DGS 240: Wearing too Many Hats in Property Management

wearing too many hats in property management artworkProperty management entrepreneurs… how many hats are you currently wearing? It’s easy for business owners to get stuck doing things they don’t actually enjoy doing.

Property management growth experts Jason and Sarah Hull talk about how to get out of the roles you don’t enjoy and into the roles you do. Learn how to stop wearing too many hats in property management, once and for all.

You’ll Learn

[03:17] The myth of wanting to clone yourself

[07:51] The pros of a great hiring system

[13:46] Which hat do you take off first?

[17:58] Next steps


“That you need 10 people to clone yourself as an entrepreneur.”

“A generalist that’s good at everything is never the best.”

“For every role that exists, there’s always a person to fill it who actually really love doing that role.”

“If you have office politics, you’ve got a culture problem.”


DoorGrow and Scale Mastermind

DoorGrow Academy

DoorGrow on YouTube



TalkRoute Referral Link


[00:00:00] Sarah: For every role that exists, there’s always a person to fill it who actually really love doing that role.

[00:00:09] Jason: Welcome DoorGrowers, to the DoorGrowShow. If you are a property management entrepreneur that wants to add doors, make a difference, increase revenue, help others, impact lives, and you are interested in growing in business and life, and you’re open to doing things a bit differently, then you are a DoorGrower. DoorGrower property managers love the opportunities, daily variety, unique challenges, and freedom that property management brings. Many in real estate think you’re crazy for doing it. You think they’re crazy for not because you realize that property management is the ultimate, high trust gateway to real estate deals, relationships, and residual income. At DoorGrow, we are on a mission to transform property management business owners and their businesses. We want to transform the industry, eliminate the BS, build awareness, change perception, expand the market, and help the best property management entrepreneurs win. We’re your hosts, property management growth experts, Jason Hull and Sarah Hull, the owners of DoorGrow.

[00:01:03] Now let’s get into the show. All right, so we released a funny video. So if you have not seen any of our funny videos, we put out quite a few of these. We have a whole playlist of them on YouTube. You can go to youtube.com/doorgrow and go to our playlist and look for our playlist of funny videos. Our newest funny video that we released is all about hats.

[00:01:28] It’s got a whole bunch of hats and it’s silly, and I’m putting on different hats, and so if you want to laugh at me. Go check that out. we thought we would talk about this idea today. So what’s the idea?

[00:01:40] Sarah: So the idea is are you wearing too many hats, aka are you filling too many roles in your property management business?

[00:01:50] Jason: All right, so when you first start out, you have to wear every hat, right?

[00:01:55] You do everything in the business because it’s all on you. You’re like, “Oh, let me send that over to my maintenance coordinator… who’s me. And let me get that over to my bookkeeper… who is also me. And Oh, my receptionist will answer my calls for me today because that’s me.” What are some of the hats that property managers are wearing.

[00:02:15] Sarah: There’s so many of them. Let’s see. There’s maintenance coordinator, a leasing agent, there’s usually the bookkeeper, whoever’s going to handle finances, there’s of course the CEO who’s going to set the vision of the company, there’s the operator who’s going to do things on the backend, there’s the salesperson or the BDM, there’s usually like a property manager, there’s sometimes assistant property managers… As companies grow, they sometimes get tenant coordinators or client coordinators like just to handle like tenant or client communications. But when you start out, like all of this is usually you.

[00:02:55] Jason: One of the things that I hear a lot from early stage entrepreneurs, people that are just getting started is they’re like, “I just need to clone myself. I just need to find somebody else. Just like me.” And so this is the big mistake that everybody makes initially in hiring. It’s everybody does it like we all go and try and find somebody like ourselves.

[00:03:15] That’s what we think hiring is. We think hiring is cloning ourselves. The challenge with that is that the clone myth, as I call it, the reality is that you need 10 people to clone yourself as an entrepreneur. You need a different person for each hat.

