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Latest Interviews

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  1. 20VC with Harry Stebbings1h 6m

    Avi Eyal: Making $2.3BN on Monday, Stripe & PillPack from Entrée Capital MP | E1173

    Avi Eyal, Harry Stebbings

    Avi Aviram of Entrez describes an investment strategy prioritizing team quality and founder insideness to generate massive returns, exemplified by a $1.5 billion distribution from a $15 million stake in Monday.com. The firm executes a concentrated portfolio approach that leads follow-on rounds while enforcing strict exit discipline to secure gains before public market volatility. Beyond financial metrics, Aviram addresses the institutionalization of venture capital and calls for a new generation of Israeli leadership to address societal fragmentation and geopolitical challenges.

  2. 20VC with Harry Stebbings1h 7m

    Matt Clifford: The Bull & Bear Case for China's Ability to Challenge the US' AI Capabilities | E1172

    Matt Clifford, Harry Stebbings

    As the era of diminishing returns on raw model scaling approaches, the speaker argues that future value will derive from novel algorithms, multimodal data, and specific product innovations rather than mere compute expansion. While US semiconductor controls and strict Chinese regulations threaten to create divergence in global AI development, the UK's lighter regulatory environment and deep talent pool position it as a superior hub for this next generation of asymmetric, idea-driven startups. The discussion concludes that ambitious founders should capitalize on this window to build AGI-scale companies, noting that success relies more on the performance of top individuals and strategic risk-taking than on traditional team dynamics or financial experience.

  3. 20VC with Harry Stebbings1h 2m

    Samir Vasavada: The Real Story of Vise: The Regrets, Mistakes and Mis-Hires | E1171

    Samir Vasavada, Harry Stebbings

    Founded by a teenage entrepreneur at age 15.5, Vize rapidly scaled to a $1 billion valuation within five years by automating personalized investment solutions for financial advisors, securing early capital from Flatiron Health founders and a seed round led by Keith Rabois. However, the company suffered from a "billion-dollar startup disease" after raising $130 million, which led to premature hiring of senior executives from large tech firms who lacked product-market fit experience and a culture shift toward abstract management concerns. Following a harsh strategic reset in early 2022 that involved firing the majority of the senior team to restore financial discipline and operational focus, the founder continues to steer the company toward replacing traditional asset management platforms with deep personalization while advocating for the necessity of financial discomfort to maintain resilience.

  4. 20VC with Harry Stebbings1h 9m

    Andrew Bialecki: Is Klaviyo the Most Under-Priced Public Company? | E1170

    Andrew Bialecki, Harry Stebbings, Tobi Lütke, Harley Finklestein

    Klaviyo evolved from a bootstrapped email marketing tool into a public enterprise giant with over $50 million in ARR, eventually securing a $100 million Series B at an $800 million valuation before navigating a challenging market to go public. Founders rejected early venture offers to maintain a customer-obsessed culture, later pivoting from a broad "surrogate agent" concept to a unified platform that serves both SMBs and enterprise clients with distinct operational strategies. The company now drives future growth by shifting from selling software tools to selling AI-driven marketing outcomes, leveraging deep partnerships with platforms like Shopify and focusing on long-term profitability and free cash flow generation.

  5. 20VC with Harry Stebbings58 min

    David Luan: Why Nvidia Will Enter the Model Space & Models Will Enter the Chip Space | E1169

    David Luan, Harry Stebbings

    OpenAI's strategic pivot toward an "Apollo project" model aims to solve unsolved scientific problems through massive, focused teams that leverage simulated environments for advanced reasoning rather than simple scaling. As the industry consolidates around 5 to 7 vertically integrated providers due to immense capital requirements, enterprise adoption shifts from rigid Robotic Process Automation to flexible AI agents capable of natural language task execution. This evolution promises to collapse traditional talent stacks and redefine economic value by transitioning knowledge work from transactional pricing to human-AI collaboration, provided incumbent "walled gardens" do not stifle agent interoperability.

  6. 20VC with Harry Stebbings58 min

    Val Scholz: How Revolut Acquired Their First 10M Users: Tips, Tactics & Strategies | E1168

    Val Scholz, Harry Stebbings

    Revolut achieved exponential growth by targeting unsaturated markets and leveraging a referral program that lowered customer acquisition costs to roughly £9 while bypassing paid marketing entirely. The company scaled from a travel card to a comprehensive financial ecosystem by optimizing product activation rates and rebuilding its infrastructure in-house to support millions of monthly transactions. Under the leadership of Nikolay Storonsky, the firm cultivated a high-performance culture focused on rapid iteration, hiring ambitious talent, and utilizing centralized data to drive strategic decisions that allowed it to outmaneuver established competitors.

  7. 20VC with Harry Stebbings1h 2m

    Michael Eisenberg: How China Could Overtake the US in the AI Race | E1167

    Michael Eisenberg, Harry Stebbings

    Distinguished investor Michael Moritz and entrepreneur Harry Stebbings dissect the structural fragility of the current AI landscape, warning that while foundation models are appreciating assets, their rapid depreciation and the dominance of specific teams over technology create high risks for unprepared capital. The discussion outlines a bifurcation in future markets where success depends on binary investment conviction, the consolidation of infrastructure around hyperscaler APIs, and the obsolescence of traditional vertical SaaS in favor of custom-built internal solutions. Furthermore, the speakers highlight critical geopolitical and regulatory divides, asserting that European environments may stifle innovation while the US must avoid closed systems to maintain security and competitiveness against global rivals.

