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

JRNY is a Canadian whisky created by the Brothers Sean and Chris Pronger with award-winning distillery Niagara Falls Craft Distillers Whisky. 

This episode was originally released March 2024

On this episode, Jake and Chris discuss:

- Life in the NHL, mistakes, and lessons learned

- Developing a professional mindset in athletics and business

- Launching JRNY and competing in the beverage market

Check out JRNY here: https://jrnyspirits.com/

Topics:

(00:00:00) - Intro

(00:04:34) - How youth sports have changed

(00:09:44) - Developing a professional mindset in athletics

(00:12:01) - Misconceptions about leadership in pro sports

(00:14:36) - What it takes to play 19 years in the NHL

(00:16:37) - Transitioning back to civilian life

(00:19:18) - Mentors & investing

(00:33:32) - Discovering yourself after retiring

(00:39:27) - Launching a whiskey brand

(00:52:02) - Bouncing back from failure

(00:53:24) - How to pick great partners in business

(00:58:51) - Competitive advantages

(01:01:17) - Brand inspirations

(01:06:32) - Building relationships

(01:08:57) - Chris’ real estate strategy & career reflections

(01:24:56) - What is your favorite hotel?

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

- Advice to independent developers

- Operating agreements w/ restaurants

- Scaling w/ investors vs. bootstrapping & a ton more!

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

(00:04:38) - Inspirations from Blackberry Farm & Blackberry Mountain

(00:21:14) - Advice to independent developers

(00:25:40) - Operating agreements with third-party restaurants

(00:35:27) - Purchasing an existing hotel vs. developing from the ground up

(00:44:12) - Pop-up hotel experiences

(00:48:03) - Scaling with investors vs. bootstrapping

(00:55:05) - The risk of betting on newer brands

(01:00:21) - Creating a case for a market where there’s little data available to pull

This episode was originally released October 2023

On this episode, Jake & Gabe discuss: 

• Going from Wall St. into Real Estate
• Building Generational Wealth
• Raising Capital
• Executing Value-Add Strategies

Links:

Gabe on Twitter

Tekton Group

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

(00:01:48) Going from Wall St. into Real Estate

(00:09:38) The desire to create generational wealth

(00:11:14) Balancing raising capital while building wealth in assets

(00:14:26) What are some key principles you abide by to protect you against being a forced seller?

(00:20:15) Waiting for the Fat Pitch

(00:25:46) Can you define sub-institutional real estate and what are some market inefficiencies you see around the asset class?

(00:30:43) How do you find deals?

(00:34:07) A walkthrough of a deal that closed 2 weeks later

(00:39:01) How do you execute quickly on your value-add strategy?

(00:43:03) What’s the structure of your fund and why did you decide to have a fund?

(00:47:48) What did you learn from the first and second funds that you’ll implement in the third?

(00:59:18) Have you thought about deals that you never want to sell?

(01:02:28) What have you learned from your worst deal?

(01:06:23) Getting tenant feedback for Capex

(01:08:26) Gabe’s philosophy around 3rd party managers

(01:12:15) What are your goals over the next 3 years?

(01:17:12) What is your favorite hotel?

This episode was originally released March 2023

On this episode, Jake and Vamsi discuss:

• Breaking down Vamsi's first deal
• Growing Arbor Lodging and building a vertically integrated management team
• Maintaining efficient deal pipelines
• Converting Hotels to Multifamily

Links:

Vamsi on LinkedIn

Arbor Lodging Partners

The Grand Hyatt Kauai

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Topics:

(00:01:50) - Vamsi’s journey into Hospitality

(00:06:38) - What happened in your first deal?

(00:08:05) - How did you raise money for the deal?

(00:10:41) - Looking back, what were some of the questions you should have asked in your first deal?

(00:12:14) - How did you structure the deal with investors?

(00:12:57) - Hospitality as a complex asset

(00:14:51) - Were you looking for broken RE deals early on in your career?

(00:17:15) - When did you start to grow your team?

(00:18:57) - What made you decide to bring management in-house?

(00:21:20) - Did institutional partners start to flow in once you became vertically integrated?

(00:22:04) - How has your philosophy been shaped by doing deals in markets outside your own backyard?

(00:25:36) - How do you and your partner figure out what deals and markets you’ll focus on?

(00:28:21) - How do you keep your acquisitions team incentivized and motivated?

(00:31:45) - How do you make sure your deal pipeline is as efficient as possible?

(00:32:52) - What is your strategy for 2023?

(00:34:58) - Are you looking at converting Office to Hotel?

(00:39:40) - Do you have separate capital for Debt and Equity?

(00:42:36) - How do you make the economics work at scale?

(00:45:26) - Why do you work with institutional partners vs. syndicating deals?

(00:53:30) - At what point did you start viewing the management side as its own business?

(00:58:31) - What’s something surprising that you’re doing in the management company?

(1:00:03) - What tools are you using to maintain a pulse on the business?

(1:05:22) - How do you approach hybrid work with your teams?

(1:07:10) - How do you convert hotels to multifamily?

(1:18:13) - What is your favorite hotel?

As CEO, Patrick helps define and implement strategic plans designed to further expand all facets under the CARROLL portfolio. As a disciplined investor, Patrick carefully balances acquisitions and dispositions, and has led to $12.1 B in acquistions and $8.8 B in dispositions of multifamily real estate producing an average gross IRR of 29%.

Founded in 2004, CARROLL marked the beginning of Patrick’s real estate investment and development career. Patrick’s early success in the industry came from residential investments and developmental projects across the Southeast, which, in turn, produced the opportunity to develop retail centers, mixed-use properties, and student housing.

In 2009, Patrick acquired three property management companies, creating the large-scale infrastructure for what CARROLL is today. Compounding on his experience with investment, property management, development, and construction, Patrick has taken a modest initial investment and cultivated that into a 30,000-unit portfolio.

Links:

Patrick Carroll

Patrick on Instagram

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

(00:02:41) - Patrick’s transition from house-flipping to multifamily

(00:14:07) - What was your deal criteria early on?

(00:19:42) - How were you finding deals?

(00:23:30) - How did you scale?

(00:31:54) - Building a profitable management company

(00:33:55) - Raising capital & getting deals done

(00:49:14) - The buy-fix-sell strategy

(01:06:18) - Pausing deals post-covid

(01:08:51) - Selling the business

(01:17:03) - Thoughts on the market today

(01:24:24) - Mental health

(01:29:35) - What’s your favorite hotel?

This episode was originally released June 2023

On this episode, Jake & Arash discuss:

• Key components to creating an amazing branded hotel,
• F&B strategies and why it’s such an important aspect of hospitality,
• Learnings from working with Barry Sternlicht
• Acquiring and scaling brands.

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Links

Highgate

Arash on LinkedIn

The Viceroy Hotel: Sugar Beach at St. Lucia

Timestamps

(00:00:00) Intro

(00:02:38) How do you experience a hotel when you travel and what are you looking for?

(00:05:29) How did you get started in this industry?

(00:09:54) What about your journey has shaped how you are as a leader and how you build brands?

(00:13:02) What are some key elements that separate Hospitality characters from Hospitality business folks?

(00:15:16) How are you making sure employees are bought in?

(00:19:20) How many hotels fall under your portfolio?

(00:21:39) Where are you spending the majority of your time day to day?

(00:23:57) Is there an optimal scale to justify implementing Business Intelligence technology?

(00:27:24) What was most surprising to you when you joined High Gate?

(00:29:12) Do you see branded hotels growing or shrinking?

(00:33:20) Are you working on creating new brands?

(00:42:45) F&B Strategies and amazing restaurant operators

(00:53:54) What are some of the things you learned working with Barry Sternlicht?

(00:57:31) What are some best practices for prioritizing your work?

(01:00:46) How are you trying to grow the business?

(01:04:01) Have you been looking at acquiring brands that your infrastructure is uniquely equipped to scale?

(01:07:01) What mistakes do you see most often from operators and investors?

(01:09:50) What are you seeing in the market forecast?

(01:11:47) What is your favorite hotel?

On top of that, we get into the nitty-gritty of managing hospitality and food & beverage operations, touching on both tax considerations and the complexities of construction contracts, including GMP savings. You’ll also hear some strategic tips on how to scale your investments, make the most of unique property features, and create innovative F&B concepts that not only enhance guest experiences but also boost profitability. Enjoy!

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

(00:02:31) - Delivering bad news to investors

(00:09:33) - Operating companies vs. property company structures

(00:02:27) - Structuring branded residences

(00:23:45) - Structuring for a F&B Leased to a third party

(00:34:09) - Incentive structures for construction management

(00:40:55) - Getting comfortable with first-time operators

(00:49:13) - Why first-time hoteliers fail

(00:58:15) - Best practices for getting a liquor license

This episode was originally released November 2023

On this episode, Jake and Noah discuss:

- Spotting patterns in cycles to take advantage of

- Debt positioning

- Identifying great locations

- Biggest makes for folks getting into the land business

Links:

BTI Partners: https://btipartners.com/

Noah on LinkedIn: https://www.linkedin.com/in/noah-breakstone-97ba576/

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

(00:01:41) - Noah’s background and career in development

(00:11:31) - Spotting patterns in cycles to take advantage of

(00:14:43) - Hold periods and investment horizons

(00:17:02) - Asset class approach

(00:22:53) - Debt positioning

(00:25:49) - Finding the right partners

(00:27:51) - Why did you choose to only operate in Florida?

(00:31:02) - Identifying a great location

(00:32:50) - Long-term concerns for Florida

(00:35:37) - Build for Rent opportunities

(00:41:28) - Does education play a role when looking at land?

(00:44:34) - Housing

(00:56:30) - The impact of distribution centers

(00:59:28) - Biggest mistakes people make getting into the land business

(01:05:01) - How do you know if you’re overpaying or getting a great deal?

(01:07:21) - Identifying a slow-down

(01:16:47) ) - How has your leadership style changed over time?

(01:21:25)- What’s your favorite hotel?

Formed in 2012 as an independent company, the firm carries in its DNA the successful 50-year track record of acquiring and operating multi-tenant commercial real estate assets of Matthew Adler’s legacy family business, the Adler Group.

This episode was originally released December 2023

On this episode, Jake and Matt discuss:

- How the fund investing model has changed risk appetite

- Adding value as an operator

- Matt’s investment strategy

- Creating incentives and deal structures

- Surviving without a promote

- Raising capital

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

Links:

Adler Real Estate Partners

Solo Ep on fees

Four Seasons Golden Triangle Thailand

Topics:

(00:00:00) - Intro

(00:02:00) - The post-covid industrial space

(00:05:02) - Key moments in Matt’s career

(00:08:40) - Gross-to-Net spread

(00:09:59) - How the fund investing model has changed risk appetite

(00:14:11) - Adding value as an operator

(00:16:54) - Matt’s investment strategy

(00:26:10) - Creating incentives and deal structures

(00:38:05) - Surviving without a promote

(00:42:29) - Raising capital

(00:50:34) - Characteristics of a successful reporting memo

(00:53:43) - Managing the business weekly

(00:57:13) - Acquisitions people vs. asset managers

(01:02:12) - The 3 KPI’s that determine whether to pursue a deal

(01:06:57) - Acquisitions and investment size

(01:09:24) - Sourcing deals

(01:11:54) - Thoughts on debt

(01:13:35) - What’s your favorite hotel?

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Topics:

(00:00:00) - Intro

(00:02:32) - Introducing preferred equity

(00:06:15) - Preferred equity and returns

(00:13:03) - Last Dollar Basis

(00:15:55) - Basic structures of preferred equity

(00:19:30) - Control and rights

(00:20:50) - Non-subordination

(00:23:50) - Preferred Equity doesn’t need to be paid current

(00:25:05) - Pitfalls

(00:27:49) - Terms

(00:30:38) - Why Preferred Equity is Better than Private Credit

(00:33:11) - Deal sizes for Preferred Equity

(00:39:20) - Common objections

(00:41:35) - Q&A

Opterra’s core investment strategies focus on both value-add (opportunistic) and stabilized, income-oriented assets in the hospitality, office and multi-family sectors. Our approach seeks to capitalize on mid-market opportunities in the $25 -150 million range in the United States, Canada, and the Carribean. Our investment strategy is strongly influenced by our deep asset management experience to identify the proper capital repositioning, cost reduction and operating leverage opportunities inherent in each asset to maximize returns to investors.

This episode was originally released July 2023

On this episode, Jake & Glenn discuss:

• Glenn's experience at Blackstone and it's influence on starting Opterra
• How they evaluate deals
• The 'no-assholes' policy
• Developing an asset management platform
• Acquisitions

Links:

Opterra Capital

Glenn on LinkedIn

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

Timecodes:

(00:00:00) - Intro

(00:01:01) Glenn’s career at Blackstone and the decision to leave

(00:06:39) Rolling the Blackstone mentality into Opterra

(00:08:09) Glenn on falling in love with Hospitality

(00:09:57) How Blackstone shaped Glenn’s Investment Perspective

(00:13:02) How Opterra evaluates deals

(00:16:54) Opterra’s capital strategy

(00:19:15) Converting Office into a Luxury Hotel

(00:23:49) Structuring a business to be focused on doing what you want to do

(00:26:35) The ‘no-assholes’ policy

(00:32:46) Post-Pandemic approach to doing deals

(00:34:29) Qualities behind great RE investors and asset managers

(00:39:01) Developing an asset management platform

(00:44:11) Implementing processes at Opterra

(00:49:19) Acquisitions processes

(00:57:49) Areas in Hospitality ripe for disruption

(01:04:56) How have the past 3 years informed your decisions for the next 5 years?

(01:09:58) How do you know when to sell?

(01:15:32) What’s your favorite hotel?

Links:

Aatmos

Mahavir on LinkedIn

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

(00:02:42) - Managing a lifestyle hotel with Marriott

(00:19:08) - Differences between Mom & Pop style hotels vs. major brands

(00:12:51) - The clash between old-school and new-school hospitality

(00:16:01) - What do most people underestimate about hospitality?

(00:19:55) - Converting a motel into a lifestyle hotel

(00:32:25) - What did you miss in this project?

(00:39:33) - F&B

(00:44:12) - What are you doing less of as you do these conversions?

(00:47:57) - The inspiration of Blackberry Farm

(00:52:04) - How do you make your sub-100-key hotels profitable?

(00:57:47) - The inn-keeper concept

(01:07:41) - Where do you want to be in 5 years?

(01:08:49) - What’s your favorite hotel?

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

Links:

Cyrus on LinkedIn

HWE

Topics:

(00:00:00) - Intro

(00:03:41) - Cyrus career in Hospitality brokerage

(00:10:22) - The growth around the Miami area

(00:12:58) - Hospitality brokers vs. other asset classes

(00:16:06) - Gauging the credibility of brokers

(00:19:18) - Broker stories

(00:21:08) - What’s the biggest difference between the blackstones and owner-operator groups?

