Cahill started traveling in 2005 with his first trip to Lithuania.

In 2016, Cahill posted his criticism towards Malaysia Airlines. He called the food “filthy,” and complained the zero response towards his complaint that the inflight entertainment system (IFE) wasn’t working. He used the inflight Wi-Fi to post an update on Instagram. Soon after, he received a message by someone from Malaysia Airlines saying that their Head of Customer Experience read the post, asking if he has anything that “has transpired so far.” After the post, the crew did not serve him, followed by a prohibition to film. The crew approached him and asked stiffly “Who did you message?” A Malaysia Airlines policy has prohibited it before if the passenger “fail to comply with any instruction of the crew.” Cahill said that the crew were “unfriendly.”

Cahill has a YouTube channel of the same name where he posts airline reviews. He started making them on January 2018. He flies at an average of 150 times per year, and has travelled to more than 60 countries. His most-watched review has over 13 million views. Later, Cahill founded his travel blog Go Travel Your Way in 2013.

In 2020, Cahill flew onboard a Tunisair A330, and shared his “unpleasant experience” at its lounge at Tunis-Carthage International Airport as well as onboard. Central director of communication Sami Blidi said that certain services were closed to the public amid the COVID-19 pandemic. Blidi also criticized Cahill for not wearing a face mask as part of health protocols, and said that the lounge isn’t open until 5am. Cahill took to Instagram to criticize Blidi’s allegations, saying that he entered the lounge at 5:15. He demanded for a better flag carrier for the “beautiful” country. Contrary to the Singapore Airlines incident, he received support on the Internet.