Founder Spotlight: Doron Meyassed, CEO and Founder of Plum Guide

Doron Meyassed founded luxury holiday home platform Plum Guide in 2015. Playing in the same arena as Airbnb, Plum Guide accepts only the top 1% of homes onto its books in any location, putting homes through the rigorous Plum Test, which uses a mix of algorithms and physical visits by hospitality experts. Talis first invested in the company in 2019.

Talis’ Matus Maar caught up with Doron to chat about how he manages his time as a founder and CEO, as well as what the future looks like for travel in the post-COVID era.

Matus: Hi everyone, welcome back to Talis’ Founder Spotlight series. We’re excited to have Doron Meyassed, founder and CEO of Plum Guide, with us today. We’re going to hear a bit about the company’s mission and vision, the big idea, and how the company has weathered the global pandemic. We’re also going to chat a little bit to Doron about his personal habits, any wisdom that he can share about his journey, and how to cope with the life of a founder.

Doron is a serial entrepreneur, currently working in an exciting space which includes Airbnb and other travel companies that are hot on the stock market. Plum Guide is doing something slightly different to Airbnb, but we think it’s much more exciting and much more curated.

Hi Doron, great to have you on the on the show. Would you like to say a couple of words about yourself and your background? How did you come to found Plum Guide, and what did you do before?

Doron: Great to be here, Matus, and thanks for the nice intro. I’m not really sure where I’m from: my family is from Israel but we moved country every three years when I was a kid. I lived in Mexico, Switzerland and had a constant change of school and environment.

Prior to Plum, my career highlight was founding a company called Promise Communities. We used to (and still do) build private online communities for brands that they would use to collaborate with customers, staff and experts to solve challenges. Our clients were Google, Twitter, Spotify and a lot of hospitality brands, like Hilton, Jumeirah, One&Only — and that’s where a lot of my passion for hospitality developed. We sold the business to Omnicom, which was an incredible journey: it was really my first experience of building both a digital product and learning how to build community, learning: how do you get experts, creatives and designers to give hours and hours of their time for free? And for the last almost five years I’ve been working on Plum.

Matus: What’s your vision for Plum? It’s curation at scale, playing in the area of Airbnb, but it’s quite different. How do you describe it?

Doron: At the highest level, and in the simplest terms, I’d say that our real long-term vision is to solve the paradox of choice in travel. Travel is a very interesting space: the average person spends 20 hours choosing a home for their holiday. These are not 20 hours of joy, fantasy and exploration: they are 20 hours of arguments, stress and anxieties. The crazy thing is that nine out of 10 times people report feeling an element of disappointment with their stay: they have a feeling that they could have done better. And that at its core is what we want to solve. We would like that experience to take 20 minutes, not 20 hours, and for the customer to be left with the sensation every time that there couldn’t have been a better option for them. For us, that’s the end goal: solving the number one problem in travel. It’s crazy how important travel is in our lives, and will be even more so when we’re allowed to do it again. To feel disappointed nine out of 10 times is just wrong.

The way we’re solving this process is by perfecting meticulous curation at scale. When we open a city, town or village, within 12 to 18 months we aim to vet every single home available in that place, and we accept only the top 1% at three different price points (medium, high and luxury) onto our books. So, if you’re one of our customers, you know that if we’re in that location — no ifs, no buts — we show you the best homes that are there. That removes the anxiety of choice, and removes the disappointment which comes with the inevitable lottery that is booking a holiday home.

Matus: How do you scale that? Because obviously, it sounds amazing from the consumer point of view.

Doron: In the first year and a half or two of Plum, we were really dedicated to figuring out how to create a curation process that outperformed the customer. Because really, the first challenge was the fact that the customer is already out there, reading reviews, filtering properties themselves, and we needed to create a process that outdelivered that. It took almost two years for our NPS to become three to five times higher (depending on the city) than what it would be on the familiar platforms where the customer does it. The next stage was making it affordable and scalable. The two core elements there are automation, and using a community approach.

On the automation front, if we decide to launch a location — like Ibiza or Miami — we have a database at the click of a button of all the homes in that location with contact details that are automatically marketed to where people apply, so it’s really been fully automated. And the second chunk is using the community approach. The most expensive part of what we do is sending the critic to go and test the home. That is affordable, because we’re doing it through a global community of people who do it for passion more than anything else, rather than being full-time staff. We’re using some of what we learned at Promise to build these global communities in a cost-effective way.

