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

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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?