Rosalee DiScipio – Investing In Yourself

osie d podcast image

Show Notes

Welcome to the agents who crush it in real estate podcast where you’ll hear the good, the bad and the ugly of how real estate agents overcame challenges and grew their business. Check out the Episode Notes at Here’s your host, Anthony Lamacchia.

Lindsay Favazza: I am here with one of my favorite people and a very special guest today, Rosalee Discipio. Welcome, Rosie, to the Agents Who Crush In Real Estate Podcast. 

Rosalee Discipio: Thank you. Thank you for having me. 

Lindsay: Absolutely. When we think about agents who crush it in real estate, I would have to have you on here because you have always been so consistent. One thing that I noticed when going through prepping for today to talk to you, I wanted to dive a little bit more into your sales and things that I’ve seen from you at Lamacchia. One of the things that I’ve noticed is that you, over the years, it’s more and more of your own business. Do you feel like that is a change that’s been happening for you for awhile? 

Rosalee: Yes, I actually do. Most of my closings are my own business, few referrals, and I do actually get a lot of in-company referrals from other agents of people moving. I love those because having my colleagues trust me is one of my most favorite things. They know that they’re going to send me a referral and then I’m going to take care of their people and then everything else is pretty much mine. 

Lindsay: Take us back. Take us back to the beginning. Tell me about where you started in real estate, when you got into real estate, and give me the ugly truth about your– 

Rosalee: I was a bartender for about 15 years and I also worked in construction management. During my construction management job, I was pregnant with my second daughter. I came back from maternity leave and the entire market of everything was bad 2009, 2010. I got laid off and I didn’t know what to do with my life because that was my plan. I was going to be in construction management and bartend on the side. 

I continued bartending and got my real estate license. My husband got a job where we could have health insurance because I didn’t have it anymore and I hated it. Ugly truth, I hated real estate. I didn’t want to do it. “This is not for me. I want to bartend. I want to be in construction.” That’s what I wanted to do. I really struggled with starting something I didn’t think I liked. 

My first-year licensed, I did four sales and I think it was really mentality. I wasn’t in it. I was good at it. I just didn’t have my head in the game. We had had our own real estate company that closed. I was now in– 

Lindsay: What was the biggest thing you hated about it? 

Rosalee: I think that I didn’t like working with the agents I was working with. We closed our own company and we had seven agents under us. I did all the paperwork for the company and I went to work for a place and I won’t say the name of the company, but I didn’t enjoy– There was no comradery. There was no help. There was no energy. It was all, “I will suck whatever I can out of you if I can.” 

That really killed me in a job. I have always worked in places– bars are fun and we work together, and I’ve always worked in that. Then you get into this really cutthroat business and you’re taken aback from it and I’m a positive person. I like to project positive energy and that’s just not what I was met with. I spent 10 months at that company and then answered a LinkedIn ad to come to Lamacchia. 

Lindsay: Lovely. 

Rosalee: The next year, I think I did eight or nine sales with Lamacchia. Following year after that, I did 10 or 11 somewhere in there. A lot of that was Lamacchia referrals, so I was lucky to have them. 

Lindsay: Did you start to love real estate after that? 

Rosalee: I started to love real estate when I got to Lamacchia and I was in an environment where people wanted to see me succeed, and that really changed my mindset about the business. I knew I was good at it. I’m really good with people and understanding what they need and investing in them. I needed that on my side, wherever I was going to be. I needed that and I needed to work with other agents that wanted to see success rather than the opposite. 

There’s other companies out there across the country that do the same thing because I speak to agents all over whenever I can and ask them about their company. That’s really the key to successful.

Lindsay: I think there’s a lot of brokerages out there that don’t pay attention to that culture that their office has. That really is what can hurt a lot of them. 

Rosalee: Especially with newer agents. It’s being fed to wolves. When you come in and you’re fresh, you’re new, and you’re excited, and this is your career, or this is your career because it has to be not by choice, whatever it is, you’re in this job. If you don’t have people around you that want to see you grow and succeed and you need that type of thing, you’re not going to do it. 

