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In February 2018, Jason left his full-time position at The Walt Disney Company to set up his own Singapore company, Cockatoo Media, working as host of Weekend Mornings on Singapore radio station Money_FM_89.3. He was part of the presentation team for the 2018_FIFA_World_Cup for ESPN India and Sony_Entertainment_Television for Pakistan in June and July and anchored the 2019 Australian Open on Sony_ESPN. He also contributed to the ESPNCricinfo coverage of 2018_Indian_Premier_League and 2019_Indian_Premier_League from Mumbai. Through Cockatoo Media, Jason also works as a media trainer, emcee and website consultant. In late 2019, Jason moved back to Australia after more than 25 years abroad, setting up bases in Brisbane and Sydney. He continued to serve clients across Asia-Pacific, while setting up his own YouTube platform, featuring interviews with pop musicians Greedy Smith and Rex Goh, and author Michael Robotham. In December 2019, he emceed the Asian Football Confederation Annual Awards for the fifth time in his former base of Hong Kong. In January 2020, after a fill-in stint as breakfast host on Money_FM_89.3 Jason anchored the 2020 Australian Open, fronting coverage of the opening Grand Slam tournament for the fourth consecutive year. In February 2020, he began a new Australia tourism radio series called 'Dasey Down Under' for Money_FM_89.3, including a segment with Terri_Irwin and Bindi_Irwin at Australia_Zoo.

In 2014, Jason re-joined ESPN through The Walt Disney Company in a management role with a focus on creating digital content and Southeast Asian commercial opportunities for ESPN FC, having initially worked as a consultant, while winding down his ASTRO commitments. His last hosting for ASTRO was the 2014 FIFA World Cup from Brazil, including the July 13th final. After helping set up the daily ESPN FC Indonesia TV show on Jakarta-based NET. Media, premiering in June, Jason oversaw the November 2014 launch of the Southeast Asia edition of ESPN FC. Later that month, he co-hosted the 2014 AFC Annual Awards in Manila, marking the confederation's 60th anniversary. In January 2015, he reported from Australia from the 2015 AFC Asian Cup for both web and ESPN FC TV show. In April 2016, he interviewed top Asian coaches at the draw for 2018_FIFA_World_Cup_qualification_–_AFC_Third_Round in Kuala Lumpur. In January 2017, Jason hosted the 2017 Australian Open tennis for Sony_ESPN, marking a return to the Indian TV market after an 11-year absence. In June 2017, Jason joined ex-Liverpool striker Emile Heskey for analysis shows around the 2017_UEFA_Champions_League_Final for an invited audience at Singapore National Stadium which were streamed live on the ESPN FC Facebook page. Also in 2017, Jason covered the successful qualification, including two playoffs, of Australia's Socceroos for the 2018 FIFA World Cup. On November 30, he co-hosted the 2017 AFC Annual Awards in Bangkok to coincide with his 40th anniversary in journalism. In January 2018, Jason again presented Grand Slam tennis for Sony_ESPN as anchor of the 2018 Australian Open and appeared as a guest alongside ex-India cricketer Sanjay Manjrekar on episodes of the Run Order show, hosted by comedian Cyrus Broacha.

Away from football, he hosted the 2011 Rugby World Cup and presented 26 episodes of an interview-based show, Golfing Greats: In Their Own Words for Golf Channel in Singapore and Malaysia and conducted in-house trainings for Astro anchors, reporters and writers. As a weekly sports columnist, Jason wrote for several regional newspapers including The Star and 'South China Morning Post" plus the Stadium Astro website. For two years he was chief columnist and consulting editor of the Malaysia/Singapore edition of FourFourTwo magazine and hosted a popular weekly football podcast, Football Fever. In 2009 and 2012, he emceed the Asian Football Confederation Annual Awards in Kuala Lumpur. In 2012 and 2014, Jason received nominations for Best Sports Presenter/Commentator at the Asian_Television_Award.

After almost eight years within the ESPN group, Jason joined Asian satellite network ASTRO in 2009 as vice-president and sports' executive producer. Based in Kuala Lumpur, he built an in-house production team, was chief anchor for Astro's Premier League coverage and hosted seven major tournaments, including 2010 FIFA World Cup, UEFA Euro 2012, 2014 FIFA World Cup. He also devised new programming like FourFourTwo TV Show, Bola@Mamak, BPL Turning Points & Stadium Unplugged. In November 2011, two of the shows were nominated for Asian_Television_Award in non-sports categories: Best Talk Show & Best Comedy Show.

