Stay Consistent, Stay Closing: Jessica Rizzo’s Success Strategies

In this episode of Agents Who Crush It In Real Estate, we sit down with Jessica Rizzo, a top-producing agent in the Berkshires. Her journey from juggling multiple jobs to becoming a two-time Best REALTOR® of the Berkshires winner is nothing short of inspiring.

What You’ll Learn:

  • How she transitioned from waitressing, bartending, and dental office management to real estate
  • The moment she knew she wanted to become an agent after buying her first home as a single mom
  • The importance of building a strong database and CRM, and what she’d tell her younger self
  • How she sold 50 homes in 2024 and built a majority referral-based business
  • Why client appreciation events and community involvement play a huge role in her success
  • Her approach to listings, communication, and online presence that keeps her clients coming back

Jessica also shares her craziest real estate story, the importance of confidence and consistency, and how her passion for helping people makes this career so rewarding. Whether you’re a new agent or a seasoned pro, this episode is packed with valuable insights and motivation. Listen now to hear Jessica’s incredible journey and expert advice!

Follow Jessica on Socials 👇

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 CrushItinRE.com/podcast. Here’s your host, Lindsay Favazza.

Transcript:

Jessica Rizzo: Confidence and consistency, whatever that looks like. Sometimes I’m going into a listing appointment, and I sit in the car, and I have a little pep talk with myself before I go in. If you’re going to sell yourself, if you’re going to sell something else, you have to be confident.

Lindsay Pavazza: Welcome back to the Agents Who Crush It in Real Estate podcast. I’m your host, Lindsay Pavazza. Before I tell you about our guest today, I want to ask for a favor. If you love our show, and it brings you insights and value week after week, please leave us a review, leave a comment, share the podcast. FYI, if you listen on Spotify, you can now also watch at the same time. We have the video interview embedded right there in the podcast. Give it some love so we can share the stories of these amazing realtors that we bring you week after week with more amazing real estate professionals in the future. Thank you very much.

Today, I have an absolute powerhouse joining me from Lamacchia Realty’s Berkshires office. She’s an absolute force in the industry, a top producer who closed over 50 homes in 2024 alone, earning her spot in Lamacchia Realty’s President’s Club Elite. Not only that, but she was also voted Best Realtor in the Berkshires in 2024. I believe it’s not the first time she’s gotten that award.

Jessica Rizzo has been making waves in real estate since 2014. She’s built her success on deep community connections, a background in exceptional customer service, and a genuine passion for helping buyers and sellers navigate their journey. She especially loves working with first-time homebuyers, finding joy in their excitement as they achieve the dream of homeownership. Beyond real estate, Jessica is deeply involved in her community. She serves on the Berkshire County Community Service Board and volunteers annually with Habitat for Humanity, proving that her commitment to helping people extends well beyond the closing table.

In this episode, we’re diving into how Jessica has built her thriving business and the lessons she’s learned along the way. Without further ado, welcome to the podcast today.

Jessica: Oh, thank you for having me.

Lindsay: I’m so excited to have you. We’ve known each other now for, I don’t know, six months or so. You always have this most amazing smile on your face. You’re always so happy and so– you’re a ray of sunshine in the room every single time I see you.

Jessica: Thank you.

Lindsay: I’m so excited because not only are you a ray of sunshine, but you’re also a badass.

[laughter]

Lindsay: You make it happen, girl. I want to hear the entire thing and I want our audience to hear from you as well. I’m super excited to have you here today. Take us back. 2014, what were you doing at the time, and what got you into the business?

Jessica: At the time, I was at home with my youngest, and just waitressing, and bartending part-time, and being a stay-at-home mom. Real estate was something I always had interest in, and I had the time in my life to follow that dream, and go ahead and take the course, and take the test, and give it a shot.

Lindsay: The rest is history. Had you, at that point, already bought a house on your own or is that something you did later or–

Jessica: I did. I bought my first house. I was a single mom with two kids working and working two jobs to achieve that dream. I knew I didn’t want to raise my children in an apartment, and I wanted to give them a home. I made it happen. It wasn’t easy or challenging, but, I achieved that dream. I had went through that process once prior to getting into real estate. That also just made me realize like, “Wow, this is something I could see myself doing.”

Lindsay: I can see now why being a first time home buyer is probably near and dear to your heart because you probably remember how you felt about that.

Jessica: Definitely. Yes.

Lindsay: Take us back to your first days in real estate. You get your license. Now what?

