The Holiday Property Coach

07/09/2026

Are you scaling your STR business to grow, to profit, or to sell? Because they are not necessarily the same thing.

When I start working with a property manager, one of the first things I look at is their existing property inventory, the demographics, geography and, most importantly, the profitability of the properties they already manage.

Before we talk about adding another 20, 50 or 100 properties, I want to understand which ones are actually making money, which are creating operational complexity, and what the right next properties should look like.

I learned this in my own business when we deliberately reduced our portfolio from over 200 properties to approximately 175 better-quality, better-performing properties.

Bigger wasn’t necessarily better.

And then there’s the next question: are you building a business that could operate without you and that somebody else might actually want to buy?

In my latest blog, I explore the difference between Scale to Grow, Scale to Profit and Scale to Sell, and why building a profitable, resilient and valuable business should be the real goal.

Because the aim isn’t simply to collect more properties. It’s to build a business that works for you, rather than one that only works because of you.

Read the full blog here:

https://www.theholidaypropertycoach.com/blog/do-you-have-a-scale-to-profit-and-a-scale-to-sell-strategy-for-your-str-business

Lisa Roads helps women in short-term rentals scale, systemise, and successfully sell their property management businesses. Book a discovery call today.

06/09/2026

September and October are shaping up to be VERY busy — and I’m excited about what’s coming next for Women in Short Term Rentals.

📍 First stop: Host Planet Roadshow, Nottinghamshire — 14 September

Women in Short Term Rentals is proud to be a delivery partner for this year’s Host Planet Roadshow, bringing practical, relevant education and connection to STR businesses around the UK.

There are only a few tickets left for Nottinghamshire.

https://lnkd.in/ePRCD89W

And if you’re a woman working in short-term rentals and would like to join me as my guest, drop me a private message — I may be able to offer you a complimentary ticket.

🇪🇸 Then I’m off to Madrid for GuestyVal

A chance to catch up with friends, meet more of the movers and shakers in our sector, hear what’s happening across the industry — and hopefully squeeze in a little Madrid fun too!
But there’s something even bigger on the horizon…

💥 Women in STR Learning Lab | SCALE Fest Barcelona | 25 October

I’m working with a brilliant support team and industry experts to create a dedicated Women in Short Term Rentals Learning Lab at SCALE Fest.

And this isn’t going to be another room where we simply talk at women.
We want to listen.

We want to find out what women working across the STR sector actually need to help them progress, lead and succeed.

What skills do women feel they need more support developing?

What’s missing from current STR event agendas?

Are industry events covering the subjects women actually need?

Are women being adequately supported as AI rapidly changes our sector — or are some at risk of being left behind?

What are the barriers affecting women’s visibility, leadership and progression?

And, importantly, what can we as an industry actually DO about them?

We’ll have a dedicated room with expert table facilitators leading conversations around these questions and more.

The insights we gather will help inform the future direction of the Women in Short Term Rentals mission: elevating the visibility and success of women across our global sector.

Whether you’re a property manager, founder, supplier, leader, employee or industry professional, we’d love your voice in the room.

🎟️ The Learning Lab is FREE to attend, but places need to be reserved.

Sign up using the link below and come and be part of the conversation in Barcelona.

https://lnkd.in/e6ACgPRg

There’s a lot happening — Nottinghamshire ➡️ Madrid ➡️ Barcelona — and I can’t wait!

06/09/2026

03/09/2026

Scale does not always equate to profit

31/08/2026

Every booking through an OTA is a guest you don't own.

You get their money. The platform keeps their details, their email, their loyalty, and their next booking.

And you only really feel it the day the algorithm shifts, the ranking drops, or the fees creep up again. Suddenly a business that felt busy feels fragile.

The problem is that the moment you notice you need a direct booking channel is the worst possible moment to start building one.

Because a bridge to your own guests isn't built in a panic. It's built plank by plank, long before you need to walk across it.

That work is quiet and unglamorous.

Capturing guest details properly.

Following up after a stay so the next booking comes to you.

Building a brand a guest actually remembers.

Giving people a reason to book direct instead of scrolling past you on a listing site.

None of it moves the needle overnight. All of it compounds.

When I scaled to 175 properties, the guests who came back to us directly were worth far more than the ones who found us once and disappeared into someone else's algorithm. That relationship was ours. It held when things around it changed.

