Latest Interviews
Showing 481–495 of 619 interview transcripts.
Clear all filtersSarah 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.
Why Scooter Braun Now Wants to Be Called "Scott"
Scooter Braun, Scott, Harry Stebbings
Investment expert Scott shares a personal revelation that his professional persona, "Scooter," was a protective mask formed from childhood insecurities rather than his true identity. He describes a transformative realization that the version of himself he once rejected was actually the architect of his current success, a shift solidified by his grandmother's advice to love his younger self. This acceptance has allowed him to discard the psychological need to separate his past from his achievements, leading to a recent state of genuine self-approval where he feels comfortable with both names.
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.
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.
AngelList CEO Avlok Kohli: The Funding Market Today; Last-Mile Delivery; Competing w/ Carta | E1005
Following Naval Ravikant's invitation, former founder Avlok assumes the CEO role at AngelList and immediately pivots the firm toward a ruthless operational culture that eliminates all non-essential processes to accelerate product iteration. This strategic shift coincides with a bear market where the company leverages AI automation to scale its infrastructure, shuts down European operations to focus on capturing over 50% of the US market share, and targets a future as the immutable financial fabric of the venture sector without planning an IPO.
Tomasz Tunguz: How I Raised $230M; ChatGPT vs. Google; How LLMs Work; Trump vs DeSantis | E1004
Tomasz Tunguz, Trump, DeSantis, Harry Stebbings
Tom, a solo general partner, successfully raised a $230 million fund to pursue thesis-driven investments in AI infrastructure, utilizing a concentrated portfolio strategy that targets 10% ownership in Series A companies. His investment thesis centers on the convergence of closed and open-source models, predicting that superior execution and unique data moats will allow startups to outmaneuver incumbents like Google and Adobe in the coming decade. The campaign achieved a single close by securing two Institutional LPAC members as anchors and leveraging data room analytics to convert 50% of limited partners from previously unknown relationships.
Why Creatives Will Always Win: The Limitations of Artificial Intelligence in Content Creation
Joost De Valk, Harry Stebbings
The speaker advocates for mandatory disclosure of LLM training data and creator compensation to address transparency gaps, while arguing that AI adoption will compress software development by automating 60–80% of coding tasks within five years. Concerns regarding severe wealth inequality are raised over the potential for hyper-efficient startups with minimal headcount to outpace current regulatory frameworks. Ultimately, the discussion emphasizes the urgent need for explainable AI, the shift toward advanced prompting skills, and the democratization of development through open-source models to mitigate social disruption.
Mark Goldberger: The Ultimate Guide to Enterprise Sales | E1003
Mark Goldberger, Harry Stebbings
Mark, a former wine industry entrepreneur who transitioned to enterprise SaaS sales at companies like TripActions and Ramp, outlines a rigorous methodology for building high-performing sales teams by prioritizing the "Four H's" of talent and utilizing deep qualification frameworks like MedPick. He advises founders to hire their first junior salesperson immediately, compensate them with significant equity, and replace traditional recruitment rubrics with candidates displaying race-car adaptability rather than conventional experience. Drawing on his personal journey and current success in driving Ramp's 400% revenue growth, Mark emphasizes that persistence in outbound outreach and strict deal validation are critical for navigating complex enterprise environments and achieving sustainable market expansion.
Preparing for the AI Revolution: Joost de Valk's Strategies for Navigating the Future of SEO
Joost de Valk, Harry Stebbings
As artificial intelligence floods the content market with low-quality, factually unreliable output, search engines are expected to aggressively prioritize author credibility and E-A-T signals to filter the resulting noise. This dynamic creates a distinct supply shock where only unique, human-driven insights capable of generating genuine user sharing will retain search visibility and commercial value. Consequently, the industry is shifting from algorithmic optimization toward building authentic resources for human readers to ensure long-term discoverability amidst an exponential rise in generic material.
