In this 11‑minute solo presentation, veteran short‑term‑rental host Mark Simpson shares the seven (plus an extra) hard‑earned lessons from a decade‑plus career that generated over $1 billion in Airbnb bookings for his clients. He begins by debunking the myth that Airbnb is a quick, passive‑income side‑hustle, warning that meaningful revenue and time‑freedom typically require at least three years of sustained effort. He then stresses the outsized impact of going above‑and‑beyond for guests—handwritten notes, unexpected assistance, and thoughtful amenities—as a scalable driver of repeat business. Next, he reveals how to unlock mid‑week occupancy by targeting corporate travelers and contractors through niche booking platforms and direct outreach to hospitals, universities, and construction firms. He cautions against over‑reliance on Airbnb’s algorithm, urging diversification across multiple OTAs and a target mix of roughly 65 % direct bookings versus 35 % third‑party channels. He recommends adopting dynamic‑pricing tools (e.g., PriceLabs, AirDNA) to capture optimal nightly rates. He highlights the importance of joining host communities for motivation and shared knowledge. He argues that the single most decisive factor for rave reviews is a superior sleep experience, recommending a variety of pillow firmness options. Finally, he notes that without systematic processes, hosts remain vulnerable to burnout and revenue volatility, and he teases a follow‑up video on building repeatable systems that let the business run with minimal owner involvement. Throughout, he blends personal anecdotes with concrete, actionable strategies aimed at increasing bookings, revenue, and host freedom.
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I've been in the world of Airbnb for over a decade, and I've made over $1 billion in bookings for our clients. But it hasn't always been easy. And over the past 20 years, I've made countless mistakes and at one point felt so overworked I was this close to giving it all up. So in this video, I want to give you the 7 lessons from my mistakes after years of being in the world of short-term rentals that won't just help you make more money, but will give you back more time too. And if you stick around until the end of this video, I'm going to show you exactly how to get more property bookings without relying on Airbnb's algorithm ever again. So let's start with lesson number 1, and it's one that's going to hit home for a lot of you. There's a recent trend that's been going around in the Airbnb industry for the past couple of years, and it's got to stop because it's causing countless hosts to quit. And listen, I almost fell into this trap too, because 16 years ago when I first joined The Grainary, I thought that the STR business would give me a lot of free time, but what none of the gurus told me about Airbnb was that me and my wife ended up just being like ships passing in the night. We were exhausted, had no time to ourselves, and no guarantees that we grow the business despite all the hours that we were putting in. Fast forward a few years and my family and I, we sold that business for 7 figures, but it was only after a few years of hard work, sacrifice, and pulling these all-nighters did we eventually get that free time. Yes, but was it the passive income that all of these gurus on Instagram and TikTok are trying to ram down your throats? Absolutely not. So lesson number 1 is that if you think that you are going to build a passive income from just Airbnb, you are mistaken. The truth is, this business that we called Airbnb will take at least 3 years before you can start seeing any meaningful impact in both your revenue and your life. But as I always say, If it was easy, everybody would have wildly profitable short-term rental businesses. But they don't. Which brings us on to lesson number 2. If there was a way to make more money, get better reviews, and turn one-time guests into customers for life, would you do it? Over the last 16 years in this property business, we've done a lot of things many people would consider weirdly non-profitable. We sent out handwritten Christmas cards to all of our past guests at The Granary. If you were in London recently, I hired an Ed Sheeran lookalike at the Short Stay Summit just to be stand out at an event. But the strangest one was this. A few years into the business, we got a call from the hospital. An elderly couple were due to check in later that afternoon, but they had unfortunately been involved in a car crash. The hospital needed help tracking down their relatives to come and pick them up. It couldn't have come at a worse time. We're in the middle of our busy summer season. We had 5 chefs and staff members on, and we were completely packed out in the tea rooms and the restaurant. But my dad being my dad, he dropped everything. He went to the hospital to pick up the couple and reunited them with their daughters. Well, one of the two daughters anyway, but that's a story for another day. The crazy thing is, despite never having stayed with us before, this family booked our property year after year and became some of our best customers. So that's when I learned that the best way to grow a short-term rental business is by going above and beyond for your guests. Now, this doesn't always mean you have to literally go and pick them up, but for a simple rule of thumb is to treat people the way that you want to be treated. If something's not right at the property, text the guest quickly, drop off groceries before they arrive after a long trip, send a handwritten thank you when they check out. The weird thing is I always found that the more we did these unscalable things, the faster our business scaled. Which brings us on to the next lesson. Do you have a fully booked calendar on the weekend but struggle to get any inquiries Monday to Friday? Well, you're not alone. If I had to guess, 60% of the hosts we work with at Boostly still have this exact problem. But what if there was a way to fill your Monday to Friday calendar too? Well, there kind of is. The way that we did it was to tap into a market that not many people talk about. Because do you know who books midweek stays? Contractors and the corporate business world. And even if you think that your property isn't suitable for this market, you're probably not right. I wrote about loads of the ways that you can do this in my book, The Book Direct Playbook. But for now, a couple of the best are: first, list your property on corporate booking platforms most hosts have never heard of. That's where business travellers actually book, not Airbnb. In America, you've got sites like Furnish Finder. In the UK, you've got your own niche sites. Do a Google search, ask AI, and you'll be able to find them easy enough. The second is reach out directly to the HR or operation teams at local hospitals, universities, and construction firms. One signed corporate contract can fill you up for months and weeks on end. And we've got a great example of this. When we had the