Jessica: When I took the course, when I was finishing up, I was chatting with another girl in my class and, “Who are you going to go talk to?” We’re chatting. We had a list. I started with that list and making some phone calls and sat with a few people. At the time, Berkshire Dream Home, where I started, wasn’t even established fully. It was just getting started. I called another agent. He said, “I’m not set up. I don’t have a training program. I’m not ready. Why don’t you call Andy Perenick?” I said, “Okay.” I called Andy Perenick, and he gave me the same spiel but said, “I’m not quite ready and set up because I’m just opening my company, but let’s have coffee.” The rest was history.

Lindsay: You can’t not fall in love with Andy– he’s just the best– and want to join him. That was awesome. You did that 2014 or soon after that, after you got your license?

Jessica: Yes, right after I got my license.

Lindsay: You’re a bartender, waitress, doing that whole thing, which I feel like I’ve talked to so many people on these episodes that are absolutely crushing it in real estate but have that background. Do you think that helped you a little bit to be so good with working with people and to– knowing so many people, do you think that had anything to do in those first days and in years of you getting off the ground?

Jessica: For sure. I think my background, with that career and my previous career as a dental assistant and office manager, the customer service, always dealing with people in front of you on the phone, and that definitely helped just because it’s the same scenario. You’re dealing with people, who– sometimes it’s super happy. Sometimes it’s stressful. Sometimes people aren’t the kindest in how you react. Just having that customer service background has definitely helped. How long after getting your license, were you able to break away from doing the other job? I know there’s a lot of people who are probably listening right now that maybe they’re not, bartending, but they’ve got some other job and they really want to make real estate their full-time gig. What was the time like for you there? What was the timeframe, and how did that decision go for you?

Jessica: It was scary, but I had gradually cut back. I was just doing three nights a week, and then I went down to two, and then I went down to one. I knew it had to happen and I knew I had to let it go, but it was just a matter of when. One time I’m like, “Sorry, I can’t write this offer right now because I have to go waitress.” That was the last straw. I’m like, “I can’t do this anymore.”

I had done both for probably about five to six years doing both but cutting back over the time. I wasn’t there a lot. It definitely was scary. Now that I look back, I’m glad I made that decision I did to just let it go and just focus on this as a full-time job. A lot of times people, when they start, they need to have another income source. Stick with it and over time, you can, hopefully, build it up to let that other job go and just focus mainly on real estate.

Lindsay: It sounds like you had that moment. I think that that’s a good message for people. It’s like if you don’t think you’re ready, then maybe you’re not. Keep trying to bridge the gap until you know that moment’s going to come where you’re like, “Okay, it’s time to jump. It’s time.”

Jessica: That was the last straw.

Lindsay: You’re like, “I can’t do this anymore.” You’re a single mom. It’s hard because–

Jessica: Was.

Lindsay: Yes, you were [crosstalk]

Jessica: Yes, was. At the time when I bought my first house, I was a single mom.

Lindsay: When you got into real estate still?

Jessica: No. I’m married now with three children and was when I got into real estate, which also helped because we had another income.

Lindsay: I was going to say that must’ve been even more challenging. Now knowing this, that definitely helps. At the same time, there’s plenty of people who have done it that didn’t have that too, because they made that transition work between the gaps. That makes a lot of sense. Now you’re getting in. You’ve got Andy. He’s helping you out and giving you the lay of the land and definitely very mindful of training, which I think is important. Tell me how those early years were for you and the career. Were you totally freaked out? Were you excited? What was the trajectory for you?

Jessica: I was always excited and eager to learn and eager to do it the right way. If you talk to Andy, in my earlier years, he’d be like, “There’s no one that asks more questions than you, Jessica.”

[laughter]

Jessica: I always wanted to do it the right way. I’m always– like to be five steps ahead. If there was a scenario or something that would be coming up, I would like to go over that with him. When I was actually in the moment, if it was something I knew I could pre-plan for, just having that discussion with him of, “Okay, so what should I do? How should I do it?” Starting with him being the mentor that he is, he definitely shaped my success, for sure.

Lindsay: I love that. All right. Tell us what you would say to Jessica Rizzo then that you could now. What would you say to her? Obviously, she was still excited, she was still green, she was still all of these things, but now that you’ve had such an amazing career over the last, what, 11 years, what would you tell that version of yourself now if you could?

Jessica: This is an easy one because I have a good friend of mine who just got into real estate. She was just on her license in New York. She came over for lunch last week and she’s like, “Okay, so what should I know? What should I do?” I said–

Lindsay: She’s asking you questions?

Jessica: Yes.

Lindsay: The questioner has now become the asked?