In November 2008, Jason moved back to Asia, setting up a base in Hong Kong while freelancing for ESPN, primarily as a feature interviewer of sports identities like Nick Faldo, Bernhard Langer, Venus Williams and Justin Langer while continuing to write a weekly column on Asian and Australian football for ESPN Soccernet.

In addition, Jason presented major sporting events for ESPN STAR Sports, including three tennis Grand Slams in 2003 and 2004, the 2005_United_States_Grand_Prix, international cricket, rugby, plus the 2006 FIFA World Cup where he was an on-site 'live' reporter in Germany. He also wrote a weekly column called Dasey Direct for Espnstar.com.

In November 2001, Jason left CNN to become the senior news presenter at Asian network ESPN Star Sports, based in Singapore. After hosting the India-focused Sportsline, Jason was the original anchor as SportsCenter Asia was launched in earnest in May 2002 and when SportsCenter India was reshaped as an English-language show in October 2003. With Jason as co-host, SportsCenter Asia was voted Best Sports Programme at the 2003 Asian Television Awards. In 2005, he appeared as a judge on the first Dream Job Asia series, including the final with Pakistan cricket legend Wasim Akram.

After three years in London with the BBC, Jason moved to the U.S. in 1997. After serving as a freelance reporter for BBC World Service and Denver local station, KUSA-TV 9-News (NBC), Jason re-located to Atlanta in early 1999 to take up a job at CNN International. He was initially a news producer/writer, but in May 1999, Jason became the first Australian sports anchor on CNN International's World Sport, broadcasting daily to more than 200 countries, often in partnership with Pedro Pinto. That year, he also made his first forays into digital journalism with a regular column for the CNN_Sports_Illustrated website.

Jason's biggest break came at the end of 1994. As a freelance producer and occasional presenter for BBC World Service Television in London, he was promoted to senior sports anchor on the re-branded BBC World News after a fill-in stint as host. It made him the first Australian newsreader on the global network as part of ‘Newsday’, a breakfast show for Europe, with co-hosts Philip Hayton, Melinda Wittstock and Richard Quest.

In 1987, Jason returned to London where he would base himself for most of the next decade, with his paternal grandmother from Staffordshire. Initially, he freelanced as a producer/reporter for SBS-TV, Fairfax Media, Reuters TV and BBC TV for whom he was an assistant producer on Breakfast Time, contributing to its coverage of Australia's Bicentenary, including producing a back-stage interview with Barry Humphries in London's West End. In January 1989, Jason became a sports producer and reporter for European satellite network Sky News as it launched in Britain. A year later at Sky, he gained his first regular experience in the studio, as a weekend sports presenter.

Towards the end of his four years with the Herald, Jason's personal vacation to New York City in September 1983 coincided with Australia winning sailing's America's Cup. Jason borrowed a blazer and talked his way into the New York Yacht Club before sending back an insider's account to the Sydney Morning Herald on the night the United States lost the America's Cup for the first time after 132 years.

That front-page story from a famous edition of the Herald helped 21-year-old Jason land a job at Australia's Seven Network in Sydney where he worked between 1983 and 1985 as an on-air reporter for Seven News and its nightly 'Willesee' current affairs show. At the end of 1985 after a six-month stint as a researcher for BBC_Nine_O'Clock_News in London, he became a producer and reporter for SBS-TV in Sydney.

The eldest of four brothers, Jason grew up in Sydney where he attended North Sydney Boys High School and was co-editor of the school's magazine. His father was an advertising copywriter and artist, while his mother was a cooking book author and cooking teacher. Jason's first newspaper articles were published in the North_Shore_Times in 1977. From 1978, he became a freelance sports reporter for Australian Associated Press. At the start of 1980, Jason joined The Sydney Morning Herald, Australia's oldest newspaper, as a cadet journalist. In December 1980 at the age of 18, he broke his first major story, securing an exclusive interview with a Soviet defector who jumped ship in Sydney Harbour to seek political asylum.