Jesse sits down with entrepreneur and finance content creator, Nate Kennedy. The two discuss why schools don't teach finances, Jesse's investment journey, credit cards, renting vs owning, F You money, and much more!

Jesse sits down with content creator and video host for CBC's Street Cents, Mercedes Gaztambide. The two discuss the end of Jesse's Toronto Man character, Mercedes' time with BlogTO, getting recognized by strangers, why our generation is terrible with money, and much more!

Jesse sits down with therapist, relationship coach, and founder of the Men's Mental Health Institute, Christie Chan. The two discuss men's mental health, finding the right therapist, modern dating gaps, social media's effect on dating, raising men's standards, and much more!

Jesse sits down with food content creator, Clement Leung AKA Ramen Guy, who has over 4 million followers across all platforms! The two discuss starting on social media, why Clement decided to do ramen, getting brand deals, food around the world, how to stay healthy while creating food content, and much more!

Jesse sits down with his mom, Nihal, for a special Mother's Day edition of the podcast! The two discuss coming to Canada, Egypt vs Canada, Jesse as a kid, her thoughts on Jesse's lifestyle and girlfriend, and more!

Jesse sits down with hockey and comedy content creator, Erik Nagy. The two discuss putting value on views, exhaustion from being on social media, the Toronto Maple Leafs, using internet clout in the real world, and much more!

Jesse sits down with content creator and CEO of service, Max Farber. The two discuss bad jobs vs bad people, their worst jobs ever, cold calling customers, the reality of working in social media, and much more!

Jesse sits down with content creator, Tessa Conway! The two discuss the importance of building a relationship with your audience, remaining always grateful, staying positive, creator's guilt and much more!

Jesse sits down with Much Music VJ and former classmate, Georgia Kolev. The two discuss the new generation of Much Music, Georgia's best and most memorable celebrity interviews, the current state of the music industry, and more!

Jesse sits down with Canadian sports television personality, Cabbie Richards. The two discuss the struggle of securing an interview in the current sports climate, what Cabbie is most proud of, Cabbie's relationship with the late Kobe Bryant, and much more!

In the first episode of the Listen Listen Podcast, Jesse sits down with his childhood friend of almost 20 years, Anania. The two discuss losing friends in their 20s, the good and bad of social media, UFC 300 predictions, and more!