Masters of Moments

Dupree is the Managing Partner and Chief Investment Officer of Woodbine. A fully integrated real estate investment and development firm and one of the leading hospitality owners in the country, having completed over $3.6 billion in hotel investments and developed over 11,000 keys across branded and independent projects.  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   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 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?

Masters of Moments involves conversations with top entrepreneurs and business leaders about hospitality, Real Estate investing, and company building. We explore the ideas, strategies, and approaches that brought them to where they are today. 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. Follow Jake on Twitter Take the Hospitality Real Estate Investing Masterclass Subscribe to the show on YouTube