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“Personalization is no longer considered an added bonus but a requirement” with Joshin Raghubar and Candice Georgiadis

With a universal consumer shift from products towards experiences, international spend on luxury experiences is on the rise and personalization is no longer considered an added bonus but a requirement. More people are steering away from the big red bus and group tours and looking for a curated, private experience. I had the pleasure of […]

With a universal consumer shift from products towards experiences, international spend on luxury experiences is on the rise and personalization is no longer considered an added bonus but a requirement. More people are steering away from the big red bus and group tours and looking for a curated, private experience.


I had the pleasure of interviewing Joshin Raghubar. South African born Joshin Raghubar is a seasoned African entrepreneur in the media, marketing, and technology sectors. He is the CEO & Founder of Explore Sideways, a leading purveyor of curated, private food, wine and cultural day tours and experiences in South Africa, Portugal and beyond. Raghubar has also founded iKineo, a Pan-African customer engagement agency and Sprout, South Africa’s leading digital media performance firm. Joshin serves as the chairperson of the Bandwidth Barn, Africa’s largest non-profit incubator and accelerator for technology businesses; non-executive director of the Cape Innovation & Technology Initiative (CITi), the public/private sector agency tasked with development of the region as a technology and innovation cluster; and non-executive director of Enke, a non-profit organization that works to empower youth to develop social innovations in their communities. He was recently recognized as a 2019 Laureate for the John P. Mcnulty Prize, which celebrates individuals and their ventures who are using their entrepreneurial spirit and expertise to address the world’s toughest challenges. Joshin also serves as a non-executive director of both the Africa Leadership Initiative (Southern Africa) and the African Leadership Network. He is a fellow of the Africa Leadership Initiative and the Aspen Institute’s Global Leaders Network, a fellow of the United States-Southern African Centre for Leadership and Public Values, and a member of the Bertelsmann Foundation’s global Transformation Thinkers program. Joshin has a business science (honors) degree from the University of Cape Town, and a masters in development studies from the University of the Western Cape’s Institute for Social Development.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

Ibegan my working life soon after South Africa had transitioned from Apartheid to a democracy. As a young man, it was clear to me then, that while we had climbed the ladder of political liberation, there was still a mountain to climb for people of colour for economic liberation. Despite, being from a family of teachers, I became an entrepreneur and a civic activist for building an inclusive technology-led economy. The story of Explore Sideways, is that during the course of building and running two digital and marketing firms, one of our clients was the tourism authority of the Cape (Town) region. The client brief our creative team to develop a campaign to drive more visitors to the Cape wine lands. The insight for our agency team was that there was no comprehensive easy-to-use way to find out about all the amazing wineries and experiences the Cape had to offer, so they reverted to an idea to develop a discovery app for the region. While the client loved the idea, they did not have the budget to support it, so we funded and launched it ourselves. When we realized that the biggest users of the app were independent travel guides themselves, we realised there is a huge need for of-the beaten path, curated itineraries and experiences, matched to the traveller’s unique preferences, and a service that enabled independent specialists to deliver them. We launched Explore Sideways to address this need, and to share the people, places and experiences that inspire us, with the discerning traveler.

Can you share the most interesting story that happened to you since you started your career?

There are so many interesting moments. A recent moment that stands out, is leading a closed group discussion, at the most luxurious palace hotels in Marrakech, with a former Secretary of State, and almost 20 other foriegn or prime ministers on the impact of technology in Africa, now and over the coming years. And most notably seeing them all burn up the dance floor later.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Right in the beginning, the day after we launched the first version of our website, an eCommerce booking platform for the curated experiences we had put together, we waited with bated breath for bookings to start rolling in. After one day nothing happened. The next day we didn’t get any bookings either. On the third day we started to worry and by the fourth…you get the picture. The lesson we learned was to never assume that just because you’ve launched something that you’ve been working on and poured you time, effort and energy into that people will automatically flock to your site/app/store etc and book, download or buy your product. It takes time to build a brand and get your name out there.

What do you think makes your company stand out? Can you share a story?

At the end of the day, people are trusting us with their time. Explore Sideways is a luxury travel firm trusted by discerning travellers, that curates unique private wine, cultural and active experiences and enables a community of approved independent specialists and insiders to deliver them.

One of my favourite stories that exemplifies what makes us stand out is ‘The Table Mountain Wedding’ story. We were approached by a couple from the US that needed help arranging their wedding day. Now, Explore Sideways is not a wedding planning service but we got such a great vibe from the groom and it was just them (they were eloping and wanted to make it really special) so we agreed to help. Needless to say we pulled off what some would call impossible…a wedding on the slopes of the iconic Table Mountain (a national reserve and one of the seven Natural Wonders of the World) with a pastor, an African themed wedding cake (covered in Zebra stripes!) and an arbour included. Not only did we get access to a part of the mountain that isn’t open to the public by vehicle and host a full wedding ceremony in a breathtakingly beautiful spot, but we managed to make this happy couples special day one they would truly never forget…zebra stripes and all!

