Shay Ashford aka Chitownhomestead
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Shay Ashford, known to many as Chitownhomestead, was born and raised in Chicago, Illinois. Eager to escape her circumstances after high school, she enlisted in the United States Marine Corps despite failing the ASVAB exam twice. Her determination propelled her through a remarkable 24-year military career, serving in the Army, Air Force, and Navy, and navigating life independently across three continents.
Between deployments, Ashford pursued a career in modeling and acting, including a role as 'Clyde' on the reality show 'Bounty Girls Miami.' Through the ups and downs, she maintained excellent credit, which later became the foundation for her success in real estate. Today, she is a thriving entrepreneur specializing in tiny houses, having acquired four properties without relying on traditional loans.
IN THIS EPISODE YOU’LL LEARN:
- How Shay Ashford overcame early setbacks, including failing the ASVAB twice, to join the Marines and build a 24-year military career.
- That it's possible to acquire multiple real estate properties using only your own money and credit, with no hard money loans.
- How to get started in real estate investing without falling into debt or relying on outside lenders.
- Why self-education and doing your own research are the most powerful tools for any entrepreneur.
- How Shay transitioned from a struggling actress to a successful tiny house real estate investor.
- Why you should never let anyone tell you what you can't achieve, no matter where you start.
- How to maintain excellent credit even during financially unstable times to unlock future opportunities.
- That traveling to multiple countries as a single Black woman without speaking the language is achievable and empowering.
- How Shay's philosophy of 'if you want something done right, do it yourself' fueled her independence.
- Why tiny houses offer a practical path to homeownership and financial freedom for aspiring entrepreneurs.
about the show
Women In Power is an entrepreneur TV series featuring female entrepreneurs, CEOs, founders, and industry leaders who are building companies, leading teams, and creating impact in their industries.
Each episode gives viewers a closer look at the real stories behind these women’s success, including the challenges they faced, the decisions that shaped them, and the leadership lessons they learned along the way. The series highlights women who have built businesses, broken barriers, grown brands, and created opportunities for others through their work.
Women In Power was created to spotlight female business leaders whose stories deserve to be seen and heard. From early setbacks to major breakthroughs, each episode shows the journey behind the title, the business, and the public success.
For viewers, the show offers inspiration, practical insight, and a deeper look at what it takes for women to lead, grow, and succeed in today’s business world. For featured guests, it provides a platform to share their story, build authority, and inspire the next generation of female entrepreneurs and leaders.
