DGS 143: It Doesn’t Have to Be Crazy in Your Property Management Business

Does it feel like your property management business is crazy, overwhelming, or maybe too much? It doesn’t matter how big or small the property management business, it can be crazy or calm. It’s your choice to make.

Property management growth expert and founder/CEO of DoorGrow, Jason Hull talks about his goal to eliminate the crazy. Business owners need to be calm for their team to feel that sense of calm in the workplace.

You’ll Learn…

[02:41] Basecamp: CEO runs calm workplace by eliminating and reducing interruptions.

[04:03] Entrepreneurial Myth: Crazy work is a badge of honor, not a badge of failures.

[04:31] Adrenaline Addiction: Workplace doesn’t have to be crazy or stressful.

[05:20] Planning: Communication in business focused on high-paced growth is critical.

[06:15] Tactical vs. Strategic Leadership Role: Who has enough vision, clarity on goals?

[08:14] Don’t be involved in everything. Stay in your area of genius and offload the rest.

[10:08] Key Ingredient: Create synchronous communication system to write, think, post.

[11:24] Four Reasons: Build great team to get fulfillment, freedom, contribution, support.


“All this painful stuff that we go through as entrepreneurs is some sort of badge of honor. Really, it’s actually a badge of failures.”

“Good planning in business actually decreases communication that’s necessary. It increases the calm. It increases clarity.”

“The idea is you want to create systems in place that protect you and insulate you from immediate urgency that is unnecessary.”

“Create calm workplaces. It doesn’t have to be crazy at work. It can be calm. The business really should be fun.”


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Remote: Office Not Required by Jason Fried

It Doesn’t Have to be Crazy at Work by Jason Fried


Welcome, DoorGrow hackers, 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 your business and your life, and you are open to doing things a bit differently, then you are a DoorGrow hacker. DoorGrow hackers 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 gateway to real estate deals, relationships, and residual income.

At DoorGrow, we are on a mission to transform property management businesses and their owners. We want to transform the industry, eliminate the BS, build awareness, change perception, expand the market, and help the best property management entrepreneurs win. I’m your host, property management growth expert, Jason Hull, the founder and CEO of DoorGrow. Now, let’s get into the show.

In today’s episode, we’re going to be chatting a little bit about fun. I asked in my mastermind group today—we had a pretty good group turnout today—and I asked by show of hands, how many of you feel your business is crazy right now? You would categorize it as crazy, overwhelming, maybe too much, whatever. At least half the hands went up, which I can’t say I’m surprised, but my goal is to get people out of crazy.

One of the things I wanted to talk about today—what I chatted about with them—is eliminating crazy in the business. One of the things to realize is that it doesn’t matter how big the business is, it doesn’t matter how small the business is. Your business can be crazy or it can be calm, and this really is just a choice. Is it possible to have a calm business even if it’s really large? For your experience as a business owner to be calm in the business and for your team to feel that sense of calm from you and it to be a calm workplace, yes it is.

I had a business once upon a time. Same business but it used to feel a bit crazy. I hung out with the CEO of Basecamp, Jason Fried. I won’t go into how we got on a call, but basically we were in some sort of chat. I was watching some live stream and I made some comments. He said he wanted to do a call with me, so we did a call together and I hung out with him.

This guy is what I perceived as a high-functioning CEO of a multimillion dollar company. He’s written books on remote teams. He’s got a book called Remote Work, virtual teams, software, and running companies. He hung out with me for probably about 90 minutes. He just showed me how he ran his business, how he basically ran a calm workplace, and how it was quiet. It shifted my perspective so dramatically. The biggest perspective shift I had was eliminating and reducing interruptions.

Years later, he came out with a book kind of recent. His book is called, It Doesn’t Have to be Crazy at Work. For those watching the video you can see this here, It Doesn’t Have to be Crazy at Work. It’s got this on the cover. It’s got crossed out 80-hour work weeks, packed schedule, super busy, endless meetings, overflowing inbox, unrealistic deadlines, can’t sleep, Sunday afternoon emails, no time to think, stuck in the office, all-nighters, and chat blowing up.

