Dan O'Halloran - Running A Real Estate Team & Investing
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Join us for an insightful conversation with Dan O'Halloran as he shares his expertise in running a successful residential real estate team and navigating the world of real estate investments. Leading the O'Halloran Group alongside his wife Christina, Dan oversees a dedicated team of agents and administrative staff in the picturesque Lake Sunapee Region of New Hampshire. Beyond their team, Dan and Christina have strategically invested in various properties, including their office building, and a lake home utilized as a short-term rental. Through a gradual accumulation of assets and strategic moves, Dan discusses how they've steadily built momentum towards achieving time and financial freedom through real estate. In this episode, Dan also emphasizes the importance of team building, cultivating a strong organizational culture, and actively engaging with their local community to establish a lasting presence and impact. Tune in to gain valuable insights and strategies from Dan's journey, and discover how you too can leverage real estate team leadership and investments to build long-term wealth and success.
In this episode, you will be able to:
- Master the art of building a robust real estate investment portfolio.
- Uncover the secrets to successfully starting and growing your own real estate team.
- Discover the countless benefits of joining forces with a real estate team.
- Cultivate a thriving real estate team culture and propel exponential growth.
- Unveil the strategic commercial property investment approach for maximum returns.
The key moments in this episode are:
00:00:00 - Building Multiple Streams of Income
00:02:41 - Getting Started in Real Estate
00:03:45 - Real Estate Investments
00:07:03 - Benefits of Owner Financing
00:13:38 - Building a Team
00:17:27 - Benefits of Joining a Real Estate Team
00:23:44 - Leading by Example
00:24:11 - Fostering Team Culture
00:25:55 - Team Bonding and Community Support
00:26:48 - Connecting with Dan
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Dan O'Halloran
How do we better insulate ourselves with the, you know, roller coasters of the market conditions and economy? And her parents had a restaurant for over 30 years, and they owned it, and it was how they were able to weather storms and edge. I give credit to Christina. She was like, no, if I. If we own a business and we should own the property where it's at, and then we're beholden to ourselves and no one else. And it was a wonderful ethos that she had with that and helped drive and push us forward to look at opportunities that we could capitalize on.
Mike Swenson
Welcome to the REL Freedom show, where we inspire you to pursue your passion to gain time and financial freedom through opportunities and real estate. I'm your host, Mike Swenson. Let's get some REL Freedom together. Hello, everybody. Welcome to another episode of REL Freedom, where we talk about building real estate, leverage freedom, building time and financial freedom through different opportunities in real estate. I'm your host, Mike Swenson. If you want to get started on your real estate investing journey, feel free to go to our website, freedomthroughrealestate.com. We've got some good articles. You can watch some of our videos and help educate yourself on how to get started with your journey. For today's guest, I am so excited. We have a traditional real estate agent building and growing a team. Also doing some investment stuff on the side. As with a lot of people in real estate, they're building multiple streams of income. Kind of allows you to shift as the markets changed or be able to build and scale multiple areas of your business. Or as time allows, family and life allows, you can do that. So we've got Dan O'Halloran here. He's a real estate agent in New Hampshire. And so you can kind of talk about your niche. Has had some multifamily properties, some short term rentals as well, in addition to building your team. So welcome to the show, Dan.
Dan O'Halloran
Yeah, thanks so much for having me. Super happy to be here.
Mike Swenson
Why don't you go ahead and just give us a little bit of a background before real estate and getting into real estate, and we'll take it from there.
Dan O'Halloran
So I got into real estate back in 2005. I worked in the financial industry when I graduated college. And then my father actually is the one that convinced me to that I was not enjoying my job and that I should go up and get my license and sell houses. He was actually building at the time. And I begrudgingly initially told him that I was totally happy and loving what I was doing, even though I was miserable and wouldn't tell him that he was right for a little while. But I did research, analyze the industry, and I really like that you can control the impact you had on your clients and the marketing, messaging, and that control factor I really liked so it could fit better with how I thought people should be taken care of. So I jumped in in 2005 and hit the ground running. Then the market died, which is exciting, and then rode through all those transitions and changes as an independent agent with some small brokerages and then joined Keller Williams Realty in 2017 and started building a team. And today we are at. We have eight people on our team, two on the staff side of the house, operational support, and then five agents.