(00:23:54) - Thoughts on the state of commodity hotels

(00:29:32) - Pivoting into ultra-luxury hospitality

(00:34:36) - What does Ultra luxury mean to you?

(00:36:42) - The importance of Brand

(00:39:39) - What insights have you gained in making an ultra-luxury property profitable?

(00:42:52) - Development approaches

(00:50:00) - Fund Structure

(00:53:07) - Planning and Hold timelines

(01:00:39) - How are ultra-luxury hotels making money?

(01:03:48) - Operations and management

(01:05:36) - Why would you pass on a deal?

(01:09:53) - Why is ultra luxury your best bet?

(01:15:38) - What is your favorite hotel?

Links:

Austin on LinkedIn

The Pacaso Backstory

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

(00:02:31) - Austin’s career in RE

(00:08:54) - Building DotLoop

(00:25:52) - Selling the business to Zillow

(00:28:33) - The future of RE agent commissions

(00:34:09) - Building Pacaso

(00:41:05) - Raising capital for the business

(00:48:43) - Revenue opportunities

(01:01:45) - Market selection

(01:05:18) - Master-plan resort communities

(01:10:48) - International markets

(01:14:12) - Most common objections 

(01:15:43) - Challenges in seasonal markets

(01:16:55) - Financing in a co-ownership structure

(01:18:42) - What is your favorite hotel?

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

Timestamps

(00:00:00) - Intro

(00:01:02) Why are we talking about Fees?

(00:03:39) Why GPs charge fees

(00:09:02) Deal shops vs. Real Estate Private Equity Firms

(00:10:23) Charging market fees to build great returns & borrowing costs

(00:14:45) Real Estate Operating Companies vs. Assets

(00:17:15) Understanding where your company is at in it’s life cycle

(00:18:42) Primary components and fees you’ll see

(00:20:04) What to charge for and include in fees

(00:22:10) Do not operate at a loss

(00:23:08) Project Management vs. Asset Management

(00:29:24) Final Thoughts

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?

Mr. Hehir received a Bachelor of Science Degree in Hotel Administration from Cornell University and a Diploma in Hotel Administration from the Hotel Institute Montreux, Switzerland.

On this episode, Sean and Jake discuss:

• Executing $500m of renovation projects
• Raising capital
• Fostering a no-asshole culture
• Strategies and deal criteria

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

Links:

Sean on LinkedIn

Trinity Investments

Topics:

(00:00:00) - Intro

(00:02:11) Sean’s journey from Botswana to the United States

(00:06:50) Influences on Sean’s investment decisions

(00:07:56) Where do you see hotel labor moving within the US?

(00:10:31) How did you learn to be an investor?

(00:13:49) Why drew you to hospitality?

(00:16:25) Does being in Hawaii make you feel left out?

(00:17:53) What trends are you focusing on now that will pay dividends in the next decade?

(00:22:10) Executing $500m of renovation projects

(00:26:02) Raising Capital

(00:27:48) Do you fear more pain in the hotel industry?

(00:29:39) Where will you be investing as we enter another cycle?

(00:31:18) Learnings from the GFC

(00:33:04) What is a GP fund?

(00:36:43) How do you go to major banks and borrow from them?

(00:39:57) How do you design your fee structure?

(00:40:55) What did you learn from the GFC that showed you the massive opportunity coming from Covid?

(00:45:41) How do you think about the enterprise value?

(00:48:16) Thoughts on WFH from a business owner perspective

(00:51:19) Fostering a no-asshole culture

(00:52:36) The process of raising funds

(00:59:28) How do you execute your business plan with an existing manager in place?

(01:02:18) How do 4 Seasons and Hilton differentiate in their focuses?

(01:04:07) Navigating luxury F&B and discussing deals

(01:12:05) Strategy and deal criteria

(01:12:08) Micro resorts

(01:25:23) What makes a great partner?

(01:29:00) What is your favorite hotel?

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

(00:02:32) - Introduction: The capital sitting on the sidelines & targeting family offices

(00:10:11) - Relationship building and finding deals

(00:17:13) - Growing your network

(00:26:09) - Overcoming challenges

(00:35:03) - Q&A

On this episode, Jake and Dev discuss:

• Growing up in the family hotel business
• How to build successful partnerships
• Creating long-term investment structures

Links:

Dev on LinkedIn

Merrimac Ventures

Six Senses Douro Valley

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

(00:02:00) - Dev’s upbringing and career in real estate and hospitality

(00:12:46) - Mentorship

(00:16:42) - Meeting Donald Trump

(00:19:10) - Acquiring a full city block of real estate

(00:21:24) - What asset classes were you working on outside of hotels early on in your career?

(00:24:19) - How did you raise capital on your first deal?

(00:28:15) - Key characteristics of land sites that make it work

(00:32:34) - Working with LPs

(00:37:01) - How are you structuring deals?

(00:39:35) - How are you unlocking liquidity as you begin working with family offices and high-net-worth individuals?

(00:41:39) - What are some of the mistakes you’ve made buying land?

(00:48:23) - How are you considering investing in other parts of FL?

(00:51:01) - Going into the Telluride market

(00:58:52) - Condo economics

(01:07:35) -Thoughts on shadow STRs

(01:10:28) - How to deal with challenging partnerships

(01:12:53) - What’s your favorite hotel?

On this episode, Jake and Rob discuss:

• How Lowe was able to build such a massive organization
• Converting Office to Residential
• Developing Hotel Properties
• Incentivizing teams and developing culture

Links:

Lowe - Beyond Buildings

Rob on LinkedIn

CoralTree Hospitality

Ivy Station in Culver City, CA

Terranea Resort in Palos Verdes, CA

La Coorniche Hotel, France

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Topics:

(00:00:00) - Intro

(00:02:36) - How did Lowe build such a massive footprint?

(00:10:04) - What were some early insights you had on the importance of people and place?

(00:14:23) - What are your thoughts on Office as an asset class?

(00:16:25) - Are you looking to convert any of your Office buildings?

(00:18:46) - What are some things you look for when determining if you can convert an Office to Residential?

(00:20:32) - Have you ever considered getting Hotel, Office, and Resi within one building?

(00:22:58) - How do your local teams integrate into the larger organization?

(00:24:02) - How do you capitalize your deals?

(00:25:06) - What’s been your experience working with your brother and how did you end up in the business?

(00:28:06) - Did you have any hotel experience before you stepped into the role?

(00:29:16) - Is developing hotels in today’s market more difficult?

(00:32:41) - Do you prefer to buy assets from a bank or to develop from the ground up?

(00:33:18) - Developing the Terranea hotel in California

(00:49:27) - How did you approach F&B at the property?

(00:51:02) - Thoughts on entitlement

(00:52:27) - How did Destination Collective come about?

(01:02:06) - Would you consider buying management companies with your new company?

(01:03:58) - What contracts are you looking for right now?

(01:05:20) - How do you think about incentivizing?

(01:08:45) - How much time do you spend developing culture?

(01:11:14) - What is your favorite hotel?

Before joining LaTerra, Mr. Tourtellotte spent 7 years at Prudential Global Investment Management (PGIM), a global real estate private equity investment fund manager with over $50 billion of gross assets under management. 

Links:

LaTerra: https://laterradev.com/

Chris on LinkedIn: https://www.linkedin.com/in/chris-tourtellotte-3257224/

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

(00:02:52) - Chris’ career and background

(00:10:58) - How are you dealing with institutions today?

(00:15:40) - Starting a self-storage vertical

(00:20:13) - What are institutional funds looking for from you?

(00:22:02) - How have you been able to get deals done in a reasonable timeline in a market like California?

(00:28:32) - How do you structure land deals and waterfalls?

(00:31:40) - What’s your hold period strategy?

(00:33:05) - Why is design so important to your deals?

(00:37:22) - What mistakes have you made in design or amenity?

(00:40:57) - Why did you add a construction component to your vertical?

(00:44:00) - What’s the best way to manage development and construction?

(00:51:21) - What’s surprised you most about your self-storage vertical?

(00:53:26) - What lessons from PE have you embedded into your business?

(00:58:17) - What are the biggest opportunities you’re seeing? 

(01:01:46) - Family dynamics in business

(01:06:04) - What would you like to be doing more of in 5 years?

(01:07:55) - What is your favorite hotel?

Bridgeton is dedicated to driving innovation in the hospitality industry and achieving this through expressive design, crafting unique experiences, and providing exceptional service. This steadfast commitment to delivering unmatched experiences extends to their partnerships with investors.

Links:

Bridgeton

Atit on LinkedIn

Marram Montauk

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

(00:02:32) - Atit’s portfolio and evolution in Hospitality

(00:06:28) - How do you think about scaling your business?

(00:10:07) - What mistakes did you make in your career you would encourage others to avoid?

(00:20:02) - How have the other assets in your portfolio helped the hospitality assets in your portfolio?

(00:24:06) - Transforming a motel into a valuable hospitality asset and selling it to PE

(00:30:38) - What mistakes have you made in Capex or renovation you learned a lot from?

(00:35:19) - Thoughts on seasonal properties

(00:37:52) - How do you deal with staffing in a seasonal environment?

(00:39:35) - How are you underwriting properties?

(00:45:27) - What are the key components that are non-negotiables in your properties?

(00:54:54) - How do you approach design?

(01:08:13) - How do you approach F&B?

(01:13:09) - What’s an idea you really want to do?

(01:15:35) - What’s your favorite hotel?

Links:

CT Realty Trust

Bard on LinkedIn

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

(00:02:32)- Bard’s first real estate deal

(00:13:15) - Creating a management platform

(00:16:43) - How have you built an edge over others in your industry?

(00:20:58) - When buying a cheap asset, what’s more indicative of success: the market or the bones of the building?

(00:23:21) - How do you identify markets to enter?

(00:31:30) - What opportunity are you seeing in Build for Rent communities?

(00:51:15) - What tips and tricks have you learned about renovations?

(00:56:03) - What leads you to a fast ‘no’?

(01:08:05) - How are you capitalizing deals?

(01:12:32) - What have you changed in your deal strategies?- 

(01:19:31) - What’s your favorite hotel?  

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

(00:01:24) - Buying a piece of land & raising money

(00:10:07) - Second round raise strategies

(00:14:30) - What to do when you don’t want to take the risk on a piece of land

(00:19:10) - Co-GP options

(00:25:47) - Development risk

(00:27:17) - Q&A

(00:27:53) - Underwriting

(00:32:12) - RevPar Trends

(00:41:20) - Underwriting based on future-development vs. existing development

(00:48:12) - Does experience stay work in any market?

(00:54:02) - Cash on Cash return expectations in today’s market

(00:56:37) - GP economics vs. LP economics

Disclaimer: This content is intended for entertainment purposes only. This is not financial or investing advice and should not be considered as such.

Prior to launching Torose, Scott co-founded Tricera Capital where he led the charge on strategic direction, capital markets and sourcing investment opportunities. In this role, Scott built a portfolio in excess of $700M over five years and consistently delivered returns in excess of 20% IRR and a 2x multiple across realized investments. Scott maintains ownership and major decisions across the Tricera portfolio and continues to be a minority owner of Tricera Capital.

Torose Equities is a Miami-based real estate investment firm with several different verticals, including a value-add urban retail, office, and mixed-use strategy within the Southeastern United States.

This episode was originally released September 2023

On this episode, Jake & Scott discuss:

• Important retail trends that will shape the next decade
• The science of placemaking
• The opportunity for Office
• Working with Family Office Investors
• Building Torose Equities

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

Links:

Torose Equities

Scott on LinkedIn

Assembly Row Boston

Ennet Perry Cabin

Topics:

(00:00:00) - Intro

(00:01:40) Scott’s background and career

(00:10:37) Learnings from working in international markets

(00:13:16) How are you choosing what markets to choose on now?

(00:15:14) Risk and reward in investing

(00:17:57) What is your competitive edge?

(00:19:12) What are some important retail trends that will shape the industry over the next decade?

(00:21:40) What’s important for Office investors over the next 5-10 years?

(00:27:40) Pros and Cons of Commercial and Retail Investing

(00:29:38) Placemaking

(00:36:40) What do you look for in locations for the success of retail?

(00:39:47) What is the opportunity for Office in Florida?

(00:42:32) Developing a 350k sqft covered land play

(00:48:18) How are you finding Family Office investors?

(00:49:17) Co-GP opportunities

(00:50:14) Characteristics of good partners

(00:51:26) Building Torose Equities

(01:01:16) How are you sourcing deals?

(01:05:06) What’s your approach to value-add?

(01:09:11) What processes have you implemented in your company?

(01:11:33) What is your favorite hotel?

Today, Roundhouse focuses exclusively on providing high-quality housing options in emerging cities across the Western United States. In order to deliver superior experiences to our employees and residents we have built a fully integrated service offering that spans the construction, property management, and design disciplines.

On this episode, Jake & Casey discuss:

• Learning to structure long-term horizon deals
• Avoiding competing with institutional capital
• Structuring deals for acquisitions vs. developments
• The advantages of being vertically integrated -
• Casey's 6-month sabbatical and how to have your company be successful without you

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 

Links: 

Roundhouse: https://rndhouse.com/

Casey on Twitter: https://twitter.com/roundhouse208

Topics:

(00:02:18) Casey’s RE Career in Southern California

(00:11:40) The decision to pivot out of LA

(00:15:54) Learning to structure long-term horizon deals

(00:18:41) How do you avoid competing with institutional capital?

(00:22:04) How have you figured out how to raise enough capital without going to someone with deeper pockets?

(00:24:41) How do you structure deals when they are acquisitions vs. developments?

(00:31:08) How often are you refinancing in order to return capital?

(00:35:48) How do you think about Capex in multifamily over long hold periods?

(00:43:38) How are you differentiating your high-end products?

(00:47:00) What are the advantages of being vertically integrated?

(00:50:59) What does enterprise value mean to you?

(00:57:53) Are you at a point where the team can raise capital without you?

(01:02:28) What was the scenario that led to you buying out your partner?

(01:07:51) How do you ensure leadership values are being replicated across the business?

(01:11:29) What was the biggest insight you gained from your 6-month sabbatical

(01:19:44) Casey’s emphasis on design

(01:22:18) What is your favorite hotel?

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/

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?

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

As CEO of Moss, Scott inspires and empowers his team to create the exceptional. His innate curiosity drives a culture of continuous learning where insight, engagement, and determination define an individual’s success. 

Links:

Scott on LinkedIn

Moss Construction

The Palace in St. Moritz

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Topics:

(00:00:00) - Intro

(00:02:50) - Scott’s career in construction

(00:12:56) - Do you set goals every year or every 5 years?

