How to Build Confidence, Overcome Fear, and Create Real Estate Opportunities

Dana Flanagan (00:00)
It really comes down to trusting yourself and having confidence. And so I’ve done things over and over again. And a lot of times that’s what what I call kind of the unsexy, boring work behind the scenes that a lot of people don’t want to do or they feel like, “This is boring. This isn’t going to get me ahead.” Well, it’s the boring work that makes you successful. And so it’s also just doing, you know, it’s also going into that networking event that you’re afraid to do, picking up the phone and calling that person, asking for the job or the opportunity— that builds confidence. Confidence doesn’t come from sitting and waiting and just show up at your door one day. Confidence comes from doing—

Meghan Escobar (02:09)
Hello everyone, welcome to another episode of Real Estate Pros Podcast. I am your host, Meghan Escobar, and I am joined today by somebody who I’ve been pretty excited to chat with— Dana Flanagan, who’s got quite the— quite the experience in the real estate world on many different levels and currently making moves and being able to help brokerages drive forward business through providing strategic analytics, if I’m not mistaken. I think I got it right, but she’s gonna tell us more about it in her own words. So, so happy to have you here, Dana. And I think our listeners are really going to be able to take something away of the way that you’re approaching and how you’re able to help brokerages level up. So go ahead and dive in and tell us, for those of you who might not be familiar in your world, give us a 30,000-foot view of what your main focus is these days.

Dana Flanagan (03:07)
Yeah, thank you so much for having me. It’s such a pleasure to be here. And so just a little bit about me: I have a 25-year real estate background and I’ve done everything from residential real estate to flipping homes— we had a home flipping business. I’ve done mergers and acquisitions, multifamilies, commercials. So I’ve— I’ve had a white-glove service concierge for family offices and high-net-worth individuals. So I have a lot of different facets of real estate that I’ve participated in. Residential was my bread and butter for a very long time. And as I’ve evolved and— and you know, moved locations physically, I no longer wanted to continue— you know, I didn’t want to die doing that, right? So I wanted to have, you know, something else that I created that was my own. So during COVID, I created that— that white-glove service concierge for family offices and high-net-worth individuals. It led me down the road of kind of like the funding world and the, you know, hotels and resorts and development world. And so people would come to me asking me for funding, and I wasn’t quite sure what to do with that, but I’m a very, very big business development driver. And so I kind of learned that that field as well. And now I’m a partner at a capital firm, but I’m also the vice president of growth for a company called Brands by Integra. And we are a company that’s been around for a while. We do mergers, acquisitions, purchases, and partnerships with brokerages and agents in a non-traditional way. So we, you know, we help brokerages scale and it’s not a one-size-fits-all opportunity. It’s an opportunity for us to have a conversation and to create a partnership that works for everybody and in everybody’s best interest.

Meghan Escobar (04:51)
Thank you for that explanation. And you know, that’s a big piece of what caught my attention when we were discussing before hopping in here. You know, the way that you’ve been able to, you know, insert yourself into this world. We talked about some of the opportunities that you have coming up— the— the mergers, the acquisitions, the volatility, and the uncertainty that I think a lot of people are having, which isn’t— it— it’s not an easy thing to navigate through in this climate. So, tell— tell us, Dana, you know, what’s been the key to keeping your machine running smoothly.

Dana Flanagan (05:24)
Yeah. Well, I wouldn’t say that it runs smoothly all the time. I mean, there’s been a lot of fail-forwards and there’s been a lot of changes. You know, one thing I will say is I’m not afraid of change and I am not afraid to make moves if it’s not working for me. So I’m not afraid to pivot. And I think that’s what has allowed opportunities to be able to present themselves is I seek out opportunities and I— I really truly try to create something from nothing. Sometimes it doesn’t work and you have to pivot, but it works very well with scaling businesses and business development and growth. And so that’s what I do is I work alongside other leadership in this company to scale this business— to acquire brokerages, partner with them, purchase them, and then give them the tools and the opportunity to be able to scale. Whether it’s a broker-owner that’s looking to step back from their business a little bit or maybe not be so hands-on, you know, running around showing houses every single day, we’re— we allow them the opportunity to do that. Perhaps we’re taking on the operational side of their business and that helps them out tremendously, gets rid of some overhead, and we’re able to help them just kind of relieve some of those pain points. So it’s really nice. One thing I really like about it is that we are not one-size-fits-all. So a lot of these companies out there, it’s, you know, you do agent attraction, which is a revenue-share program, you bring the agents or the brokerage into that particular real estate brokerage, and they will not make any accommodations for you. They’re not going to roll out the red carpet. They’re not going to buy you. They’re not going to change a contract because you have, you know, 250 agents— they’re just not going to do it. And so you are like everybody else coming in. The difference with us is that we listen to your needs, we dissect the problems and the pain points that you’re having, and then we come in with our value proposition and we position you to win. And that can be different for every single agent— whether a brokerage is looking to scale and grow their, you know, business by a hundred and fifty, two hundred percent, or they’re looking to step back from maybe the operational work, or they’re looking to just kind of hand it off and— and get something for it, we’re there to be able to craft that proposal and that opportunity for them to do that.

