April 16, 2024 • 1hr 26min

Tim Ferriss - Curating Curiosities - [Invest Like the Best, EP.369]

Invest Like the Best with Patrick O'Shaughnessy

Tim Ferriss is a writer, podcaster, and investor best known for his bestselling books like "The 4-Hour Workweek" and his popular podcast "The Tim Ferriss Show". He started the podcast in 2014 as an experiment and it has since become one of the biggest podcasts in the world, recently crossing 1 billion downloads. In this conversation with Patrick O'Shaughnessy, Ferriss reflects on nearly 10 years of podcasting, his approach to learning and teaching, and his thoughts on fame, money, and finding meaning.

0:00

-0:00

Key Takeaways

Tim Ferriss started his podcast in 2014 as an experiment to develop skills and deepen relationships, with no intention of it becoming a business
The podcast has since crossed 1 billion downloads and become a successful business, but Ferriss is careful not to let business incentives compromise his original reasons for podcasting
Ferriss sees himself primarily as a teacher and uses a framework called DSSS (Deconstruct, Select, Sequence, Stakes) for learning and teaching new skills efficiently
He values constraints and experiments to find better ways of doing things, often going against conventional wisdom
Fame, money and power can be corrosive if not managed carefully. Ferriss tries to focus on impact and meaning rather than these external markers of success
Energy is the most precious non-renewable resource to guard, even more so than time. Ferriss recommends paying attention to your body's responses to guide decision-making
Some of Ferriss' proudest work has involved sharing difficult personal experiences like suicidal thoughts and childhood abuse, which have helped many others

Introduction

Tim Ferriss is a writer, podcaster, and investor best known for his bestselling books like "The 4-Hour Workweek" and his popular podcast "The Tim Ferriss Show". He started the podcast in 2014 as an experiment and it has since become one of the biggest podcasts in the world, recently crossing 1 billion downloads. In this conversation with Patrick O'Shaughnessy, Ferriss reflects on nearly 10 years of podcasting, his approach to learning and teaching, and his thoughts on fame, money, and finding meaning.

Topics Discussed

The Evolution of Podcasting with Tim Ferriss (3:02)

Ferriss explains that he started his podcast in 2014 purely as an experiment to develop skills like asking good questions and removing verbal tics. He committed to just 6-10 episodes initially with no intention of it becoming a business. The podcast industry was very different then:

Podcasting as a business "wasn't really a thing" in 2014
Ferriss saw it as "cross-training" for his non-fiction book writing
It allowed him to deepen relationships with friends by interviewing them

Over time, the podcast took on a life of its own and became a business. Ferriss notes that this added complexity can sometimes work against the original reasons for doing something. He has become more aware of how business incentives can subtly influence decisions.

Crafting Meaningful Conversations (9:56)

Ferriss shares some key principles for having great conversations:

Ask basic follow-up questions to get beyond people's prepared talking points
Let silence do the work - don't rush to fill pauses
Do pre-interview preparation to find unique angles and make guests comfortable
Start with questions that show you've done deep research to get guests off autopilot

He emphasizes that interviewing is a learned skill that can be developed through practice and study.

What Makes Tim Feel The Most Alive (13:26)

When asked what creative endeavor has made him feel most alive, Ferriss points to podcasting:

The improvisational nature of conversations is energizing
With the right preparation and guest, he can reliably enter a flow state
Even as an introvert, a great 2-3 hour conversation leaves him energized for hours after

Who Tim Considers To Be His Mentors (24:06)

Ferriss discusses some key mentors who have shaped him:

Ed Zschau - Former professor who invited Ferriss to speak to his class, leading to his first book
John Buxton - High school wrestling coach who pushed students to excel

He notes that most of his impactful mentors have had a "tough love" style that pushed him out of his comfort zone.

