Picture this. You’re standing in front of a beautiful Italian cathedral. One of the most extraordinary buildings in the world, centuries of craftsmanship right in front of you, and you can’t appreciate any of it. Not because you’re tired. Not because you’re distracted. Because your business cannot function without you, and you know it.
This is where Charles Mullany found himself a few years ago. He’s the CEO and founder of HostGenius, a property management company he’s scaled, lost, rebuilt and scaled again. He started in 2018, hit 100 properties before the pandemic wiped him back down to 25, then rebuilt to 160 in under a year when the borders reopened. He now leads a private network of 43 vacation rental managers operating across 1,600 properties in the US.
“I was going to the Duomo and I was like, wow, this is the coolest building I ever saw,” he told me when he joined The Check-In recently. “That’s what I was saying to everyone around me. But internally, I was ridiculously stressed.”
He has made most of the mistakes so you don’t have to. And the most fundamental mistake, the one he sees constantly and lived himself for five years, is thinking you have a business when you actually have a job with a few helpers around it.
The Test
Charles’s definition of a real business is direct. If you can disappear for 30 days and your operation continues to grow and function without you, you have a business. If it slows down, falls behind, or quietly starts falling apart, you have a job. It doesn’t matter how many properties you manage or what your brand looks like. “It’s not a nice website. It’s not telling everyone. It’s being able to step away.”
This is uncomfortable to hear, particularly for anyone who left employment to build something of their own. Our identity as entrepreneurs is bound up in the idea that we run companies. Charles remembers being at 20 properties, telling everyone about his large and growing business, getting quietly furious when someone called it his “little business.” Looking back, it was just him and a friend driving around managing Airbnbs without even a PMS.
But he’s careful to frame this the right way, because it matters how you hear it. The point isn’t to deflate anyone. The point is that what you’re going through right now is the early stage, not the permanent state. “If you really hear it as ‘okay, what I’m experiencing right now is the early stages, and later, when I get it to a position where I can hire people and step away from it, that is a legitimate thing that can happen,’ then that’s what will get you through the tough times.”
It gets easier as you grow, not harder. That’s the thing most people in this industry don’t believe until they’re living it.
The First Hire Everyone Gets Wrong
The passive income question comes up constantly in this industry, and Charles’s answer is worth sitting with. True passivity, he thinks, is largely a myth, at least until you’ve built infrastructure around your business to the point where even your oversight is managed by someone else.
The mistake he sees repeatedly is operators hiring for a specific role. A maintenance coordinator. A guest support rep. A virtual assistant to handle one defined function. His advice is to ignore job titles entirely at first and hire a generalist. An everything person. Someone you can hand 40 hours of tasks you hate, ask whether they enjoy doing them, and watch whether they’re actually good at it within the first week. “People don’t change. If they’re not good within a week, it’s never going to happen.”
The insight underneath this is simple but easy to miss. Some people genuinely enjoy bookkeeping. Some people are energized by dealing with difficult guests. The tasks that drain you are not universally draining. What you’re looking for is the person whose strengths are a mirror image of your weaknesses, not because it’s tidy in theory, but because the business actually runs better when you’re not forcing yourself through work that depletes you.
The insight underneath this is simple but easy to miss. Think about a pub quiz. Go with five people who’ve been your best friends since childhood and you’ll probably think alike, share the same gaps, and lose. Bring together a genuinely diverse group from different backgrounds and you’ve got a much better shot. Building a business is the same thing. The people who fill your gaps aren’t necessarily the people you’d naturally spend time with.
At the 15 to 25 property mark, Charles is unambiguous: hire this person now. A virtual assistant operating at this level runs between $1,200 and $2,500 a month. He flew to Argentina to meet the one who helped him grow his business. “She was life-changing.” At 85 properties doing around a million a year in commission, cleaning fees and upsells, he says you can fill almost every seat in the business and remain involved only in what you actually want to do.
Stop Waiting for Growth
There’s a habit in property management that Charles finds baffling: waiting. “Name any other business in the world where people just wait for their business to grow. But property managers, I think 80% of them are doing that.”
His antidote is outbound. In urban markets with search volume, SEO is worth the investment. He received hundreds of leads from SEO in Vancouver. But he’s equally clear that in markets where nobody is searching, that time is wasted. In those cases, cold outreach is the answer: find owner contact information from addresses, place a virtual assistant on the calls, and build a pipeline with tracked metrics. Dials made, connects, conversion rate, weekly scorecard.