(00:13:50) - How has the construction market changed over the past 10 years?

(00:16:21) - Are you seeing non-diversified companies go under?

(00:17:44) - How do you select new markets?

(00:20:51) - How do you think your customers view your company?

(00:23:19) - What are some mistakes you see developers make?

(00:27:40) - When should people start the conversation with their General Contractor?

(00:29:53) - What are your first steps when you begin a project?

(00:33:19) - When a market is lacking sub-contractors, do you ever bring in subs from out of the market?

(00:34:48) - What’s changed in your strategy over the past 5 years?

(00:37:53) - How do public and private jobs differ?

(00:41:23) - Scott’s Vision Leadership Council

(00:48:38) - Can you repair trust once it's broken?

(00:50:24) - How do you view your role with regard to this council?

(00:51:32) - How do you ensure your culture scales with the company's growth?

(00:56:59) - What meetings are you attending that help you keep a pulse on the business?

(01:01:18) - Where is most of your energy spent on a weekly basis?

(01:04:13) - What are your goals for the solar side of the business?

(01:06:04) - How much does China impact the future of your business?

(01:09:40) - Are you seeing any major shift in your industry right now?

(01:15:23) - How are you building Moss to be a generational business?

(01:21:32) - What is your favorite hotel?

The younger Cobb became a lawyer and cannabis lobbyist before founding his own marijuana company, Bluma Wellness, which he sold in April 2021 to Cresco for $213 million in an all-stock deal. In November 2022, Cobb took his father's rich history of smuggling and launched Sunburn in Florida, a vertically integrated dispensary chain with nine retail shops.

Sunburn is the 13th largest medical marijuana company in Florida, the company is valued at $105 million and will generate around $50 million in revenue by the end of its first year in operation.

Links:

Sunburn Cannabis

Brady on Instagram 

Lefay Resorts Italy 

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

(00:01:52) - From Law to Cannabis: Brady Cobb's Entrepreneurial Journey

(00:02:37) - The Legacy of a Cannabis Smuggler: Brady Cobb's Inspirational Backstory

(00:06:23) - Navigating the Complex World of Cannabis Business

(00:13:31) - The Evolution of Cannabis Legislation and Its Impact on Business

(00:26:26) - Inside the Operations: The Challenges of Running a Cannabis Company

(00:31:14) - Understanding Cannabis: From Farming to Market Dynamics

(00:37:58) - CBD vs. THC: Demystifying Cannabis Components

(00:40:24) - Exploring the Complex World of Cannabis

(00:41:35) - Personal Anecdotes and Preferences in Cannabis Consumption

(00:42:10) - Innovations and Partnerships in Cannabis Beverages

(00:44:28) - The Significance of Culture and Community in Business

(00:48:27) - Security Challenges and HR in the Cannabis Industry

(00:59:17) - Building a Brand and Raising Capital in Cannabis

(01:14:23) - Future Aspirations and Closing Thoughts

On this episode, Jake and Matt discuss:

- A walkthrough of converting an independent hotel in Hawaii

- Developing Investor Relations

- Growing and evolving a Management Company

- Key to differentiating the hotel experience

Links:

PacificaHotels.com

Matt on Instagram

King Kamehameha's Kona Beach Hotel

Hotel Bel Air

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Topics:

(00:00:00) - Intro

(00:02:07) - Matt’s career background

(000:07:46) - What did you do within the hotel asset that made you so successful?

(00:08:50- What did you come to be known for?

(00:10:00) - What was so appealing about doing deals in California?

(00:11:24)- How would you describe your portfolio in 2023?

(00:12:51)- Converting an independent hotel

(00:19:46) - Selling an Asset to Blackstone

(00:23:41) - How do you think about taking a profit?

(00:29:33) - What happens when you have a ReFi?

(00:32:57) - Do you readjust your holding patterns when working with Institutional Capital?

(00:36:25) - What have you learned about Investor Relations?

(00:39:52) - Where do you find investors now?

(00:41:07) - What pillars won’t you move on in negotiating with investors?

(00:42:18) - What was it like being managed by Blackstone?

(00:44:52) - What’s the process of creating a Hotel Brand?

(00:50:20) - Is there a certain size hotel where the amenities become challenging?

(00:53:18) - Are there simply too few deals out there?

(00:54:16) - Is it unsettling having all this dry powder on the sidelines?

(00:55:46) - How has your management company evolved over the years?

(00:57:42) - What key things do you focus on to differentiate the hotel experience?

(01:03:18) - How do you think about preparing your business for the next generation?

(01:07:26) - How are you growing the management company?

(01:09:54) - What is your favorite hotel?

(01:14:46) - Where can people find you online?

This is a replay of the well-received episode #2 of Masters of Moments where Marc & Rose was known as Classic Hotels & Resorts.

In this episode, we discuss:

- Sourcing deals & developing strategy

- Leading an operating team & executing on a vision

- Hospitality trends over the next decade

John Grossman:

Marc & Rose - https://marcandrosehospitality.com/

Grossman Company Properties - https://www.grossmancompany.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

(00:03:30) - Introducing John & his portfolio

(00:05:55) - What is it about leisure and independent hotels that is attractive to you?

(00:07:40) - How have you avoided the franchising model after all these years?

(00:09:12) - How do you approach the infrastructure of your organization?

(00:09:59) - Why are folks who’ve come from places like Ritz Carlton and 4 Seasons a great fit for you?

(00:11:40) - What are your criteria when you’ve found a market you like?

(00:15:15) - How are you finding these properties when there are moratoriums on hotel doors?

(00:18:42) - How do you plan out how each hotel will look once you’ve acquired an asset?

(00:21:17) - How do you underwrite your deals?

(00:26:43) - How do you think about who the guest is going to be?

(00:29:18) - Who handles the design for your hotels?

(00:32:56) - What are you prioritizing as you set your budget?

 (00:36:36) - What makes the best designers truly great?

(00:39:42) - Are you prioritizing public spaces over guest room decisions?

(00:43:01) - How are you creating “Moments” without focusing on the F&B side of the property?

(00:45:36) - Is there a variable when you’re analyzing a new investment some would find surprising?

(00:50:37) - Is being vertically integrated your best competitive advantage?

(00:53:39) - How involved are you in setting the mold of the brand narrative for the designers?

(00:57:22) - What are the big trends that you’re thinking about over the next 5 years?

(01:03:18) - What is your favorite hotel?

Links:

Woodbine Development

Dupree on LinkedIn

Hotel Emma - San Antonio

Mountain Shadows Resort Scottsdale

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Topics:

(2:48) - Woodbine’s history and path to success

(10:06) - How have you diversified Woodbine’s capital partners?

(13:18) - What led to Woodbine focusing on hospitality?

(17:49) - How do you make money on a shorter time horizon when you have a partner thinking 3-4 generations down the road?

(20:36) - What do you find is the most important aspect of being able to secure a deal?

(23:32) - How did you get into the business?

(26:05) - What’s the hardest thing stepping into the business as the second generation?

(32:09) - What are some key learnings you had from your time with Trammell Crow?

(35:09) - How do you get the most bang for your buck in projects?

(37:31) - Are there aspects of a project you refuse to compromise?

(38:30) - How do you create a moment and a place where guests want to be?

(42:12) - How did the Driscoll Hotel and Hyatt Hillcountry deals come together?

(50:37) - How do you approach raising capital for deals?

(54:56) - What is it about hotels that you and your investors are attracted to?

(57:31) - What did the capital stack for The Driscoll look like?

(1:00:27) - Do you manage the hotels yourself or do you 3rd party it?

(1:03:13) - How do you align F&B with your vision?

(1:04:47) - Do you have any tips or strategies for structuring F&B deals?

(1:06:02) - Is it not possible to build a mega-resort anymore?

(1:08:15) - What do you think about 3rd party development?

(1:11:22) - What criteria are you focusing on in development deals right now?

(1:12:16) - Why are you diversifying your assets beyond hospitality?

(1:15:53) - What do you think happens to certain assets in Office?

(1:17:36) - What is your favorite Hotel?

Disclaimer: This episode is not an endorsement of Ben's deal or to aid in raising money for Ben's deal, it is opinion only and purely for informational and entertainment purposes.

Links:

Ben on Twitter: https://twitter.com/uniquestaysguy

Ben on LinkedIn: https://www.linkedin.com/in/ben-wolff/

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

(00:03:08) - The purpose of the call

(00:05:00) - Introducing Charles & Dovehill’s objectives when looking at deals

(00:08:21) - Introducing Ben and initial deal reaction/feedback

(00:27:20) - Feedback on financials & capital stack

(00:37:31) - Performance metrics

(00:39:22) - The operating model and F&B

(00:57:08) - More feedback on performance metrics

(01:00:38) - Q&A

(01:10:00) - Waterfall structure

(01:11:41) - Wrap up

John is also the Founder, Chairman, and CEO of its primary hotel operating affiliate, Oxford Hotels and Resorts, LLC., which specializes in operating, managing, and branding distinctive, high-design luxury lifestyle hotels and food & beverage venues including its proprietary lifestyle hospitality brands: Godfrey, LondonHouse, Julian, IO, ALK, SOMA House, Fiona, and Garrett

On this episode, Jake and John discuss:

- Navigating economic black swan events

- How John Built Oxford Capital Group

- How Oxford operates in the luxury lifestyle hotel space

Links:

Oxford Capital Group, LLC - https://www.oxford-capital.com/

Oxford Hotels & Resorts, LLC - https://ohrllc.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

(00:02:32) - John’s RE career

(00:08:05) - European mindsets in RE investing

(00:16:53) - Black Swan event insights

(00:31:16) - How are you thinking about making investments in markets that might be suffering politically in the short term?

(00:44:51) - Building Luxury-lifestyle brands

(00:51:04) - F&B mistakes

(00:56:44) - The London House Chicago

(01:05:39) - How do you reconcile challenges with losing management contracts or an investor’s desire to sell?

(01:10:16) - How do you structure the organization?

(01:12:46) - Are you opportunistic or strategy-driven?

(01:15:39) - What are some key learnings from building this company?

(01:21:50) - What is your favorite hotel?

On this episode, Jake and Greg discuss:

• How to identify A-Players
• The best way to comp people in REPE
• Organization-defining deals
• Capital structures

Links:

BH3 Management

Greg on LinkedIn

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

(00:02:48) - Greg’s career and background

(00:14:41) - How to identify A-players

(00:16:43) - What’s the best way to comp people in REPE?

(00:19:47) - Recruiting talent

(00:23:20) - Being both entrepreneurial and institutional

(00:28:40) - Organization-defining deals

(00:41:10) - The world of South Florida condo development 

(01:00:26) - Developing relationships

(01:05:00) - Capitalizing deals

(01:17:34) - Waterfall structures

(01:22:16) - Buying debt

(01:27:41) - What is your favorite hotel?

JRNY is a Canadian whisky created by the Brothers Sean and Chris Pronger with award-winning distillery Niagara Falls Craft Distillers Whisky. 

On this episode, Jake and Chris discuss:

- Life in the NHL, mistakes, and lessons learned

- Developing a professional mindset in athletics and business

- Launching JRNY and competing in the beverage market

Check out JRNY here: https://jrnyspirits.com/

Topics:

(00:00:00) - Intro

(00:04:34) - How youth sports have changed

(00:09:44) - Developing a professional mindset in athletics

(00:12:01) - Misconceptions about leadership in pro sports

(00:14:36) - What it takes to play 19 years in the NHL

(00:16:37) - Transitioning back to civilian life

(00:19:18) - Mentors & investing

(00:33:32) - Discovering yourself after retiring

(00:39:27) - Launching a whiskey brand

(00:52:02) - Bouncing back from failure

(00:53:24) - How to pick great partners in business

(00:58:51) - Competitive advantages

(01:01:17) - Brand inspirations

(01:06:32) - Building relationships

(01:08:57) - Chris’ real estate strategy & career reflections

(01:24:56) - What is your favorite hotel?

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

On this episode, Jake and Mark discuss:

• Building DiamondRock
• Mark's approach to hotel real estate investing
• Operating investing teams
• Acquisition methods

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

Links:

DiamondRock Hospitality

Topics:

(00:00:00) - Intro

(00:04:00) - The importance of relationships

(00:08:18) - Transitioning from residential to hospitality

(00:10:56) - Law school as a path to success in RE

(00:12:50) - What makes a successful broker

(00:14:39) - Learning from working at Marriott

(00:18:24) - Hiring effectively

(00:21:07) - Moving away from the brand business

(00:25:09) - How Mark thinks about investing in Hotel RE

(00:34:24) - Pivoting to Leisure

(00:37:13) - Off-market transactions as a public company

(00:41:24) - Is there a blank space in hospitality that’s interesting?

(00:42:25) - Challenges in remote acquisitions

(00:47:22) - Hiring management

(00:51:34) - How to successfully oversee a portfolio of properties

(00:55:52) - Macro-economic concerns

(00:59:55) - The future of hospitality

(01:01:59) - Transitioning to soft-brands

(01:03:21) - Operating Investment teams

(01:04:27) - Approach to acquisitions

(01:09:49) - What would you like to do more of in your role?

(01:10:57) - What is your favorite hotel?

On this episode, Jake and Isaac discuss:

• Building and Selling Live Oak Lake
• What's next for Isaac
• Naivety as an advantage

Links:

Isaac on X

Experiential Hospitality

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

(00:02:19) - The Nook

(00:10:21) - Landscape hotels

(00:14:47) - Getting into the hospitality business

(00:21:44) - Building Live Oak Lake

(00:44:57) - The numbers behind Live Oak Lake

(01:04:02) - Selling Live Oak Lake

(01:11:56) - What’s next?

(01:26:12) - Naivety as an advantage

(01:30:50) - What is your favorite hotel?

Their brands, development, and operational expertise also include specialized retail spaces, highly curated restaurants, bars, and event venues. 

Avi Brosh founded Paligroup in 1998 and serves as its Chief Executive and President.

On this episode, Jake and Avi discuss:

- Avi's career in hospitality

- Pali's approach to design and placemaking

- How to enter new markets

- How to excel at Food and Beverage

Links:

Palisociety - https://www.palisociety.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

(00:02:52) - Avi’s background and career

(00:12:23) - Avi’s approach to placemaking

(00:13:49) - Where do you draw inspiration?

(00:16:20) - Creating a hub for both locals and transients

(00:18:27) - Transitioning from residential to hospitality

(00:23:38) - What were your non-negotiables when starting your own company?

(00:26:41) - How are you able to maintain a fresh feel with each new project while keeping a brand theme?

(00:32:26) - Walkthrough of a typical project

(00:37:11) - What does it mean to have a brand?

(00:41:25) - What mistakes did you make early on and what components matter?

