635 Jason Calacanis on Brooklyn Grit, Big Asks, Angel Investing (Uber, Calm, Robinhood, and More), The Magic of Thinking Big, and St*bbing People in the Face but Never in the Back
This is a OPEN AI summary of the Tim Ferriss Podcast #635- visit www.TinyTim.blog for more AI summaries, or www.Tim.blog for the official Tim Ferriss Podcasts.
In this episode of The Tim Ferriss Show, Tim Ferriss interviews Jason Calacanis, an early investor in over 300 startups and author of the book "Angel." They discuss Jason's work as a scout for Sequoia Capital, his experience hosting two podcasts, and his thoughts on the future of podcasting.
Jason Calacanis talks about how he went from being an unknown to a highly sought-after speaker in a span of a few weeks, attributing it to the success of his book, "The 4-Hour Work Week." Tim Ferriss agrees that this can happen to anyone, citing his own experience of becoming a New York Times bestselling author.
Jason Calacanis was the founder of Silicon Alley Reporter, a magazine about the internet. When the dot com bust happened, he lost everything and ended up selling the magazine to Dow Jones. However, they soon fired him, citing his talent as the reason. After being fired from his job, Jason Calacanis felt rage like he had never felt before. He took the $500,000 severance check and used it to start his own company. Jason Calacanis started calling people up to ask what they were working on after the dot com bust. He was trying to get a sense of where the "pucks" might be going next and stumbled upon some interesting projects. One was a photosharing site called Flickr and
Jason Calacanis is an entrepreneur who was inspired to start his own delivery service, Mercury Club, after observing the culture of bike messengers in New York City. In this excerpt, he talks to Tim Ferriss about his Greek heritage and the meaning of his last name. He also shares a story about his grandfather coming to Ellis Island.
Jason Calacanis is an entrepreneur who came up with the idea for Weblogs, Inc., which quickly became a success. In this interview, he discusses with Tim Ferriss the importance of taking risks, finding good writers, and staying focused despite failures. They also discuss the early days of Weblogs, Inc., when they were hiring writers to produce content for their site. Sean Bonner was one of the first writers they hired, and he quickly became a key contributor to the site. Eventually, Weblogs, Inc. was sold to AOL for $30 million. Jason Calacanis is also a podcaster and event host who believes that events should be designed to maximize community engagement. He reflects on his own childhood experiences as motivation for his work in creating opportunities for people to connect with one another.
Jason Calacanis and Tim Ferriss discuss loyalty, friendships, and the All-In podcast. They talk about how the world gets smaller as you become more successful and how this can make it difficult to go out and socialize. Jason also talks about how the podcast has had a profound impact on his life, including helping him lose 30 pounds.
Jason Calacanis and the team behind the popular podcast This Week in Startups are continuing to produce interesting and entertaining content. They have recently come under fire for some of their opinions, but they continue to stand by their convictions. Jason Calacanis is also in the process of raising a venture capital fund, and he has been successful so far. Tim Ferriss says that the team needs to trust and love each other in order to continue putting on a good show.
In this excerpt, Tim Ferriss and Jason Calacanis debate the importance of open dialogue and debate on controversial topics. Ferriss shares his policy of only discussing such topics if he has access to an expert who can speak credibly on the matter, and then adding in strong disclaimers. This allows for a more level-headed discussion of the topic without getting caught up in the emotion of the situation.
In this conversation, Tim Ferriss and Jason Calacanis discuss the art of moderating conversations. They note that the current political climate has made people more censored in their everyday lives.
Jason Calacanis and Tim Ferriss discuss the Overton window and how it has changed over time to allow for more open discussion of previously taboo topics. They also discuss how podcasts like Bret Easton Ellis' "Less Than Zero" and "American Psycho" are pushing the boundaries of what is considered acceptable to discuss publicly. Jason Calacanis explains that the success of his podcast is due to a combination of factors, including his own experience and expertise, as well as the repetition and consistency of producing new episodes. Tim Ferriss and Jason Calacanis discuss the difference between playing ping pong and tennis. Ferriss argues that playing tennis requires more brain power, and that this is why he has been successful in recent years. In his new book, Jason Calacanis explores the paradox of "catching the car" - that is, achieving success and then having to ask oneself whether or not one is actually happy. For Tim Ferriss, this is a question he's currently grappling with.
Jason Calacanis and Tim Ferriss discuss the benefits of psychedelics in treating mental illness. Calacanis cites Colorado's recent legalization of psychedelic therapy as a sign of progress in this area. Ferriss agrees that psychedelics have great potential in treating mental illness, and shares his own experience with taking Ozempic for the first time.
Jason and Tim agree that it is important to be kind to others and to make the most of every moment.
635 https://tim.blog/2022/11/18/jason-calacanis/
