Masters of Moments

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.

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.

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.

Hunt Rose, co-founder of TruCore Investments, specializes in Class B industrial real estate. He discusses the resilience and appeal of investing in under-managed assets within infill markets. Hunt shares insights on strategic local brokerage relationships and the importance of tenant relations in optimizing investment outcomes. He explains his firm's innovative underwriting process and how they navigate ownership complexities. Their approach to transitioning leases and focusing on transparent investor communication adds a practical touch to scaling their investment strategy.

Brian Harper, co-founder of 11North Partners and former CEO of RPT Realty, shares his decades of experience in retail real estate. He discusses the principles of great retail, emphasizing hospitality and community. Brian reflects on the resurgence of physical retail, lessons from corporate turnarounds, and the distinct cultures of public versus founder-led companies. Personal experiences, including raising a son with autism, have profoundly shaped his leadership approach. This conversation reveals how resilience and values drive the creation of enduring retail platforms.