The following interview is a conversation we had with Humphrey Bowles, CEO & Founder of Superhog, on our podcast Category Visionaries. You can view the full episode here: $7 Million Raised to Power the Future of the Vacation Rental Industry

Humphrey Bowles
Yeah, I’m great. Thanks, Brett. Great to be on your show. Thanks for having me. 

Brett
No problem. Super excited to have you. Let’s go ahead and just kick off with a quick summary of who you are and a bit more about your background. 

Humphrey Bowles
Thanks, Brett. So yes, my name is Humphrey, and I got sucked into the world of startups back in 2000, 920 ten when I met some of the founders of one find stay at a downstairs dinner party with my next door neighbor. And I loved what they were doing and I just thought that this opened up a world of different opportunities. So for someone who had been otherwise in a corporate career, this was the opening for me for a whole new wide world. 

Brett
Trey, lets dive into the current company today. Superhog everything that you’re building looks like. It was founded in March 2019. Take us back to March 2019. What was going on in your world? What were those early conversations like, and what were those early days like for the company? 

Humphrey Bowles
So Superhog was founded in 2019. I actually founded a previous business called Guard Hog before that. And Guardhog is an insurance company which is still up and running today. And I guess, as I said earlier, I worked for a company called one Fine state. This was a property management company based in London, which expanded out to Paris, New York, Los Angeles. And I ran the head of supply at one fine stay. And the first question the owners would ask me is how much money can I make? Followed by what happens if something goes wrong? And there just wasn’t a good answer to what happens if something goes wrong. There was a load of fun, confidence boosting. It won’t. We know everyone who turns up. But there wasn’t anything really grounded there. 

Humphrey Bowles
So I left the start an insurance company thinking that insurance was going to be the right way to solve this problem. And it was. But it also really wasn’t because simply throwing some cash at someone after their home has been trashed is a pretty sub optional way of solving that question. So that’s then when we started kind of exploring tech and using tech, really to see if we could turn a load of known unknowns into knowns. And we realized that we could, and it made a massive difference in preventing the bad actors getting access to people’s properties. And that’s when we decided to lean into the tech and actually providing a risk management system for property managers and owners, rather than simply leaving it up to chance and then throwing some cash at it when it goes wrong. 

Brett
And can you paint a picture for us today of what the Superhog product looks like? 

Humphrey Bowles
Sure. So we’re a risk management system, and we provide property managers with risk management programs which enable them to make sure that they can answer three really important questions. Who is the guest? Can you trust them? And what happens if something goes wrong? So we provide a suite of risk management tools which range from guest screening to deposit management, all the way through mediation and resolution services. And because every property manager is different depending on their local geography and local market and local regulations, we enable them to curate the right risk management program for them, which can be tailored for them, but also can be tailored to individual listings as well. So it’s a really flexible toolkit which enables them to meet the local regulations and they’re kind of, how do I put it? 

Humphrey Bowles
Depending on what their owners and stakeholders wish them to do. 

Brett
And does this work? If the property is being rented via Airbnb, can the host do a third party push here and push them to these tools? Or is this for off Airbnb? 

Humphrey Bowles
So it’s for both. Airbnb have some pretty tight rules about where and when you can and can’t do it, what you are and are not allowed to do. For instance, you’re not allowed to ask people using Airbnb to sign other T’s and C’s, but you are allowed to take a deposit, you are allowed to collect some personal details, and you need to, because depending on which geography you’re in, it’s local requirements. So it is for all short term rental users and operators. But as you’ve highlighted, you know, different platforms have different quirks. What we’re able to do is to provide a consistency of service across all platforms, which makes it much easier to manage your guests and your portfolio of properties. 

Brett
Is it better for you or is like that ICP, someone who’s not using Airbnb and they’re doing direct bookings? What I’ve seen, just from being a consumer, spending a lot of time booking properties or vacation rentals on Airbnb. It seems like more and more companies are trying to get off Airbnb. They want to do direct bookings. Is that the sweet spot for you? 

Humphrey Bowles
Yeah, probably. We really kick in when a host wants to list their properties on more than one OTA and by listing their properties on more than one OTA, they are by definition going to be interested in trying to take direct bookings. Now where we are as an industry is everyones agreed? Doing some background checks on guests before you hand over their keys is a bit like using a seatbelt in the car. Its just a really sensible thing to do to make sure that if theres an accident, you’re not going to get hurt. So what we enable is for different property managers to implement kind of risk management strategy that they want some like their guests to go through a highly guest interactive journey so that their guests are fully aware that they’re being screened. Others are like, well, I just want to. 

