Bill Ackman Says Stocks Are “Stupidly Cheap”

In this episode of Motley Fool Money, Motley Fool contributors Jon Quast, Matt Frankel, and Rachel Warren discuss:

• The bull and bear cases for AI and third-party platforms.
• SpaceX’s record-smashing IPO on tap.
• Bill Ackman’s comments on Fannie Mae and Freddie Mac.
• Value stocks our analysts like now.

To catch full episodes of all The Motley Fool's free podcasts, check out our podcast center. When you're ready to invest, check out this top 10 list of stocks to buy.

A full transcript is below.

This podcast was recorded on March 30, 2026.

Jon Quast: Billionaire investor Bill Ackman says stocks are stupidly cheap. I'm Jon Quast, and I'm joined today by Matt Frankel and Rachel Warren. We're going to get to Ackman's comments in a moment, as well as some news regarding the final frontier. But first, I wanted to hit this AI news. Is it friend or foe? Basically, here's the headline. Expedient Instacart stocks, otherwise known as Maple Bear, we're gaining a little bit in trading today after Jeffrey's analyst, John Cantone, said these were actually AI beneficiaries. Ordinarily, I wouldn't highlight the opinion of a single Wall Street analyst, but I was intrigued by these comments because it's very counternarrative. Basically, there are these platforms out there called third-party aggregators, and the prevailing narrative is that AI is bad for these platforms. But this analyst coming out and saying, Hey, this is actually a good thing for these two companies in particular. They're going to be beneficiaries. Rachel, I want to start with you here. Maybe explain what the demand aggregator business model is, and then elaborate on how AI could actually be a tailwind for these platforms.

Rachel Warren.: It's an important discussion. It really first to understand why AI might be a tailwind for the likes of Expedia and Instacart. It is important to understand what that demand aggregator model looks like. Essentially, these businesses win by sitting in the middle of this massive three-sided seesaw, if you will. They pull in a huge audience of consumers. That forces a fragmented group of suppliers, whether it be thousands of individual hotels in the case of Expedia or local grocery stores in the case of Instacart. It forces this group of suppliers to come to these aggregators to find customers. The mode is products they sell. It's that data. It's the convenience of having everything in one searchable place.

The fear that we've been hearing is that AI is going to fully disrupt this type of model, meaning maybe you would just ask a chatbot to book a flight. You'd skip the Expedia app entirely. But I think there's actually a meaningful bull case here to explore, and that's that AI actually makes the aggregator's data mot much deeper. You think about platforms like Expedia. You've got decades of high-intent search data that a general AI like ChatGPT doesn't have. They know exactly what you've swapped out, let's say, in the case of Instacart in your grocery cart when an item was out of stock or in the case of Expedia, which hotel filters you care about. AI allows these aggregators to turn that raw data into a concierge experience that's way more valuable than just a simple search.

I think AI can help these companies move from being more reactive to pro. Let's say you are looking for a place to stay, a hotel if you next vacation, instead of spending 20 minutes filtering for a family-friendly hotel with a gym near the beach, an AI-integrated platform could build that itinerary based on your specific history, maybe within seconds. I think if these aggregators execute the AI revolution correctly, they're not just going to stay relevant, but they could actually be able to more effectively manage those transactions from start to finish. That could mean higher conversion rates, higher retention rates. I think it's good news in the long run.

Jon Quast: That is really interesting and a very important thing to think about. But we do want to provide balance here. We want to provide both sides of the argument. Rachel's just given the more bullish AI third-party aggregator model narrative. Matt, I want you to counter this here. What are the reasons why investors are a little bit nervous when it comes to AI and these platforms?

Matt Frankel: I'm always the eternal optimist here, so I'm happy you put me on the Barcase for a change. Rachel mentioned this. It's the software disruption story. There's that general fear that conversational AI tools are going to be able to answer questions like, what's the cheapest flight from Charlotte to Los Angeles directly and without a need for an intermediary. To be fair, you can already do that. I use AI to find cheap flights all the time. It goes a step beyond that. The threats really evolved with the emergence of agentic AI. Which could potentially allow travelers to bypass any booking sites altogether and simply have an AI assistant that automatically finds and books the best flight, hotel, rental car, whatever for them for a trip, and just renders these useless. That's the bear case.

Jon Quast: We've looked at both sides of the argument here. It seems like there are merits to the bull argument. There are merits to the bear argument. I'm curious, though, what is your personal take on this? Where do you fall in this debate when it comes to what we're talking about here? Rachel, let's start with you.

