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Meet the New Thiel Fellows, GPT 5.5, Thoma Bravo Loses Medallia | Victor Boyd, Alex Shieh, Nick Dobroshinsky, Ishan Gupta, Antoni Kiszka, Milan Lustig, Galen Mead, Aubrey Niederhoffer, Samuel Carvalho, Claire Wang

April 23, 2026

AI Summary

5 min read

Teal Fellowship Giga Stream, Medallia Wipeout, and GPT-5.5

Thursday's episode of TBPN was a packed news roundup combined with a "giga stream" of ten interviews with members of the new Thiel Fellowship class — but the episode opened with a piece of bad news for private equity: Thoma Bravo is handing over Medallia to its creditors in a deal that wipes out $5.1 billion in equity.

Thoma Bravo Loses Medallia

Thoma Bravo bought Medallia, a customer and employee feedback software company, for $6.4 billion in 2021 when interest rates were near zero. The company had gone public in 2019 and was taken private in July 2021. Now, after restructuring negotiations failed, Thoma Bravo is nearing an agreement to turn the company over to lenders. Medallia owes $3 billion in debt to Blackstone, KKR, Apollo Group, and Antares Capital. Blackstone's global head of private credit, Brad Marshall, said on a conference call in February that Medallia had been "underperforming, not because of anything related to AI, but due to what we believe to be execution driven issues." The hosts noted that Sequoia Capital was one of Medallia's backers when it was private, and that competitors like Qualtrics and newer AI-native startups like Aru are circling. The hosts framed this as a potential "cockroach" of the sort Jamie Dimon has been warning about — a private equity-backed software company that looked fi

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What you'll learn

  • 1 (00:00) **Show Open & Teal Fellowship Intro** - Hosts welcome viewers and introduce the Teal Fellowship GigaStream format: ten interviews with ten new fellows, each for roughly ten minutes.
  • 2 (02:15) **Thoma Bravo's Medallia Wipeout** - A deep dive into the $5.1 billion equity wipeout as Thoma Bravo hands over software firm Medallia to its creditors.
  • 3 (09:05) **Xi Jinping, IMF, and the Broader China Negotiation** - A Wall Street Journal opinion piece on China wanting to use the IMF to rescue distressed loans is discussed.
  • 4 (10:31) **GPT-5.5 Launch** - OpenAI releases GPT-5.5, a new model designed for complex agentic tasks.
  • 5 (12:23) **Merriam-Webster's "Choppelganger" & Anti-Distillation Task Force** - A new word is added to the dictionary, and the hosts cover the government's new task force to fight model distillation.
  • 6 (16:30) **Meta Cuts 10% of Workforce** - Meta is laying off 8,000 employees (10% of its workforce) and eliminating 6,000 open roles.
  • 7 (17:23) **Christoph's Tech Media Ideas** - A segment on Christoph's suggestions for new tech-positive media formats.

+ Full timestamped outline available in the app

Show Notes

  • (02:15) - Thoma Bravo Loses Medallia
  • (10:28) - GPT 5.5 Released
  • (11:32) - 𝕏 Timeline Reactions
  • (29:23) - Victor Boyd, co-founder and CTO of Cavalla Industries, discusses the development of autonomous forklifts aimed at delivering goods anywhere within hours. He explains the challenges faced with retrofitting existing forklifts due to their inconsistent internal designs, leading the company to build their own forklift to ensure reliability and scalability. Boyd also highlights the integration of teleoperation using Xbox controllers, allowing remote human intervention when necessary, and emphasizes the importance of delivering consistent results to customers, regardless of the level of autonomy achieved.
  • (41:03) - Alex Shieh, a former Brown University student and co-founder of The Antifraud Company, discusses his firm's mission to utilize AI models for detecting government fraud and pursuing legal action against fraudsters, operating on a contingency basis where they earn a percentage of recovered funds. He explains the company's approach of combining open-source intelligence with AI to proactively identify fraudulent activities, emphasizing the importance of outbound investigations over waiting for insider tips. Shieh also highlights the significant impact of fraud on taxpayer dollars and the necessity of restoring trust in public institutions through efficient fraud detection and recovery efforts.
  • (52:10) - Nick Dobroshinsky, the youngest-ever Thiel Fellow, has developed Every Ticker, a platform that utilizes large language models to generate high-quality research reports on all U.S. stocks, particularly focusing on small, mid, and micro-cap stocks often overlooked by Wall Street. He emphasizes that Every Ticker does not provide financial advice but instead aggregates and synthesizes research to help investors make informed decisions. Currently, the platform offers over 5,000 free reports, with plans to transition to a subscription model in the future.
  • (01:00:59) - Spirit Airlines Eyes $500M Rescue
  • (01:02:34) - Ishan Gupta is the Co-Founder and CTO of Juicebox, an AI-powered recruiting platform that leverages large language models to help companies identify and engage top talent. In the conversation, he discusses how Juicebox's AI agents analyze various data sources to find suitable candidates, reducing spam by targeting outreach more effectively. He also emphasizes the importance of job seekers showcasing their work through blogs, open-source contributions, and projects to enhance their visibility to AI-driven recruitment tools.
  • (01:12:55) - Antoni Kiszka is the co-founder of Perpetual, a company aiming to create a derivatives exchange for a wide range of assets. He discusses their initial focus on meme coins to test their technology, with plans to expand into traditional finance markets, including assets like hydrogen, which currently lack derivatives
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