Masters of Moments

Jake Wurzak

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. Building a REIT in Hospitality - Jay Shah - Executive Chairman of Hersha Hotels & Resorts

    13 DE AGO.

    Building a REIT in Hospitality - Jay Shah - Executive Chairman of Hersha Hotels & Resorts

    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

    1h28min
  2. Building a Scalable Hotel Brand in High-Barrier Leisure Markets - Matthew Mering - EVP of Hospitality - Waterton

    30 DE JUL.

    Building a Scalable Hotel Brand in High-Barrier Leisure Markets - Matthew Mering - EVP of Hospitality - Waterton

    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

    1h7min
  3. 25 DE JUL.

    The Street Smart Success Podcast - Jake Wurzak

    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

    51min
  4. Deploying Over $2B into Mispriced Real Estate - Ian Ross - Founder at Somera Road

    16 DE JUL.

    Deploying Over $2B into Mispriced Real Estate - Ian Ross - Founder at Somera Road

    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

    1h12min
  5. Why Florida is the Future of Luxury Real Estate - Isaac Toledano - Co-Founder of BH Group [2024]

    2 DE JUL.

    Why Florida is the Future of Luxury Real Estate - Isaac Toledano - Co-Founder of BH Group [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?

    1h8min
  6. Lessons from Scaling a $400K Restaurant into a $6M Flagship - Jeremy Sasson - CEO @ Heirloom Hospitality

    18 DE JUN.

    Lessons from Scaling a $400K Restaurant into a $6M Flagship - Jeremy Sasson - CEO @ Heirloom Hospitality

    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

    1h33min
  7. Coaching Call: Creating Investor Reports People Will Love

    4 DE JUN.

    Coaching Call: Creating Investor Reports People Will Love

    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

    47min
  8. Inside the Playbook for Operational Excellence Across Hotel Types - Greg Kennealey - CEO @ Peregrine Hospitality

    21 DE MAI.

    Inside the Playbook for Operational Excellence Across Hotel Types - Greg Kennealey - CEO @ Peregrine Hospitality

    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

    1h19min
4,9
de 5
35 avaliações

Sobre

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

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