For years, many short-term rental hosts have relied almost exclusively on platforms like Airbnb and Booking.com to fill their properties. But a growing movement is challenging this dependency. At the forefront stands Mark Simpson, founder of Boostly and one of the most influential voices advocating for direct bookings in the hospitality space.
Mark's story offers valuable lessons for anyone managing short-term rentals, from solo hosts to large-scale property managers looking to build sustainable, independent businesses.
In this conversation, we explore the philosophy behind the Book Direct movement, the real costs of OTA dependency, and how technology, particularly AI, is reshaping the future of hospitality marketing.
Mark Simpson was born into hospitality. Growing up on a 200-acre farm in North Yorkshire, between the tourist destinations of Scarborough and Whitby, Mark's childhood was defined by a constant stream of strangers “in my house.” What started as a four-bedroom guesthouse eventually expanded to 14 bedrooms, three holiday cottages, tea rooms, a restaurant, and an open farm attracting thousands of visitors.
"My pocket money was making beds, doing breakfast, working in the tea rooms," Mark recalls.
This early immersion gave him an intimate understanding of hospitality operations, but it also sparked a desire to escape. After pursuing football coaching in America throughout the 2000s, Mark eventually found himself in London working at Qype (later acquired by Yelp), where he discovered his passion for marketing and sales — two skills that would prove transformational.
When Mark's parents approached retirement age, they were still operating without any online presence. Instead the business relied on a physical calendar, a book that had all the bookings written in, and “Tippex everywhere.” Armed with marketing knowledge from his London experience, Mark returned to help modernize the family business, took 20-30 years of offline word-of-mouth reputation, and digitized it.
The property became one of the top three places on TripAdvisor in all of Yorkshire, the most-followed independent business in Scarborough on Facebook, and consistently maintained 60-80% direct bookings. That’s a figure that would become the foundation of his future business.
The pivotal moment came at a hospitality association meeting in 2016. Mark found himself in a room with about 100 property owners, 90% of whom were complaining about Booking.com, Expedia, and this "new thing called Airbnb."
"I just asked this very naive question, like, well, what are you doing to get your own bookings?" Mark remembers. "Everybody just looked at me like a blank expression."
When he explained that his family business achieved 70-75% direct bookings through social media and email marketing, five people from that meeting asked to learn more. Those five people became the first students of what would eventually become Boostly, a platform that has now served over 2,000 customers with more than 10,000 listings and generated over $1,000,000,000 in direct bookings.
The short-term rental industry offers something unique: you can start a business today, photograph a property on your iPhone, list it on Airbnb, and potentially have paying guests tomorrow. This unprecedented ease of entry has created what Mark calls a "blessing and a curse."
"There's no other industry like it," Mark explains. "When you start a business in hospitality, you've got all these plates that you're spinning, all these things that you gotta do. And that one plate on marketing and sales, you can just go, I'm gonna give that to Airbnb. I'm gonna give that to Booking.com."
This convenience has made hosts overreliant. Unlike virtually every other business that must work to attract customers, short-term rental operators can outsource their entire sales funnel to OTAs, until the plate stops spinning.
The real wake-up calls come when hosts lose control. Mark shares a recent example of a Nashville host whose listing was suspended for six weeks after a guest complained about a camera in the property. The "camera" in question? A Ring doorbell, kept outside, and which is allowed under platform policies. Unfortunately, the decision maker didn’t speak to the host. “They just suspended the listing pending investigation" and the host was left with a property that was unable to make revenue or even take future bookings for six weeks.
For a host running a rent-to-rent arbitrage model with bills to pay, six weeks without revenue or future bookings can be devastating. And this isn't an isolated incident. It's becoming increasingly common as OTAs scale operations using AI and call centers without adequate oversight.
Other breaking points include:
"The relationship that people have right now with the OTAs" is fundamentally imbalanced, Mark argues, and more hosts are recognizing this reality.
Boostly has worked with over 2,000 customers and tracked results meticulously. The data reveals a clear pattern: success in direct bookings isn't about having the perfect website or the most sophisticated technology, but consistent effort.
Mark shares a powerful statistic: "If you apply 18 minutes a day over the course of a year to one discipline, whether it's emails or social media or whatever, if you do it consistently every day for just 18 minutes, you actually come in the top 5% in the whole world in that discipline."
Yet many hosts who invest in a direct booking website expect it to work like magic without any marketing effort. When Mark reviews their CRM accounts (Boostly provides all clients with email marketing, social media templates, automations, and workflows), he often finds they've sent one email in six months or posted twice on social media.
"They go, 'Oh, I just got busy,'" Mark says. "And that is literally what separates the people who do well. They show up every day."