[00:03:32] Because if you find somebody that is as adaptable as you and that can do everything like you and is driven like you, guess what they’re going to do? They’re going to do what you did and they’re going to leave and go start their own company. I’ve seen this over and over again where people hire a clone and the clone does exactly what a clone would do. They become like you and they leave and sometimes take your clients and start their own business and become your competition. And so we don’t want to fall prey to the clone myth. We want to find specialists that we can give pieces of what we do or hats to that are really good at that particular hat and a generalist that’s good at everything is never the best.

[00:04:17] You are not the best at every role. You probably think, “nobody else could do it as good as me.” This is the other belief that early stage entrepreneurs say. “Nobody else can do it as well as me. I might as well do it myself.” And that’s a trap. It’s a trap that keeps you doing everything forever. And if you believe that, then that means you will by default be comfortable getting crappy team members that are worse than you at these hats.

[00:04:42] Because if you believe that you’re the best and nobody else could be better than you, then you will go hire people and you will tolerate people that are worse than you at these particular roles. And then you’ll be frustrated and I have a team of people that are better at their particular roles than I would be and this gives me a lot of confidence being able to let go of stuff. Like Sarah is way better at the details way better operations way better at putting things together. Like you’ve significantly improved the business and she’s better at all of those things than I am and there’s things that I’m better at than Sarah, but that allows me to stay in those areas I get to stay in those areas where I am better at those things than Sarah and then we have different team members Adam, and Mar, and they’re all better at their particular tasks than I would be.

[00:05:31] Sarah: Or I would be. Yeah.

[00:05:33] Absolutely. And that’s what you want, is you want someone who is better at whatever this is than you are, especially if you don’t enjoy it. So if you’ve got things in your business that you’re holding on to and you think, “oh, I’ll just never find somebody who loves maintenance coordination. Like who on the world would love to do that job because it’s horrible?” Somebody will love it.

[00:05:59] Somebody who likes details and organization and they like having a plan and a structure and a system. There are people who function that way and they really enjoy that. And it’s so funny because Jason was like, “for every role that exists, there’s always a person to fill it who actually really love doing that role.” And it’s true. It’s really true.

[00:06:22] Jason: That’s a good point because early stage entrepreneurs also believe that because they hate doing something like if you hate maintenance coordination, you’re like, “man, if I never have to do another maintenance escalation or talk to a tenant again, I’d be so happy.”

[00:06:37] A lot of times entrepreneurs believe that means nobody else would like it either. It’s really a self centered, self centric view to believe that the rest of the world are like you. They’re not. Like one of my mentors would say, there are people out there that like changing bedpans, you know?

[00:06:52] And I’ve said that to some people that were nurses or something like that. And they’re like, “yeah, I do. I feel like I’m helping them.”

[00:06:58] And I’m like, “that’s great. I wouldn’t want to do that.

[00:07:00] Sarah: Like Evelyn, she says, “I don’t like the changing of the bedpans, but I do like that when I do that, I know that I’m helping somebody who can’t do it for themselves.”

[00:07:07] Jason: Yeah. And so she’s happy to do it.

[00:07:10] Sarah: You can’t pay me enough money in this world to change a bedpan.

[00:07:13] Jason: There is not enough money in this entire universe. That’s my sister in law. And yeah that’s wild. And so I want everyone listening to believe that there are people out there that can do the things that are your minus signs.

[00:07:26] You can find people that’s their plus signs and they will do it better than you. If you believe there are people out there that can do it better than you, there’s a lot of dinosaur bosses. This is how you know you’re a dinosaur boss. If you’re the person that just believes everybody in the younger generation is terrible and there’s no good hires out there available and nobody wants to work, then guess what you’re going to find and attract when you go onto your job search?

[00:07:51] There are great people out there. And if you build a really good hiring process, you can find and attract them. But the great people don’t want to work for a dinosaur boss, like somebody that just believes that ‘if I pay you, you should just do it and you should just like it and just suck it up.’

[00:08:06] Because that’s not very inspiring and people have options nowadays. They don’t have to stay at a job very long. They can go work elsewhere. And the way that we retain team members is we create a culture of people that all share the same vision, same mission to transform property management, business owners.

