Irish Examiner: Feature on @fleetwoodjack


As many Irish students wait patiently for their Leaving Cert results, we meet trailblazer Jack Ring, who bypassed university and uses social media to fund his life of adventure and travel.
Everyone has had moments where they fantasised about drastically changing their lives, but not many of us are brave enough, or, as some people might suggest, crazy enough, to make the massive changes needed to completely alter our reality.
Maybe you have thought about packing a rucksack and leaving your current life behind, starting a new one where waking up on a warm, deserted beach to watch the sunrise is a regular occurrence. No alarm going off at 6 a.m.; no daily grind; no packed commute to a job that underwhelms you. Would you pack it up to live that nomadic dream? 
Meet Jack Ring, known as @fleetwoodjacko to his thousands of Tiktok followers.
Jack Ring was raised by his mother and aunt in Ballincollig, Cork. At the tender age of 28, he is already a veteran globetrotter, having left home initially for a short holiday in Canada in 2019, but still travelling nearly five years later.
Jack has financed his life by becoming a digital nomad. As his interest in travelling to different countries and learning about new cultures grew, so did his TikTok and Instagram accounts. Fast forward to today, and @FleetwoodJacko has amassed over 675,000 followers on Tiktok and over 200k on Instagram, with his dedicated followers watching, and no doubt living vicariously through his energising, funny, and action-packed videos. One minute he’s broke, working in a hostel in Hawaii, next he’s hitchhiking to Panama on the back of a dodgy truck. He’s snorkelling with sea lions in the Galapagos Islands, then surfing the waves in sunny South Africa. He’s endearing, very easy on the eye, and even brings his Irish mammy on a trip or two.
Jack was not keen on school. “I missed a lot of school; I just didn’t suit academia at all,” he says, sounding a bit guilty about it. As a student in Colaiste Choilm, he found it a struggle to finish his leaving certificate, but he managed it, and when all his friends went on to college, it seemed the natural choice for him too.
A few months into his course in Rec and Leisure in CIT, with no idea what he really wanted to do with his life, he dropped out. He wanted to please his mother by going to college, but “even when people were asking me what I was doing, I knew on some deeper level there was something else for me. I just knew college wasn't the right fit.” He got a job in a bar and hoped things would work themselves out. Then, with his uncle’s help, he started an apprenticeship as an electrician, but, much to his mother's dismay, it wasn’t a great experience, and after two years, he walked away disillusioned and even more unsure about his future. 
He was feeling the pressure because all his friends were completing their degrees and following their career paths at this stage, while he felt he was drifting. “This was probably the lowest point for me. I was 22, had no job, no career plan, and all my friends seemed to be moving on with their lives. As I look back now, I didn’t have anything going for me really, probably drinking too often, my mental health was at it’s worst and I just got myself into a rut.” 
 Arguably there is a lot of pressure on Irish 17- and 18-year-old school leavers to rush into a career path without really seeing any of the world; and Jack was feeling that pressure. “ I don’t want to think about what my life would be like if I didn’t try to find another way ” he tells us.
In 2019 a friend invited him to spend the summer in Canada, and that initial trip set him on an adventure that’s still ongoing, five years later. “I knew after my first day in Canada that I wasn’t going to go back home. I just felt so sure.”
It was in Canada, late one night, while drinking with his friend, that Jack posted his first Tiktok video. He was 23, so it was just a fun video about going out and drinking too much, but incredibly, it was viewed thousands of times. “I couldn’t believe it. We were just joking around, and all these people were watching and asking for more, so it seemed like a great way to engage with people and just have fun. I wasn’t thinking about making money at all at the start.” 
As he settled into his new life, snowboarding by day and working as a barman in a high-end ski resort in the evenings, he was constantly meeting new friends at every turn, and as his life evolved, so did the content of his videos. There were more heartfelt chats to camera, more honest, transparent videos about wanting to drink less, and celebrate living in the moment, watching beautiful sunrises and sunsets, and people were enthralled. He still wasn’t making any money from his on line videos but his followers were growing by the thousands.
He’s way too shy to admit it himself, but it has to be said that Jack is beyond handsome, with piercing blue eyes and flowing, raven black hair, but it’s his honest, thick and lilting Cork accent that lends authenticity to him, making him so much more than just another pretty face on Tiktok. His looks have been beneficial recently, as he appeared in a male model calendar in Hawaii. He laughs and is very embarrassed when I bring up ‘Mr. January’.
 “Oh God, that was so random. I was surfing on the beach, had my hair down, and this guy ran up to me, asking if I’d be in this calendar of Hawaiian men for some company or other. He told me I’d get paid, and as I was broke, with literally a couple of dollars in my account at the time, I thought, ‘Why not’? It was funny because I tried the whole time not to talk too much because my accent certainly didn’t sound local!” He adds, “I would have thought modelling was an easy gig before that day, and now I have huge respect for models. The photographer was telling me, Eyes down, shoulders back, mouth open’. God, I was confused by the end of it.” Much to the amusement of his friends and his proud mother back in Cork, he became Men of Hawaii’s Mr. January.
