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:

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

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

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

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:

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:

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

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

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?