I think this story really speaks to some of our core values as a business: trust, passion, openness, innovation and action. We’re a small team but when we’re given a challenging brief we do everything in our power to make it a reality while maintaining our client’s interests as the core focus.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”? Can you share a story about that?

We are privileged to work in this industry- it allows us to express our creativity in the experiences we curate, expand our own horizons and well as those of our guests. It allows us to learn and grow, and if we can remind ourselves to keep growing, we find the energy to thrive. Secondly, we get a lot of energy by building and being part of a community. We actively invest in developing our tribe of independent specialists and partners around our mission. It’s more fun to do it together than doing it alone.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

It may sound cliché, but I have to lead with my parents. They showed me how simple acts of personal leadership and consistently having the courage to move into uncomfortable spaces can have profound impact. I grew up during Apartheid in a time of racially segregated schools, and my parents made significant sacrifices that enabled me to attend a multiracial private school on scholarship. While the school experience was exceptional, it is the example of pushing beyond the boundaries others set for you, that I continue to draw inspiration from.

Let’s jump to the core of our discussion. Can you share with our readers about the innovations that you are bringing to the travel and hospitality industries?

A trusted global brand that enables discerning guests to get the best value for time when they wish to experience their trip through an insider lens of wine, food, culture and unique activities. Our model creates a four-sided marketplace of all #sideways approved verticals: matching discerning travellers with independent specialists and guides, insiders to curate and tailor these experiences and the tourism assets from wineries to yachts to restaurants. Explore Sideways provides a simple booking experience, enabled by technology and design, for agents and guests who book directly.

Which “pain point” are you trying to address by introducing this innovation?

In a nutshell, Explore Sideways delivers a trusted way to get the most value for time. We know how precious time is, especially on vacation and have done all the work for you. With so many tour companies and options out there, we’ve single handedly tested every itinerary, sat down with every independent specialist and guide and tasted the wine, guaranteeing a #sidewaysapproved experience tailored to your preferences.

A guide can make or break your experience and matching our specialists with our guests is something our team truly prides themselves on.

How do you envision that this might disrupt the status quo?

With a universal consumer shift from products towards experiences, international spend on luxury experiences is on the rise and personalization is no longer considered an added bonus but a requirement. More people are steering away from the big red bus and group tours and looking for a curated, private experience.

Can you share 5 examples of how travel and hospitality companies will be adjusting over the next five years to the new ways that consumers like to travel?

Personalization, curation, shared economy, sustainability and bleisure travelers (tacking on a personal trip around a biz trip, especially around millennials / remote economy)

You are a “travel insider”. How would you describe your “perfect vacation experience”?

A perfect trip is when I get the best value for my limited time. Luxury for me is an experience I can trust to be authentically best-in-class local, that I enjoy, am inspired by and expands who I am. If you’ve traveled over 10+ hours to a brand new country and only have a few days to explore- don’t try to do it all on your own via google. You’ll most likely end up in touristy areas, waiting in long lines or even worse; a big red bus with 85 other tourists doing the same thing. Instead, spend a bit more to get the value for time, and seek out a local agency (a trusted global brand with hyper-local specialization) like Explore Sideways , who specialize in private, tailor-made experiences dependent on the traveler’s wants, needs and most importantly -time. Because on vacation, time is the most prized asset.

Can you share with our readers how have you used your success to bring goodness to the world?

One of my goals has always been to drive the technology and entrepreneurial ecosystem in South Africa and beyond, working across government, business and society to build an inclusive, future-proof economy. The Cape Innovation and Technology Initiative, where I have been a member since 2005 and chairperson for the past 6 years is leading the continent’s first and largest tech incubator and building an inclusive workforce by placing previously unemployed young people into tech jobs. I was honored to have recently been recognized as a 2019 Laureate for the John P. Mcnulty Prize, which celebrates individuals and their ventures who are using their entrepreneurial spirit and expertise to address the world’s toughest challenges.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Mass adoption of Bitcoin and off-chain cryptocurrencies based on the Bitcoin Standard.

And a global challenge where people spend more minutes each day meditating than they do on social media, would be fun.

How can our readers follow you on social media?

For serious wanderlust and food and wine inspo follow our adventures in South Africa and Portugal, @exploresideways

For personal, instagram : @joshinraghubar

Twitter: @joshin

Thank you for all of these great insights!

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