In this conversation, I sit down with Debbi DiMaggio, a real estate professional with more than 35 years of experience, to explore the strategies, relationships, and mindset shifts that have helped her build a thriving referral-based business. We discuss everything from trust, networking, and client experience to delegation, virtual assistants, and the lessons she has learned over decades in the industry. Debbi also shares insights from her Mindset in Motion framework, stories from her career, and practical advice for real estate entrepreneurs who want to build a sustainable business rooted in relationships, integrity, and long-term growth.
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In this conversation, I sit down with Debbie DiMaggio to talk about what it really takes to build a long-standing, referral-driven real estate business. Debbie shares how she has grown through 35 years in the industry, why integrity and communication matter more than almost anything else, how professional networking has shaped her referral engine, and what she has learned about support, mindset, and persistence along the way. If you are a real estate entrepreneur who wants to build a business rooted in relationships, reputation, and long-term leverage, this conversation is full of grounded, practical wisdom.
Hello everyone, I’m Adrienne Green, and today we’re here with Debbie DiMaggio. Debbie, thank you so much for being here with me today.
Thank you so much for having me. Excited to be here.
Debbie, can you give us a quick snapshot of your real estate business today? Who you serve, what markets you focus on, and how your business is structured?
Sure. I have been practicing real estate, this dates me, for 35 years. I started in my late 20s working in rentals in San Francisco before I launched into sales in the East Bay. When I say the East Bay, we are 20 minutes from San Francisco. A lot of people move to San Francisco, and then when they start to have families and decide they want a less urban life, they move over to the East Bay. There are a few different places. I look at San Francisco Bay Bridge right now, and it’s still city-ish, but people move here for the community and the schools. The whole East Bay is where I practice.
I also practice in the West Hollywood, Beverly Hills area. After my kids grew up and I became an empty nester, I do not golf. I do not have hobbies like that. I don’t play bridge. I decided, I think I’ll expand to LA because I love LA and I love real estate. I have freedom in that way. My son, who works with us, is in LA right now working one of our deals down there. Real estate is wonderful, and technology has helped us tremendously to be able to have the freedom that you speak about.
Our structure is my husband and I started working together in real estate before we were even married. We worked in rentals in San Francisco, started a leasing department there, and that gave us flexibility to raise our daughter and later our son. We were able to time-share the job. He would go, then I would go, and we bounced around. We were lucky to have my parents for support.
When we moved over and started to raise the family, we moved over to Piedmont and got involved over here in sales. We’ve always worked together. Then our son started working with us during COVID. It was kind of a COVID fallout. He was going to go back to Colorado where he went to school, then he got his license and decided to work with us in real estate. That’s been wonderful.
We actually launched a company in 2009 during the recession. Someone said to us, “It’s a recession,” and we were like, “Yeah.” But this had already happened. We were already in motion to launch this company, and so we did it. Speaking with my book, Mindset in Motion, we didn’t really think about it being a recession. We just had a plan, and we were going to execute. It wasn’t top of mind. It was, “This is what we’re going to do, and we’re going to do it.”
We had Highland Partners from 2009 to 2020. Then we merged with Orchard to be part of a bigger company. Now that we’re part of that, we’re partners in the company. However, my husband, my son, and I are DiMaggio Betta Group, and that’s how we work.
Fabulous. With this 35-year career, I understand that trust and long-term relationships are one of your core values. What does that look like operationally, and how do you protect that reputation as you grow?
Markets are different. People are different in different markets. But one of the things that holds true in real estate for Realtors is that the only thing we have is our integrity. Fair and honest dealings, always being above board. Our community in real estate is super small. You get to know people, not only now with all the conferences we go to and Zoom and the internet and all the networking groups that I’m part of. It’s a really small network. When you’re at the higher end, it gets really small.
You’re known. There are some big people out there who are known for not being good people. It surprises me day in and day out how they’re still getting publicity. You can watch and hear their story and what they’ve done, and they’re being sued, but they’re still out there. Integrity is what we have. That’s what keeps us in the long game.