Humphrey Bowles
I guess like it’s a bit like airport security. They’re just like, hey, I just want to wave them onto the plane. But I quite want to have a quick knowledge of who they are. What we’re here to do is not dictate what they should or shouldn’t do. We’re here to help them meet their rules and regulations, which is super important. But then we’re also here to help them do what they think is best for their business and for their owners. 

Brett
What type of traction are you seeing today? Are there any numbers or metrics that you can share? 

Humphrey Bowles
Well, I mean, look, we’re growing really fast. We’ve seen a pretty consistent 12% month on month growth rates. We’ve done the triple. Now we’re looking to do maybe another triple, probably more likely at double with a few industry headwinds which are coming and we’re having a great time. We’re really solving problems and stopping people’s homes that get trashed. And honestly, Brett, that feels pretty flipping amazing. 

Brett
What are those industry headwinds that are coming? 

Humphrey Bowles
Things like inflation, the fairly usual headwinds which are out there today. Less income, people cutting down on holidays, maybe going for five nights rather than seven, maybe traveling a little bit closer to home, maybe not flying rather than going to driving destinations. But we learned a shed load from COVID and that’s allowed us to have a much more rounded customer base. Before COVID were really heavily exposed to urban markets. The new wave of short term rentals, whereas now we’ve got a lot more people who work with us who are involved in the leisure markets. So around lakes and holiday destinations. 

Brett
So you’re what, one year in the business when COVID hits? What’s that like for you? 

Humphrey Bowles
I mean, honestly, it was brilliant. It was totally brilliant. We tested quite a lot and were like, okay, there’s a shed load to build. Let’s get building. And were just able to accelerate our tech process and our tech building process without also having to deal with a half working system and all the BAU that goes with that. So we just got our heads down, focused on the development, focused on enhancements, focused on taking our mvp and turning it into a MLP. And that meant that by the end of COVID were really where we needed to be in order to deliver on what we tell our customers we can do. 

Brett
How would you describe your marketing philosophy. 

Humphrey Bowles
In terms of how we go about getting customers? 

Brett
Yes. And just the general approach. Is it heavy into education? Is it prioritizing demand gen? Is it prioritizing brand awareness? 

Humphrey Bowles
So, for me, the short term rental industry is all about partnerships. You are always going to like, the way to grow fastest is to build the best partnerships with the businesses that need your service the most in order to solve their customers problems, because your customer is also their customer, and your customers customer is also your customer. So we really focused on our integrations with the other tech businesses in the short term rental ecosystem, billing what is an incredibly important hole for property managers. So that’s been the approach that we’ve taken. And the great thing about partnerships is that you can always pick up the phone and check in and go, how’s it going? And making sure that we’re doing what you expect us to do, and they’re doing what you expect them to do. But that’s been our number one marketing drive. 

Brett
What have you learned about partnership building? 

Humphrey Bowles
It’s all about communication. And quicker you pick up the phone and speak to someone, the easier any issues get resolved. And quite frankly, everyone just appreciates the fact that you’re jumping on stuff quickly. So if you ever think there might be a problem, pick up the phone, because there probably is. And it’s not just you that’s thinking it, and it means you can get ahead of it. 

Brett
I see you also have a podcast that you guys host. Talk to us about the podcast. And I know it’s early in, but any benefits that you’ve seen, or maybe the benefits that you expect to see. 

Humphrey Bowles
I mean, getting people to talk and talk in your environment is always going to be a brilliant way to attract attention. And like you, we love normal, down to earth conversations with property managers, with people in the short term rental industry, telling us about what matters to them and how they got started and what’s the best thing about their business and how they think they can improve it, what’s going well and what’s not. And it all feeds into the learnings that you can take in order to help grow your business as quickly as possible, but in the right direction. So it’s a whole information listening, emotional intelligence piece, isn’t it? 

Brett
Going into this podcast, let’s say six months from now, how are you thinking about measuring the impact? 

Humphrey Bowles
I think that you’ve got the really obvious metrics, which are the number of listeners, the number of download, the subscribers, all those kind of things. For me, I guess the real testament to success is being able to identify the actual number of sales that come from it and the people who have found you through listening to the podcast. Because as a percentage of sales, we expect it to be very low. But it’s a really key part of the marketing. How would I describe it? Kind of the dark side of the marketing, where you don’t quite know how people do find you, but the podcast is something where you can send it to your mates. You can say, hey, this told me a lot. And what we try to do is not talk about ourselves. 

Humphrey Bowles
We try and get property managers to talk about them and their businesses, because that is ultimately what listeners want to hear. 

