Thinking about dipping your toes into entrepreneurship but not sure where to start? This one’s for you.

In today’s episode, Megan Tobler sits down with Madeleine Raiford-Holland, a Self StartHER who left her steady corporate job behind to build a thriving business in the short-term rental space—all without owning a single property at first.

We talk about what it really looks like to bet on yourself, how to enter the Airbnb game without a ton of upfront cash, and why a strong “why” can carry you further than the perfect business plan ever could. Madeleine breaks down how she built her business one rental at a time, her smart strategies for getting bookings outside of Airbnb, and how she turned her passion into a coaching program for other women ready to start.

Whether you're craving more freedom, dreaming of a side hustle, or ready to take your first step into entrepreneurship, Madeleine's story will show you what’s possible when you stop waiting for perfect and just start.

Learn more about Madeleine:

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