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  1. TBPN
  2. Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN
Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN

TBPN · Apr 23, 2026

Thoma Bravo's massive Medallia loss, OpenAI's new GPT-5.5, and Bob Iger's return to Thrive Capital.

Blackstone Credits Medallia's Failure to Poor Sales Execution, Not AI Disruption

Contrary to the popular narrative, a major lender, Blackstone's head of private credit, publicly attributed Medallia's underperformance to "execution-driven issues." This was supported by reports of salespeople hitting only 20% of their quotas, highlighting that basic business fundamentals remain critical amid technological shifts.

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN thumbnail

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN

TBPN·10 hours ago

Competing AI Labs Secretly Collaborate to Detect Nation-State Distillation Attacks

Despite being fierce competitors, major AI labs work together behind the scenes. They share intelligence on suspicious API usage from shell companies to identify and thwart large-scale, coordinated distillation attacks from foreign adversaries, which might otherwise go undetected by a single lab.

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN thumbnail

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN

TBPN·10 hours ago

Thoma Bravo's $5.1B Medallia Loss Shows Peril of High-Leverage SaaS Buyouts

Medallia's failure wasn't just AI disruption. It was a perfect storm of a $6.4B private equity buyout loaded with floating-rate debt, rising interest rates that ballooned payments, and poor internal sales execution. The AI threat simply accelerated an already precarious situation.

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN thumbnail

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN

TBPN·10 hours ago

Disney's Bob Iger Joining Thrive Capital Signals New Trend of Operator-led VC

Bob Iger's return to Thrive Capital exemplifies a growing trend of retired titan CEOs from major corporations entering venture capital. These figures bring deep operational experience and unparalleled networks, offering a distinct advantage and a new model for VC firm value-add beyond just providing capital.

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN thumbnail

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN

TBPN·10 hours ago

OpenAI's GPT-5.5 Launch Focuses on Autonomous Agents, Not Just Better Chat

The GPT-5.5 announcement emphasizes its role in "powering agents built to understand complex goals, use tools, check its work and carry more tasks through to completion." This signals a strategic shift from merely improving conversational AI to building autonomous systems that can execute complex, multi-step workflows.

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN thumbnail

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN

TBPN·10 hours ago

Wired Founder Kevin Kelly's 2015 "Cognifying" Prediction Accurately Foresaw Today's Cloud AI Boom

Years before the Transformer architecture became dominant, Wired founder Kevin Kelly's book predicted "cognifying"—making everything smarter using "cheap, powerful AI that we get from the cloud." This demonstrates how focusing on fundamental technological forces, rather than specific implementations, can lead to remarkably accurate long-term predictions.

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN thumbnail

Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN

TBPN·10 hours ago