Mike Swenson
Yeah, I love building teams. You know, me having been on the admin side of teams for a long time, it's fun to see how you really can celebrate the best of what each person does and put it together and form a good, strong team because you've got your admin, gifted people, you've got your agents and even agents. The best analogy I ever heard was, you know, a sales team is kind of like a mixed bag of nuts.
Dan O'Halloran
Right?
Mike Swenson
Like, you get that mixed bag of nuts at the grocery store. Everybody kind of likes a different one, and they've all got a different flavors, and each person can work together to be an agent on a team and be successful. So, yeah. In addition, before we kind of dig deeper onto the real estate team side, talk about some of the investment side of what you guys have done.
Dan O'Halloran
Sure. So we were able to buy our office building, which is two residential units and two commercial units. And then we had an opportunity to buy the building behind us, which is another three units. And then we bought a property up on the main coast, which we short term rental as well. So.
Mike Swenson
And for those watching, the background, is your property.
Dan O'Halloran
No, that's not the main.
Mike Swenson
Oh, that was a joke earlier, which is.
Dan O'Halloran
Yeah.
Mike Swenson
Oh, this is.
Dan O'Halloran
This is Lake Sonapeast. This is. This is our. This is the lake in our town, that most popular, highest value lake. Yeah, got it. And then our property in Maine is not that view, but still very nice view. Yes.
Mike Swenson
Well, it is beautiful. And that's the part about being up in New Hampshire, is there's a lot of beautiful scenery. So.
Dan O'Halloran
Yeah.
Mike Swenson
So I'm curious to hear, like, the why behind. You know, for a lot of people, especially real estate agents, they're busy slinging homes. Right. Busy working with clients. And a lot of them almost forget to or are too busy to put on the investor hat and say, I'm sitting in an industry, that I have an incredible amount of opportunity. But like I said, so many of them just either are short sighted in their thinking or don't take the time to plant those seeds as an investment. So talk about just those conversations of, yeah, let's pick up an investment property, or let's have an office building and why you want to do that or what that's going to do for you and your goals.
Dan O'Halloran
Yeah. So it was really interesting. Um, so it's coming up. June will be 19 years that I've been selling real estate, and for the majority of my career, the. And I love the people I worked with, but not a lot of people were actually investing or having conversations at a level about investment properties and stuff like that. And so I'm very frustrated that my first house that I bought was a single family home, not a multifamily. It's, like, one of my biggest regrets. Same here. It was awful. It was all purely because we were renting in this townhouse, and this guy kept opening a stupid door on the side of my car, and I was losing my mind. And it was in 2007, before the market crashed. I was like, I'm selling real estate. I should have a house or some sort of property, and this guy's denting my car door every single day. I can't stand it. I just want a house and have my own zone. That's mine. And so we bought a house at the top of the market, and it was brutal, and we sold the house, and we didn't. We didn't, like, you know, lose it or anything like that. A lot of people did in that time. But, yeah, it was frustrating, and I wish I had done the multifamily thing. So once we switched and joined, and not trying to make this a plug for Keller Williams at all, but, like, honestly, like, it was the first time I've had people then suddenly be like, we're doing all this investing. Have you ever thought about it? This is how this has worked for us. And the conversations have started happening at a pace and a level that I wasn't used to, which was really awesome. And so my wife and I started thinking about, you know, what does our investment portfolio look like? How do we better insulate ourselves with roller coasters of the market conditions and economy? And her parents had a restaurant for over 30 years, and they owned it, and it was how they were able to weather storms. And I give credit to Christina. She was like, no, if I. If we own a business and we should own the property where it's at, and then we're beholden to ourselves and no one else. And it was a wonderful ethos that she had with that and helped drive and push us forward to look at opportunities that we could capitalize on. And so our first building was amazing. Like the. For our office, the guy that owned it, for some reason, was super nice, and it was a handshake owner finance deal, and we were able to buy it and close real quick and start renovations and set up shop very quickly. And then getting it rented was very easy in our town. So the office carries itself, but then we can do pass through rent to ourselves. So we have it in our team, LLC rents back from our building, LLC.
