In the startup world, there’s no substitute for working with the right co-founder. That’s exactly what Henry
Bennett and Paul Loram have found in one another. The two have worked together on multiple startups over the
past 15 years. Their latest venture, YourWelcome, is a POS tablet for rental properties that enable property
managers to sell their own services, moving short-term rentals into a space that was previously only
occupied by hotels.
Henry and Paul joined scaleup ally Roland Siebelink on this week’s episode of the Silicon Valley Momentum
Podcast. They shared their secrets to a successful co-founder relationship and how they’ve been able to find
success in multiple startup ventures:
- How an old house gave Henry the idea for YourWelcome.
- Why constant dialogue is crucial for any startup partnership.
- The importance of having an end goal in mind during fundraising.
- Why startups shouldn’t forget to approach different customer segments in different ways.
- Why some startups will have a second chance to sell to their target group coming out of the pandemic.
Roland Siebelink: Hello, and welcome to the Silicon Valley Momentum Podcast.
My name is Roland Siebelink and I'm a scaleup ally for tech founders. So excited
today because we have with us Henry Bennett and Paul Loram of YourWelcome
dialing in from the UK. Hello, guys.
Henry Bennett: Hey, how are you doing?
Paul Loram: Hey, good to meet you.
Roland Siebelink: Hey, thank you for joining this podcast. This is amazing.
We found a lot about YourWelcome having a lot of traction in the travel market.
But it's always better to have founders explain themselves exactly what the
product does and who it solves a problem for. Henry, do you want to give it a
Henry Bennett: Yeah, absolutely. YourWelcome is a point of sale for vacation
rentals and short-stay accommodation. What that means in practice is we're a
SaaS-based business. We give away a free tablet device that's installed in
short-term properties, such as vacation rentals, Airbnbs, et cetera. And what
the tablet does, it enables property managers at scale to be able to sell their
own services such as late checkout, additional cleaning, in a contactless and
And then we also - because of the amount of distribution we now have - we are
able to do deals with big partners in the food delivery, grocery delivery space,
a touristic space. And every time it gets purchased, ourselves and also the
property managers are able to make an additional revenue. Our product
essentially is really driving short-term rentals into a space where hotels
operate, where they're not just relying purely on occupancy but they're also
looking to increase their service revenue.
Roland Siebelink: Right. Okay. It's very, very interesting. How did you even
find that niche or that market, as we should properly call it, I guess in that
new space of holiday rental that has emerged?
Henry Bennett: It's actually quite a funny story, actually. Paul and I had
just sold our previous business, which was a media-apps based business. Just as
Airbnb was becoming bigger in London, I actually put my house on Airbnb, even
though I've got three young kids, much the state of my wife at the time. It was
a hassle cause my house is very old too, nearly 50 years old. Essentially, what
would happen is particularly American families would actually love coming there.
But basically, they would come in and they would just be like, "This is a
problem. We don't know how to make an open fire. How do the doors work?" Cause
obviously everything's old.
Instead of doing what most people do, which is engage a property management
company to deal with that, Paul and I discussed the solution would be that we
could develop a very simple application, had seven or eight videos. I could
describe how to make a fire in video format and how the doors that don't work
but how do you get them to work. And I just left it out on a pretty crappy old
Android device in my property and basically said to my guests, "If you phone me
and you haven't watched the video, I won't speak to you." But what was quite
interesting, having done it a few times, was the phone calls stopped. We
realized that was pretty interesting. But more interesting was that guests
didn't clear their cache. Basically, I could see that while they're in property,
they were searching for tourist tickets to, for example, the London eye, which
is a big tourist attraction here.
And it sparked an idea of me and Paul that actually, because all short-term
rentals are private residence, if you're able to install a physical device as
search capability in some form of USP for property owners to want to do it,
we're gonna have access to a whole wealth of data and we could then put together
what is a highly-engaged spend the audience with services and actually create a
pretty interesting transactional business. And that's where it started from.
Roland Siebelink: Wow. That's really awesome. And it's so good to see that
often the best startups start with a founder trying to scratch their own itch,
if you will, right? Paul, can you tell us a little bit about the business that
Henry and you were involved in before and how good of a co-founder relationship
must that have been to decide to go in business again together?