Lindsay: It’s a sales role. Most sales companies put so much time and effort into making sure that people are happy and having fun and all of that, but then, yes, brokerages just don’t do that. Then you’re left on your own a little bit. 

Rosalee: Nobody likes an angry agent. 

Lindsay: No, absolutely not. 

Rosalee: It’s bad for business. It was really beneficial for me for that. Then progressively, my sales got better every year; 14, 14. 

Lindsay: Tell me about your stats, year over year kind of thing as far back as you can remember. 

Rosalee: I was stuck at like 14, 15 sales for like three years. I had had a third baby and I was not really– 15 is still a really good year. It’s still really financially a good year. I just was stuck a little bit and I had taken a step back and switched a company and made a little bit of a mistake there. When I came back to Lamacchia in 2019, I just took off and I did 23 my first year back, 25 my second year back, and now I’m on a really good track this year. Very excited. 

Lindsay: Yes, I know. You had told me before we started that you have a lot under agreement right now so you- 

Rosalee: There’s nine under agreement, hopefully more by the end of the weekend, but nine for now under agreement, 13 sold already this year. It’s been a tough year. 

Lindsay: When we look back at last year where you grew your business still, and we have this asterisk of pandemic looming over it, then imagine what you would have done if that hadn’t happened. 

Rosalee: It was a little wild last year. I had a lot of sellers that I had shelved their sale and a lot of buyers that couldn’t buy. We just didn’t have places for them to go and they ended up either living with family or renting. That, to me, was personally sad. It was the right thing for everyone to do and you always think about the client first. For me, it was a little, business-wise, sad. I had goals and I hit a different goal. 

I did hit my financial goal last year, actually crushed the heck out of that one. 

Lindsay: You had some big dollar amounts. 

Rosalee: I had some big three luxury sales last year, which were wonderful and they take a lot more time and effort, but they’re worth it. It was a tough year for everyone and to the agents that did crush their goals, that’s amazing. This year, I’m head down ready to go and I’m not trying to manage three kids homeschooling in the middle of it. Everyone’s back to where they need to be, so I have a little more free time to work. 

Lindsay: Perfect. Take me back to when you were beginning in the business again, and what struggles were you facing and how did you overcome them? What were some of the struggles that you ran into in the early days. 

Rosalee: I hate being on the phone. I still hate being on the phone and it’s not– I will talk to any client I currently have, but it is that calling a lead back. I struggled so hard with that for years, level of fear. If you know me personally, I’m not a shy– [inaudible 00:08:23] – 

Lindsay: I remember when you first told me this about yourself a couple of years ago, and I remember sitting there thinking like, “What? That doesn’t even make sense.” You could talk to anybody. 

Rosalee: I can talk to anybody’s face. I hate being on the phone, hate having that cold conversation on the phone where I’m trying to get you to understand that I’m the best for you. I am going to do my job and you lose a level of trust when you’re not in front of somebody’s face. I struggled really, really hard with getting people to hear me on the phone. Whether it was a scripted call or not, it was inorganic to me and I really didn’t do well up until last year. 

Just think about that. I’ve been a licensed agent for 11 years and I couldn’t make a proper phone call to call a client back or a potential client back until last year. 

Lindsay: How did you overcome that? What were some of the things that you did? 

Rosalee: Obviously, I had the best real estate coaches ever here. I hired a life coach to figure out what was wrong with me and spend six months– so weekly, an hour a week with a life coach, to say– realistically, I hired it specifically to figure out why I couldn’t do these things. What was I afraid of? What was going wrong in my head when I was making these calls? It actually was mid pandemic when we had Jon Cheplak and I asked a very pointed question. “What if you know all the right things to do, but you still can’t do it?” He responded to my question, “You have to go back to go forward.” Basically, there’s something in you that is preventing you from doing this. You have to go back to that moment that is saying you’re afraid of this, and it’s going to hurt you or whatever, and fix it so that’s what I did. I hired a life coach, it wasn’t cheap in a pandemic, and I did a lot of heavy work. 

