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Latest Interviews

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  1. 20VC with Harry Stebbings1h 28m

    Julien Bek on Lessons from Don Valentine, Doug Leone & Alfred Lin | What Sequoia Sees in Founders

    Julien Bek, Don Valentine, Doug Leone, Alfred Lin, Harry Stebbings

    Sequoia Capital partners operate as active deal hunters who leverage a conviction-based voting system to pursue high-conviction outliers like SpaceX and Airbnb while prioritizing deep co-founder intensity across a curated portfolio of roughly twenty companies. Their assessment framework combines vulnerability-based founder screening with specialized analytical models from partners like Doug Leone and Alfred Lin to distinguish genuine entrepreneurial intensity from merely strong resumes. Currently, the firm is positioning itself at the convergence of agent-driven markets and hardware AI, betting on software that masquerades as high-margin service businesses and "end-of-one" founders capable of executing unique architectural shifts.

  2. Sourcery with Molly O'Shea1h 37m

    Wiz: $6M Seed → $32B Exit | Inside the Biggest Cybersecurity Deal Ever

    Gili Raanan, Molly O'Shea, Assaf, Doug Leone, Mike Moritz

    CyberStarts founder Gili Shlomo highlights Wiz's $32 billion valuation as a pivotal moment while warning that the coming decade will usher in autonomous agent warfare that renders traditional human-in-the-loop security measures obsolete. His firm distinguishes itself through a people-first investment thesis that prioritizes founder grit and emotional intelligence over technical pedigree, recently mentoring thirty seed-stage companies toward becoming billion-dollar enterprises. Shlomo projects that this strategy will produce ten new unicorns by year-end, even as he forecasts a volatile interim period where over-provisioned systems and human error create critical vulnerabilities against self-aware threat actors.

  3. Sequoia Capital45 min

    Why AI Will Transform Customer Experience: Cresta CEO Ping Wu and Sequoia’s Doug Leone

    Ping Wu, Doug Leone, Sonya Huang

    Cresta addresses the high attrition and fragmented experience of the global contact center industry by deploying a hybrid model of human agent assistance and autonomous digital agents that operate on legacy systems with under 800-millisecond latency. This approach leverages twenty simultaneously orchestrated AI models to capture the $75 billion in revenue-generating interactions historically lost to inefficiency, while Sequoia's Doug Leone anticipates the application layer becoming the primary locus of value in an "Industrial Revolution 2.0." The company aims to render the distinction between human and AI agents indistinguishable within 20 to 30 years, ultimately creating continuous, personalized customer journeys that span the entire lifecycle.

  4. Sequoia Capital50 min

    Nubank ft. David Vélez: An Outsider Upends the Brazilian Banking System

    David Vélez, Roelof Botha, Cristina Junqueira, Edward Wible, Doug Leone, Rolof Goethe

    Founded in 2013 by David Vélez alongside co-founders Cristina Junqueira and Edward Wiesel, Nubank disrupted Brazil's high-fee banking oligopoly by launching a fee-free digital credit card despite severe regulatory hurdles and a 2016 legislative threat that was neutralized through massive public mobilization. The company secured its first banking license in 2017 and expanded internationally to Mexico and Colombia before executing a successful 2021 IPO that engaged millions of customers via its "New Socios" share program. Currently valued at approximately $775 billion, Nubank continues to leverage its customer-centric culture to scale its operations globally while aiming to transform the underserved $6 trillion financial services market.

  5. Sequoia Capital42 min

    ServiceNow ft. Frank Slootman and Fred Luddy - From Starting Over at 50 to Dodging a $150B Mistake

    Frank Slootman, Fred Luddy, Roelof Botha, Doug Leone, Pat Grady, Carl Eschenbach, Rolof Huerta

    Founded by Fred Luddy in 2004 after a previous bankruptcy, ServiceNow evolved from a free IT help desk tool into a $150 billion enterprise platform through a strategic pivot to broad, seat-based licensing and a complete cloud infrastructure overhaul. In 2011, Luddy ceded the CEO role to Frank Slootman to enforce operational discipline, while investors from Sequoia Capital blocked a $2.5 billion acquisition offer from VMware to force a path toward an IPO. This decision proved prescient as the company's market value surged to $10 billion within two years of going public in 2012, validating the strategy to prioritize long-term disruption over immediate financial stability.

  6. 20VC with Harry Stebbings1h 12m

    Pat Grady: Sequoia Partner on Investing Lessons from Doug Leone, Roelof Botha and Alfred Lin | E1174

    Pat Grady, Doug Leone, Roelof Botha, Alfred Lin, Harry Stebbings

    Pat and Doug Leone of Sequoia Capital prioritize founders with deep domain expertise and intense motivation, utilizing a "vector" assessment to select exceptional talent over favorable market conditions alone. The firm distinguishes its portfolio management through active value creation, exemplified by strategic interventions at companies like ServiceNow and HubSpot, while maintaining a "Day One" culture to mitigate internal arrogance. By combining rigorous due diligence with a specialized operator team and long-term harvesting strategies, Sequoia aims to compound returns by backing leaders who can navigate scaling challenges and unlock trillions in market value.

