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John Coogan
Foreign. We're going to get that sound ready because we got some bad news. Thoma Bravo is taking a massive write down on a software company called Medallia. Thoma Bravo is reportedly handing over the software company Medallia to creditors after restructuring negotiations failed to materialize. This is a $5.1 billion equity wipeout for the firm who bought the business for 6.4 billion in 2021. There's some background in Reuters that I think I should read through and then can you sort of give me your analysis and your and what you're seeing on the timeline around take so from Reuters exclusive. Thoma Bravo nears agreement to turn software firm Medallia over to creditors. That does not sound good. Private equity firm Thoma Bravo is nearing an agreement to hand over software firm Medallia to lenders, wrapping up months of restructuring negotiations. The move will wipe out 5.1 billion in equity. Medallia has struggled in recent months under the weight of $3 billion of debt which it owes to Blackstone, KKR, Apollo Group and Antares Capital. Thoma Bravo, Blackstone and KKR decline to comment. Apollo and Medallia didn't immediately return. Quest for comments to Reuters. So, like other software companies, Medallia's valuation has been hit in recent months over concerns that its services will eventually be supplanted by artificial intelligence. What does Medallia do? Medallia provides software that collects and analyzes customer and employee feedback for companies. We've had some startups, some of them backed by Sequoia Capital, that are using AI to do this exact thing. That's potential disruption. And then there's also.
Brandon
So their main rivals, Qualtrics. Yep, but yeah, and maybe you said this already, but you know that Sequoia was one of the big backers at Medallion.
John Coogan
I didn't know when they were a private company. Oh, interesting. So, I mean, they're still private, but there's a long history of that with the firm. That was before Zenefits was called like SuccessFactors. Lars Dalgard did that deal. Sequoia is the real winner here.
Brandon
They did 35 million in 2012, they did another 50 million in 2014, and then they later led $150 million round.
John Coogan
Wow. And then eventually did they take it public or did they sell it for 6 billion to Thoma Bravo directly from the private. Was Medallia ever a public company? That would be interesting.
Brandon
I think they were.
John Coogan
You look that up and I will keep reading from this to give some more backstory. So private equity firms invested heavily in the software sector when interest rates were low. Following the peak of the COVID 19 pandemic, we all remember 3% interest rates. It was the golden era of startups and growth. All the DCFs were massive and then of course the valuations came down once the interest rates were went up. So investors have become increasingly nervous about the sustainability of high valuations assigned to some of those assets and the debt raised to buy them. If you're on a floating rate, these firms are not necessarily backed by a 30 year fixed mortgage like your house. Your interest rate went up and the debt payments ballooned. And if the cash flow from the business has not also ballooned, you could be in trouble like this company potentially is. Blackstone, KKR and Antares hold some of the debt in traded and non traded funds. FSKR Capital Corp. Marked the debt at 79 cents on the doll in its last quarterly report. And of course debt is senior to equity. So what does that mean for the equity? Not good. And that's why this deal is happening. Apollo Debt solutions market at $0.74 on the dollar. So a question about can they even recover, you know, the full value of that debt? The equity is obviously in deep deep trouble. So Blackstone's global head of private credit, Brad Marshall said on a conference call in February that Medallia had been quote underperforming not because of anything related to AI but due to what we believe to be execution driven issues. So there is a question of well if they restructure and this company gets in the hands of creditors, maybe they can roll out AI features and become an AI winner and accelerate the top line and restructure the debt.
Brandon
I saw someone was sharing that there were, there were some sales people doing kind of some anonymous reporting and saying a lot of the reps were struggling to hit quotas like basically delivering like 20% of quotas. So just basically getting out competed in the. Sure, yeah. And just go back to the earlier point. Yes. Medallia went public in 2019 on the nice was taken private 7-26-2021.
John Coogan
Okay.
Brandon
It had been trading around the $5 billion mark prior to the take private at 6.4.
John Coogan
So Thoma Bravo after taking it private installed a new leadership team in early of 2025. Marshall, the head of Blackstone's global head of private credit said that they were working on a turnaround plan and we expect there to be discussions around the capital and so people are blackpelling on the timeline. Brandon says yes, I am sure this is the bottom in software and we won't get worse from here. Not good signs this is, you know, potentially one of those cockroaches that Jamie Dimon is worrying about. There's another post that seems like it was deleted.
Brandon
But yeah, I mean, some of the screenshot here, the tough thing is that everyone involved here has been on a kind of a press tour saying, like, everything's fine.
John Coogan
Yes.
