Ev Williams on Strategic Quitting, Building Twitter, and the Art of Not Planning Greatness

A rare live conversation with the Twitter co-founder reveals why sometimes the best strategy is knowing when to quit and embrace uncertainty.

Key Takeaways

• Strategic quitting often creates more opportunities than stubborn perseverance, as demonstrated when Odeo's failure led directly to Twitter's creation
• The most innovative products cannot be plotted in advance - trying to over-plan cuts off unexpected possibilities that drive breakthrough innovation
• Premature scaling kills more startups than lack of ambition, with founders typically needing to "do less" rather than more to succeed
• Personal growth work, including meditation and emotional intelligence, becomes increasingly valuable as artificial intelligence handles more technical tasks
• Real social connection happens offline, which is why location-based apps like Mosy focus on facilitating in-person gatherings rather than digital engagement
• Reading and writing remain fundamental thinking tools that AI cannot replace, as the process itself generates clarity and creative ideas
• The Hoffman Process delivers transformative personal development results by stripping away professional identities and creating authentic human connections
• Investment opportunities exist in solving humanity's biggest challenges, particularly climate change and mental health through psychedelics research
• Feel your feelings rather than avoiding them - emotional avoidance creates more suffering than the emotions themselves

Strategic Quitting: The Underappreciated Business Skill

• Most entrepreneurs and companies stay trapped in failing ventures far longer than rational analysis would suggest, primarily due to sunk cost fallacy and ego protection rather than sound business judgment. Ev Williams experienced this firsthand when Odeo, his podcasting company, got completely undermined by Apple's iTunes podcast integration in 2005, making their core product obsolete overnight.
• The decision to shut down Odeo came after Williams wrote a comprehensive strategic document outlining how the company could pivot and survive in the podcasting space, but realized he personally had no passion for executing that vision. "I wrote this big strategic doc about how to succeed in the podcasting business and it was very convincing... and I was like, I don't want to do this."
• Williams distinguishes between productive perseverance and destructive stubbornness based on belief in the underlying vision. With Blogger, he maintained unwavering faith in the product even while running out of money and laying off employees, but with Odeo he felt no personal connection to podcasting despite the company's potential viability.
• The opportunity cost of continuing failed ventures often exceeds the obvious financial losses, because entrepreneurs cannot discover what else might be possible while their attention remains locked on struggling projects. "You don't know what else there is until you clear that your attention away from the thing that you've been struggling with."
• Andy Duke's book "Quit" provides frameworks for recognizing when persistence becomes counterproductive, highlighting how identity, ego, and social expectations trap people in situations long past their rational expiration date.
• Strategic quitting requires distinguishing between external metrics and internal conviction - Odeo wasn't technically dead but Williams lacked the personal drive necessary for breakthrough innovation in that space.

The Accidental Genesis of Twitter

• Twitter emerged from a company-wide hackathon at Odeo after Williams told investors the podcasting venture needed to end, leading to a desperate search for alternative product directions with the existing team of 12-14 employees.
• The initial concept evolved through multiple iterations: starting as voice message broadcasts via phone, then shifting to text-only broadcasts, and finally incorporating following mechanisms borrowed from RSS and blogging platforms to create a hybrid social information system.
• Jack Dorsey and Biz Stone led the technical development, drawing inspiration from status messaging systems, SMS capabilities, and Dorsey's previous work on courier and dispatch systems, while Williams provided product vision and strategic direction.
• The team recognized Twitter's potential immediately with just 10 internal users, but the product remained stagnant for months until gaining critical momentum at South by Southwest 2007 through a strategic $11,000 investment in hallway screen displays.
• South by Southwest 2007 became Twitter's breakthrough moment because the conference attracted exactly their target demographic - early-adopting bloggers and tech innovators who understood the value proposition and could achieve critical mass within a concentrated environment.
• The platform's success came from solving a fundamental information-sharing problem that existing social networks hadn't addressed, rather than trying to compete directly with established players like Facebook in their core social networking territory.

Why Greatness Cannot Be Planned: The Innovation Paradox

• Ken Stanley's book "Why Greatness Cannot Be Planned" provides the theoretical framework Williams uses to understand why breakthrough innovations resist traditional goal-setting and strategic planning methodologies, particularly for creating unprecedented products.
• The premise distinguishes between formulaic achievements that can be planned step-by-step (like training for a marathon) versus innovative breakthroughs (like inventing Twitter or creating groundbreaking art) that require embracing uncertainty and following unexpected opportunities.
• Williams experienced this principle directly when building Medium, where investor and employee pressure for concrete roadmaps and growth targets actually hindered the creative product development process necessary for true innovation.
• Evolution serves as nature's example of incredible creativity without predetermined goals - "the most creative force in the world is clearly nature and like it has no plan. It just tries [stuff]. Trial and error" - suggesting that systematic experimentation beats strategic planning for breakthrough discoveries.
• The book provided Williams relief during his Medium tenure because it validated his intuitive understanding that creative product development requires tolerance for ambiguity and resistance to premature optimization around specific metrics.
• Traditional business culture creates pressure for concrete plans and measurable milestones that can actually sabotage innovation by forcing entrepreneurs to commit to specific directions before understanding what's actually possible or valuable.

