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Latest Interviews

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  1. 20VC with Harry Stebbings1h 3m

    Jag Duggal: How We Scaled Nubank to 80M Users; Google's Brutal Hiring Practices | E995

    Jag Duggal, David Velez, Harry Stebbings, Kevin Systrom

    Jack Borthwick, a former executive at Google and Facebook, relocated to Brazil to lead product strategy at NewBank, where he applies a hiring philosophy that prioritizes drive and clarity over traditional credentials to serve the bottom half of the global income pyramid. Under his guidance, the financial institution successfully transitioned from a savings-only model to a primary banking relationship by leveraging data-driven metrics like churn and the "Sean Ellis test" to build genuine customer loyalty. Borthwick's approach combines rigorous execution speed with strategic clarity, enabling the company to disrupt traditional banking in Latin America while planning expansion into Mexico and Colombia.

  2. 20VC with Harry Stebbings49 min

    Dara Khosrowshahi: How I Became CEO of Uber; Uber Eats vs DoorDash; The Postmates Acquisition | E994

    Dara Khosrowshahi, Harry Stebbings

    Dara Khosrowshahi applies a philosophy of sustained excellence and calculated risk to guide Uber through its transformation from a crisis-ridden startup into a globally dominant logistics platform. By prioritizing marketplace technology over failed hardware ventures and correcting strategic missteps in delivery, he has successfully orchestrated complex supply-and-demand matching while shifting the board's focus from control to organizational success. His leadership approach emphasizes hiring for clarity of thought, maintaining a "plastic mind" to embrace mistakes, and allocating capital with a long-term perspective that balances Wall Street expectations with aggressive growth.

  3. 20VC with Harry Stebbings6 min

    Bill Ackman wants to give $7000 to every baby

    Bill Ackman, Harry Stebbings

    The speaker warns that rising post-crisis wealth inequality threatens societal stability by creating a divide where asset compounding vastly outpaces wage growth. To counteract this, the proposal combines a universal "Baby Bonds" program funding $6,500 accounts for every newborn with tax reforms targeting loopholes like like-kind exchanges and unrealized gains taxes. While rejecting a broad 25% tax on appreciation for risking a liquidity crisis in startups, the speaker argues that closing specific loopholes to fund these bonds is essential for providing every citizen a permanent economic stake without harming business formation.

  4. 20VC with Harry Stebbings56 min

    Mike Maples: Lessons from SVB; Crisis Management Tips; USD's Status as the Reserve Currency | E993

    Mike Maples, Harry Stebbings

    Venture capitalist Mike Moritz warns that excessive currency printing and Federal Reserve errors have destabilized the global banking system, predicting a shift toward capital centralization in the "Big Four" banks by late 2023. He advises founders to mitigate these risks through rigorous scenario planning, maintaining liquidity across at least three non-correlated financial institutions, and adopting a crisis communication framework rooted in radical transparency. Furthermore, Moritz outlines shifting venture capital trends, noting that the capital-intensive nature of AI requires longer fund deployment timelines and a strategic focus on product-market fit over traditional board governance.

  5. 20VC with Harry Stebbings1h 2m

    Frank Fillmann: How I Boosted Revenue by $500M at Salesforce; Tips for Hiring Salespeople | E992

    Frank Fillmann, Zhenya Loginov, Harry Stebbings

    Sales leader Frank synthesizes decades of experience, from door-to-door knife sales to managing teams of 75, into a methodology prioritizing potential over experience and the creation of latent demand. He advocates for "servant-leader" managers who build repeatable playbooks starting with financial metrics to cut ramp times to weeks while aligning sales with customer success through early integration. This approach emphasizes hybrid forecasting, deep discovery, and selfless leadership to navigate economic uncertainty and secure high-value enterprise deals in a transparent, remote-first market.

  6. 20VC with Harry Stebbings1h 7m

    Bill Ackman: SVB Collapse, Biden vs Trump, How I Lost $400M on Netflix, Bill's 10-Year Long

    Bill Ackman, Biden, Trump, Harry Stebbings

    Bill Ackman and David Berkowitz launched their partnership with a $3.1 million fund by leveraging a shared track record of high achievement and living together to minimize initial costs. Following significant setbacks during the 2008 financial crisis, Ackman restructured Pershing Square to invest exclusively in liquid large-cap public companies while maintaining a disciplined approach to position sizing based on the risk of permanent capital impairment. In current markets, Ackman advocates for immediate federal guarantees on all bank deposits to prevent runs, argues that persistent inflation requires the Federal Reserve to pause rate hikes, and proposes policy reforms such as universal baby bonds to address wealth inequality.

  7. 20VC with Harry Stebbings9 min

    How the FDIC Saves Failed Banks

    Jackie Reses, Kris Dickson, Harry Stebbings

    Following a weekend takeover by the FDIC, bank staff will analyze Silicon Valley Bank's balance sheet to prioritize repayment to the Federal Home Loan Bank, administrative expenses, and insured deposits up to $250,000. With 98% of depositors holding uninsured funds, the agency aims to stabilize the institution by selling super-liquid assets for immediate dividends or attracting a buyer like Morgan Stanley to assume liabilities, thereby preventing a protracted liquidation similar to Lehman Brothers. The final recovery amount for uninsured claimants will be determined on Monday based on asset sales, with speculation suggesting a potential 50% payout if no buyer emerges immediately.

  8. 20VC with Harry Stebbings7 min

    Will there be more bank runs?