Mike Swenson
You mentioned a couple of basic foundational things that don't always seem basic and foundational. Number one, thinking about, if you haven't owned a property yet, like what your first one's gonna be. So for those folks listening, really thinking about, can my first purchase be something I can turn into an asset in the future? And, yeah, if it is single family, great. But is it something that could turn into a rental property? If I was advising past Mike on what to do, it would be, you know, have that first property be multifamily. But we bought at the top of the peak of the market, just like you, and watch the values go down. And then the second piece is buying a commercial space. If you're somebody like yourself that has a business, you can be a tenant in your own building. And. And so I have seen a lot of people do that. And so if you're listening to this and you have a business, yeah, maybe there's a way where you can leverage that. And to your point, finding an owner that's going to be willing to work with you and do some seller financing. You know, a lot of people think, I have to have great credit. I have to have this, I have to have that to be able to get into investing, and you just have to find a willing partner. And so for something like that, you know, they might want to see some financials, they might want to see some background, but they might be okay with that, because if that person has owned that property long enough, they know it produces income, and they're confident that if anything went sour, they would just take the building back if they could. And so that's the benefit of something like that. So you're planting these little seeds, doing what most people aren't willing to do, which is buy the building you rent yourself. But it's not that big of an undertaking, depending on what building you're in, and that's going to really help propel you forward in the future.
Dan O'Halloran
Yeah, it never hurts to ask the question. I mean, someone can always say no, but if you're looking to buy anything and always ask if they're open to owner financing can work out really well, and there's certain situations where it won't, and that's fine. But if they say yes and the terms are agreeable, then rock and roll.
Mike Swenson
I mean, as somebody that works with investors, that's a conversation I have with my clients now is before we list a property, I always ask the question, talk to me about your appetite for seller financing, because I guarantee you I'm going to get ten questions from people. Are they open to seller financing? And yeah, you might get told no 99 times out of a hundred, you only need that one. Yes, but like you said, it doesn't hurt to ask the question and find that person that's willing. And now you've got a great asset and a great opportunity because you were open to asking the question.
Dan O'Halloran
It's great. It's been no regrets there at all. So I wish it was a little bigger, but it's fine.
Mike Swenson
So you're saying you want to move into a larger property, huh?
Dan O'Halloran
Yeah, or it's. Yeah, I know. Or it's go upstairs and take a tenant out, which I don't want to do, but the team's growing a little bit, so it's, it's getting a little tighter, but it's fine.
Mike Swenson
And for some people, you know, they're so busy being residential agents that you gotta carve out some time to be intentional with some of this stuff, to be able to look back five years from now and say, hey, a decision here or a small decision there is really going to change the game to where now you've got a few properties, you've got some assets, because you did a little bit here, a little bit there. You're not going to necessarily make tons of money overnight, but these few things are going to add up to five to ten years from now. And that's what I really want to encourage those residential agents to think about.
Dan O'Halloran
Well, and the longer you're, the younger you are when you acquire it, and the longer you hold it, the better. So I'm like about to turn 43, which is terrifying to me. And it's like I'm getting like, well into my forties, not like I can still see 30 anymore. I'm in denial of age at the moment. Which I know plenty of people say you're young, but still, like, I don't know, it's going too fast. But I think that, like, for us, we're looking at like, man, I wish we had bought more properties in our thirties or because that time of paying off the property and not having a mortgage and the return that can be generated from is huge, right? And building that equity, so versus buying something when you're like 60 in a 30 year, no budget at 90. And that's a little, that's a little different to start that mental shift that happens once you hit that point. And so it's really cool to have things start trending. Like, our thing is trending to, like, everything being pretty close to paid off by the time we're 60 or paid off well before 60, right? Some of our things we paid off in our fifties. And so, like, then there's no debt load and there's total control whether we want to leverage it to buy another something else or not. I mean, we're actively looking at opportunities as well for what we can find in our area too.
