Bobby Lee on Relationships, Making Millions, & Not Giving A F**K

Added: Aug 21, 2023

The podcast begins with Bobby Lee jokingly describing a hypothetical scenario involving a woman who is seven feet six inches tall and has a head shaped like a wrecking ball. He humorously contemplates the idea of being in a relationship with her and explores the dynamics of such a unique situation. The conversation then takes a turn towards mythological creatures, with Bobby expressing his interest in them and his love for fantasy and sci-fi. The hosts ask Bobby if he would date a Minotaur, a creature with a bull body and human legs. Bobby admits that he doesn't know much about mythological creatures but expresses his openness to the idea. The hosts then mention other mythological creatures like centaurs and satyrs, to which Bobby responds with curiosity and humor. The conversation shifts towards the current state of comedy and the impact of social restrictions on comedic expression. Bobby acknowledges the challenges faced by comedians in today's society, where people are quick to take offense and demand apologies for past statements. He shares his own experience of getting in trouble for certain remarks and discusses the need to adapt to the changing landscape of comedy. Bobby reflects on the importance of letting go of things that can be taken away and not living in fear. He mentions the consequences of cancel culture and the tendency for people to want to destroy someone's life over a difference of opinion. Despite the challenges, Bobby remains grateful for his career and the opportunities he has had in comedy. The hosts ask Bobby about his thoughts on late-night talk show hosts like Jimmy Fallon and Seth Meyers. Bobby admits that he hasn't watched much of their shows and prefers comedians like Jay Leno. He criticizes the current state of late-night television, describing it as cookie-cutter and lacking in humor. The conversation takes a lighthearted turn as the hosts ask Bobby about his comedic process. Bobby explains that he doesn't consciously come up with jokes but rather speaks off the cuff, making things up as he goes along. He emphasizes the importance of showing up and just doing it, rather than living in fear or overthinking. Bobby continues by talking about how he deals with fear. He admits that he has fears like everyone else, but instead of letting fear hold him back, he pushes through and takes action. He believes that this willingness to face his fears and take risks has been one of the few things he has done right in his life. By putting one foot in front of the other and saying "f**k it, I'm doing it," he has gained confidence and overcome his fear of authority and rejection. He explains that doing stand-up comedy has played a significant role in building his confidence. The experience of performing in front of an audience and facing the possibility of not getting laughs has taught him that rejection and negative opinions don't define him. He has learned that a bad night or rejection doesn't mean anything and doesn't have the power to destroy him. The conversation then takes a more lighthearted turn as Bobby discusses his shamelessness and intrusive thoughts. He shares some of his unconventional and sometimes inappropriate thoughts, such as wondering what it would be like to have sex with fictional characters or making fun of people with physical deformities. While his thoughts may be considered wrong or offensive, he doesn't see them that way and questions why they should be considered bad. The host questions Bobby about his shamelessness and fearlessness in expressing his thoughts, to which Bobby admits that he does have fear and shame but still chooses to express himself regardless. He believes that his thoughts and jokes are harmless and that people's opinions shouldn't hold so much power over him. The conversation then shifts to Bobby's financial situation and work ethic. Bobby reveals that he doesn't know how much money he makes or what his expenses are. He has a money manager who takes care of his finances, and he trusts him to make the right decisions. Bobby doesn't worry about money because he knows he can go a long time without working and still be fine. He believes that it's important to live a life where he doesn't constantly worry about his bank account. The hosts express surprise at Bobby's lack of concern about his finances. Bobby explains that he used to worry about money when he had very little, but now that he makes a decent income, he doesn't feel the need to constantly check his bank account. He trusts his money manager to handle his investments and make smart financial decisions. The conversation concludes with a discussion about being poor and the fear of going back to that state. Bobby shares that he has been in despair at various points in his career, but he has always found a way to adapt and overcome. He acknowledges that if things were to go really bad, he could always go back to living with his mom, but he finds that thought depressing.