While business owners are recognizing OTA dependency as a risk, guests are also changing their behavior. Unlike older generations with strong brand loyalty to Airbnb or Booking.com, younger travelers prioritize finding the best experience at the best price, regardless of platform.
A significant trend emerged on TikTok in 2024 where travel content creators showed followers how to find better rates by booking directly. These videos garnered millions of views and spawned tools like Directo, a Google Chrome extension that alerts users when a better price exists outside of OTA platforms. The extension has been downloaded over 300,000 times.
"It shows to me that from both angles, from the guest and from the host, the mindset has definitely started to change," Mark observes.
The industry is also facing increased regulation, which Mark views as ultimately positive, with important caveats. As a board member of the Short Term Accommodation Association (STAA), he's gained insight into how regulation develops and the importance of industry representation.
"Everybody wants this industry of short term rentals to be more professional," Mark argues. The current ease of entry, where someone can find a property available for rent, agree with the landlord to rent it from them to then add to an OTA, and have paying guests the next day, needs guardrails to weed out bad actors and protect both guests and legitimate operators.
However, fair regulation is critical. The key is having industry voices at the table when regulations are crafted. "If you're not at the table, you're lunch," Mark says, emphasizing why organizations like STAA, PASC, and others play such a vital role in shaping policy.
Mark has been using AI tools since 2017, starting with Grammarly to improve his writing. But the technology has evolved dramatically, and its applications in hospitality are both promising and problematic.
The clearest win for AI in short-term rentals is guest communication. Mark vividly remembers the exhaustion of answering the same questions repeatedly:
"I got to a point in the season where I just wished that somebody would just have a piece of paper stapled to my head with the most common questions that a guest had because I could just stand there and they would just be able to read it."
AI chatbots solve this problem elegantly. They don't get tired, don't take vacations, don't have hangovers, and provide perfect responses every time. Whether it's a question at 2 AM from an international guest or the hundredth person asking about check-in procedures, AI handles it consistently.
The challenge comes with content creation. As AI has become ubiquitous, people can spot AI-generated content instantly. It’s used not just by business owners and tech enthusiasts, but by Mark's non-business-owner friends and even his children.
"Everybody just copies and pastes it without editing it, giving them their own voice," Mark explains. "And it's otherwise known as AI slop."
The telltale signs are everywhere: the same em dashes, the same emojis, the same generic phrasing. When everyone uses AI to generate social media posts and marketing copy without adding their personal touch, the content becomes noise that readers tune out.
Mark's advice is simple: use AI as a tool, not a replacement. Let it help with grammar, structure, and initial drafts, but always add your voice, edit for authenticity, and ensure the final product sounds like you, not a robot.
Looking ahead, Mark predicts that 2026 will be the year of driverless cars (“it’s already started,” he notes, referencing the CES tech event) and 2027 will bring practical robots into hospitality operations.
"I feel like that's the next way it's going to help operators more than we even realize," Mark says, “and that’s exciting.”
Mark's personal brand has been integral to Boostly's success, though he admits it wasn't entirely intentional. Inspired by daily vloggers like Casey Neistat in 2016, Mark began documenting his journey, first while traveling the world with his family, then transitioning to business content.
"People buy from people," Mark emphasizes. In an era of increasing AI-generated content, authentic personal storytelling stands out more than ever.
His daily posting on LinkedIn and other platforms hasn't made him go viral or accumulate hundreds of thousands of followers, but it has resonated with the right people and opened countless doors from speaking opportunities to business partnerships.
However, Mark offers an important warning from his experience: being too synonymous with your brand can limit exit options. When he explored a potential acquisition in 2024, he discovered that buyers weren't just interested in Boostly, they wanted to acquire him personally.
"The people that were interested in acquiring us weren't so much interested in Boostly, but wanted to acquire me," Mark explains. This realization led him to accept that Boostly is a lifestyle business, not something he'll exit from, and he's made peace with that.
His advice for entrepreneurs: build a personal brand, but don't make it everything about the business if you want flexibility in how you eventually exit.
The convenience of OTA platforms that enabled explosive growth has also created dependencies that leave operators vulnerable. As Mark's journey demonstrates, building direct booking capabilities isn't just about reducing commission fees, but about creating a sustainable, independent business that you control.
The hosts and property managers who thrive in the next decade won't be those who work the hardest or have the most properties. They'll be the ones who show up consistently, build genuine relationships with guests, leverage technology thoughtfully, and maintain their authenticity in an increasingly automated world.
As Mark puts it: "If you can stick it out for another 24 months, the other side of this is brilliant. Because it will weed out the crap. The cream rises to the top, and there's going to be a lot of benefits for those who do."
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