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Latest Interviews

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  1. 20VC with Harry Stebbings42 min

    Marc Benioff, Salesforce Founder: Why Salesforce Isn't Hiring Software Engineers | E1236

    Marc Benioff, Harry Stebbings, Steve Jobs, Mark

    Salesforce is reorienting its 2025 strategy toward its proprietary AgentForce platform, halting new software engineer hiring while expanding its sales force to drive adoption of a unified agentic architecture. This shift, supported by a 32.9% margin and $38 billion revenue guidance, positions the company as the world's leading enterprise AI supplier processing over two trillion transactions weekly. Under CEO Mark Benioff, the organization is pivoting from traditional per-seat SaaS pricing to a consumption-based model that leverages a best-in-breed ecosystem of foundational models to capitalize on maturing Large Language Model capabilities.

  2. 20VC with Harry Stebbings39 min

    Sam Altman: What Startups Will be Steamrolled by OpenAI? Where is Opportunity?

    Sam Altman, Harry Stebbings

    OpenAI outlines a strategic roadmap prioritizing rapid advancements in reasoning and multimodal capabilities to drive scientific discovery, explicitly advising against building startups that rely on temporary patches for current model limitations. Leadership emphasizes a shift toward integrated AI agents capable of long-duration tasks and a compute-based pricing model, while acknowledging the competitive landscape involves both open-source collaboration and secure, scalable proprietary services. Looking five to ten years ahead, the organization forecasts an "unbelievably rapid rate of improvement" in technology and science, though significant societal changes are expected to be reserved for the distant future rather than the immediate term.

  3. 20VC with Harry Stebbings41 min

    Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196

    Scott Gorlick, Harry Stebbings, Travis Kalanick, Dara

    Former employee Harry details Uber's early scaling strategies, including high-velocity driver incentives, manual acquisition tactics, and the pivotal UberX product launch that secured market dominance. The narrative highlights the company's aggressive expansion model, which utilized city-level autonomy and substantial promotional subsidies to capture market share before facing regulatory hurdles and losing execution focus to distractions like Uber Elevate. Ultimately, the account contrasts the founder-led speed of the Travis Kalanick era with a slower committee structure, while identifying advertising as an undervalued asset and arguing for a software-centric approach to autonomous vehicles.

  4. 20VC with Harry Stebbings45 min

    Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148

    Keith Rabois, Eric Glyman, Harry Stebbings

    Ramp, a $7.6 billion corporate card and procurement platform, redefines its identity as a productivity engine that leverages AI to automate financial workflows and reduce enterprise spending. Co-founded by Eric and Karim, the company prioritizes internal promotion and a rigorous "day count" operational system to navigate rapid scaling challenges while targeting the 99% of corporate spend currently outside current fintech coverage. With the backing of Founders Fund and Khosla Ventures, Ramp aims to reverse the national productivity slump by repositioning finance teams from tactical execution to strategic analysis, positioning the organization to handle a significantly larger share of the market over the next decade.

  5. 20VC with Harry Stebbings35 min

    Dave Ripley: Are the SEC Overreaching with its Approach to Crypto? Should Gensler Step Down? | E1108

    Dave Ripley, Gensler, Harry Stebbings

    Kraken CEO Dave Ripley characterizes the current U.S. regulatory environment as flawed, advocating for legislative frameworks similar to those in the UK and Europe while anticipating a pro-cryptocurrency shift following the next presidential election. Since ascending to the top role in 2023, Ripley has steered the company toward a culture of transparency and global consumer expansion, emphasizing Bitcoin's role in cross-border payments and inflation hedging. Looking ahead to 2028, the organization forecasts an order-of-magnitude growth driven by its remote infrastructure, established compliance moat, and a strategic focus on institutionalizing cryptocurrency as a foundational financial rail.