Rachel Warren.: Actually do think I'm a bit more bullish on these platforms, and I'm not necessarily singling out IST card or Expedia Group as the best buys of the next decade, per se, but I do think some of these platforms, when you look at them at the end of the day, the AI is only as good as the data it's fed. A general chatbot can give you a great travel itinerary, a recipe, but it can't actually guarantee, for example, a hotel room that's available or ensure a bag of groceries ends up at your door. I know the vision is for AHS to do that in the long run. But I think the more realistic outcome, in many ways, will be that AI doesn't replace that infrastructure. It just makes it more efficient to navigate.

I think one example of this in action, a company I really like is Uber. People often think of the platform as a ride-hailing app, obviously a food delivery app, but they're the ultimate demand aggregator for mobility and delivery, and they already are using AI to process. Billions of data points on traffic, on writer intent, on courier efficiency in real time. Because they own the interface, they've got this, mass Network of drivers. AI has become a tool that makes their marketplace stickier and more profitable rather than a threat that replaces them. I don't think that will be the case across the board, but I also don't think we're going to reach a situation where all these aggregators and all these software different companies are just replaced by agents.

Jon Quast: That makes a lot of sense. If data is the mote here for these platforms, then Uber is definitely one with a lot of data and one to benefit. Matt, how about you? Where do you land on this?

Matt Frankel: I'm more on the fence. There's a lot to be said for things like loyalty programs, which many of these intermediaries offer, having human available customer service, which is something that, you know, as of now, ChatGPT and Claude haven't figured out how to replace. But there is a serious existential threat here, and it will be interesting to see how companies like Expedia and Instacart really react to it and use it to their advantage.

Jon Quast: I think that's fair. We don't always have to have our minds fully made up. We're still processing sometime, so I appreciate that. After the break, we're going to go to the final frontier. You're listening to Motley Fool Money.

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Jon Quast: Welcome back to Motley Fool Money with the Hidden Gems team. The countdown is on for the Artemis two launch on April 1st. This is going to take Astronauts around the moon. It's going to be the furthest distance that astronauts have ever been from Earth. But that's not the only space-related news that we have right now. SpaceX, maybe you've heard, is preparing to go public, and it's actually going to be the largest IPO of all time. You've heard us talking about it, but now we're getting reports that it's looking to raise a whopping $75 billion. That would value the company at 1.75 trillion. Rachel, what do you know about this?

Rachel Warren.: NASA is looking at the moon, Wall Street's looking at SpaceX. You're right about that expected valuation. It would be the largest IPO in history, aiming to raise $75 billion, as you noted, $1.75 trillion valuation at the top end. That would make SpaceX one of the top ten most valuable companies on the planet. If it achieved that valuation. This isn't really just based on launching rockets anymore. It's about this space tech and AI powerhouse that Musk is trying to build, and a big chunk of that trillion-dollar expected price tag would come from Starlink, which has scaled to millions of subscribers. It's already reportedly generating massive cash flow.

Another key factor in the business is the New StarCloud Initiative. Musk's idea is to put AI data centers in orbit using the natural vacuum of space cooling. It's a move that would combine satellite infrastructure with AI boom. Then, of course, the money from the IPO is reportedly earmarked to build out the Starship fleet to make those orbital platforms and eventually trips to Mars a reality. We will see how far that goes. SpaceX is reportedly planning to allocate up to 30% of the shares to retail investors, which is an unheard-of amount.

Now, important thing I want to note here trillion-dollar valuations leave very little room for error, and a lot of that expected price tag is based on future-state technology, like orbital data centers, Mars colonization ideas that haven't been fully proven out yet. If we see, for example, the AI and space narrative hit a snag or subscriber growth for Starlink slowdown, if the company reaches that premium valuation while public, we could see that compress quickly. That could have a real impact on those who bought the initial Pop. It's important to understand that as we go into an expected IPO, but I think there's going to be a lot of exciting news for investors to watch here.

Jon Quast: Man, I want to just circle back to some of the things that Rachel just mentioned. She mentioned how much money the company is looking to raise, but also mentioned how many shares are looking to be allocated towards retail investors. I wonder if you could just flesh that out for our listeners, just to tab.