Meghan Escobar (08:20)
Very specific to each person. I love how you, you know, mentioned there’s no one-size-fits-all. I think that’s across any industry. And so you’re able to really position yourselves in a— in a very specific niche, which is pretty important. One thing that you said I actually had to write down, I— I thought was really powerful and I— I wanna dive a little deeper into it, because this is something that I think we all face: fear, right? You mentioned not being afraid of change, and that’s that’s a huge statement— I— I think for— for anybody in the— the operations world or the entrepreneur world. And it’s not that it doesn’t come up for you. Is that safe to say, Dana? The fear is there. How do you— how do you navigate through it, or— or what’s something that— what’s a valuable piece of information that you can provide here for a listener that might not know how to overcome a fear?

Dana Flanagan (09:18)
You know, it really comes down to trusting yourself and having confidence. And so I’ve done things over and over again. And a lot of times that’s what what I call kind of the unsexy, boring work behind the scenes that a lot of people don’t want to do or they feel like, “This is boring. This isn’t going to get me ahead.” Well, it’s the boring work that makes you successful. And so it’s also just doing, you know, it’s also going into that networking event that you’re afraid to do, picking up the phone and calling that person, asking for the job or the opportunity— that builds confidence. Confidence doesn’t come from sitting and waiting and just show up at your door one day. Confidence comes from— and so I’m confident in my capabilities and I’m confident that I’m gonna be making the right decision for myself. Many of those things have not worked out. And that’s just part of being successful, because if you’re not failing forward, you haven’t tried, right? So I’ve learned a lot in my lifetime and I’m able to kind of seek out the red flags a little bit more so than maybe, you know, 20 years ago. Not every opportunity is a good opportunity, but I think it’s that trust in yourself and— and really having that— that knack to not get too excited. There’s a lot of people that will dangle carrots— money, opportunity, positions, whatever it may be— and there are some people that get really excited about that because it’s never happened to them before. But it’s happened to me so much and I’ve also gotten burned from it. Some of the most wealthiest people have burned me the most because they know how to talk, they know how to get what they want, and they know how to dangle the carrot and lead you on, right? So I think it’s if you want to have success in anything that you do, you have to be willing to do the boring work and you have to trust yourself and you have to build up that confidence. That’s like a muscle that you have to exercise.

Meghan Escobar (11:36)
Yeah. And it’s something that— another thing— another statement you made is fail forward, right? To know that no matter what you do, you— you ha— you have to fail.

Dana Flanagan (11:47)
Right. And it leads— it always leads somewhere. Like I always say, rejection is God’s protection and it’s redirecting you somewhere else. So when something happens… and I— I mean, just for real, a regular real estate agent, we’ve all had deals fall apart where you think you’re getting that sale, or maybe you’re banking on that commission and then it falls apart and you’ve done so much work and now it’s, you know, it may not resurrect itself again, but we’ve all been through it, right? The next day you get a new listing or the next day you get a new client. And it just— you— it rolls off your back. And I mean, I can’t even honestly remember those deals, right, like from five, six, seven years ago. So, you know, if something new is going to present itself and you have to keep that door open for— and that goes with anything, really. I mean, you talk about anything in life, you talk about, you know, marriage after divorce and finding love again— it goes in the same— those are all in the same buckets of focusing on what could happen and coming in with an open, you know, an open heart and open and good energy around it, and it will attract that into your life. So I always try to look at it that way that, okay, wasn’t meant to be, and it’s connecting me to something else at this time. I’m not supposed to be doing that right now. So—

Meghan Escobar (12:51)
Right, that door closed for a reason, and so let’s open a new one and maybe three more after that. Great perspective. Now, every entrepreneur and operator that I’ve ever known has always had a moment where things got real. And so maybe that was a deal that had gone sideways or a deal where you got burned and you didn’t see it coming, or just a time that you had to pivot really fast. Do you mind, Dana, sharing one of those moments with us?

