Masters of Moments

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

Charles Paloux, Chief Investment Officer at DoveHill, shares his journey from France to leading U.S. hotel investments. He dives into the acquisition of the White Barn Inn, exploring its unique history and appeal. Charles discusses the value of experiential hotels and why Kennebunkport is a prime location. He highlights innovative concepts like houseboat suites and their potential for profitability. The conversation also touches on community engagement, operational strategies, and enhancing guest experiences, all crucial to thriving in luxury hospitality.

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

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?

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

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

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

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.

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?

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.