[9] From 2010-2015, Chiu worked with A Legend Star Entertainment Corp., a company founded by the former Channel [V] Taiwan director, Andy Chang.

[12] His younger brother, Mao Di, was a former member of Choc7, and is currently one of Chiu's co-members in JPM, a mandopop band under Sony Music Taiwan.

When he first entered the entertainment industry, Zhang suggested the name Prince to Chiu because he thought the name was both catchy and easy to remember.

[21] Four months later, on May 25, a second EP titled Summer's First Experience[23] was released along with a photobook compiled with photos taken in Okinawa, as well as a DVD.

During the summer of 2007, Chiu and the other members of Lollipop made their acting debut in the drama Brown Sugar Macchiato,[25] a collaboration with Hey Girl.

[30] On September 26, 2007, Lollipop visited Hong Kong to promote their television soundtrack Brown Sugar Macchiato.

This was their first overseas promotional activity ever since their debut, and a huge fan turnout caused a great commotion at the shopping mall where they were having their autograph session[31][32] At the same year, Lollipop began hosting their own show Lollipop Gyashan (LOLLIPOP哪裡怕)[33] on October 27 until April 19, 2008, when the show stopped airing.

[35] Gyashan entered Mandarin charts in the number one position, outselling F4's album Waiting for You – Await Your Love (在這裡等你) which was released on the same day.

[45] In this album, Chiu wrote and sang the ending song for the series entitled Sorry (對不起 Dui Bu Qi).

[48] In 2009, Lollipop made its first lyric contributions to other artists, which are included in the mini album of the group Choc7,[49] composed of seven members selected from the same show.

Aside from music career, he has also starred on his first film entitled Love (愛到底 - 第六號瀏海) with his brother, Mao Di.

[55] However, at the end of 2009, Chiu has moved away from Lollipop's apartment and is now living with Liao Xiao Jie and Qiu Mao Di.

[57] On September 10, they had their first concert at the Hong Kong Kowloon Bay International Trade and Exhibition Center to promote their single.

[62] They signed a contract under A Legend Star Entertainment Corp., a company founded by former Channel [V] Taiwan director, Andy Chang.

[65][66][67] Moreover, he was also cast in Gloomy Salad Days in 2010, and 33 Gu Shi Guan - Fake Chocolate in 2011 as the male lead, Qiu Ke Li.

With their positive public image and work attitude, youthful joy and personal charm, they became the Guangzhou Asian Games volunteer spokesperson.

[73] In addition with the theme of love, 365 album also emphasized the "Golden Triangle" concept to capture each members' individual firm and confidence and also to represent their strong brotherhood.

[71] Moreover, the track list also includes a solo song for each member,[75] and a collaboration with Kimberley Chen entitled "Internet".