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

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: Charles’s career journey from France to leading hotel investments in the U.S. The strategy behind DoveHill’s Opportunity Fund II and focus on experiential assets Why Kennebunkport and the White Barn Inn represent enduring hospitality value Key elements of the property’s success, from its iconic restaurant to the innovative houseboat suites How thoughtful capital improvements and community engagement can enhance both guest experience and investment returns 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 (00:02:16) - Charles' journey in the hospitality industry (00:14:04) - The White Barn Inn acquisition (00:18:14) - Operational excellence and future plans (00:35:25) - Revenue potential (00:42:43) - Sourcing capital and investor strategy (00:46:47) - Guest room enhancements and CapEx (00:49:40) - Spa and guest experience improvements (00:54:47) - Future investments and market strategy (01:01:22) - Staff happiness and CapEx projects (01:03:31) - Conclusion and contact information

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 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: Building SomeraRoad Micro-neighborhoods Having local expertise at a national scale Placemaking and Hospitality in Office and Hotel assets 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

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 joins Jake Wurzak to unpack his obsessive, guest-first approach to hospitality and share how he’s built a thriving portfolio of restaurants without external investors or debt. The conversation traces Jeremy’s evolution from a post-college startup grind to crafting some of Detroit’s most beloved dining experiences. He explains how design, service, and team alignment all flow from a single emotional driver: how a guest feels at every touchpoint. Jeremy also reveals how he builds restaurants through the lens of fashion, explains the overlooked costs of doing hospitality well, and offers rare insight into the operational decisions that separate great concepts from lasting brands. We discuss: Why every element of a restaurant must begin with how it makes guests feel The core reasons he turned down the family real estate business to pursue hospitality What he learned building his first restaurant with no industry experience Why he avoids celebrity chefs and prioritizes team members who “pick him” The importance of eliminating weak cultural fits—even when it hurts in the short term This episode is a masterclass for anyone building hospitality experiences with purpose and longevity in mind. Links: Heirloom Hospitality - https://heirloomhospitality.com/ Jeremy on LinkedIn - https://www.linkedin.com/in/jeremy-sasson-a172b3195/ 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 (00:01:10) - Jeremy's college days and early ventures (00:03:38) - First steps in hospitality (00:06:40) - Lessons from family and early career (00:13:27) - The birth of a restaurant vision (00:16:26) - Starting the first restaurant: Challenges and triumphs (00:23:55) - Evolving the restaurant business (00:28:34) - Vision and execution: Creating unique dining experiences (00:46:13) - Designing the restaurant experience (00:48:03) - Service excellence and staff roles (00:50:09) - Consistency across multiple locations (00:53:06) - Core values and staff training (00:55:34) - Challenges and adaptations in the restaurant industry (00:57:11) - Design insights and restaurant layout (01:04:18) - Creating the perfect vibe (01:09:33) - Lessons from restaurant pivots (01:20:46) - Expansion strategies and new markets (01:29:51) - Favorite hotels and final thoughts