Paul Loram: Yeah. Henry and I have been in business now together for about
15 years. This is probably our fourth or fifth startup for us. The last one, as
Henry mentioned, was an app development agency, which gave us a real background
in how to develop this kind of a product. It was a logical thing for us to move
on to, as Henry mentioned, putting together a little app. That's not something
that the average person could potentially do just as a throwaway idea to help
reduce call-outs. But because we had a background in it, it was a fairly easy
thing for us to pull together. And like Henry said, it fulfilled a need, which
we realized would obviously be something that other people may also benefit
As a relationship, we've always worked together incredibly well. We're very
aligned in what it is we're trying to achieve. We have regular meetings. We sit
next to each other in the office and are constantly talking all day long about
product ideas, feature ideas, what customer feedback, things like that. And
that's been true across all of our businesses. And I think that's why it's
worked so well between us. There's just a constant and open dialogue.
Roland Siebelink: Okay. I'd love to delve into this a little bit, primarily
because I often have founders come to me and say, "Oh my God, I have so many
problems with my co-founder. What do I do about it?" Let's start from this best
practice here, if we may. Paul, sticking with you for just a little bit, without
going into the detail of every single business that you had over the years, is
there a red thread that you can identify that comes back time and time again?
The way you work with each other. Maybe the roles you play.
Paul Loram: We have a fairly clear division in terms of how we split things.
And that's what's always worked very well is that Henry is very focused on
ensuring sales work and I'll take over where it comes to the product and the
detail around how we actually implement the ideas that we've come up with.
And that's always worked very well for us. In terms of a thread across
everything we do, I think it's just ensuring that we're both in the loop on
everything that's going on. But yet, there's a clear divide and a clear
responsibility as to who it is that's actioning any particular part of it.
Roland Siebelink: Okay, Henry, over to you, your side of the coin.
Henry Bennett: I think essentially Paul and I have always been of the
opinion that we want to make money. I think that's not always true with
startups. Pretty much everything we've done, for example, if you take
YourWelcome, we had sold a hundred subscriptions without - we didn't have a
product. I'll tell you how early it was. We basically developed the app but had
spent no money or no real thought process at this point about the backend portal
of which you would upload all this information. Essentially, a property manager
would have to go around to each of his properties and individually type in on
But the moral of that story was, from our view, was if I can't sell at least a
hundred subscriptions within the first two or three weeks of this becoming
something, then we probably would have gone on to something else. Because the
reality is that, in our view, any startup founding team on their own should be
able to go and find customers. Because if you can't find 100 customers in your
existing network, within your existing city, within someone you can quickly go
very limited money other than what you’re going to put in yourself, I think
you're gonna have a problem going forward. I do think that it gave us a
confidence thinking, "God, this product is not even a product. It's really an
idea. That we turned into basically an app that didn't really work. But yet,
there's clearly some interest.
Roland Siebelink: It brings me to the side question. How important is it to
have that strong, broad vision for actual product development work? It's a
question I hear from founders a lot. They get bogged down in so many requests
and so many bug reports. The typical story is a startup that runs really fast
when it's five people and slows down to zero around 50 people. Is there
something in that strong vision, that broad picture, that really helps get
Henry Bennett: As you go through the rounds of funding, I think,
unfortunately, you have to focus very much on where do you want to get to.
Sometimes what that means is that fixing problems sometimes for early customers
or customers that are paying a lot less, you, unfortunately, have to prioritize
But there's obviously challenges with that because you might have some customers
that really have helped define your product in some respects. And I think we all
struggle with that a bit in that we see a customer, they've been with us for
four years and they got maybe 10 properties, they've got a problem, for us, Paul
and I, emotionally you want to fix it for them. Because clearly, they've really
stuck with you, been advocates for you. But actually the end goal is,
unfortunately, you have to focus on the future for new customers, bigger
customers, customers scale, et cetera. That's one of the challenges.
Roland Siebelink: Paul, what about you? Does it help to have that strong
vision to prioritize issues within the engineering pipeline?
Paul Loram: Absolutely. I think having a three-month, six-month, and
12-month plan that you can stick to, having a team who you can trust, who will
also move along that journey with you in order to make sure that you hit. Not
obviously, as you correctly identified, you can easily get bulked down in bugs
and various different things that you want to fix or improve. But as long as you
have that vision of this is where we ultimately want to be at this point, you
can then schedule things around that.
And we try various different things, like we only do bugs on Thursdays and
Fridays, which frees up the first part of the week to really soldier on with the
ground division. We try various different things. But I think that having
everybody aligned in that and being able to communicate that across your team is
what's held us through.