Mike Swenson
And I know one of the phrases we always used on our team was, you know, the two best times to plant a tree are 20 years ago or today. And so if you're there thinking, you know, about to hit 43 and you're like, oh my gosh, I haven't done anything as it relates to investing in real estate. Well, you could say that. But then what's going to happen 20 years from now? Would you rather just wallow in self pity for the next 20 years or say, I can start today, I can get my first investment, I can, can do my first thing so that 20 years from now I can look back and say, I'm glad I started at 42 or 43 instead of not doing anything at all. And then the other thing that I always think about is I remember listening to a podcast and they were talking about how people live longer now in the future. And so there was a guy, his mantra was alive at 125, and his goal is to stay living until he's 125. And he's like, I believe that I can do it. And so he's taking care of his body. Where now you look up, Dan, like, you might only be at the one third mark of your life if you make it to 125. So there's still a lot of 30 year mortgages that can get paid off between now and 80 years from now for you.
Dan O'Halloran
Wild concept real estate agents.
Mike Swenson
Are you tired of letting the busyness of life get in your way from achieving your real estate investing goals. I'm super excited to announce we've created the REL Freedom investor agent tribe. It's a place for you to come get educated and network with others so that you can make sure that you're hitting your real estate investment goals. So find out more on our website, realfreedom.com. Click on the store link. We've got a membership, we've got a mastermind group and some private coaching as well. Check it out. I've priced it super low. The goal is to get you and not have price be a determining factor to keep you from your goals. So come check it out. Schedule a call with me and we're happy to see where your real estate journey is going to take you. Let's talk a little bit about your team. Like you said, having your eyes open to building something bigger, you certainly can be a solo agent and you can be very successful. But talk about building a team, why did you want to do it? And then we'll go from there.
Dan O'Halloran
So being in business for quite some time, so it was twelve years by the time I joined Keller Williams. And they were, they basically, I was independent agent, didn't have a team, I was doing everything and then they, Keller Williams was talking about the team model and how all that works and it sounded like a foreign language to me and took about a year to start figuring it out right and start growing the team. But part of the reason first starting the team is you hit a production ceiling and a service ceiling where you can only take care of so many people at one time at a high quality and have that care, attention and service to their needs at the appropriate level. And you hit that capacity. And I hit that capacity multiple times. And it was frustrating because you want to like give your all to it, but you also want to like feel good at the end of the day and not be totally exhausted. Right. And so we decided, all right, well, it's, and my wife and I, we've been, she runs a company with me in our operations side of the house and we've always talked about working together. So essentially it was build the business just a little bit more so she can step away from her full time job in pr and marketing and step into, you know, this side of things and help me grow the business. And without her, I don't think we'd be where we are. She's. But it's amazing how we thought we were really similar. Then we started working together and I was like, oh God, we're not so similar, but all the right compliments in between. We looked at, all right, if we build this team, then we can provide this high level of service and segment out responsibilities that come across the way of buying residential real estate and help our clients really just have the best experience possible and being taken care of. Essentially, we're able to kind of systemize and structure our team and process in such a way that we hopefully, I think we do create probably like the one of the better services and experience someone can expect when they're buying real estate in our area. Yeah.
Mike Swenson
And I know for a lot of people, they think about hiring that admin as an expense. Right. And when done well, that admin can really be an asset for you because it can allow you to grow more than you thought you ever could. And if you're paying that person, you know, x amount of dollars per month, or however it's structured, you can go get twice the amount of business or, you know, something like that. And so now, that doesn't mean all of them work out. And in a lot of cases, you might have to find that right fit. But when you do that, you can build systems that make it so it's less dependent on that one individual being present or not. You can automate some things to where the point is. Yeah, you can grow your business and blow past that ceiling that you were hitting and didn't think you could ever get over that hump.
Dan O'Halloran
Absolutely. And it's that, um, the other part of that, too is it's just, it's human power. Right. And the more awesome people you bring into your world, the greater the sum total of all your parts is going to be. Right. And so we have amazing people that work for us. But the thing that I've really enjoyed with growing the team is seeing the development of the people that work for us and where they started at and to where they are now has been really, really cool to see that growth. And so, beyond the fact of great customer care and service and helping them make great decisions around real estate, the growth of our team members and how we've tried to support them and their goals and where they want, what they want to accomplish, that has been probably one of the most rewarding things, I think, for me, at least on our journey of building our team.