Matus: Passion is, I think, a very important part of anyone’s success story. I remember before you started Plum, we had a chat once when you had three potential businesses that you were going to start next. And the two other ones, you said: well, I know I can do this really well and this will be really successful. But I want to do the Plum Guide because I’m so passionate about it and I think it’s going to be huge. It may have even been the riskiest idea, because no one had ever done this before, but the passion there was really your deciding factor. Do you still have the passion for the industry even though you’ve now been working in it for so long?

Doron: Incredibly so. I just have a deep passion for travel. I love travelling and I have a deep passion for interior design. If I ever become too engrossed in the numbers and forget what we’re doing, all it will take is for me to spend four days in a Plum home to remember what it does for me because you get to have your fantasy. You show up in New York, you show up in Palm Springs and you get to live someone else’s life for four days: a movie director, an economist, a restauranteur, and it’s beautifully designed. It’s something you could never imagine doing. And immediately I’m reminded of how much I love what I do and what a fun and interesting space it is.

Matus: It’s really interesting as well, choosing homes rather than hotels for the fantasy of interior design. Almost like fantasising: if I could buy this property, what would I do? Or, if I had a property in Palm Springs, what would it look like? This goes hand in hand with the whole generation of millennials who are living in the rental economy and are less able to buy their own houses, especially the houses of their dreams. A lot of people don’t have the chance, other chance than this, to experience beautifully designed homes.

Doron:100%. And I think it applies to everyone from Gen Z to very wealthy individuals, because interestingly, something about the economics of this is that while you can afford to stay in these places for five days, you can’t afford to buy them. I certainly can’t afford to buy any of the Plum homes that I choose to stay in for a few days.

Matus: Let’s talk about COVID. Obviously, for most technology companies, whichever sector they’re in, there has been some acceleration: either of their business model, or a change of their business model, or acceleration of what their customer adoption looks like. What did COVID do to Plum: how has it made you think differently about the product, and how has the business changed from say, a year ago?

Doron: I mean, there’s no question that COVID hit us hard. Before the pandemic, our homes were 100% in urban areas, with 89% of our customer base travelling internationally for their stays: two of the biggest hit parts of the of the travel sector. So when it happened, beyond stabilising the business and capitalising, the first thing we looked at and asked ourselves, was: do we think that COVID changes the rules of the game in some way — either advantageously, or not to plan?

The positive thing is that I do believe that this whole thing has made our proposition fundamentally more appealing in the post-COVID world. First of all, people are expected to stay much longer when they go and stay in places. Our average length of stay is two and a half times longer for the same homes on Airbnb or Booking.com. I think that’s because when people go for longer, they’re more risk averse, they want to know details like the floor plan of the house, they want to know that it’s been tested and that it’s not going to disappoint: they don’t want to play that lottery. So, I think post-COVID, we will see people become much more interested in curated experiences. People are going to be like, oh my God, I get to travel, and who knows when I will get to do it again — so, actually, I want a beautifully designed home. I think it puts quality assurance curation — so homes over hotels — in a very strong position.

COVID really changed two things about the business fundamentally. We had to ask ourselves, what should we be doing that would make us think that COVID was the best thing to have ever happened to Plum? And we really came up with two things. The first was how we use this time to really figure out how to hyperscale supply, so we set ourselves the goal of reducing the cost of acquiring supply by near 80%, and tripling the velocity at which we do it. We are partway through working towards that goal, but we’ve made a lot of progress and are certainly in the second half of achieving it. I really believe that we will look back and think this was a gift, because the business now is unrecognisable from that point of view.

The second big thing that we worked on was opening new domestic destinations. Previously, we were purely urban: everything we did was around mega cities. We had to do a lot of work to open these new locations: our testing for homes looks different for a place by the beach than it does in the desert, or in a city; the way we recruited was also totally different, so there was a lot for us to figure out. I’m proud to say that that the cohort of domestic homes we’ve launched in this time are outperforming every cohort we have ever launched as a business with much lower resource. Those are the two big fundamental changes for us.

