Matthew Baron, Founder and President of Baron Property Group, dives into the dynamic real estate markets of NYC and Miami. With over 30 years of experience, he shares his journey from his first deal to pivoting into hotel development amid crises. The discussion covers risk mitigation strategies, the evolution of Long Island City, and the importance of location in attracting residents. He also highlights the challenges of navigating union labor in NYC while transitioning to the Miami market, emphasizing the value of local partnerships and long-term ownership.

Dive into the world of hotel investing as common pitfalls are unveiled. Experience is highlighted as a vital asset in hospitality decisions. Location reigns supreme, but so does understanding customer needs. Delve into the dangers of broken business plans and cost overruns. Discover the challenges of renovations and ground-up developments that can lead to financial setbacks. Finally, learn how to maximize ROI by prioritizing practical improvements over mere aesthetics.

Avi Greenbaum, CEO of Triple Double RE, shares his entrepreneurial journey from trading baseball cards to tackling real estate. He discusses his first successful condo conversion, revealing the intricacies of financing and market trends. Avi highlights his innovative deal-making tactics, including transforming urban spaces in Delray Beach. He emphasizes the importance of adaptability in fluctuating markets and shares insights on negotiating effectively, including the art of silence. His stories are packed with lessons on resilience, opportunity, and bold strategy.

Isaac French, Founder of Experiential Hospitality, has revolutionized the micro-resort scene with his acclaimed Live Oak Lake, which he sold for an impressive $1M per key. He shares his journey of launching the project, detailing the struggles and creative marketing strategies that led to its success. The conversation dives into the unique design elements that blend Scandinavian minimalism with Texan charm. Isaac also discusses the emotional challenges of selling a hospitality venture and why naivety can be a beneficial trait for entrepreneurs.

In this episode, we dive deep into the complexities and opportunities of converting older mom-and-pop motels into modern, vibrant lifestyle hotels, particularly in resort areas. We discuss the importance of understanding the market, creative financing options, successful case studies, programming and amenities, renovation scopes and plans, and risk management.Additionally, we cover listener questions on negotiating deals, alternative financing methods, and enhancing the online presence of independent hotels.Connect & Invest with Jake:Follow Jake on Twitter: https://twitter.com/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8PwoTopics:(00:00:00) - Intro(00:02:17) - Converting Motels into Lifestyle Hotels(00:04:02) - Case Studies of Successful Conversions(00:08:53) - Market Considerations for Hotel Conversion(00:16:48) - Programming and Amenities for Modern Motels(00:19:19) - Renovation Scope and Design Tips(00:23:41) - Underwriting and Financial Considerations(00:30:06) - Q&A Session: Institutional Buyers and Revenue Potential(00:37:32) - Understanding Commission Structures in Hotel Bookings(00:37:50) - The Importance of a Compelling Website(00:39:16) - Leveraging Social Media and Influencers(00:41:40) - Outsourcing E-commerce and Revenue Management(00:42:25) - Challenges with Hotel Websites(00:46:47) - Negotiation Strategies for Buying Hotels(00:55:38) - Alternative Financing Methods(00:58:46) - Converting Motels to Multifamily Units(01:01:51) - Boutique Hotel Renovation Costs(01:06:41) - Networking and Financing in Hospitality(01:09:53) - Closing Remarks and Podcast Information

John Meadow is the founder and president of LDV Hospitality, a boutique hospitality group that was founded on his realization of the ambition to bring the dream of “La Dolce Vita,” to everyday life.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 the critically acclaimed flagship Scarpetta restaurant, followed by signature brands American Cut and Dolce Italian.This episode was originally released May 10th, 2023On this episode, Jake and John Discuss:Creating the Ultimate Dining ExperienceBuilding a Restaurant in RomeScaling LDV to a Global levelLeadership LessonsLinks:LDV Hospitality: https://ldvhospitality.com/Ralph’s Restaurant in Paris: https://www.ralphlauren.co.uk/en/global/ralphs-paris/7120Outliers 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 TwitterTake the Hospitality Investing MasterclassLearn How to Invest with DoveHillTimestamps:(00:00:00) - Intro(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 Managing Partner, Chris oversees all of the company’s development and sales activities. With East West pioneering new communities in Charleston, Denver, Snowmass, Deer Valley and Kauai, Chris works with folks from coast to coast and helps guide these destinations toward the future. From his perspective, the agenda is actually quite simple, “We build places that put people first, where the experience drives design and sustainability governs construction techniques.”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.This episode was originally released July 2023On 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 and how to make it work- Large scale resort development- Managing riskConnect & Invest with JakeFollow Jake on Twitter: https://twitter.com/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8PwoLinks: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-bayTopics:(00:00:00) - Intro(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?

Chris Pronger is a former NHL MVP who played 19 years in the league before embarking on his journey into entrepreneurship with his adult beverage business.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 2024On 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 marketCheck 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/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

In this special coaching-call episode, we deep dive into what has made Blackberry Farm a successful hospitality operation before getting into some Q&A where we discuss:- 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/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8PwoTopics:(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

Gabe has led more than $50mm of multi-family investments in metro Denver, across more than 500 apartment units in Denver, Lakewood and Aurora. Gabe is also the co-manager on over $25mm of multi-family investments (164 units) in Los Angeles.This episode was originally released October 2023On this episode, Jake & Gabe discuss: Going from Wall St. into Real EstateBuilding Generational WealthRaising CapitalExecuting Value-Add Strategies Links:Gabe on TwitterTekton Group Connect & Invest with Jake:Follow Jake on Twitter: https://twitter.com/jwurzakTake 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?