Matt Frankel: Elon Musk knows this very well. One of the biggest things SpaceX has going for it as far as a giant IPO is a vast amount of retail interest. When you turn Tesla into a 400 X stock, and then you delay your biggest IPO for 10 years, you're going to build up a lot of retail interest. The plans to allocate 30% to retail, that compares to like 5%-10% for the typical IPO, and even that's higher than it used to be. It's not just that. There are several platforms that made it easier for companies to do this. SoFi prioritizes IPO access for everybody, RobinHood. There are a lot of different platforms. E-Trade is now owned by Morgan Stanley, which is one of the investment bankers reportedly on the deal. But even so, raising $75 billion in an IPO is no small task. The previous record is Saudi Aramco. That raised $29 billion, but I think it's fair to say that there's more investor interest for SpaceX than a giant Saudi oil company.

The 1.75 billion valuation it's not just the space business. Rachel alluded to this, too. Remember that Elon Musk recently merged XAI, which also owns the X platform formerly Twitter, into SpaceX. You're getting this emerging conglomerate here. Although XAI is almost certainly losing money. Starlink is profitable, as you mentioned, and XAI reportedly has a private valuation of well over $200 billion itself. There are some grand visions throughout these companies. Rachel mentioned the data centers in space. Elon Musk said he wants 1 million of those eventually. This sounds like the SpaceX version of Tesla's optimist robots. The real future technology and a big number that just raises eyebrows.

But having said all that, that valuation puts us really in uncharted territory for a US IPO, so I don't know what the implications could be. $75 billion is more than the entire IPO market in the US raised in all but two of the last 10 years, and those were the two COVID-booming years when everyone was going public. Once SpaceX's financials are released, which should come when we get a little closer to the IPO, we'll have a better idea of just how ambitious this valuation is, but right now, we honestly don't know.

Jon Quast: We'll keep an eye on it as it develops. You can definitely count on us for that. After the break, there's a billionaire investor out there who says that some high-quality stocks are really cheap right now. You're listening to Motley Fool Money. Welcome back to Motley Fool Money with the Hidden Gems team. We want to make you part of the conversation here. If you have a stock or an investing question for Matt, Rachel, myself, anyone else who is on the show regularly, you can now email us at podcast at fool.com. We would love to have mailbag segments whenever possible. Send in your questions, but remember, keep them foolish. That email again is podcast at fool.com, podcast at fool.com.

We're finally here at our final topic, the one that we teased right at the beginning. Bill Ackman is a billionaire investor, a manager of the hedge phone Pershing Square. Over the weekend, Ackman was posting on social media saying, some of the highest-quality businesses in the world are trading at extremely cheap prices. Ignore the mainstream media, he said. He then went on to mention Fannie Mae and Freddie Mac as potential 10X opportunities. Matt, you're our real estate guy here. What is Bill Ackman talking about?

Matt Frankel: Ackman, he's very prolific on social media and has a history of kind of calling things out when he thinks that something's going to be a net positive that isn't. Big example is remember the Omicron wave of COVID that initially tanked the market. He came on and said, This is going to be a net positive for a less contagious version that is highly infected would be a net positive. He was right. The Omicron wave actually turned out to be a net positive for ending the pandemic. People tend to take them seriously.

But on the Fannie and Freddie issue, it's not really a real estate play, and I'm going to refrain from turning this into a financial crisis history lesson. Fannie and Freddie, the two government-sponsored enterprises, are GSEs for short. They essentially keep the mortgage market functioning smoothly. They don't actually make loans, but when you apply for a mortgage, it has to meet Fannie or Freddie's standards. They'll back the mortgage. It'll help the lender give you a better interest rate and just provide fluidity to the mortgage market. After getting in trouble during the mortgage meltdown of 2008, when there were a ton of bad mortgages on the books, we could spend an entire episode on that. Both of these were placed into government conservatorship. U.S. Treasury then owned the majority of both. I think that was 80% technically they owned, but they swept 100% of the profits of both agencies once they became profitable again in 2012, less a little capital buffer to let them operate.

Now, President Trump, even in his first term, has been discussing reprivatizing both agencies, removing the conservatorship, and letting them start to distribute profits to shareholders again. These are pretty big, profitable stocks. At one point, Warren Buffett owed Freddie Mac, I believe. He issued a memo in 2019 to develop a housing reform plan that included an end to the conservatorship. The Treasury then started allowing the two to start retaining significant profits. I'd want to say it was about a $20 billion profit cap above and beyond what was really needed to maintain enough capital to run. In 2021, under President Biden, the profit sweep was ended altogether so they could really start accumulating money. But both still remain under government conservatorship.

