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with Doron Meyassed, CEO & Co-Founder, Plum Guide

Disruption Diaries

with Doron Meyassed, CEO & Co-Founder, Plum Guide

Doron Meyassed lives and breathes travel. As Co-Founder & CEO of Plum Guide, the world’s leading curated homestay collection, he has proven himself to be a true disruptor.

In 2008, Doron co-founded Promise Communities (now C Space): a company specialising in solving brand, innovation, and insight challenges through mass online collaboration. Looking back on this experience as his apprenticeship, in just 8 years he grew the business into a 140+ strong agency delivering programmes for the likes of Twitter and Spotify.

In 2016, he went on to co-found Plum Guide, redefining the vacation rental landscape and taking on juggernauts like Airbnb to offer a more elevated, luxury experience for the discerning traveller. Today, the business boasts millions of annual users and lists 42,000 of the world’s most beautiful rentals.

Having moved country every few years with a totally undetectable accent, Doron is a true global citizen. In our latest episode of Disruption Diaries, Jo Dalton finally caught up with this straight-shooting nomad to find out more about the ethos and attitude that defines his leadership and sets Plum Guide apart.

The origin story

A diehard Airbnb user, it was on a trip to Tel Aviv that the idea for Plum Guide began to take shape. Checking into their third choice rental, Doron and his group were expecting disappointment. Instead, the home exceeded their expectations on every level.

“We showed up at this place and it was incredible. It’s made of Jaffa stone, the owner would put fresh produce in our fridge every day, and we’d have amazing conversations in the living room, because [as the owner explained] the secret to a good conversation space is cocooning.”

It prompted the question: why was booking a homestay experience such a lottery?

“That was the beginning of understanding that there are these people buried in the depths of Airbnb that are craftspeople; they’re thinking about every piece of furniture and choice of bedding. I took a week off to meet people who I thought were like that in London, Berlin, and Paris, and at the end of that trip I realised, ‘Oh, I really want to do this thing.’”

Assembling a team of architects, travellers, interior designers, and psychologists with the single objective of identifying what makes the perfect stay, Plum Guide was born.

Plum Guide Paris
View from the Plum Guide’s Gold’n Marble apartment in Paris
Building a business, thoughtfully

To date, Plum Guide has secured Series B funding and is a $60 million revenue business. Top publications like Architectural Digest, The New York Times, and Harper's Bazaar sing its praises, and last year the business was named one of Conde Nast Traveller’s Readers’ Choice award winners in the Best Villa & Homestay category.

In amongst all that success, is there a moment that stands out as Doron’s proudest achievement?

“When we raised our Series B, it was suddenly, ‘Wow, we've made it’. But that's not what I feel most proud of today. I think we over-celebrate that stuff.”

Instead, it is a commitment to his own values and a heavily-protected work/life balance that is the source of most pride.

“I’ve managed to have another life alongside a business - friends, family. And I’m very proud that I’ve managed to build a business while keeping my humanity. I’m very thoughtful about how my actions make people feel. Obviously, I mess up like everyone else but I used to have this narrative in my head that you had to be a d*ck to succeed. I’ve managed to remain true to who I am. I think we’re a very people-friendly company.”

Failure is not an option

Success hasn’t always come easy though, and by Doron’s own admission, Plum Guide has at times been a victim of bad timing and circumstance. The global pandemic, which decimated the travel industry, comes to mind.

“We’ve definitely had a lot of bad luck. When COVID hit, we were just in cities. Afterwards, travel brands who had vacation rentals in the Cotswolds or Ibiza did quite well. We were dead for 18 months because we were 100% cities and 92% international.”

So how did the business beat the odds to survive, and outpace recovery in the travel sector?

“Extreme perseverance, and a sense of ‘failure is not an option’. A group of people who were really determined for that to be the outcome. There’s always a solution. There’s always money somewhere. You can get yourself out of any hole. I think it’s just that belief and determination.”

Creativity and the love of beauty

Looking more closely at the purpose and mission behind Plum Guide, Doron explains that there is both professional fulfilment, and a deeper, more personal sense of drive.

“The very vulnerable, personal answer is I feel most at ease when I’m doing it. I love creativity in the broadest sense of the word; by creating, inventing, problem-solving, my head leaves my head alone. The universe is in equilibrium.”

“I love beauty. I love making beautiful things and shining a light on artistry. You know taking a home, merchandising it, and bringing it to people’s radar, creating great holiday experiences - is what it’s about.”

Plum Guide Joshua Tree
Desert Skies, a Plum Guide property in Joshua Tree, California
How to be a CEO

There are many inspiring figures from Doron’s past who have had an impact on different phases in his life, but one lasting relationship stands out.

His first job after graduating from the London School of Economics, saw him mentored by Roy Langmaid, a leading consumer psychologist who has worked with everyone from the Labour Party to British Airways. His learnings are never far from mind.