(00:48:32) - How have you been able to make good returns on your investments?

(00:52:15) - What have you learned about making the operating business profitable?

(00:54:55) - What’s been the hardest part about growing the brand?

(00:58:54) - What do you look for in a new market?

(01:04:11) - How do you find the right people to help bring these projects to life?

(01:10:40) - What works in Food and Beverage?

(01:17:00) - How do you decide to pivot if a restaurant isn’t working?

(01:19:47) - What are you looking to get into that you aren’t already?

(01:27:23) - Navigating owner/partner visions

(01:31:30) - What is your favorite hotel?

On this episode, Jake and Sieva discuss:

• Pivoting from being an operator to an investor
• Due diligence on potential acquisitions
• How to incentivize management teams and CEOs
• How Enduring integrates into an acquired company

Links:

Sieva on X

Enduring Ventures

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

(00:03:33) - What is a holdco and why are they so popular?

(00:07:20) - Sieva’s focus on private companies

(00:14:54) - Pivoting from being an operator to an investor

(00:17:13) - Starting Enduring

(00:20:41) - How did you make UpCouncil a profitable business?

(00:23:52) - VC Turnaround work

(00:26:58) - What kind of due diligence are you doing to get you to a quick yes or no?

(00:30:56) - How do you interview management teams to determine if they will stick around?

(00:37:16) - What’s the best way to incentivize CEOs?

(00:39:18) - What’s the best way to integrate Enduring into an acquisition?

(00:46:10) - How do you keep a pulse on all 21 companies within Enduring?

(00:49:13) - Are there any outstanding ideas or processes from a CEO within Enduring that you wanted to apply to all the companies?

(00:54:20) - Do you get more energy from finding deals or making an acquisition flourish?

(00:58:54) - Acquiring platforms vs. businesses

(01:03:17) - The Enduring Ventures organizational structure

(01:15:10) - Finding the balance for doing what’s best for an individual business and the portfolio

(01:16:31) - How does the financing for doing a deal work?

(01:27:10) - What scares you most about growing a business?

(01:30:05) - What is your favorite hotel?

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 Twitter: https://twitter.com/jwurzak

Take the Hospitality Investing Masterclass: https://learn.jakewurzak.com/

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?

On this episode, Jake and Brian discuss:

- Growing the family business to over $100M

- The reality of Private Equity

- Advice to early career folks

- The 101 of what makes a great alcohol brand

Links:

Brian on LinkedIn - https://www.linkedin.com/in/briandavidrosen/

InvestBev - https://www.investbev.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

(00:04:25) - Brian’s family legacy in the beverage business

(00:08:15) - Taking the business to $100 million

(00:10:39) - The struggles of joining a family business as the 3rd generation

(00:24:20) - Selling the business to Private Equity and buying out the rest of the family

(00:25:28) - Operating in a highly regulated environment

(00:26:23) - Life under PE

(00:30:47) - Advice to early career folks

(00:32:47) - How the liquor business has changed

(00:36:55) - Buying back the business

(00:39:45) - InvestBev

(00:41:16) - Titos: How does an overnight success take 20 years?

(00:43:27) - The power of celebrity marketing in new beverage brands

(00:49:10) - How do you approach investing in brands?

(00:52:52) - Do you consider incubating your own brands?

(00:57:00) - The distillery world

(01:01:11) - Optimal hold periods of brands

(01:02:34) - Raising a fund

(01:12:48) - Advice for those looking to overcome a challenge in their track record

(01:15:43) - How has your fund structure changed now that you’re on your fifth?

(01:17:34) - What’s your competitive edge?

(01:20:33) - How big is the cannabis-beverage market?

(01:22:32) - What would you have preferred to do more or less of in your career?

(01:25:00) - 3 year goals

(01:28:48) - What’s your favorite hotel?

I discuss:

(00:00:00) - Intro

(00:04:34) - Promoted Interest

(00:06:00) - What’s a waterfall?

(00:08:28) - How to build a waterfall

(00:15:04) - Advanced structures

(00:18:59) - Nuances

(00:26:44) - Crystallization

(00:30:06) - How we structure our deals

(00:34:34) - Mistakes we’ve made

(00:38:11) - Q&A

Links:

Join the Community

The Boardroom

Casey Lynch on Masters of Moments

Ben Wolff on Masters of Moments

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

MRP Capital Group is The nation's largest owner of Walmart Shadow Centers in small-town America. Their current portfolio is comprised of nearly 2.6 million square feet across 100 properties in 26 states.

On this episode, Jake and Jordan discuss:

• What makes a great Shadow Strip Center
• MRP's portfolio and transaction activity
• Optimizing the acquisition process
• Developing the right culture at your company
• Raising capital

Links:

MRP Capital Group

Jordan on LinkedIn

Placer.ai

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

(00:03:46) - Jordan’s experience building a real estate company

(00:08:25) - Why most folks don’t transition from being a deal shop into a real estate investment firm

(00:10:35) - Shadowing Walmart strip centers

(00:14:35) - What makes a great shadow strip center?

(00:17:34) - Where have you found ways to gain a competitive advantage?

(00:22:48) - Jordan’s portfolio and transaction activity

(00:25:18) - Defining the criteria for a deal

(00:31:27) - The purpose of capping the number of retailers

(00:33:06) - New Supply 

(00:38:42) - Optimizing the acquisition process

(00:42:51) - What are your long-term goals for the business?

(00:46:27) - Why a REIT would be interested in something as complicated as these deals

(00:50:28) - What strategies are you identifying right now?

(00:59:04) - Mistakes made

(01:05:37) - How to develop the right culture at your company

(01:15:45) - Raising Capital

(01:26:45) - What’s your favorite hotel?

In 2017 Mario co-founded Affordable Upsate, a small real estate investment firm, at the time with 63 units, that redevelops energy-efficient, multifamily apartment units. Since 2017 we have placed over $50MM of investor equity into socially responsible, environmentally-enhanced workforce housing investments.

On this episode, Mario and Jake discuss:

• The housing shortage in the southeast
• Mario's work in affordable housing
• Building a vertically integrated company
• Raising capital & deal structures

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

Links:

Affordable Upstate

Mario on LinkedIn

Topics:

(00:00:00) - Intro

(00:03:51) - Greenville: The new Austin?

(00:06:57) - The housing shortage in the southeastern United States

(00:13:22) - The opportunity in Class B multifamily

(00:16:09) - Mario’s work in affordable housing

(00:20:47) - How are you assessing risk?

(00:25:47) - Mario’s journey into real estate

(00:28:10) - What advantage do you have investing in the market you live in vs. outsiders?

(00:29:36) - Making the entrepreneurial leap

(00:37:23) - Mario’s first deal

(00:41:36) - Value add

(00:43:07) - Becoming vertically integrated

(00:46:09) - What innovative ways have you chosen to run the operating business?

(00:49:56) - What’s a mistake you made when building the PM company?

(00:52:12) - Investing through Gps & building trust with investors

(00:55:41) - Deal structures

(00:57:56) - Raising capital

(01:01:30) - What is your competitive edge?

(01:03:31) - Construction & renovations

(01:08:48) - What’s your weekly work cadence?

(01:10:43) - What drains your energy?

(01:11:43) - What are your 3-year goals?

(01:14:00) - What is your favorite hotel?

This is a time when you can earn equity-like returns with debt-like risk. 

They don't come often.

On this episode, I do a solo-deep dive on Pref Equity and some Q&A done with a live audience! Enjoy.

Links:

Deal Reward Program

Hospitality Investing Masterclass

Follow Jake on X

Topics:

(00:00:00) - Intro

(00:02:32) - Explaining Preferred Equity

(00:05:27) - Pref equity vs. mezzanine financing

(00:11:27) - Asymmetric returns

(00:13:49) - An example of using Pref Equity

(00:18:39) - Uses for Pref Equity

(00:22:33) - What Pref Equity is NOT used for

(00:24:23) - Where the magic happens: Structuring a Pref Equity deal

(00:37:49) - The Hospitality Investing Masterclass & Deal Rewards Program

(00:39:16) - Audience Q&A

The Company currently owns assets in North America, Latin America, Mexico and the South Pacific. The Canyon Group’s resorts are managed by marquis brands such as Amanresorts, Six Senses, Four Seasons Hotels & Resorts and Hyatt Hotels and Resorts. Under Vazifdar’s leadership, many of the Canyon Group’s ultra-luxury assets have achieved high global accolades and are considered the “Best in Class” with extraordinarily high occupancies and rates.

On this episode, Jake and Homi discuss:

- Selling a brand for $2m per key

- Building Amangiri and Amangani

- How to make experiential luxury work

- How to make select service hotels work

Links:

Canyon

Homi on LinkedIn

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

(00:01:19) Homi’s journey into Real Estate and hospitality

(00:07:08) What is most important when you are reinventing yourself?

(00:08:08) Building Canyon and the focus on ultra-luxury assets

(00:27:50) Swapping federally controlled land and creating a profitable asset in remote Utah

(00:48:13) How do you make a tent experience work?

(00:54:10) How do you find labor and built infrastructure in these remote areas?

(00:57:47) Is establishing a sense of community at a resort important?

(01:03:32) How have you learned to invest and stay afloat during cycles?

(01:12:36) What will be the biggest challenge in replicating this new concept?

(01:14:35) Homi’s select service hotel

(01:20:49) What is your favorite hotel?

Prior to Onera, Ben grew Blink Hospitality a short-term rental (STR) management company from 8 to 200 units under management in 18 months. He is a McKinsey alum and his first business was an events & promotions company in college. Ben is also an avid golf tourist and is on a mission to play all top 100 courses in the world.

On this episode, Jake and Ben discuss: 

- Utilizing overseas talent

- Walkthrough of a development

- Building Onera

- Fundraising

- Utilizing social media and influencer marketing

Links:

Ben on Twitter - https://twitter.com/uniquestaysguy

Ben on Substack - https://stayoasi.ck.page/newsletter

Stay Onera - https://stayonera.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:

The intersection of Tech and Real Estate & Ben’s career

(00:02:26) - Is there a flaw with urban short-term rentals?

(00:08:53) - Being lean vs. skimping

(00:13:14) - How to utilize overseas talent for hospitality

(00:15:46) - Creating moments with limited on-site staff

(00:18:32) - What are the biggest opportunities you see right now in the industry?

(00:20:19) - How has the modern traveler changed?

(00:21:50) - A la carte housekeeping services

(00:24:15) - Onera’s thesis

(00:31:17) - Walking through a development

(00:44:48) - How do you think about scaling?

(00:46:43) - Utilizing influencer marketing and social media

(00:53:17) - The importance of emphasizing direct booking

(00:58:27) - Ben’s plans for a jungle landscape concept

(00:59:56) - What inspires you for design?

(01:00:54) - What are you targeting from a cost, basis, and yield standpoint on a property?

(01:02:49) - What are the biggest risks to your margins as you grow?

(01:04:48) - Raising capital

(01:07:33) - The Spirit of Sophia Hotel

(01:10:00) - How’d you get a REIT to enter this asset class?

(01:16:23) - Where do you see booking going in the future?

(01:18:17) - What are the most common mistakes you see in this industry?

(01:19:47) - DIY hacks

(01:24:27) - What is your favorite hotel?

On this episode, Jake and Trevor discuss:

- The importance of a company mission

- Investing in Farmland

- Deal structures

- Raising Capital

- The importance of mentorship

Links:

Macfarlan Capital Partners

Trevor on Twitter

Trevor on Substack

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

(00:02:07) - The impact of the Military on Trevor’s career

(00:08:41) - The importance of a company having a Mission

(00:10:53) - Choosing real estate as a career

(00:18:17) - Lessons learned from the GFC

(00:20:46) - Can you create generational wealth without significant leverage?

(00:24:02) - Investing in Farmland

(00:32:25) - The value of experience in RE

(00:39:52) - Finding great operators

(00:42:19) - Deal structures on Farmland acquisitions

(00:49:25) - Crop share vs. lease models

(00:51:15) - What’s surprised you most in doing due diligence on a farm deal?

(00:53:27) - What does value-add look like in this asset class?

(00:56:56) - Where have you seen things go wrong in your acquisition process?

(00:58:52) - How are you fundraising?

(01:00:06) - The experience of working in a father-son business

(01:05:13) - The importance of reputation

(01:13:41) - Mentorship

(01:07:14) - What is your favorite hotel?

Formed in 2012 as an independent company, the firm carries in its DNA the successful 50-year track record of acquiring and operating multi-tenant commercial real estate assets of Matthew Adler’s legacy family business, the Adler Group.

On this episode, Jake and Matt discuss:

- How the fund investing model has changed risk appetite

- Adding value as an operator

- Matt’s investment strategy

- Creating incentives and deal structures

- Surviving without a promote

- Raising capital

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

Links:

Adler Real Estate Partners

Solo Ep on fees

Four Seasons Golden Triangle Thailand

Topics:

(00:00:00) - Intro

(00:02:00) - The post-covid industrial space

(00:05:02) - Key moments in Matt’s career

(00:08:40) - Gross-to-Net spread

(00:09:59) - How the fund investing model has changed risk appetite

(00:14:11) - Adding value as an operator

(00:16:54) - Matt’s investment strategy

(00:26:10) - Creating incentives and deal structures

(00:38:05) - Surviving without a promote

(00:42:29) - Raising capital

(00:50:34) - Characteristics of a successful reporting memo

(00:53:43) - Managing the business weekly

(00:57:13) - Acquisitions people vs. asset managers

(01:02:12) - The 3 KPI’s that determine whether to pursue a deal

(01:06:57) - Acquisitions and investment size

(01:09:24) - Sourcing deals

(01:11:54) - Thoughts on debt

(01:13:35) - What’s your favorite hotel?

Jake and Sky discuss:

- The state of experiential travel

- Finding great locations

- A walkthrough of a deal

- Nordic spas

- Advice for folks in hospitality

Links:

Basecamp Resorts

Sky on LinkedIn

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

(00:02:30) - Sky’s career and the Airbnb experience

(00:16:30) - The state of Basecamp today

(00:19:37) - Balancing chasing easier opportunities in real estate and complex hospitality projects

(00:22:02) - Finding good locations

(00:23:12) - The change in experiential travel

(00:24:43) - How are you capitalizing and structuring deals?

(00:33:51) - Sky’s competitive edge

(00:36:49) - How to know if you can make a property work

(00:38:17) - Spending money on things a guest sees vs. things they won’t see

(00:39:27) - F&B

(00:41:24) - Walkthrough of a deal

(00:52:14) - How do you approach design?

(00:55:14) - Nordic spas

(00:58:37) - Townhouse-hotels & alternative lodging

(01:02:41) - Sky’s worst deal

(01:04:53) - Advice for folks in hospitality

(01:06:23) - Building culture

(01:09:29) - What is your favorite hotel?