Jessica: Yes. I said, “First of all, number one is to have a database, have a CRM.” I’ve always had one, but did not utilize it to its full extent in the beginning of my career. Now I’m religious with it, and it’s my Bible. Everything has to be in there. Starting from the beginning of your career and just to have that database is definitely– it’s gold. That’s your business.

Lindsay: When you finally started to keep track of those things on CRM, what kind of things would you keep track of? Was it only based around deals? Was it that you would keep track of things on the leads as far as conversations go? How do you use your CRM to the fullest advantage?

Jessica: In the beginning, I was using it as, basically, a placeholder for my people. Then I started diving into it more, just making sure you have all of their contact info in there. If there’s anything to highlight about them, birthdates, if they have pets or anything, because you can only remember so much. Then, of course, diving into the whole number aspect of it. In the beginning I did not. I was just putting my people in there, and I was putting no numbers. Then, as you grow your business and it’s fun to watch it, though, throughout the year when you’re using it to its full capacity.

Lindsay: When you have 50 homes that you close in a year, you better be keeping notes on people. I don’t care-

Jessica: For sure.

Lindsay: -how much of a memory you have, that’s still going to be very, very difficult. All right. Now, we’re present day. Now we’ve made it through the timeline, right?

Jessica: Yes.

Lindsay: 50 homes is incredibly impressive. How do you balance that? That also is a lot of time. There’s people who are listening right now that closed 20 homes, and they’re like, “How the heck does she close 30 more? That’s daunting to some people. What advice would you give to them about that?

Jessica: Having systems in place is huge. Sometimes when I’m on an appointment, I’ll say to sellers, “Sometimes there’s an agent out there, they’re doing it all on their own. They’re meeting with you. They’re doing their own photos, their own floor plans. They do not have an assistant. Having the systems in place and– there’s things that I’m great at. I’m not great at taking photos of homes. Just to have the systems in place and to have a person and– having an assistant is huge– to help with the day-to-day things that need to get done, so I can focus my time on meeting with buyers and sellers and following up on lead generation and know that I have someone, a team member that is helping me with all of those things on a day-to-day basis.

Lindsay: It’s always that– we always talk about the doctor-patient relationship. It’s like you’re the doctor. You’re not necessarily the one that has to take their height and weight. They have a nurse for that. It’s like that’s the same when it comes to real estate. People taking the pictures don’t have to be the one that’s doing the negotiation. In reality, if you want to scale your business, you have to think about those time management type of things that, do you need to be doing this task or is there someone else that, number one, do it better and do it faster than you, I think that’s awesome.

Jessica: For sure.

Lindsay: What is something, though, that maybe you’ve held on to? You’re like, “I’m actually really good at this.” Is there anything that you’re like, “I’m not giving this one up?”

Jessica: As far as planning, I know just the whole input data, with the systems that Lamacchia has, they’re like, “Okay. Well, we’ll do it for you.” I’m like, “Okay, well, I like to log it on a piece of paper, and then I like to input it.” I like to input my own data. On the other hand, one thing I recently let go that I do not like doing, and I did not like doing it for years, and now I have someone doing it for me, and I’m like, “I can never go back,” is signs.

[laughter]

Lindsay: Yes, putting signs on the ground, especially this time of year, not fun.

Jessica: Yes, I don’t miss it one bit.

Lindsay: No? That’s amazing. Tell me how you market yourself. Let’s get into that because, closing 50 homes, you have to be doing some kind of marketing, not just for your listings, but also for you and your business. Give us a little bit of an idea of what your marketing plan is year by year.

Jessica: I have a good referral-based business. I have big supporters out there, who are always sharing the word and that is, ultimately– that’s my opinion– the best business is referral-based business. That is number one. Then, I also do have a good online presence with a lot of reviews. That has helped me tremendously with just people who are looking for an agent, has helped me with other agents looking for an agent to service their client in my area. That definitely has helped a lot.

Lindsay: A lot of agents don’t think about that, or they get through the sale, and that’s the end of that. They are done, right?

Jessica: Yes.

Lindsay: Yes, those referrals and those reviews are so important to impact more referrals.

Lindsay: It gives people a chance too to write down what they loved about you. Just like you said, you hold on to this task of writing things down because it helps you, right?

Jessica: Right.

Lindsay: It’s like they write it down and say how awesome you are. It just makes it embedded that much more in them, and they’ll want to refer you. It’s just it’s awesome. That’s amazing. As far as them referring you, though, obviously, you’re doing a great job for them, and that’s part of it. What else do you do for your clients throughout the year? How are you keeping in contact with them? Even though you’ve done an amazing job, it could be six or seven years till they need you again. How do you stay top of mind with those people?

