ACQ Sessions: Jason Calacanis

Key takeaways

• Jason Calacanis emphasizes the importance of impact and legacy over pure wealth accumulation—prioritizing doing meaningful work that excites and fulfills.
• Podcasting has become a powerful medium for education, influence, and building a personal brand that fosters intimacy and loyalty among listeners.
• The democratization of venture capital, through transparency and broad participation, is a game-changing trend Jason actively supports.
• Building community and relationships is fundamental in technology and investing, creating impact that lasts across generations.
• Success in the industry is driven by impact on the game, mentorship, and fostering new generations of founders and investors.
• Jason advocates for recognizing pioneers in VC with a Hall of Fame, celebrating impact and legacy rather than just financial returns.

Summary

Sponsors

• Anthropic · We are working with Anthropic, which used to have some older infrastructure monitoring that was in place, but at their massive scale and complexity, they adopted Century to help them find and fix issues faster. Century detects bad hardware early, debugging massive issues in hours instead of days, and helps track exceptions and analyze failures across all primary languages used by Anthropics research teams. They also have an AI debugger called SEAR that roots out gnarly issues and proposes fixes.
• Sentry · We are working with Sentry, which helps developers debug errors and latency issues across their software. Sentry's platform allows organizations like Anthropic to monitor exceptions, assign errors, and analyze failures in real time, with support for multiple languages and environments.
• WorkOS · We are partnering with WorkOS, the enterprise-ready platform used by OpenAI, Cursor, Perplexity, Vercel, and others. WorkOS makes it easy for startups to implement enterprise authentication features like SAML2.0, user provisioning, permissions, and audit logs—turning complex requirements into drop-in APIs. It enables teams to implement enterprise-ready security in minutes and handle global, remote workforces seamlessly.
• Statsig · Statsig offers powerful feature gating, A/B testing, and analytics, allowing teams to release features confidently and measure their impact—integrating seamlessly into development workflows.