    Jackie Reses, Kris Dickson, Harry Stebbings

    Financial experts warn that secondary bank runs are highly probable and driven by panic psychology rather than fundamental weaknesses, with specific risks concentrated in institutions lacking diversification. To mitigate this, the FDIC plans to announce a buyer by Monday morning offering full deposit guarantees and immediate liquidity to stabilize markets before the U.S. trading day begins. While small businesses face the most severe threat of operational failure due to an inability to meet payroll, aggressive intervention is expected to prevent a worst-case scenario of widespread corporate insolvency.

  9. 20VC with Harry Stebbings1h 2m

    Ophelia Brown: How We Raised $432M in a Pandemic; What's New in European Venture Capital | E990

    Ophelia Brown, Harry Stebbings

    Blossom, a $475 million Series A venture fund co-founded by Ophelia, Imran, and Alex, concentrates its European portfolio on 15 to 20 companies to provide high-touch operational support without relying on traditional investment committees or board seats. Diverging from industry norms, the firm rejects scout models and lead-investor syndication to maximize founder ownership while securing capital through a disciplined strategy that prioritizes speed and growth potential over investor brand prestige. Having overcome initial skepticism as a solo female general partner, Ophelia has established the firm with an explicit goal to become the top-performing venture fund in Europe or globally by 2028 through its concentrated, founder-centric approach.

  10. 20VC with Harry Stebbings7 min

    COMMON MISTAKE: Confusing Metrics and Goals

    Alex Schultz, Harry Stebbings

    This discussion examines the evolution of measurement standards from early-stage "registered users" to modern "monthly active users" while warning against the pitfalls of Goodhart's Law where metrics become targets. Founders are advised to adopt proven frameworks from industry leaders like Meta and eBay rather than reinventing strategies, ensuring their goals align with economic viability rather than mere forecasts. The session further highlights the necessity of human judgment in auditing these systems to prevent gaming, ultimately arguing that disruptive success often stems from singular visions rather than consensus decision-making.

  11. 20VC with Harry Stebbings8 min

    Why did SVB collapse?

    Jackie Reses, Kris Dickson, Harry Stebbings

    The collapse of Silicon Valley Bank resulted from a critical maturity mismatch between its long-dated mortgage portfolio and a concentrated base of tech startup depositors, exacerbated by aggressive Federal Reserve interest rate hikes in 2022. A failed $1.5 billion capital raise announcement triggered a self-fulfilling liquidity crisis where depositors withdrew over $40 billion in hours, forcing the FDIC to seize the institution. This failure highlighted systemic vulnerabilities in the banking sector, where unrealized losses across the insured system reached a record $620 billion in the fourth quarter of 2022.

  12. 20VC with Harry Stebbings6 min

    Facebook CMO explains why they changed their name to Meta

    Alex Schultz, Harry Stebbings

    Facebook Inc. rebranded as Meta to decouple its corporate identity from the Facebook application, aiming to resolve consumer confusion and enable expansion into virtual reality and encrypted messaging services. The company established a cross-functional leadership structure with weekly pillar meetings and shared product roles to ensure knowledge transfer across its portfolio of Facebook, Instagram, and WhatsApp. Post-rebrand analysis by PwC highlighted a dramatic shift in Meta's future potential ranking, validating the strategic move to signal a broadened vision beyond traditional social media to investors and the public.

  13. 20VC with Harry Stebbings1h 4m

    Adam Grenier: The Inside Story to Uber’s Hypergrowth; How We Spent $1B/mo in China | E989

    Adam Grenier, Harry Stebbings

    Adam defines growth as a hybrid of art and science, advocating for a distributed mindset across product and operations rather than relying on isolated teams or premature hires. Drawing on his experiences scaling companies like Uber, HotelTonight, and Lambda School, he outlines a strategic framework centered on North Star metrics, healthy paid-to-organic ratios, and rigorous experimentation to solve product-market fit issues. His approach emphasizes data-driven retention models, proactive organizational structures, and the avoidance of vanity metrics to ensure sustainable, long-term business expansion.

  14. 20VC with Harry Stebbings11 min

    How Instagram Competes with TikTok and Snap | Meta CMO Alex Schultz

    Alex Schultz, Harry Stebbings

    Meta's strategic pivot from relationship-based graphs to algorithmic discovery, exemplified by Reels, demonstrates that rapid iteration and a second-mover advantage often outweigh the risks of entering markets late. While the experimental split of Messenger into a standalone app initially caused usage dips, it ultimately satisfied user expectations for instant replies and forced a leadership reckoning on the dangers of delaying execution for absolute certainty. This evolution underscores a broader organizational shift where data science must translate complex findings into actionable narratives to help leaders balance rigorous measurement with the speed required to avoid missing existential industry waves.

  15. 20VC with Harry Stebbings53 min

    Jackie Reses & Kris Dickson: What Happened with SVB? Are VCs to Blame? | E988

    Jackie Reses, Kris Dickson, Harry Stebbings

    The collapse of Silicon Valley Bank resulted from a critical asset-liability mismatch and hyper-concentration in the tech sector, which triggered a $40 billion single-day depositor run following a failed $2 billion capital raise. The FDIC immediately seized the institution to prevent systemic contagion, leveraging its resolution protocols to prioritize insured deposits while seeking an acquirer to manage the $15 billion in unrealized losses. This event prompted immediate warnings for corporate leaders to diversify banking relationships and accelerate contingency planning against liquidity crises driven by digital communication speeds.