People know that they will get an honest answer. They might not like the answer if they want to sell their house and we give them the price, but the market speaks. What makes it easier for us as agents is that when the market speaks, it speaks to the buyer, the seller, the agents. It’s out there. It’s public record. I can’t change the data. I can share it with you, and I can peddle it softly to you, but the data is there.
The best thing we have, the only thing we have, is our integrity. That’s what allows people to trust and come to us time and again.
Right. That leads into my next question. Lead generation, sales, marketing, and how we are going to get new clients is such a top question for real estate entrepreneurs, whether they’re agents or investors. It’s, “How are we going to get the leads that we need to have the business that we want?” There’s always somebody out there saying, “This is the way. This is the way.” You’ve built this referral-driven business. What systems keep that referral engine running without you having to chase it?
I’ve been in the business for 35 years, and things evolved in how I worked. When I was younger and raising a family, I was very involved in kid activities. I was surrounding myself with the kids and activities and being in the community.
I also talk about pivoting and adjusting and having to move through your next chapter. When my kids left to go to college and they grew up, my community shifted as well. You have to work wherever you are in your life. You have to reestablish your community and join new communities. You might outgrow one, and then something else becomes more interesting.
Building clientele is in community. We serve people that we know, like, and trust. Where do I start? I’ve been through so many chapters.
I started writing books after my kids went to college. I kind of fell into writing books. My first book, Contained Beauty, was photographs, reflections, and swimming pools. It put me into motion to stop being sad and to do something constructive so I wasn’t so sad that my kids were leaving me. I started meeting people in that environment.
Let’s fast forward to what I’m doing now because I think it’s so relevant, and not everyone is going to write a book and get involved in that.
In the last two years, I joined a BNI group, a business networking group. Had I known when I was 25 and started out in real estate that there were these formal business networking events, not just a cocktail party, not just a happy hour, not just an opening of an event or a chamber meeting, but completely organized business networking events where you are there purposely to refer one another, I would have done it earlier.
BNI is Business Networking International. It’s all about givers gain. I have always been that person. I’ve always referred naturally. People would say, “Why are you doing that? Why do you put so much energy into that if you don’t get anything back?” I said, “It’s just the way I am.” I couldn’t explain it. It’s just how I’ve always been.
I’ve always had that BNI mentality that givers gain. You give and you receive, not knowing that it was a real concept. It was just my nature. When I joined BNI two and a half years ago, I thought, “I’ve met my people. All these people do exactly what I do.” Of course, I’m always number one every month because I do what is asked of us to refer one another and do educational learning.
From my BNI local chapter, you can also connect with people around the globe. Then you can start to refer, and they can refer you anywhere in the world. It’s incredible with technology, Zoom, and all of that.
The other one I joined about six months ago is the BNI international group, just real estate agents. This is where the golden nugget comes in. First, join a BNI group or any networking group because they’re amazing. We’re all like-minded people, and we all want to give and help one another.
With the BNI Real Estate Group, our goal is to do one-on-ones, get to know one another, and refer one another.
When you work with a BNI person, for the most part, I haven’t met one who isn’t like me, passionate and wanting to help. I recently referred an agent in Scottsdale for a buyer for four to six million, but I like him and trust him and know he’ll do a great job. As soon as he showed those people, he called me that day. He wasn’t even home, and he called me and said, “Thank you so much for the referral. They’re great. We had a great connection.”
That made me feel good because if I’m going to refer someone, I want to make sure they’re going to take care of them the way I would take care of my client. In a nutshell, professional networking is not like anything else because it’s not walking into a cocktail room not knowing anyone. It’s walking into a room full of people who are like you and want to help.
Great points. I love that. We’ve talked about how you get that business in. Now let’s talk about your operations and how you serve that business. At your level of production, what does your support structure look like for that real estate team? And how do you know when it’s time to stop doing things yourself?
That’s hard when you’re speaking to a control freak. For a long time, I did everything, and I didn’t have a calendar. I had it all in my head. Now I’m getting better. I’ve been working on a calendar, and I hired a virtual assistant in the last six months.