“A lot of my fundamental beliefs of how to do business come from him. He had these lines that have stuck with me and really informed how I work today.”

Two of his favourites?

  • Breakthroughs are the source of unreasonable requests

“One of his famous projects was getting the first beds into British Airways Business Class. And so his whole thing was: that was an unreasonable request. If you have an organisation that can flirt with an unreasonable request, you have much bigger chances for breakthroughs.”

  • What you resist, persists

“If there’s something between us and I’m annoyed and we don’t talk about it, it’s just going to persist. If you walk into a room and someone looks like they’re sulking and you don’t say anything, that is just going to persist. That’s influenced me.”

Others have advised Doron to present himself as ‘more CEO-like’, and while he can see the merit in this approach, it’s a code of conduct that he doesn’t fully subscribe to.

“I’ve had endless mentors who I really respect, coach me over the years to be a bit more guarded, a bit more deliberate about how I want to be perceived. But I couldn’t follow it. I tried, but it’s just not me. We’re going to die soon. F*ck spending it being serious and presidential if it doesn’t fit with who you are.”

The invisible gorilla

How does a busy founder manage the working week? What are those productivity hacks that help Doron work to his fullest potential?

“The biggest challenge for me in my role, is that the world prioritises me, rather than me prioritising the world.”

An obsessive planner of his week, Doron has found that he can schedule his way through this challenge. He spends time every Friday planning the following week, selecting two or three key goals to achieve, before breaking those down into detailed tasks and adjusting his calendar to make time for their implementation.

The downside is that you can often “confuse efficiency with effectiveness”. It’s why he surrounds himself with a diverse team of divergent thinkers at Plum Guide.

“I think these people see the gorilla. I miss the gorilla. So I rely on people like that around me to go ‘hey, listen, while you’re busy being effective…there’s a gorilla.’”

I can, over IQ?

What advice does he have for other founders beginning their journey?

Early on, Doron honed his talent for attracting top talent. However, despite positive feedback from the Board and Investors, it began to present more challenges than opportunities.

“I overvalued pedigree. Big mistake. I've totally changed my view on that. After I sold my previous business, I reflected on it. My biggest learning was: hire experience. All I did was hire ‘I can, over IQ’. So I went the other way. I spent a lot of money and wasted months and years doing that.”

His hiring approach at Plum Guide now focuses on diversity of experience and background.

“This goes with JD&Co’s values: diverse management teams outperform homogenous management teams. I don't necessarily mean diversity or gender or sex or race, although, of course, that diversity is part of it. I mean having a CTO who has been at Microsoft, and a CPO who has 4 years of experience.”

Rather than a brand fixation on those from top-tier organisations, Doron has learnt that big companies don’t always equal big results.

“If you’ve only worked in big companies - I’ve seen exceptions - it’s harder to have that flexibility and hunger and commitment when things get tough, when your business goes to zero.”

What about his relationships with Plum Guide investors? What advice can he give to those founders who are hesitant about taking the VC route?

“I know some people think it’s a terrible idea, but I treat every single one of my investors like I do a friend. I’m a salesperson at heart, but I don’t bullsh*t. I ask for feedback. The structure of every Board deck starts with ‘here’s what’s gone well, here’s everything that’s not working, here’s where we’re unsure.’ I am very transparent.”

Plum Guide West Sussex
Plum Guide’s The Lakeside Retreat in West Sussex, as seen on Grand Designs
The next chapter

Looking ahead to the future, Doron finds it useful to think about the business as a story in three chapters.

1. Defining the perfect stay

The first chapter focused on developing the science behind the perfect stay. The ‘Plum Test’ ensures each property is qualified against 500 data points, from measuring the WiFi speed and shower pressure, to ‘soft’ criteria like the design aesthetic of a home. To date, 800,000 rentals have been vetted with just 3% of homes making it through the process.

“By an order of magnitude, we have the best NPS in the sector, the best customer satisfaction scores. Then we said, ‘we need to scale this thing.’”

2. Scaling

The second chapter was defined through investment in ‘curation AI’, which revolutionised how quickly the platform could add rental supply.

“We’re opening new markets and we’re continuing to invest in that automation of supply growth. Today, our cost of adding a home is less than a tenth of what it was 2 years ago. And our NPS is higher, because that for us, is always the key.”

3. Growth

So what does the future hold for Plum Guide? In simple terms, “growth”.

“As I now turn my eye to the third chapter, we’ve really under invested on the demand engine. There’s where I see a lot of investment going: into building a more sophisticated marketing engine, and doing a few strategic partnerships that really shift that.”

Doron's top tip for aspiring entrepreneurs:
  • Get organised

“When I started Plum Guide, one of the best things I did was I sat down and took the process of starting a business and put it in a spreadsheet - into 180 tasks, what I was going to do every single day for seven weeks - and I didn’t deviate, no matter what. Anyone who’s starting out, I think this is a great way to do it, because you can go in so many directions and you can get so lost.”

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