Aussie who brokers some of Hollywood’s biggest deals reveals the wild demands one A-list pop star made – and the surprising celebrity who was a dream to work with

An Aussie talent and brand strategist has revealed what it’s really like working with some of the world’s biggest celebrities.

Dylan Davey founded his talent agency The Social Inc. in 2020 when he was just 21, and has negotiated deals with the likes of J-Lo, Justin Bieber, and Gwyneth Paltrow.

He told Daily Mail, he has experienced some ‘wild rides over the years’, detailing which stars he struggled to work with and who he absolutely loved. 

‘J-Lo always sticks in my mind,’ Dylan, 27, said when asked which celebrity sent him the toughest demands to fulfill.

‘She travelled with a touring party of over 45 people, each needing an individual room.

‘[She] requested very specific furniture in her dressing room, a team of 10 dancers, a private jet and even special juice flown in from LA. 

‘At that level, logistics become a military operation – but she was fantastic to work with.’

Jennifer Lopez, 56, embarked on her fifth concert tour, Up All Night, last July, kicking things off in Pontevedra, Spain, before concluding in August in Sardinia, Italy. 

It was her first tour in six years, following It’s My Party, and featured a total of twenty shows.  

Dylan went on to say his work always ‘varies from person to person’, but admitted he finds musicians the hardest to work with. 

‘Not because they’re difficult people, but because their worlds are far more chaotic,’ he said. 

‘You’re working around touring schedules, constant travel and creative cycles, and pinning down time can be a real challenge. 

‘We always try to get proper meeting time, or a call, to build that relationship. Ultimately, it usually comes down to their motivation. 

‘If talent sees a deal as purely transactional, it shows. If they genuinely believe in it, they’ll move mountains to make it work – and everyone enjoys the process a lot more.’

As for the people he has loved working with, Dylan said the ‘easiest’ client he ever had may come as a shock to some.  

‘One of the easiest and most impressive experiences was working with Kourtney Kardashian Barker on her partnership with boohoo.com,’ he revealed.

Kourtney, 46, who is married to Blink-182 drummer Travis Barker, released her first collection with Boohoo in September 2022 during New York Fashion Week.

Her second collection with the brand came in September 2023, with the partnership aiming to promote sustainable practices in fast fashion. 

‘She was genuinely engaged – across calls, creative direction and design details – because she truly believed in the partnership,’ Dylan said of the reality TV star.

‘That’s the difference. When talent really connects with what you’re bringing them, they invest emotionally and creatively, not just commercially. 

‘That deal was the one that really put us on the map. 

‘We spent over a year building a sustainably-focused collection with Kourtney and her team.’

‘It went on to become the brand’s biggest-selling range ever, selling out five times and generating global press,’ he added.

Dylan said it ‘was a real pinch-me moment’ to see the Kourtney x Boohoo collaboration promoted on a billboard in Times Square, Manhattan.  

‘The next day, sitting with Travis Barker and watching her walk the catwalk, with the full Kardashian camera crew capturing everything, was incredibly rewarding,’ he recalled.

‘It reinforced why creating the right opportunity before it’s ever presented is so important. 

‘The better the alignment, the more effort the talent puts in, and that’s what ultimately differentiates a forgettable deal from one that genuinely passes into popular culture.’

Dylan, who claims to have negotiated more than £150 million (AU$293 million) in celebrity deals, said the secret behind his company’s success is ‘authenticity’.

‘The celebrity brand deals that really work are the ones with genuine alignment and passion. The talent has to truly believe in what they’re putting their name to,’ he explained.

‘If it’s just a cash grab, you’ll never get 100% from them, and that’s when deals become harder and can start to fall apart.’ 

‘There’s a huge amount of pressure behind the scenes. Sometimes you’re working for months to get a deal over the line,’ he continued.

‘[You’re] juggling different personalities and egos, tight timelines, brand considerations and public opinion all at once. 

‘You often need to make big decisions very quickly. What matters most in those moments is being human and honest. 

‘Trying to impress someone just because they’re famous rarely works. Treating them like people first is my advice.’

Dylan joked that he is ‘half-Australian’ because he grew up between Perth and the UK, with his father, Jamie Addicoat, becoming one of the ‘first’ celebrity trainers.

‘My dad was one of the first celebrity personal trainers, he trained people like Kylie Minogue, Ozzy Osbourne and Madonna in the ’80s and ’90s,’ Dylan said.

‘He built a really unique brand by being tough, uncompromising and disciplined. 

‘[He] went on to have best-selling VHS tapes, books and TV appearances around the world.’ 

Dylan’s upbringing ‘shaped’ how he approaches talent today and he wants to bring his new brand, The Social Elite, to Australia. 

‘Australian talent tends to have a confidence that doesn’t tip into entitlement – they are ambitious but also come across really well,’ he said.

‘The entertainment industry in Australia is tough, with fewer opportunities, and that creates a pool of talent with real drive and professionalism. 

‘They show up prepared. Many Aussie actors have had to prove themselves in smaller markets before breaking internationally, which definitely builds resilience.’

He said that stars like Nicole Kidman, Margot Robbie and Jacob Elordi are ‘normal, personable and professional’ despite the fame because of their Aussie roots. 

‘That’s exactly why we’re now expanding The Social Elite into Australia,’ he said.

‘There’s an incredible pool of talent and brands here that are globally relevant but still authentic.

‘That combination works extremely well in the bright lights of Hollywood and on the world stage.’