Matus: They’re such amazing homes, I keep seeing them on Instagram, the desert homes and the remote ones in the UK. There’s some incredible houses, right?

Doron: Yeah, some serious house envy out there.

Matus: Let’s chat about your team. Hiring is often always one of the biggest challenges for startups, and finding talent can be tough. Making sure that the talent works really well together can also be hard. As CEO that’s an area that you have to spend a lot of time on. What does the Plum Guide team look like, and what’s your approach to hiring as you scale?

Doron: It’s an always-learning process. I think there’s some there’s some things that are universal, and there’s some things that change during scale. At the beginning, I think the most important thing is hiring hustlers who are generalists: people who can take any problem, figure it out and run with it. The further up the journey you go, the more you want subject matter experts who have worked in this vertical and who have done it before. And for me the trickiest thing is dialing this up at the right speed — we’ve got it right, and we’ve got it wrong. When experts come along, they can add huge value, but generalists bring a magic, energy and impatience that you don’t want to lose.

Some universal things are very important to me: personally, I’m obsessed with clear communicators. I also think it’s important that we hire people with unreasonably high standards. I want to see people who are unreasonable about what they want to achieve. Talking kindly and openly about what’s happening is very important to me too.

I remember doing this course at Harvard when we sold our previous business to Omnicom. There was a section on recruiting, and they asked us to think about the last 100 people we hired, and then to put them into categories in terms of how they had performed. The average for the group was about a third amazing hires, a third hires who had done OK, and a third people who weren’t the right fit. It made me think, hiring is really like flipping a coin. To some degree, it’s as much about knowing when to call a mistake a mistake, and learning from it.

Matus: So, what’s your typical morning routine? I have to say you’re one of the hardest working people I know. We even shared a building with you at one point and I knew you were sometimes there very early, or at the weekends.

Doron: I’m definitely a morning person, I wake up at around 5:30 most mornings. I’ve never had a good idea after midday. I try to go for a run three times a week, and then usually I’m working and at my desk by 7:30. I try to have deep thinking time for the first three or four hours of the day, then usually meetings, and then I try to wrap up at a normal time. I have a very stringent planning process on Fridays and people tell me this is a really quirky part of my routine. Every Friday I probably spend an hour and a half stepping back and asking myself, what are the three things than could happen next week that will make me punch the air with excitement? I then break them into manageable tasks and figure out how long they’ll take. One thing this has allowed me to do is to prioritise the world, rather than let it prioritise me.

Matus: Founders notoriously find it hard to switch off from work. Can you and how do you switch off?

Doron: I find it hard to switch off for sure. The two of the things that I do religiously is that I do a kind of digital Sabbath. On a Friday night, I’ll arrive home and before I enter the house, I will go on the settings of my phone and turn all the emails and notifications off. I don’t look at any emails for about 36 hours which I find really helps.

I also really love baths: it’s one of the few places where I have time to just process everything. I think one of the things that I find helps me destress, or reduce the level of stress around something, is negative visualisation. I don’t know if that’s the formal term for it, and when I tell people about it, they think it sounds counterintuitive. But when there’s a situation that really is causing me anxiety or stress, I play out in my head the worst possible scenario. If the worst possible scenario is, for example, the business going under, I picture telling people about it. I picture the worst of the worst. And I find that immediately within 10 minutes of doing that visualisation, I feel better. I’m able to tackle the challenge from a much more free and positive place. I think the fear of something is so much worse than the thing itself. When it’s intangible, it blows into something that’s filling you with stress, but when you start to picture it, it immediately becomes just a problem that you can play with.

Matus: I do exactly the same thing! Most of the time, I’m like, what’s the worst that can happen? And it’s rarely the end of the world. I think visualisation is good because you stop fearing it, as you kind of already lived it a little bit.

Doron: That’s interesting that you do it too! My analogy is imagining it as a rollercoaster — I love rollercoasters — but for some reason I spend a proportion of my time not with my hands in the air. I find nothing makes me unclench and let go more than visualising it. This is still the ride, just relax.

Matus: Thank you so much Doron. We’re out of time but I really enjoyed it. Thank you so much for thoughtful advice and for opening up. Always a pleasure to talk to you and we wish you all the best.

Doron: Thanks for having me and thanks for continuing to support us with so much so much passion and love!