Brett
This show is brought to you by Front Lines Media podcast production studio that helps B2B founders launch, manage and grow their own podcast. Now, if you’re a Founder, you may be thinking, I don’t have time to host a podcast. I’ve got a company to build. Well, that’s exactly what we built our service to do. You show up and host, and we handle literally everything else. To set up a call to discuss launching your own podcast, visit frontlines.io slash podcast. Now, back today’s episode. What about market category? So when I introduced you, I introduced it as a digital trust platform. Are you seeing demand in vacation rentals now, are vacation rentals or property managers? Are they on the hunt? Are they looking for a digital trust platform? 

Brett
Or are you really trying to create demand, educate the market so that they are saying, shit, we need one of these. We need a digital trust platform. 

Humphrey Bowles
So for me, a digital trust platform is another word for a risk management system. Now, I think within short term rentals, we are category creating I think that theres three questions every property manager needs to answer before they hand over the keys of a home to a stranger. They need to answer who is the guest? Can you trust them? And what happens if something goes wrong? Now we are the only business that can answer all three of those questions immediately, globally and we can do that in an instance. So for me we are reshaping and redefining what the answer to that second question that every owner asks is. So every owner asks what happens if something goes wrong and we enable property managers to go, well, it won’t because of this. 

Humphrey Bowles
And then they can take them through the process of what the company does. And if the owner goes, thats not good enough. I also want to collect an id or I also want to do a sex offender check or I also want to take a deposit or whatever else it might be. We can then help that property manager implement that. So there is no way that you can not answer that question for that owner in a way which makes that owner go, you know, help. This property manager knows exactly what they’re doing and I want to work with them. And from my days in property management, what I found is the first question people ask is how much money can I make? 

Humphrey Bowles
You’re not answering that question for any other reason apart from trying to build some credibility and show that you know the market. It’s like a realtor, isn’t it? You might like the person who says it’s going to go for the highest price. That doesn’t mean you’re going to get the highest price. So the real answer which wins that client is being able to answer this question because that’s what’s going to build confidence and build trust. 

Brett
Let’s talk a little bit about messaging. So last week I was spending some time on your site and it was very obvious to me that you have very clear, very crisp messaging. I walked away actually knowing what you do. Oftentimes when I go to a website, I walk away scratching my head wondering what the hell this company does. You guys have nailed it with messaging. Did you do that on day one or was this a journey to get your messaging to this point? 

Humphrey Bowles
100% it was a journey to get it to this point. I don’t think we really knew what we did for the first twelve or 18 months. We didn’t really know what our customers wanted for the first 18 months. So it is definitely a journey, its definitely an involvement. And you’re really kind to say its really clear for me. It can still be clearer. There is still a load of work that we need to do so that when a customer comes to our site they can find what they want to find. In order to answer that question and go, yes, these guys can do it, im going to get in touch. 

Brett
I think that has to be like a Founder’s curse, this idea that a website’s ever done. With our own website, you know, we spend three months, we roll it out and then I’m literally every week, let’s change this. It’s truly never finished. So I can completely relate there and I think every Founder listening in can relate as well. You know, it does have to change, but that also makes sense that it has to change. 

Humphrey Bowles
Yeah, it does. And I think especially from my kind of development, I’ve learned that I’m not the best person to change it. A Founder cannot be perfect at everything. And actually, you know, for me, I’m super passionate about what I do and I love what I do. Being able to communicate that to customers in the most clear way, that’s not what I do in my top 10%. So that’s why you do need to build that team around you to enable the whole business to be as great as possible. 

Brett
Who was the first marketing hire that you hired and not your person? Like what was the first role? 

Humphrey Bowles
I should say so the first role that we hired for was Co-Founder Leo Walton to come along and kind of sit on our senior team straddling sales, marketing strategy, all those really fun startup. We don’t know what were doing but we think we’ve got something great and were going to follow the breadcrumbs to see where are these? 

Brett
And then who was the next marketing hire? Did you jump to a CMO? Did you hire a marketing manager or coordinator? What was that next line of hiring? 

Humphrey Bowles
We went for partnerships. We hired a partnerships manager. That was our marketing strategy. We hired a partnerships manager to come in and manage our partnerships with the other tech businesses in the short term rental industry because we thought that rather than spending a load of money on marketing, we’d spend it on the people who could help us solve this problem for their clients and therefore let’s invest in those partnerships from day one. 

Brett
That’s super interesting. What advice would you have for founders looking to hire ahead of partnerships? 