Mike Swenson
Now, if I was listening to this podcast and I wanted to get started in real estate, and maybe I wanted to learn and be an agent, what would be the benefit of me joining a team versus, hey, I can do it all on my own. I know there's stuff out there sometimes where people say teams are dead, teams are going away. Some people are like, why would I ever join a team? They're just going to take x amount of my commission. But I truly believe when done well, there is this huge win win that happens when you pair the right person with the right opportunity on the team. So talk about how that can happen for somebody looking to get into real estate or looking to grow their business. Why a team versus just trying to do it themselves?
Dan O'Halloran
Yeah, I mean, if you're having the same conversation with yourself every day, you're going to get the same result. And so having, you know, other people to collaborate with and try to get to a common goal is always going to lead you to a better decision. And I look at, with teams you look at, especially if you're newer, you don't know what you don't know. And I mean, I've 19 years doing this over, I don't know, I think over 700 transactions I've been involved in. Like, I've seen a lot and I still see new things every single day and I still know people that I've seen more than I have and I still call them and ask, have you seen this? What would you do? What are, what's your opinion? So I think if you're getting new into real estate or thinking about a team, I would say a component of being humble and asking questions because you don't know what you don't know. I think the support a team provides is amazing. So part of real estate is you get text messages, Facebook messages, WhatsApp messages, phone calls, emails. Like, the communication stream is nonstop and coming from every angle. And it's hard to step away and go on vacation and unplug. And there's that quality of life component or work life balance. And I don't believe in, like, there's never like a full 50 50 balance, but there's enjoyment that occurs. And when you're enjoying stuff, you shouldn't have regret about not being somewhere else. Right. And so if you're going away on vacation, you shouldn't have a bunch of anxiety about being away from your business. And so I can say with us and how we've structured our team is we want our agents to be able to go away on vacation and know that they're traveling, they're having fun, enjoying life, and everything is just carrying on forward for them and we're doing our best to take care of business for them, their clients, and making sure things are still happening so they come back it's not a mess. It's, you know, there's a lot of communication that they might have been copied on, but there's not a lot for them to do except for say, hey, I'm back and I'm your primary point of contact again, and let's rock and roll and keep going. And that to us is really, really important because, you know, travel and time off, at least my wife and I is really important. And making sure that our team members have as healthy of a real estate lifestyle as possible is important.
Mike Swenson
You know, I remember hearing somebody say, well, if you can't cut it as a solo agent, then think about joining a team. And it's really not that at all because right to your point, it's what do you value for some people, they love that leverage that a team can provide, that I can go on vacation and turn off my phone or I can spend time with my family when I want to spend time with my family when I'm not on vacation, but I'm still here because I have other parts working. You know, you've got that assembly line where other people are doing things and then you also get to do more of what you love. If you're not that type of person that loves detail and admin related things, you don't have to do that as much because you have great support that can help you. So you get a chance to spend more time building relationships if you really want to do that. And then the people that are on the admin side who really love doing details can handle all the details. And so it really is the best of all worlds when you find a good, functioning, well oiled team. But yeah, just like anything, there's poor teams out there, there's poor fits. And so I know for me, I was always concerned with helping people to find a team that was a fit for them and what they were looking for and really create the win win.
Dan O'Halloran
And that team helps you grow. So I know, like, there's a lot of focus on like, commissions and splits, but it also depends on what's the volume of business the team's going to help provide and bring to your, to your table because there's a component of you get into this and okay, this team is offering, or this company's offering the best split, but then you're just sitting there and you're not getting anything and it's you by yourself again with a couple of people to ask some questions, but not a lot of business coming your way versus other teams that might have a different split, and you're getting a high volume of business, a high volume of opportunities and interaction at different aspects of the market to really accelerate your learning and growth in the business.
Mike Swenson
Yeah, and there might be things that some people, you know, pay for that marketing or pay for isas to really help accelerate your business. And even just the basic email marketing, you know, staying in touch with your sphere type marketing, doing client events. Like there's all that stuff that a team can provide that you don't have to plan your own client event. Your team can help plan that for you. So, yeah, there's a lot of things that are a win win, and yet it's not necessarily what's the split. And I'm going to go to the team with the best split because probably the team that gives you the best split probably does the least for you. And so it's once again finding the win win, finding the total value. Who's going to help accelerate your growth?