There’s this entrepreneurial sort of myth that it’s the hustle, the grind, hard work, tenaciousness, tenacity, and all this painful stuff that we go through as entrepreneurs is some sort of badge of honor. Really, it’s actually a badge of failures. It’s really what that is. It’s showing that you are creating a stressful environment for your team, and you’re running a stressful workplace. You probably—if you’re honest—are addicted like a lot of entrepreneurs to the adrenaline and the stress.

Our body gets accustomed to things we crave and want more of whatever emotion we tend to feel a lot. We get better and better at craving it and feeling it. Our brain actually wires differently over time to experience more of that chemical reaction of whatever emotion that we’re experiencing, whether it’s anger, fear, stress, or whatever. It Doesn’t Have to be Crazy at Work. This is a really great book. He came out later talking about some of the stuff that he taught me on that call.

Now, I don’t agree with everything in this book. The one thing I really don’t agree with is eliminating meetings and what he talks about not having planning or something like that. I believe that having really good planning in business actually decreases communication that’s necessary. It increases the calm. It increases clarity. Planning, I believe, is critical in a business, especially one that’s focused on high-paced growth, has a lot of moving parts, and communication is really important. It actually significantly decreases your communication.

If you have an annual planning meeting, quarterly planning meeting, a monthly planning meeting where you’re breaking down these things into smaller and smaller bite-sized chunks, weekly planning meeting, or maybe a 15-minute daily huddle, these are the things we talked about in DoorGrow OS. If these things, the ultimate operating system for a business, especially for a property management business, if you have these meetings, you can run your entire company in a small number of hours a year. That’s all you have to do.

Anything outside of that, you are really stepping into more of a tactical role overall or you’re being more like an employee in the business and doing work. But in a strategic position of leadership, if you have a really good executive team, that’s all the time you would really need to be involved in. You may not even have to do that if you have really good executive team members to run things for you, and they have enough vision and clarity on the goals. They can move this business forward.

A lot of times, we have a lot of ego as entrepreneurs. We think it’s all up to me. Everybody else isn’t as smart as me and my team members need me to tell them what to do and to guide them. I’m so brilliant. We don’t really know because we don’t really involve them in the planning and communication process.

I want to point out that business should be fun, and it should be calm. One of my mentors that I’m working with currently that’s a coach of mine, he talks about work being boring. He talks about how, when you have a multimillion dollar business and your business is scaling, you then eventually get to a state where you no longer have any major trauma or major glaring problems. You’re insulated from these things if you built your team and systems the right way. Now you’re just doing the boring work and you need to be willing to do the boring work.

His wife who really runs their company and his brilliant and brilliant operator also talks about how if you’re doing the boring work and the business gets boring, that’s a good sign that you’re doing things right. Then it’s time to just maybe get a hobby. What most business owners do is they make the mistake and go start something new, or create more drama, either in their personal life. Sometimes they’re cheating on a spouse or they’re starting a company, or they’re burning their existing company to the ground. They create some more drama.

One of the things that we have to do is wean ourselves off the addictiveness of having to be so involved in everything, having to have so much connection to everything, thinking that we’re so important in the business, and to be willing to allow calm to happen. It doesn’t matter if you’re just a small company with a small number of doors and you have one assistant. Your business could be calm.

Or you could have a really large team and tons and tons of doors, and your business still could be calm. If you have the support at the level that you need, you have the systems that you need, and you allow yourself to be protected from the things that create crazy, you really are able to stay in your lane and in your area of genius and offload the rest.

I do recommend this book. It’s a really good book. It Doesn’t Have to be Crazy at Work. It just is kind of a manifesto for the future of business. Businesses are often connected to analogies of war in competition and fighting, and these massively stressful situations, but calm companies are very efficient companies. They’re companies in which people are able to get in the flow work state. They’re able to be calm, things get really quiet.