Humphrey Bowles
Make sure you get the right personality that is going to be able to be the best at that role. We’re very personality driven at Superhog. Really care about making sure that the person who comes and sits in a particular seat on the bus has the right personality to be in the top 10% of what they do. And ideally, that person will turn out to be in the top 1% of what they do, because that’s when you’ve got a totally amazing employee. 

Brett
What are you doing right now to stand out in the marketplace? I feel like I see more and more companies popping up. Not direct competitors, but I think from the perspective of a property manager in this space, theyre being pitched a lot of tools, they’re seeing a lot of stuff. What are you doing to rise above all that noise? Does it just all go back to partnerships, or is there something else outside of that you thinks really led to your success? 

Humphrey Bowles
So it all goes back to integrations. I think there must be a cool word for it in terms of tech inertia. When it comes to property managers having so many options, they simply can’t make a decision, and therefore they don’t. And therefore, what we try and do is to embed our products into our partners products. And therefore, when they sign up to our partners, they also sign up to us. And therefore, we’re able to onboard customers a lot more efficiently because we’re not doing the actual onboarding. And we’re able to service our customers a lot cleaner because it involves one integration rather than three different integrations. So there’s a load of consolidation that happens behind the scenes, which really maximizes both, like our customers experience and journey of using Superhog, but also the guests journey using our tech and our partner’s tech. 

Humphrey Bowles
Because they only give information once. They don’t need to give the information two or three times. And that’s the key. You make it as simple as possible for your customer’s customer and where what our north star is really trying to balance risk management with the guest experience. And I go back to the analogy of airport security. In many ways, Superhog is like Apple security. The first time you turn up, you have to take off your shoes, you have to put all your kit through the scanner, you get added and arms above the heads and everything like that. But the next time you turn up, we can just say, hey, we know you, Brett. You just go get straight on the plane, no problem. And that’s the real beauty of Superhog, is that it’s not really machine learning, it’s just learning. 

Humphrey Bowles
But every time we have a booking, we learn, and then we can make that guest experience even cleaner the next time they go through our platform. 

Brett
As I mentioned there in the intro, you’ve raised over 7 million today. What have you learned about fundraising throughout this journey. 

Humphrey Bowles
It’s a brutal world out there. If you’re going to be a Founder, you need to be. You’re signing yourself up to a lot of rejection, so you need to be able to be like a goldfish. You just need to forget it and move on and not take someone’s negative feelings or views with you. The fact that you can get one person to buy your products means that there’s a market for your products. It might not be a particularly big market and you might need to evolve what you’re doing, but. But you should still be totally pumped that you’ve made a sale. Therefore, go get the second customer. 

Brett
Let’s imagine that a Founder comes to you and they say, hey, we want to build in the prop tech space. We have a product that we’re going to take to market in the prop tech space. Based on everything that you’ve learned so far about the market and bringing technology to market, what would be the number one piece of advice that you’d give to them? 

Humphrey Bowles
So I think, Brett, the first bit of ice would be, you know, amazing. Congratulations. You’ve done something and you’ve tried to do something that no one else has done. That’s so super amazing. I mean, I probably wouldn’t understand exactly what they had done. So I think I’d say go and pitch this to ten different people and get the feedback, see what they say. I’m just in awe of any Founder who is brave enough to go and try and create a new product, a new process, a new way of doing something. And even if they find there’s not a market, they will have learned so much in the process that they will be a completely different human being compared to if they hadn’t tried to have done it. 

Brett
Final question for you. Let’s zoom out three to five years into the future. What’s the big picture vision look like here? 

Humphrey Bowles
So I want to build. I feel like we are building just a super valuable tool for property managers. And it’s a tool that enables them to not have to go through the pain of a property being trashed and the months and months of torment that goes with dealing with an insurance company, dealing with owners whose pride and joy has been destroyed, and having feelings of, how could I have prevented this? So for me, I would love to be in a position where we’re able to provide some level of guest screening for free on the basis it just makes the whole short term rental industry work better. 

Humphrey Bowles
And if we can do that, then we’re going to be able to be really impacting the industry and owners lives in a way that I totally believe we can eradicate bad guests from the ecosystem whereby you’re just not able to get access to properties if you’re not going to be responsible and look after them. 

Brett
Amazing. I love the vision. All right, we are up on time here, and I know it’s late there in London, so I’m not going to keep you any longer here on a Friday. Before we wrap up, if there’s any founders that are listening in, they want to follow along with your journey. Where should they go? 

Humphrey Bowles
Best place is LinkedIn and follow our podcast. 

Brett
Amazing. Appreciate you coming on. 

Humphrey Bowles
Thanks, Brett. Great to be here. 

Brett
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