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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:From Corporate to Real Estate Titan: Ashley transitioned from clinical research to real estate, scaling across flipping, rentals, and large multifamily acquisitions.
Conference Connect's Purpose: Addressing inefficiencies in the conference industry, the platform empowers attendees, vendors, and organizers to connect meaningfully and transparently.
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.
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.
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.
Negotiation Is Human: Face-to-face communication adds context, energy, and emotional intelligence—crucial in a world trending digital.
Own Your Mistakes: Both Derek and Ashley reinforce that accountability is a superpower in investing and in life.
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.
00:00 – 03:00 – Football banter and intros
03:00 – 07:30 – Ashley’s journey into real estate
07:30 – 13:00 – What is Conference Connect and why it matters
13:00 – 18:00 – The event industry, vetting speakers, and vendor visibility
18:00 – 24:00 – Why in-person events are irreplaceable
24:00 – 28:30 – Negotiation in-person vs. online
28:30 – 33:00 – Real-life negotiation wins and emotional influence
33:00 – 37:30 – The Only Woman in the Room – the story behind the book
37:30 – 41:30 – Ashley’s market outlook on multifamily real estate
41:30 – 46:00 – Accountability, vetting operators, and learning from failure
46:00 – 47:16 – Final thoughts, resources, and where to follow Ashley
#RealEstateInvesting #MultifamilyRealEstate #AshleyWilson #ConferenceConnect #WomenInRealEstate #NetworkingMatters #InPersonEvents #RealEstateCoaching #TheOnlyWomanInTheRoom #NegotiationSkills #DerekDombeck #GenerationsOfWealth #RealEstateEducation #InvestorMindset
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:From Corporate to Real Estate Titan: Ashley transitioned from clinical research to real estate, scaling across flipping, rentals, and large multifamily acquisitions.
Conference Connect's Purpose: Addressing inefficiencies in the conference industry, the platform empowers attendees, vendors, and organizers to connect meaningfully and transparently.
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.
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.
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.
Negotiation Is Human: Face-to-face communication adds context, energy, and emotional intelligence—crucial in a world trending digital.
Own Your Mistakes: Both Derek and Ashley reinforce that accountability is a superpower in investing and in life.
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.
00:00 – 03:00 – Football banter and intros
03:00 – 07:30 – Ashley’s journey into real estate
07:30 – 13:00 – What is Conference Connect and why it matters
13:00 – 18:00 – The event industry, vetting speakers, and vendor visibility
18:00 – 24:00 – Why in-person events are irreplaceable
24:00 – 28:30 – Negotiation in-person vs. online
28:30 – 33:00 – Real-life negotiation wins and emotional influence
33:00 – 37:30 – The Only Woman in the Room – the story behind the book
37:30 – 41:30 – Ashley’s market outlook on multifamily real estate
41:30 – 46:00 – Accountability, vetting operators, and learning from failure
46:00 – 47:16 – Final thoughts, resources, and where to follow Ashley
#RealEstateInvesting #MultifamilyRealEstate #AshleyWilson #ConferenceConnect #WomenInRealEstate #NetworkingMatters #InPersonEvents #RealEstateCoaching #TheOnlyWomanInTheRoom #NegotiationSkills #DerekDombeck #GenerationsOfWealth #RealEstateEducation #InvestorMindset