Now I have a podcast, I have a book, I’m getting all kinds of inquiries now, and I’m full-time in real estate. I’ve hired a VA. I tried to hire one that wasn’t local, and I know the price is so much better, but for me, I have to be able to see someone. Even though I don’t see her all the time, she is in my BNI group, so I see her every Wednesday. There’s no communication gap. I can rely on her.
I’m not saying you can’t rely on a virtual assistant who is out of the area. I think it just has to be the right connection. She is on it, and we have the same time zone. I don’t know how VAs would work on a different time zone. It’s been really great. She’s very responsive. She understands my abbreviated questions or thoughts that come out of my mouth. She can figure out what I’m saying. She kind of understands in advance. She doesn’t forget things, so that’s super important. I’ll say something, and she’ll bring it back up. Maybe I forgot, but she brings it back up. It’s really important to have that.
Of course, having a transaction coordinator for your deals is super important, so we’ve had that forever. In the beginning, you’re doing most of your paperwork to learn. I think right now the problem is newer agents aren’t learning because there are these TCs in place that are doing almost everything for them. That’s kind of a blessing and a curse.
Having a transaction coordinator and sending all my papers means I can be out meeting people. Today I’m going to go meet the manager of a senior center because I also serve seniors. I’m a senior real estate specialist.
With my structure, my husband, my son, and myself, I’m kind of out there. I’m getting the house ready for market, doing the design, meeting the contractors, et cetera. My son and my husband like to be at a desk. I like to be all over the place meeting people. I do a lot of one-on-ones and building relationships and referrals, but they’re super great on the follow-up and the contracts and the disclosures. Not that they don’t do everything, but that’s how it lands with us. I’ll do the marketing, and I’m trying to get my son now to move over to do more of the websites and that sort of thing.
Recently I’ve started working with a graphic designer. I do a lot on Canva. I love Canva. We can talk about tools in a minute, but did I answer your question?
Yes. You see the value of bringing other people in and having them bring their skills that complement your skills. That’s really nice. I know client experience is also important in the kind of clients that you serve and the price point that you serve. How do you protect that client experience while still leveraging your team and having other people start to handle some of that work?
When I bring in a client, when I’m starting to work with a client, I am always right there to speak with them. We’ve never really had a buyer’s agent. I don’t understand how people do that because if it’s me and my husband, and now my son will do it too depending on if there’s a schedule conflict, I try to be that first point of contact. If it’s my client and I’ve brought them in, I like to be that first point of contact.
Let’s say there’s a disclosure we’re going to send out for a buyer. I’ll include the team on that, and I’ll introduce them to Adam or Chase, but they’re family. It’s different than someone else. It would be really hard for me. I know I should maybe have buyer’s agents, but it’s really hard for me to let go because I am such a mother, and I want to take care of those people.
I will introduce them to my team, and sometimes they’ll show a property if I’m unable to, but it’s gentle. I’m always there. I always say, “Text me, call me, email me, but text me for a quicker answer. I want to answer all your questions.”
I think one of the biggest things and one of the most important things is that it’s a really stressful time for a buyer or seller, so they need answers right away. People know no matter what time it is, I’m going to respond. If I see that coming through, I will respond. I don’t want them to wait at all.
When I’m working on a deal with an agent on the other side, and if they’re not responsive, it’s very frustrating. Communication and collaboration are so important. I have something called the Five C’s of Real Estate. Communication and collaboration are so important.
I’m working with a client right now, and she said, “I didn’t want to call you. I don’t want to bother you. I know you probably didn’t know the answer yet.” I said, “No, as soon as I got the answer, I called you. I didn’t want you to wait, but you can always call me. Don’t worry about that.”
You have to say that over and over again because sometimes clients feel like they’re bothering you. But if you don’t keep them in the loop, they’ll get frustrated, and you don’t want them to do that. When it is time to talk about something important, you want to make sure that you’ve kept that communication open so they’re not frustrated by the time you call them with perhaps bad news. You want to keep that relationship going.