Lindsay: Being an agent isn’t just getting on the phone, making calls, and doing your job, it requires you to dig into your personality a little further. It sounds like you recognized that you needed to do that in order to take that next step and you were willing to make those changes and invest in yourself. 

Rosalee: It wasn’t easy because it’s more than just a business. I didn’t want to hire just a business coach. I have a great real estate coach. I have tons of real estate coaches here, and they’re all wonderful, and I know all the right stuff to do. It was a personal issue that I could not progress through and it wasn’t silly, or anything like that. It was like there’s no amount of, “Just do it, just make that call.” I couldn’t. I just couldn’t, and it was painful. 

Working through with the life coach was really– and it was the best like seven grand I ever spent. It wasn’t cheap, but it really– 

Lindsay: Think about that as an investment. 

Rosalee: It changed my life. It was one closing for me. It was one closing- 

Lindsay: It’s one closing and now you’ve overcome that fear, and you can move on, and you can feel like you can make it to that next level in your business. 

Rosalee: I don’t think that I would have had the luxury sales or the confidence to– even though I knew what I was doing, the confidence to guide through those types of sales if I hadn’t done the life coach. That’s where I’m at so it was the small investment of money into that returned so much more last year and it was a great time to do it because it was a pandemic and I had a little more time to do these calls and stuff and– 

Lindsay: I love it. Well, I’m excited to hear that too, because I know, like I said, you and I talked about this a while back so I’m excited to hear that you feel like you’ve overcome that. 

Rosalee: People are afraid to invest in themselves. You feel guilty, and you feel it’s going to be a waste of time and effort and you should just do what you’re told. I had to get over that too. I really needed to spend some time and money on myself. 

Lindsay: Absolutely. 

Male Speaker: Let’s take a quick break and hear from the number one loan originator, Shant Banosian of Guaranteed Rate as he gives us his monthly mortgage tip. 

Shant Banosian: Hey, realtors. It’s Shant. I just wanted to come at you guys with another quick tip. It’s important to know your numbers, so we have what we call our accountability metrics that our team goes over every single week. It’s a way for us to figure out what’s going well and what’s not going well in our business. 

We have certain metrics, whether it’s how many leads we’re going to drive in, how many appointments we need to have, how many loans we get a lock, or how many loans we need to close on a weekly basis, or how our customer service ratings are coming back, or how fast we’re closing loans, things like that. We’re monitoring every single week and when something goes off track, we identify what the core issue is and why that’s happening. 

Doing that every single week is massively important because that way, you identify the issues immediately and fix them immediately, as opposed to having weeks or months go by so knowing your numbers, knowing your key metrics is super important. 

Male Speaker: Thanks, Shant. Now, let’s get back to the show. 

Lindsay: That’s great. Well, like I said, I’m super excited to hear that about you. What has been your biggest key to success in your career overall? What do you think is the thing that you can say differentiates you from the rest, or what is it that you provide your clients? 

Rosalee: I spend a lot of time– by some standards, maybe too much time, getting to know and learning my clients, not just them but if they have family too. I invest a lot into what they might want or need. You’re never going to get a client that’s going to say, “This is exactly what I want,” because even when they say that, sometimes they buy a completely different house so you really have to lean in, learn, and hear them when they’re talking. I spend a lot of time with that. I’m really, really good at understanding people. 

Lindsay: That’s why at the beginning I said you have more agent business than company business as the years progress and that has a lot to do with it. You make those deep connections with them. 

Rosalee: I make them long-term. I don’t ever just sell a house and leave the people. Sometimes at the end of the transaction, it’s been great the whole thing, and then there’s a hiccup at the end and they’re angry at the end of it or whatever, but I don’t let that go. 

