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Masters of Moments

Masters of Moments

Jake Wurzak 130 Episodes Feb 25, 2026

Masters of Moments features conversations with top entrepreneurs and business leaders about hospitality, real estate investing, and company building. The podcast explores the ideas, strategies, and approaches that brought guests to where they are today. It targets seasoned investors, upstart entrepreneurs, and anyone looking to break into real estate and hospitality investing. Host Jake Wurzak is the CEO of DoveHill Capital Management and Wurzak Hotel Group, a vertically integrated hospitality investment platform. Since 2011, he has led the investment of $1.5 billion in hotel assets across the country.

Episodes

How to Develop Profitable Boutique Hotels - Ethan Orley - Managing Partner at Oliver Hospitality
How to Develop Profitable Boutique Hotels - Ethan Orley - Managing Partner at Oliver Hospitality Feb 25, 2026 4180 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 e
How Omni Aligns Real Estate, Operations, and Guest Experience - Kurt Alexander - President of Omni Hotels & Resorts
How Omni Aligns Real Estate, Operations, and Guest Experience - Kurt Alexander - President of Omni Hotels & Resorts Feb 4, 2026 4309 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 Om
Wrapping up 2025: Wins, Losses, and Predictions for The Hospitality Industry
Wrapping up 2025: Wins, Losses, and Predictions for The Hospitality Industry Jan 7, 2026 1831 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 R
Experience is the New Asset Class - Sean Hehir - President & CEO - Trinity Investments
Experience is the New Asset Class - Sean Hehir - President & CEO - Trinity Investments Nov 5, 2025 4527 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 lands
Elevating Hospitality Through Light, Sound, and Space - John Grossman - CEO of Grossman Company Properties
Elevating Hospitality Through Light, Sound, and Space - John Grossman - CEO of Grossman Company Properties Oct 22, 2025 4877 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 additi
Inside Dovehill's Latest Acquisition - Charles Paloux - Chief Investment Officer - Dovehill
Inside Dovehill's Latest Acquisition - Charles Paloux - Chief Investment Officer - Dovehill Oct 15, 2025 3908 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. Th
The Culinary Brilliance Behind Hilton & Wolfgang Puck - Adam Crocini, SVP of Global Design, Wellness, and Food & Beverage @ Hilton
The Culinary Brilliance Behind Hilton & Wolfgang Puck - Adam Crocini, SVP of Global Design, Wellness, and Food & Beverage @ Hilton Oct 8, 2025 5287 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
Building the Boutique for the Outdoors - Ben Weinberg - Co-Founder & Co-CEO at Trailborn
Building the Boutique for the Outdoors - Ben Weinberg - Co-Founder & Co-CEO at Trailborn Sep 24, 2025 4492 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 com
Building a REIT in Hospitality - Jay Shah - Executive Chairman of Hersha Hotels & Resorts
Building a REIT in Hospitality - Jay Shah - Executive Chairman of Hersha Hotels & Resorts Aug 13, 2025 5268 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
Building a Scalable Hotel Brand in High-Barrier Leisure Markets - Matthew Mering - EVP of Hospitality - Waterton
Building a Scalable Hotel Brand in High-Barrier Leisure Markets - Matthew Mering - EVP of Hospitality - Waterton Jul 30, 2025 4013 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 br
The Street Smart Success Podcast - Jake Wurzak
The Street Smart Success Podcast - Jake Wurzak Jul 25, 2025 3062 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 b
Deploying Over $2B into Mispriced Real Estate - Ian Ross - Founder at Somera Road
Deploying Over $2B into Mispriced Real Estate - Ian Ross - Founder at Somera Road Jul 16, 2025 4307 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 ne

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