Sean Hehir, CEO of Trinity Investments, shares his extensive expertise in hospitality investment. He discusses his journey from Botswana to Hawaii, emphasizing the importance of adaptability and relationship-building in the luxury hotel sector. Sean highlights the execution of $500 million in renovations, strategies for raising capital, and the significance of a 'no-asshole culture' within teams. He also examines evolving investment opportunities post-COVID and the critical role of partnerships in navigating the complex hospitality investment landscape.

We're at the start of a new Real Estate cycle! In today's episode, we discuss how to raise capital during tough times. Enjoy!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(00:02:32) - 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

Dev Motwani serves as Managing Partner of Merrimac Ventures, a Fort Lauderdale-based real estate firm focusing on value-added investment and development opportunities. Property types owned and operated include hotels, condos, retail, office, and rental apartments primarily in South Florida but also throughout the United States.On this episode, Jake and Dev discuss:Growing up in the family hotel businessHow to build successful partnershipsCreating long-term investment structuresLinks:Dev on LinkedInMerrimac VenturesSix Senses Douro ValleyConnect & 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(00:02:00) - 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?

As Co-CEO, Rob Lowe focuses on operations both at the corporate level and across its real estate activities.  Additionally, Rob and Mike co-chair the firm’s wholly-owned hospitality affiliate, CoralTree Hospitality Group. He is a past Trustee and President of the Palisades Presbyterian Church, is currently on the Board of Managers at the Palisades-Malibu YMCA and is an active member of Urban Land Institute. On this episode, Jake and Rob discuss:How Lowe was able to build such a massive organizationConverting Office to ResidentialDeveloping Hotel PropertiesIncentivizing teams and developing cultureLinks:Lowe - Beyond BuildingsRob on LinkedInCoralTree HospitalityIvy Station in Culver City, CATerranea Resort in Palos Verdes, CALa Coorniche Hotel, FranceConnect & Invest with Jake:Follow Jake on TwitterTake the Hospitality Investing MasterclassLearn How to Invest with DoveHillTopics:(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?

Chris Tourtellotte serves as a Managing Director of LaTerra. Chris is responsible for overseeing the Development group, sourcing and closing new acquisitions, sourcing debt and equity for LaTerra’s projects, and growing LaTerra’s apartment and mixed-use development platform, which currently includes over 3,000 apartment units under construction or in the pipeline.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/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8PwoTopics:(00:00:00) - Intro(00:02:52) - 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?

Atit Jariwala is a real estate executive who has been involved with real estate management and investment his entire life. As a partner and co-founder of several real estate companies, Atit has been involved in acquiring, developing, and managing dozens of properties across the United States. In total, Atit has been involved in acquiring and developing over $2.5 billion of real estate throughout the U.S. directly as a principal.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:BridgetonAtit on LinkedInMarram MontaukConnect & 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(00:02:32) - 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?

Bard Kligerman is a seasoned real estate developer with over two decades of experience. Co-founding CT Realty Trust (CRT) in 2009 with his father Robert, Bard has led the firm to invest over $220M in a variety of real estate ventures including single-family communities and multifamily apartments throughout Connecticut. Under his leadership, CRT has become a key player in the local real estate market, focusing on in-house management and development.Links:CT Realty TrustBard on LinkedInConnect & 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(00:02:32)- 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?  

On today's episode we deep-dive into structuring Co-GP Deals in an inside look at our Group coaching calls. Enjoy!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(00:01:24) - 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 economicsDisclaimer: This content is intended for entertainment purposes only. This is not financial or investing advice and should not be considered as such.

Scott is responsible for strategic direction, sourcing investment opportunities, capital markets and operations for the firm.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 2023On this episode, Jake & Scott discuss:Important retail trends that will shape the next decadeThe science of placemakingThe opportunity for OfficeWorking with Family Office InvestorsBuilding Torose EquitiesConnect & 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 Links:Torose EquitiesScott on LinkedInAssembly Row BostonEnnet 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?

Roundhouse is a fully integrated developer and operator of multifamily housing. Starting with a single condominium purchased amidst the financial crisis in 2009, we have since developed and acquired a portfolio of over 5,000 multifamily homes.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 dealsAvoiding competing with institutional capitalStructuring deals for acquisitions vs. developmentsThe advantages of being vertically integrated -Casey's 6-month sabbatical and how to have your company be successful without youConnect & 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  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?