From Tactical to Transformational: Real Estate, Conferences & Conversations with Ashley Wilson

📋 Episode Summary:

In this powerhouse episode, real estate mogul and entrepreneur Ashley Wilson joins Derek Dombeck for a candid, unscripted conversation that dives deep into multifamily real estate, the true value of in-person networking, and her mission to bring transparency and innovation to the conference world. Ashley unpacks her journey from clinical research to managing over $160M in real estate assets, co-founding Apartment Addicts, and launching the platform Conference Connect. The discussion also tackles the current multifamily market, negotiation dynamics, personal accountability, and the future of live events. Whether you're a new investor, a seasoned operator, or someone passionate about personal growth—this episode hits on all cylinders.

💡 Key Takeaways:

1. From Corporate to Real Estate Titan: Ashley transitioned from clinical research to real estate, scaling across flipping, rentals, and large multifamily acquisitions.

2. Conference Connect's Purpose: Addressing inefficiencies in the conference industry, the platform empowers attendees, vendors, and organizers to connect meaningfully and transparently.

3. Power of In-Person Events: Strategic, high-value connections often emerge in informal moments—like dinners or hallway chats—not through Zoom or YouTube alone.

4. Multifamily Market Outlook: Ashley shares why the market's current turbulence is far from over, and why regulation, oversight, and education matter more than ever.

5. Women in Real Estate: Her book The Only Woman in the Room uplifts female voices in the space and helps break barriers in a traditionally male-dominated industry.

6. Negotiation Is Human: Face-to-face communication adds context, energy, and emotional intelligence—crucial in a world trending digital.

7. Own Your Mistakes: Both Derek and Ashley reinforce that accountability is a superpower in investing and in life.

🎧 Why You Should Listen:

• You're in or considering commercial/multifamily real estate.

• You’ve ever been burned by flashy “gurus” and want the real, no-BS truth.

• You want to learn how conferences can be leveraged more strategically.

• You’re a woman navigating a male-dominated industry (or want to support those who are).

• You believe in the power of networking, relationship capital, and personal accountability.

• You want to level up your negotiation game with emotional intelligence and presence.

⏱️ Time Stamps (Total Length: 47:16)

• 00:00 – 03:00 – Football ban