Roland Siebelink: It sounds like, Henry, you are absolutely an example of
somebody who has no problem finding an initial market just among your network.
As you said, just pitching and hustling to get these people together. But when
you do find your product-market fit at some point in time, this needs to become
more scalable, right? How do you guys think about scaling up your go-to market?
What are some tricks and tips that have worked for you? And are you focusing
primarily on just one way of getting new customers or is it a mix of multiple
channels that you have competing against each other?
Henry Bennett: We're now in 18,000 properties globally. We're not at scale,
but we definitely aren't streetfighting to get customers, I think it's fair to
say. I think the particular audience that we're targeting is actually very
difficult because the main acquisition channel - and if you talk to vacation
rental tech businesses, they'll all say the same to you - there's a huge amount
of physical conferences.
We normally attend - what'd you think, Paul - 30, 35 conferences a year, all
over the world from Tel Aviv, West coast, East coast, Mexico everywhere, right?
What that does is you get face-to-face with these customers, you get a huge lead
list. We had a conference that was run by VRBO and I think over two days with
credit cards, we took over 50,000 sales at the actual conference. And then a
whole of leads. One of the challenges, particularly with COVID, is that actually
we're all now trying to find ways of doing this. But one of the problems that
you have when you run a property management business is it's a nightmare, right?
It is a nightmare because you wear so many hats.
Often, what property management companies are not doing is Googling for
information. Therefore, digital marketing has varying degrees of success. For
example, keyword search is challenging. We've done a lot with SDRs, literally
cold calling, get them into the funnel. But obviously, committing to a demo is
now becoming a new purchase. It's a huge commitment of time to do a 45-minute
demo for someone you're not actively looking for.
I think it's a constantly evolving feast and we talk all the time between the
vacation tech business, how best to target these. And I think that for us and
many other companies, we really need to see a return of physical conferences.
Cause that is without doubt the biggest acquisition funnel or way of getting
people in the funnel you're going to see. It is a challenge for everyone.
Roland Siebelink: In terms of the go-to market, you said that it's primarily
traditional sales methods. I'm guessing, Paul, that means this is not really a
product-led-growth model that you see in so many other SaaS businesses where it
starts with trial and then you just keep trying to upsell?
Paul Loram: Correct. As Henry identified, our tablet is our hero product. We
do have a secondary product that sits alongside it, which is called YourWelcome
Advance, which is an advanced check-in tool. That has enabled us to open up
slightly new avenues. That enables us to go back and remarket to our existing
customer base to try and upsell to them. It's a complementary product that sits
alongside it but that isn't the same thing.
We're constantly looking for new ways with which to expand our offering but also
prove our worth to our customers. Ultimately, a lot of this comes down to
conversations with customers at conferences about where their pain points set
and how we can solve them. Sometimes we come up with concepts that don't fit in
with our ecosystem and we haven't pursued those. And we're sticking with our
core offering and things that do complement it. It definitely isn't a
traditional way of doing it. It's just about looking for opportunities and
helping our customers.
Roland Siebelink: Paul, getting back to you a little bit, how do you measure
the product success after it's sold? Do you look at usage? Do you look at people
being engaged with it? You have, of course, your users and your property
managers as two different target groups, so it's already getting pretty complex.
How, in your team, do you guys look at, this is what makes a good job for us.
This is what makes us want to correct ourselves because we're not doing that
Paul Loram: Usage is definitely one of our key metrics, for certain. Back in
the days when Henry and I used to run the mobile agency we talked about earlier
on, we used to measure usage of apps in seconds. If you were getting 20 to 30
seconds of daily usage, you consider what you'd built a success. We're very
fortunate that as a hardware business, especially as our product is used for
people to physically check in with it, that means that they're having to pick up
the guests who come to use our product, having to pick it up to interact with
it, so we're able to upsell the benefits.
Now we look at success in number of minutes of usage rather than seconds. That's
been a great metric for us to keep ensuring that we're offering value and that
people are using it for more and more. I also find that the different customer
bases take our product for different reasons. Some people are looking at it
because they want to monetize better. They want to monetize their guests and
offer upsells. We're also able to throw that in as a metric that we track. But
we segment our customers into groups or buckets, as we call them, to look at
what their motivation is behind having the product in their properties. And then
have an individual metric based on those buckets.
