Episode 55
2 Studios to 100 Vacation Rentals. Now Shareholder of Pavilion Vacation Rental Co | Caroline Ramos, Founder & CEO, Host and Keep · Co-Founder, Chukum USA
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Caroline Ramos spent fifteen years in corporate marketing, often the only woman in the room. Then COVID hit, she was let go, and the decision got made for her. It started with two Art Deco studios in Miami Beach. It became Host and Keep, a short-term rental investment firm operating around 100 properties across South Florida — and one of the twenty founding local companies of Pavilion, the national vacation rental company that launched in October 2026 managing more than 5,000 homes. She also co-founded Chukum USA with her husband Vinny, bringing an ancient Maya lime plaster to architects across four regions. Recorded days before the Pavilion announcement. WHAT YOU'LL LEARN → Why the growth your business can achieve is capped by how much control you can release → How to structure a partnership with a foreign manufacturer, and the three rules to follow before signing → What it actually takes to scale a short-term rental portfolio past owner-operator → The difference between working as an owner and working as an operator → How to reframe multiple ventures as projects so the load becomes manageable → Why biophilic design is reshaping what architects specify THE NEWS → On October 5, 2026, Pavilion launched as a national vacation rental company with 20 founding local companies managing more than 5,000 homes and welcoming approximately 50,000 guests each month. → Host and Keep is one of those twenty founding companies and continues to operate under its own leadership. → Pavilion is structured so the leaders of its local companies become long-term shareholders, and together with Pavilion's management team they own the majority of the business. GUEST LINKS → Host and Keep: hostandkeep.com → Email: caroline@hostandkeep.com → LinkedIn: linkedin.com/in/carolineramos → Chukum USA: chukum.com.mx → Pavilion: pavilioncollection.com CORRECTION → Vicki Lopez serves as a Miami-Dade County Commissioner, not a member of Congress. CTA → Take the free Capital Readiness Scorecard at PlungeIntoProsperity.com
Show Notes
00:00 Welcome to Episode 55 — and why the show pauses for winter 01:40 Meet Caroline Ramos: two companies, one household 02:55 Why you should keep listening 03:30 What prosperity means: freedom, and its many definitions 04:50 The boldest plunge — getting fired during COVID 06:54 Projects, not businesses: the reframe that makes two companies possible 08:39 Flow versus friction 09:35 Why growth is tied to how much control you can release 10:32 Yoga, breathwork, and the non-negotiables 12:53 Running a calendar on Vedic astrology and AI 14:57 Host and Keep begins: two Art Deco studios in Miami Beach 16:41 Vinny's role — one income, one risk, one runway 19:24 Why a business that never breaks never grows 20:09 Falling in love with Chukum in Mérida 20:48 Importing white powder from Mexico 21:03 The cold call that built a company 21:59 How the partnership was actually structured 23:05 What she'd do differently: 360s, operating agreements, exits 26:00 Apprenticeships, sweat equity, and earned ownership 29:29 The mentor who taught her mindset over business 30:20 Biophilic design and why Chukum sells itself 32:44 Americanizing an artisanal Maya craft 33:14 Mérida, Miami, Barcelona: scaling distribution 35:27 Inside Host and Keep today — and joining Pavilion 36:41 The three-part Chukum growth plan 38:36 Building an AI-forward company 41:12 Owner versus operator 42:12 The right hand behind the operation 45:14 Where to find Caroline 45:55 Your next step: the Capital Readiness Scorecard
About the Guest
Caroline Ramos spent fifteen years in corporate marketing in New York before leaving during COVID to build what she calls her projects. The first, Host and Keep, began with two Art Deco studios in Miami Beach and grew into a short-term rental investment firm operating around 100 properties across South Florida, handling acquisition, financing, monetization, and management. In October 2026 it became one of twenty founding local companies of Pavilion, a national vacation rental company managing more than 5,000 homes, structured so founders of the local companies hold equity in the parent. Her second project, Chukum USA, was born when she fell in love with an ancient Maya lime plaster in Mérida and cold-called the Mexican factory owner to bring it to the United States. She built both with her husband and co-founder, Vinny.
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