Great. Now let’s switch and talk about your book and what it contains. My understanding is that this Mindset in Motion Method is a five-step framework for aligning your vision with execution. Can you walk us through that framework?
Absolutely. The framework is called the Mindset in Motion Method Framework. It can be used for anything from excelling in real estate, conquering a personal goal, a business goal, overcoming an addiction, going through divorce, going through the empty nest, going through any transition, as well as elevating yourself and pursuing a goal.
The five steps are this. The first one is you have to establish a goal, and you have to be crystal clear around that goal. You can have a lot of goals, but start with one and be really crystal clear around that goal.
Number two is you have to believe. I don’t care how you’re going to get there. Just believe it will happen.
Number three is internalize. You have to feel that goal. What’s it going to be like when you achieve that goal? See yourself in that goal. This is where you can start doing a collage, Pinterest, journaling, but start to really internalize that. What is that goal going to be? What is it going to be like to achieve X or get through X?
The next one is share. It used to be just share, then I changed it to share with supportive people. We can’t share everything with everyone because people might think you’re crazy, or they’ll think you can’t do that. You don’t want negative naysayers in your mind. You need to only share with supportive people.
When I decided a month before the LA Marathon that I was going to run the marathon, and I had not trained for it, do you think I would have shared that with everyone? No, because people would be like, “You’re going to be 60. You don’t train. You barely eat right. How are you going to do that?” I did not want that. I was trying to prove to myself that you can run a marathon on mindset alone.
I did read stuff. I listened to books, audio, YouTube on the military, not on running. I was thinking, how does the military, how do these soldiers become superhuman? How do these Navy SEALs do what they do? That’s how I trained myself, not physically. I had to share it with supportive people.
The last step is to activate. This is the tough part. This is the place where people ask, “Do I really want that goal? Do I really want to do that?” Or people going through a divorce sometimes get stuck. Activation is the hardest step, but this is where you have to bring in all your supportive people and mentors and accountability partners and coaches, family, whoever is going to support you and be your cheerleader.
I talk about in the book, too, that you can reach out to people you do not even know. No one knows what you need until you ask. I’ve done that a number of times, and I have a good friend in Bob Burg because I reached out to him.
I love that. Of course, I’m also wondering, how did the marathon go?
I crossed the finish line, and I burst out into tears. I do not know why because it wasn’t a goal like having a baby or anything like that. For me, it was, “I just want to prove you could do it.” But when I crossed that finish line, I burst out into tears. What did I just do? It was pretty amazing. It was kind of crazy.
I have to share something with you right now because I believe, and this is in the book, that when there’s something in my mind or something that I’m considering doing, oftentimes if I’m going to do it, it shows up. This just happened this morning, and I’m going to unveil it here. I do not know what will happen, but it will be documented if it does.
Because of my book launching number one bestseller on Amazon, I’ve been getting a lot of emails and a lot of opportunities, which has been incredible. But I got an email today, and I have about 600 emails I’m trying to get through. This one was from the Great Adventure Race, inviting me to seven continents, seven marathons in one week and seven days. Private flights, first class, et cetera.
First of all, I’ve only run a marathon one time. I did not train for that marathon. So I responded, “That sounds amazing. Thank you for the offer. However, I would need a sponsor.” I didn’t say no. I didn’t say I don’t want to do it. I said I would need a sponsor. That’s where I left it. We’ll see. Of course, I did a deep dive on their website to even know what this was.
I don’t know until I know, and it’s a possibility. One of my quotes I always say is, “Look for the extraordinary in the ordinary. That’s where the magic lies.” We’ll see.
It’s great what opportunities present when you’re open to them.
Yes, and what happens is a lot of times people aren’t on the lookout. They might be looking at their phone. They’re not paying attention. Every day when I wake up, I’m thinking, “What is that cool thing that’s going to happen?” Not one thing. It could be big or little, but I’m always on the lookout for the magic.