In this solo Coaching Call episode of Masters of Moments, Jake Wurzak breaks down how to create investor reports that people actually want to read. Drawing from his experience in real estate and hospitality, Jake walks through the fundamentals of reporting with clarity, consistency, and purpose. He shares the essential elements of an effective update, including what data to include, how to tailor content based on your relationship with investors, and how frequency and tone play a role in building trust. The episode also covers the importance of visual presentation, storytelling through numbers, and why transparency is key to long-term partnerships, especially when challenges arise. Jake also touches on: Balancing detailed metrics with high-level narratives Common mistakes that turn investors off How to use reports as a strategic communication tool Structuring reports for quarterly, monthly, or ad hoc updates Leveraging reports to reinforce your brand and vision Whether you're raising capital or already managing a portfolio, this episode is a tactical guide to making your investor communication stand out. Topics: (00:00:00) - Intro (00:00:49) - Effective communication with investors (00:02:06) - Quarterly reports and their importance (00:04:20) - Methods of sharing investor reports (00:05:42) - Hybrid approach to investor updates (00:08:33) - Detailed walkthrough of an investor report (00:19:48) - Common mistakes and best practices (00:23:30) - Challenges of investor webinars (00:25:11) - Setting expectations for investor reports (00:28:09) - Scaling the business and team (00:31:14) - Balancing investor relations and personal investments (00:38:35) - Creating effective investor reports (00:40:20) - Evaluating hotel investments (00:46:09) - Conclusion and final thoughts 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 of Masters of Moments, host Jake Wurzak sits down with Greg Kennealey, CEO of Peregrine Hospitality, for an in-depth conversation on building and operating a diversified hotel platform with a focus on performance, alignment, and long-term value creation. With a career that includes time at Strategic Hotels and KSL Capital, Greg brings both institutional experience and an owner-operator mindset to the conversation. They discuss the evolving landscape of hotel investment, from pandemic-driven shifts in demand and staffing, to the renewed importance of leisure travel, stress-testing models, and driving performance across both luxury resorts and extended-stay properties. Greg also breaks down the founding of Peregrine, their vertically integrated approach, and how alignment and talent are central to outperforming in any market cycle. They also cover: How the best hotel companies earned loyalty by prioritizing staff during COVID Lessons from KSL on underwriting, capital planning, and long-term investing The rise of experiential and independent resorts—and where they see opportunity Why owner-operator models outperform in today’s capital environment The critical role of KPIs like labor margin, guest satisfaction, and revenue flow Designing phantom ownership structures to retain and reward top hotel talent Building a culture of accountability and innovation from the ground up This episode is a masterclass in hospitality execution, told through the lens of someone who has scaled both iconic resorts and margin-driven select-service portfolios—and believes the best teams win every time. Links: Peregrine Hospitality - https://www.peregrinehg.com/ Greg on LinkedIn - https://www.linkedin.com/in/greg-kennealey-946b715/ 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) - Resilience and Challenges in the Hotel Industry (00:03:12) - Investment Strategies and Stress Testing (00:04:59) - Balancing Leisure and Corporate Travel (00:08:21) - Operational Challenges and Innovations (00:34:13) - The Role of Location in Hotel Success (00:38:51) - Conviction in Hotel Investments (00:41:07) - The Complexity of Hotel Ownership (00:41:48) - The Owner-Operator Model (00:44:49) - Sales Strategies and Exit Timing (00:47:21) - Rapid Acquisition Challenges (00:50:12) - Building an Entrepreneurial Venture (00:54:24) - Operational Oversight and KPIs (00:58:40) - Managing Labor Costs (01:01:26) - Investing in Experiential Resorts (01:09:02) - Food and Beverage Strategies (01:15:52) - Future Goals and Favorite Hotels

In this episode of Masters of Moments, host Jake Wurzak sits down with Hunt Rose, co-founder of TruCore Investments, to dive into the business of Class B industrial real estate and what makes it one of the most resilient, overlooked asset classes in today’s market. Drawing on his experience in brokerage and acquisitions, Hunt explains how TruCore’s national platform finds value in under-managed, substitutional assets and why a fragmented ownership base presents a unique opportunity for investors with a focused strategy. They also discuss: The risk-adjusted appeal of Class B industrial assets in infill markets Sourcing deals through local brokerage relationships across 150+ U.S. markets How TruCore approaches marking rents to market with legacy tenants The business case for converting gross leases to triple net structures Functional criteria they use to quickly screen new acquisitions Their “100 questions” underwriting playbook and due diligence process Fund structure, capital raising strategy, and investor communications This episode is a practical, inside look at how a lean team is scaling a national industrial platform by sticking to fundamentals, staying disciplined, and building trust with tenants and investors alike. Links: Hunt Rose on X - https://x.com/nnn_industrial Hunt Rose on LinkedIn - https://www.linkedin.com/in/hunt-rose-9229694b/ TruCore Investments - https://trucoreinvestments.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 (00:00:38) - Landing a deal from a Podcast (00:03:04) - Where are you investing? (00:06:37) - Is sub-institutional scalable? (00:09:00) - The business case for Class B Industrial (00:13:00) - What’s the business plan when you acquire a property? (00:15:42) - Why are rents often times below market? (00:18:23) - Lease renewal approaches (00:22:21) - Converting gross deals to NNN deals (00:24:47) - Where do things go wrong on these deals (00:27:25) - What kills a deal for you? (00:30:30) - Making the entrepreneurial leap (00:36:02) - How have you fine-tuned the acquisition process? (00:38:35) - What do you do differently as an owner that the tenant would recognize? (00:42:14) - The advantage and disadvantage of being the money from out of town (00:45:35) - Are there any tenants you refuse to have on a property? (00:47:54) - Holding strategies (00:49:58) - Establishing a Fund (00:54:09) - Raising capital (01:03:36) - Reporting and investor relationships (01:08:51) - What is your favorite hotel? (01:09:55) - Get in touch with Hunt