[00:08:23] And because we hire specialists and hire people that are really dialed in personality wise for that particular role that we know they can be great at it. And because each of our team members are great, it creates this sense of mutual respect on the team. Everybody on our team likes each other. Yeah. And they respect each other.

[00:08:42] And in our daily huddles, they’re like celebrating each other and sharing, like pointing out how awesome different team members were because they can see that these team members are really good at the things they do and it’s things they’re not good at or wouldn’t want to have to do.

[00:08:57] Sarah: Morgan just said, I think, when she came back from leave, I was catching up with her. And then she was on some coaching calls with clients and she shared part of it with me. And I just had this conversation with one of our clients, and she said, “everybody on our team. I love them. Like I really like these people. I work with them every day, but I really enjoy working with them.” And she said, “if anybody on the team came to me with any task and said, ‘Hey, like I could really use your help on this.'” She says, “I would do it in a heartbeat. I wouldn’t even flinch. I would do it in a heartbeat and I would want to do it because I care about these people and I want to help them.”

[00:09:34] Jason: And that’s because we’ve created a culture initially entirely around what I want. Like I as the visionary gets to set the culture of the company and I created values and everything.

[00:09:47] Now, when Sarah became an owner, we took a fresh look at them. And we revisit them and then I don’t think we really changed much.

[00:09:55] Sarah: No, we didn’t. I gave her an opportunity to have input, but…

[00:09:59] would you, if I wasn’t a value match, would you have brought me into the company? You wouldn’t have hired me, but nevermind ownership of the company. You don’t give ownership of a company to somebody that’s like not a culture.

[00:10:10] Jason: If you weren’t a value match, we probably wouldn’t be married. And so this is the thing. There’s a lot of couples in property management. I’ve noticed we get a lot of couple clients, husband and wife teams.

[00:10:21] And it’s very typical that the husband is more visionary, sales, wild, cowboy, entrepreneur and that the wife is like stable, crusher of all hopes and dreams, just kidding, grounded, practical, make sure everything works operator personality type. Yeah.

[00:10:38] Sarah: Sometimes we do see, they’re like, “we’re going to do this crazy big thing!”

[00:10:41] And operators were like, “we can’t afford that. Cool, but that sounds really insane. So what can we actually do and how can we actually make it happen?” So like we are the ones who make sure that things happen instead of just,

[00:10:57] Jason: yeah.

[00:10:57] Sarah: We’re not the crusher of the dreams.

[00:10:58] We’re the dream makers.

[00:11:00] Jason: They’re the dream. Yeah. They bring it into reality. The “maker-happeners”. ,

[00:11:04] That’s good. That’s really good.

[00:11:05] Sarah: It’s so good. Madi’s going to laugh so hard when she’s editing this. She’s going to go, “that’s not a word.”

[00:11:10] Jason: Maker-happeners.

[00:11:11] Sarah: The word now, Madi.

[00:11:13] Jason: This is my Maker-happener.

[00:11:15] And yeah, we’ve got this mutual respect that exists on the team, and if you don’t like your team, be honest. If your team increases your pressure and noise, if they stress you out, if you are frustrated at your team members, you have the wrong team and it’s your fault. You created it, you allowed it, and you kept these people because you probably thought that’s just how business works or that’s what’s available.

[00:11:40] Sarah: Even if you’re like, “Oh no, I like everybody,” but does everybody like everybody else? Because if your team doesn’t like each other, how quick do you think they’re going to be to really jump in and help the other one? Because everybody needs help at some point.

[00:11:52] Like deadlines come and things happen or whatever. Like summer happens and we’re like, “Oh my God! I thought like I had more time on this and all these leases are due. Can somebody help me?” There is going to be a point in which someone on your team needs help from somebody else that doesn’t usually do that thing.

[00:12:07] And if they don’t like each other, they’re not going to help each other. They’re going to go, “Oh yeah, look at Susie. She can’t even do her own job.”

