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  1. The Diary Of A CEO1h 21m

    Macklemore: How You Can Overcome Your Darkest Days & Hardest Battles!

    Macklemore, Steven

    Musician and activist Macklemore chronicles his decades-long battle with substance abuse, detailing critical turning points that ranged from a severe relapse during the pandemic to a catalyst moment involving his wife's pregnancy. His journey includes entering rehab at age 26 and helping his business partner achieve sobriety, strategies he now applies to advocate for the disease model of addiction and the importance of support systems like Al-Anon. Now maintaining long-term recovery, he channels these experiences into his latest album *Ben* and his Seattle-based youth program, "The Residency," while explicitly rejecting victimhood to focus on service and creative authenticity.

  2. 20VC with Harry Stebbings6 min

    Snapchat's Best and Worst Product Decisions -- Jack Brody, VP of Product, Reveals!

    Jack Brody, Harry Stebbings

    Snapchat leaders described a strategic evolution where the initially resistance-facing Snap Map became an industry standard through rigorous privacy safeguards and alignment with user behaviors, while product imitation is treated as validation rather than a threat. The organization maintains its unique "raw" ethos and close-friend graph to differentiate itself, alongside a disciplined approach that winds down projects like its Games initiative when they distract from core long-term priorities. This operational framework relies on vetting hundreds of concepts to ensure only ideas with significant strategic fit reach the market, prioritizing high-impact opportunities over broad experimentation.

  3. 20VC with Harry Stebbings8 min

    Building a Winning Team: Jack Brody Shares SnapChat's Insider Guide to Hiring Top Talent!

    Jack Brody, Harry Stebbings

    Snap reframes hiring as an iterative design process that prioritizes solving organizational gaps through internal adjustments before defining roles based on current team needs. During hypergrowth, the company implements a streamlined screening protocol and diverse interview panels to ensure candidate fit while protecting senior leadership time. Success is measured not by perfection but by a 50% adaptability rate, recognizing that both proactive mis-hire corrections and internal role mobility are essential for long-term team velocity.

  4. 20VC with Harry Stebbings8 min

    How SnapChat Builds Its App for Different Countries Around the World: This Will Surprise You!

    Jack Brody, Harry Stebbings

    Following a 2018 Android rewrite that resolved critical accessibility barriers for non-iPhone users, Snap established a "local product, global mindset" strategy that tailors UI and language to specific regional preferences while maintaining a universal core of intimate, ephemeral communication. This approach recently prioritized Japan's visual communication market to differentiate from text-centric competitors like LINE and continues to drive innovation through principles like the "Stories" feature, which solves implicit user needs rather than explicit demands. Early growth was further accelerated by guerrilla marketing tactics that leveraged shared usernames to create personalized viral loops across homogeneous user bases.

  5. 20VC with Harry Stebbings57 min

    Vince Hankes: Why We Put $300M into OpenAI; Sam Altman's Pitch; Lessons from Josh Kushner | E1009

    Vince Hankes, Sam Altman, Josh Kushner, Lee Fixel, Harry Stebbings

    Thrive Capital partner Vince Leverett details the firm's transition from Tiger Global's financial rigor to a founder-empathy model that prioritizes product-market fit and transparent partnership dynamics. Leverett contrasts this approach with past missteps like the missed Canva investment, emphasizing that future success in the competitive AI landscape requires evaluating qualitative strengths over rigid pattern matching. He argues that while infrastructure plays a critical role, the majority of value will accrue to application-layer startups capable of creating entirely new user experiences outside incumbent control.

  6. 20VC with Harry Stebbings7 min

    Ultimate Guide to Deal Champions

    Mark Goldberger, Harry Stebbings

    The presentation outlines a rigorous framework for validating deal champions by demanding their ability to facilitate direct executive meetings with CFOs, while mandating that sellers personally attend these engagements rather than relying solely on internal advocates. Sales professionals are instructed to frame these interactions as strategic partnerships focused on bottom-line impact, requiring thorough preparation of business value assessments and proactive intelligence gathering on target executives. Finally, the strategy emphasizes adopting a skeptical, risk-mitigation mindset to anticipate deal failure points and handle objections directly, ensuring vendors do not overextend their trust in unverified internal stakeholders.

  7. The Diary Of A CEO1h 36m

    The Scary New Research On Sugar & How They Made You Addicted To It! Jessie Inchauspé | E243

    Jessie Inchauspé, Steven

    Jesse Inchauspé, the self-styled "Glucose Goddess," leverages her personal experience with severe spinal trauma and resulting mental health crises to advocate for the management of blood sugar spikes as a foundational health strategy. She outlines ten practical behavioral interventions, including eating fiber before starches and moving after meals, to mitigate the cellular stress, chronic inflammation, and metabolic dysfunction caused by rapid glucose fluctuations. Ultimately, Inchauspé aims to democratize biochemistry knowledge by encouraging the public to view glucose control as a daily habit comparable to hygiene, thereby empowering individuals to prevent long-term conditions like diabetes and Alzheimer's without restrictive dieting.

  8. 20VC with Harry Stebbings9 min

    Parenting Insights from Scooter Braun

    Scooter Braun, Harry Stebbings

    After a 50-50 custody arrangement transformed his approach from distracted to fully present, the speaker leverages fatherhood to eliminate non-essential tasks and cultivate deeper connection with his four-year-old daughter and two sons. Drawing on insights regarding wealth and generational trauma, he prioritizes accountability and unconditional acceptance to ensure his children feel worthy regardless of their achievements. By replacing the result-based approval he received from his own father, the speaker aims to provide a foundation where his children are loved for their existence rather than their performance.