The Ingredients Of A World Class Performance (29:06)

Reflecting on the many high performers he's interviewed, Ferriss observes:

World-class performance looks different across fields - some require early specialization, others benefit from being a generalist
He's particularly interested in people who achieve excellence in a second field or later in life
Many top tech CEOs excel by being in the top 20% of multiple complementary skills rather than being the absolute best at one thing

The Business Side of Podcasting (31:06)

Ferriss shares some insights on the business of podcasting:

He intentionally designed his operation to have constraints, like keeping a small team
Unconventional policies like requiring upfront payment from sponsors have worked well
He charges premium rates ($60 CPM vs $10-15 industry standard) but is very selective about sponsors
His ideal is sponsors who stick around for 5-10 years, so he's willing to help improve their funnels/conversion

Ferriss notes he's resisted temptations to diversify into other business models like paywalled content or products, preferring to keep things simple.

Identifying Emerging Trends (43:15)

Ferriss explains how he's identified emerging opportunities:

Look at what "nerds" are doing in their free time
For each book launch, seek out undervalued promotional channels - this led him to blogging, then podcasting
With angel investing, he saw a gap between individual angels and big VC firms in 2008

He emphasizes the importance of finding "uncrowded playing fields" in emerging areas.

Lessons From Building a Small, Efficient Team (50:12)

On working with a small team:

Ferriss acknowledges he's not a natural manager, so he hires self-motivated people
He focuses on connecting the team to the real-world impact of their work
Regular team calls and occasional offsites help build connection in a distributed team

The Power of Constraints in Personal and Professional Growth (52:32)

Ferriss is a big believer in using constraints to drive creativity and growth:

He often experiments with doing the opposite of conventional wisdom
Constraints force you to find novel solutions and efficiencies
Example: Going without a phone for weeks revealed what was truly necessary

Navigating Fame, Money, and Power (54:54)

Ferriss shares candid thoughts on fame, money, and power:

Fame is "almost entirely corrosive" with few real upsides
Money can be "fantastic fuel" if used well, but it's easy to get caught up in it as a game
Power tends to attract more "genuine sociopaths" than fame or money
All three act as amplifiers of existing traits, good or bad

He tries to focus on impact and meaning rather than these external markers of success.

The Impact of Sharing Difficult Stories (1:02:00)

Ferriss discusses two pieces of content he's most proud of:

A blog post on suicide prevention, drawing from his own experience in college
A podcast episode about his childhood sexual abuse

He emphasizes that the pride comes from unburdening himself by sharing these stories, not from audience response. He cautions against making trauma sharing "performative".

Meta-Learning: A Framework for Fast, Effective Learning (1:06:18)

Ferriss explains his DSSS framework for learning:

Deconstruct - Break the skill into constituent parts
Select - Choose the 20% that will give 80% of the results
Sequence - Put the parts in the most effective order
Stakes - Create consequences for following through

He gives examples of applying this to language learning, swimming, and other skills.

Reflecting on a Decade of Podcasting & What's In Store (1:12:32)

Looking ahead, Ferriss notes he's at a crossroads:

The podcast recently crossed 1 billion downloads
It's the longest he's consistently done anything
He's not playing the game as platforms are incentivizing, which may impact growth
Considering experiments in new mediums like screenplays or graphic novels

The Kindest Thing Anyone Has Ever Done For Tim (1:24:41)

Ferriss shares a touching story of a friend who flew out to be with him after a difficult breakup, not to fix anything but just to be present. He's deeply moved by friends who proactively show up during tough times.

Conclusion

Tim Ferriss has built an enormously successful career by following his curiosity, experimenting constantly, and sharing what he learns with others. While his podcast has become a major business, he remains focused on learning, teaching, and having meaningful conversations rather than chasing fame or money. His DSSS framework for learning and his willingness to share vulnerable personal experiences have impacted millions. Looking ahead, Ferriss continues to seek the right balance between business success and staying true to his original motivations, always with an eye towards new frontiers to explore.