Jessica: I make sure to stay in contact with my database throughout the year, never finish up a transaction and that’s it, and we’re never going to talk again. Monthly email blasts, calls, and then client appreciation parties. I’m geared up to do probably at least four this year. Doing that, and– people really love it. They enjoy it. They’re like, “Wow, this is awesome that you stay in contact so much after the closing,” and it’s just a good time for you to be able to catch up. Just constantly staying in communication with them throughout the year.

Lindsay: They’re loving you, obviously. They gave you also the Best Realtor of the Berkshires. This was not your first time getting this award this past year, was it?

Jessica: No, so I got that award the previous year as well.

Lindsay: I know it’s a little awkward.

Jessica: ’23 and ’24.

Lindsay: I’m sure it’s a little awkward for you to talk about because you’re very modest, but tell us about this award. Tell us what it means to you as well to win that two years in a row. It must make you feel really good.

Jessica: Yes, it does. I’m sometimes like a go-with-the-flow type of person. Even, I get to the end of the year and I’m like, “Oh, okay. I’m at the top. I sold 50.” On a day-to-day basis, that’s not really what I’m focused on. Sometimes, I get surprised by that myself because I just– I do my job, and I focus on that. Sometimes, I don’t realize it when I’m in it until after.

Getting that award, it is from the local newspaper. They host this every year for all local businesses and have the local community vote on the best of whatever category. I have a great following, and I put a good effort into getting people to vote for me to get to that. It was–

Lindsay: I’m part of it.

Jessica: -awesome to get it two years in a row. I got it the first year and I’m like, “I don’t know if I can do this again, but I’m sure going to give it my all.” I ended up getting it two years in a row, so [crosstalk]

Lindsay: It’s not enough to just be– You got to push for these things once you’re nominated for it. I think that that’s amazing. Obviously, they’re not going to vote for you unless they actually feel like you are the best. They went out of their way, and they came through for you. That’s awesome. Congratulations again on that. That’s amazing.

Jessica: Thank you. Thank you.

Lindsay: Listings. It’s been a crazy couple of years, right?

Jessica: Yes.

Lindsay: I think we’ll– it’s going to get more and more into a more balanced market here in the coming years. What are some of your tactics, things that you do to make sure that you get your listings sold? Is there anything that you can like, “This is something that I always do,” or pinpoint something that is your key to success.

Jessica: Just staying in constant communication, one, with your clients so you control the narrative. You’re constantly always checking in and telling them. I’m huge about getting back to them with feedback. “I’m selling your home. You’ve got to know what other people are saying.” Just staying in contact with them. Then, great photography is huge and great marketing. Then, just monitoring the listing as close as possible so if we need to make some adjustments, making those adjustments. It helps when you’re in constant communication with them when you get to that point, if you need to make some price adjustments, and you’ve been in constant communication. It makes that conversation a little easier.

Lindsay: For sure. Plus you’ve set it up ahead of time?

Jessica: Yes.

Lindsay: They know what to expect if that conversation does happen to happen.

[laughter]

Lindsay: If it has to happen, then at least they’re all prepped for it at that point. They trust you because they know that you’re going to do everything to get it sold and is the most money that you possibly can. What’s the most rewarding part for you now, being a realtor? What is it that drives you every day? Obviously, you don’t have any plans of going back to any of your previous careers. This is it for you. What is it that really drives you to move forward in this business?

Jessica: One thing that just makes it easy is that I love my job. I love what I do. That just makes it easy. I had a client who recently just said to me, this was three weeks ago, dealing with her, she’s like, “I can tell you, obviously, love what you do.” I’m like, “Yes, I do.” It’s nice for someone on the other side to be recognizing that as well. The reasons why they’re recognizing that is, obviously, because of how you act, the communication. Yes, I love what I do. It’s just it’s my drive. It’s my passion. Yes, I can never go back to one of my previous careers.

Lindsay: Although I would want you to make a drink for me because I bet you’re really good at that.

[laughter]

Lindsay: Tell me about the community involvement. I know that your passion for your career has also transitioned too into helping the community and being very active in the community. How do you choose what to be active in? What drives you to do and choose certain things? How has that helped you to deepen the relationships within the community as well?

Jessica: Obviously, being a part of your community, especially when you’re in a smaller community like we are here, it just feels like it’s just a deeper connection, I would say. I’m part of the community service board, which we do different things throughout the year, different fundraisers to raise money for different things. We try to keep it housing based, but sometimes we’ll branch off a little bit.

Then, my work with the Habitat for Humanity, that’s fun. I started doing that years ago, and I’m like, “Who wouldn’t want to go build a house for the day?”