Mosy: Building Actually Social Technology

• Williams launched Mosy within the last year as a location-based app designed to facilitate real-world social connections by showing users which friends are currently in their city and available for in-person activities.
• The product philosophy explicitly rejects the "social media" model that has dominated the internet, instead focusing on utility for offline relationship building rather than online engagement, performance, or advertising revenue generation.
• Mosy originally started as a better contacts management system inspired by the old Plaxo concept, where connected users could automatically update each other's contact information, but evolved toward location-sharing after recognizing the core value proposition.
• Williams and his team deliberately removed customizable digital business card features after building them, recognizing that aesthetic personalization created noise that distracted from the core utility of knowing when friends were nearby and available.
• Privacy concerns around location sharing are addressed through multiple opt-in layers: users must explicitly sync contacts, then separately opt-in to share plans with specific individuals, and location updates require active input rather than automatic tracking.
• The long-term vision positions Mosy as a "ubiquitous social network" designed for enhancing real relationships rather than building audiences, explicitly avoiding the media platform, advertising, and performance-driven models that characterize current social networks.

Personal Growth and the Hoffman Process

• Williams describes the Hoffman Process as "20 years of therapy in a week" - a intensive seven-day retreat in Petaluma, California, where participants surrender phones and engage in emotional work with 36 strangers without revealing last names or professional identities.
• The anonymity aspect proved particularly revelatory for Williams, who realized how much he relied on professional recognition and status as barriers to authentic human connection, forcing him to relate to people based purely on personality and emotional presence.
• The structured program has been refined over 50 years and creates safety through its format rather than its content, allowing participants to share vulnerable experiences with strangers in ways that feel more secure than traditional therapy or personal relationships.
• Williams credits the Hoffman Process with more meaningful personal transformation than years of conventional therapy, though he emphasizes that multiple approaches contributed to his emotional development including meditation, psychedelics, and stopping alcohol consumption.
• The retreat format addresses the introversion concerns that initially made Williams hesitant to participate, creating an environment where sharing personal struggles feels natural and supportive rather than exposing or performative.
• Williams recommends the process as his most impactful personal development experience, noting that many podcast listeners have written to thank him for the indirect recommendation and report significant life improvements after completing the program.

Investment Philosophy and Future Trends

• Williams operates Obvious Ventures as a venture capital firm focused on companies addressing fundamental human problems, particularly climate change solutions and mental health innovations through psychedelics research and therapeutic applications.
• Climate change represents a long-term investment opportunity despite current market volatility, because the underlying problem will only intensify over time, creating sustained demand for effective technological and business model solutions.
• Psychedelics investment appeals to Williams because of the compounds' therapeutic potential for addressing mental health challenges, though he acknowledges concerns about mass adoption of powerful consciousness-altering substances without proper cultural frameworks.
• Williams distinguishes between psychedelics as investment opportunities versus therapeutic tools, preferring that effective treatments remain accessible and generic rather than becoming proprietary pharmaceutical products that limit access through patents and pricing.
• The historical context of psychedelic use suggests caution about scaling therapeutic compounds to mass market adoption, since traditional cultures typically restricted access to very small percentages of their populations rather than widespread consumption.
• Williams avoids specific investment advice but emphasizes focusing on fundamental human needs and long-term societal challenges rather than trend-following or financial engineering approaches to venture capital.

Meditation, Reading, and Skill Development in the AI Age

• Williams committed to daily meditation throughout 2024 after recognizing the transformative power of consistency, using the psychological hook of a year-long goal to maintain practice discipline and measure the cumulative effects.
• His meditation teacher's principle that "you can't boil water if you keep turning off the flame" highlights how sporadic practice prevents reaching deeper meditative states that only become accessible through sustained daily commitment.
• Williams practices mindfulness meditation focusing on breath awareness and open monitoring rather than transcendental meditation techniques, often using The Waking Up app by Sam Harris for guidance and structure.
• Reading and writing remain essential thinking tools that AI cannot replace because the process itself generates clarity and creative insights, not just the final written product that AI might be able to produce more efficiently.
• For children's education in an AI-dominated future, Williams emphasizes social emotional learning (SEL) and interpersonal skills alongside reading and writing, recognizing that human connection capabilities will become increasingly valuable as technical tasks become automated.
• Williams encourages his children to pursue whatever subjects genuinely interest them rather than trying to "AI-proof" their careers, believing that curiosity and creative problem-solving abilities will remain more valuable than specific technical skills.

The conversation reveals how strategic thinking often means embracing uncertainty rather than eliminating it, and why the most valuable innovations emerge from following curiosity rather than executing predetermined plans. Williams built his career by learning when to quit, when to persevere, and how to distinguish between the two.