Episode 2: How Ryan Sullivan Built a Career in Real Estate (Twice)

Welcome to We Built This Life. Thank you so much for tuning in today. This is episode #2 and my first guest is Ryan Sullivan, who I’ve known for 20 years or more, and I wanted to feature him on the show because his career path has literally come full circle, and I always was really interested in his story. He started out his working life as a real estate agent when he was in his 20s, and he was busy but he didn’t reach the level of success that he wanted for himself. So after the stock market crashed in 2008, he made a change: He went back to school when he was 29, first to get his Bachelor’s degree than his Masters in Mental Health Counseling. He worked in the local school system counseling kids for a few years while he was in school, but he quickly returned to real estate after graduation. Ryan and I talked about what it was like for him to uproot himself and the life he had built to go back to school and pursue a completely different career path, and why, after the time and money he spent to make a career change, he left that new career path behind and decided to go back to real estate. Ryan actually used some things he learned in school to be more successful in real estate the second time around, and he figured out how to give back by becoming a volunteer for an organization that supports children who have been diagnosed with cancer and their families.

Getting His Start in Real Estate

But first, Ryan’s story begins way back when he was 18, and his parents, who had rented their house for 18 years, were working with a realtor to buy the place from the owner [CHK]. Ryan remembers the realtor coming to the house and he was taken with how professionally she was dressed and how prepared she was for her appointments. He said he just wanted to sit near her and ask questions and learn everything he could about her work. And that’s when he knew he wanted to get his real estate license.

But it as an incident with a tomato a few years later that actually led him to his first job in the business. He was working at an old-school video store at the time, and by this point he had finished his real estate licensing class, but hadn’t taken the exam yet. The video store had real estate magazines available for customers to take, and Ryan would study all the listings and how each agent marketed his or her properties. Because the agents’ photos were in the magazines and Ryan spent so much time looking at the listings, he would recognize the realtors when he saw them in real life. And that’s what happened one day at the video store when an agent, who Ryan calls “one of the queens of real estate” in the area, came in to the store. So the woman returns her video and she walks back to her car where her daughter and her granddaughter are waiting, and Ryan happens to look outside at the right moment, and he sees the realtor waving her arms in frustration then walking back to the video store. She opens the door and finds Ryan inside and tells him her granddaughter had dropped a tomato in the car and her daughter sat on it, so now there was this bright red stain on the seat and her car is brand new.

Ryan: “She was just in panic mode. So I grabbed the paper towels, I grabbed the Windex, it was the only cleaner I had, and I went out there and started cleaning her car. And she’s just looking at me in disbelief that I’m cleaning her car in this moment of panic that she’s having about her new car. It’s the way that I am. It’s the way I’m always operated. How can I be of service to another person? Which is something that will make you do really well in sales. But the interesting part of it was, she had known b/c I had mentioned to her that I had taken the class and all this. And she turned to me in that moment and said, go take that licensing exam. And when you finish, once you pass that test, here’s my business card, you give me a call.Now I was motivated to take the test. I went and took the test and sure enough I called her. And it was probably just one of those expressions people say, just give me a call whatever, but I was very literal at that age, so I was like, yeah, she wants me to give her a call after I pass the real estate exam. So I called her. And three days later, her husband calls me back and basically created a position for me to come in and start learning how to do marketing. So I came in and did marketing for her, which was just a great experience because I was learning from someone who was just selling a ton of homes.”

Ryan works with this woman for two years and along the way he gets his real estate license and he starts working in general brokerage as an agent for a company and he also worked for a builder selling new construction homes. He thought selling new construction would be the easier route to go as a young, new agent because he just had to sit in a model home and potential business would come to him. But that wasn’t exactly the case.

Ryan: “Back then, I didn’t meet with a whole lot of success. I didn’t need to make a whole lot of money because I didn’t have a lot of bills back then. But I just never really met with success and I think it was because I was really in my head. I was really in my head about making sure that I knew what I was doing. I got really scared when I didn’t know what I was doing. A lot of times that would keep me from doing more business because I didn’t want to harm anyone. It seemed so serious to me, and it is when you’er dealing with what for a lot of people is the biggest transaction in their life, that’s really scary as a 22, 23, 24 year old when you’ve never done it yourself, you don’t really understand the process.”

Making a Career Change

Still, despite having some challenges, Ryan still saw real estate as this growing, thriving industry to be in, and back then it was. The realtors that Ryan knew were busy, and they were selling a lot of homes. Then the stock market crashed in 2008 and as we all know, that brought with it hard times for a lot of people, especially in the real estate industry. That was something Ryan never thought he would see in his line of work, and he decided to make a career change in response to that.