On this episode, Jake and Jonathan discuss:

• Finding and structuring deals
• Gauging risk
• Debt strategies
• Rate ceilings
• Strategy sessions
• Building a vertically integrated organization
• Setting incentives

Links:

EOS Investors

Jonathan on LinkedIn

Girls Like Us by Cristina Alger

The Great Game of Business by Jack Stack

Isla Bella Beach Resort

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

(00:02:01) - Jonathan’s career hospitality

(00:05:52) - How are you finding and structuring deals?

(00:10:05) - Gauging risk

(00:14:18) - Succeeding in hospitality as an outsider

(00:20:46) - Debt strategies

(00:25:51) - Evaluating market supply

(00:28:12) - Rate ceilings

(00:31:50) - Why Jonathan chose hospitality

(00:33:49) - Most important learnings about hospitality

(00:37:49) - Rationalizing having a diverse portfolio

(00:45:06) - Strategy Sessions

(00:50:15) - Improving communication flows

(00:57:20) - Building a vertically integrated organization

(01:03:17) - Building EOS(?)

(01:09:01) - Incentivizing people

(01:14:38) - Where investments go wrong

(01:17:13) - What is your favorite hotel?

On this episode, Jake and Noah discuss:

- Spotting patterns in cycles to take advantage of

- Debt positioning

- Identifying great locations

- Biggest makes for folks getting into the land business

Links:

BTI Partners: https://btipartners.com/

Noah on LinkedIn: https://www.linkedin.com/in/noah-breakstone-97ba576/

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

(00:01:41) - Noah’s background and career in development

(00:11:31) - Spotting patterns in cycles to take advantage of

(00:14:43) - Hold periods and investment horizons

(00:17:02) - Asset class approach

(00:22:53) - Debt positioning

(00:25:49) - Finding the right partners

(00:27:51) - Why did you choose to only operate in Florida?

(00:31:02) - Identifying a great location

(00:32:50) - Long-term concerns for Florida

(00:35:37) - Build for Rent opportunities

(00:41:28) - Does education play a role when looking at land?

(00:44:34) - Housing

(00:56:30) - The impact of distribution centers

(00:59:28) - Biggest mistakes people make getting into the land business

(01:05:01) - How do you know if you’re overpaying or getting a great deal?

(01:07:21) - Identifying a slow-down

(01:16:47) ) - How has your leadership style changed over time?

(01:21:25)- What’s your favorite hotel?

On this episode, Jake and John discuss:

- Becoming a GM at 26 years old

- Building a great hotel culture

- The process of concepting a new-build

- Sourcing and capitalizing deals

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

Links:

Wylder Hotels: https://wylderhotels.com/#

John on LinkedIn: https://www.linkedin.com/in/john-flannigan-73550a1/

Topics:

(00:00:00) - Intro

(00:01:40) - John’s career in hospitality

(00:10:41) - Becoming a GM at 26 years old

(00:12:44) - Rate ceilings

(00:14:10) - Doubling revenue of a hotel

(00:15:58) - Making a great hotel website

(00:20:17) - Building a culture at a hotel 

(00:23:44) - How boutique hotels have changed over the years

(00:26:11) - Where people mess up in executing on a soft-branded hotel

(00:28:31) - The process for concepting a new-build

(00:36:15) - Sourcing deals

(00:40:10) - Capitalizing deals and managing properties

(00:49:57) - Characteristics of a strong General Manager

(00:54:14) - Mistakes made

(00:58:25) - Key components of a great F&B concept

(01:04:34) - Investment horizons

On this episode, Jake and Scott discuss:

• Leadership in the military vs. business
• Scaling Spartan
• Holding people accountable
• Vertical integration
• The Self-storage landscape

Links:

Spartan Storage

Scott on LinkedIn

No Rules Rules by Erin Meyer & Reed Hastings

The Great Game of Business by Jack Stack

The 4 Disciplines of Execution by Sean Covey

Scaling Up by Verne Harnish

Scaling up tools PDF

The Conrad Thailand

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

(00:02:17) - Scott’s military experience

(00:07:27) - Leadership in the military vs. leadership in a company

(00:10:51) - Getting into real estate

(00:18:01) - Scott’s first deal

(00:19:31) - Scaling the business

(00:29:57) - Holding people accountable

(00:36:08) - Meeting structures

(00:39:43) - Mistakes made early in the business

(00:42:33) - Vertical integration

(00:46:13) - Hold strategies

(00:46:53) - Scott’s $100m deal

(00:52:00) - The Spartan Fee structure

(00:57:40) - The self-storage landscape

(01:01:58) - Adapting to the new RE cycle

(01:07:50) - Investment and underwriting processes

(01:11:54) - Scott’s book recommendations

(01:17:12) - Advice for inspiring performance

(01:20:54) - What is your favorite hotel?

On this episode, Jake and James discuss:

• Risks in building Spec Homes
• Building in Miami and Los Angeles
• Characteristics of a great contractor
• The Luxury rental space
• Sourcing deals

Links:

Clara Homes

Amanpuri, Thailand

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

(00:02:20) - James’ journey into real estate and career

(00:15:38) Credit facilities

(00:17:05) Differentiating homes from the competition and lessons learned

(00:18:34) Risks in building spec homes

(00:19:38) Moving from LA to Miami

(00:22:42) Finishes in Spec homes

(00:27:04) Selling home pre-completion

(00:29:40) Navigating inflation and timing the sale

(00:35:00) The allure of Miami

(00:40:33) Characteristics of a great contractor

(00:41:25) The impact of climate

(00:42:46) Is your spec home business model scalable?

(00:44:35) James’ work in luxury rentals

(00:49:13) Sourcing deals

(0055:32) Structuring partnerships

(01:04:18) Staying in control of the process

(01:08:20) The Live Local Act

(01:14:12) Learning curves in pivoting to MF

(01:15:56) What is your favorite hotel?

He's passionate about aligning the firm's vision, values, and targets so that Reaume Richardson can maintain the highest standards for their employees, partners, and clients. His long history in the industry and his service in the military have taught him the value of an honest day’s work and the importance of maintaining relationships, something he instills at all levels of the company.

On this episode, Jake and Bryson discuss:

• How the construction landscape has changed over Bryson's career
• A walkthrough of a ground-up construction project
• Challenges in General Contracting
• Level 10 meetings and goal setting
• Building a development arm of the business

Links:

Bryson on LinkedIn

Reaume Richardson Construction

The Cooperative LA

The Roosevelt

The St. Regis

The Montage Deer Valley

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

(00:03:07) The construction landscape over Bryson’s career

(00:09:31) What are construction leaders doing to try and improve the bottom line for everyone?

(00:12:01) What to know when considering Modular

(00:15:03) Walkthrough of a ground-up construction project

(00:17:24) Office-to-Residential conversions

(00:21:06) Bryson’s background

(00:28:01) Challenges in General Contracting

(00:37:13) Deep dive into Pricing

(00:43:49) Healthy margins to expect

(00:45:24) Learnings from the GFC

(00:52:54) Level 10 Meetings & goal setting

(01:06:24) Building a development arm

(01:22:37) What is your favorite hotel?

On this episode, Jake and Sean discuss:

• Building Scholastic Capital
• Raising a fund for the business
• How Scholastic picks the right markets and their asset criteria
• Fundraising, leasing, financing, technology and more!

Links:

Sean on Twitter - https://twitter.com/SeanODowd15

Sean's content and Scholastic Capital - https://linktr.ee/seanodowd

Get in touch: Sean@ScholasticCapital.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

(00:02:46) Sean’s career background

(00:04:11) Lessons learned from Wharton and consulting

(00:11:38) Applying these lessons to starting your own company

(00:13:18) PE firms finding value streams

(00:15:23) Building a team of A and B players

(00:16:46) The decision to go into the RE business

(00:19:46) Sourcing the first deal

(00:23:12) The mission of Scholastic Capital

(00:25:06) How to find a “good” school district

(00:28:07) Supply

(00:29:22) Value-add decisions

(00:31:26) Requirements for a home in the right market

(00:33:01) Fundraising

(00:34:51) The SFR fund phenomenon

(00:37:07) Future capital strategies

(00:38:58) Picking a partner

(00:42:04) Biggest surprises in starting the business

(00:43:45) Structuring the fund

(00:48:52) Facilitating monthly distributions

(00:49:42) Building a team

(00:52:48) Property management

(00:55:10) Leasing & technology

(00:59:17) The importance of the home’s age

(01:00:29) Underwriting deals & what happens post close

(01:06:15) Biggest challenges going forward

(01:07:54) Financing

(01:10:30) Target returns

(01:12:44) What is your favorite hotel?

(01:14:21) Twitter’s role in raising capital

On this episode, Jake and Daniel discuss:

• The Hospitality Investing environment in 2023
• Approaches to underwriting deals
• What deals make sense as we enter a new cycle

Links:

LW Hospitality Advisors

Daniel on LinkedIn

Four Seasons Anguilla

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

(00:02:29) Daniel’s journey into hospitality

(00:07:19) What’s changed operationally and in investing over the past 40 years in hospitality?

(00:09:50) What was the most impactful thing you learned from your time in Switzerland?

(00:10:42) The Customer is always right

(00:12:07) How do you get people comfortable with the operating side of hospitality?

(00:16:29) A walkthrough of advising someone buying via auction

(00:20:52) How do you think about Brand Managers?

(00:22:15) What are the characteristics of a great hospitality investor?

(00:24:50) What hospitality deals could be replicated as we enter a new cycle?

(00:29:19) How do you view hotel REITs?

(00:30:13) Are you seeing any shifts in how people are investing in hospitality?

(00:34:08) What are the major considerations when underwriting a 10-year vs. 5-year hold?

(00:38:05) Are you seeing shifts in new investors coming into the market?

(00:40:35) What has been most surprising to you about this industry?

(00:44:03) What are the most important things when owners are bringing in 3rd party management?

(00:46:49) What are the most common frictions between managers and owners?

(00:47:55) How do you think about investing in your assets on an ongoing basis?

(00:49:54) What are you seeing in experiential hospitality?

(00:53:26) Are there certain categories that you view as more challenging in experiential?

(00:56:35) Tailwinds from the Pandemic & Airbnb’s shadow supply

(01:02:30) If you had $100m right now, how would you deploy it?

(01:06:18) What is your favorite hotel?

On this episode, Jake & Gabe discuss: 

• Going from Wall St. into Real Estate
• Building Generational Wealth
• Raising Capital
• Executing Value-Add Strategies

Links:
Gabe on Twitter

Tekton Group

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

(00:01:48) Going from Wall St. into Real Estate

(00:09:38) The desire to create generational wealth

(00:11:14) Balancing raising capital while building wealth in assets

(00:14:26) What are some key principles you abide by to protect you against being a forced seller?

(00:20:15) Waiting for the Fat Pitch

(00:25:46) Can you define sub-institutional real estate and what are some market inefficiencies you see around the asset class?

(00:30:43) How do you find deals?

(00:34:07) A walkthrough of a deal that closed 2 weeks later

(00:39:01) How do you execute quickly on your value-add strategy?

(00:43:03) What’s the structure of your fund and why did you decide to have a fund?

(00:47:48) What did you learn from the first and second funds that you’ll implement in the third?

(00:59:18) Have you thought about deals that you never want to sell?

(01:02:28) What have you learned from your worst deal?

(01:06:23) Getting tenant feedback for Capex

(01:08:26) Gabe’s philosophy around 3rd party managers

(01:12:15) What are your goals over the next 3 years?

(01:17:12) What is your favorite hotel?

In this episode, Jake and Jamal discuss:

• Jamal's operating portfolio
• Finding jockey's for businesses Jamal invests in
• Developing a growth mindset
• Underwriting, acquiring, and exiting businesses

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 

Links:

Jamal on Twitter

Topics:

(00:02:14) Jamal’s first inklings for entrepreneurship, playing in the NBA, and operating portfolio today

(00:13:54) Doing a deal with Outback Steakhouse

(00:16:28) Finding a great Jockey of a business and being part of the foundation of an investment

(00:20:42) Developing a growth mindset

(00:34:55) Choosing Kentucky for college

(00:38:12) What are some of your major insights in your career post-NBA?

(00:44:04) How do you communicate that you don’t know everything without feeling pushed around?

(00:47:51) What have you learned from operating over multiple business cycles?

(00:51:17) Finding success in the car business

(01:00:29) How do you think about exiting a business?

(01:04:23) How difficult has it been with labor in some of these businesses?

(01:10:28) How do you keep a pulse on all of the businesses you’re involved in?

(01:15:03) How do you underwrite a small business?

(01:22:43) Are there any niche sports teams or industries that would be interesting to acquire?

(01:32:51) What is your favorite hotel?

Today, Roundhouse focuses exclusively on providing high-quality housing options in emerging cities across the Western United States. In order to deliver superior experiences to our employees and residents we have built a fully integrated service offering that spans the construction, property management, and design disciplines. 

On this episode, Jake & Casey discuss:

• Learning to structure long-term horizon deals
• Avoiding competing with institutional capital
• Structuring deals for acquisitions vs. developments
• The advantages of being vertically integrated -
• Casey's 6-month sabbatical and how to have your company be successful without you

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 

Links: 

Roundhouse: https://rndhouse.com/

Casey on Twitter: https://twitter.com/roundhouse208

Topics:

(00:02:18) Casey’s RE Career in Southern California

(00:11:40) The decision to pivot out of LA

(00:15:54) Learning to structure long-term horizon deals

(00:18:41) How do you avoid competing with institutional capital?

(00:22:04) How have you figured out how to raise enough capital without going to someone with deeper pockets?

(00:24:41) How do you structure deals when they are acquisitions vs. developments?

(00:31:08) How often are you refinancing in order to return capital?

(00:35:48) How do you think about Capex in multifamily over long hold periods?

(00:43:38) How are you differentiating your high-end products?

(00:47:00) What are the advantages of being vertically integrated?

(00:50:59) What does enterprise value mean to you?

(00:57:53) Are you at a point where the team can raise capital without you?

(01:02:28) What was the scenario that led to you buying out your partner?

(01:07:51) How do you ensure leadership values are being replicated across the business?

(01:11:29) What was the biggest insight you gained from your 6-month sabbatical

(01:19:44) Casey’s emphasis on design

(01:22:18) What is your favorite hotel?

Peachtree Hotel Group's track record spans more than 580 real estate transactions and $8.0+ billion in total capitalization of real estate assets.

Links:

Peachtree Hotel Group

Greg on LinkedIn

Ritz Reserve Dorado Beach

The Montage Laguna Beach

Topics:

(00:01:44) Building Peachtree

(00:06:52) Why was hospitality intriguing as an asset class?