Brandon
Like we're all good. Yes, AI is going to be an accelerant. But even ignoring the AI question, a lot of these businesses no longer have, you know, are founder led. They're competing against other companies that, that are founder led. And yeah, it's, it's just kind of credit to Jamie Dimon for his comments saying, like, you know, I don't think this is over. When you had first brands and some other shutdowns.
John Coogan
Yeah. In the previous startup era there were, I mean, I feel like it would have been hard to raise for just like a vanilla Qualtrics or Medallia competitor and just saying like pre AI, like we're just going to build SaaS and we're just going to build a crud app and write software.
Brandon
Yeah. A new player is a company. Aru.
John Coogan
Yeah, that's a very different approach.
Brandon
Simulation.
John Coogan
Simulation. Yeah, that's a very different approach.
Brandon
And then we had another one. I'm blanking on the name. It was a YC founder key. He had gone through YC a few years ago, but his company is taking off doing something similar. So people have been well aware of the opportunity that Medallia and Qualtrics have owned.
John Coogan
Yeah. But in other debt related news, Xi Jinping wants to use the International Monetary Fund to rescue the array of distressed Chinese loans around the world. This is an interesting piece from the Wall Street Journal opinion. Noah Smith is laughing. He says, lol, belt and road failed so hard. Xi Jinping is incompetent. That is, this is very narrative.
Brandon
Do not go to China. Yeah, do not go to China.
John Coogan
Yeah. This is an interesting thing, but maybe a potential bargaining chip. In all of the other discussions, you know, in tech, Tyler always points out that tech is like too focused on chips when it comes to Chinese diplomacy. That there are many, many other questions around trade and what Apple's doing and rare earths. And there are so many and just the broad history of the Chinese empire that play into what their Taiwan policy is, how they will interact in the Middle East. And we tend to focus it all on AI. It's all about the data centers and the chips and perhaps there are more things. And this is one example of something else that is a key factor in a broader Negotiation that includes chip exports and also rare earths and also talent movements and whether or not Manus will be able to move over to Meta and a million other things. And so that is the job of these world leaders is to swirl around all the different trade offs and get to hopefully a good deal for both sides.
Brandon
Some breaking news. GPT 5.5 is out.
John Coogan
Oh, it is.
Brandon
Is out. Introducing GPT 5.5, a new class of intelligence for real work and powering agents. Built to understand complex goals, use tools, check its work and carry more tasks through to completion. It marks a new way of getting computer work done. Now available in ChatGPT and Codex.
John Coogan
I like this demo of the Rubik's Cube. GPT 5.5 excels at writing and debugging code, researching online, analyzing data, creating documents and spreadsheets, operating software and moving across tools until a task is finished. GPT 5.5 delivers this step up in intelligence without compromising on speed matches. GPT 5.4 per token latency in real world serving. There's the model card there and there are some other posts.
Brandon
We will wait for the reactions to come in, we'll gather them, we'll summarize them. But the team cooked.
John Coogan
Cooked. Congratulations to everyone that worked on this.
Brandon
Let's head over to Merriam Webster. Jon, what do you got?
John Coogan
Merriam Webster added a new word to the dictionary, I believe. And I feel like the. Actually, I don't know, I mean.
Brandon
Okay, so they have a slang section.
John Coogan
Okay. Slang and trending. They must be working overtime over there because the number of wombos. If you're not familiar with wombos, these are word combos. Things like queen. Lorraine, the lore. Explain. Or queen.
Brandon
I could tell John, can you Lorraine GPT 5.5.
John Coogan
Yes. Give you the lore and tell you about what happened with 4.5, 4. Oh, 3.5, 3. Da Vinci, give you the whole lore. But then also explain what this model is capable of. That's the full lorraine of GPT 5.5. But we're not here to talk about Lorraine. We're here to talk about chapelganger, which is a new word in Merriam Webster, the dictionary. It's basically the main dictionary as far as I'm concerned. Chapelganger is a term for a less attractive version of someone or something. So whoever's going out there and distilling 5.5 into sort of a chopped version of it, that will be the chapel ganger of the official GPT 5.5. So stay away from the chapel gangers unless you're Unless you're really down, you're lucky and you just, you need, and you need a Chinese open source model to do something for you, then, you know, buyer beware because it might, it might have some flaws. Separately, there is, there is new news from Michael Kratzios that the government seems to be taking anthropic and OpenAI's messaging around distillation very seriously and is setting up a task force. We can read a little bit more about this later, but setting up a task force to actually figure out how to prevent distillation at scale. As the models get bigger, it's more and more of an economic impact. When you're talking about, you know, $100 million training run and a Chinese lab can distill it and sneak the weights out and sneak the, you know, exfiltrate the data. That's a lot different of an economic impact from stealing something that, I don't know, cost billions to train or billions to put together. Good news there, hopeful, hopefully they're successful. It was also sort of a white pill to see a lot of the labs working together to understand, hey, we're seeing this weird amount of data go to this particular company. Are you seeing the same thing? Or it's a shell company and we have five shell companies in these areas that are asking for these queries. And then the other lab says, oh yeah, we're actually getting something similar. And if you puzzle piece those together, all of a sudden you're getting a really solid map of what a frontier system is capable of. And so it feels like we the industry are the victim of a distillation attack, even if it might not register among a single lab because that single lab is only getting hit with like one third or one fifth of the total attack subject.