The Freemium Model: Best Practices for Driving Growth and Revenue
Joost De Valk, Harry Stebbings
Yoast SEO co-founders discuss the unique challenges of scaling open source businesses, noting that balancing free access with premium revenue requires deep customer trust to prevent code forking. Strategic success in this sector demands prioritizing the average user over technical power users and leveraging defaults to minimize complexity, while maintaining rapid responsiveness to external ecosystem changes like search engine updates. Ultimately, the conversation highlights that building a robust community and brand is more critical for long-term viability than technical product features alone, as illustrated by Yoast's growth to €15 million in annual revenue while serving millions of sites.
Scooter Braun on Being Enough, Insecurity, Wealth, Investing, Fame, Marriage and Much More
Scooter Braun, Scott Braun, Harry Stebbings
Venture investor Harry Stebbins interviews Scooter Braun to explore the dissonance between external success and internal well-being, with Braun detailing his journey from a childhood "shame lie" to the transformative power of the Hoffman Process at age 39. Braun advises Stebbins to replace the pursuit of work-life balance with harmony, drawing on his own investment experiences and personal crises to illustrate that faith, rather than control, is essential for navigating fear and mediocrity. The conversation concludes with Braun emphasizing the critical importance of accountability, identity, and unconditional love for raising the next generation of leaders while dismantling the illusion that wealth guarantees happiness.
How ButcherBox Built a Thriving DTC Business: Insights from the CEO
Mike Salguero, Harry Stebbings
ButcherBox founder leveraged a residual commission model and strategic influencer partnerships to scale revenue from $300,000 to $33 million within three years while maintaining positive unit economics. The company's growth trajectory relied on validating profitability through a $20–$25 margin per shipment before expanding into paid acquisition channels, ultimately establishing a financial moat that discouraged early competitors. Despite a current net margin of approximately 7% and a $140 customer acquisition cost, the firm's granular focus on "Dollars Per Box" allowed it to sustain operations while industry entry barriers have subsequently increased due to market saturation.
David Marcus: How I Came to Lead PayPal; Why FB's Crypto Failed; How AI Fixes Inequality | E1001
Entrepreneur David Sacks discusses the collapse of Facebook's Libra project as a cautionary tale of political resistance to private global currencies while outlining his vision for LightSpark's open payment protocol to replace fragmented banking systems. He analyzes the evolving crypto and AI landscapes, advocating for regulatory clarity to foster institutional adoption and predicting that artificial intelligence will democratize innovation despite an impending economic recession. The narrative concludes with Sacks' leadership philosophy on hiring top talent and avoiding market saturation, emphasizing that the future of value transfer relies on interoperable infrastructure rather than speculative financial engineering.
Shopify CEO: The Myth That The World is Getting Worse
Tobi Lütke, Harley Finkelstein, Harry Stebbings, Toby
The speaker analyzes global challenges such as deglobalization and income inequality while arguing that historical data shows overall improvements in health and safety despite prevailing anxieties. The presentation distinguishes between fleeting happiness and sustainable contentment, emphasizing that material wealth yields diminishing returns for households earning over $60,000 annually compared to non-material factors like family health and community. Ultimately, the analysis frames political shifts as reactions to local quality of life and identifies high-quality environments and functional tools as superior drivers of well-being compared to luxury acquisition.
Joost de Valk: How I Founded Yoast; The Ultimate Guide to SEO; The Threat of AI | E1000
Joost de Valk, Harry Stebbings
Joost de Valk and his wife Marika scaled Yoast from a hobby project into a €15 million lifestyle business serving 13 million websites by rejecting venture capital and prioritizing organic cash flow over hyper-growth. De Valk highlights critical strategic shifts, including the transition to data-driven product decisions and the adoption of "decisions not options" design principles to serve the 90% of average users. His current angel investment strategy focuses on early-stage founders with strong partner dynamics who aim for rapid self-sustainability, while he warns that AI integration will soon reshape developer roles and amplify the value of human-curated content.