Can You Run a Successful Vacation Rental Company Without Completely Sacrificing Your Personal Life?

This post is designed to inspire Property Managers everywhere to run best-in-class, functional and profitable businesses, while staying healthy, happy, and free. And we think it's more salient today than ever before.

The biggest lessons from 3 years of explosive growth.

“What series of really terrible decisions did I make to end up here?”

That was the thought running its paces through my head on January 10th, 2015 at 11:30pm.

I was in the basement level of a cabin we managed cleaning up sewage that had backed up in to the house. I knew if I called a service it would be thousands of dollars – we had just signed the client weeks before – there was no way the owner was going to pay for that.

So, I moved the guests to another home, rolled up my sleeves, and got busy – it’s my business so I knew I had to do what I had to do to take care of the issue at hand. If I’m honest though, something about picking wet, used toilet tissue out of the base boards with a toothbrush had me missing the corporate days when I was still a high-level tech consultant at a billion-dollar business.

So how DID I wind up there you may wonder?

The Backstory​

Like nearly every property manager or vacation rental owner I’ve met and spoken with, we all seem to share a common backstory: Having a career completely unrelated to vacation rentals and then through a seemingly random set of events finding yourself either managing properties for others or for yourself.

That was certainly true for me.

An aspiring tech nerd since adolescence, through a set of providential & nearly impossible series of events I broke in to high-level consulting at the wee age of 22 and was on a rocket ship trajectory. But unfortunately, as much as I loved tech and computer science, I learned all too quickly that Corporate life just wasn’t for me.

For me, Corporate life became a place where a lot of dreams went to die in servitude to the “golden handcuffs.” I vividly remember bemoaning the meetings, listening to incompetent employees explain why something “couldn’t be done” (only to go do it myself), having people in leadership reject my ideas because “that’s not what we hired you for,” and ultimately realizing that I was a part of an environment where entrepreneurship and ingenuity weren’t attributes that were typically valued.

I wanted to build something and take control of my own destiny, push myself, take risks, feel what it really felt like to put it all on the line and see what happens.

So after five years (that I’m ultimately thankful for) I left it all behind to start a property management company in east Tennessee under the name, ‘’.

I would have never guessed when I took that step out of my comfort zone that I would embark on one of the hardest, stressful, and most rewarding business ventures of my life up to this point.

The Life of a Property Manager​

Our growth was explosive. We more than doubled in size every year we were in business until we were acquired last December.

On paper that sounds great, of course. Revenue is doubling, site traffic is doubling, economies of scale are starting to play in your favor more and more everyday – but there’s something else that grows exponentially as well when you’re growing a property management business: Operational Headaches.


The first 1.5 years it was just my business partner David and I answering the calls – around the clock – about everything from true issues to people wanting WiFi passwords at 1:30AM. As husbands and fathers there was no quality of life. No planning date nights with our wives, no dinners out. No planning time with the kids without knowing there was a high-likelihood of an “emergency” ringing our phone and pulling us away from our families.

The faster our business grew, the faster our quality of life took a nose-dive. My marriage was taking a hit. My kids weren’t getting to see me; I remember so little of my kids early years.

Something had to change – we knew this wasn’t sustainable.

So, David and I got busy figuring out how to grow the business without sacrificing our families and personal lives more than absolutely necessary as well as reversing some of the pain our personal lives were experiencing.

After that point life started getting better. We were able to start taking planned days off (without our phones!). Planning small trips with our families to get away for a few days. Put barriers in place between us and abusive guests. It got doable again – but still stressful.

While we definitely failed in a lot of ways in the process, we think we also stumbled upon a lot of truths that helped us find a more maintainable quality of life while running a fast growing property management company. I’d like to share some of those takeaways with you in hopes it can help you find a better work/life balance too.

1. You don’t have to give customers constant support around the clock to run a great business.

When we were first growing, we had a phone number that current guests or booked guests could call with issues, questions, etc. That number went in to a queue that would ring our phones while the guest heard ‘hold music’ until one of us answered.

That happened 24/7. Yes, most of the 1AM calls were for stupid stuff. Yes, it left us feeling unrested and exhausted on a consistent basis. Yes, we really believed we were providing “excellent customer service” that was a common expectation among travelers.

Eventually though, we wised up.

We implemented an affordable secretary service that billed on a ‘per call’ basis and had a set of procedures for the most common issues (locked out, wifi password, general directions, etc.). This was now the first line of defense. While there are services like CallRuby out there, we found by far the most affordable solution was to do some research and find a semi-local business that offers this – we averaged less than 0.20/call.