[00:12:14] Jason: Yeah. If you have office politics, you’ve got a culture problem. If you’ve got you may have team members that secretly don’t even like you and you may not know it, but you can tell. You can feel it.

[00:12:25] Most employees probably here in the U. S., that standard American employee doesn’t really like their job. They just want safety and certainty. They want stability. They’re not there because it’s giving them a sense of fulfillment, freedom, contribution, support. It’s like the best thing and they love it.

[00:12:41] So that means they’re B players. A players are what we have on our team at DoorGrow. B players are what one of my mentors called hiders. Their secret goal if they were really honest would be to do as little work as possible, get paid as much as possible, and then they go and complain about you and live for the weekend.

[00:13:02] And so if they love the weekend way more than they love their day-to-day, there’s probably a problem. Like you want team members that are like, “man, I’m really excited. I love getting to do what I get to do.” If I didn’t have the role that I have or get to do what I get to do, I would feel probably lost, depressed, and bored out of my mind.

[00:13:23] I love getting to do what I get to do. And my guess is that most of the people on my team would probably feel that same way. If they just had nothing to do. So I don’t know, maybe there’s some that would love to just not work ever a day in their life. I don’t know. But for me, that would be crazy.

[00:13:39] Sarah: Not anymore.

[00:13:40] Jason: So what else can we talk about related to getting rid of these hats? Because in the beginning they’re wearing every hat. How did they decide which had to get off first?

[00:13:49] Sarah: What are the things that you like? Because those are the things you should keep.

[00:13:54] And not just “Oh, that’s annoying,” or like “it’s okay, but I don’t love it.” The things that you really don’t like, the things where, like for me it was talking to tenants, that was what it was for me, and sales. I hated sales. I hated doing sales. I was really good at it, but I just, I hated it. Look at, the things that you do and the things that you like, you tend to get them done pretty quickly. Yeah, if you like going through emails. You’re going to do that and there’s going to be very little friction there.

[00:14:23] No one’s going to have to say “Oh, did you check your email?” But if you hate going through emails and you’re like, “oh my god. Like why is email even a thing? I don’t even know why we have to do this,” You’re going to procrastinate. Yeah. It’s going to build up and you’re probably not the right person to be doing it.

[00:14:41] Jason: Yeah. If there’s anything that’s been on your to do list for more than a month, it’s probably because you are not the person that should be doing it. That’s a pretty big clue. One of the big mistakes I see people make when getting their initial hire is they try and find team members to wear multiple hats.

[00:14:57] They’re like, “I’m going to get an appointment setter slash assistant.”

[00:15:02] Sarah: My favorite is, “my operator is also going to do sales for me.”

[00:15:05] Jason: Oh yeah.

[00:15:06] Sarah: No, they’re not.

[00:15:08] Jason: And why that’s a problem is these are opposite personality types. If we’re picking people that are two different personality types. If we’re giving them a role that’s two different personality types, then we are setting them up for some sort of failure.

[00:15:21] And they’re not going to really do well at the one that is not their personality type. And so we need to make sure we’re not throwing multiple hats onto a person. We’re trying to offload multiple hats that are different personality types. It’s not going to work. We need specialists that are the right personality for the role.

[00:15:39] So at DoorGrow, we are experts on matching the right personality types, knowing the personality types that you need for particular roles. There’s a certain personality type for a BDM, for an operator, for a receptionist, for maintenance coordinator, property manager, leasing agent.

[00:15:54] There’s certain personality types that are good at these. And if you hire based on skill, you will miss the personality. And so hiring based on personality and based on culture are more important for the team and for the role. So usually the first person that we recommend in our DoorGrow code that most entrepreneurs get initially to get the most leverage would be an assistant.

[00:16:19] Like maybe around 50 units, you should have your own assistant. But we’ve got clients that come to us with hundreds of doors and they still don’t even have an assistant for themselves. They just keep hiring to take care of the business while not taking care of themselves. So they’re not really taking hats off or giving up stuff.