Speaking of his Irish mammy, Jack gained even more fans when he brought his mother on a trip and shared her experiences in his stories. “As any mother would be, she was very worried about me travelling at the start.” Then she came to Hawaii to spent Christmas with him in 2021. ”She’s so cool. She just got stuck in, sleeping on a sofa a couple of nights, and basically just falling into the life I was living. They are some of the best times of my life, sharing moments like that with my mam. She came back for another trip, going round America too. One night she had to sleep on a couch with me. We slept opposite ends and she had to deal with my big feet in her face the whole night.”
After Hawaii, he went to the Galapagos Islands, and this is where his TikTok blew up. He explains  “If you use a song over a video, you get money for playing the song. It’s amazing. I started earning hundreds of dollars without compromising any of my content, just using songs I loved. So, song promotions really saved me in South America. I only started getting into branded promotional stuff much later.”
He then visited Peru (accidentally visiting during COVID); Equador followed where he had a few hairy experiences including one where he was almost robbed at knifepoint but managed to get away thanks to the quick thinking of a kind local. It’s also where he had his first ayahuasca experience, (the native hallucinogenic drug used for medicinal purposes by indigenous tribes for centuries). That experience told him he needed to visit Africa, so for the first time, he stared to hatch a plan to get himself there. He went the long way about going there of course, which involved visiting Columbia to Panama via a 5-day boat journey. Jack landed just as the protests were in full swing in Panama, so he cut things short, hitchhiking along the closed highways, relying on the kindness of strangers, of whom he says there were many. “There are so many stories about some of these South American countries, but honestly, I met some of the kindest people there who were so willing to help me. These people were searching for a better life, travelling out of necessity, and here I was, doing it for fun. The Venizalian people I met, telling me their stories of hardship, just made me acutely aware of my privilege.” He adds “Meeting those lads was one of the most important things that happened to me and got me thinking about how I could made a difference ”. He’s clearly still moved, telling me about the hardships and injuries those men suffered. 
El Salvador and Hondurus followed, hitchhiking and freediving his way cross country. He then went to Texas and travelled all the southern states in a bus with six other travellers, some of whom he had met previously on his South American travels and some he had just met in the US. “The bonds you make with people on the road are great. One girl and her partner picked us up hitching, she’s pregnant now and has asked me to be the godfather to her child. It’s crazy to think we just met hitchhiking, but spending all that time in the confined space of a car talking about everything and anything. It's a great way to really get to know someone”.
But he didn’t stay too long in the States.“America was way more expensive than anywhere I was living before, so I needed to think about financing my trip to Africa. I went back to Hawaii to get some basic things sorted. I worked in the hostel, and did some product placement with brands like Wndrd, Rosetta Stone, and Zebra Teleheath and saved for the trip.
Finally, earlier this year he arrived in South Africa. 
Despite his huge on line following, Jack doesn’t call himself an influencer. He tells new people he meets that he works in hostels, a much more modest approach. He tells me he likes to blaze his own trail when it comes to his social media. “I want to earn my money by doing something authentic” he says, “I’d never just cash in because I have loads of followers. Along with getting getting various surf and diving certs through my year travelling, I also learned videography and got pretty good at editing. I shot a video for the first hostel I stayed in in in Africa and that got over 100,000 views so the owner put me in touch with lots of other hostels, and that’s my way of paying for my accommodation. South Africa is such an amazing place, I was happy to be helping the tourism industry recover after COVID hit them so hard .”
Jack is now getting involved with charity work. He tells me his meeting with the Venezuelan men really triggered something in him. “I'm starting to make videos of inspirational people who I’ve met on my travels and have involvements in NGOs. I want to set up links to the videos so people can donate to the different NGOs. That’s all inspired by my mother who set up an NGO in Cork years ago.”
He’s also putting his new skill set to use by setting up his own surf school: Travellers Surf Camp, and he’s thrilled to tell me his first one has already sold out this October 2023. More will follow.
During our chat, he mentions various relationships, girls he spent trips with here and there, names of girls he travelled with, one who he tried a long distance relationship with, but it didn’t work out.  I get the feeling he’d be a hard one to tie down, with lots of different projects on the go and maybe not ready to commit to a full on relationship just yet. “I’ve met so many fantastic friends on my travels and maybe 90% of my friends now are girls. I didn’t realise there are so many solo female travellers out there and they are all so great to get along with. It’s been a brilliant part of my journey, meeting all these strong women along the way, kinda like my mom” 
Follow AND support  Jack on 
@fleetwoodjack Insta
@Fleetwoodjacko TikTok