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.  Links:Woodbine DevelopmentDupree on LinkedInHotel Emma - San AntonioMountain Shadows Resort Scottsdale  Connect & Invest with Jake:Follow Jake on TwitterTake the Hospitality Investing MasterclassLearn 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 Trammell Crow?(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?