That leads right into the next question I had. I love the framework. That is something for people to use to level up their mindset. What challenges do you see? What are the mindset traps that you see a lot of people in the real estate space fall into before they figure out that Mindset in Motion Method and start using it?
The biggest one is, because I just interviewed a coach and I asked her the question that annoys me the most. I said, “What do you say when people say to you, ‘I don’t have enough time’?” That is my biggest pet peeve.
We cannot control time. We can manage our time. If it’s a priority, you will implement and take action. Everyone’s busy. What you’re saying to me is one of two things. One is, if you don’t have enough time, you don’t care, and it’s not important to you. It’s not a priority, so let’s just stop there. I don’t want to coach anyone who says they’re too busy.
The other one that often frustrates me is “I don’t know.” Well, you can find out. As a coach and a mentor and an owner of a company, if someone has a question, I don’t care if you’re a new agent or a seasoned agent. If you have a question, you can call on me. You can call on our other partner. You can call on my husband Adam, who’s the broker. We will give you that answer. We will tell you where to find that answer.
Whatever the question is, you can probably ChatGPT it, Google it, ask someone, ask a professional. There are coaches all over the internet sitting there waiting to help you. You can ask them a question. You’re not going to have to hire them, but ask the question. Get the answer. It’s not hard.
People ask me questions all the time or ask me for a referral or recommendation. They say, “You don’t know me, but I know you offer advice a lot and you’re really connected.” It’s just part of my DNA. I can’t help it. Not everyone is going to be that way.
But if you’re speaking to a client and a client is asking you something, say, “I’ll get right back to you.” Get the answer. You don’t have to know everything, but you can find out. You can ask someone who can help you and point you in the right direction. “I don’t know” means “I don’t care.”
Very true. I feel like in this day and age, it is easy. We have information overload. Saying, “I don’t know,” is silly because we can find information easier than ever. It’s amazing. It’s so cool. My kids will ask me questions, and I’m like, “Well, that’s as simple as a Google search or AI.” Then I get to learn alongside them too, so that’s fun.
Absolutely.
What I would love, Debbie, is if you can walk us through a time when a deal or client or something did not go the way you planned and how you were able to keep that mindset and not fall into scarcity or worst-case scenario. What did that look like for you?
Let’s see, what would be an interesting story? I’m going to go back to communication. It really just takes communication. Whatever the story is, it’s about communication because miscommunication causes friction.
Years ago, I came up with this: we’re colleagues, not competitors. I had to explain that to my son and his friend once. He said, “Are you not going to be friends with my mother now because you’re at a different company?” I said, “No, we’re collaborators. One of us has a listing. One of us has a buyer. We need to work together.”
We’re collaborators, and we collaborate as referral agents with agents all over the world. We’re our biggest advocates.
I was working on a deal, and you have to think, what is the reason? Where’s the disconnect? I was the listing agent working with the buyer’s agent. The buyer was a woman. It appeared to be just a woman without anyone else part of that transaction. The contingency was delayed. The communication was not there. I kept calling the agent.
“Can you give me a call? Can you give me a call?”
She’d respond with a text, but there was nothing in there. I said, “No, can you please give me a call? Because I think if we have a conversation, we’re going to be able to get to the other side of this.”
I finally had to call her broker because the broker was a friend of mine. I said, “I don’t mean to tell on her. I just know if she picks up that phone, we are going to get through this.” The agent called me right back. I said, “Hey, I just want to know what’s going on. What’s the hesitation? Why this? Why that?”
She said, “My buyer’s father is very worried about her because of X.” Now we have someone else in the deal.
I asked, “Where is the father from?” She said, “Los Angeles.”
I said, “In the East Bay, different markets are very different. All markets have their own way of doing business. We’re in the Oakland, Piedmont area in the East Bay. He has a mindset of how they do business in LA.” Since I work in LA, I know the mindset of the agents, the sellers, and the buyers. It’s very different.
Once she said the father was in LA, I knew how to get through to the other side. I knew how to communicate with my client about what was going on in his mind. We were able to get through the deal seamlessly to a close, but it was only because she finally picked up the phone so we could have an understanding.
