20VC: Tim Ferriss: Why I Walked Away From Angel Investing After...

Tim Ferriss discusses the challenge of maintaining authenticity when having a public persona and the risk of becoming the mask.

Ferriss explains his strategy for content creation, focusing on a niche audience ("1000 true fans") rather than broad appeal, using his podcast as an example of how it was discovered.

He elaborates on the "1000 true fans" concept, providing examples of how specific, targeted fan bases can lead to widespread impact.

Ferriss details how he wrote "The 4-Hour Work Week" as if writing to specific friends, marketing it to a targeted demographic initially, which then rippled outwards.

He shares advice from Andrew Zimmern about being careful with the persona adopted early on, as it can become a lifelong commitment.

Ferriss describes his practice of intentionally releasing content that might alienate a portion of his audience to stay true to himself and shed fair-weather fans.

The conversation touches on the sensationalist nature of algorithms and the need for creators to be mindful of this, even when their teams push for growth.

Ferriss differentiates between key metrics and vanity metrics, emphasizing that views and likes may not translate to business impact unless directly tied to revenue streams.

Ferriss is asked when he felt most lost, and he identifies the overemphasis on productivity and the misconception that money fixes all problems as significant issues.

He explains that money fixes money problems but not emotional or interpersonal ones, acting as an amplifier for existing traits.

Ferriss discusses how investments that cause anxiety or distraction from family are bad, regardless of financial returns, highlighting the importance of game selection.

He shares activities he engages in that are less efficient but enriching, such as reading poetry and fiction, and painting.

Ferriss advises his younger self to start meditating, emphasizing its importance for competitiveness and effectiveness.

He recounts making his first significant money with his sports nutrition company, Brain Quicken, which laid the groundwork for "The 4-Hour Workweek."

Ferriss discusses having arbitrary financial goals early on, like a million dollars, and a more specific goal of matching annual gross income with monthly profit.

When asked what money doesn't fix, Ferriss lists depression, anxiety, insecurities, and interpersonal conflict, noting that money amplifies existing issues.

He likens money to alcohol or power as an amplifier of both good and bad traits.

Ferriss differentiates between the transient depression of chasing wealth and the deeper existential distress of those who achieve it and still feel unfulfilled.

He discusses how money changes relationships, noting that while closest friends remain the same, public visibility increases the volume of people with ulterior motives.

Ferriss breaks down the distribution of his wealth across different ventures, with angel investing being the largest contributor, followed by podcasts and books.

He highlights "The 4-Hour Work Week" as his most profitable book, but notes the ongoing success of "The 4-Hour Body" due to its recent viral resurgence on TikTok.

Ferriss recounts the unexpected viral success of "The 4-Hour Body" on TikTok, driven by a mention in a Gary Brecca video, which significantly boosted sales.

He identifies "The 4-Hour Chef" as his worst-performing book, attributing it to a confusing title and subtitle, and external backlash from Amazon Publishing.

Ferriss reflects on the advice given after "The 4-Hour Work Week" became successful: presentations often fail from too much information, a weakness he believes affected "The 4-Hour Chef."

Ferriss explains that CEOs are often unhappy because they tie their happiness to their company's performance, leading to emotional distress when numbers dip.

He discusses identity diversification as a strategy to hedge against the emotional impact of setbacks, by having multiple pursuits that contribute to self-worth.

Ferriss shares the origin story of his angel investing, which began after his first book's success and a friendship with Mike Maples Jr., as a way to learn and avoid pigeonholing himself.

His initial heuristic for angel investing was to treat it like tuition for business school, focusing on learning, relationships, and skill development rather than immediate financial returns.

Ferriss identifies his biggest early mistake in angel investing as poor allocation and investing too much in a single startup that failed, forcing him to pivot to advising.

He shares the Uber story, explaining how his advisory role at StumbleUpon led to an introduction to Garrett Camp, which eventually resulted in him becoming an early advisor to Uber.

Ferriss admits that selling Shopify stock too early was a $150 million mistake, but acknowledges that at the time, the money felt life-changing and the decision was reasonable given the available information.

He explains why he holds onto Duolingo stock, recognizing he's not a public markets investor and cannot predict outcomes, preferring to let investments ride.

Ferriss explains his decision not to raise a fund, citing impatience, a dislike for the VC grind, and a belief that his style is better suited for smaller, more direct investments.

He discusses his past investment in SV Angel as a way to receive a "report card" on the venture landscape, which informed his subsequent investment decisions.

Ferriss identifies missing out on deals due to too much email and not having enough time to thoroughly vet them as his biggest miss.

He shares the story of missing out on 1Password, a company he admired, due to not fully vetting them initially.

Ferriss describes a "physiological quickening" and intuition that often signals potential in startups, particularly in D2C businesses he can personally use.

He reflects on the difficulty of large-scale retail distribution for products like his new game, Coyote, due to proprietary data.

Ferriss explains that around 2015, the angel investing landscape became too crowded and valuations too high, leading him to pause his involvement.

He explains that he pivoted to podcasting in 2012 as an undervalued platform for content distribution, leveraging his existing blog audience.

Ferriss highlights early guests like Ariel Zuckerberg, Arnold Schwarzenegger, and Jamie Foxx as instrumental in the podcast's initial growth and establishment.

He notes that while the podcast format is no longer novel, its focus on deconstructing world-class performers' habits remains a unique value proposition.

Ferriss confirms that becoming a father is a priority for him, though he hasn't had children yet and is focused on finding a life partner.

He suggests that romantic love as the sole basis for partnership is a relatively new societal construct and not sufficient on its own.

Ferriss values partners who are good at de-escalating conflict and can apologize, highlighting these as critical traits for relationship success.

He learned the importance of patience and acceptance in relationships, moving away from a desire to always "win" arguments or prove objective reality.

Ferriss believes it is acceptable to go to sleep angry if it prevents further dysregulation and allows for a more productive conversation later.

He discusses the creation of the card game Coyote with Exploding Kittens as a way to encourage offline, analog human interaction, which he sees as declining.

The game industry and the intricacies of mass retail distribution are areas of learning for Ferriss with the Coyote project.

Ferriss's metric for success with Coyote includes strengthening relationships, learning about retail, and achieving widespread popularity for the game.

He clarifies the "Four-Hour Work Week" concept as maximizing per-hour output and leverage, not necessarily limiting work hours.

Ferriss jokes about the inefficiencies of extended male health routines, referencing Brian Johnson's experiments.

He would add caveats to his past advice on "what gets measured gets managed," emphasizing that not everything important is measurable and that minimizing microplastic exposure is crucial.

Ferriss would like to have dinner with Richard Feynman, Ben Franklin, or Seneca the Younger to discuss their inner monologues and learning processes.

His interviewing style has evolved to incorporate more questions about the emotional terrain and mental health of guests, not just their practical strategies.

He aims to provide a more complete picture of interviewees by exploring the hidden costs and potential negative side effects of their success.

Tim Ferriss reflects on the difficult decisions of selling stocks, acknowledging a $150 million mistake by selling Shopify too early, but recognizing the context of the time.