So here's the question worth sitting with on a Wednesday.

If your best-performing platform changed its rules tomorrow, how much of your business would still be standing?

The time to build the bridge is now, while the water is calm and you're not desperate to cross it.

Start laying the planks.

31/08/2026

A 6.4 magnitude earthquake.

An explosion at Cyprus's main power station that left much of the island without reliable electricity for weeks.

Flooding.

Internet and communications going down.

A key member of staff suddenly disappearing off the island, just days before we had a huge wedding party arriving.

These weren't scenarios from a business continuity workshop.

They actually happened while I was running my short-term rental property management business in Cyprus.

And there were plenty more.

When you manage other people's properties and have guests staying in them, sooner or later something will happen that isn't covered by the normal day's task list.

The question isn't simply:

"What would I do?"

The much more important question for a growing property management business is:

"Would my team know what to do if I wasn't available?"

Because your business continuity plan shouldn't live inside the founder's head.

When the earthquake hit, we had every property inspected within 12 hours.

Every landlord was updated.

When the power station explosion left properties without electricity and air conditioning during the Cyprus heat, we were able to communicate with guests, work with people on the ground and help guests explore alternative arrangements or repatriation through their travel insurers where appropriate.

Was it easy?

Absolutely not.

There were long hours, difficult decisions and situations we couldn't control.

But we weren't starting from zero.

We had procedures.

We had contingency plans.

We had trusted people on the ground.

And, importantly, my management team were trained and empowered to respond.

That's what business continuity really means.

It's knowing:

✨ Who takes control when something goes wrong?
✨ How do you communicate if your normal technology fails?
✨ Who checks properties and vulnerable guests?
✨ What decisions can your managers make without waiting for the business owner?

We've seen wildfires, floods, extreme heat, storms and power failures affecting destinations around the world.

You cannot predict every crisis.

But you can build a business that is prepared to respond to one.

And for me, that's one of the differences between simply managing properties and running a truly professional property management company.

Your professionalism isn't only demonstrated when everything is going well.

It's really tested when everything goes wrong.

If your current business continuity plan is basically "call me", you don't really have a business continuity plan.

And that's something worth fixing before you actually need it.

When did you last test what would happen if you weren't available? 👇

28/08/2026

If your property management business no longer feels viable, selling the portfolio may not be the answer. Changing the business might be.

When I first started my property management business in Cyprus, I spent a surprising amount of my time counselling distressed property investors.

They had bought off-plan investments based on promised returns and timelines that simply weren't materialising. They were anxious, frustrated, and unsure what to do next.

Today, I find myself having a very similar conversation. Except now, it's with distressed property managers.

Property managers who are facing:

Changing legislation and restrictions such as 90-night rules
Increasing pressure from landlords to reduce fees and commissions
Rising operational costs
Greater competition
Business models that are becoming less commercially viable
More work, more stress, and often less profit

Some are thinking about selling their portfolios. Others know something needs to change, but they don't know what that change should look like.

And there's an uncomfortable question I often ask: If you no longer want your portfolio because you believe it isn't commercially viable, why would somebody else want it?

That's why the conversation needs to start before you reach crisis point. Property managers need to think strategically about spreading risk, diversifying revenue and building businesses that can adapt when the market changes.

Because change isn't going away. There will always be another regulatory change, another shift in traveller behaviour, another economic challenge, another competitor or another pressure on margins.

You cannot build a resilient business by hoping next year will be easier. You build resilience through strategy.

When I ran my property management company, we weren't the cheapest operator in the market. In fact, we were one of the most expensive. But we didn't compete on price. We built an entire service around our landlords, kept expertise in-house, trained our team, became specialists in our sector, and above all, we built trust.

Price wasn't our competitive advantage. Value was.

If the business model that worked brilliantly three or five years ago isn't working today, that doesn't automatically mean you have a bad business. It may simply mean your business needs a new strategy.

Sometimes the answer isn't to sell the business you've built. It's to redesign it.

The market is changing. The question is whether your business is changing with it.

What would you have to change first?

28/08/2026

A buyer looked at two STR management companies last year. Same portfolio size. One sold for three times the multiple of the other.

Same number of properties. Same kind of revenue on paper.

So why the gap?