Lindsay: So fun, so fun.

Jessica: Yes, and so working with them is great. I recently just started considering getting involved in some other things as well, just to try different things. Looking into– I went to my first Rotary meeting last week and going back again this week. Just learning a little bit more about that and getting exposed to that. Then, just, we’ve done different things with the food pantries, Thanksgiving Angels, and stuff like that. It’s nice to make other connections and just be out there in the community and just helping and giving back. It definitely– it’s a great feeling at the end of the day, and you make connections, and–

Lindsay: Yes, it just deepens the connections that you all have and that they have to you as well. Amazing. All right. I love to ask this question because it always brings up some fun stuff. If you have a minute to think about it, feel free.

Jessica: Okay.

Lindsay: I want to know the craziest story you’ve had in real estate in your career so far.

Jessica: Oh, gosh. [laughs]

Lindsay: Nobody– we’ll protect the innocent. What’s the craziest story that’s happened to you?

Jessica: Oh, gosh. There’s many.

[laughter]

Lindsay: I think it’s more of like, which one do you pick? [laughs]

Jessica: One time, I picked up my real estate sign with bullet holes in it.

Lindsay: Was it a competitor or [crosstalk]

Jessica: I don’t think so. I think it was in a rough area.

Lindsay: Oh my. Yes, maybe you send someone else to pick that up, someone that’s packing next time.

[laughter]

Jessica: Yikes. I’m trying to think what else. Oh gosh.

Lindsay: Craziness ensues every day. It’s hard to pick one. That’s so funny. Like I said, if you think of one, you let me know. All right. If you weren’t in real estate, if you hadn’t gone into this field, what do you think you would be doing right now?

Jessica: My guess is I probably would be still working in the dental industry. I had left work– I had worked in the dental industry for over 10 years and left to stay home with my youngest. I was going to stay home with her, and that’s why it was waitressing just to have a little something to do and bring in a little income. I guess probably I would have stayed home with her for that duration and then went back to that.

Lindsay: I think you would have done something else entrepreneurial because you have just been always so driven. Do you know what I mean?

Jessica: Yes.

Lindsay: If it hadn’t been real estate, it would have been something else. What do I know? I think you would have found something to drive you because you are just– you’re a workhorse. That’s just the way you are, and I love it. All right, parting words for our audience because we’re already at the end. I told you this was going to be short and sweet. What would be your biggest piece of advice? I know you already gave some advice to younger you and to your friends that’s in New York, but what advice would you give to realtors? Maybe they’re right around that 20 to 30 mark of sales, and they really want to get to that next level that you’re at. What would be some advice to help them leapfrog their business?

Jessica: I would just say, confidence and consistency. You have to be confident in yourself. If you’re going to sell yourself, if you’re going to sell something else, you have to be confident. Whatever that looks like. Sometimes I’m going into a listing appointment, and I sit in the car, and I have a little pep talk with myself before I go in. Just to be confident and then consistent. This business requires a lot of consistency, and you have to follow through. Just be consistent about whatever it is that you’re working on, lead generation, your calls, logging everything into your database, just be consistent.

Lindsay: I love it. I love the confidence, and I love that you give yourself a little pep talk when you go in because it all becomes mindset. I love that you said that because it really is so important. I know I just listened or watched something the other day where someone was saying that you should give yourself a high five in the mirror every morning, and it just sets your day off of like, “Go get them.” That just reminded me of, and I think that that’s so powerful. I love it.

Jessica, thank you so much.

Jessica: Thank you.

Lindsay: You’re an absolute joy. You’re absolutely crushing it as our title of our podcast says. Just keep doing what you’re doing, girl. I can’t wait to see what this year brings you.

Jessica: Thank you very much for having me.

Lindsay: I’m so excited to have had you. Thank you so much everybody for listening, for watching. Especially if you’re on Spotify, don’t forget. We also have Jessica’s links right here. If you want to go and check her out, give her a like, give her a follow, send her a message. She’s an open book, and she would love to meet any of you guys. Thank you all so much for coming and being on the episode today, and get ready for the next episode of the Agents Who Crush It In Real Estate. Thanks everybody.

Outro: Thank you for tuning in to the Agents Who Crush It In Real Estate podcast. If you enjoyed today’s episode, share it with your friends and colleagues and leave a review on your favorite podcast platform. If you’re interested in being a guest, email us at info at crushitinre.com. Thanks for listening. Don’t forget to crush it in real estate.

[00:29:52] [END OF AUDIO]

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 CrushitinRE.com/podcast. 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.