Debbi DiMaggio shares her 35-year real-estate journey, mindset strategies, and how AI & authenticity help agents and investors thrive in any market.
In this episode of RealDealChat, Jack Hoss sits down with Debbi DiMaggio — luxury real-estate icon, author, speaker, and coach at CoachWithDebbi.com — to unpack the habits, mindset, and authenticity that built her 35-year career.
Debbi reveals how she launched a brokerage during the 2009 recession, built lasting client relationships through transparency, and now teaches agents and investors how to create freedom using systems, collaboration, and AI.
You’ll learn why mindset beats the market, how to thrive through downturns, and why being yourself is the ultimate business advantage.
In this conversation:
- How Debbi turned a recession into opportunity (launching Highland Partners in 2009)
- What 35 years in real estate taught her about persistence & mindset
- How social media & collaboration create sustainable deal flow
- Her advice for working with flippers, investors & high-net-worth clients
- Why authenticity & storytelling beat any sales script
- How BNI & networking build referral pipelines
- Charity & community as real-world lead-generation tools
- AI’s role in writing listings, marketing, and even merchandise design
- Inside her upcoming book Mindset in Motion and Foundation for Success program
📘 Learn more or schedule coaching → CoachWithDebbi.com
💡 Want to scale your investing business with AI and automation? Visit https://realdealcrew.com
Call to Action: Learn more at https://realdealcrew.com
Timestamps
00:00 – Debbi DiMaggio on authenticity & a 35-year career
01:00 – How she entered real estate & why mindset matters
03:00 – Lessons from recessions & turning negatives into positives
05:00 – Why mindset in motion creates momentum
07:00 – The most unique market in 35 years & how to adapt
10:00 – Coaching new and seasoned agents to collaborate not compete
12:00 – Networking through BNI & building trust through referrals
14:00 – Honesty and ethics when working with flippers and wholesalers
17:00 – Serving high-income clients with education & transparency
19:00 – Charity as a business and mindset builder
22:00 – Be your authentic self — how it changes everything
24:00 – Balancing work and life as a “work-from-anywhere” agent
26:00 – Helping seniors through workshops and downsizing seminars
29:00 – Coaching tips for confidence & authentic marketing
30:00 – Rapid fire: truths, books & AI as a game-changer
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