#97 - What Luxury Real Estate Really Means and How to Sell Your Home for More with Debbi DiMaggio

Path To Passive: Real Estate Investing For Technology Professionals

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Is luxury real estate really just about the price? In this episode, Steven Arita sits down with Debbi DiMaggio, real estate veteran, coach, and author, to unpack what truly defines luxury in today’s market. With over 35 years of experience in the Bay Area, Debbi shares how service, presentation, and emotional connection matter far more than price tags. She talks about working with celebrity clients, guiding sellers through home prep years in advance, and helping buyers find homes that feel just right. From the evolution of buyer expectations to navigating economic shifts, Debbi offers practical advice, heartfelt stories, and a reminder that success in real estate and life often comes down to mindset, timing, and showing up for others.
Debbi DiMaggio is a seasoned real estate expert with over 30 years of experience in the San Francisco Bay Area and Los Angeles markets. Known for her client-first approach, strong negotiation skills, and deep knowledge of residential real estate, she’s worked with everyone from first-time buyers to longtime homeowners. As a Seniors Real Estate Specialist® (SRES®), she also supports older clients with care and clarity during major life transitions. Debbi is the host of the podcast “Mastering The Art of Real Estate,” a mentor and coach, and the author of multiple books, including The Art of Real Estate and 52 Ways To Achieve Success in Real Estate. She’s also contributed to local publications as a trusted editorial voice. Outside of real estate, Debbi is passionate about giving back, especially through her work with UCSF Benioff Children’s Hospital and Race to Erase MS, and finds joy in travel, writing, and connecting with people from all walks of life.
Connect with Debbi:
Website: https://debbidimaggio.com/
Tune in to her podcast: https://tinyurl.com/4ncvnz66
Grab a copy: https://debbidimaggio.com/books
Episode highlights:
(0:00) Intro
(3:16) Debbi’s start in real estate and family background
(6:30) From LA to SF: early career in rentals
(8:37) Working with Hollywood clients
(12:48) Defining luxury: service vs. price point
(19:33) Preparing a home for sale and buyer profiles
(31:16) Buyer psychology and common missteps
(40:40) Helping distressed sellers and emotional impact
(44:51) Starting a firm during the 2009 recession
(49:22) On serving the community
(56:14) Giving back through Children’s Hospital
(58:54) Writing books and launching a skincare brand
(1:01:35) Running a marathon on mindset alone
(1:04:47) Where to connect with Debbi and more
(1:06:10) Outro
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