#147 Mastering Short-Term Rentals: Building Financial Freedom and Time Flexibility with Madeleine Raiford-Holland

Kyrie and Madeleine dive into the realities of balancing motherhood and entrepreneurship, with Madeleine sharing how her journey as a mom led her to launch a successful short-term rental business. What started as a single property soon grew into a portfolio of 16 properties in six months, and ultimately into a coaching business where she helps other families achieve financial and time freedom. She emphasizes the importance of systems, automations, and strategic hiring to free up time and ensure business success.

Their conversation explores the business side of short-term rentals, including how to find top-tier properties, navigate market saturation, and leverage automation for remote management. Madeleine breaks down the process of identifying the best-performing markets, securing financing, and furnishing properties efficiently. She also highlights the tax benefits and passive income potential of short-term rentals, sharing success stories of clients who have used them to build financial independence.

Madeleine and Kyrie discuss the strengths women bring to the short-term rental space—attention to detail, hosting skills, and multitasking—and how investing in real estate can be an empowering path for mothers seeking flexibility. They also touch on Madeleine’s transition from active property management to coaching, where she now guides others through self-directed courses, live workshops, and high-level mentorship programs.

 

Find Madeleine: @madeleineraifordholland

https://www.madeleineraifordholland.com/

 

Find Kyrie: @theconfidentmompreneur

www.theconfidentmompreneur.com