The numbers, once you lay them out, make the activity feel much less intimidating. Call 100 owners. Twenty answer. Five take a meeting. One signs up. That owner is worth roughly $700 to $1,000 a month in commission. Take that revenue and immediately put it toward buying your own time back.
What he’s describing is growth stacking: pick one acquisition channel, get it working, systematize it, move to the next thing. Not three channels at once, none of which work properly. One channel, tracked, owned. Then the next. And critically, never stop once you have momentum. “The moment you lose momentum, if you take a month or two months off, it ends up costing you four or five months because you’re then optimizing the business instead of growing it.”
At 50 properties, he’d also seriously consider acquisition. “It’s cheaper than it sounds,” he says. Buying a small portfolio or a struggling competitor can accelerate growth faster than outbound alone.
The $60,000 Handshake
Here is where I think a lot of operators make a revealing mistake. They scale to the point where the sales process feels like a burden, hire a salesperson to remove it from their lives, and watch their conversion rate barely move because they never had a closing problem in the first place.
Charles’s view is that most operators convert almost every qualified lead because those leads come through genuine relationships: a neighbor, a referral, someone who’s been watching you manage their street. The problem isn’t closing. The problem is generating enough leads in the first place. So hire someone to do the cold outreach. Don’t hire someone to do the part you’re actually good at.
The reason matters. A homeowner who stays for four years, paying around 25% commission with upsells, is worth roughly $60,000 over that relationship. “Are you going to send a random person to collect your $60,000? I’m going to walk to the bank myself.” Show up for the close. The uncomfortable phone calls that start the funnel? Replace those. The moment when someone is genuinely interested and sitting across from you? That’s yours until the portfolio is large enough that any single deal becomes immaterial.
This is the same principle that runs through the 10-80-10 framework he uses for delegation. You define the task and set the standard (the first 10%). Your person does the work (the 80%). You review before anything goes to production (the last 10%). Nothing goes out without your eyes on it, but you’ve recovered the vast majority of your time. The leverage compounds from there.
What Actually Breaks
The question most operators don’t ask until it’s too late is what breaks first when you scale beyond 20 properties. It’s not guest support. It’s not pricing. It’s the accumulation of complexity across too many different functions at once.
A SaaS company has one product and a handful of functions around it. A property management business has cleaning, maintenance, revenue management, owner communication, guest support, supplies, accounting, insurance, damage resolution and more, all running simultaneously. “It gets overwhelming,” he says plainly. “There are just so many different pieces to do.”
The most common response to that overwhelm, particularly around cleaning, makes it worse. Operators bring cleaning in-house. Now they have two businesses and twice the operational surface area. Sometimes that’s unavoidable. Charles had to do it once because of what he describes straightforwardly as a cleaning monopoly on one island that was taking advantage of every operator in the area. But his best cleaning experience came from a different model entirely: one small company with six or seven cleaners, exclusively handling his properties, whose owner also works part-time in his business as a general manager. He paid them $700,000 in cleaning fees in a year. “I don’t have to think about it.”
The deeper lesson is about connectedness. As a business grows, the job shifts from doing individual tasks to making sure all the pieces talk to each other. Owner expectations, guest experience, cleaning standards, revenue performance, they’re not separate problems. Managing the connections between them is what the CEO role actually looks like at scale. Building systems that let you check the health of those connections quickly, without having to audit every individual moving part, is how you stay sane.
The Better Version of the Story
Charles ended the conversation with something worth holding onto. His life today, running a property management company, a design subscription business and a network of 43 operators, is substantially easier than most property managers running 30 properties. Not because he’s smarter. Because the business got built properly.
The job versus business distinction isn’t meant to make anyone feel like what they’re doing doesn’t count. It’s meant to point toward what’s possible. The operators who stay in the “job with helpers” phase indefinitely are usually the ones who mistake busyness for progress, or who believe that growth will only make things harder.
It doesn’t. But getting from here to there requires making deliberate choices earlier than feels comfortable. Hire the generalist before you’re convinced you can afford it. Do the outbound yourself before you’re ready to delegate it. Stay in the room when a homeowner contract is on the table. Build the systems that let you check the connections without living inside them.
Then, one day, you can stand in front of something extraordinary and actually see it.
Want to hear the full conversation?
This article is based on an episode of The Check-In podcast, where Leo Walton and Sarah Nan DuPré talk with the people shaping the short-term rental industry.
Listen on YouTube, Spotify, or Apple Podcasts.
