Since 2014, he has hosted the award winning The Jake Sasseville Show, a podcast having an audience of one million listeners and called "the intersection of Culture and Consciousness" by the Huffington Post.

He dropped out of college to pursue his career full time, becoming the youngest host in recorded late night TV history after Jimmy Kimmel at age 22.

Guests have included actor Rainn Wilson of The Office, musician and activist Wyclef Jean, the President of Zambia, Kenneth Kaunda, Al Capone's grandson Chris, and Congressman Dennis Kucinich.

[19] From 2010-2011, he was the executive producer, emcee and co-owner of several music tours, featuring Kanye West, OneRepublic, Guster, J. Cole Fabolous and Brett Dennen.

[21] On September 16, 2014, Sasseville launched "The Jake Sasseville Show", a podcast, and the show quickly built an audience of one million listeners thanks in part to initial guests like Yvette Noel-Schure (Beyonce's publicist),[22] presidents of Fortune 500 companies[23] and NBA teams,[24] professional sports athletes, Grammy winning musicians and best-selling authors.

[27] On another occasion, Sasseville broke the world record for largest drum ensemble on Pringles Xtreme cans to win the affinity of the brand.

After moving to Maui from his grandmother's basement and becoming friends with Ram Dass[32] and Shep Gordon,[33] Sasseville became interested in the world of transformation as he saw the trend of health and wellness.

The pair in 2017 notoriously raised $3.5 million in five Facebook posts,[36] making a dent in the social impact world of investing by gathering 38 investors from 19 countries for Imiloa's formation.