(00:09:04) Do you ever feel capped by the amount of capital you can raise by only being in hospitality?

(00:12:12) How important is vertical integration?

(00:17:33) How have you made money buying debt?

(00:24:29) What were some learnings you’ve had from previous cycles?

(00:28:26) How do you manage your reputation and perception while playing in a debt environment?

(00:31:40) How critical is it to manage your P&L?

(00:37:10 Holding investment committee on a Friday

(00:38:57) Do you tour every asset?

(00:40:25) What are the most interesting opportunities to you on the equity side right now and the near future?

(00:44:30) How much emphasis are you placing on the actual real estate vs. the operating company?

(00:46:40) Selling a fully renovated hotel vs. selling a hotel that needs renovation

(00:49:27) What are some trends you’re seeing in hospitality that could be interesting investments?

(00:51:54) Are you working on any conversions?

(00:52:05) Would you ever break any of your verticals off or use them to buy another company?

(00:55:34) What’s your favorite hotel?

Prior to launching Torose, Scott co-founded Tricera Capital where he led the charge on strategic direction, capital markets and sourcing investment opportunities. In this role, Scott built a portfolio in excess of $700M over five years and consistently delivered returns in excess of 20% IRR and a 2x multiple across realized investments. Scott maintains ownership and major decisions across the Tricera portfolio and continues to be a minority owner of Tricera Capital.

Torose Equities is a Miami-based real estate investment firm with several different verticals, including a value-add urban retail, office, and mixed-use strategy within the Southeastern United States. 

On this episode, Jake & Scott discuss:

• Important retail trends that will shape the next decade
• The science of placemaking
• The opportunity for Office
• Working with Family Office Investors
• Building Torose Equities

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

Links:

Torose Equities

Scott on LinkedIn

Assembly Row Boston

Ennet Perry Cabin

Topics:

(00:01:40) Scott’s background and career

(00:10:37) Learnings from working in international markets

(00:13:16) How are you choosing what markets to choose on now?

(00:15:14) Risk and reward in investing

(00:17:57) What is your competitive edge?

(00:19:12) What are some important retail trends that will shape the industry over the next decade?

(00:21:40) What’s important for Office investors over the next 5-10 years?

(00:27:40) Pros and Cons of Commercial and Retail Investing

(00:29:38) Placemaking

(00:36:40) What do you look for in locations for the success of retail?

(00:39:47) What is the opportunity for Office in Florida?

(00:42:32) Developing a 350k sqft covered land play

(00:48:18) How are you finding Family Office investors?

(00:49:17) Co-GP opportunities

(00:50:14) Characteristics of good partners

(00:51:26) Building Torose Equities

(01:01:16) How are you sourcing deals?

(01:05:06) What’s your approach to value-add?

(01:09:11) What processes have you implemented in your company?

(01:11:33) What is your favorite hotel?

On this episode, Jake and Dev discuss:

• Growing up in the family hotel business
• How to build successful partnerships
• Creating long-term investment structures

Links:

Dev on LinkedIn

Merrimac Ventures

Six Senses Douro Valley

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:

(00:02:00) Dev’s upbringing and career in real estate and hospitality

(00:12:46)Mentorship

(00:16:42) Meeting Donald Trump

(00:19:10) Acquiring a full city block of real estate

(00:21:24) What asset classes were you working on outside of hotels early on in your career?

(00:24:19) How did you raise capital on your first deal?

(00:28:15) Key characteristics of land sites that make it work

(00:32:34)Working with LPs

(00:37:01) How are you structuring deals?

(00:39:35) How are you unlocking liquidity as you begin working with family offices and high-net-worth individuals?

(00:41:39) What are some of the mistakes you’ve made buying land?

(00:48:23) How are you thinking about investing in other parts of FL?

(00:51:01) Going into the Telluride market

(00:58:52) Condo economics

(01:07:35) Thoughts on shadow STRs

(01:10:28) How to deal with challenging partnerships

(01:12:53) What’s your favorite hotel?

The Company currently owns assets in North America, Latin America, Mexico and the South Pacific. The Canyon Group’s resorts are managed by marquis brands such as Amanresorts, Six Senses, Four Seasons Hotels & Resorts and Hyatt Hotels and Resorts. Under Vazifdar’s leadership, many of the Canyon Group’s ultra-luxury assets have achieved high global accolades and are considered the “Best in Class” with extraordinarily high occupancies and rates.

On this episode, Jake and Homi discuss:

- Selling a brand for $2m per key

- Building Amangiri and Amangani

- How to make experiential luxury work

- How to make select service hotels work

Links:

Canyon

Homi on LinkedIn

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:

(00:01:55) Homi’s journey into Real Estate and hospitality

(00:07:42) What is most important when you are reinventing yourself?

(00:08:43) Building Canyon and the focus on ultra-luxury assets

(00:28:24) Swapping federally controlled land and creating a profitable asset in remote Utah

(00:48:47) How do you make a tent experience work?

(00:54:44) How do you find labor and built infrastructure in these remote areas?

(00:58:22) Is establishing a sense of community at a resort important?

(01:04:00) How have you learned to invest and stay afloat during cycles?

(01:13:11) What will be the biggest challenge in replicating this new concept?

(01:15:11) Homi’s select service hotel

(01:21:23) What is your favorite hotel?

Born and raised in Turin, Italy and fluent in English, Italian, French and German, Governato is particularly focused on guest experience, believing that "luxury service should happen without guests knowing where it comes from."

On this episode, Jake and Mauro discuss:

• How Mauro approaches managing an ultra-luxury hotel
• The story of the Château de la Messardière
• How luxury and experiential travel has changed
• Balancing how you create moments in a hotel with profitability

Links:

Mauro on LinkedIn

Château de la Messardière

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:

(00:02:12) Mauro’s background and career

(00:07:33) Insights and advantages of starting in Hospitality on the F&B side

(00:10:18) How do you recognize a guest?

(00:13:22) Mauro’s management style

(00:16:47) Experiences working in the Maldives

(00:20:47) The story of the Château de la Messardière

(00:25:52) Balancing creating moments with hotel profitability

(00:36:42) The most important physical components of a luxury resort

(00:41:28) How has luxury and experiential travel changed in the last 5 years?

(00:46:05) How have you built a culture of always finding ways to continuously enhance the visual moments?

(00:50:21) What would surprise people most about operating an ultra-luxury hotel?

(00:53:49) Why do hoteliers mess up the F&B program so often?

(00:56:25) What’s the best way to work with a partner

(00:58:48) What is your favorite hotel?

Mr. Hehir received a Bachelor of Science Degree in Hotel Administration from Cornell University and a Diploma in Hotel Administration from the Hotel Institute Montreux, Switzerland.

On this episode, Sean and Jake discuss:

• Executing $500m of renovation projects
• Raising capital
• Fostering a no-asshole culture
• Strategies and deal criteria

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

Links:

Sean on LinkedIn

Trinity Investments

Topics:

(00:02:11) Sean’s journey from Botswana to the United States

(00:06:50) Influences on Sean’s investment decisions

(00:07:56) Where do you see hotel labor moving within the US?

(00:10:31) How did you learn to be an investor?

(00:13:49) Why drew you to hospitality?

(00:16:25) Does being in Hawaii make you feel left out?

(00:17:53) What trends are you focusing on now that will pay dividends in the next decade?

(00:22:10) Executing $500m of renovation projects

(00:26:02) Raising Capital

(00:27:48) Do you fear more pain in the hotel industry?

(00:29:39) Where will you be investing as we enter another cycle?

(00:31:18) Learnings from the GFC

(00:33:04) What is a GP fund?

(00::36:43) How do you go to major banks and raise from them?

(00:39:57) How do you design your fee structure?

(00:40:55) What did you learn from the GFC that showed you the massive opportunity coming from Covid?

(00:45:41) How do you think about the enterprise value?

(00:48:16) Thoughts on WFH from a business owner perspective

(00:51:19) Fostering a no-asshole culture

(00:52:36) The process of raising funds

(00:59:28) How do you execute your business plan with an existing manager in place?

(01:02:18) How do a 4 Seasons and Hilton differentiate in their focuses?

(01:04:07) Navigating luxury F&B and discussing deals

(01:12:05) Strategy and deal criteria

(01:12:08) Micro resorts

(01:25:23) What makes a great partner?

(01:29:00) What is your favorite hotel?

Mehul's start in the hotel business came when he and his family moved to Garland, Texas, from India when he was 13. From 1990 to 1993 he and his family worked and lived in a hotel-his parents as room attendants and Patel and his brother as everything from front-desk clerks to landscapers.

On this episode, Mehul and Jake discuss:

• NewcrestImages's process for purchasing portfolios
• How they raise capital
• Knowing which deals to pursue and stay away from
• How and why they purchased a bank

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

Links:

NewcrestImage

Mehul on LinkedIn

Topics:

(00:00:00) Mehul’s journey into hospitality

(00:13:05) Buying a portfolio of hotels from Blackstone

(00:15:14) Is there less risk in buying a portfolio vs. one-off assets?

(00:20:24) How do you raise capital in a portfolio acquisition?

(00:23:27) Who on your team leads an acquisition and what are you most focused on in diligence?

(00:27:38) What are you doing on an asset management level that the larger organizations aren’t?

(00:33:51) What type of deals do you know to stay away from?

(00:35:12) Why have you found Ground Lease to be painful?

(00:41:13) What is the biggest opportunity you’re seeing today?

(00:47:10) How do you think about ROI in the renovations you’re doing?

(00:52:59) Is there one asset class you’ll lean into over the next cycle?

(01:00:57) How do you reconcile that the real estate is more valuable than the building itself?

(01:03:56) A walkthrough of an acquisition

(01:13:09) Are there any never-sell assets in your portfolio?

(01:14:12) Buying a bank

(01:23:16) What’s your favorite hotel?

The younger Cobb became a lawyer and cannabis lobbyist before founding his own marijuana company, Bluma Wellness, which he sold in April 2021 to Cresco for $213 million in an all-stock deal. In November 2022, Cobb took his father's rich history of smuggling and launched Sunburn in Florida, a vertically integrated dispensary chain with nine retail shops.

Sunburn is the 13th largest medical marijuana company in Florida, the company is valued at $105 million and will generate around $50 million in revenue by the end of its first year in operation.

On this episode, Jake & Brady discuss:

• How Brady's father got into the world of Cannabis smuggling
• Opportunities in the Cannabis industry
• Building a Cannabis farm and distribution operation
• How to raise capital in Cannabis

Links:

Sunburn Cannabis

Brady on Instagram 

Lefay Resorts Italy 

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

Matthew serves as President of the company, engaged in the sponsorship of 40 Class-A multifamily, mixed-use, and retail development projects comprised of over 8,000 units that are operating, under development or disposed plus, over 700K sf of office and retail space, with a total capitalized cost in excess of $4 billion.

On this episode, Jake and Matt discuss: 

• Building a real estate database to generate deal flow
• Learnings from the GFC
• How they capitalize deals
• Using self-management as a key to growth
• A walkthrough of a typical deal for Post Brothers
• What metrics matter to them in a deal

Links:

Post Brothers

Matt on LinkedIn

The Berkeley London hotel

The Corinthia London hotel

Oil Nut Bay

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:

(00:01:59) The first time Jake heard of Matt

(00:05:20) How Matthew got started in RE and built a Real Estate Platform

(00:10:08) How did you begin creating your database to generate deal flow?

(00:13:18) Matt’s first deal

(00:16:36) Matt’s learnings from the GFC

(00:18:55) How were you capitalizing early on and when did you move into institutional capital?

(00:25:47) At what point did you realize you needed the organization to be vertically integrated?

(00:27:22) Was self-managing key to your growth?

(00:28:51) What are the ways you’ve found to make money in the Operating Company?

(00:35:47) What’s your preferred playbook when working on a deal?

(00:38:47) What’s the size and scale of PB today?

(00:40:19) How do you resist the temptation to do every single deal that comes across your desk?

(00:44:22) What does a typical deal process look like for you?

(00:51:28) What metrics matter to you in a deal?

(00:58:01) Office to MF conversions

(01:03:03) How major cities experiencing loss of population will fare

(01:06:40) What amenities are you prioritizing in projects right now?

(01:10:14) Are there any ideas you’re planning on implementing that you haven’t so far?

(01:11:59) Furnished Apartment concepts & thoughts on the hotel industry

(01:22:24) What is your favorite hotel?

Chris is a founding member and the board President for the Civic Center Conservancy, the City of Denver’s private partner at Civic Center Park. He is also Board Chair for the Rocky Mountain chapter of the Young Presidents’ Organization, and a member of the Board of Governors’ for the Denver Metropolitan Chamber of Commerce.

On this episode, Jake & Chris discuss:

- how they find deals

- East West's acquisition process

- setting up multiple offices to enhance the development flow

- the difference between condos & hotels how to make it work

- large scale resort development

- managing risk

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

Links:

Chris on LinkedIn - https://www.linkedin.com/in/cframpton1/

East West Partners: https://www.ewpartners.com/

Petit St. Vincent - https://www.petitstvincent.com/

Cayo Espanto Beliz - https://aprivateisland.com/

The Soho Grand NYC - https://www.sohogrand.com/

One Hotel Hanalei Bay - https://www.1hotels.com/hanalei-bay

Topics:

(00:02:05) Chris’ career in real estate

(00:12:17) East West’s focus on providing value to buyers

(00:16:39) East West’s PM approach

(00:19:51) An inside look at the 3 companies within EastWest

(00:26:08) How has the organization changed in your time there?

(00:30:19) How did you expand to all these different markets while maintaining the core value of living where you work?

(00:35:04) What incentives worked when giving ownership to employees?

(00:38:35) How have you been able to survive real estate cycles and maintain a massive development pipeline?

(00:43:17) Fee Development for another party

(00:49:15) Is there room for more master resorts?

(00:51:32) What was your greatest investment?

(00:54:24) How are you capitalizing deals?

(00:57:02) How do you approach reporting?

(01:01:18) Is there a mistake that you made that lingers for you?

(01:04:09) How are you managing risk through the acquisition pipeline?

(01:11:17) How do you structure a Condo Hotel?

(01:19:28) What is your favorite hotel?

Opterra’s core investment strategies focus on both value-add (opportunistic) and stabilized, income-oriented assets in the hospitality, office and multi-family sectors. Our approach seeks to capitalize on mid-market opportunities in the $25 -150 million range in the United States, Canada, and the Carribean. Our investment strategy is strongly influenced by our deep asset management experience to identify the proper capital repositioning, cost reduction and operating leverage opportunities inherent in each asset to maximize returns to investors.

