In this segment of MarketFoolery, host Mac Greer is joined by David Kretzmann and Aaron Bush of Motley Fool Rule Breakers and Supernova to discuss Square (NYSE:SQ), shares of which jumped sharply after it announced a new bitcoin-buying option in its money-transfer service. What does this all really mean for the company -- and the cryptocurrency? What are the investment theses for each? And where do they stand on other cryptocurrency's initial coin offerings?

A full transcript follows the video.

This video was recorded on Nov. 15, 2017.

Mac Greer: Guys, let's talk Square. Shares of Square up big on Wednesday after the digital payment company said that it's adding a bitcoin-buying option to its money transfer service. Aaron, I confess to not really understanding bitcoin. I don't think I'm alone. But I am a Square shareholder, and this seems like a stamp of approval for bitcoin. So, what does this deal mean for Square, and what does it mean for bitcoin?

Aaron Bush: I think Square has had the option for the POS system where merchants can accept bitcoin. This is different from that. This is more specific with their Square Cash app, which is a competitor to Venmo, where I can send David money, David can send me money. Now, they're making the option, maybe we can send each other bitcoin, or maybe it might just be easier for me to buy or sell bitcoin on that particular app, just because it might be more difficult to buy it and store it elsewhere. So, that's really what they're doing here. And it's definitely a stamp of approval for bitcoin. I think Jack Dorsey, the CEO kind of has been pro-cryptocurrency, pro-blockchain for a really long time. So, he sees the benefit of what this does for technology. I think this has been in the back of his mind for a while, but this is really maybe the first or second steps Square has taken to make it available or applicable to the average consumer or the average user. I don't know how much this really moves the needle, but it's just a way for them to stand out and do something different from someone like Venmo. And I think this might not be as widely known, but the Square Cash app has actually bypassed Venmo recently in terms of downloads in both Apple and Android. I think this is just a way to make sure they can secure that lead and take even more market share.

Greer: Is it fair to say -- because I know you're a Square shareholder -- given the two, if I just to spot you up with these two options, you could invest in bitcoin or you could invest in Square, are you more bullish on Square?

Bush: [laughs] That's really tough. I think, if you invest in bitcoin, you have to be willing to lose all your money.

Greer: OK. I'm not, by the way, but thank you.

Bush: But the upside for bitcoin is potentially significantly larger if it does take hold. Square, you're not going to lose all your money, probably.

David Kretzmann: Hopefully not.

Bush: Very, very unlikely. But, I do think it has tremendous upside, but it won't be as extreme as something like bitcoin. Personally, I would be more willing to invest in something like bitcoin, which might make some people be like, "What? That doesn't make sense." But, I think, what bitcoin is doing is so groundbreaking that, even though the odds of failure are significantly higher, the chance that you're getting in closer to the ground floor of a humongous movement, I think that's enticing and worth a small position.

Greer: David?

Kretzmann: I still I have a hard time wrapping my mind around this. Hearing Aaron, as he's learned more about it, definitely helps. He helps make it more digestible and understandable and relatable. But, with bitcoin, the thing I have a hard time wrapping my mind around is, I feel like a lot of people describe it as a store of value. It's almost like becoming a digital version of gold. Especially right now, where it seems like a lot of people who are buying it, at least all these financial bloggers who are jumping on the bitcoin train and crypto train, they're buying it with the anticipation that it will become more valuable. They're treating it as an investment. So, thinking, five years down the road, maybe I'll be able to sell my one bitcoin for $100,000 a bitcoin up from whatever it is today, like $7,200. If that's the case, if that's how you're treating it, it would make no sense to use it as a currency, because why would you give away something to buy an apple when you expect that currency, that bitcoin, to become 10X more valuable in a few years? That's why I don't think this particular announcement will necessarily drive a whole lot for bitcoin. But, I can't pretend to know a whole lot about it. And then, there's all these things, like forking and all these subsets of bitcoin, so maybe this plays into that. But, I don't know. For me, I still toss this into the "too hard" category as investments. I think, if you do invest in bitcoin or another cryptocurrency, you keep it as a small portion of your net worth that you're willing to lose everything, like Aaron mentioned.

Greer: What worries me, and I'm with you on the "too hard to understand" category, but I was walking the dog recently, and a neighbor came up to me and presented me with this "opportunity" to invest in this new initial coin offering that he was part of.

Kretzmann: [laughs] Oh, God.

Greer: Yeah. Based in Europe. And then he starts talking to me about blockchain technology and all that. And I'm walking the dogs. So, first of all, don't ever approach someone with a business deal when they're walking their dogs, that's just wrong. That's a sacred space. Our dogs have various issues that I will not go into, but you have to focus on the dogs when you're walking them, that's all I'll say. You have to focus on the dogs. And he's hitting me with this ICO stuff. And I know it's probably not fair to bitcoin, but when people start presenting you with these can't-miss investing opportunities, it makes me a little worried in terms of the hype cycle.

Kretzmann: It seems reminiscent of the heyday of the .com era, where everyone was talking about the new .com or tech stock. My feeling with this is, I think there's a lot of potential with the underlying technology. Just about everyone will say, it's not necessarily that one or two coins will win out. But, the underlying blockchain technology, there's something there, and that tends to be the line of reasoning I subscribe to also at this point. But, with the ICOs, I haven't seen a lot of sustainable value driven from that. I don't know, when you buy an ICO, what would you actually get, because you're not getting a stake in that company. It's often companies that haven't even launched a product yet. So, I think that's probably even riskier than buying bitcoin itself. But, again, a lot of this is still over my head, so I can't pretend to be an expert.

Aaron Bush owns shares of AAPL and Square. David Kretzmann has no position in any of the stocks mentioned. Mac Greer owns shares of AAPL. The Motley Fool owns shares of and recommends AAPL. The Motley Fool owns shares of Square and has the following options: long January 2020 $150 calls on AAPL and short January 2020 $155 calls on AAPL. The Motley Fool has a disclosure policy.