Dan O'Halloran
Absolutely.
Mike Swenson
Out of curiosity, are there other folks on your team that do investing in other properties or other stuff?
Dan O'Halloran
Yeah, so Josh and our team, he came on with us in 2018 and we hammered on him pretty good about buying investment property and stuff. And I still remember when he bought his first one, so stressed out. And now that thing is rock solid. It's awesome. He picked up another property as well and building his portfolio, too. So it's been really cool to see him build and insulate his income with those properties, and it's been awesome. So we talk right early on on investment properties and building wealth and everything, and our whole team, we try to get everyone else to do it, and some of them are loosely coming around. You know, everyone has their sticking points of what they're interested in doing.
Mike Swenson
So, Robert, I think a lot of folks, it doesn't quite register of like, what am I going to do if I stop selling houses? Or what if I didn't have to sell as many houses because I had x amount of income coming in or I'm building equity through those things. And so I know for a residential agent, sometimes it's a challenge to really think. It's almost like you have to compartmentalize my real estate agent business. And now I'm going to go over to this box and think about future me and what do I want that to be. But when you have a great team that can push each other, just like for you, getting at a brokerage, that really helped you to think differently. Now it opens up those conversations and people on your team see what you're doing. And now they're like, oh, I want to have that, too. Oh, he has all these properties. How do I get started with that? And so you can really be an example for other people coming on the team and in the market center.
Dan O'Halloran
No, it's been. It's been awesome, and I love talking to them about it and helping them plan.
Mike Swenson
So talk a little bit about team culture, you know, being able to bring people in and keep people on the team that. That want to continue to be there. And I know real estate is a tough industry. So many people come and go between teams and brokerages and getting out of the industry. But how do you try to foster a team culture?
Dan O'Halloran
Um, so, I mean, we have a kind of an open office, so we're all here to, like, essentially, the way Christine and I built it is, you know, we're here to support each other. If you help somebody out, it's not. You're saying, you owe me dollar 100 because I showed that house for you. That kind of mentality was one of the things from, like, the owner of small. When I was, the company I was with the longest was a small real estate company, and it was like a family thing. Everyone would just kind of take care of each other. So I wanted to recreate that as much as I could and then kind of optimize that. Right. So, Christina and I really got down to our core values of leading with curiosity, client first and always asking, why not? Why not? And then trying to find people that can be on our team that can meet those standards. And part of what we've done is also just really work with our team as far as planning. So, every year, we do our, what we call our gps, our goal. Goal priorities and strategies. Right. And so that's been really helpful. And we reference those regularly throughout the year to keep us on track. And whenever we do that, there's a heavy focus on personal goals, not just, you know, the business side of things, to make sure everyone's really personal forward as well, because your personal life really impacts your business life. So we focus a lot on planning and a lot of time together, but the other thing that kind of ties our team together is everyone's obsessed with food. So we have lots of outings to. To go food based pretty much anywhere we can all travel together as a group, we definitely do that. But culture wise, other than some of those things, I mean, we're just a pretty tight crew and like to support and help each other out and then community events and stuff like that, we all do a lot together in our community to help support the community and work together while we're doing it, which always feels nice.
Mike Swenson
Yeah. I think having a residential team, the community is important, especially, I mean, depending on the size of the town that you're in or, or city or urban area, but being able to support the community that you're a part of and find those times to connect with people outside of the once every seven to ten years that we're going to help you buy or sell a home.
Dan O'Halloran
Yeah, absolutely.
Mike Swenson
Dan, it's been so awesome to have you on and to be able to share your story as an agent, as somebody building a team and growing a business as a landlord, owning commercial spaces and owning other investment properties, and even vacation home as well. For people that want to reach out to you and learn more about you. How can they do that?
Dan O'Halloran
They just go to o hgrp.com. That's our website and everything is right there and I'm happy to connect with anyone that wants to talk.
Mike Swenson
Thank you, Dan, so much for coming on and sharing. Best of luck as you continue to grow in the future.