In this episode of Masters of Moments, host Jake Wurzak sits down with Brian Harper, co-founder of 11North Partners and former CEO of RPT Realty, to discuss leadership, reinvention, and the enduring relevance of retail real estate. With a background spanning General Growth Properties, Rouse Properties, and RPT, Brian brings decades of insight from navigating some of the most complex moments in the retail sector—including corporate bankruptcies, public-to-private transitions, and large-scale portfolio transformations. They also discuss: * The principles behind great retail: hospitality, curation, and community * Lessons from navigating the GGP and RPT turnarounds * Why physical retail is far from dead—and what’s driving its resurgence * Building culture in public companies vs. founder-led ventures * How personal experiences, including raising a son with autism, have shaped Brian’s leadership style * The founding vision behind 11 North Partners and their thesis on long-term, durable retail This episode offers a grounded, values-driven look at how great retail gets built—and the personal moments that shape the leaders behind it. Links: 11North Partners - http://11northpartners.com/ Brian on LinkedIn - https://www.linkedin.com/in/brian-harper-5431265/ 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 (00:01:08) - Brian’s career and background (00:12:19) - Is retail becoming un-investable? (00:14:52) - Experience and hospitality as an opportunity to save retail (00:16:45) - Brian’s experience at GGP and Rouse (00:23:55) - The collapse of bad malls (00:27:17) - Positioning malls for success (00:37:06) - What makes a spectacular open-air center? (00:40:36) - What retailers are picking the best locations? (00:42:40) - What goes wrong in retail centers? (00:44:26) - Building 11North (01:03:01) - Raising a child with autism (01:17:26) - What is your favorite hotel?

Channeling a passion for the hospitality industry, Mitch Patel established Vision Hospitality Group in 1997 on a foundation of values that guide the organization to this day. With an unwavering commitment to excellence, Mitch oversees every aspect of the company, from investment procurement to the seamless execution of daily operations. Additionally, he oversees strategic development and implementation that has propelled Vision Hospitality Group to garner numerous awards within the industry. Links: Visionary Hospitality Group - https://www.vhghotels.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 (00:00:55) - Mitch’s career and background in hospitality (00:20:40) - What did you learn about risk in the early days of your company and why did you only focus on the hotel asset class? (00:31:39) - How much do you attribute your success to your ability to develop vs. operate? (00:39:15) - How are you able to develop 10 hotels at once? (00:59:05) - Mitch’s passion for experiential and lifestyle hotels (01:20:06) - What are the non-negotiables you put in independent hotels? (01:29:54) - What concerns do you have for the future of hospitality? (01:44:10) - What is your favorite hotel? This episode originally aired in May of 2024

In this episode of Masters of Moments, host Jake Wurzak sits down with Micah Lacher, founder of Anchor Investments, for a deeply personal and wide-ranging conversation about real estate, entrepreneurship, and the power of second chances. From growing up in a struggling household in North Memphis to building a respected investment and development firm in Nashville, Micah’s story is both gritty and inspiring. They begin with Micah’s early exposure to real estate, sparked by a life-changing move that took his family from an unsafe neighborhood to one of the best public school districts in Memphis—secured through an unlikely deal involving two Delta Airlines plane tickets. That experience set the tone for a life shaped by faith, hustle, and resilience. Throughout the episode, Micah shares how he transitioned from a brokerage role at Cushman & Wakefield into real estate development, thanks to the mentorship of Bob Tull, a former Walmart developer. He recounts launching Anchor in the depths of the 2009 financial crisis, raising capital deal-by-deal to purchase distressed assets when few others had the conviction to buy. They also discuss: - The high-stakes risk of personal guarantees during the Great Financial Crisis - How Micah structured deals, underwrote for worst-case scenarios, and still found upside - The transition from broker to principal and the influence of early mentors - Raising children without entitlement while building wealth - Using his business as a platform for purpose and service to the community Micah’s outlook is rooted in gratitude and long-term thinking, with a focus on character, consistency, and building something that matters. This episode is a must-listen for anyone navigating the intersection of values, leadership, and real estate. Links: Micah on LinkedIn - https://www.linkedin.com/in/micah-lacher-1366151/ Anchor Investments - https://www.anchorinv.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 (00:01:14) - Micah’s upbringing (00:08:03) - Early career (00:13:19) - Mentors, marriage, and breaking phone addiction (00:19:17) - The fear of raising entitled children (00:22:16) - Learning the brokerage game (00:30:14) - Transitioning from broker to principal (00:39:24) - Developing “Walmart shadows” and experiencing the GFC (00:45:06) - Raising capital in 2009 (00:51:51) - Thoughts on RTO (00:53:42) - How do you think about your business today, given how you started? (00:57:30) - Using the business to effect change (01:10:37) - Establishing a competitive edge (01:13:08) - Developing hotels in Nashville - and giving away the profits (01:23:11) - The Nashville market (01:27:34) - What’s your favorite hotel?