Masters of Moments

Jake Wurzak
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Masters of Moments

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

    1D AGO

    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

    1h 12m
  2. Why Florida is the Future of Luxury Real Estate - Isaac Toledano - Co-Founder of BH Group [2024]

    JUL 2

    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?

    1h 8m
  3. Lessons from Scaling a $400K Restaurant into a $6M Flagship - Jeremy Sasson - CEO @ Heirloom Hospitality

    JUN 18

    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

    1h 33m
  4. Coaching Call: Creating Investor Reports People Will Love

    JUN 4

    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

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

    MAY 21

    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

    1h 19m
  6. The BEST Asset Class in Commercial Real Estate - Hunt Rose - Partner at TruCore Investments

    MAY 14

    The BEST Asset Class in Commercial Real Estate - Hunt Rose - Partner at TruCore Investments

    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

    1h 12m
  7. Building Retail Platforms That Endure Across Cycles and Challenges - Brian Harper - 11North Partners

    MAY 7

    Building Retail Platforms That Endure Across Cycles and Challenges - Brian Harper - 11North Partners

    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?

    1h 19m
  8. Inside the Success of Vision Hospitality Group - Mitch Patel - Founder of Vision Hospitality Group

    APR 30

    Inside the Success of Vision Hospitality Group - Mitch Patel - Founder of Vision Hospitality Group

    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

    1h 47m
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4.9
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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 - 2025
  • Episodes
    119
  • Rating
    Explicit
  • Copyright
    © Copyright 2024
  • Show Website
    Masters of Moments

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