  8. 20VC with Harry Stebbings1h 24m

    Danny Rimer: The Biggest Lessons from Missing Snap, Airbnb, Spotify and Facebook | E1166

    Danny Rimer, Harry Stebbings

    Index Ventures employs a founder-centric investment philosophy that prioritizes exceptional individuals over market size or sector trends, utilizing a strict voting threshold and disciplined "kill or commit" decision rules to filter opportunities. The firm's history includes major successes in companies like King, Figma, and Discord, alongside critical learnings from missed exits in Snap and Spotify that reinforced the necessity of suspending belief in challenging valuations. Now operating as scaled artisans in London, San Francisco, and New York, the partnership focuses on cultivating founder spikes and maintaining cultural integrity through selective expansion and a refusal to chase sector-specific or crypto-related investments.

  9. 20VC with Harry Stebbings1h 7m

    Janie Lee: Three Core Skills that Make the Best PMs | E1165

    Janie Lee, Harry Stebbings

    The event features a seasoned product leader detailing strategies for navigating the transition from product-led growth to enterprise sales, drawing on case studies from Opendoor, Rippling, and Loom. Key insights cover the critical intersection of talent density, financial acumen in pricing, and the philosophical balance between product art and science. The discussion concludes with actionable frameworks for hiring high-potential teams, leveraging AI as a rapid execution tool, and adapting storytelling to ensure long-term business viability.

  10. 20VC with Harry Stebbings1h 6m

    Alex Wang: Why Data Not Compute is the Bottleneck to Foundation Model Performance | E1164

    Alex Wang, Alexandr Wang, Harry Stebbings, Patrick Collison, Trump

    Alex Kawamoto argues that advanced AI poses a critical geopolitical threat when controlled by authoritarian regimes, necessitating a US strategy that prioritizes proprietary "frontier data" over current compute-heavy approaches to secure national security. The industry must overcome a "data wall" by shifting toward human-in-the-loop production methods that convert high-level expert reasoning into training sets, transforming data rights into the primary competitive moat for model providers. As foundational models commoditize, market leadership will depend on hyperscalers and enterprises adopting hybrid data strategies and on-premise solutions to capture value in specialized services while avoiding the regulatory pitfalls that stifle innovation.

  11. 20VC with Harry Stebbings1h 26m

    Reid Hoffman: The Future of TikTok and The Inflection AI Deal | E1163

    Reid Hoffman, Harry Stebbings

    Reid Hoffman frames artificial intelligence as a "steam engine of the mind" that will drive a cognitive industrial revolution by augmenting human productivity rather than causing mass unemployment, despite risks posed by malicious state actors and unavoidable societal inequality. The discussion details a market shift where compute serves as the decade's primary currency, with cloud giants consolidating distribution while startups thrive in niche applications built upon incumbent APIs. Furthermore, Hoffman addresses corporate strategy through Microsoft's acquisition of Inflection AI's emotional intelligence assets and advocates for measured regulation to prevent stifling innovation while preparing for a future defined by AI-driven global health and education initiatives.

  12. 20VC with Harry Stebbings54 min

    Ashley Kelly: The Playbook to Start and Scale Your SDR Team | E1162

    Ashley Kelly, Harry Stebbings

    A comprehensive framework establishes Sales Development as a critical third pillar of go-to-market strategy, defining distinct organizational structures for inbound and outbound teams under Marketing and Sales leadership respectively. The model prescribes a 70/30 compensation split tied to qualified opportunities, aggressive four-month ramping quotas, and a rigorous hiring process that prioritizes resilience, coachability, and proven grit through targeted role-playing. By leveraging AI to automate administrative tasks while maintaining human-led personalization, the approach ensures rapid onboarding and clear internal promotion pathways that position Sales Development leadership for future executive status.

  13. 20VC with Harry Stebbings1h 3m

    Aravind Srinivas:Will Foundation Models Commoditise & Diminishing Returns in Model Performance|E1161

    Aravind Srinivas, Harry Stebbings

    Aravind Srinivasan predicts an imminent shift toward iterative reasoning models that will replace flat subscriptions with pay-per-outcome pricing as raw compute returns diminish and the market consolidates into three or four dominant players. While large foundation models become commodities, companies like Perplexity are capitalizing by prioritizing data orchestration, user experience, and application-layer execution over raw training capabilities. This evolution positions AI as an indispensable assistant for verified knowledge and an integral part of the operating system rather than a standalone chat interface.

  14. 20VC with Harry Stebbings1h 21m

    Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160

    Jason Lemkin, Harry Stebbings

    Following severe market cap losses for Salesforce and MongoDB, the SaaS sector is undergoing a structural shift characterized by valuation compression to 4-8x revenue multiples and a stagnation in M&A liquidity. As enterprise customers prioritize cost rationalization and substitute existing tools rather than expanding budgets, growth is bifurcating between vertical consumer-facing platforms like Canva and struggling "B2B2B" incumbents. With private equity write-downs rising and IPO exits nearly frozen, the industry is settling into a new normal where single-digit growth rates replace historical high-growth trajectories.

  15. 20VC with Harry Stebbings57 min

    Matt Lerner: How to Hire Growth Leaders and Teams and Why in a World of AI | E1159

    Matt Lerner, Harry Stebbings, Adam Gross

    Matt argues that startups must overcome founder hubris by focusing on the single growth channel that drives 90% of results, prioritizing a "discovery" mindset over execution of playbooks to find the specific customer pain point the product solves. Effective growth strategies rely on hiring scientists with first-principles thinking rather than traditional marketers, utilizing deliberate onboarding friction to boost intent, and selecting North Star metrics that reflect actual value delivery instead of revenue. While AI raises the baseline for creative execution, the primary challenge remains identifying autonomous growth loops and timing the shift from broad experimentation to channel optimization once a viable "big swing" lever is validated.