Tim Ferriss - Derek Sivers

1) Derek Sivers shares a scuba diving experience in Iceland where he learned an important lesson about empathy and identity. Although he hated being in the water and wanted to back out, his instructor encouraged him to relax and remember the beauty around him. He completed his training and successfully dived the next day, only to find himself helping a German girl who was panicking underwater. Comforting her the same way his instructor calmed him, Derek was reminded of the empathy and compassion that comes with not letting fear and identity take control.

2) Derek Sivers recounts a situation where he had a panic attack and realized that he had been unfairly categorizing people, like those who suffer from depression or panic attacks. He also realized that involuntary events could impact someone's life, and that "categories" like hero rescuer or millionaire are also involuntary. Derek is wary of labels, recognizing their fragile and limiting nature, and advises care when applying them to yourself. He also warns against forming an identity or assuming a label too easily, citing people who read stoicism and now see themselves as stoics as an example.

3) Sivers discusses the idea of identity and embracing the fact that identities can change over time. He explains how he used to call himself an entrepreneur until he realized that his identity had expired, and he needed to actively do something to keep the title. Sivers suggests using a people compass to discover one's true values and admits that his heroes are authors, which helped him realize he was more of an author at heart than an entrepreneur. He shares the importance of loving your customers and serving them to achieve emotional fulfillment, which is the ultimate goal.

4) Derek emphasizes that in choosing a business, it's not just about finding a market that's on the rise, but it's also about asking yourself if you are happy serving the customers in that market. He believes that setting up a business to serve people that you love being around will make you much happier, even if it makes less money. He shares about an idea he has regarding 100 Year Hosting Legacy Personal Websites, which he cares about deeply and would do as volunteer work even if there is no pay. He also touches on the topic of tech independence and cybersecurity, which he wrote about in his diary after a conversation with the interviewer.

5) Derek on Tech Independence and why he chooses not to use the cloud for personal data backups. Sivers emphasizes the value of spending a few hours learning to do things yourself, such as setting up a private server at home, to gain better security and privacy, among other benefits. He also touches on the risks of relying on the cloud, such as accounts being hacked or data being lost due to accidental deletion or account merges, and how having Tech Independence can give you more control and flexibility over your personal data.

6) Sivers discusses the three options for setting up a private server: using a cloud compute service like vulture.com for $ 5/month,searching for cheap dedicated servers on the web, or finding an old used Lenovo ThinkPad from the T400 series on a used market place. He recommends using anoperating system called openbsd, which is simple and secure, and generating a private SSH key so that the only way to log into the server is by using theprivate key from your computer. By editing your firewall to only allow Port 22 for SSH, your server is super secure and can only be accessed by you.

7) Derek talks about the importance of using public and private keys for encryption, and how it will become more prevalent as quantum computing improves. He also recommends getting a domain name from non-affiliate sites like bookmyname.com, netim.com, or porkbun.com. He encourages non-technical people to try setting up a server and shares a simple method to set up a cardDAV or calDAV server for syncing contacts and calendars. Derek also shares a story about his son playing baseball for the first time.

8) Derek discusses his approach to server setup, website creation, and email independence. He recommends having servers in different locations and regularly backing up data across them, along with creating a simple HTML website instead of relying on complex services like WordPress. Additionally, he stresses the importance of using your own domain name for email, with options such as mailbox.org and fastmail.com for hosting. By taking control over these technical aspects, individuals can achieve greater independence and ensure their online presence is truly their own.

9) Sivers responds to potential concerns from people who may be hesitant to move their email off of larger, more established platforms like Google. He reminds listeners that businesses can and do fail, so it's important to have backups in place. By having your own domain name and remote server, you have the ability to easily route your email to another service if needed. Sivers recommends starting with baby steps, like owning your own domain name and switching email to a third-party provider before moving onto more advanced server setups. He also suggests using a service like Mailgun for outgoing email to ensure deliverability.

10) Derek recounts his experience with Shopify and Rails. He initially learned the Ruby programming language, and upon hearing about a web framework being developed with it, he reached out to David in Denmark, who was working on Rails. However, it was Toby, who offered to show him Rails for $100 over the phone, that got him into it. Derek later finds out that Toby was the founder of Shopify, which he didn't initially introduce to Tim when asked, but was thrilled to learn about its success later on.

11) Derek Sivers talks about the concept of "satisficing" and how it has shaped his life decisions. He explains how research shows that people who aim for the best possible option tend to feel worse about their choices compared to those who settle for a "good enough" option. Derek believes that satisficing is a superpower and that people should focus their energy on improving what is fun for them rather than leaving everything as it is. He also discusses how nobody cares about what you are not good at and that it is unnecessary to optimize everything in life.

12) Derek shares his approach to decision-making, emphasizing the importance of making reversible or trivial decisions quickly, and moving on from unresolved decisions in order to avoid the weight of unfinished projects. He also discusses his philosophy of "useful not true" skepticism, which involves questioning and analyzing beliefs and ideas, recognizing that very little is objectively true, and accepting individual ideas rather than adhering to a particular ideology. He encourages listeners to recognize the liberating power of skepticism, and to embrace the idea that beliefs are placebos that can be changed.

13) Derek explains the importance of understanding why people say certain things and how to dispel negative interpretations or projections. He uses the example of split brain patients who make up reasons why they do certain things without realizing they are making it up. Sivers suggests that no beliefs are true and that choosing a certain belief that helps you be who you want to be can be empowering. He concludes that one will find evidence to support their belief if they choose to believe in something.