Dana Flanagan (12:56)
Exactly. Yeah. Yeah, it’s happened several times in multiple businesses that I have. And it’s where people have made promises of payment on success, right? And I was so used to that because real estate was what?— payment on success, right? You close the house, you go to the closing, you get paid at the closing. The difference is is I was always getting paid through a— a real estate brokerage, and so I didn’t question where my paycheck was going to come from. When you start going into business for yourself and people make promises to you, even if you have it in writing, and they just all of a sudden don’t pay you, or they’ve got, you know, something didn’t happen and there was a little loophole, you— you’re gonna learn real quickly. And these are to the tune of six-figures, you know, mistakes, where a lot of time was invested and a lot of work was done and a lot of connections were made. And I also feel like you have to be very— if you’re connected like I am, I have to be very eyes wide open because people will leverage me for my database and my connections. And so I— I have learned that like now to work with me… I have a— a strategic advisory firm where I leverage and connect people that’s separate from real estate, and I don’t work without a retainer up front for that. So—

Meghan Escobar (14:33)
And that comes from the experiences that you’ve gone through, right? Yeah.

Dana Flanagan (14:36)
Yeah, you know, in real estate, it’s different, obviously, because, you know, real estate is just— is is a world that we don’t operate that way. But for anything else that I do when it comes to my— my consulting— I do a lot of business consulting on the side— I don’t do anything on a promise, not even if it’s a contract, I don’t care because I’ve had those contracts. “Oh, my funding didn’t come in,” or, you know, “We— we said we’d pay you this way, but we’re not gonna—” It’s just there’s always a something, and I have learned the hard way. And so, you know, I am very crystal clear on details now. And to— I’m not gonna say almost to a fault, but I will pick something apart if it has to do with my income and if it has to do with other people’s income around that, like the scalability of the business. So, you know, is this feasible? Does this make sense? Is this clear to the customer, right? Or the— or the employees or the realtors or whoever we’re talking about, right? I mean, it’s gotta be— clarity is— is really truly power, right? So—

Meghan Escobar (16:19)
Yeah. Yeah. And— and putting your time and energy into something that is gonna be worth it at this point in the— or at this name in the game or whatever, right? And the— and these are the things I feel like people don’t talk about enough. We live in this highlight society, everything’s on social media, everybody’s flashing the— the success, but not the story behind it. And I truly believe that is what separates folks from here to dabble and, “I just wanna make a quick deal,” versus those who are in the game long term. And your experience sounds like it speaks for itself here.

Dana Flanagan (16:53)
Yeah, so true.

Meghan Escobar (16:54)
And so let me ask you this: where are you focused on solving or what are you focused on solving or scaling next? What is the next big goal for Dana Flanagan?

Dana Flanagan (17:06)
Yeah. So it’s really, you know, this— this real estate company that I’m— I’m growing and scaling, which has been so much fun. It’s a business that started as a family-owned business and I really like the leadership there and I really like the owners. And it’s been, you know, they— everything they say they’re gonna do, they do, and they’re unbelievably easy to work with. So that is, you know, a primary focus of mine. And I also, you know, I have my— my strategic positioning firm, which does a lot of PR, I do a lot of promo, things like that. So that’s always— you know, I have a team there, so that’s something that I don’t do every single facet of that— that piece of that. And and really helping agents and brokerages be able to just do— do real estate better in today’s world and and have— and have it be easier in the sense of there’s been so many changes with, you know, NAR and a lot of the rules on a state level, on a local level, on a national level. And it got to the point, at least for me, got to the point where it wasn’t fun anymore. And I was just really tired of it. I felt like I was on a hamster wheel that I couldn’t get off because I was making really good money, and I kept saying to myself, “There’s gotta be more. There’s just gotta be more. There’s gotta be something else I can do because I just don’t want to do this the rest of my life.” And so, you know, making that— making real estate fun for the broker-owners and for the realtors and giving them the tools to be really successful at what it is that they do, and allow them that opportunity and that time for them to be able to invest in their business instead of, you know, doing all the— the dirty work behind the scenes, right? So, so that’s really my goal right now is— is really, you know, always growth in the real estate industry. I have— it’s— it’s what I can talk to on so many different levels. And, you know, I’d like to think I’m pretty well respected in the industry. And so I’ve got a lot to say about it. I’ve been through a lot of different facets of it. You know, I’ve worked in commercial, I’ve worked in residential, I’ve built my own like business around it. And so, never wanted to be a broker-owner— that was not something that I wanted to do. But you know, I really like the leadership roles that I’ve been of the last few years that I’ve been in. So it’s exciting to me and it’s, you know, it’s— it’s long-term for me and it’s something that I spent years building. I mean, I started working in a real estate office with my aunt, who was a top producer at the time, when I was twelve. So I’ve been around a really long time. Yeah.