Roland Siebelink: Oh, interesting, so you know what they want to get out of
it. And then you track that metric for that specific segment. Is that what
Paul Loram: Precisely. Yeah. If somebody is not so interested in usage time
but is interested very much in monetization, then obviously for us that's the
only driver for ensuring that they've had a successful product from this. We
then optimize and look at how we're positioning the banners on the tablets and
how the journey is to ensure that if they are advertising a late checkout or
equipment hire, or whatever it might be while the guest is in the property, that
that is visible to them at all times to ensure that they're getting the most
from the platform.
Whereas other customers are less interested, not more interested about just
getting their brand awareness out there. Again, we just look at how can we
optimize ensuring that their products - sorry that their own brand - is visible
on the device at all times.
Roland Siebelink: Can I just say, Paul, that that's actually, while it
sounds straightforward, it's actually quite brilliant. And I think really rare
to see that kind of customer focus and segmentation be fully immersed in the
product organization, even where you're able to look at what the different
segments want out of this product and optimize for it separately. Whereas I see
most product organizations obsess, really obsess, over what's the one metric
that will always be our North Star for every single customer out there.
Paul Loram: We ditched that right at the very beginning. I think because I
come from a retail background and because as we talked about our former
businesses, it was very much a case of how can we ensure that people will renew
when it comes to their annual renewal date. And the way to do that is to ensure
they get what they want from it. And because it serves so many needs, the only
way to do it was to compartmentalize the customers. And then, like you say, you
just focus in on each of their individual needs and insure that they're getting
what they need.
Roland Siebelink: We had some good news this week, without trying to be too
specific about the time when this recording gets up, but that vaccines are in
the offing. Maybe there's some light at the end of the tunnel regarding COVID.
Where do you see YourWelcome grow when all this gets a little bit over, more
under control and, what's the big milestone? Where do you see yourselves in
three to five to maybe even 10 years?
Henry Bennett: I think one of the things that I'll say about this is we were
lucky in that we we've got funding. We've got a good runway. I think one of the
advantages of this challenge for all businesses is that some competitors are
going to struggle to come out of it just purely on a runway, cause raising money
for a travel business right now until we know everyone's coming out, is going to
be very challenging because we obviously know.
And I think what's going to happen is there's a massive pent up want to go
traveling. Everyone is fed up with not being able to go away. I think we're
going to see a huge boom. And I also think, the other thing is quite
interesting, which is the other way to look at this is that a lot of customers
say no to us for various reasons, every product. But they might no longer be in
business. Actually, with all these properties coming back on the market, you get
another go at them and it's happened across the world in every market. There's
basically all these properties that were closed to us for whatever reason, maybe
a private equity group or whatever just be like, "We just don't want to do this.
We're looking just to save costs or whatever." They're now back on the market. I
think there's quite a positives around this.
And I think for Paul and I, typically we look to a cycle somewhere between three
to five years for exit. I think that our ultimate aim, and I think we all know
this, particularly in anyone's listening in the vacation rental space, it's such
a fragmented market. And this is why there's been a big roll up that already
happened within vacation rentals. The second one, I think, imminently happening.
I think that for us, the main focus is distribution, distribution, distribution.
But however, what COVID has done to us is that we flipped from a pure growth
business to a profitable business. The last year become profitable. And I
actually think that, for Paul and I, we're not 25, we've got big mortgages, we
got kids. And I think actually running a profitable business to us is more
appealing. But I think also to a future acquirer, it's never been more appealing
to have a huge acquisition, no future potential of profitability against a
market leader that's profitable. I think that that flip has happened with COVID.
I think we see a pretty bright future for YourWelcome.
Roland Siebelink: What other advice would you give to younger, maybe
first-time founders, Paul, that people are listening to this podcast who are on
their first or second startup and want to be as successful as you are?
Paul Loram: I think you touched upon it earlier on, actually, which is not
being rigid about your North star. What our vision was for this on Day One is
not what the product is today. And I believe that the product is significantly
better because we were flexible. And actually, when we came to raise money
initially for it, virtually all of the people who we spoke to, to try and raise
money from, were saying, "Just forget the hardware. Make it an app. Make it an
Because we'd had this prior background, we were able to say, "Well, no guys, we
think you're wrong." And maybe we burned some bridges by telling people that we
thought they were wrong. But equally, we proved ourselves right, to this point,
five years later now in a strong enough position. But I feel like, know what it
is you're trying to build. But equally, stay flexible enough and listen enough
and get out there with your product.
