Summary:
Our 24/7 Wall St. Analyst Doug McIntyre has some serious questions about why Alphabet recently issued a 100-year bond. Fortunately, his co-host, Lee Jackson had some insight.
“It is all about AI and data center funding and things of that nature,” Jackson explained.
Among the reasons that this rare move has so many tech investors concerned is that it’s a move that hasn’t been seen since 1997 with Motorola, just before the dot-com bubble burst.
Jackson warns that investors are beginning to worry about heavy capital expenditures and declining free cash flow among major technology companies, including Meta.
“I think people need to tread carefully now because investors are starting to get worried about this,” says Jackson. “As we have discussed, Michael Burry is long Nvidia puts, long Palantir puts, and he is also long GameStop. This is going to be interesting because these companies are going to have to fund all of this themselves. Technology stocks used to generate enormous free cash flow, but a couple of them are not going to have free cash flow this year, and Meta is one of them.
Jackson and McIntyre suggest that investors be cautious, particularly regarding volatile technology stocks such as Oracle and even mega-cap names that may trade sideways in the near term.
Transcript:
Doug McIntyre: So Lee, for reasons I honestly cannot understand, Alphabet issued a 100-year bond. I looked at it carefully, including the interest rates and the prospectus. I am going to ask you this because I have no idea, having looked at it – why?
Lee Jackson: AI funding. It is all about AI and data center funding and things of that nature. The thing that is kind of scary about this, and you will remember this because you were around a generation ago on Wall Street while I was, is that the last company to do a 100-year bond was Motorola (NYSE: MSI) in 1997. That was just as the dot-com boom was starting to explode higher, which was obviously a harbinger of not good things to come. I thought that was interesting because I knew there were only one or two of them. Some of the tobacco settlement bonds were 50-year bonds, and maybe they had 100-year ones. I did some research and Motorola did it, and we know how things went for Motorola from 1997 on.
Doug McIntyre: I think they just wanted to get their name in the newspaper.
Lee Jackson: Who? Motorola?
Doug McIntyre: No, that already happened to them. I think Alphabet (NASDAQ: GOOGL) | GOOGL Price Prediction just wanted to get their name in the newspaper or something other than Gemini.
Lee Jackson: They are putting all this funding toward AI. They have gotten to the point where you cannot fund all of this with private credit and you cannot just move money from one pocket to another. I think Wall Street and the broader economic and financial community are starting to look at everything very carefully. That is why we have had this huge rotation out of stocks. One of the top sectors so far in 2026 is energy. That is a clear rotation because it horribly underperformed last year and the year before that.
I think people need to tread carefully now because investors are starting to get worried about this. As we have discussed, Michael Burry is long Nvidia puts, long Palantir puts, and he is also long GameStop. This is going to be interesting because these companies are going to have to fund all of this themselves. Technology stocks used to generate enormous free cash flow, but a couple of them are not going to have free cash flow this year, and Meta Platforms (NASDAQ: META) is one of them.
Doug McIntyre: Some of these companies are spending north of $150 billion this year.
Lee Jackson: Yes, it is huge. This does not smell good to me. It reminds me of the late 1990s when stocks were opening up 200% on their IPOs. Slowly but surely things blew up. We almost went down in flames in 1998 when one of the biggest firms blew up. The question is whether we are nearing that point again or whether we are too close to it to see clearly.
Doug McIntyre: I think some of the big companies that want to have IPOs may have to delay them. If the market stays sideways for two or three months or starts to sell off, some of these large IPOs people are talking about for mid-year may have to be pulled. People say IPOs never get pulled, but they do. Companies can be weeks away from going public and then decide to stay private for a while.
Lee Jackson: The firm I was referring to was Long-Term Capital Management. It almost blew up Wall Street single-handedly. If they had not stepped in with coordinated support from the banks, it would have been very bad. We are already starting to see private credit worries. I think everyone watching this should be careful this year. We have had three strong years, and a 100-year bond has not been issued since 1997 and may not be seen again for decades.
Doug McIntyre: If I were an investor right now, I would look at companies like Microsoft (NASDAQ: MSFT) and say that near term they are not going up. They may not drop precipitously, but those stocks are likely sideways to down. The one company I am really nervous about, and I would sell now if I owned it even though it is already down a lot, is Oracle (NYSE: ORCL). Oracle has already taken a beating, and I think that beating could get worse.
Lee Jackson: Oracle has taken wild swings. It was over 300 in the summer, then it got hammered, then it came back, and then it got hammered again. The question is whether everything is so tied to their AI and data center spending that they have lost track of everything else.
Doug McIntyre: People need to remember that Oracle is not a huge company compared to the very largest tech names. It is not small, but it is not Microsoft, Alphabet, or Meta. That means it carries real risk because its sales and cash flow are not as large as those bigger companies.
Lee Jackson: The next time somebody issues a 100-year bond, we will be right back to let everyone know.
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