestyle hotels
(00:15:59) - Preferred equity investments in hospitality
(00:17:34) - Development and operational strategies
(00:21:46) - Vetting partners in hotel investments
(00:27:45) - Key metrics for hotel success
(00:28:32) - Challenges in hotel operations
(00:28:43) - Financial management in hotels
(00:29:28) - Efficiency and profitability
(00:30:22) - Value add strategies in hospitality
(00:34:07) - Third party management in hotels
(00:41:44) - Impact of external factors on hotels
(00:44:51) - AI and innovation in hotel management
(00:46:47) - Lessons learned and personal insights
(00:50:11) - Conclusion and contact information

Jul 16, 2025 • 1h 12min
Deploying Over $2B into Mispriced Real Estate - Ian Ross - Founder at Somera Road
Ian Ross, founder of Somera Road, shares his entrepreneurial journey in opportunistic real estate, overseeing nearly $2.5 billion in acquisitions. He emphasizes the significance of micro-neighborhoods and local expertise at a national scale. The conversation highlights placemaking in office and hotel assets, the balance between local knowledge and macro trends, and innovative strategies for community engagement. Ross also discusses the evolving landscape of family office investments, stressing relationship-building as key to navigating fundraising challenges.

Jul 2, 2025 • 1h 8min
Why Florida is the Future of Luxury Real Estate - Isaac Toledano - Co-Founder of BH Group [2024]
In this episode of Masters of Moments, Jake Wurzak sits down with Isaac Toledano for a wide-ranging conversation on his entrepreneurial journey, development philosophy, and deep commitment to Florida real estate. Isaac reflects on his early start in business at age 15 in Israel, how his risk appetite has evolved, and why partnerships are at the center of his approach. He offers a behind-the-scenes look at marquee deals like Fisher Island and Naples, sharing his methods for evaluating sites, structuring deals, and maintaining a lean, hands-on operation across 31 active projects. Isaac also dives into the importance of location, timing, and branding in condo development, and why he believes Florida remains the best place to live, work, and invest.
We discuss:
Why Isaac always partners with experienced developers instead of building teams himself
The deal structure and timing behind his landmark $122M Fisher Island acquisition
How he evaluates risk, and why he chooses to operate exclusively in Florida
The value of hands-on involvement and simple deal terms in executing large transactions
What buyers expect today in branded luxury condos and how developers can meet that standard
Isaac's primary focus centers on luxury residential properties, prime land holdings, office spaces, and mixed-use assets strategically positioned in prime locations. BH Group mitigates risk exposure by targeting large-scale, value-adding prospects within specialized markets while maximizing returns. BH Group has forged partnerships with leading real estate firms in the United States, successfully completing over 1,100 luxury residential units, with an additional 10,000 units in progress.
This episode originally released in August of 2024.
Links:
BH Group - https://www.bhgroupmiami.com/
Connect & Invest with Jake:
Follow Jake on Twitter: https://twitter.com/jwurzak
Take the Hospitality Investing Masterclass: https://learn.jakewurzak.com/
Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo
Topics:
(00:00:00) - Intro
(00:02:33) - Isaac’s upbringing in Israel and career
(00:06:56) - Coming to the United States and the love for Florida
(00:12:38) - What are your partner’s perceptions of you?
(00:15:57) - How do you think about risk and diversification?
(00:17:39) - How involved are you in the deal process?
(00:20:11) - What have you learned about simplicity in complicated transactions?
(00:25:36) - A walkthrough of a condo development
(00:34:18) - Target returns & deal structures
(00:37:25) - How are you compensated for your work?
(00:39:57) - What area of Florida are you interested in investing in?
(00:42:59) - Timing construction with sales
(00:46:56) - Branding
(00:51:59) - The future of Florida
(01:00:09) - Isaac’s biggest mistake, marriage, and parenting
(01:02:41) - Negotiation
(01:05:04) - What is your favorite hotel?

Jun 18, 2025 • 1h 33min
Lessons from Scaling a $400K Restaurant into a $6M Flagship - Jeremy Sasson - CEO @ Heirloom Hospitality
Jeremy Sasson, CEO of Heirloom Hospitality, shares his journey from a post-college startup grind to building beloved restaurants in Detroit without external funding. He emphasizes a guest-first approach, explaining how every design element influences guest emotions. Jeremy reveals why he left a family real estate business for hospitality, highlights the importance of strong team dynamics, and discusses how to navigate cultural fit in staffing. His insights on balancing aesthetics with functionality and adapting to market changes provide invaluable lessons for anyone passionate about creating lasting dining experiences.

Jun 4, 2025 • 47min
Coaching Call: Creating Investor Reports People Will Love
Discover how to create engaging investor reports that people actually want to read. Explore the importance of clarity, consistency, and tailored content based on investor relationships. Learn about balancing detailed metrics with high-level narratives, and avoid common pitfalls that can turn investors off. Jake shares tips on leveraging reports as strategic communication tools and the significance of transparency for building long-term trust. Visual presentation and storytelling through numbers are also highlighted as key elements for successful investor relations.

26 snips
May 21, 2025 • 1h 19min
Inside the Playbook for Operational Excellence Across Hotel Types - Greg Kennealey - CEO @ Peregrine Hospitality
Greg Kennealey, CEO of Peregrine Hospitality, shares his wealth of knowledge from his extensive background at Strategic Hotels and KSL Capital. He delves into the evolving hotel investment landscape, emphasizing the importance of aligning operational practices with ownership mindset. The discussion covers strategic labor management, the role of KPIs in performance, and the rise of independent resorts. Greg also highlights the need for innovative guest experiences and the culture of accountability that drives success, making this a must-listen for hospitality enthusiasts.