Brandon
Adversarial distillation of American AI models the United States leads the world in AI technologies. That lead reflects decades of foundational research. Bold entrepreneurial risk taking in hundreds of billions of dollars in annual private investment. American AI leadership drives economic growth, strengthens national security and advances the front of science, medicine and human knowledge. The breakthroughs emerging from American industry raise living standards, expand opportunity and improve lives around the world. However, the United States has information indicating that foreign entities, principally based in China, are engaged in deliberate industrial scale campaigns to distill US frontier AI systems. Leveraging tens of thousands of proxy accounts to evade detection and using jailbreaking techniques to expose proprietary information. These coordinated campaigns systematically extract capabilities from American AI models exploiting.
John Coogan
I don't like that. That sounds bad at all.
Brandon
Exploiting American expertise and innovation.
John Coogan
Every AI researcher needs this button on their desk. If they detect a distillation attack, fire it off and the security team will come and make sure you're locked down. And it does seem like overall, all the labs are being more careful about how the APIs roll out, how they're doing KYC, how they're doing different partnerships and stuff. And I think it's all a back and forth and a dynamic. But it's fun that this new model is available and people will play with it and I'm sure we'll see some cool stuff. Some.
Brandon
Yeah. And Quinn 3.6 rolled out yesterday. People are like, wow, it's almost as good as Opus 4.5. Because they distill.
John Coogan
Don't ask.
Brandon
Anyways, I'm glad that Kratzios is on it and I'm glad that the labs can coordinate and work together on this one.
John Coogan
Yes.
Brandon
More breaking news.
John Coogan
Yes.
Brandon
And unfortunate. But we had talked about this previously. Meta is cutting 10% of their workforce, which is 8,000 employees.
John Coogan
But this has been for a while,
Brandon
eliminating 6,000 open roles.
John Coogan
Yeah, I saw Microsoft was doing something similar. They're offering early retirement to something like 7% of the workforce. Trying to lean out a little bit. I'm sure the debate will continue to rage over the underlying motivations. These companies can be big, and sometimes maybe they're too big. Maybe there's AI gains, maybe there's different investment strategies. We will have to see where they are moving chips around, what projects they are actually cutting, what projects they are doubling down on, because these companies are also hiring at all times, effectively. Well, Christoph had some actual media ideas for the tech industry. He says there's not enough. Enough media in tech. You see, we need more tech, positive media for sure. So he says, silent Library with founders, winner gets investment.
Brandon
What is Silent Library?
John Coogan
Silent Library. So you're. Is this like a. Like a webcam that observes?
Brandon
Silent Library is a television show. It had four seasons. It's a game show.
John Coogan
Oh, it's a game show. Game shows are fun. I can see a game show being. Being fun. At least different.
Brandon
And it was six friends vying for a cash prize. If only they can remain silent as one of them is forced to endure a bizarre stunt while seated in a library.
John Coogan
Okay, okay.
Brandon
What else? Jackass with founders.
John Coogan
What does that mean? How do you make that tech related? Maybe like humanoid robots. Like I. When I think of Johnny Knoxville, I just think of riding bull riding effectively. And so I imagine like riding some sort of, you know, Robotic bowl would be it, but, you know, it's very dangerous. Like, the team that worked with, like Dan Margera and Johnny Knoxville, they had some serious injuries from time to time. And I don't know if it's in your best interest to be a founder and be like, yeah, I need to launch my startup, so I got to go in the ring with a mechanical bull and potentially break my arm and not be able to code and. Seems rough, but would be entertaining. And with the right twist, I believe it could work. Interview founders while going ghost hun. I feel like paranormal tech content. Jesse Michaels doesn't get enough credit here. You know, he is a technology. It's in the technology charts and it charts high, like it's up there. And he has an incredible pedigree, great investor and also, you know, has some of the best reporting on aliens and paranormal activity and conspiracy theories. And I guess he just hasn't cracked the way to bring a founder along. But if you're. If you're friends with Jesse Michaels, are in touch, maybe you just tag along for little cameo on one of his videos and that's all the PR you need.