It wasn't the earnings. It was the structure underneath them.

Here's what a buyer actually sees when they open the bonnet.

In an owner-dependent business:
✔ The knowledge lives in the founder's head
✔ The buyer inherits operational risk, because if you leave, the know-how leaves with you
✔ It gets valued on current earnings only

In a systemised business:
✔ The processes are documented and transferable
✔ The buyer sees a running machine, not a person they have to replace
✔ It gets valued on future earnings potential

That's the whole difference.

A buyer isn't paying for how busy you are. They're paying for what they can take on without you in the room.

And this is the part I want you to sit with… the gap in valuation isn't cosmetic. It's structural.

You can't tidy it up with a nice deck in the final month before you sell. It's built, quietly, over years, in the decisions you make about whether the business runs on systems or on you.

When I sold mine after scaling to 175 properties, nobody asked how full my calendar had been. They asked whether it operated well without me in it.

So the question isn't whether you're building a good business today. Plenty of owner-dependent businesses are genuinely good.

The question is whether you're building one someone else could own.

Which of those two are you building right now? 👇

28/08/2026

"We just need better communication."

If you manage properties for owners, you've heard it. And it often lands right before an owner walks.

Here's what I've learned after 25+ years in this industry.

That phrase is rarely about communication.

It's what an owner can name when they've quietly stopped trusting your decisions. Communication is the symptom. Lost confidence is the root.

Consider it. When you trust the person running your asset, you don't ask for weekly updates. You don't need reassurance. You assume it's handled, because it has been.

The requests for "more communication" start when that assumption breaks.

So when I hear this from an owner, I don't rush to send more emails or add another monthly report. That treats the symptom.

The first thing I look at is visibility.

Can the owner actually see how the property is performing? Occupancy trends, revenue against what was promised, the real numbers.

Were problems flagged by the manager first, proactively? Or did the owner discover them?

Does the owner feel like a partner who's kept in the loop, or someone chasing information that should already be theirs?

An owner who discovers a bad month before you tell them isn't asking for better communication. They're telling you they've stopped believing you have it under control.

Fix the visibility and the confidence, and the "communication problem" tends to disappear on its own.

Ignore it, and no amount of extra emails will save the relationship.

Understanding what an owner actually means when they say this is the difference between saving a property and losing one.

What's the phrase your owners use right before they leave? 👇

27/08/2026

Want to reduce landlord churn? Stop thinking that bookings are the only thing your landlords care about.

Yes, landlords appoint short-term rental property managers because they want bookings, revenue, occupancy and an investment that remains financially viable.

But after 18 years managing properties for landlords, I learned that bookings alone aren't what creates long-term landlord relationships.

Trust does.

We charged a premium for our services, yet many of our landlords stayed with us for years.

Here are 5 things we did that helped us build that trust and longevity:

1. Complete transparency around bookings

Every time we took a booking, the landlord knew about it. When I started operating in Cyprus there was a real lack of trust in the local property management market, and I wanted our landlords to know there would never be a guest staying in their property that they didn't know about.

2. We were proactive about maintenance, not reactive

We regularly checked properties, often at our own cost, because prevention was better than discovering a problem when a guest was arriving. We weren't just managing guests. We were protecting their asset.

3. We carried out full winter property inspections

At the end of the season, we'd inspect inventory, linen and general condition, water systems, air conditioning and pool equipment, redecoration requirements, and repairs and replacements. For overseas landlords in particular, we genuinely became their eyes and ears on the ground.

4. We provided proper account management

We didn't wait for landlords to contact us. We communicated proactively, shared guest reviews, and told them what was happening. Because landlords need to see the value their management company is creating. Don't assume they know.

5. We reported properly, and paid landlords on time

Every month we reconciled income, expenditure and costs, provided property reports and made sure landlords were paid when they expected to be paid. This was non-negotiable. Behind that landlord statement might be a mortgage payment or another financial commitment.

And there was one more principle underpinning all of this: we looked after their investment as if it were our own.

Landlord retention isn't simply about generating bookings. It's about creating a relationship where your landlord thinks: "Why would I go anywhere else?"

If landlord churn is becoming a challenge in your STR business, don't just look at your booking performance. Look at the entire landlord experience.

Would your landlords describe you as a booking agent, or as a trusted partner in protecting and growing their investment? 👇