As Henry mentioned, we'd sold a hundred units before we probably should have
done. Getting to that first landmark for us was a real point of going: "Okay. we
know that there's a demand for what it is we're doing. But we'll stay open
enough to be able to work out how can we improve this to a point where it's just
continually getting better."
Roland Siebelink: Okay. I do have to delve into that a little bit more if
you won't mind, Paul. On the one hand, you're saying, "Look, if people don't get
your vision, just seek someone else, even if you have to burn some bridges." On
the other hand, you're saying, "Listen enough, be open to feedback." Who do you
listen to then?
Paul Loram: Well, you trust yourself, right? It's a case of going, "I
believe this is what - or we should I say, as a collective - but this is what we
believe and this is where we think the product should go." However, while you're
on that journey, you're going to get thrown some things. And I'm talking about
from customers. I'm saying the influence of people who are dangling money in
front of you, which early stages you may or may not need. I think because we
were fortunate enough to have exited a prior business, we were able to stick to
our gumption, which obviously first-time founders might not be able to be in the
luxurious position if someone is offering them funds to do that.
But I think it's a case of knowing where you think the right place is to go.
There's many different splinters of this universe, where we would have made our
product into very different things than it is today. But each time we've done
it, we've done it because we've discussed it at length, going: "Is this the
right way for the product to now go?" Ultimately, it has come from our view on
what our customers are saying, not from where the finance is coming from.
Roland Siebelink: That's what I really get out of it, Paul, that you gotta
stay true to your vision in the big ballpark. But in terms of its seeds and
implementation, do listen, particularly to customers not to investors. Is that
what you're saying?
Paul Loram: Correct. Yes, definitely.
Roland Siebelink: Almost the last question, but, you did mention your
typical exit horizon of three to five years. Is that something you recommend
that other founders also follow typically?
Henry Bennett: No. Every circumstance is different. For Paul and I, when we
first started, if you would have talked going into - we went into an accelerator
– if you would have talked to them early, we were very clear. We're like, "We
don't want to change the world. We want to deliver a quality product. We want to
deliver a big old return on our time investment. And then we want to do
something else." We've got a lot of ideas and things that we do we want to do.
We've run the business in that way. To give you a classic example, if you talk
to our staff, we spend no money. For example, if Paul and I travel, which I used
to go to America once every three weeks, I'm staying in $70 a night hotels. The
main reason why that is, is because the end goal is I know that if we suddenly
spend a huge travel budget, if someone comes on with an exit, we're going to get
less value because they'll look at it and your costs are higher. Whereas other
startups, things going quite well, I can stay in a $500. That is not us. It
never has been. That's one of the frustrations some of our staff probably have
is unfortunately, we put that onto them as well.
I do think as long as you know what you're going to do, then you stick to it and
you don't go off course. I think if you start by going, "I want to change the
world," and suddenly I want to exit, but you suddenly got a massive high cost of
acquisition of customers, no future profitability, huge staff bill, uncertain
economic circumstances, suddenly your business didn't look too good. Whereas you
were a darling of VCs six months ago, right? I think it just depends on what you
want to do and where you are in life.
Roland Siebelink: Yeah. Yet another example, I think, of how beginning with
the end in mind really helps make you all these tactical decisions day by day to
actually get to that end point. This was really good. If somebody wants to know
more about YourWelcome, maybe see what jobs you have open at some point in time,
or I won't intro investors to you - but maybe property management companies
that like to check you out, where do they go?
Henry Bennett: They go to yourwelcome.Com. Y-O-U-R-W-E-L-C-O-M-E.com.
Particularly, we're looking for a great digital manager. Anyone listening, get
in touch, definitely.
Roland Siebelink: Excellent. Okay. Well, very good. Thank you so much, Henry
Bennett and Paul Loram, CEO and COO, respectively, of YourWelcome joining the
Silicon Valley Momentum Podcast. This was a great interview. Thank you so much
Henry Bennett: Thanks very much.
Paul Loram: It's been like a little mini therapy session. It's been
brilliant. Thank you.
Roland Siebelink: Oh, really appreciate that. That's what coaching is for,
right? Thank you all the listeners and we'll hear you back next week.
Roland Siebelink talks all things tech startup and bring you interviews with tech cofounders
across the world.