Brandon
Founders give their pitches while skydiving. Can you.
John Coogan
I like skydiving.
Brandon
Can you talk while skydiving?
John Coogan
With the right headset.
Brandon
Have you gone skydiving?
John Coogan
No, but I like the idea and I like the videos.
Brandon
Have I told you the story where I was? I was on an overnight flight back from Europe.
John Coogan
No.
Brandon
I'm sitting on a. On a plane.
John Coogan
Yeah.
Brandon
And I'm awake. I can't sleep. Okay. And out of the shadows, John Wick. Oh, walking up the aisle.
John Coogan
Keanu Reeves. Yeah.
Brandon
Sitting there. It's effectively like 2am And Keanu Reeves is like, walking at me on this plane in the middle of the night.
John Coogan
Yeah.
Brandon
We ended up talking for like five minutes.
John Coogan
Really?
Brandon
It was cool.
John Coogan
That's cool.
Brandon
He went and then went back to his seat and.
John Coogan
Yeah, well, he stayed on the plane. He did not.
Brandon
Super, super nice guy.
John Coogan
What else do they have here? SF party. I'm schmacked. Videos. I don't know. I'm schmacked.
Brandon
Wow. Unk, you're unk, you get. You guys know I kind of remember, but you remember. I need to remember. Basically, this was this whole, like, you could call it a media company, but it was really like a guy that would make party videos.
John Coogan
Okay, what era are we talking to every college?
Brandon
Okay, so it was really popular. Probably 2010 to pre. Now 2013.
John Coogan
Okay. Okay.
Brandon
And I will say a lot of people use these videos As a sort of college guide.
John Coogan
Okay. Okay.
Brandon
So not to be sure, they have millions and millions of views at this point.
John Coogan
Yeah. Kevin Kelly, the founder of Wired, had some incredible predictions in 2016. Let's read through them. Summary of the inevitable. Understanding the 12 technological forces that will shape our future. This was Kevin Kelly's book from 2016. According to Kelly, much of what will happen in the next 30 years is inevitable. The future will bring with it even more screens, tracking and lack of privacy. In the book, he outlines 12 trends that will forever change the ways we work, learn and communicate. Becoming moving from fixed products to always upgrading services and subscriptions. That has definitely happened. We're moving away from even seats. Everything's consumption based now. Cognifying. Making everything much smarter using cheap powerful AI that we get from the cloud. Nailed it.
Brandon
That is glowing. Fantastic prediction for assuming he wrote it. He actually wrote it probably in 2015. Published in 2016.
John Coogan
But he's the creator of Wired. He's been tapped into tech his entire career. Depending on unstoppable streams of real time for everything for sure. Turning all surfaces into screens that definitely happen. Your toaster can watch screening TV now. Shifting society from one where we own assets to one where instead we have access to all services at all times. Collaboration at mass scale. On my imaginary sharing meter index, we are still 2 out of 10. Filtering, harnessing intense personalization in order to anticipate our desires. Remixing, unbundling existing products into their most primitive parts and then recombining in all possible ways. That's definitely happening. Coconut Simulator unironically an example of that. Interacting. Immersing ourselves inside of computers to maximize their engagement. Tracking. Employing total surveillance for the benefit of citizens and consumers. Sounds scary. Potentially a good outcome if things are done properly. Promoting good questions is far more valuable.
Brandon
Answers what you think total surveillance is potentially.
John Coogan
Well, he says total surveillance for the benefit of citizens and consumers. So if there is a black box where my Netflix recommend, where my Netflix activity exists, where no Netflix employee can see it because it's encrypted, but it can make great recommendations and recommend me the next great show that I will actually enjoy, I'm cool with that.
Brandon
Surveillance for the benefit of John Coogan.
John Coogan
Yeah, yeah, there is. There is a surveillance bull case. Constructing a planetary system connecting all humans and machines into a global matrix. Okay, that one we're still waiting on. But a lot of good interesting predictions. Jason Schumann says wild how accurate these predictions were and they were in fact, well.
Brandon
More breaking news in the Journal. Bob Iger is Returning to where Disney Thrive.
John Coogan
Thrive. No way. That's amazing.
Brandon
Back to Thrive.
John Coogan
Love it.
Brandon
Yeah, I think he's been an LP in Thrive. He also bought a piece of Thrive.