  7. 20VC with Harry Stebbings1h 10m

    Kevin Ryan: Are the Best CEOs the Best Fundraisers & Why Ownership Should Not Be a Focus in VC|E1138

    Kevin Ryan, Harry Stebbings, Doug Leone, Peter Fenton

    Union Square Ventures has secured a new $250 million external fund to accelerate its "people-led" investment thesis across healthcare, robotics, and deep tech, focusing on deploying capital in New York while incubating six to eight new companies annually with founders retaining 40–45% equity. Partner Kevin Ryan leverages this capital to support exceptional first-time founders in consumer sectors and experienced repeat entrepreneurs in enterprise software, anticipating a market shift from saturated consumer apps toward scientific breakthroughs in gene editing and materials science. While acknowledging potential economic headwinds and AI talent centralization in San Francisco, Ryan emphasizes that successful long-term growth depends on aggressive early team building and selecting leaders who can navigate illiquidity and recessionary cycles over a decade.

  8. 20VC with Harry Stebbings1h 6m

    Chris Dixon: Who Will Win the Next Generation of Venture? | E1132

    Chris Dixon, Dave Frankel, Eric Paley, Marc Andreesen, Ben Horowitz, Doug Leone, Harry Stebbings

    Chris Dixon outlines the diverging strategies of modern venture capital firms, contrasting "heat-seeking" megafunds with "truffle-hunting" boutiques while warning that the consolidation of Big Five tech giants poses an existential threat to open-source innovation. He advocates for regulatory clarity to dismantle the current "casino" dynamic in blockchain, proposing that open-source models and user-owned networks like Farcaster can restore the internet's original bazaar architecture against corporate control. Ultimately, Dixon emphasizes the necessity of fiduciary honesty with founders and the need for resilient capital deployment to navigate the "trough of sorrow" as the sector matures.

  9. 20VC with Harry Stebbings1h 21m

    David Clark: Lessons from 32 Years of Fund Investing - Why Exits Will Be Larger | E1131

    David Clark, Harry Stebbings, Doug Leone, Ryan Akinna

    A longitudinal analysis of 1,200 funds reveals that while only 2.6% achieve 5x net DPI, a specific investment firm has maintained a loss rate under 3% by rigorously selecting a core group of top-tier managers during low-noise cycles. This strategy prioritizes identifying the 1% of managers capable of accessing power-law outcomes, utilizing a 100% outbound sourcing model that focuses on Fund 3 launches and enforces three-year deployment periods to mitigate timing risks. Operating with a blended return of 3x to 3.5x across mature funds, the firm continues to navigate market volatility by avoiding overpaying in inflated cycles and adapting to a shifting landscape where late-stage investing faces commoditization while early-stage craft remains essential.

  10. 20VC with Harry Stebbings1h 9m

    Gili Raanan: One of the Best Seed Investor of All Time: 1 Decacon, 7 Unicorns, 4 Acquisitions| E1128

    Gili Raanan, Mike Moritz, Doug Leone, Harry Stebbings

    Investor Harry Stebbings outlines CyberStarts' "Sunrise" methodology, a rigorous process where founders validate problems through 60-70 customer conversations before writing code, a strategy that has transformed seven of the program's first seventeen companies into unicorns or decacorns. Stebbings prioritizes team resilience and personal hardship over market timing, asserting that deep psychological understanding of founders provides better predictive value than traditional technology assessments. This approach, coupled with a massive $500 million opportunity fund for follow-on investments, positions CyberStarts as a premium partner that demands discipline while securing dominant market positions for its cybersecurity portfolio.

  11. 20VC with Harry Stebbings1h 4m

    Peter Wagner: 27 Years of Investing Lessons of Picking Founders, Price Discipline & Reserve | E1123

    Peter Wagner, Harry Stebbings, Roger Ehrenberg, Doug Leone

    Wing positions itself as a boutique return generator focused on high-bandwidth B2B founders who are motivated by market deficiencies, deliberately avoiding capital-intensive sectors like LLM development in favor of application transformation. The firm prioritizes time-intensive partnerships and deep product expertise over scale, learning from past mistakes in telecommunications and missed opportunities like Snowflake to refine its strategy. With a flat decision-making culture and a long-term view on liquidity, Wing aims to build enduring value for the next generation of technology leaders while rejecting the "safety in the herd" mentality that drives cyclical bubbles.

  12. 20VC with Harry Stebbings1h 9m

    David Velez: How AI Changes The Future of Finance | E1059

    David Velez, Harry Stebbings, Doug Leone

    David Vélez transformed Sequoia Capital's character-centric interview methodology into the founding philosophy for Nubank, a Brazilian digital bank that now serves nearly half the country's adult population by prioritizing deep market penetration over rapid geographic expansion. Facing an exit from Sequoia's Latin American division due to a lack of local investment opportunities, Vélez leveraged that direct feedback to build a "beginner's mind" culture focused on solving financial exclusion rather than mimicking Silicon Valley models. The company is currently capitalizing on AI as a second platform shift to democratize high-net-worth banking and evolve into a broader consumer marketplace, all while vigilantly avoiding internal complacency in a region where traditional financial incumbents remain vulnerable to disruption.