Ryan: “When the market changed it was really tough for me because I was watching people in my life that I cared about and respected were losing their jobs and then they were losing their homes and they were losing vehicles. That was a lot for me emotionally to dael with beause 1. It’s people I cared about. But 2, I didn’t know this was a possibility. I didn’t know this could happen. So then there was a lot of fear that was involved here too. How long can this last and and what does this mean for my own career? Am I going to be able to make money to provide for myself? And I said, well maybe, you need to go back to school. And it was interesting because when I went back to school, the college I went to, the local community college I went to, it was all people in my same situation. I was so surprised by that. There were so many folks that were going back and it was based on the economy which is why they were back. They were laid off from a job or they needed to have some kind of skill set and a different career or what not, so that’s who was attending school at the time.”

While Ryan was working in real estate that first time, he was also a volunteer, and that helped him figure out the direction he wanted to go in for his career second act.

Ryan: “I had decided to volunteer, it was at a local resident treatment center, which for anyone who is not familiar with that, it’s usually foster kids at those centers and they have just gone through failed placement after failed placement and they are just not meeting with success in a foster family environment. So this gives them a chance to come and learn some new behavioral skills and some new coping mechanisms to try to help them be successful in a family environment. So these kids are at a real low point in their life. And they’re really struggling. I decided I wanted to volunteer there. I just wasn’t feeling so fulfilled career wise so what else can I do, how can I help someone else. And the reason I was there is because…I figured it’s close eough that I’ll actually show up and I’lla ctually go and I won’t let anyone down. So I show up and right away, there was this changre in me and I was like, “This is it.” I really like this. I really like working with these kids. And so I started doing some research and I decided that I wanted to do—I didn’t know exactly what it was yet—but I knew I wanted to do something working with kids and something in a counseling capacity.”

So in 2010, Ryan packs up his belongings and loads everything in his car, drives three hours away to a coastal town in Maryland, and moves in with his mom while he goes to school full-time. That first night when he arrived—after a flurry of activity, when he had moved into this new home with his mom and unpacked and begun to figure out how he was going to fit into this new life—he remembers lying in bed and everything was finally quiet and he started thinking, “What have you done? You left your job, you enrolled in school full-time, and you moved in with your mother, what have you done?” And he felt that way for a few weeks, right up until he drove the 30-minute commute to his new college campus. On the first day of classes, he pulled into the parking lot and found a spot, then he staying in the car, looking at everything that was going on around him. 

Ryan: “I’ve got my hands on the steering wheel and I’m just sitting in the car and I can’t decide whether I’m going to muster up the courage to go do this or I’m just going to drive back and figure out what I’m going to do with my life. And I said, you know what, you’re going to be successful at this. And I didn’t have any evidence in my head that told me I would be successful because I hadn’t been successful when I went to school before. But something in my head felt different. And so I went into the school and I remember I went to the first classroom. Luckily I found it beause I remember I was terrified I wasn’t going to find the room. So I find the room and I walk in and I see there’s a bunch of younger students sitting there. I was always the person who would go and sit in the back of the classroom and I just decided, you know what, I’m going to go sit in the front of the classroom. And that way if they’re making fun of me, it’s all behind my back, and the only thing in front of me is the teacher to focus on because that’s what I’m here to focus on is the teacher and learning, not caring about what anyone thinks of me being here. This is my journey. So I just got the confidence to say, you know what, I don’t care what anybody thinks of me. I’m here for me. I have a goal in my mind, this is what I want to do, and I want to do it.”

Coming Full Circle

Ryan was in school for the next eight years, ultimately earning his Masters degree in mental health counseling. For most of that time, he also worked full-time as a counselor in the local school system for the remainder of his college years so he gained a lot of experience in education. So he graduates and he has his diploma and he’s ready to start his new career. But he also has student loans he has to start paying and he thinks, hey, I better find a job that is going to allow me to do that. So he moved back to where he used to live, outside of Baltimore, and decided to go back into real estate, but this time he was going to use what he learned when he was studying to be an educator and he has met with a lot more success as a result.

Ryan: “I learned a lot about psychology, which real estate is more about people than it is about houses. So understanding psychology and understanding how people think has been really helpful as well because I can start to identify the fears and worries that clients have and I try to anticipate them upfront so I can give them a little bit of comfort before the fear sets in. And then you know, when it does set in during the transaction, that we can process it and we can work through it. So I thought I was going to school to be a counselor and work with children. And that is not really where that led. But I feel like I’m counseling adults every day. Because every day, somebody is feeling like it’s the end of the world, I can’t believe this is happening. And it’s so funny by the end of the call, they’re like, okay, everything is going to be fine, and I know that we’re going to do this and this. And that’s my job. And that’s one of the things that I think gets me the reviews that I get, gets me the referral business that I get. I understand the process better now, the real estate process. But I also understand people’s worries and fears and I understand their goals better.”

He also went back and used some of the tips he learned about marketing from the real estate agent who he met at the video store so long ago.