family business, uh, I went to a Business Network Institute, BNI, meeting. Those are the ones that normally happen on a Friday. If you're in a stuffy hotel, you have breakfast, have coffee, and you chat, and you get to meet new people. At this one meeting, I got chatting to a guy, Their company had just set up a big potash mining firm about 20-minute drive away from our business, and he was about to have hundreds of contractors fly in, drive in from out of country, from out of town to be situated there for a couple of years. He needed accommodation to fill those people, and I was the person that was sat in front of him going, hey, I've got space. Now, not only did I fill our property from that December to January sort of lull, but I also helped filled out loads of my friends and biz besties in the area with their properties as well, and I was able to pocket a little bit of extra money. So it was a win-win-win. So lesson 3: fill your midweek calendar by tapping into the corporate market. I've got so many more bits of advice on how you can do that in the book, The Book Direct Playbook. Go and grab a copy on Amazon right now. But this brings me on to lesson 4. For the past decade, I've spent basically every waking hour, either playing with my kids, watching Liverpool Football Club, and helping short-term rental hosts avoid the one mistake that sends most hosts back to a 9-to-5. And what is that mistake, you might ask? Well, imagine you're going skydiving. There's a reason why 90% of skydivers jump out of the plane with two parachutes and not just one. And this is the same reason why skydivers usually jump in pairs or groups too. That's because if that first parachute fails, there are multiple safeguards in place to prevent that skydiver from going splat. But most short-term rental property hosts I work with run their business as if they're jumping out of a plane with a single parachute they've never even checked that works. They rely solely on Airbnb to get all of their bookings. And if it sounds like you, you are in trouble. Because when Airbnb brings in more than 90% of your bookings, you're like a skydiver with a faulty parachute, and you're one algorithm change away from making your business Goes black. The truth is, if over 90% of your bookings come from Airbnb, you do not own a business. You have a job, and Brian Chesky is your boss. So lesson number 4 is to solely never rely on Airbnb to grow your business. Do not build your business on somebody else's land. It's fine for a few bookings to trickle in from Airbnb now and then, but you want bookings to come in from multiple channels— on Booking.com, on VRBO, on Expedia, on Agoda, on Furnish Finder, because you need to have those safeguards in place for your business. You want to be seen as many places as possible, because at the end of the day, the more people that can see you, the more people will buy from you. A good mix to aim for is 65% direct bookings to come from you and your own website and your own business and your own marketing, with the remaining 35% to be spread across the OTA businesses. Which brings us in to lesson number 5, which will help you avoid a huge mistake that I made at the start of my journey in short-term rentals. If I could go back to the version of me from 16 years ago with one piece of advice, it would be this. Because back in the days of the Granary, this was probably the most expensive mistake we ever made. For years, we just made our pricing up. We put it up by a few pounds every season because we just didn't want to upset our regulars. But the problem is, even when you know your pricing is wrong, it's almost impossible to figure out the right number for the right night in the right week against your local competition. So if we just use a dynamic pricing platform, we could probably have made double the money we actually did. So lesson number 5 is to use dynamic pricing to stop missing out on lost revenue. Go get yourself set up with PriceLabs or AirDNA or whatever the tools that are out there, and then you're good to go. Which brings us on to that lesson number 6. A few weeks ago, I gave a talk at the Short Stay Summit to over 1,000 people in London. It took me back to the early days of building this property business. 16 years ago, although it was a family business, there were still countless nights where I was by myself changing laundry, chasing up bookings, and replying to guest messages well past midnight. The truth is, growing a successful business is a lonely game, and you're very unlikely to find anyone in your friends or family who just gets it. That's why lesson number 6 is to surround yourself with like-minded community of short-term rental hosts. Short-term rental properties is a compounding business. The gains you make in year 3 are 10 times more than year 1, and by the time you get to year 5, you're 20 times bigger than year 3. But the only way to seize these rewards is to not give up. So I highly recommend that you do go and join a Facebook group, an in-person event, an online community to keep that motivation and to help you keep going. Which brings us on to lesson 7, which is probably the most important one of all. Most Airbnb videos just, they focus on algorithm hacks or SEO tricks. But the truth is, whilst this can work, none of this really is that effective. At the end of the day, success in this business comes down to just one thing: providing a really good guest experience. But what does that actually mean? Well, one of the things we quickly realised was that a guest can have a pretty mediocre stay. The food was okay. The amenities were just fine. Maybe the hot tub was out of action, but these stays can still get the best reviews if the customer has had a fantastic sleep. I mean, think about it. How often have you had a mediocre stay in a short-term rental or a hotel, but still came away feeling pretty positive because you slept very well? What we found is that the best way to guarantee a good night's sleep is to provide your guests with a range of pillows, a mix of hard, soft, and medium firmness pillows. So lesson number 7 is to do everything you can do to give your guest that positive experience. And when you'll do this, you'll get more positive reviews than you can handle, and you won't even have to worry about these little algorithm hacks. Which brings me on to one more lesson I forgot to mention at the start of the video. Most short-term rental and Airbnb hosts spend years building an expensive hobby instead of a real business because they don't have the right system in place. And it's this lack of systems that keeps hosts 1 or 2 bad months away from their business collapsing. So go ahead and watch this video next, and I'll show you exactly how to systematise your business to go from one overworked and underpaid to having a property business that can run without you. Okay, well, it's not going to be 100% passive, but you might have your evenings free every once in a while, and again, and you can stop running around like a headless chicken.