That’s the problem. Texting is great. Email is fine, but once in a while you’ve got to pick up that phone. Especially when you’re working with a buyer and it’s all new to them, you’ve got to explain things to them through the mouth, not just through text. You can say, “Yes, meet you at five o’clock,” or “Yes, this is this.” But when you have to go a little deeper, pick up the phone and make the call.
It’s so funny that you chose that example because when I was an active real estate agent, that exact issue would pop up. Not all the time, but when it does, your job as an agent is to facilitate the deal. But so many agents were like, “I just want to text.”
Exactly. I’m working on one right now. Thank God it’s not been a difficult deal, but to get them to pick up the phone is hard. I don’t understand why they don’t. Why are they hiding? I don’t know if it’s an age thing. I don’t know what it is. It’s bad.
I’m with you. I think it comes down to that “I don’t have enough time” issue we also talked about. People feel that phone calls take up time.
Debbie, as we wrap up here, what does the next chapter of your business look like? And what advice would you give to somebody who is starting where you were on day one, 35 years ago, and wants to be where you are in 35 years?
I had a 16-year-old come into my office. She was referred by a friend. She came into the office, and she was darling. I thought, “Wow, she’s 16.” We were having a conversation, and then all of a sudden she said, “Can I ask my questions?” I thought we were just there for a casual meeting and that she was going to ask me a few questions. She had two pages.
I said, “Sure, shoot.” She started asking, and I was answering, and we went down the list. Then I said, “You know what? I think you’re ready for my real estate book, The Art of Real Estate.” It’s very dense, but if you’re truly interested in real estate, then that’s where you go. It’s for buyers, sellers, anyone looking to buy or sell. It’s for agents, anyone, but it’s pretty dense. You have to be into it to want to read it. I gave it to her because she was so motivated.
One of the things that I’ve learned in my 35 years is be persistent. Don’t give up. People give up too soon.
We have one of our agents. He’s a flight attendant and an agent, but he works really hard. He doesn’t complain about time. He continued his day job or night job or overnight job, but he always shows up. When he first started, he was doing Saturday and Sunday open houses even though he was flying in at midnight, and he was showing property before the 2 o’clock open house. That is someone I’ve used time and again because he doesn’t complain about time. He’s always happy, and he just does the work.
When someone says they don’t have enough time, look at these people. They’re making the time. Be persistent. Don’t give up. Have a second job. Do something on the side while you’re starting. It can’t be something that takes too much brain power. It has to be something where you can make money because you have to be available to your clients.
One of the biggest things I can say is join a professional networking group. I feel like in 35 years, I’m so behind just starting six months ago in this BNI Real Estate Group. I’m like, “You guys have been at it for 18 years, and I’ve already seen results from it.” I’m so far behind the ball.
What my future looks like is continuing to serve clients, continuing to grow my referral business. I’ve done it forever, but I want to continue to grow. Through podcasting, and I have my own podcast, Mastering the Art of Success, I’d love to serve and refer more agents. I love referring like-minded agents to help my clients.
I want to speak. I’m going to be speaking at Luxury Real Estate, LRE, in Denver on September 28th. Most real estate agents know Luxury Real Estate International, so I’ll be the keynote speaker there. The press release is actually going out today.
Exciting.
Book me for a keynote presentation. I can do it on Zoom or in person. I don’t mind traveling. I’m going to be speaking at the next two Women’s Council of Realtors chapters, one on June 4th and one on September 17th. I’m open to inspire and help people elevate their business.
Perfect. That leads us to this. If people would like to connect with you, what’s the best place for them to reach out?
BookDebby.com. It’s D-E-B-B-Y. BookDebby.com. Thank you.
BookDebby.com. Perfect. We’ll have that underneath. Thank you so much, Debbie DiMaggio, for joining us. If you got value from this conversation, please subscribe wherever you’re listening and give us a review. It really helps me out. Join us again next week for another episode.
Thank you.