  6. 20VC with Harry Stebbings33 min

    The Ultimate AI Roundtable: What Happens Now in AI, Why Google are Vulnerable | E1085

    Des Traynor, Yann LeCun, Emad Mostaque, Jeff Seibert, Tomasz Tunguz, Douwe Kiela, Cris Valenzuela, Richard Socher, Harry Stebbings, Myles Grimshaw, Christian Lang

    A diverse panel of AI industry leaders predicts a market consolidation around five to six dominant providers while debating the trajectory from proprietary scale to commoditized, open-source efficiency. Experts contrast conflicting views on model defensibility, with some arguing that data quality and iteration speed matter more than parameter counts, while others maintain that massive size remains essential for handling complex tasks. The discussion further outlines a structural shift in value accrual from cloud infrastructure to differentiated applications, forecasting a pivot in business models toward outcome-based pricing and predicting existential challenges for search incumbents like Google alongside opportunities for hardware-integrated strategies from Apple.

  7. 20VC with Harry Stebbings42 min

    Roundtable #6 with Rebecca Kaden, Nicole Quinn, Eurie Kim, Harry Stebbings | E1083

    Rebecca Kaden, Nicole Quinn, Eurie Kim, Harry Stebbings, Yuri

    Market dynamics analysis reveals a bifurcated seed and Series A landscape where stable valuations coexist with falling later-stage deal sizes, forcing a strategic shift from "growth at all costs" to sustainable unit economics. Lightspeed Venture Partners and other institutional investors are redefining their structures and AI investment thesis, focusing on application-layer efficiency gains and specialized stage funds while rejecting multi-stage dominance in early checks. Industry leaders anticipate a future driven by non-consensus opportunities and collaborative models that solve tangible problems, signaling a return to fundamentals as the sector navigates rising startup mortality rates and underwater employee equity.

  8. 20VC with Harry Stebbings27 min

    Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?"

    Matthew Prince, Harry Stebbings

    Cloudflare CEO Harry Stephenson challenges the prevailing startup dogma of starting with narrow niches by arguing that ambitious, broad visions are essential for attracting top talent and unlocking wild success outcomes. Drawing on Cloudflare's trajectory, he demonstrates how targeting a massive initial market rather than a pre-determined segment allowed the company to discover high-value users in civil society while avoiding the stagnant "slog" of incremental growth. Stephenson concludes that venture-backed founders must prioritize recruiting incredible people and setting non-trivial targets over optimizing for immediate efficiency, as only a expansive scope can justify the risk required for exponential scaling.

  9. 20VC with Harry Stebbings30 min

    Marc Benioff: The Future of San Francisco and What He Would Do if in Charge | E1064

    Marc Benioff, Harry Stebbings

    Salesforce CEO Mark Benioff outlined the company's strategic shift toward autonomous AI agents and the launch of the Einstein 1 platform while asserting its status as the leading enterprise AI provider. Benioff defended San Francisco's economic vitality through record office demand and proposed increased policing to address safety concerns, all while reinforcing the firm's hybrid work model and commitment to its philanthropic 1-1-1 legacy. Looking toward 2033, the organization aims to integrate generative AI and AGI capabilities across its CRM suite through collaborative futurist strategies and a core values framework centered on trust, innovation, and customer success.

  10. 20VC with Harry Stebbings37 min

    Noam Shazeer: How We Spent $2M to Train a Single AI Model and Grew Character.ai to 20M Users | E1055

    Noam Shazeer, Harry Stebbings

    Noam Shazeer, CEO of the full-stack AI platform Character.ai, leads a direct-to-consumer initiative processing 450 million daily messages by leveraging neural language modeling to deliver flexible superintelligence to 20 million users. The company distinguishes itself through a B2C strategy that encourages user-driven innovation, successfully adapting to unexpected adoption trends where users employ AI characters for emotional support and companionship rather than pre-defined enterprise tasks. While prioritizing data privacy and treating hallucinations as creative features for engagement, Shazeer positions the platform at the forefront of an emerging technological wave comparable to the invention of electricity, where massive computational scale drives human-level conversation.