On this episode, Jake & Glenn discuss:

• Glenn's experience at Blackstone and it's influence on starting Opterra
• How they evaluate deals
• The 'no-assholes' policy
• Developing an asset management platform
• Acquisitions

Links:

Opterra Capital

Glenn on LinkedIn

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

Timecodes:

(00:01:01) Glenn’s career at Blackstone and the decision to leave

(00:06:39) Rolling the Blackstone mentality into Opterra

(00:08:09) Glenn on falling in love with Hospitality

(00:09:57) How Blackstone shaped Glenn’s Investment Perspective

(00:13:02) How Opterra evaluates deals

(00:16:54) Opterra’s capital strategy

(00:19:15) Converting Office into a Luxury Hotel

(00:23:49) Structuring a business to be focused on doing what you want to do

(00:26:35) The ‘no-assholes’ policy

(00:32:46) Post-Pandemic approach to doing deals

(00:34:29) Qualities behind great RE investors and asset managers

(00:39:01) Developing an asset management platform

(00:44:11) Implementing processes at Opterra

(00:49:19) Acquisitions processes

(00:57:49) Areas in Hospitality ripe for disruption

(01:04:56) How have the past 3 years informed your decisions for the next 5 years?

(01:09:58) How do you know when to sell?

(01:15:32) What’s your favorite hotel?

On this episode, Jeff & Jake discuss:

• How Affiliated works with city governments to develop workforce housing
• Raising capital
• Walkthrough of a typical deal
• Construction, design, and underwriting

Links:

Affiliated Development

Jeff on LinkedIn

The Dalmar Hotel

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

Timestamps:

(00:01:52) Jeff’s career

(00:08:48) Choosing to play in the Multifamily asset class

(00:14:41) Utilizing HUD loans

(00:15:27) How do you find markets to enter?

(00:18:44) How Jeff engages with city governments

(00:21:17) Defining workforce housing

(00:27:14) What incentives are you getting from cities and counties?

(00:37:44 How are you raising capital?

(00:46:01) How long does a typical deal take from start to finish?

(00:48:30) How are you using your in-house architecture function?

(00:53:46) How are you thinking about construction costs and design?

(01:02:06) How are you underwriting deals?

(01:10:30) How do you choose your property managers?

(01:14:01) How do you approach inclusionary housing?

(01:16:37) What is your favorite hotel?

Through their offices in New York, Los Angeles, Miami, San Francisco, and Dallas, ACORE originates, acquires and manages first mortgages, B-notes, mezzanine debt and preferred equity throughout the United States. Since inception in 2015, ACORE has closed over $35 billion in more than 453 transactions.

On this episode, Jake and Warren discuss:

• Migration patterns influencing investments
• Building ACORE and their growth strategies
• How the lending environment will change in the future

Links:

ACORE Capital

Warren on LinkedIn

Four Seasons Surf Club

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

Timestamps:

(00:02:08) Warren’s move to Miami

(00:06:21) Migration pattern influencing investments

(00:09:00) Navigating Work From Home

(00:12:10) Warren’s background, early career, and thoughts on today’s market

(00:22:22) The regional banking crisis

(00:27:43) Loan extension challenges

(00:34:41) Why didn’t you end up in Hospitality?

(00:38:19) The thesis for starting Acore

(00:49:35) Challenges in scaling the org

(01:02:22) Capital Deployment strategies

(01:04:59) How Acore makes money

(01:09:58) Opportunities for Sponsors to work with Acor

(01:15:40) How lending will evolve over the next 5 years

(01:17:15) What assets are you staying away from?

(01:20:17) What is your favorite hotel?

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

Timestamps

(00:01:02) Why are we talking about Fees?

(00:03:39) Why GPs charge fees

(00:09:02) Deal shops vs. Real Estate Private Equity Firms

(00:10:23) Charging market fees to build great returns & borrowing costs

(00:14:45) Real Estate Operating Companies vs. Assets

(00:17:15) Understanding where your company is at in it’s life cycle

(00:18:42) Primary components and fees you’ll see

(00:20:04) What to charge for and include in fees

(00:22:10) Do not operate at a loss

(00:23:08) Project Management vs. Asset Management

(00:29:24) Final Thoughts

On this episode, Jake & Arash discuss:

• Key components to creating an amazing branded hotel,
• F&B strategies and why it’s such an important aspect of hospitality,
• Learnings from working with Barry Sternlicht
• Acquiring and scaling brands.

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Links

Highgate

Arash on LinkedIn

The Viceroy Hotel: Sugar Beach at St. Lucia

Timestamps

(00:02:38) How do you experience a hotel when you travel and what are you looking for?

(00:05:29) How did you get started in this industry?

(00:09:54) What about your journey has shaped how you are as a leader and how you build brands?

(00:13:02) What are some key elements that separate Hospitality characters from Hospitality business folks?

(00:15:16) How are you making sure employees are bought in?

(00:19:20) How many hotels fall under your portfolio?

(00:21:39) Where are you spending the majority of your time day to day?

(00:23:57) Is there an optimal scale to justify implementing Business Intelligence technology?

(00:27:24) What was most surprising to you when you joined High Gate?

(00:29:12) Do you see branded hotels growing or shrinking?

(00:33:20) Are you working on creating new brands?

(00:42:45) F&B Strategies and amazing restaurant operators

(00:53:54) What are some of the things you learned working with Barry Sternlicht?

(00:57:31) What are some best practices for prioritizing your work?

(01:00:46) How are you trying to grow the business?

(01:04:01) Have you been looking at acquiring brands that your infrastructure is uniquely equipped to scale?

(01:07:01) What mistakes do you see most often from operators and investors?

(01:09:50) What are you seeing in the market forecast?

(01:11:47) What is your favorite hotel?

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 Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Links:

Hersha Hospitality Trust

Jay on LinkedIn

The 4 Seasons Boston

Timestamps:

(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?

Since joining Morgan in 2012, Evan has been involved in developing and acquiring over 7,000 units at a cost exceeding $1.8B. Prior to joining Morgan, Evan co-founded BlueRoot Partners to take advantage of opportunities to acquire distressed real estate. Evan began his career at Torchlight Investors (f/k/a ING Clarion) restructuring non-performing commercial real estate.

On this episode, Jake and Evan discuss:

• How Morgan Group sources deals and develops assets
• How to enhance Multifamily assets
• Overseeing 20+ projects at one time
• The US Housing Shortage
• Mitigating risk during hold periods

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Links

Morgan Group

Evan on LinkedIn

Eagle Island Lodge, Botswana

Timestamps

(00:02:16) Evan’s career in Real Estate

(00:11:02) Why Scale is important: Plentiful 3rd party Managers

(00:15:21) Thoughts on market strategy

(00:19:13) Being ‘Hyper-local’ in development and construction

(00:22:00) Making the jump from being an entrepreneur to a Family business

(00:25:06) Headline stats for Morgan Group

(00:26:34) How Morgan sources deals and develops

(00:35:57) Thoughts on Single Family Rentals & High-end rental projects

(00:40:02) Adam Neumann

(00:41:49) How to enhance Multifamily assets

(00:43:32) The reality of overseeing 20 projects at once

(00:48:55) What is the best way to mitigate risk during a hold period and structure deals?

(00:52:33) Being a non-family member leading a Family Business

(00:56:29) Thoughts on the Housing Shortage

(01:01:20) What incentives are you setting up for team members?

(01:09:31) Why do you self-perform?

(01:13:20) Making money on the construction side of the business

(01:17:20) How are you building the company to perform over the next 5 years?

(01:23:44) What is your favorite hotel?

Jake and Chris discuss: 

• How to create an exceptional hospitality experience
• How to underwrite hotel investment opportunities
• Partnering and learning from Barry Sternlicht
• How to add value to different types of hotels

Links

Check out Chris Powers and The Fort Podcast

Hotel Bel-Air

Brush Creek Ranch

Blackberry Farm 

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Timestamps

(00:03:14) How do you experience hotels?

(00:05:14) What is Hospitality?

(00:08:17) Jake’s journey into Hospitality

(00:09:45) Jake’s Companies

(00:11:36) Hospitality during Covid

(00:21:42) How do branded hotels differentiate from each other?

(00:23:12) What does great operation look like in a Commodity Hotel?

(00:25:04) How are daily rates set?

(00:32:39) Airbnb vs. Hotels

(00:35:15) How do you define Lifestyle?

(00:36:21) Who are people you admire in this industry?

(00:39:02) Are there any emerging brands that will overtake the top luxury brands?

(00:40:51) How would a hotel development come together?

(00:44:19) What are you looking for in a hotel when you want to buy?

(00:47:21) What’s a soft brand?

(00:48:19) Do you need experience to partner with a Hilton or Marriott?

(00:49:14) What does upgrading management look like?

(00:54:34) What feedback do you see most often from guests?

(00:57:48) Jake on partnering with Barry Sternlicht?

(01;03:50) The One in Miami

(01:07:56) How do you approach F&B?

(01:09:30) What’s the greatest hotel in the world?

(01:13:16)  How do you view hotels as investable assets over the next 5 years?

(01:16:19) Are there any new revenue streams on the horizon?

Focused on concept and business development, John drives the creative process for the company, envisioning restaurants and bringing them to life, as well as forging new partnerships with hotel developers to create bespoke food and beverage experiences for their guests.

John began LDV in 2008, with critically acclaimed flagship Scarpetta restaurant, followed by signature brands American Cut and Dolce Italian.

On this episode, Jake and John Discuss:

• Creating the Ultimate Dining Experience
• Building a Restaurant in Rome
• Scaling LDV to a Global level
• Leadership Lessons

Links:

LDV Hospitality: https://ldvhospitality.com/

Ralph’s Restaurant in Paris: https://www.ralphlauren.co.uk/en/global/ralphs-paris/7120

Outliers by Malcolm Gladwell: https://bit.ly/42k0AMX The Grand

Hotel Parker's Naples Italy: https://en.grandhotelparkers.it/

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Timestamps:

(00:02:14) - Introducing John & his journey into hospitality

(00:06:26) - Early lessons on how to cultivate an experience in Hospitality

(00:11:32) - What characteristics are you for in partners?

(00:13:39) - How do you set the vision for a project?

(00:16:05) - Scaling on a Global level

(00:27:14) - What are the tipping points for restaurants in design that you implement every time?

(00:31:35) - The changing way people engage with night life

(00:34:37) - Membership concepts

(00:37:54) - Designing a restaurant in Rome

(00:53:07) - What would surprise listeners about your leadership style?

(00:57:02) - Mentorship

(01:01:36) - Can a chef own a truly successful restaurant for a long period?

(01:04:17) - How have you managed to rebuild investor confidence and maintain relationships since the Pandemic?

(01:10:51) - How do you utilize what you learn from traveling?

(01:12:30) - What is your favorite hotel?

As President, Alex is focused on strategic planning, people development, pursuing growth and new opportunities, promoting the delivery of memorable customer service and ultimately being the best third-party management company in the industry, acting in the best interest of owners every day. 

On this episode, Jake and Alex discuss:

• How Alex grew a 20-hotel company to 250 hotels via mergers and acquisitions
• How Hotel M&A works
• How to run a Global team
• Integrating teams through Mergers
• Creating an F&B think tank platform

Links:

Alex on LinkedIn

Pyramid Global Hospitality

Willow’s Lodge - Seattle

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Topics:

(00:02:17) - Completing a major Merger during the Pandemic

(00:12:51) - What are you able to do post-merger that you weren’t able to before?

(00:17:20) - How are you creating a culture that fosters retention?

(00:19:53) - Is scale and size better in the management business?

(00:29:17) - What behaviors thrive at the senior level in Hospitality?

(00:34:40) - Mergers and Acquisitions

(00:44:32) - What have you learned from your partner, Warren?

(00:47:47) - How are you thinking about growing your management company?

(00:51:51) - How are you handling the leadership position after all these mergers?

(00:53:47) - Structuring a Merger

(01:00:57) - How are you integrating the positives from lifestyle hotels with the other assets in your portfolio?

(01:04:57) - What have you found to be some of the best ways to win at F&B?

(01:08:52) - How are you optimizing costs & hiring?

(01:14:29) - How are you thinking about leadership interactions and meetings with your team?

(01:18:52) - What is your favorite hotel?

Links:

Smith Travel Research

FRED (Federal Reserve Economic Data)

CoStar

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Topics:

(00:01:02) - Introducing our first solo show!

(00:02:19) - Defining Underwriting

(00:03:32) - What happens when a deal comes into DoveHill: Evaluating the qualitative factors of a potential asset

(00:11:11) - Quantitative Factors: Price, historical performance, revenue trends, and expenses

(00:20:17) - Modeling: Back of Napkin method

(00:23:02) - Implementing the in-house management team & identifying Capex issues

(00:30:14) - Underwriting the Capital Structure

(00:32:57) - The Exit Scenario & Stating Risks

(00:35:40) - Easy mistakes to make

(00:40:29) - The investment committee process

(00:42:53) - The importance of timing

(00:44:35) - Closing thoughts & Call to action

As CEO of Moss, Scott inspires and empowers his team to create the exceptional. His innate curiosity drives a culture of continuous learning where insight, engagement, and determination define an individual’s success. 

On this episode, Jake and Scott Discuss:

• The process of building a generational family business
• Implementing a Vision Leadership Council
• A deep dive on the Construction Industry
• Moss' growing Solar Business

Links:

Scott on LinkedIn

Moss Construction

The Palace in St. Moritz

Connect & Invest with Jake:

Follow Jake on Twitter

Take the Hospitality Investing Masterclass

Learn How to Invest with DoveHill

Topics:

(00:02:50) - Scott’s career in construction

(00:12:56) - Do you set goals every year or every 5 years?

(00:13:50) - How has the construction market changed over the past 10 years?

(00:16:21) - Are you seeing non-diversified companies go under?

(00:17:44) - How do you select new markets?

(00:20:51) - How do you think your customers view your company?

(00:23:19) - What are some mistakes you see developers make?

(00:27:40) - When should people start the conversation with their General Contractor?

(00:29:53) - What are your first steps when you begin a project?

(00:33:19) - When a market is lacking sub-contractors, do you ever bring in subs from out of the market?

(00:34:48) - What’s changed in your strategy over the past 5 years?

(00:37:53) - How do public and private jobs differ?

(00:41:23) - Scott’s Vision Leadership Council

(00:48:38) - Can you repair trust once it's broken?

(00:50:24) - How do you view your role with regard to this council?

(00:51:32) - How do you ensure your culture scales with the company's growth?

(00:56:59) - What meetings are you attending that help you keep a pulse on the business?

(01:01:18) - Where is most of your energy spent on a weekly basis?

(01:04:13) - What are your goals for the solar side of the business?

(01:06:04) - How much does China impact the future of your business?

(01:09:40) - Are you seeing any major shift in your industry right now?

(01:15:23) - How are you building Moss to be a generational business?