My business is very calm now. It’s very calm, especially for me. It’s very calm. It’s very quiet. We don’t have a lot of communication that has to happen among our team. Most of our team members are in the flow of doing what they love to do each day. There are little things that pop up here and there but we tackle them maybe in our 15-minute morning huddle. Usually I just ask where they are stuck. Those things all get dealt with then and there might be a little bit of communication in our messaging app that we use each day. We don’t have situations, in general, that are immediate or that are urgent.

One of the key ingredients is to create a synchronous communication system in the business, which means people can write stuff out, think about it, and post it for the rest of the team to look at later. We can send a voice message to a team member or multiple team members for them to listen to later. Unless something’s immediate and urgent, we don’t call the team member. We don’t walk into their office. We’re virtual, so we can’t do that. The idea is you want to create systems in place that protect you and insulate you from immediate urgency that is unnecessary.

As a business owner, you really want to get to the place where you don’t have immediacy and urgency ever bombarding you, attacking you, or disrupting your day. You should be insulated from emergency maintenance requests at three in the morning. You should be insulated and protected from an angry or upset owner as the first round. Maybe you deal with those things after somebody else but your goal eventually is to be the owner of the business, not the property manager.

Anyway, I hope this is helpful. Create calm workplaces. It doesn’t have to be crazy at work. It can be calm. The business really should be fun. Like I talked about in one of my previous episodes, four reasons. You want to get more fulfillment, more freedom, more contribution, and more support in your business. You need to build a really good team.

It’s a lot easier to get to the place of having a calm workplace in a property management business once you’re in that category where you can afford to have a team, and that’s usually in the 200–400 door range. Usually at that stage, you’ll see business owners by then they have a team. If you do this correctly, this can be one of the calmest stages ever in your entire business. Most do not do this correctly.

I call this the second sand trap because they built their business the opposite way. They built the business around the wrong person because they are the wrong person, which means they’re showing up doing the wrong things in the business. They are spending their time doing things that really are not their greatest strength or their greatest area of genius, or give them the greatest peace and calm, or the most fulfillment, freedom, joy, contribution, and support in their day to day. So they’re building the wrong team around the wrong role, the wrong person, building a support system and mechanism around the wrong center, sort of the nucleus of this business, which is yourself.

They have a false perception of you that is overwhelmed, overworked, stressed, and doing the wrong things, then you’re building a team to work with that person. You then have the wrong team which adds more stress, anxiety, and challenge to you. You have the wrong business that’s built around them. It all starts with you getting really strong clarity in yourself, which I’m really good at helping clients get clarity on, focus on themselves, and figure out what really brings them the most joy or stresses them out, which things are they doing that are tactical versus strategic, or which things are energetic plus signs versus minus signs.

If that is a challenge for you, and you feel like your business is crazy. Maybe you’re getting enough doors, maybe you’re not. We can help you but maybe you’re getting enough doors. Maybe your business feels crazy, and your team feels stressed and crazy. You feel stressed and crazy, and you’re not having fun. You’re not enjoying your day to day. That’s a strong clue that you’re out of alignment with those four reasons. You’re doing the wrong things. You probably could use an objective perspective and get some support.

If that is the case, we will be glad to help you over at DoorGrow. Reach out to us. You can check us out at doorgrow.com. If you feel like it’s crazy at work, maybe you need to be honest and recognize there’s a part of you that enjoys that. There’s a part of us that tends to like the drama and the challenges that we deal with. If the majority of you don’t, you don’t have to live with it.

I’ve seen businesses dramatically change in a very short period of time. Even in a single quarter, we can have you in a very different role, very different position, way less stress. The right team members, we can reassess your team or redeploy your team in different positions. We can get you your first assistant or whatever. We can help you get into that state to where you are in a place of calm. Just remember, it doesn’t have to be crazy to work.

Hopefully that’s beneficial to everybody. I’m Jason Hull, and until next time, to our mutual growth. Bye, everyone.

About 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.