Masters of Moments

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.

Homi Vazifdar is Founder and Exec. Director of the Canyon Group, a boutique private equity company, based in Larkspur, California just of north San Francisco. The Canyon Group, which was co-founded by Vazifdar in 2005, owns and/or develops ultra-luxury resorts in exotic destinations around the world. 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:CanyonHomi on LinkedIn 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:(00:01:55) 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?

Mauro began his career in the food and beverage industry, working in Michelin-starred restaurants across Europe for a 15-year period. Having worked in Hong Kong, London, Paris, Lisbon, Rome, Milan, the Maldives, Mauritius, and the Bahamas, he has a wealth of international experience with luxury institutions and brands. 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?

Sean is a Principal and Managing Partner of Trinity Investments as well as the President and Chief Executive Officer of Trinity Investments and Trinity Fund Advisors LLC. He oversees the firms’ investment activities, including sourcing and executing investment opportunities, formulating investment strategies, and structuring acquisitions and dispositions.  Prior to joining Trinity, Mr. Hehir worked for HVS International. 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?

NewcrestImage is a privately held family office investment firm based in Dallas, Texas, with an extensive portfolio of diversified real estate assets and alternative investments. They've conducted 277 hotel transactions and $2.7 billion in real estate transactions across 148 cities. 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?

Selling weed is in Brady Cobb's blood. Using shrimp boats and a suntan lotion company as a cover, his father, Bill Cobb, ran one of the country's largest pot smuggling enterprises in the 1980s, until the federal government arrested him and shut down the $300 million ring during "Operation Sunburn." 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 Pestronk is co-founder of Post Brothers, a real estate investment, development, and management company with singular and unique expertise in urban real estate development. 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?