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  2. The Grittiest Conversations of 2025: AI, Business & Beyond
The Grittiest Conversations of 2025: AI, Business & Beyond

The Grittiest Conversations of 2025: AI, Business & Beyond

Grit · Dec 29, 2025

Leaders from Carlyle, HubSpot & more discuss AI's impact—reshaping work, web economics, and the future of enterprise tech and AR glasses.

Carlyle's David Rubenstein Stays Politically Neutral to Maintain Bipartisan Influence

Rubenstein avoids political donations to prevent being blamed for politicians' actions, avoid accusations of buying access, and maintain the ability to bring Democrats and Republicans together for high-level initiatives.

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The Grittiest Conversations of 2025: AI, Business & Beyond

Grit·3 months ago

Big Tech’s Massive AI Spend Is a Defensive Bet Against Irrelevance

During a technology shift like AI, if the trend proves real, companies that failed to invest risk being permanently left behind. This forces giants like Microsoft and Meta into unprecedented infrastructure spending as a defensive necessity.

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The Grittiest Conversations of 2025: AI, Business & Beyond

Grit·3 months ago

Mailchimp Founder: Tech Reinvention Cycles Have Shrunk From 3 Years to Months

Ben Chestnut observed that the cadence for tech companies to reinvent themselves has accelerated from every three years to a constant, rapid cycle. This makes it nearly impossible for large, established companies to remain nimble in the AI era.

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The Grittiest Conversations of 2025: AI, Business & Beyond

Grit·3 months ago

HubSpot's Yamini Rangan: AI's True Value Is Boosting Customer-Facing Time

For 20 years, sales reps have spent only ~25% of their time with customers. AI is the first technology that can fundamentally shift this ratio by automating low-value prep work, rewriting the nature of go-to-market jobs.

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The Grittiest Conversations of 2025: AI, Business & Beyond

Grit·3 months ago

Frontier AI Models Now Require Niche Experts, Not Generalists, for Training Data

AI models have absorbed the internet's general knowledge, so the new bottleneck is correcting complex, domain-specific reasoning. This creates a market for specialists (e.g., physicists, accountants) to provide 'post-training' human feedback on subtle errors.

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The Grittiest Conversations of 2025: AI, Business & Beyond

Grit·3 months ago

Snap's Spiegel: AI Turns AR Glasses into Portable Multitasking Workstations

AI accelerates AR glasses adoption not by improving the display, but by changing how we compute. As AI agents operate software, our role shifts to monitoring, making a portable, multi-screen AR workstation more useful than a single-task phone.

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The Grittiest Conversations of 2025: AI, Business & Beyond

Grit·3 months ago

Legal AI Startup Harvey Builds Its Moat by Tackling Problems Models Won't Solve for 10 Years

Harvey intentionally avoids self-serve and focuses on the most complex enterprise legal work first. The strategy is to build a business around problems so difficult they will outlast the next decade of foundational model advancements, preventing commoditization.

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The Grittiest Conversations of 2025: AI, Business & Beyond

Grit·3 months ago

Cloudflare's Zatlin: AI Crawlers Increase Publishers' Costs While Cannibalizing Their Traffic

Publishers face a dual economic threat from AI: their cloud costs increase as bots scrape their sites, while their revenue-driving human traffic declines because users get answers directly from AI chatbots, breaking the web's core business model.

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The Grittiest Conversations of 2025: AI, Business & Beyond

Grit·3 months ago