[00:16:35] They’re just helping the business out. And so they end up more and more stressed the bigger the team gets. So a big piece of this is you need to make sure that you are taking care of yourself and the way we help our clients get clarity on themselves in clarity on what are their minus signs versus their plus signs, what they, what drains them versus what gives them energy is by doing a time study.

[00:16:57] And this gives them a lot of clarity on how do I get to the next level? How do I offload the negative things so that I can spend more time in my area of genius and wearing the hats that I want to wear? And then we build out job descriptions and et cetera. So we have this whole process for taking entrepreneurs through to give them a lot of clarity.

[00:17:14] Then later. Maybe around 200 plus the most important hire that you will ever make in the business will be to get an operator. If your spouse is already an operator, then you already have the most important person that you will ever bring into the business on your team, which is amazing and awesome. This person needs to be very intelligent.

[00:17:34] They need to be sharp. They need to be driven to getting systems and processes dialed in. They want to see the business succeed. They handle all the details. They make everything work and they make sure that the team makes everything work. And this allows you to spend more time in the visionary role or in the sales role or whatever it is as a visionary entrepreneur that you really enjoy.

[00:17:55] All right. Anything else related to hats?

[00:17:58] Sarah: So I think if you’re listening to this and you’re going, “yeah, but I’m still doing all this stuff and I would like to offload that, but I don’t think I have the money to offload that,” because this is what we hear next is, “yeah, that would be great, but I can’t afford it. I can’t afford to hire, two or three or eight people.”

[00:18:18] Jason: So we have processes for this, but we have to back you out of the corner. You’ve painted yourself into, so first we do need to get you clarity on what you do enjoy and what would make you more money because it doesn’t make sense to go get somebody if you could create more leverage, right? And so sometimes it’s about creating more leverage related to time right now. So we have processes for helping you get even more done. Like one of my clients did a time study and recently and said that he had found that he was spending an hour after three o’clock, he was spending an hour to get things done that took him 10 minutes in the morning.

[00:18:56] And so part of it is just clarity on your circadian rhythm, your time, like your energy, whether you’re getting good enough sleep. So we worked on some hacks to increase his brain’s bandwidth so that he could do more later in the day and get a lot more done. This may triple the output of what he can accomplish.

[00:19:15] Then we have processes like daily planning time studies. We have these different things that help you get more yield from your day. We have a training called the priorities training. It talks about how Sarah was able to run her business with over 60 percent profit margin with only one part time person up to 260 units.

[00:19:34] Which is crazy. They add units too.

[00:19:36] Yeah. C class properties. Yeah. In a rough area. Yeah. And she was able to reduce a lot of the communication, a lot of the friction and systematize the business so that it could run very efficiently. And so we train clients on how to do that. We get people come to us and they’re like, “I’m burnt out at 50 units.”

[00:19:55] Sometimes they’re like, “I’m stuck at a hundred units. Like I just can’t handle anymore.” And you can. There’s ways of making this easier.

[00:20:04] Sarah: But you can’t give nothing changes, right? So if everything stays the same, you’re right. You can’t, but you need to make some changes probably to yourself and in your business.

[00:20:15] And then all of a sudden it will allow more space and you’ll be able to add on more units.

[00:20:21] Jason: This is where good coaching comes in is we can help you get more yield from your day, create more bandwidth so that you can spend more time growing the business. We give you the strategies to grow. You make more money.

[00:20:32] So a lot of times clients come to us in that scenario. I’m like, “let’s create some space and then let’s get you focusing on revenue generating stuff. Let’s get you making a lot more money. And then let’s make sure we hire what you actually need most. So you can spend more time making more money because then you’re making smart, strategic moves when you hire. Instead of just hiring what the business needs, which can be really expensive if you make mistakes. And if you get any bad hires, we have a really great hiring system called DoorGrow hiring. One bad hire is going to cost you minimum 10 grand because you’re going to spend probably at least three months on them of pay, there’s a certain amount of money they’re going to cost you and you’re going to lose out on because they weren’t generating revenue or helping to keep revenue. So there’s a lot like bad hires are one of the most expensive and costly things you can do and it eats up your time, which is the most valuable resource in the business.