(01:21:32) - What is your favorite hotel?

Kupperman Companies designs, develops, and acquires hotels, retail, multi-family, and mixed-use projects in Louisiana, Texas, Georgia, Alabama, Colorado, and across the Gulf Coast. They invest in award-winning historic redevelopments that preserve the history, architecture, and culture of the surrounding community.

Kupperman currently owns and manages over 520,000 square feet of hospitality, retail, and mixed-use assets and over 100 acres and 500 pads of manufactured housing communities through their affiliate, Lucky Communities.

On this episode, Jake and Zach discuss:

• Transitioning from law into Real Estate
• Historic Tax Credit deals
• The impact of New Orleans' transformation since Katrina
• Acquiring one of the most coveted pieces of Real Estate in Aspen, CO
• Building partnerships with hospitality operators

Links:

Kupperman Companies

Zach on LinkedIn

The Little Nell in Aspen

The Chloe, New Orleans

Hotel Saint Vincent, New Orleans

Hotel Peter & Paul, New Orleans

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Topics:

(2:27) - Zach’s transition into real estate

(7:12) - How do Historic Tax Credit deals work?

(10:04) - How did placemaking become a bigger part of your strategy?

(11:30) - How has New Orleans changed since Katrina?

(14:08) - What else does the city need to do from a RE perspective?

(14:52) - What led you to add hospitality to your portfolio?

(17:57) - Do memberships offset some of the costs that you lose with smaller door counts?

(19:37) - With The Drifter & Hotel St. Vincent, what was your intention in setting the vibe?

(24:16) - How do you structure your deals?

(26:02)  - Where are your investors located?

(26:24) - What did your debt and equity structure look like for the Saint Vincent Hotel?

(32:36) - What did the business plan for the hotel end up being?

(39:55) - What aspects of a historic tax credit deal would give you hesitation before jumping in on one?

(41:02) - Do you manage Hotel St. Vincent?

(42:03) - What have you learned about hotel ops?

(43:42) - What are you focusing on now when thinking about new deals?

(45:01) - Do your investors ever express concern about diversifying your portfolio?

(46:39) - Are there any big opportunities that have you excited right now?

(47:46) - How does a guy from NOL get one of the most coveted pieces of RE in Aspen, CO?

(54:43) - How important is integrating F&B into the hotel experience today?

(56:20) - How are the independent hotels in your portfolio competing against the market?

(1:01:08) - Converting Hotels into MF

(1:09:59) - How do you run Kupperman and how have you utilized that strategy to grow the firm?

(1:13:44) - What does a typical week look like for you?

(1:15:41) - How did you train your offshored underwriter?

(1:20:13) - What is your favorite hotel?

On this episode, Jake and Matt discuss:

• A walkthrough of converting an independent hotel in Hawaii 
• Developing Investor Relations
• Growing and evolving a Management Company 
• Key to differentiating the hotel experience

Links:

PacificaHotels.com

Matt on Instagram

King Kamehameha's Kona Beach Hotel

Hotel Bel Air

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Topics:

(00:02:07) - Matt’s career background

(000:07:46) - What did you do within the hotel asset that made you so successful?

(00:08:50- What did you come to be known for?

(00:10:00) - What was so appealing about doing deals in California?

(00:11:24)- How would you describe your portfolio in 2023?

(00:12:51)- Converting an independent hotel

(00:19:46) - Selling an Asset to Blackstone

(00:23:41) - How do you think about taking a profit?

(00:29:33) - What happens when you have a ReFi?

(00:32:57) - Do you readjust your holding patterns when working with Institutional Capital?

(00:36:25) - What have you learned about Investor Relations?

(00:39:52) - Where do you find investors now?

(00:41:07) - What pillars won’t you move on in negotiating with investors?

(00:42:18) - What was it like being managed by Blackstone?

(00:44:52) - What’s the process of creating a Hotel Brand?

(00:50:20) - Is there a certain size hotel where the amenities become challenging?

(00:53:18) - Are there simply too few deals out there?

(00:54:16) - Is it unsettling having all this dry powder on the sidelines?

(00:55:46) - How has your management company evolved over the years?

(00:57:42) - What key things do you focus on to differentiate the hotel experience?

(01:03:18) - How do you think about preparing your business for the next generation?

(01:07:26) - How are you growing the management company?

(01:09:54) - What is your favorite hotel?

(01:14:46) - Where can people find you online?

On this episode, Jake and Vamsi discuss:

• Breaking down Vamsi's first deal
• Growing Arbor Lodging and building a vertically integrated management team
• Maintaining efficient deal pipelines
• Converting Hotels to Multifamily

Links:

Vamsi on LinkedIn

Arbor Lodging Partners

The Grand Hyatt Kauai

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Topics:

(1:50) - Vamsi’s journey into Hospitality

(6:38) - What happened in your first deal?

(8:05) - How did you raise money for the deal?

(10:41) - Looking back, what were some of the questions you should have asked in your first deal?

(12:14) - How did you structure the deal with investors?

(12:57) - Hospitality as a complex asset

(14:51) - Were you looking for broken RE deals early on in your career?

(17:15) - When did you start to grow your team?

(18:57) - What made you decide to bring management in-house?

(21:20) - Did institutional partners start to flow in once you became vertically integrated?

(22:04) - How has your philosophy been shaped by doing deals in markets outside your own backyard?

(25:36) - How do you and your partner figure out what deals and markets you’ll focus on?

(28:21) - How do you keep your acquisitions team incentivized and motivated?

(31:45) - How do you make sure your deal pipeline is as efficient as possible?

(32:52) - What is your strategy for 2023?

(34:58) - Are you looking at converting Office to Hotel?

(39:40) - Do you have separate capital for Debt and Equity?

(42:36) - How do you make the economics work at scale?

(45:26) - Why do you work with institutional partners vs. syndicating deals?

(53:30) - At what point did you start viewing the management side as its own business?

(58:31) - What’s something surprising that you’re doing in the management company?

(1:00:03) - What tools are you using to maintain a pulse on the business?

(1:05:22) - How do you approach hybrid work with your teams?

(1:07:10) - How do you convert hotels to multifamily?

(1:18:13) - What is your favorite hotel?

The Buccini/Pollin Group has acquired and developed over $5 billion of properties in every real estate asset class throughout the United States since its founding in 1993. BPG is the developer, owner and operator of over 40 hotels, seven million square feet of office space, 15 major residential communities, numerous retail properties, and multiple sports/entertainment venues.

On this episode, Jake and Dave discuss:

• BPG's Technology Implementation
• Building Vertical Integrations across the Organization
• How to start a PE Firm with discretionary funds
• Dave's experience owning a Major League Soccer Club

Links:

The Buccini/Pollin Group

BPG on LinkedIn

Virgin Hotels Nashville & New Orleans

Governor’s Camp Collection in Kenya

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Topics:

(1:45) - Introducing Dave, his background, and career

(5:46) - Why didn’t you take the easy route and go work for your father at 25? Why start your own company?

(9:25) - Why does everyone say hotels are so hard?

(12:01) - What’s the RevPar index?

(12:58) - What were some early challenges or mistakes you made early on in your career?

(15:13) - Do your culture initiatives flow down to the hourly worker level?

(17:35) - What kind of technology have you built into your management company?

(20:24) - How do you pursue management contracts?

(23:20) - What have you learned as an owner where you’re not managing the property?

(26:00) - Is the Hilton F&B model dead?

(32:41) - Can you walk us through an entire deal?

(41:48) - What was your process for starting a PE firm with discretionary funds?

(47:58) - What was the most surprising thing you learned in this process?

(49:35) - How did you capitalize Fund #1?

(50:34) - Can your Funds invest in a deal you sponsor?

(52:28) - Are you a better investment shop due to your vertical integration?

(54:09) - What was the thought behind starting so many companies within your brand?

(55:59) - What goes through your mind when thinking you need to bring another service in-house?

(57:23) - What was your experience during Covid?

(59:17) - What are you seeing for Office right now?

(1:03:18) - How did you get into the Major League Soccer business?

(1:09:12) - How do you make money in the MLS?

(1:10:49) - What is your favorite hotel?

On this episode, Jake and Rob discuss:

• How Lowe was able to build such a massive organization
• Converting Office to Residential
• Developing Hotel Properties
• Incentivizing teams and developing culture

Links:

Lowe - Beyond Buildings

Rob on LinkedIn

CoralTree Hospitality

Ivy Station in Culver City, CA

Terranea Resort in Palos Verdes, CA

La Coorniche Hotel, France

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Topics:

(2:36) - How did Lowe build such a massive footprint? (10:04) - What were some early insights you had on the importance of people and place?

(14:23) - What are your thoughts on Office as an asset class?

(16:25) - Are you looking to convert any of your Office buildings?

(18:46) - What are some things you look for when determining if you can convert an Office to Residential?

(20:32) - Have you ever considered getting Hotel, Office, and Resi within one building?

(22:58) - How do your local teams integrate into the larger organization?

(24:02) - How do you capitalize your deals?

(25:06) - What’s been your experience working with your brother and how did you end up in the business?

(28:06) - Did you have any hotel experience before you stepped into the role?

(29:16) - Is developing hotels in today’s market more difficult?

(32:41) - Do you prefer to buy assets from a bank or to develop from the ground up?

(33:18) - Developing the Terranea hotel in California

(49:27) - How did you approach F&B at the property?

(51:02) - Thoughts on entitlement

(52:27) - How did Destination Collective come about?

(1:02:06) - Would you consider buying management companies with your new company?

(1:03:58) - What contracts are you looking for right now?

(1:05:20) - How do you think about incentivizing?

(1:08:45) - How much time do you spend developing culture?

(1:11:14) - What is your favorite hotel?

On this episode, we discuss:

• How Bashar got started in the Hospitality space
• Building hotels
• Focusing on design and the human touch
• Making the magic!
• Biggest pet peeves
• How to build an enduring hospitality brand

Links:

Bashar on LinkedIn

Bashar on Instagram

Connect with Bashar here

Soho Warehouse, NYC

Proper Hotel Austin

Remo Workspaces

Aman Hotel in Tokyo

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Topics:

(1:59) - Bashar’s background and career

(5:01) - Does ‘cool’ come naturally?

(8:30) - Did you ever fall victim to the shift away from hospitality in favor of shock & awe?

(11:30) - How do you train someone to be hospitable?

(14:32) - What was your role when joining provenance?

(16:45) - How do you think about programmatic ventures today?

(25:39) - Is there a minimum or maximum size when you’re looking for hotels to acquire or develop?

(26:50) - How do you underwrite an independent hotel vs. a branded one?

(30:50) - How do you think about trends?

(32:51) - Do you see people getting tired of hotel brands and caring more about belonging?

(36:36) - A discussion on Design

(52:21) - How did you end up with a 25-room hotel in Palm Desert?

(53:47) - What’s your strategy with your Bentonville, AR hotel and what do you see for the future of these smaller markets?

(58:36) - What do you predict tent and RV hotel companies looking like in the near future?

(1:00:00) - Do you handle the F&B side of your assets?

(1:03:01) - Do you need to get into 3rd party in order to scale a management business?

(1:07:00) - What do people most often miss in the hotels you’ve stayed in?

(1:10:15) - Thoughts on exclusivity and scarcity

(1:11:40) - When you’re coming up with a new hotel, what are some must-have elements?

(1:14:55) - Are there any recent companies in the industry you find interesting?

(1:18:30) - What is your favorite hotel?

In this episode we discuss:

• Sourcing deals & developing strategy
• Leading an operating team & executing on a vision
• Hospitality trends over the next decade

Links:

Classic Hotels & Resorts

John Grossman on LinkedIn

Manka's Inverness Lodge

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Topics:

(1:51) - Introducing John & his portfolio

(4:25) - What is it about leisure and independent hotels that is attractive to you?

(6:10) - How have you avoided the franchising model after all these years?

(7:41) - How do you approach the infrastructure of your organization?

(8:29) - Why are folks who’ve come from places like Ritz Carlton and 4 Seasons a great fit for you?

(10:10) - What are your criteria when you’ve found a market you like?

(13:45) - How are you finding these properties when there are moratoriums on hotel doors?

(17:12) - How do you plan out how each hotel will look once you’ve acquired an asset?

(19:47) - How do you underwrite your deals?

(25:13) - How do you think about who the guest is going to be?

(27:48) - Who handles the design for your hotels?

(31:28) - What are you prioritizing as you set your budget?

(35:07) - What makes the best designers truly great?

(38:14) - Are you prioritizing public spaces over guest room decisions?

(41:33) - How are you creating “Moments” without focusing on the F&B side of the property?

(44:07) - Is there a variable when you’re analyzing a new investment some would find surprising?

(49:09) - Is being vertically integrated your best competitive advantage?

(52:10) - How involved are you in setting the mold of the brand narrative for the designers?

(55:54) - What are the big trends that you’re thinking about over the next 5 years?

(1:01:49) - What is your favorite hotel?

On this episode, Jake and Dupree discuss:

• The history of Woodbine's massive success
• How to create moments and places where guests want to be
• The decision to diversify assets beyond hospitality

Links:

Woodbine Development

Dupree on LinkedIn

Hotel Emma - San Antonio

Mountain Shadows Resort Scottsdale

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Topics:

(2:48) - Woodbine’s history and path to success

(10:06) - How have you diversified Woodbine’s capital partners?

(13:18) - What led to Woodbine focusing on hospitality?

(17:49) - How do you make money on a shorter time horizon when you have a partner thinking 3-4 generations down the road?

(20:36) - What do you find is the most important aspect of being able to secure a deal?

(23:32) - How did you get into the business?

(26:05) - What’s the hardest thing stepping into the business as the second generation?

(32:09) - What are some key learnings you had from your time with Trammel Crowe?

(35:09) - How do you get the most bang for your buck in projects?

(37:31) - Are there aspects of a project you refuse to compromise?

(38:30) - How do you create a moment and a place where guests want to be?

(42:12) - How did the Driscoll Hotel and Hyatt Hillcountry deals come together?

(50:37) - How do you approach raising capital for deals?

(54:56) - What is it about hotels that you and your investors are attracted to?

(57:31) - What did the capital stack for The Driscoll look like?

(1:00:27) - Do you manage the hotels yourself or do you 3rd party it?

(1:03:13) - How do you align F&B with your vision?

(1:04:47) - Do you have any tips or strategies for structuring F&B deals?

(1:06:02) - Is it not possible to build a mega resort anymore?

(1:08:15) - What do you think about 3rd party development?

(1:11:22) - What criteria are you focusing on in development deals right now?

(1:12:16) - Why are you diversifying your assets beyond hospitality?

(1:15:53) - What do you think happens to certain assets in Office?

(1:17:36) - What is your favorite Hotel?

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.

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