The biggest arguments in favor of keeping it there is that removing that could potentially destabilize the mortgage market at a time when interest rates are already high, and they've been accumulating capital, but the U.S. mortgage market is huge. They need a big capital buffer, and there's an argument that they don't have the ideal capital levels yet. But as recently as last summer, the president met with bank CEOs to discuss an IPO of the two, which would raise up to $30 billion. Not quite an Elon Musk IPO, but a pretty big one. Ackman started accumulating shares relatively early in the conservatorship period around 2012. Which is actually when I started writing about Fannie and Freddie for The Motley Fool. He's already sitting on some pretty decent gains, and maybe not for a 13-year investment. His cost basis was about 2:29 a share for Fannie, for example, currently it currently trades for about $6 a share. But he's estimated before that it could be worth at least $34 or potentially much more if the conservatorship ended. It's a long-term bet that this would eventually happen. Now, so that's where he's talking about Fannie and Freddie. If you think the government conservatorship could finally end, could be a good thing to look at. But that's not necessarily what he was referring to when he mentioned high-quality businesses at a discount. That was a much broader statement. I agree.

My watch list, I don't know about you two. My watch list has been growing by the day. One in particular, and since we're talking about Ackman, I'll mention one that I have owned for a long time, since probably around 2012, is Howard Hughes Holdings. Ticker symbol is H-H-H. Ackman is the executive chair of the company. It's an interesting real estate business. They've developed large-scale cities. Summerlin in Las Vegas, the Woodlands, and Houston are their two examples. It's been beaten down lately. Ackman himself bought shares last year at $100, and it now trades in the low $60s. Nothing really has gone wrong, except it's doing exactly what they thought it was going to do. Rachel, I'm curious beyond Bill Ackman, what's a stock or two that you might think has become irrationally cheap?

Rachel Warren: There's a few. I have to talk about a company from the retail space, which I cover a lot, and that's Lululemon. They're trading at about 11 times trailing earnings now. The stock's been under pressure for a while. There's been, obviously, concerns about its maturation of its growth in North America. There's been a few execution misses on product launches, but the underlying engine, I would argue, is still a very high-quality business. You're looking at a brand with industry-leading margins, massive untapped runway in international markets like China, which rapidly expanding. That's a company I look at, I think of a dominant consumer brand, high customer loyalty. It's trading and evaluation that's often reserved for those average, slow-growth retailers.

One more I'll mention, or maybe a couple more, is Microsoft and Alphabet, right, in the tech space. Microsoft is sort of in this rare position. I personally view it as actually cheap relative to its earnings potential in the AI era. Both Alphabet and Microsoft are trading in the low 20s times trailing earnings. You're looking at incredible growth rates for both these businesses. In Microsoft's case, they've really positioned themselves as the essential operating system for AI. Of course, Alphabet with their growing TPU business and their integration of AI across the flagship advertising machine. I think these are really high-quality businesses that are undervalued relative to their growth ability right now. There's many of those.

Jon Quast: There we have Howard Hughes, Lululemon, Microsoft, Alphabet. Definitely many companies out there to look at that might be good values right now and might prove Bill Ackman's point that there are a lot of high-quality businesses on sale. You can count on us to be on the lookout, but that is all the time that we have for today. Matt and Rachel, thank you for sharing your thoughts, and to the listeners out there, thank you so much for joining us today. As always, people on the program may have interest in the stocks they talk about, and The Motley Fool may have formal recommendations for or against, so don't buy or sell stocks based solely on what you hear. All personal finance content follows Motley Fool editorial standards and is not approved by advertisers. Advertisements are sponsored content and provided for informational purposes only. To see our full advertising disclosure, please check out our show notes. Thanks to our producer, Dan Boyd, and the rest of The Motley Fool team. For Rachel, Matt, and myself, thanks for listening, and we'll see you next time.

Jon Quast has no position in any of the stocks mentioned. Matt Frankel, CFP has positions in Howard Hughes and SoFi Technologies. Rachel Warren has positions in Alphabet. The Motley Fool has positions in and recommends Alphabet, Howard Hughes, Lululemon Athletica Inc., Microsoft, Tesla, and Uber Technologies. The Motley Fool recommends Instacart. The Motley Fool has a disclosure policy.