Ashley Wilson builds more than businesses—she creates opportunities. From growing Bar Down Investments to mentoring through Apartment Addicts and connecting professionals via Conference Connect, Ashley empowers others to achieve financial freedom, gain confidence, and pursue their goals in industries often dominated by others.

Ashley Wilson is a 2024 Main Line Parent Women of Influence Award Winner

Main Line Parent’s Women of Influence Awards celebrate exceptional women making significant impacts in our community. Each Women of Influence Award Winner has committed to support Family Focus Media’s core values. Together, we are committed to foster a sense of belonging and empowerment for all families. All backgrounds, races, genders, and sexual orientations are welcome and safe with us.

Beyond the awards, our Women of Influence Luncheons and Speed Networking Night attendees come together as our Women of Influence Network, a community fostering connections, collaboration, and mutual support. 

Breaking Barriers and Building Bridges

Ashley Wilson has never been afraid to stand out. A best-selling author, real estate investor, tech entrepreneur, and founder of seven companies, she thrives in male-dominated industries by leaning into what makes her different. “I rarely notice that I’m the only woman in the room,” she says. “Instead of feeling insecure about it, I leverage the difference—it makes you more memorable.”

Ashley is the author of The Only Woman in the Room: Knowledge and Inspiration from 20 Women Real Estate Investors, a book born from her experience attending a real estate conference where women made up fewer than 4% of the attendees. She has since turned that inspiration into three growing companies—Bar Down Investments, Conference Connect, and Apartment Addicts—each designed to open doors for others.

Updates Across Her Brands

Over the past year, Ashley’s ventures have continued to gain momentum. At Bar Down Investments, she and her partners are preparing to close on a 351-unit apartment complex in Dallas-Fort Worth, a development deal that expands their growing portfolio of large-scale properties.

Apartment Addicts, her mentorship program, has celebrated multiple student successes this year, with members purchasing their own apartment buildings and beginning their journeys as investors.

And Conference Connect, her platform for event organizers, speakers, and attendees, has welcomed over 180,000 visitors to its site, providing visibility and access to diverse voices in the conference space. The platform not only offers ticketing services but also helps market events at no upfront cost—earning only through affiliate sales. In the past year, Ashley has also launched a webinar series for the events industry and is preparing to introduce a crowdfunding option, allowing individuals to invest directly in the company’s growth.

A Journey Driven by Freedom and Family

Ashley’s entrepreneurial drive has always been rooted in her desire for freedom and flexibility. “Growing up, my parents were always there for me and my brother,” she reflects. “It was so important to me that when I started pursuing a career, I sought opportunities that allowed me the freedom to be there for my family whenever they needed me.”

As a mother of two daughters, she has also made it her mission to model what financial independence and self-determination look like. “I want to carve a path for other women looking to pursue financial freedom,” she says.

Overcoming Challenges with Grace

From the early days of navigating male-dominated rooms to managing the ups and downs of start-up life and economic cycles, Ashley is no stranger to challenges. But her outlook is one of resilience. “I decided very early on that these challenges also provide experience,” she says. “I sometimes believe I’m living the real-life Slumdog Millionaire story, where every challenge has come full circle and provided more value than headache.”

Giving Back and Lifting Others

Ashley is equally committed to giving back. Properties owned by Bar Down Investments regularly partner with local and national organizations, including women’s and children’s charities. She continues to speak at women’s real estate events and makes it a personal goal each year to give more than the year before. “If we all took this approach, imagine how impactful we could be. We literally could change the world,” she says.

Looking Ahead

Ashley’s vision for the future is clear: to keep growing her companies while staying true to her mission of empowerment. She hopes to see Bar Down Investments continue to expand its portfolio and provide more people with access to wealth-building opportunities. Through Apartment Addicts, she aims to guide even more students into successful ownership and long-term financial independence. And with Conference Connect, Ashley envisions a platform that transforms how people discover, attend, and connect at events worldwide. No matter the venture, her driving goal remains the same—to create opportunities, open doors, and inspire others to define success on their own terms.