John Coogan
Yeah, that's right. Okay, well, that'll be a good next act for him. I'm very interested to see where he goes. There's a whole alumni class coming together. Reed Hastings is out and on to the next thing. We'll see where they go, hopefully.
Brandon
Back to Intel. Intel announced its first quarter earnings after the bell on Thursday, beating analysts expectations on the top and bottom line and providing better than anticipated Q2 guidance on strong data center sales. Intel said it expects revenue of 13.8 to 14.8 billion for the second quarter. Wall street was anticipating 13 billion and as of this morning they were at around 100. 100 times pe and so only up for Intel.
John Coogan
Climbing the ranks. Climbing the ranks. Tesla also released Q1 earnings revenue of 22.4 billion versus 21.4 billion estimated. So they beat on top line. They also beat on net income 1.45 billion versus 1.17 billion estimate. The interesting article in the Journal was that Elon was being more cautious about Tesla talking, saying, I think we need to get realistic about some timelines. So. So he is certainly not pumping everyone up and he's trying to sort of reset around the fundamentals and so we will see where that goes. It is a wild timeline that SpaceX, if it goes out at 1.75 trillion, will be bigger than Tesla, which is sitting around 1.1 1.2 trillion these days. So still both huge companies.
Brandon
Credit to Bubble Boy over on X two hours ago, he says, everyone asked me about how I'm playing earnings. He says, doubling down. 25% of my portfolio is in intel calls.
John Coogan
Wow. There we go. Bubble Boy. Congrats.
Brandon
Well done. Well played stuff. Well played.
John Coogan
Leave us 5 stars on Apple podcasts and Spotify. Sign up for our newsletter@tvpn.com Throw that flashbang Jordy, because we are out of here.
Brandon
It's been an honor.
John Coogan
It's been an honor.
Brandon
Thanks for hanging out with us and
John Coogan
we will see you tomorrow.
Brandon
We'll see you soon.
John Coogan
Goodbye.
TBPN: Thoma Bravo Loses Medallia, OpenAI Drops ChatGPT 5.5, Bob Iger Returns | Diet TBPN
(April 23, 2026)
Hosts: John Coogan & Jordi Hays
In this fast-paced Diet TBPN episode, John Coogan and Brandon (filling in for Jordi Hays) break down a tumultuous week in tech and business news. Key topics include Thoma Bravo’s massive $5.1 billion loss on Medallia following failed restructuring, the live drop of OpenAI’s GPT 5.5, major industry layoffs at Meta and Microsoft, Kevin Kelly’s eerily accurate tech predictions, and breaking news of Bob Iger’s next career move. Approaching each story with sharp analysis and a conversational, sometimes cheeky tone, the hosts provide insights on private equity, the evolution and security of AI models, shifting formulas in tech layoffs, and the future of tech media.
[00:00–06:14]
Details of the Deal:
Thoma Bravo is handing over Medallia to creditors after months of failed restructuring—a full equity wipeout on an initial $6.4B buyout, with $5.1B in equity erased. Medallia, which provides customer and employee feedback software, has struggled under $3B in debt and faces severe competition from AI-powered startups.
Timeline & Backers:
Sequoia Capital, a key early backer, invested multiple rounds. Medallia went public in 2019 before being taken private by Thoma Bravo (04:15), but market pressures, rate hikes, execution struggles, and the rise of AI competitors contributed to its downfall.
Insightful Analysis:
Notable Quote:
[06:14–07:45]
[07:45–11:31]
Model Highlights:
GPT 5.5 is positioned as a leap for “real work”—writing/debugging code, researching, analyzing data, completing multi-step tasks—with improved tools usage and task follow-through.
Reaction & Cultural Jokes:
Merriam-Webster Adds ‘Chapelganger’:
Explains and puns about “chapelganger”—a lower quality imitation—applied jokingly to “distilled” AI models vs. authentic GPT releases.
National Security & Adversarial Distillation:
[13:22–14:25]
[14:25–16:35]
Deliberate humor and riffing on TV concepts to make tech content compelling:
Memorable moment: Brandon tells a story about meeting Keanu Reeves on an overnight flight [16:33].
[17:02–19:49]
[20:09–22:18]
Bob Iger’s Post-Disney Career:
Intel & Tesla Earnings
With a lively, conversational style and sharp insight, TBPN’s John and Brandon pack this 22-minute “Diet” episode with analysis and banter—delivering actionable perspectives on private equity turbulence, the AI arms race, shifting fortunes in FAANG employment, and the recurring reinvention of the tech industry’s media landscape.
Whether you missed the news or want sharp context on each story, this episode’s rundown delivers both the facts and the “lore.”