The #1 Portfolio Mistake Keeping You Broke (And How to Fix It)
Earn Your Leisure
September 6, 2026
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Speakers Troy Millings, Rashad Bilal
TopicsInvestingBusinessEntrepreneurship
Troy Millings (0:00)
Two different reasons. If I'm looking for upside, I'm taking Anthropic. If I'm looking for pure upside, I'm taking Anthropic because of the role that is gonna play in pretty much every industry, which is why the government has to figure out how they're going to either work with it or figure out a way that it can incorporate it. I think Anthropic is that important. And Dario has become, he's won people over. He's certainly won people over.
He's become more of a face, he's speaking more. I saw him with the announcement with Mark Benioff at Salesforce. And the partnership that they just announced when Sasspocalypse was the theme. He kind of literally changed the entire software industry with that announcement.
Apple, if I'm looking for certainty and like something that's steady and it's a trusted brand, and it's a long-term investment, I would choose that. But if I'm looking for upside specifically, I'm going with Anthropic.
Rashad Bilal (0:55)
Shawty, what about you?
SPEAKER_3 (0:58)
Apple.
Rashad Bilal (1:00)
Okay.
Troy Millings (1:01)
Tell us what I'm.
SPEAKER_3 (1:03)
Well, it's lightning round, so I don't want to be too long-winded, but it's a brand that you could believe in. And defense is the best offense. So yeah, definitely Anthropic has more upside potential, but it also has more downside risks.
Troy Millings (1:17)
Who you got?
Rashad Bilal (1:20)
What are we looking for? Safety or return?
Troy Millings (1:25)
Return. I think that's what most people are looking for.
SPEAKER_3 (1:33)
It gotta be a combination of the two.
Rashad Bilal (1:35)
Yeah, I would say to me, parent Anthropic and Apple together in a portfolio, it was like in the dream world, if I can put Tyrese Maxey and Kevin Durant together, like one's more seasoned, one's more up-and-coming, superstar. So for clip purposes, I'm going to say both, but if I'm looking for pure return, I'm going to come back to you guys. Tune in to the next Stock Club call if I tell you, if I like Anthropic or Apple more. Back to you guys.
Troy Millings (2:07)
Yeah, I mean, it's just a crazy time, right? You think about Apple getting to a trillion dollars and we remember that, and now you have a company five years later that's going to probably IPO at 2 trillion.
Rashad Bilal (2:18)
Yeah. Yeah.
Troy Millings (2:19)
Pretty amazing.
Rashad Bilal (2:21)
Our last one, Salesforce versus Ethereum. Which one would you lean on?
If you had your last 30,000 to put into the market, you had to pick one. I'll go first. I am elated.
Troy Millings (2:34)
That's not even a fair comparison.
Rashad Bilal (2:37)
I wanted some diversity because we always do Apple, Microsoft. The ones I've heard the comments, you only talk about Apple, Microsoft and Routard. Okay. Well, nevertheless. And then, but if you're down a hundred bucks on the stock, then you're like, hey, what do I do? I do like Benioff's adjustments. I like him as a CEO. I do not love the company to invest in long-term. I do think the SaaS apocalypse narrative was overrated because AI is software and Bitcoin and Ethereum is software. So I find how they parsed the differences very interesting.
If I had to pick one though, that I would probably lean on. Well, Troy, let me come to you. Which one would you pick?
Troy Millings (3:21)
It's nasty, man. I was big on Ethereum. I still have like, you know, some money in Ethereum.
And I understand that blockchain, the functionality of it, I understand everything's being built on the Ethereum platform.
Rashad Bilal (3:40)
Where Vitalik at? I haven't seen or heard from the man. Where the fuck is Vitalik at?
Troy Millings (3:46)
What's the time frame? How about that? What's the time frame? Five years?
Rashad Bilal (3:49)
Five to seven years. I'm seeing, at least when the fire is going on with MicroStrategy, I'll give them credit.
Sailor doesn't back down. I don't know where in Russia Vitalik is. And for that reason, I'm picking Salesforce.
Troy Millings (4:05)
I'm leaning towards that too, which is ironic. I was just going to say, I'm leaning towards that because we know Benioff. And I think the only thing that troubles me with Salesforce is the debt structure around how they're going to incorporate AI into the CRMs. But the partnership with Anthopic makes a lot of sense. And so he's been proven to keep that thing afloat.
So yeah, I'll go with Salesforce for this.
Rashad Bilal (4:33)
Shawty.
SPEAKER_3 (4:34)
I'm a Bitcoin maxi. And I only believe in Bitcoin.
But.
Rashad Bilal (4:42)
No Litecoin?
Shouts to those of you who were trading and investing back in the day on Litecoin was supposed to be the one that was, you know what I mean? Yeah.
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