We also decided that after 8PM, if it wasn’t an emergency, we weren’t dealing with it until morning. We put this in our arrival packets to guests. If calls came in to the answering service, they sent us an email and we called them back in the morning.

We gave the answering service a set list of scenarios that were truly ‘emergencies’ – for those they could call and wake us up. Otherwise, please don’t call us.

Surprisingly, reviews stayed strongly positive. There was no detectable difference in review scores after pulling back afterhours phone support, but there WAS a detectable difference in mental health, drive, and restfulness. In hindsight, drawing these lines of customer support was crucial.

2. It is not your job to make your guests happy – that’s their job.

This one was super difficult to learn, but also super helpful.

As a property manager or vacation rental owner, it is absolutely our job to 100% make sure we are doing everything we can to create quality stays, vacations, and provide incredible customer service.

But it is 100% your guests job to decide whether they want to be happy or not.

"It's not your job to make your guests happy. That's their job." - Wes Melton

As property managers, it is not our job to make our guests happy – it is our job to provide excellent customer service in hopes that your guest will be reasonable and choose to be happy.

Many will cringe, disagree, or call me an idiot for this idea – but I firmly believe it is true.

By believing it is our job to not only provide excellent customer service, but to also make our guests happy (a nearly impossible feat for some guests!), we lose all objectivity about how much time/effort we are giving to your guests. This ultimately creates an environment where our decision-making process is hindered and we make poor decisions with our time, business resources, and will let it affect our personal life after hours by not having appropriate boundaries.

The big lessons we learned is to decide (write this stuff down in a set of rules) what levels of customer service we were going to offer in every typical scenario and then sticking to those offerings. That may mean that at 3am you’re not going to run a hair dryer to a guest who is livid that their home doesn’t have a hair dryer (even though it was advertised as not having a hair-dryer!).

It was tough – but we eventually started to force our guests to live inside the bounds of reasonableness at the risk of costing ourselves money, health, time with friends/family, and joy.

Story Time​

I vividly remember a customer who checked in to one of our nicer properties (a home with a long, substantive history of 5-star reviews) with a great location, killer mountain views, and nice finishes throughout.

Almost immediately the guest called complaining about how awful the cabin was. “This cabin is just a piece of sh*t!” he yelled on the phone. “When I rent cabins up in New York, they make this place look like a dump.”

“I’m so sorry to hear this sir – what can we do to improve your stay?”

He went on to talk about how the entire property was filthy, everything was broken, the listing was false, the reviews were made up, etc.

Tip: When someone says ‘everything is broken’, they generally mean ‘one thing is sort of not working right but I’m going to leverage this to get as much money out of you as possible.’

Our response?

We had someone at the property within 30 minutes (actual drive time to get there). We cleaned, mopped, “fixed”, replaced toasters, etc. Anything the guest was unhappy with we took care of expeditiously.

Every day for 6 days he would call with a new list of grievances. $190/night for a 3 story, upscale cabin with 3 bedrooms, incredible views, and great location with a long history of largely positive reviews – but in his mind it was a complete dump.

We ultimately wound up giving him $500 back on day two or three in an attempt to appease him – but it didn’t. It was like a shark smelling blood in the water.
Ultimately, he checked out and life moved on, but at the end of the day we learned lessons from people like this:
  • Not everyone wants to be happy on their vacation. Some people want to work you for every dime they can – somehow that rubs their very fragile ego just the right way.
  • Not everyone is reasonable and giving them exceptional customer service every time they call could actually be detrimental to your business by distracting you from the customer base you actually want to earn repeat business from.
  • No matter how big of an annoyance someone is, there may still be times where there are nuggets of truth in what they’re saying. You have to be big enough to take your lumps where they’re due even if someone is coming at you with guns a blazing.
3. If your work/life balance is off, your business will suffer.

I can’t stress enough how important this is.


I’m a workaholic by nature. Most regrettably some of the best/earliest years of my children’s lives are a blur due to the insane number of hours I was working in corporate life and then the property management business. I wish more than anything I could get that time back.

There was a long season of life where I wasn’t taking time off. I wasn’t taking vacations with my family. All I could think about was work and that next thing that needed to be done.

My business partner David was extremely helpful to me in this area – he made me take time off and made me to take fun vacations with the family. 100% of the time I came back fresher, more excited about the business, and more productive in my work than I was before I left. I’m so thankful to have a great friend as a great business partner.