Meghan Escobar (19:37)
And that goes back to your “not afraid of change,” right? It’s like you said you was stuck on this hamster wheel. And I think a lot of people struggle with that because they’ve spent so much time and energy building their success through one stream or one avenue, and they feel like, “Well, if I jump ship now or switch my— my career or my title, you know, what does that mean for me?” And so, you know, I think your perspective on this might help a lot of people that are— are— are— are conflicted in transition.

Dana Flanagan (20:05)
Sure. Sure. I think, you know, having multiple streams of income obviously is very important— I’m a bit— very big advocate of that— but I think just having to plan, you know. I mean, are you gonna sell real estate until you’re 70 years old? Maybe you’re just gonna retire for all the business, that’s totally fine. Some people have, you know, are wealthy in other ways or they have a spouse that they don’t really need to work, and that’s totally fine. For me, this has always been a lifestyle for me, and I absolutely love it. Like, I work all the time and I love it. And so, but I have the type of life where if I want to go, you know, do something in the afternoon, I can. Do I? Very rarely, because I’m busy with what I’m doing. But you know, it— it gives me— it’s always given me that flexibility that is important to me. And— and I don’t see myself going anywhere anytime soon. I just love this business. So—

Meghan Escobar (20:57)
I love that for you. Not many people can say that about the career— the career choices that they’ve made, so that’s a— it’s an incredible thing to have. And I know a lot of our listeners are either very early on in their journey looking to get their feet wet in the real estate industry in one way, shape, or another, or though we have folks that are heavy in the game for a while and just looking on, you know, what’s the next level up? What can I do to add on to my business, to expand my business? And so I— I— I think that they would really benefit from hearing this. You know, when it comes to building relationships and growing your network, what— what’s made the biggest difference for you personally?

Dana Flanagan (21:35)
Being networked— get— getting networked. And and that’s gonna take some work, right? I mean, that— that means going on LinkedIn and actively growing your connections and connecting with the right people, having a conversation, getting on a Zoom with somebody that could open doors for you. I did that for a full year. I made sure I got on at least one Zoom a day with people from LinkedIn and just talked about what I did, asked them what they did, asked them what kind of value I could bring. And it’s— you can go and get a lot of followers, that’s not what I’m saying. I’m saying to act— actively let people know what you do and, “How can I bring value to you?” I never walk in with an elevator pitch of, “This is me and this is what I do.” I always ask them what they do. What are they looking for right now? What’s important to them? What are they looking to do? Are they looking to grow, scale, or, you know, are they looking for a— a new opportunity? And I let them— I always let them know how I could potentially provide value in that specific situation. So if you’re not networked and you expect opportunities to just come in your— fall on your lap, it probably won’t happen. And you need to— to get out there and get networked and let people know who you are, what you do, and how you help them.

Meghan Escobar (22:48)
I think that is probably one of the most powerful pieces of information that you could have shared on this show today. And I say that because I learned a few years ago from a very incredible mentor, no matter what business you’re in, networking is something you need to do, right? If you want to be successful, every business is a people business. Sure. But mostly in real estate, right? People typically want to know one thing: what can you do for them? Well, what’s in it for me? So, I— I think that was an incredible piece of information that you could have shared for our guests to hear, yeah. And you know, that’s something you just can’t fake. Relationships are everything in— in this space. And so with that being said, before we do wrap, if someone listening was like, “You know, I really want to connect with Dana, or potentially collaborate with her or learn more about her services and how she can help, you know, move our business to the next level,” what is the best way for someone to reach you?

Dana Flanagan (23:48)
It would be to send me an email, which is [email protected] and let me know how I can help you, what struggles you’re facing right now, if there’s any opportunities that you’re looking for, if you’re looking to scale your business. And that’s not just real estate— I also work with other businesses. I do a lot with capital. So if you’re in need of capital, I am a partner at a capital firm, so we can take a look at your project and see what we can do to help you. So just send me an email at [email protected]. And I’m on all the socials— just find me at my name, Dana Flanagan, and let me know what I can do to help. I’m— I love making new connections and whatever I can do to— to do some sort of collaboration, I will.

Meghan Escobar (24:30)
Perfect. Well, listen, I appreciate your time, your story, and more importantly, your perspective. We definitely need more people in this space who are doing things the right way and not just looking to make a quick dollar, but someone who’s make— looking to create long-term relationships for long-term business. So thank you again for being here, Dana. And for those of you who are tuning in, if you found any value here, please be sure to hit subscribe. We’ve got more conversations coming with entrepreneurs and operators, just like Dana Flanagan here, who are out here building real businesses in real time with real people. So we will see you on the next episode.