Rory O’Driscoll

Jason Lemkin, SaaS investor and founder of SaaStr, and Rory O'Driscoll, enterprise-focused VC, trade rapid takes on market-moving tech deals and AI-driven shifts. They cover SpaceX buying xAI and its implications, the 2026 SaaS market collapse and which software categories are at risk, Microsoft and Nvidia controversies, Waymo’s huge raise, and the rise of agent networks and next-gen CRM.

Rory O'Driscoll, enterprise software investor and market strategist; Jason Lemkin, SaaS founder and investor behind SaaStr. They dissect Anthropic's security product and market shock. They debate whether agents will shrink SaaS incumbents and if consumer delegation can replace services like DoorDash. They unpack Citrini's "ghost GDP" idea, Figma's AI-powered rebound, public stock picks, and Jack Altman joining Benchmark.

Join Brian Halligan, co-founder of HubSpot, Rory O’Driscoll from Scale Venture Partners, and SaaStr's Jason Lemkin as they unpack the eyebrow-raising IPO mispricing of Figma. They discuss why founders crave a stock pop despite the risks and the complexities of CEO compensation. The trio also breaks down Meta's strong quarter, the mammoth $15B valuation of Cognition, and the implications of Ramp’s $22B funding round. Dive into the evolving tech landscape and the future of venture capital in a candid, insightful conversation.

Rory O'Driscoll, veteran SaaS-focused investor; Jason Lemkin, SaaS scaling expert and founder of SaaStr. They debate Anthropic's $30B raise and AI funding frenzy. They unpack why AI narratives crush SaaS stocks, where AI is actually eating (coding, support, legal), Figma's missed AI adjacencies, Stripe versus Adyen, OpenClaw/OpenAI moves, and why mega private funds like Thrive keep growing.

Jason Lemkin, a seasoned SaaS entrepreneur and founder of SaaStr, joins Rory O'Driscoll, a venture capitalist with a knack for enterprise investing. They dive deep into Anthropic's impressive $10B fundraising and its implications for valuation and IPO prospects. The duo debates whether Claude has outperformed Cursor in the AI API landscape and explores the existential risks facing OpenAI. They also analyze the dynamics of venture capital, pondering if the middle market is fading as boutiques and mega-funds thrive.

In this engaging discussion, Jason Lemkin, SaaS entrepreneur and founder of SaaStr, and Rory O'Driscoll, a seasoned venture capitalist, delve into their predictions for 2026. They highlight Dario Amodei as a standout founder and discuss the impact of companies like Salesforce and Databricks. The duo explores the biggest surprises of 2025, including talent wars, and share insights on top tech stocks to watch. They also debate the potential impacts of AI on employment and speculate on upcoming IPOs, making for a thought-provoking and entertaining conversation.

Rory O’Driscoll, venture investor offering market and M&A perspective. Jason Lemkin, SaaS investor known for deep startup and public markets analysis. They dissect Brex’s $5.15B sale and its ripple effects, debate Anthropic’s soaring inference costs and AI metering, unpack OpenEvidence’s $12B raise, and evaluate recent IPO performances and what they mean for scaling SaaS.

Jason Lemkin, a seasoned SaaS investor, and Rory O'Driscoll, an experienced venture capitalist, dive into the multi-billion dollar investment Anthropic secured from Microsoft and NVIDIA. They discuss the implications of Sam Altman's 'War Mode' memo at OpenAI, questioning whether it's effective or just hollow rhetoric. The conversation also explores NVIDIA's customer concentration risks, and whether hyperscalers should build their own chips. They analyze the rapid growth of Sierra and Lovable, discussing their valuations and market strategies amidst the evolving AI landscape.

Join Jason Lemkin, a SaaS investor known for his impressive portfolio including Algolia and Talkdesk, and Rory O'Driscoll, a General Partner at Scale, as they dissect the evolving landscape of venture capital. They discuss why seed investing may be misguided and the increasing risks of venture capital today. The duo explores insights on a16z's hefty $20BN fund, the strategy genius of Josh Kushner, and the ethical challenges in B2B practices, all while navigating the delicate balance between opportunity and caution in a shifting market.

Jason Lemkin, SaaS investor and SaaStr founder, and Rory O'Driscoll, VC partner and macro commentator, dig into Anthropic vs the Pentagon, the politics around AI deals, OpenAI's $110B financing structure, valuation premiums for founders, Block's 40% layoffs and whether AI or overhiring caused it, and Cursor hitting $2B ARR plus the pace of agent-driven product change.