The Conundrum of Investing in AI Today

Motley Fool Hidden Gems Investing

The Motley Fool

Business, Investing

4.3 • 3.1K Ratings

🗓️ 29 May 2026

⏱️ 39 minutes

🔗️ Recording | iTunes | RSS

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Summary

Money continues to pour into AI companies like Anthropic, who announced a $65 billion fundraising round this week. But companies are starting to scrutinize their AI investments, which may not be paying off as hoped. Plus, we discuss some of our lessons of a lifetime investing and the stocks on our radar. Travis Hoium, Lou Whiteman, and Emily Flippen discuss: - Anthropic’s $65 billion raise - Corporate America’s ROI on AI - What do consumers want? - Our favorite investing quotes and books - Stocks on our radar Companies discussed: FedEx (FDX), FedEx Freight (FDXF), Astronics (ATRO), Transmedics (TMDX), Alphabet (GOOG, GOOGL), Amazon (AMZN). Host: Travis Hoium Guests: Lou Whiteman, Emily Flippen Engineer: Dan Boyd Disclosure: Advertisements are sponsored content and provided for informational purposes only. The Motley Fool and its affiliates (collectively, “TMF”) do not endorse, recommend, or verify the accuracy or completeness of the statements made within advertisements. TMF is not involved in the offer, sale, or solicitation of any securities advertised herein and makes no representations regarding the suitability, or risks associated with any investment opportunity presented. Investors should conduct their own due diligence and consult with legal, tax, and financial advisors before making any investment decisions. TMF assumes no responsibility for any losses or damages arising from this advertisement.We’re committed to transparency: All personal opinions in advertisements from Fools are their own. The product advertised in this episode was loaned to TMF and was returned after a test period or the product advertised in this episode was purchased by TMF. Advertiser has paid for the sponsorship of this episode.Learn more about your ad choices. Visit ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠megaphone.fm/adchoices Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	Is AI rationality here? Motley Fool Hidden Gems Investing starts now.
0:10.0	Welcome to Motley Fool Hidden Gems Investing. I'm Travis William.
0:12.4	Joined today by Lou Whiteman and Emily Flippin. Guys, we can't start the show without
0:19.2	talking about some of the biggest deals that we have ever seen in private markets.
0:22.9	We're going to get to the rationality that may be here in artificial intelligence, but I want to start with Anthropic.
0:29.3	They announced this week that they're raising, or they completed raising, $65 billion, Emily, at a nearly $1 trillion valuation. It seems like Anthropic can do absolutely no
0:40.7	wrong at this point. Yeah, and Anthropics case, it kind of feels like the only thing that's
0:44.9	stopping itself is maybe itself, because as you mentioned, that trillion dollar valuation,
0:49.9	near trillion dollar valuation begs the question of how much profits are you projecting out
0:55.6	over the next decade, over the next two decades, over the next 100 years to justify that.
1:01.5	And ultimately right now, all of this funding's private market funding that's flowing into
1:06.4	Anthropic is justifying that valuation. But if and when that funding dries up,
1:10.7	suddenly Anthropic is going to be experiencing the pressure on itself to make its business profits. is justifying that valuation. But if and when that funding dries up, suddenly
1:10.9	Anthropic is going to be experiencing the pressure on itself to make its business profitable,
1:15.3	right? And I think that involves no longer subsidizing usage, right? Forcing enterprises to
1:19.8	potentially pay more. And when you start adding in the complications of that equation for
1:25.2	companies, it does start to beg the question of what you just mentioned,
1:28.2	which is what does rational AI look like at an enterprise scale? But for now, that's not really
1:33.1	anthropics problem because everyone's just giving the money, hand over fist. Yeah, we'll get to that
1:37.8	rationality in just a second. But Lou, I just want to stick on this for a moment because
1:42.7	the numbers have gotten so crazy. We talked
1:45.0	earlier this week about the SpaceX IPO. They're looking at potentially up to two trillion dollars
	...

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