  11. 20VC with Harry Stebbings23 min

    Deep Dive on Threads with the Head of Instagram Adam Mosseri

    Adam Mosseri, Harry Stebbings

    Threads achieved immediate high-volume adoption by importing Instagram's social graph to prevent a zero-follower start, though Adam Mosseri stresses that long-term retention remains the primary strategic focus over initial sign-up numbers. The platform successfully activated creators in key verticals without direct payments, yet it faces technical hurdles such as a delayed European rollout due to data separation laws and the absence of core editing features. Mosseri argues that sustainable monetization must prioritize predictable revenue tools like subscriptions over volatile direct payments, while acknowledging that critical mass requirements for user retention vary significantly across different cultural markets.

  12. 20VC with Harry Stebbings39 min

    Kevin Egan: Biggest Lesson on Managing Sales Teams at Slack and Atlassian | E1034

    Kevin Egan, Harry Stebbings

    Sales leader Kevin outlines a strategic framework for scaling organizations by transitioning from dynamic, founder-led sales motions to structured enterprise operations that balance product-led growth with rigorous security and compliance requirements. He details a rigorous five-to-seven-step hiring process designed to identify "renaissance reps" capable of adapting to early-stage ambiguity while warning against over-reliance on candidates from legacy large-tech firms. Furthermore, the presentation addresses contemporary market challenges by advocating for CFO-aligned forecasting, strict discounting protocols, and a feedback culture that shifts from directive management to strategic partnership as teams mature.

  13. 20VC with Harry Stebbings23 min

    Rishi Sunak: The UK's New High Potential Visa; Rishi's £100M AI Task Force | E1025

    Rishi Sunak, Harry Stebbings

    Prime Minister Rishi Sunak is establishing the UK as a global AI hub through a £100 million safety Task Force and new visa pathways designed to recruit top international talent. Major tech firms including DeepMind, Anthropic, and OpenAI have committed to early access for safety evaluations, while international investment firms like Andreessen Horowitz and Palantir are expanding their British operations. This strategy aims to replicate the Industrial Revolution's economic impact by combining government-backed research with a risk-tolerant regulatory framework and a focus on educational reform.

  14. 20VC with Harry Stebbings26 min

    How Dire is the Startup Funding Market Today? | AngelList CEO Avlok Kohli

    Avlok Kohli, Harry Stebbings

    AngelList analyzed its data from managing over 13,000 startups to reveal a rapid market contraction where Series B and C deal volumes and valuations have plummeted by more than 50%, shifting the industry into its most severe "bad times" historically. While early-stage valuations remain artificially stable due to capital from later-stage investors, the firm warns that adverse selection, extended fundraising timelines, and a lack of credible traction are shutting down capital access for most startups. Simultaneously, secondary market discounts on fund positions range from 20% to 50% as liquidity pressures mount, and the firm anticipates an acceleration of down rounds and M&A slowdowns over the next 18 months unless macro conditions improve.

  15. 20VC with Harry Stebbings39 min

    Alex Rodriguez: From MVP to CEO; Business Lessons from Warren Buffett & Magic Johnson | E1010

    Alex Rodriguez, Warren Buffett, Magic Johnson, Harry Stebbings

    Alex Rodriguez leverages his transformation from a performance-enhanced suspension to a disciplined investor to guide A-Rod Corp through strategic ventures in real estate and sports, including the twelve-fold return on Petro's Pace. Drawing on mentors like Magic Johnson and Warren Buffett, Rodriguez prioritizes deep expertise and "hire slow, fire fast" principles to build teams that balance aggressive deal-making with a renewed focus on fan affordability and leadership accountability. His current operations concentrate exclusively on sports and real estate sectors, aiming to lead the Minnesota Timberwolves to a championship while maintaining a corporate culture rooted in empathy and present fatherhood.