Their World with Erika De Santi, co-founder of WeRoad

Chloe ShearmanContent, Social & PR ManagerHuckletree6/29/2022

Welcome to the first edition of Their World. Where Content Manager, Chloe, is meeting with entrepreneurs from the Huckletree ecosystem and beyond in their favourite places.

For the first in the series, she meets with Erika De Santi, Co-founder of WeRoad and member of Huckletree Shoreditch. Erika chooses Finsbury Square, opposite Huckletree Shoreditch in the heart of vibrant East London, as her meeting place. Erika and Chloe speak about the importance of lunch culture, experiences that push comfort zones, scaling in a pandemic, and tips for aspiring entrepreneurs.


So, Erika, tell us a bit about why you chose Finsbury Square as a place that represents your world?

“Finsbury Square marks that sentimental moment of “we’ve made it” as it’s the home of our UK expansion. This is where we scaled our team and trained an entire cohort of travel coordinators. Emotionally, it connects with the rise of the UK WeRoad community”

Erika speaks of how the WeRoad team often take lunch together in the square, something that she misses from her Italian home, where community lunch breaks are sacred. Culturally, it’s a moment for the team to come together and take a moment’s refresh, to catch up on things besides work.

“Sometimes I’ll find myself sitting at my desk with my lunch in an effort to optimise, but then I’m like… no, this is a moment where I can take a break and share the moment with my team. Lunch culture extends beyond this in Italy, too, it’s actually very common to take business meetings over lunch, much more than in the UK.”


Amazing, love that. We need more lunch culture in our lives. Now, tell us about the WeRoad mission.

“First and foremost, WeRoad creates life-changing backpacking experiences across the world for small groups of 25 - 35 and 35 - 45-year-olds. You discover local culture and food, but most importantly you discover much more about yourself, and the people around you.”

Right now, WeRoad is focusing on building the largest travel community in Europe. WeRoad started their journey in Italy, before expanding to Spain just before Covid (we’ll get to that later), expanding most recently to the UK.

“An amazing thing about the UK is the diversity of the travel groups. In Italy and Spain, it’s mainly people native to those countries, but when we travel with a group from the UK, it’s so multicultural.”

From Columbia and Peru to Vietnam, Iceland and South Africa, their destinations are certainly lust-worthy. WeRoad approaches their experiences with passionate attention to detail, fully curating the entire trip. They don’t work with travel agencies to re-sell their trips, and if they want to collaborate with a local partner they’ll contact them directly. Something that makes the experience much more personal for everyone, from the locals to the WeRoaders. They’re the antithesis of a package holiday, providing an experience that’s entirely enriching.


During a WeRoad trip, you’re fully immersed in this experience with other people. You’re sharing cars, sometimes dorm rooms, and having meals together, so the entire experience pushes you out of your comfort zone and enables you to truly connect with the group.


“These days, our generation is so lonely. We’re in such a frenetic rhythm every single day. We don’t have time to invest in getting to know people, which is really sad. Something that my co-founders and I are very passionate about is fighting loneliness. It’s so difficult to make meaningful friends after a certain age.”


And what brought you to WeRoad?

“I was actually in quite a dull moment. The company I had been working for previously had just been acquired by a competitor, and so I was working on a side project in co-living. But everything seemed a little slow and nothing was really clicking - and I really wanted something with momentum. Then, my previous boss connected me with Paolo (WeRoad founder) as he was working on something similar to me.”

We love a good network power story. Erika tells us that at this point, Paolo had launched the MVP but was working on the project with just one other co-founder, Fabio, and so asked her to come on board as a Project Manager. Immediately, Erika threw herself into the project, coming in as WeRoader number two. And from there, it exploded.


WeRoad went from bootstrap to £2.5m in revenue in year one with 2300 explorers heading off on their adventures.


“As human beings, Paolo and I both love to challenge ourselves. So we went for capital so we could boost even more growth. For year two, we set ourselves a target of 5,000 passengers, but quickly we realised we were going to surpass it and upped it to 8,000. We closed that second year on 9,000 passengers and £9m in revenue”


So this was just before Covid hit, right? How did WeRoad survive that?

“It was challenging, but at the same time, it was rewarding - it really made us understand the power of our community. They kept us together as a business, yes, but they also kept us together morally. Our 400+ WeRoad travel coordinators were organising these brilliant virtual dinners, cooking classes, and training sessions - it was so great to see the community so alive. One of their Italian mamas even hosted a class!”

This was all lovely, Erika says, but it doesn’t sustain a business. At the time of Covid, talent retention was a top priority for the WeRoad. Financially, they understood that they could survive for a few months, but they had to strategise for further down the line. So they tested out projects that they hadn’t had time to try before Covid, launching an e-commerce platform selling merchandise and a gift card portal.


“We sold 700k gift cards in April 2020. We found this insane. We sold gift cards to hotels in a pandemic! And 60% of those were new customers, meaning we managed to acquire new customers in this period. We were blown away.”


WeRoad were then wave makers when the market began to open again. Italy and Spain (their key markets at the time) may have been the first to be locked down, but they were also the first to open up again, and 2021 became one of their record years - hitting 10k passengers on native trips.

I think we can safely say that transcends survival.


I’d love to know, what have been the profound moments in your life which have led you to be an entrepreneur?

“I actually didn’t know I had it in me until I started working on WeRoad. It was the first project I’d worked on that had traction and I could really shape. I always saw myself as a creative, as an interior designer or an artist.”

Erika has two things in common with fellow entrepreneurs - she hates doing the same thing for too long, and the idea of a corporate career bores her. What WeRoad has enabled Erika to do, is to jump from project to project, and market to market with a 360 view of everything. Right now, she’s heavily focused on the International Expansion and is based here in London as she oversees the UK expansion.

“That was my profound moment. Realising that I can do a job that's creative and be an entrepreneur at the same time. I’m super curious, I don’t think I’d fit into a corporate role defined by boundaries.”


I’d love to get some insight from you for those who are creative, but perhaps don’t see themselves having entrepreneurial capabilities even if the desire is there. What advice would you give them?

“Easy - three things: Get s** done, learn on the ground, and be aware of every moment you’re in and whether it reflects the future that you’re hungry for”


I have one more question for you. What has been your favourite moment about being part of the Huckletree community?

“I have two, actually. One great memory was when we hosted our selection events and boot camps in the Auditorium for our travel coordinators. My second is the moment we walked through the door to our studio with the whole team and all our boxes.”

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Yes! A real “we’re home” moment. That’s a wrap on the interview. Thanks so much, Erika!

“Absolutely my pleasure”


You can find out more about WeRoad here.

Want to join a community of brave minds? Join us.

Chloe Shearman

Chloe has both a way with words and an appetite for knowledge. She joins Huckletree from a background in the innovation ecosystem with brands such as Plus X and Central Research Laboratory. Previously a self-confessed craft beer nerd, she worked in experiential marketing with drinks industry domineers BrewDog. At the weekend, you’ll find her exploring London with her dog Lillie and getting cosy with a book.


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