The Agility of Entrepreneurship: A ”Lone Wolf” Investor Who Built a Winning Team

In this episode, we sit down with Carrie Howder—a dog-loving, detail-oriented former paralegal turned real estate investor—who shows us what it really means to take the leap and bet on yourself. From a spontaneous start in South Boston to building a lifestyle business centered around pet-friendly short-term rentals in Maine, Carrie shares her journey of agility, grit, and resourcefulness.

Carrie walks us through how she used a 1031 exchange to level up her investments, left her paralegal career to run Airbnbs full-time, and created a niche market welcoming large dogs and their owners. She opens up about what it takes to navigate unexpected challenges—from dealing with code violations to building a trusted team—and how embracing entrepreneurship has reshaped her life.

 

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