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The Tim Ferriss Show

#682: Bill Gurley Interviews Tim Ferriss — Reflecting on 20+ Years of Life and Business Experiments

Wed Jul 19 2023
Compliance AutomationSleep OptimizationEntrepreneurshipAngel InvestingCareer GrowthContent CreationPodcasting StrategiesPodcasting IndustryPersonal InsightsPersonal Growth


This episode of The Tim Ferriss Show features interviews with Bill Gurley and Tim Ferriss himself. It covers topics such as entrepreneurship, tech, podcasting, angel investing, career growth, content creation, podcasting strategies, the podcasting industry, personal insights, and personal growth. Key takeaways include the importance of compliance automation platforms like Secure Frame, the benefits of using the Pod Cover by 8 Sleep for optimal sleep, Tim Ferriss's journey from Princeton to angel investing, tips for successful podcasting, insights into the podcasting industry, Tim Ferriss's personal book recommendations and failures, and the significance of personal growth and effective communication.


Compliance Automation Platform

Secure Frame is an industry-leading compliance automation platform that helps businesses achieve compliance with security and privacy frameworks.

Optimal Sleep

The Pod Cover by 8 Sleep adjusts the temperature of your sleeping environment for optimal sleep.

Entrepreneurship and Tech

Bill Gurley, a legendary investor, shares insights on entrepreneurship and working with companies like Grubhub, Uber, and Zillow.

Tim Ferriss's Journey

Tim Ferriss's journey from Princeton to angel investing is filled with valuable lessons on reaching decision makers, storytelling, and intentional decision-making.

Career Growth and Content Creation

Tips for career growth include moving to different locations seasonally and focusing on continuous learning. Tim Ferriss also shares insights on content creation and the importance of producing evergreen content.

Podcasting Strategies

Tim Ferriss provides valuable insights on podcasting strategies, including preparation techniques, exploring unexplored topics, and seeking input from guests and acquaintances.

Podcasting Industry

Insights into the podcasting industry include recommendations for learning about podcasting, the success factors behind popular podcasts, and the growth of platforms like Spotify.

Personal Insights

Tim Ferriss shares personal insights on book recommendations, favorite failures, personal growth habits, and the importance of responsible thinking.

Personal Growth and Communication

Insights on personal growth include the benefits of waiting and doing nothing, studying non-violent communication, and effective communication techniques.


  1. Introduction
  2. Tim Ferriss's Journey
  3. Angel Investing and Decision-Making
  4. Career Growth and Content Creation
  5. Podcasting Journey and Success
  6. Keys to Success in Podcasting
  7. Podcasting Strategies and Recommendations
  8. Podcasting Industry and Insights
  9. Tim Ferriss's Personal Insights
  10. Personal Growth and Communication


00:00 - 07:35

  • Secure Frame is an industry-leading compliance automation platform that helps businesses achieve compliance with security and privacy frameworks.
  • 8 Sleep offers a device called the Pod Cover that adjusts the temperature of your sleeping environment for optimal sleep.
  • The Tim Ferriss Show features a special episode where Bill Gurley interviews Tim Ferriss about his lessons learned in entrepreneurship, tech, and podcasting.
  • Bill Gurley is a legendary investor who has worked with companies like Grubhub, Uber, and Zillow.
  • Tim Ferriss's first appearance at South by Southwest in 2007 kickstarted his career as an author and speaker.

Tim Ferriss's Journey

07:12 - 14:16

  • Graduated from Princeton in 2000 with a degree in East Asian Studies
  • Launched podcast in 2014 after years of various experiences
  • Moved to Northern California to be part of the tech industry
  • Worked in data storage and learned about selling
  • Started a sports nutrition company while guest lecturing at Princeton
  • Sold the startup around 2009 after six years of building it
  • Key takeaways from the startup include reaching decision makers by calling outside business hours, doing homework when talking to technical people, and the value of storytelling
  • Startup life wasn't working due to flattened learning curve and not wanting to become a manager
  • The notes from a class became the basis for 'The Four-Hour Workweek'
  • 'The Four-Hour Workweek' opened doors for angel investing and permission to write more books
  • Made intentional decisions when choosing different book topics and avoiding being pigeonholed

Angel Investing and Decision-Making

13:48 - 20:24

  • Tim Ferriss discusses his decision-making process for writing books and angel investing.
  • He made a significant advance from publishers for his book 'The 4-Hour Workweek' which helped fund his angel investments.
  • Tim started angel investing about 10 months after the release of his book.
  • He invested in companies like Uber, Shopify, Duolingo, Facebook, and Twitter.
  • His rule set for investing was to choose companies that addressed a personal problem he understood and could recommend to others.
  • Tim viewed angel investing as a real-world MBA, focusing on the skills, knowledge, and relationships he would gain rather than expecting immediate financial returns.
  • He emphasized the importance of choosing founders he enjoyed working with and who passed the 'beer test'.
  • Tim believes in looking at the antecedents or previous decisions that led to successful outcomes rather than just focusing on well-known success stories.
  • He moved to San Francisco to increase serendipity and take advantage of in-person interactions.

