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

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Jul 19, 2023

A legendary investor interviews a well-known entrepreneur, diving deep into two decades of lessons in technology, business, and podcasting. They discuss the importance of patience, effective communication, and personal growth. Listeners explore the journey from academia to tech, the evolution of a successful podcast, and the power of direct audience engagement through newsletters. Insights on the lean podcast landscape and automation for business compliance highlight innovative strategies. This conversation reveals the transformative power of new beliefs and creative pursuits.

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ADVICE

Reaching Decision-Makers and Technical Selling

Call decision-makers outside business hours.
Do your homework and understand technical details when selling to technical people.

ANECDOTE

Transitioning from Startup to Writing and Investing

Tim Ferriss sold his sports nutrition company after the learning curve flattened.
He transitioned to writing and angel investing.

ADVICE

Choosing Projects for Maximum Optionality

Choose projects that open more doors, rather than specializing too early.
Avoid getting stuck in a niche by exploring diverse fields.

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The 4 Hour Workweek

Timothy Ferriss

In 'The 4-Hour Workweek', Timothy Ferriss presents a step-by-step guide to 'lifestyle design', encouraging readers to question the traditional notion of retirement and instead create a lifestyle that prioritizes freedom, adventure, and personal growth. The book teaches how to outsource life tasks, automate income, and eliminate unnecessary work using principles like the 80/20 rule and Parkinson’s Law. Ferriss shares his personal journey from a corporate workaholic to a location-independent entrepreneur and provides practical tips and case studies to help readers achieve similar results. The book emphasizes the importance of focusing on high-value activities, taking 'mini-retirements', and living life to the fullest in the present rather than deferring enjoyment until retirement.

Letters from a Stoic

Seneca

Seneca's "Letters from a Stoic" comprises a collection of personal letters offering practical advice on living a virtuous life according to Stoic principles. Written to Lucilius, a friend and student, the letters cover a wide range of topics, including dealing with adversity, managing emotions, and finding inner peace. Seneca's writing style is engaging and relatable, making complex philosophical concepts accessible to a wider audience. The letters offer timeless wisdom on self-improvement and ethical living. They remain a valuable resource for anyone seeking guidance on navigating life's challenges.

Awareness

a de Mello spirituality conference in his own words

Anthony de Mello

In 'Awareness', Anthony de Mello combines Christian spirituality, Buddhist parables, Hindu breathing exercises, and psychological insight to challenge readers to wake up from the go-go-go world of illusion. The book, composed of short chapters and lectures, encourages readers to become aware of their thoughts, actions, and motivations. De Mello argues that true happiness and freedom come from dropping illusions and living in the present, free from the constructs of culture, conditioning, and fear. He emphasizes the need to observe oneself, understand negative feelings, and practice detachment to achieve a more authentic and fulfilling life[1][3][5].

Brought to you by Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating, Secureframe automated security and privacy compliance platform, and AG1 all-in-one nutritional supplement.

Welcome to another episode of The Tim Ferriss Show, where it is usually my job to deconstruct world-class performers to tease out the routines, habits, et cetera that you can apply to your own lives.

This is a special episode and a turning of the tables. This time, legendary investor Bill Gurley interviews me, and the recording is from earlier this year at SXSW in Austin, TX. The conversation explores some of my lessons learned and favorite findings over the last two decades in areas like entrepreneurship, tech, and podcasting. I throw in some favorite books and other spice to keep things interesting.

Bill Gurley (@bgurley) has spent more than 20 years as a general partner at Benchmark. Before entering the venture-capital business, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at Credit Suisse First Boston. Over his venture career, he has worked with such companies as GrubHub, Nextdoor, OpenTable, Stitch Fix, Uber, and Zillow.

For more takeaways from his incredible investing career, you can find my interview with Bill at tim.blog/billgurley.

As a side note, my 2007 SXSW speech that I mention in the interview is what started it all, in many senses. It’s what put my first book, The 4-Hour Workweek, on the radar of influential bloggers and bigger media outlets, ultimately landing it on The New York Times Best Sellers list, where it stayed, more or less, for the next seven years. It’s been a wild ride.

You can hear that 2007 presentation at tim.blog/sxsw.

One last thing: Hugh Forrest, if you’re listening, thank you again for giving me a shot way back in the day!

Please enjoy!

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[06:32] From Princeton to podcasting.

[07:39] How a disenchanted entrepreneur became a reluctant author.

[14:22] Angel investing and The 4-Hour Body.

[16:40] Investing rulesets and takeaways.

[19:09] How a choice location maximizes serendipity.

[20:42] Why did I back away from angel investing?

[22:28] Entering the blogosphere.

[27:02] Why podcasting?

[28:33] Early and enduring lessons for improving the craft.

[31:37] What makes a successful podcaster?

[34:57] The power of direct communication with one's audience.

[38:48] Leveraging a lean infrastructure.