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Conversations with Tara Haynes

Today we’d like to introduce you to Tara Haynes.

Hi Tara, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
I didn’t step into real estate the traditional way. My journey began during a season of recovery from illness, when I was reevaluating what direction, my life should take. At the time, I was volunteering three to four mornings a week at my church’s food pantry, giving back to the community while searching for clarity.

Through that period, I worked with a life coach who encouraged me to combine my professional background in law, litigation, and real estate operations with service. That advice led me to Vertical Real Estate, where I volunteered my expertise in all thing’s real estate. Post‑closing, title, bank‑owned properties, and complex litigation issues. Speaking with clients came naturally to me, and before long I became the owner’s shadow — learning the business hands‑on for nearly a year and a half.

Inspired by that experience, I earned my real estate license and partnered with her for another year. Eventually, after a brokerage split, I co‑founded a real estate firm with a colleague and my then‑partner, stepping into ownership and leadership. That transition marked the beginning of my career as both a broker and entrepreneur, blending my litigation expertise with a passion for helping people navigate the housing market. In 2023, I stepped away from owning a brokerage, after I experienced a season of personal loss while also fostering children. Those experiences reshaped my priorities and gave me a deeper appreciation for balance, community, and human connection.

Today, I am proud to serve as an Associate Broker and Property Manager at a successful local brokerage that truly aligns with who I am and the values I want to see represented in the community. In this role, I assist other agents with inspections and showings, manage properties with care and compliance, and continue to bring my lifestyle‑driven approach to real estate — helping clients not just with transactions, but with the neighborhoods and communities that shape their lives.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Not at all. I was ill‑prepared to be a business owner, much less to run a brokerage. I always had the best of intentions in everything I did, but I fell short many times. I struggled mentally with feeling like an imposter — like I wasn’t equipped to lead anyone to success because I was still figuring it out myself.

We opened in April of 2019, and then in March of 2020 COVID happened. Suddenly, we grew really big, really fast, and we weren’t equipped for that kind of scale. There was a lot of miscommunication, mismanagement of funds, and not having things in writing or clearly documented. Those gaps created challenges that taught me hard but valuable lessons about leadership, structure, and clarity.

Even through those struggles, I kept showing up, learning, and growing. That season shaped me into the professional I am today — someone who values transparency, consistency, and the importance of building systems that support both clients and colleagues.

Thanks for sharing that. So, maybe next you can tell us a bit more about your work?
My approach is lifestyle‑driven. I don’t just help clients buy or sell a property — I help them find a home that fits their routines, values, and community connections.

In Hampton Roads, every area has its own personality: Chesapeake offers family‑friendly communities, Norfolk has vibrant urban living, and Virginia Beach blends coastal lifestyle with convenience. I take the time to learn what matters most to my clients — whether it’s schools, commute times, pet‑friendly rentals, or access to military bases — and then show them around the area so they can find a place that truly fits their lives.

That lifestyle focus, combined with my background in law, litigation, and complex closings, means I bring both heart and expertise to the table. Clients know I’ll advocate for them, simplify the process, and help them see the bigger picture of building a life in Hampton Roads.

What sort of changes are you expecting over the next 5-10 years?
Technology will continue to transform how we search for homes, market properties, and manage transactions. Virtual tours, AI‑driven search tools, and digital closings will become more common, and clients will expect faster, more streamlined processes.

But at the end of the day, you cannot replace human connection — and that remains true. Buying or selling a home is one of the most personal and emotional decisions people make. No matter how advanced the tools become, clients still need someone who understands their lifestyle, their neighborhood, and their unique goals.

I believe the biggest shift will be balancing innovation with authenticity: using technology to make the process easier, while keeping the focus on relationships, community, and trust. That’s where I see my role — blending modern tools with a lifestyle‑driven, human approach to real estate in Hampton Roads.

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