In the podcast recording of episode 163 of “We Hired a Sitter for This,” hosts Patrick Holbert and Gastor Almonte engage in a lively discussion covering a range of topics. They kick off with personal updates, including Gastor’s memorable experience at the World Series with his father, celebrating the latter’s recovery from chemotherapy, making for a heartfelt conversation about baseball as a familial bond. The duo then shifts gears to fashion, where they explore Gastor’s extensive hat collection and care routine, contrasting it with Patrick’s minimalist style, while also brainstorming a stand-up fashion challenge web series. The discussion evolves into the impact of parenting on children’s futures, touching on Gastor’s children’s educational paths and Patrick’s observations on sports opportunities for urban youth. They reflect on career choices, with Gastor contemplating balancing comedy with traditional employment and Patrick discussing long-term financial security in the arts. The podcast concludes with discussions about stand-up performance styles and the influence of spouses in their comedy careers. Action items include exploring co-headlining shows in Wisconsin and Chicago, following up on fundraising MC opportunities, and focusing on job searches in entertainment or teaching fields.