14) Derek discusses a liberating moment in his life where he realized that he was liberated from authority and judgment as long as he didn't break the law. He uses an experience with a man's fiance to illustrate this point and acknowledges that societal norms shape our perception of right and wrong, but we can choose to agree or disagree with them. He mentions the idea of moral relativism and defers to Sam Harris' "The Moral Landscape" for a better understanding of objective moral judgment based on individual well-being.

15) Derek discusses the benefits of having a consistent moral compass, particularly in secular society where decision fatigue can be a real problem. He mentions that he is sometimes envious of those who have a religious moral framework because their rules can narrow down the choices they have to make. Sivers suggests that having a sense of what is right or wrong can help in decision-making and that he has a personal philosophy of doing things for the greater good, even if it doesn't necessarily serve him personally. However, he warns against subscribing to an ideology to the point of tribalism, pointing out how this can also lead to decision fatigue and possibly even harm.

16) Sivers shares his encounter with a German man on a plane who dismissed Tim Ferriss's book, The 4-Hour Work Week, as trash simply because of one thing he disagreed with. Sivers argues that this kind of reductionism and ism-mentality is problematic because it simplifies reality,and people become all in on an ideology rather than taking ideas piecemeal. He suggests being open-minded and taking ideas individually, regardless of whether they come from someone we like or dislike. Moreover, he emphasizes the importance of avoiding isms and ideologies to cultivate a clearer, stronger, and more independent way of thinking.

17) Sivers talks about how he discovered Stoicism and Cognitive Behavioral Therapy (CBT) and how they overlap with each other. He explains how he has been practicing a form of CBT for decades, which involves writing in his diary and doubting everything he writes, thinks, or says. According to Sivers, it is healthier to try different approaches rather than blindly following one philosophy or identity to find what works best for oneself. The conclusion of this section is that one can change their beliefs by questioning them and trying on different ideas like trying on a suit.

18) Derek discusses how to translate a new belief into durable behavioral change. He recommends writing in a diary about the empowering belief you want to have and then stacking up evidence to support it. He also suggests talking with friends about it, taking baby steps or giant leaps to put it into action, and acting as if you already believe it. Derek shares his personal experience of renouncing his US citizenship in 2011 as away of challenging himself to go forward and not go back, but admits it was one of his biggest mistakes in life because it made it hard to visit family and friends in the US.

19) Sivers shares the story of how he decided to sell his company, and how his friend challenged his mindset and encouraged him to understand that he didn't have to do anything he didn't want to. Sivers emphasizes the importance of personal growth and making choices that align with our values. He also gives advice on how to approach mentors by summarizing the problem, predicting their responses, and internalizing them to come up with a clear answer before reaching out to them. Sivers admits that he hasn't talked to his mentors in years, and suggests that people should focus on summarizing situations and imagining what their mentors would say as a way to mentor themselves.

20) Derek Sivers discusses the concept of games that people play in life, beyond the basic needs of shelter and food. He talks about how he used to play the game of being successful, famous, and rich in the music industry until he won that game by his standards. He compares winning the game to winning a game of Settlers of Catan or Monopoly and how you usually stop playing after you win. Derek then talks about the addictive nature of playing video games, using the example of Stardew Valley, and how the temptation to keep playing even when the rewards are done is the definition of addiction.

21) Sivers talks about the book "How to Get Rich" by Felix Dennis, which advises people to retire early and focus on creative pursuits. Derek Sivers took inspiration from this book and decided to quit the game after selling CD Baby and to focus on other passions. He suggests that people should consider quitting while they are ahead, rather than following the inner compass that tells them to keep playing a game they are good at.

22) Sivers discuss Sivers' personality traits, including his seemingly unemotional and low need for external validation nature. The two also explore the concept of success, with Sivers stating that success is hyper-personal and simply achieving what one sets out to do. The conversation then shifts to fame and how it fits into his personal definition of success, with Sivers attributing his teenage desire for fame to competitiveness and his desire to be heard. Ferriss notes that Sivers is an interesting performer because he appears to have no need for validation, yet he is still a good performer, which is uncommon.

23) Sivers talks about the origins of his journey as a musician and entrepreneur. He explains how he accidentally started CD Baby, and how it changed his perspective on attention and validation, leading him to no longer need them. He also discusses the different types of people when it comes to games in life: satisficers, maximizers, and those who win but continue playing the same game without knowing what else to do. Derek believes that the latter need to be physically shaken out of their habits and placed into a different environment to see that there's a bigger world out there.

24) Derek talks about the concept of impressiveness, using Genghis Khan and Alexander as examples, and how he's become less concerned with it over time, realizing that it's an external measure of success. He also touches on the idea of being a maximizer versus satisficer, saying that he's learned to be the latter because he's felt the pain of too many options and too much time spent making decisions. He gives an example of buying a car in two hours after reading The Paradox of Choice and internalizing the concept of "good enough."

25) Derek talks about his difficulty in deciding where to live after selling his company and feeling completely free to live anywhere he wanted. He spent an excessive amount of time researching and reading about various countries he had never visited and learning about their Naturalization laws, becoming a resident, and pros and cons of living in each place. Derek shares his personal experience of over-optimizing and being paralyzed by too many choices, which he later realized was an extreme case or an edge case that applies to everyone in some way, no matter where they are on the socioeconomic spectrum. He then goes on to discuss the importance of designing for edge cases, which, in turn, benefits everyone.

26) Tim and Derek discuss the common question of what advice one would give to their younger self, which is often rephrased as what advice would you give to someone who wants to be where you are. Derek points out that despite the question being widespread, there are too many context-specific factors at play, which means that an answer that could have extensive positive outcomes for one person, could result in the opposite effect for another. It is worth mentioning that suggesting the type of advice Derek could have provided wouldn't work for everyone, particularly those who are motivated by a particular misconception, and therefore, the response could be counterproductive.