[00:21:24] When you’re onboarding and training somebody that’s never going to be good at it. And so we can help with that as well, helping you get really good team members and collapse time on hiring. We’ve helped companies replace entire teams, cut their staffing costs in half like overnight, she does this stuff and and build out really good hiring systems and processes so that you can get people quickly and scale quickly as you’re adding doors.

[00:21:49] We have the stuff to help with all of that.

[00:21:51] Sarah: We do. Cool. If you’re hearing this and you’re like, “man, that would be really nice, then you should reach out. Contact us. Get on a call. Go to doorgrow.Com. You can see what we’re all about, what we do. You can book a call. If you’re like, “hey, this is for me and I’m ready to go right now,” cool.

[00:22:06] Sign up. Join our mastermind and you’ll have some awesome coaches to support you.

[00:22:10] Jason: Yeah. Some of you listening are feeling really stressed out. Every business owner has been there. Some of you listening have felt really stuck.

[00:22:19] It’s just things aren’t moving forward. You can’t figure out why the marketing stuff isn’t working. You’re not really adding doors. You’re not getting ahead. You’re getting stressed. You’re getting burnt out. You probably cannot see yourself doing this for five more years. And you need to reach out for help.

[00:22:36] One of the most difficult things for entrepreneurs to do in especially early stage entrepreneurs is to humble ourselves. To be humble and to realize we could use some help and ask for help. We just we always think we can handle it all ourselves, like we’ve got it. “If I just watch enough youtube videos or try and get enough free stuff I can figure out.” Or “if I just work hard enough I can save a dollar and do it myself or if I read enough books…” and so our goal at DoorGrow is to help you collapse time and make a lot more money. You can probably figure it all out, and I’ve seen people work really hard at doing this, but it will probably take you a decade to figure it all out. Whereas we could probably help you figure it out in a small fraction of the time. We’ve done it over and over again. So if you’re feeling stuck or frustrated, reach out to us, let us help you make it make sense financially. We will help you justify the financial expense of working with us because really, a good coaching program should be making you money, not costing you money.

[00:23:40] And if you do what we tell you to do, you will be making more money. Our program pays for itself. This is why we have probably the lowest churn rate in the entire industry. We keep clients because they’re winning.

[00:23:52] So reach out to us at DoorGrow. We would love to help you get going.

[00:23:55] Sarah: Be open, just be open to do things a little differently.

[00:23:59] And if that’s the case, if you are interested at all in having your company and your business and your life, just be better and different than this might be for you.

[00:24:11] Jason: The slowest path to growth is to do it all yourself or to think you can do it all yourself. That is it for today. So until next time to our mutual growth. Make sure you join our facebook group at doorgrowclub.Com. We have a bunch of free stuff in there and reach out to us at DoorGrow at doorgrow.Com We would love to help you grow your business. Bye everyone

[00:24:30] you just listened to the #DoorGrowShow. We are building a community of the savviest property management entrepreneurs on the planet in the DoorGrowClub. Join your fellow DoorGrow Hackers at doorgrowclub.com. Listen, everyone is doing the same stuff. SEO, PPC, pay-per-lead content, social direct mail, and they still struggle to grow!

[00:24:57] At DoorGrow, we solve your biggest challenge: getting deals and growing your business. Find out more at doorgrow.com. Find any show notes or links from today’s episode on our blog doorgrow.com, and to get notified of future events and news subscribe to our newsletter at doorgrow.com/subscribe. Until next time, take what you learn and start DoorGrow Hacking your business and your life.

Enjoyed this episode on wearing too many hats in property management? Get equipped with more content like it by exploring past episodes of the #DoorGrowShow.

Jason Hull

Jason's mission is "to inspire others to love true principles." This means he enjoys digging up gold nuggets of wisdom & sharing them with property managers to help them improve their business. He founded OpenPotion, DoorGrow, & GatherKudos.

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