I continue to show up and be present in their situation and then eventually, we get to that point where we’re like, “Remember when this was messy,” or, “You showed up and there was still a tractor in the garage,” whatever it is, you try to continue to work through it. If something goes wrong and you don’t show up after that, you don’t talk to them again, that justifies them being upset so you have to continue to work through it and build those relationships. 

“We were upset about this, but she’s kept showing up, and she was here.” That’s what I do I do drop off Christmas stuff or holiday stuff. 

Lindsay: I was going to say dig in deeper on what do you actually do to keep in touch with them after the sales. 

Rosalee: After Thanksgiving, and before Christmas, I do holiday drops, so wine, chocolate, things for the kids, whatever they have, I do those drop-offs. I didn’t do it this year, pandemic stuff, but I normally drop off flowers for Mother’s Day. I don’t do for dads. I know it sounds bad. I once upon a time was a single mom and dropping off flowers and appreciating the moms is something I always do. 

Lindsay: Sure thing, that’s cool. 

Rosalee: I do mailers, Red Sox, Patriot schedules. Then, if I’m in that town, I’m going to text my client, my best client, “Hey, are you outside? Are you around.” Last year was really hard, but even still, I went to people’s driveways and say hello. I still did that sort of thing. 

Lindsay: Which went a long way because no one was doing that nobody was doing that. 

Rosalee: Nobody was doing it. It was like, “Hi, I’m outside your window. House looks great, whatever.” I’ll text them and be like, “Send me pictures. Did you guys ever do the kitchen?” Little things like that. First off, I don’t have to get on the phone, and secondly, who has time to be on the phone right now if you have like three kids, whatever. I’ll text them, “Did you ever do the floors? What did you guys do with this?” Just little inquiries into their daily life or whatever. 

I had a client that she texted me out of the blue and she said, “Hey, my husband got a promotion. Thanks for helping us find a condo last year, maybe next year, we’re looking for a bigger house.” It was great, so I sent a little celebration package to them and a card and congratulations on the upgrade and just you have to take time, people want to be thought of. It’s such a busy world. 

Lindsay: In this business, they’re working with someone that they need to know, like, and trust- 

Rosalee: And remember. 

Lindsay: -and remember. On a deeper level, they need to actually really like working with you because you’re going to have to work with them on some very difficult things. 

Rosalee: My intention is to be their agent for life and their family’s agent and their friends’ agent when they talk about their sale, even if it wasn’t as smooth as pie. What real estate transaction is smooth? I want them to be like, “Oh, my God, our agent, Rosie, was like so and she was there, she listened, she found us this.” 

Whatever the terms and conditions are, I want them to know that when they tell somebody about me, that person is going to get the best treatment and they know that because the more they refer me. I’m so and so’s family agent, like that’s my favorite thing. 

Lindsay: What are some of the other things that you do to generate leads or generate more business for yourself? 

Rosalee: I don’t buy leads. I don’t cold call. I just don’t. I talk to my sphere. I make those calls. I love the By Referral course that we do where it’s just twice a year you’re writing note cards every week to people. You’re making phone calls to just check-in. You’re sending texts or messages like, “Hey, how’s it going?” It’s just a reminder twice a year to do those types of things on top of the other stuff that I do. Other than that, I hate to say it like this, but I don’t ask for business. 

I just am myself. People know I’m in real estate. I have a very wonderful Facebook page that I share stuff from. That social media angle has always been wonderful for me. It’s a little passive, but here’s some information if you want it and I want to make sure that everyone knows I’m in real estate without actually being like, “Hi, can I have your house? Can I sell your house?” I don’t want to do any of that. It’s not authentic for me and it works for some people, but it doesn’t work for me. 

Lindsay: Your focus is on the relationship building and the long-term game instead of the quick sale and the numbers game. I think that that’s important for people to understand, that they don’t have to be that uncomfortable salesperson. They can just be a caring human being and still grow their business so I think that’s a great– 

Rosalee: I think my business has grown a little slower because I’m so focused on it, but my repeat business and my referral business is so strong that I don’t think I would trade that for a quick sale. I could sell 40 houses with buying leads and this and that, but I just like that personal touch so much better. It’s more who I am. 