Career Growth and Content Creation

20:06 - 27:32

  • Choosing to move to different locations seasonally can be valuable for career growth.
  • Angel investing has become more difficult due to increased competition and noise.
  • The majority of fast learning happens in the first few years of doing something.
  • The speaker is attracted to fiction, animation, AI, and other creative pursuits.
  • The blog was started before the book and podcast as a way to reach bloggers.
  • Email collection began in 2007 but wasn't utilized until around 2014.
  • Using WordPress allows for flexibility in migrating content if needed.
  • Producing evergreen content is preferred over content with an expiration date.
  • The speaker considers themselves a writer and interviewer rather than a content creator.

Podcasting Journey and Success

27:03 - 34:05

  • After being burned out from writing a book, Tim Ferriss decided to try podcasting as a graceful exit.
  • He started with the expectation of doing six or ten episodes, even if it failed, to improve his interviewing skills and build relationships.
  • Tim studied successful podcasters like Dan Carlin and learned not to follow dogmatic rules but instead test and experiment.
  • He hired a senior researcher from Inside the Actor's Studio to analyze his transcripts and improve his interviewing techniques.
  • Tim believes everyone should record a podcast to become a clearer and more concise thinker.
  • The key to Tim's success as a podcaster was choosing a format that he could persist in doing and keeping the show broad enough to explore various interests.

Keys to Success in Podcasting

33:35 - 40:40

  • Endurance is a competitive advantage in establishing a business.
  • Focusing on improving skills and craft is important.
  • Direct communication with the audience is essential.
  • Email and podcasting are effective forms of direct communication.
  • Short, easily digestible formats like newsletters reinforce podcasts.
  • Risk management is important when relying on social media platforms.
  • Staying lean and minimizing overhead can be beneficial for some businesses.
  • Defining outcomes, eliminating non-essential tasks, and automating processes are key to efficiency.

Podcasting Strategies and Recommendations

40:14 - 46:35

  • The podcast doesn't need a large team or video because it would increase infrastructure and limit location flexibility.
  • Preparation involves writing a blog post about not reading new books, looking at long-form video and audio, and identifying neglected topics.
  • Before recording, there is a brief warm-up conversation, assurance of final cut for guests, and discussion of what would make the interview a success.
  • To explore unexplored topics, the host volunteers personal information first to encourage vulnerability from guests.
  • The host also seeks input from friends and acquaintances for questions or topics to discuss with guests.
  • Many guests are recommended by other guests.
  • Podcasters like Guy Raz and Joe Rogan are respected for their unique approaches.

Podcasting Industry and Insights

46:17 - 53:14

  • The Law of Category chapter in the 22 Immutable Laws of Marketing is recommended for learning about podcasting
  • Experimenting with a brand new format and combining entertainment and in-depth interviews helped popularize podcasts
  • Lex Friedman, Patrick O'Shaughnessy, and other interviewers are praised for their podcasting skills
  • Spotify's strategic decision to acquire talent and fold in existing audiences was smart
  • Spotify's growth as a podcast player has tripled or quadrupled in recent years
  • Twitter is useful for connecting with podcast guests through DMs
  • LinkedIn may become a powerful platform for broadcasting content
  • Having a focal point like an email newsletter or focusing on improving podcast quality is important to succeed in the podcasting world

Tim Ferriss's Personal Insights

52:57 - 59:59

  • Tim Ferris wrote a book called 'Tribramentors' with a list of questions for different people.
  • The first question is about the books they have gifted the most.
  • The guest mentions 'Complexity' and 'Mr. China' as his choices.
  • The host mentions 'Moral Letters to Lucilius' and 'Awareness' as his choices.
  • The second question is about the purchase of $100 or less that has positively impacted their life in the last six months.
  • The guest talks about amazing nail clippers and getting rid of skeek gloves due to Ray Nods disease.
  • The host mentions following Kevin Kelly's advice on getting high-quality versions of everyday items.
  • The third question is about their favorite failure or failure that set them up for success.
  • The guest talks about experiencing defeat in math competitions, which gave him perspective.
  • The host mentions burning out while writing a book and not being able to do animal testing in neuroscience lab, leading to language studies focus instead.
  • 'Do whatever gives you the most energy because energy drives everything else,' says the host.
  • They discuss being responsible for one's own thinking and not believing everything one thinks.
  • 'Strong opinions loosely held' is mentioned as a famous saying related to this topic.
  • They talk about attending Blog Expo and meeting influential bloggers, which had a significant impact on their work week book.
  • 'Waiting for problems to go away' is mentioned as a habit that has improved their life in the last five years.

Personal Growth and Communication

59:31 - 1:05:33

  • Waiting and doing nothing has helped solve many problems for the speaker.
  • Studying non-violent communication has improved the speaker's ability to navigate conflict.
  • If someone is dysregulated, they can take a breather and postpone a conversation until they are in a better state.
  • Tim Ferriss promotes his newsletter called 5 Bullet Friday, which shares cool things he has discovered throughout the week.
  • The Pod Cover by 8 Sleep helps regulate temperature during sleep, improving sleep quality.
  • Secure Frame offers an automation platform to simplify and streamline compliance with security and privacy standards.