Ryan: “I don’t’ use a lot of social media. A lot of real estate agents are using their business pages and things like that. I’m horrible about my business page because it’s not the business I’m going after. I realize that I have this network of people that were brought into my life for whatever reason and they’re the people who already know me, like me, and trust me. So why wouldn’t I be trying to work more with them? Plus it’s so much fun. I love going into an appointment where it’s somebody that I already know. That’s so much easier than going into an appointment with a total stranger that you have to try to learn about before you can figure out how to help them. So I really do like using social media but I’m using social media in more of an old school kind of way. I’m not going after the masses, I’m going after the people I already know…From there, I write handwritten notes every morning. It’s something that I learned to do back then and I still do it. I love writing handwritten notes. I think that more so than even back then sticks out so much. If I go on an appointment, they’re going to get a card in the mail from me two days later just thanking them for meeting with me. Even if they never do business with me, I just want them to know how grateful I am that they picked up the phone and gave me a chance to interview.”

So Ryan is back in real estate, but he also went back to school for a reason. He had a genuine interest in helping kids and giving back, and he knew that he still had to find a way to make this a part of his life. While he was working as an educator, he was exposed to the population that he really felt called to give back to.

Ryan: “While I was working in the school system is I had a number of children diagnosed with cancer. And that was just a horrific experience for me. Watching kids I know go through diagnosis and then all the sudden not be in school and now they’re getting treatments and then the next time you see them, they don’t have any hair on their head. And then they’re in school, then they’re not in school and you’re just constantly worried about them. They’re coming back and forth. And as a school community, that hits you as well. How can we support this kid? How can we support this family? What can we do to make their lives better and let them know that 1. We’re behind them, but 2. The message always was we can’t wait ujntil you come back, we can’t wait until they come back, we can’t wait until they come back. Because when a kid is thinking about this diagnosis and a parent is thinking about this diagnosis, we need them to know, we expect you to come back. So we’re not forgetting about you. We’re going to have a place in the class. We’re holding a place. Your desk is still here. So we’re not just getting rid of that because you’re not here day to day. That just really sparked something in me and I knew that once I wasn’t in education anymore, then I kind of knew, that’s what I’m called to do. I’m called to work with these kids who are going through these really hard diagnoses with their families.”

What I thought was interesting that Ryan said is that now he is this successful real estate agent—he won an award in his old company—but he sets his goals for his business and his work based on the number of events he wants to coordinate as a volunteer. So he pays for the events and they cost a certain amount of money, so he knows he needs to sell a certain number of homes in order to pull off the volunteer work he wants to do.

Ryan: “I have to think, oh, I want to do these three different ideas that I have to give back. So in order to do these three different ideas, these three things that I want to do to give back, that means I need to sell this many houses this month. So I really have to take that and tie it into my goals. Because I realize again, that’s what fulfills me. The work doesn’t fulfill me. I love going out and working with people, I love the day to day interaction, but what truly fulfills me is giving back. If I don’t tie that to my goals, then I’m going to burn out. But as long as I can tie it to my goals, then not only will I be able to hit the numbers that I need to hit at work, but I’ll also be able to do the things outside of there that is going to make me feel fulfilled and make me feel like I’m contributing to the population that I serve.”

Key Takeaways in Ryan’s Story

When scared or anxious, work on reframing your mindset: So I loved hearing Ryan’s story and a few things stuck out to me from this episode. The first is the image of Ryan sitting in his car in this college parking lot, holding on to the steering wheel and looking at the other students, most of whom were younger than him, and he’s scared and he doesn’t know whether he is going to go actually go to his classroom and really take his life in a different direction, and he thinks for a minute or two or five and then he tells himself, “I am going to be successful at this.” He made the decision to look past his anxiety and his fear and to only see success in his future, even though he hadn’t been a good student before. So—I’m not one for daily affirmations and visualizing goals in order to manifest them or I never have been in the past—but maybe there is something to imagining the person you want to be and just deciding that you are going to accomplish a goal, pushing aside all the reasons you shouldn’t do it, and then going after it.  

Don’t be afraid to pivot your career, even if it means going back to a past pursuit: The other thing that stuck out to me is that after dedicating so many years to school and studying so he could work in education, Ryan went back to real estate afterward, and he didn’t really have an internal struggle about it. He decided that even if he wasn’t working in education, he was going to use what he learned in school to make him a better realtor, and then he found a way to still satisfy the part of him that still likes giving back and working with kids and families by dedicating a lot of his time to volunteer. I think a lot of people, myself included, would have had a hard time making the decision to go back to the work they did before they spent all this money and time getting educated to do a different career. Of course, it’s okay to change course with your career and then go back to your original course and then change again, and I love that Ryan didn’t get himself a hard time about that.  He really followed his instincts about where his career path should go next.  

And with that, that concludes this week’s episode. I hope you found something in Ryan’s story that you can take away and apply to your own life. I certainly enjoyed learning more about his professional life. It’s funny; we have friends that we’ve known for a long time and we obviously know some things about him—I knew Ryan is a volunteer and a real estate agent—but I didn’t know what his motivations were for the career choices he has made. And I thought it was really interesting that he defines success almost by the number of events he can do as a volunteer; his real estate goals are tied into that. I think that says a lot about him. Thank you for tuning in today and listening to his story. I’ll be here next week. Until then, take care.