Disconnect to Reconnect
When you go on vacation, your routine is interrupted. The places you go and the new people you meet can inspire you in unexpected ways. As an entrepreneur or business leader, if you didn't come back from your vacation with some ideas about how to shake things up, it's time to consider making some changes. —Sir Richard Branson

Unchain yourself from your business a few weeks a year. Engineer some time off into your schedule for sustainability's sake. Your business will not only survive, it will thrive because you are getting to rest, relax, and enjoy things without the constant stress of the next guest call. Not to mention, the vacation rental industry sort of represents the entire work/life balance as a niche business – don’t be victim to selling a dream you never experience yourself!

Photo: Wes and his family

4. You must "process out" your business if you want to survive.

The best and most valuable way to grow your business without losing all sense of personal quality of life is to "process out" everything for yourself and for your staff.

Having solid processes in place makes it so easy to slowly replace yourself over time without making huge sacrifices in quality for your brand. This will in turn allow you to focus back on things that matter the most like your spouse, your kids, grandkids, hobbies, your spiritual life, traveling, vacations, etc.

Not having solid processes in place will, among other things, almost completely guarantee that your life will be dragged along by your VR business, ensure zero quality of life, and either burn you out or leave you with mediocre business success over the long-haul.

Processes need to be deeply ingrained from day one, but even if this is year 20, it’s never too late to start reaping the benefits of properly incorporating business-process driven culture at your company. Don't forget why you got into this industry in the first place.

5. You must be willing to learn from your competition and other companies.

Along the road to success there will be many forks in the road where you aren’t sure which avenue to take. There will also be times when you need to backtrack and start over to allow segments of your business to perform better.


Some of the best ideas we came up with were from peeks behind the curtains we could glean from competitors, presentations we’ve seen at conferences, or from experiencing a stay ourselves by booking with other PMs at destinations when we would take vacations.

Had we walked in to these scenarios assuming we knew how to do everything better because we were young, hip, and fresh, I think we would have fallen flat on our faces in a lot of areas.

Yet, because we were eager to learn, eager to invent and improve upon others ideas, we were able to glean methods of running a successful property management company that we never would have been able to otherwise.

We both tried to experience every interaction with another PM (competitor or not) as an opportunity to see how they did things, consider the benefits, and make positive changes in our brand if we could. Even when it was a company we thought was different from us, there was always a nugget in there that helped us be successful because we were willing to look for it.

In looking back, we realize that one must stay eager and willing to learn if you want to continue to grow and be successful over the long-haul.

Photo: Wes and David at LiveRez Conference

6. If you have a business partner, fight to keep the relationship strong.


This one is admittedly more touchy-feely, but none-the-less true.

David and I have a long and deep friendship, and while it would be fun to pretend like that’s all it took to keep our relationship healthy through the growth, heartaches, headaches, and tragedies, it wouldn’t be very honest.

Even as great friends with an uncommon level of loyalty, there were days where we both had seen each other too much, were ready for the other to take a few days off, or were maybe even ready to throw up our hands and walk away.

It’s on the hard days though that you must fight to keep the relationship strong. You’ve got to fight to kill your pride, invite humility, and reach for common-ground.

I can honestly say that David is the only person on earth in my life who truly understood what I was going through on the stressful days, on the days where that one owner was about to drive me up a wall, or when I had been going 3 weeks straight without a day off and just needed five minutes without another crisis.

You know why David got it? Because he was doing it too – we were in the fight together. No one who isn’t a property manager can understand the unique wear and tear that running a property management company takes on someone. They may think they do – but they don’t.

Underestimating the value of the human element in your business can be the riskiest decision of all. Fight hard to keep your business relationships strong – having people beside you that “get it” and are loyal will be a tremendous help to your psychological health as you fight to grow your business into something you’re truly proud of.

Photo: Wes and David, selfie mode, ON

Wrapping Up​

So now, David and I are out of the property management business and we’ve pivoted in to growing our region’s most authoritative booking channel on

Being a listing site will have its own set of joys and challenges – but we’re ready for it.

A lot of peers and colleagues ask why we sold – why we exited when we were on an explosive growth trajectory.

The short answer? For us we felt that a person can be successful a lot of ways, but a person who is not successful at home is not truly successful.

We improved quality of life quite a bit along the way by following the general guidelines above, but at the end of the day, we knew we were still running a 24/7 business that required more from us than our families could sustainably give. When a solid offer for our business came out of nowhere, it was a no brainer.

Now we’re enjoying nights and weekends with our wives and kids. We’re focusing back 100% on the things we’re excellent at (Technology for me, Marketing/Biz Dev for David), and we’re excited to contribute to the Vacation Rental industry in a whole new way.

We both look forward to continuing to participate in the community and the Inner Circle as well.

Still innovating. Still building things. But at a pace that’s more sustainable for ourselves and our families.

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