  9. Y Combinator15 min

    Secrets You Can Learn From Your Customers

    Michael Seibel, Dalton Caldwell

    Founders accelerate learning by discarding initial overconfidence to personally engage with early customers, a strategy exemplified by Airbnb's photo visits, Brex's direct work with non-US startups, and Twitch's manual payments to streamers. This deep, one-on-one involvement unlocks specific insights and trust that surveys or data teams cannot provide, as demonstrated by the handwritten notes received from a single host and the creation of niche financial products. Consequently, success relies on maintaining direct founder-customer contact to solve edge cases quickly, avoiding the counterproductive layers of staff that dilute essential feedback.

  10. All-In Podcast1h 16m

    E126: Big Tech blow-out, Powell’s recession warning, lab-grown meat, RFK Jr shakes up race & more

    Powell, RFK Jr, Chamath, Calacanis, Friedberg, David Sacks, Timoth

    Google reported a record-breaking Q1 2024 quarter with a 5% stock surge and historic Cloud profitability, yet investors remain concerned over the company's lack of a clear AI commercialization strategy and insufficient cost-cutting compared to peers like Meta. Broader market analysis suggests that major tech firms have transitioned into cash-flow-focused entities relying on buybacks rather than organic innovation, while a deflationary wave from AI adoption threatens to disrupt white-collar labor markets. Concurrently, the macroeconomic environment faces a potential 50/50 recession risk driven by aggressive Federal Reserve policies, alongside sector-specific distress in commercial real estate and persistent economic hurdles in the alternative protein industry.

  11. Lex Fridman2h 28m

    Robert Playter: Boston Dynamics CEO on Humanoid and Legged Robotics | Lex Fridman Podcast #374

    Robert Playter, Lex Fridman

    From its 2008 Pet Man prototype to the 2022 Atlas generation, the company achieved natural human gaits by resolving mathematical singularities and deploying Model Predictive Control that allows robots to anticipate movements one to two seconds in advance. While evolving from the gas-powered Big Dog to the mass-produced electric Spot and the industrial Stretch arm, the organization prioritized durable, repairable hardware and high initial quality to establish a foundation for over 1,100 operational units. Supported by long-term investors like Hyundai and SoftBank, the firm currently targets industrial profitability to eventually fulfill a vision of ubiquitous robots handling hazardous labor while humans focus on creative endeavors.

  12. 20VC with Harry Stebbings54 min

    Sarah Guo: On Her New $101M Fund; How AI Impacts Inequality; AI Startups vs Incumbents | E1007

    Sarah Guo, Elad Gil, Harry Stebbings

    Sarah Tavel has launched Conviction, a $100 million early-stage fund dedicated exclusively to Artificial Intelligence companies that leverage existing models to build billion-dollar ventures with lean teams. The strategy prioritizes capital efficiency and strategic matchmaking over large upfront check sizes, aiming to support founders in navigating a market where speed and specialized execution outweigh traditional defensibility. Tavel's thesis challenges prevailing venture norms by focusing on high-conviction, niche applications in sectors like legal tech and code generation while advocating for LP discipline to ensure structural sustainability.

  13. 20VC with Harry Stebbings9 min

    Scooter Braun and Harry Stebbings’ Heartfelt Conversation on Their Deepest Worries

    Scooter Braun, Harry Stebbings

    At 25, CEO and largest shareholder of the $8 billion to $14 billion public company Hybe, the speaker initially hesitated to embrace vulnerability with investors due to deep-seated fears of judgment and abandonment rooted in Holocaust-related trauma. Through a dialogue reframing investor relationships as trust in the individual rather than just the achievement, the speaker recognizes that their authenticity is a key asset in attracting capital and must balance with the psychological shift away from viewing self-care as selfishness. This realization drives a new strategic vision to center media and venture capital while addressing personal loneliness, aiming to harmonize the ferocity of business ambition with the presence required for family and long-term self-actualization.

  14. a16z38 min

    Future of Resale: AI Styling, Live Video, Social Marketplaces | Field Notes by Connie Chan

    Connie Chan, Tracy Sun

    Tracy Sun, co-founder and SVP of Seller Experience at Poshmark, outlines the platform's evolution from a casual closet-cleanout app to a professional resale ecosystem where sellers earn incomes rivaling traditional employment. The company drives this growth by integrating AI-powered authentication and live video commerce to foster authentic connections, while specific tools and subsidized shipping strategies target the critical "first sale" inflection point for new seller retention. By embedding engineers in customer events and prioritizing a culture of handwritten notes and community curation, Poshmark continues to solve dual market challenges despite scaling hurdles in discovery and sustainability.

  15. 20VC with Harry Stebbings1h 2m

    Snap's VP of Product Jack Brody: The Future of AR; Snap Glasses; Evan Spiegel's Product Mind | E1006

    Jack Brody, Evan Spiegel, Harry Stebbings, Gustav Soderstrom

    Jack, a Snap product leader who transitioned from mechanical engineering to design, advocates for a philosophy that prioritizes rapid hypothesis validation and the intentional disruption of industry conventions to drive innovation. Under his guidance, Snap leverages low-fidelity prototyping and diverse team input to de-risk bold features like Stories, accepting short-term user friction to secure long-term market dominance. This approach, rooted in balancing analytical rigor with creative intuition, has allowed the company to evolve from a messaging app into a global AR platform while maintaining agility against larger competitors.