James Curnin, CEO and founder of Clara Homes, discusses risks in building spec homes, characteristics of a great contractor, reinventing luxury apartment living in Bay Harbor, and sourcing deals in Miami and Los Angeles.

Bryson is responsible for the overall strategic direction and executive management of Reaume Richardson. His knowledge was built from the ground up, as he worked in the trades for half a decade before moving into executive management. 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?

Sean O'Dowd built Scholastic Capital in order to buy SFR homes in elite school districts. 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  

Daniel has more than forty years of specialized experience worldwide in hospitality-related: real estate appraisals, economic feasibility evaluations, investment counseling, asset management, receivership, and transactional services of hotels, resorts, conference centers, casinos, mixed-use facilities, spa & wellness properties, and timeshare/fractional ownership properties. 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?  

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. 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?

Jamal "Monster Mash" Mashburn played 12 years in the NBA and was an All-Star who averaged 19 points over his career. In his post-NBA life, Jamal has built an impressive portfolio of investments that include restaurants, car dealerships, hospitality, waste management and transportation.  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?

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 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?

Greg Friedman, CEO of Peachtree Hotel Group, discusses building Peachtree, the appeal of hospitality as an asset class, vertical integration, making money buying debt, learnings from previous cycles, managing reputation in a debt environment, the importance of managing P&L, holding investment committee meetings on Fridays, touring assets, and investment trends in the hospitality industry.

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.  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?

Dev Motwani, Managing Partner of Merrimac Ventures, discusses his upbringing in the family hotel business, meeting Donald Trump, and acquiring a full city block of real estate. They also talk about raising capital, key characteristics of land sites, working with LPs, and investing in other parts of FL.