Lindsay: Any advice for agents out there that maybe are at that 15 mark, at that weird place where you feel like you’re doing well but you’re not quite hitting where you want to go? What advice do you have to someone that is maybe sitting around that 15 mark that wants to make it to that next level? 

Rosalee: Get a coach. Get a coach, whether it’s a life coach, or a real estate coach, or somebody that’s going to check in with your mental state on a weekly basis. Go get a therapist, I don’t know. Somebody that’s going to check in on why you’re stuck because if you’re stuck at the same number of sales for three years in a row, there is something there that is holding you back. There’s no reason not to progress in real estate unless you’re trying to step out of the business. 

If you’re stuck at four sales, what’s your focus? My focus was primarily on my family at that time, which was wonderful to be able to be with my kids and do everything I needed to do, but I knew I was stuck. What was it? It was me. I was the problem. If you’re stuck at the same amount every year, something’s going on with you. You need to invest either in yourself, which a real estate coach, a life coach, a business coach, all of those things will take care of whatever’s going on within you because they’ll find the problem. 

Lindsay: They’ll find stuff that you’re not paying attention to. 

Rosalee: Yes. If everything is generally okay, then maybe you want to step up another– Are you doing the right advertising, the right marketing? Is your social presence there? Are you spending money on direct mailing? Are you writing handwritten cards? Those things. You need to find what is keeping you from moving forward. 

Lindsay: It’s identifying the problem and then going after it. 

Rosalee: Actually going after it. That’s the other thing because you can know– I knew my problem was not being able to make calls. What do I do to get out of that? I didn’t know for a while. I didn’t know what to do. 

Lindsay: The answer wouldn’t necessarily, in my mind, clearly be, “Get a life coach,” so you obviously did some digging and had to figure out what that thing would be. 

Rosalee: Yes, I did. I did. I actually had a therapist for most of my life, and he basically said, “I don’t think I can help you anymore. You’re good here. You need some next-level stuff.” I didn’t know what that was for two years. It was two years before I figured out, “Oh, I need some life help.” It was great. It changed my whole perspective. 

Lindsay: That’s awesome. It probably changed things outside of work too. 

Rosalee: It did. It was surprising how well it worked, how quickly it worked within two months. It was like, “Oh, my goodness, I’ve just been–” A lot of my things where I would say a lot, “I feel so overwhelmed. I have three kids, I have this job, and I’m selling 20 houses a year, I have a house to maintain, and I have all these things,” and then we have a pandemic and I was like, “Oh, God. Now, everybody is home all the time, and I still have to work. I’m blessed to be able to work.” 

There were a lot of people that couldn’t. “Why do I still feel so overwhelmed and upside down all the time?” Digging through that was really a lightbulb moment for me, and it changed my entire mentality in how I approach every day. 

Lindsay: Well, I am excited to see what the future holds for you now that you’ve uncovered this about yourself and can move forward. Keep us posted, obviously, and maybe we’ll have you back to update and put some of your– 

Rosalee: Well, when I make president’s club 

Lindsay: Absolutely. It’s going to happen. This is your year. Thank you so much, Rosie. I really appreciate you doing this for us today. Stay tuned for our next episode of the Agents Who Crush It In Real Estate. 

Rosalee: Thank you, Lindsay. 

Thanks for joining us on the Agents Who Crush It In Real Estate podcast. We hope you’ve learned some valuable takeaways. Be sure to take action and grow your business. You can check out the Episode Notes and more content from the show at And if you’d like this episode, and you’d like to hear more stories, please share with others, post on social media or leave a rating or review. To catch all the latest from Anthony you can follow him on Instagram at Crush It In Real Estate on Facebook and YouTube. Thanks again and we’ll see you next time.