Masters of Moments

Jake Wurzak
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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

  1. How to Develop Profitable Boutique Hotels - Ethan Orley - Managing Partner at Oliver Hospitality

    1D AGO

    How to Develop Profitable Boutique Hotels - Ethan Orley - Managing Partner at Oliver Hospitality

    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

    1h 10m
  2. How Omni Aligns Real Estate, Operations, and Guest Experience - Kurt Alexander - President of Omni Hotels & Resorts

    FEB 4

    How Omni Aligns Real Estate, Operations, and Guest Experience - Kurt Alexander - President of Omni Hotels & Resorts

    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

    1h 12m
  3. Wrapping up 2025: Wins, Losses, and Predictions for The Hospitality Industry

    JAN 7

    Wrapping up 2025: Wins, Losses, and Predictions for The Hospitality Industry

    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

    31 min
  4. Experience is the New Asset Class - Sean Hehir - President & CEO - Trinity Investments

    11/05/2025

    Experience is the New Asset Class - Sean Hehir - President & CEO - Trinity Investments

    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

    1h 15m
  5. Elevating Hospitality Through Light, Sound, and Space - John Grossman - CEO of Grossman Company Properties

    10/22/2025

    Elevating Hospitality Through Light, Sound, and Space - John Grossman - CEO of Grossman Company Properties

    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

    1h 21m
  6. Inside Dovehill's Latest Acquisition - Charles Paloux - Chief Investment Officer - Dovehill

    10/15/2025

    Inside Dovehill's Latest Acquisition - Charles Paloux - Chief Investment Officer - Dovehill

    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

    1h 5m
  7. The Culinary Brilliance Behind Hilton & Wolfgang Puck - Adam Crocini, SVP of Global Design, Wellness, and Food & Beverage @ Hilton

    10/08/2025

    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

    1h 28m
  8. Building the Boutique for the Outdoors - Ben Weinberg - Co-Founder & Co-CEO at Trailborn

    09/24/2025

    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?

    1h 15m
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Trailer

4.9
out of 5
35 Ratings

About

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

Information

  • Creator
    Jake Wurzak
  • Years Active
    2023 - 2026
  • Episodes
    130
  • Rating
    Clean
  • Copyright
    © Copyright 2025
  • Show Website
    Masters of Moments

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