Latest Interviews
Showing 16–24 of 24 transcripts.
Clear all filtersPredictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges
Jason Lemkin, Rory O'Driscoll, Harry Stebbings
The 2026 IPO cycle is projected to backload major public debuts for companies like SpaceX, Canva, Databricks, and Anthropic, while OpenAI delays its listing until 2027 amid high burn rates and trillion-dollar valuation challenges. Key industry figures including Dario Amodei and Gwyn Shotwell were honored for their leadership, while venture capital winners such as Index Ventures and Hummingbird Capital demonstrated exceptional returns through strategic exits. Despite predictions of robust growth for AI-centric stocks like Salesforce and Notion, the market faces significant political and societal risks as potential AI-driven unemployment could trigger a severe backlash against the technology sector.
Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan
Jason Lemkin, Rory O'Driscoll, Harry Stebbings
OpenAI executed a strategic pivot to prioritize core product stability through an internal "code red" while deepening its financial alliance with Thrive Holdings to concentrate capital on proven winners. Concurrently, the market is witnessing a fierce competitive trajectory between Databricks and Snowflake, with Databricks rumored to command a $134 billion valuation at 55% year-over-year growth by leveraging its five-year technological lead in AI-centric data manipulation. These corporate maneuvers reflect a broader industry shift where incumbents are consolidating market share via security mandates and efficiency drives, forcing startups to either solve harder infrastructure problems or face rapid obsolescence in a capital-intensive environment.
Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition
Roger Ehrenberg, Jason Lemkin, Rory O'Driscoll, Harry Stebbings
Goldman Sachs acquired Industry Ventures for up to $965 million to expand its private markets platform, while a panel analyzed how Andrew Tullock's $3.5 billion exit to Meta illustrates a shift toward transactional human capital deals over traditional founder loyalty. Investors are simultaneously navigating high-stakes AI leverage strategies, such as SoftBank's $5 billion margin loan for OpenAI, and debating whether capital-intensive prediction markets like Polymarket represent genuine innovation or regulatory arbitrage. Strategic discourse further emphasized the tension between portfolio concentration and diversification, noting that extended exit timelines in the current VC environment necessitate long-term stewardship and flexible follow-on funding structures.
OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds
Jason Lemkin, Rory O'Driscoll, Harry Stebbings
OpenAI secured a strategic partnership with AMD to purchase six gigawatts of Instinct chips in exchange for equity warrants, a deal that triggered a 30% surge in AMD's stock price while reinforcing OpenAI's leverage over chip manufacturers. Concurrently, OpenAI Developer Day introduced native app integrations and an "AgentKit" tool to accelerate AI agent development, though critics questioned the immediate utility of these features compared to existing ecosystems. In the broader venture landscape, massive valuations for infrastructure firms like Vercel and Supabase coexist with tightening liquidity for sub-scale assets, as university endowments divest stakes and new SPAC structures aim to curb speculative pricing.
Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19
Rory O'Driscoll, Jason Lemkin, Harry Stebbings
The discussion analyzes Databricks' $100 billion valuation and private market dynamics as companies like Canva and Stripe prepare for IPOs, while noting that secondary markets allow employees to monetize equity without traditional retention. Fintech leaders such as NewBank and Revolut demonstrate how neobanks exploit incumbent inefficiencies globally, contrasting with CoreWeave's $11.2 billion debt strategy to fund AI infrastructure for hyperscalers. Finally, the session projects accelerating AI adoption driving B2B consolidation, predictions for major model releases and acquisitions, and the imminent IPO of Deal versus Rippling's continued investment phase.
Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers
Rory O'Driscoll, Jason Lemkin, Harry Stebbings
The event analyzes the current AI competitive landscape where Google leads execution while incumbents like Microsoft and Meta struggle to catch up to agile new entrants. Simultaneously, the venture capital ecosystem is shifting toward solo funds and massive check sizes, evidenced by the rising dominance of Anthropic and OpenAI in a market where traditional diversification rules are being overridden by proven winners. Finally, the discussion evaluates macroeconomic risks surrounding rapid AI infrastructure depreciation and the emerging convergence between design tools like Figma and autonomous coding agents.
Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market
Rory O'Driscoll, Jason Lemkin, Harry Stebbings
The Chime S1 filing reveals an expected IPO valuation of $10 billion to $12 billion, a significant drop from its $25 billion private peak driven by regulatory reliance on the Durbin Amendment and potential investor ratchet protections. This event reflects broader venture market shifts where financial services firms prioritize public listings for scalable capital while AI adoption threatens traditional SaaS moats by commoditizing core applications. Concurrently, corporate strategies are pivoting toward aggressive settlements in legal disputes and structural transitions like OpenAI's move to a Public Benefit Corporation to navigate governance and profitability challenges.
What Does it Take to Be Good at Series A and B Today?
Rory O'Driscoll, Jason Lemkin, Fabrice Grinda, Harry Stebbings
Venture capital markets are currently navigating a dual reality defined by an AI-fueled "gold rush" and a constrained liquidity environment where exit windows remain closed. Investors are diverging between aggressive "megatrend" bets on artificial intelligence and defense technology versus deep-value plays in digitized B2B sectors, while grappling with rapidly evolving risks such as model obsolescence and geopolitical instability. This high-velocity landscape is forcing strategic shifts toward earlier exits, a preference for "deranged" founders capable of exponential scaling, and a structural reevaluation of how private company lifecycles align with technological obsolescence.
a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game
Josh Kushner, Rory O'Driscoll, Jason Lemkin, Harry Stebbings
The discussion analyzes a shifting venture capital landscape dominated by high-concentration "Thrive" strategies that prioritize massive late-stage liquidity over diversified early-stage portfolios, while noting that traditional SaaS models are becoming obsolete due to volatile product-market fits and aggressive AI competition. Investors face significant headwinds including a $2 trillion liquidity crunch in mature software, a mismatch between PE acquisition criteria and VC-backed horizontal startups, and ethical erosion driven by normalized secondary cash-outs and accounting manipulation. Despite these structural risks, institutions continue deploying capital into binary AI bets and founder-concentrated funds, even as market valuations reach unsustainable levels that threaten a future correction when private exit mechanisms fail to satisfy limited partners.