James Middleton’s learning disorders may be a blessing and a curse for his entrepreneurial ambitions. On the one hand, he has credited dyslexia and ADHD for his creativity and drive. “I think outside the box. I don’t try to think outside the box, it’s just that my route from A to B is a very different one to a lot of other people’s,” he said in the 2019 interview with The Telegraph. That energy led him to drop out of college and take his chances in the business world. 

The disorders are also why he wanted to start his own companies and have no one above him. Responding to a boss is a challenge because he struggles with following directions. “Not because I’m belligerent, but because I have never been able to explain myself, or finish [what I’m doing],” he said. On the other hand, those traits may also not make him the ideal person to handle the challenging day-to-day of a company.

He knows this himself. ” … I have had difficulties with the minutiae of running a business,” he wrote in his Daily Mail essay. Some believe the dyslexia and the ADHD contributed to the dissolution of so many of his enterprises. “He has lots of great ideas, but he’s less practical when it comes to following those ideas through, which is partly due to his ADD,” a friend told The Standard in 2023. “He finds it hard to stick at things.”