Founder's Story - Inside the Mind of Wall Street’s Father-Son Duo: What Most Investors Get Wrong | Ep. 239 with Ken and Connor Mahoney Founders of MahoneyGPS

Episode Date: July 4, 2025

Ken and Connor Mahoney, the father-son team behind MahoneyGPS, to unpack three decades of experience navigating Wall Street. They talk market cycles, the AI boom, crypto hype, IPOs, and why compound interest might still be the greatest secret weapon in investing. Key Discussion Points: How Ken built a 36-year Wall Street career and stayed relevant through market upheavals Why AI is still in the early innings—and where institutional money is flowing now The psychology of crypto and why Gen Z sees it as more than an asset class Father vs. son: generational differences in investing mindset and portfolio strategy Why dividend stocks may no longer be the answer for retirees The future of the dollar, global currencies, and where to stretch your money Their daily newsletter and media presence across CNBC, Bloomberg, and Fox Takeaways: Great companies don’t just survive—they reinvest, grow, and reward shareholders Compound interest is still the most powerful (and underused) investment tool Technology is the new infrastructure—and the market rewards those who keep up Crypto remains a high-risk, high-reward trading vehicle—not yet a true currency The U.S. dollar still reigns, despite temporary global shifts Closing Thoughts:Ken and Connor Mahoney are living proof that timeless market wisdom and forward-thinking strategy can coexist. Whether it’s riding the AI wave or challenging traditional retirement investing, they’re rewriting the rules while staying grounded in discipline and data. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hey everyone, welcome back. So I'm fired up right now because the markets, Wall Street. I mean, there's so much action. I was there last week in New York at the New York Stock Exchange. Always, what a great experience to just be in it. So that's why I'm excited for Ken and Connor Mahoney. And I know you all, I mean, 36 years combined experience or over 36 years on Wall Street. You do a lot. lot of things you help advise and you have a lot of amazing clients that you work with as well. And I can't wait to learn more about the Pulse. We were just talking about, you know, recent IPOs and everything. But I'd love to hear, you know, right now, if somebody asks you, what are you looking at most when it comes to the markets?

What would you tell them? Well, I would say, first of them, I'm glad you enjoyed your trip to New York Stock Exchange, right? Corner Abroad and Wall Street, where capitalism thrives. And it's amazing companies come public there and then shareholders trade these things back and forth. Just again, I'm sure you felt the energy that's awesome. Hey, this AI, we're probably a second

or third inning. You know, there's a lot of negativity about headlines, tariffs and all, but at the end of day, there's so much money being spent. I think Amazon's going to spend $103 billion for AI and data centers. Microsoft $93 billion. The race is on to build faster and better.

And look, we want to follow the flow. And one other thing, I'm sure Conner has some comments here or two, if you think about 2020 and COVID and how much money went to diagnostic and medical devices, right, and all this stuff, well, just fast forward five years from now, instead of being health care, thank God, COVID's out of rare. Now the huge amount of spend is in technology to keep up with one another. I think what's really interesting is I'm looking a lot of different institutional positioning or, you know, people are actually starting to short up here, which I think it's as more fuel

to the fire, which is good. And basically looking at longer term positioning and options, it looks like, you know, new highs are inbound. It seems like the path of least resistance to touch 60100 or so. And then we'll have some type of triple top and see if we get through there. But the way positioning is looking right now, looks like we could just squeeze into the last few weeks of June and the quarter is my take. So how do you see the IPO? We were just talking about the circle IPO that just happened. And what do you, you know, it seemed like a lot of excitement, pulse is good around, you know,

how people feel. Are there more potential IPOs coming? What, what can we expect there? Yeah, I do think having CorWeave was a crazy IPO. I know it took a little while to get going, but as low as 40, up to like 160 in the matter of maybe a few weeks or a month. Then you had E-T-O-R. That one's done all right. And in a circle went pretty crazy. I think it was indicated at $30 a share. and then went so much bidding for it went actually live at 60 and all the way up to like 130 something so we're definitely one of those maybe a little frothier periods i do notice that we're getting a lot of small caps starting to move so maybe late cycle bull market i still think longer term ball market but a shorter term like you know we're near a a little blowoff top we need

some rest i guess um it's been kind of crazy so when you're looking at the markets is there something that you're looking at to, in order for you to really evaluate, is something worth it or not? Yeah, it all comes back to earnings, my friend. It's always going back to earnings. So, you know, first of all, there's a process of elimination, too, Daniel, where we're not going near pharmaceutical companies. They have a big target on their back for the administration. We're not going to find it's in autos and airlines and somebody's Godforsaken retailers. You know, they say it's a stock market, but it's really market of stock. So we, the reason why we're in this AI lane is there's so much money being spent. And And those companies' earnings, when they have stronger earnings, good things happen, right?

They build up their balance sheet. They do buybacks. They raise their dividend. They buy the competition. They buy personnel and so forth. So so many good things happen in that cycle when companies have really strong earnings. And, again, we have such a strong tailwind because so many companies want to, you know, get their chips up and running, get their data centers up and running. And those companies are the picks and shovels of this, this huge AI boom.

Well, they're the winners because they've got great earnings and they're going to pay shareholders very well between stock dividends and buyback. I was just listening to somebody talking about the future of like robotics and humanoids and, you know, as AI and AI and robots kind of merge, like physical robotics could be self-driving cars, could be literally a robot that's with us. I think we've seen, you know, some companies talk about that. How do you, how do you see this in terms of not just AI being in the computers that were used? using but now moving it to physical things i think it's actually i mean i think we could all agree it's a little scary maybe but um i do think you know there is going to be adoption of these technologies there already is i can't tell you one person that doesn't use like chat gbt or rock or some other service like that basically daily um and we were all a little skeptic of it at first but you

do see the actual applications of it so um i just think there is some adoption and you know we don't one of these like Terminator, I've seen those Tesla robots. They're a little scary, but you never know. These could be very useful and practical in different ways as long as people are adopting to them and they're obviously under control or, you know, their safety guidelines along the way. But, yeah, that certainly is the future. And, you know, we know companies are spending like crazy to boost, you know, for data centers

and AI infrastructure, takes a lot of computing power. And like Ken said, do think it's early innings still for all these. different AI applications, most likely. When you look at people that trade of different age groups or different ages, do you find that they're looking? So, you know, I know, Connor, you're in your 20s. Can you look like you're in your 40s? Yeah.

So when you're looking at these different age groups, are they looking at things differently or are they asking you different questions? Yeah, I think because of social media and so many resources, a lot of really good questions. I know for the older folks, so to speak, which I am one of them, by the way, Danielle, I don't know. They say, okay, now I retire. I'm going to go to dividend paying stocks. We don't like that. I mean, a lot of dividend paying stocks, you get your five or six percent, and many times these stocks that they cut to dividend, the stock could get cut in half. So the risk reward to us doesn't really look so great for a lot of people who are in their 60s or so

they're looking for dividends. In fact, we've rather just, you know, their playbook, go with those pitching shovels, the Apple, the Microsofts, then the video. Have those names grow in your portfolio, keep up with cost inflation, and skim off a little bit to create some income. But again, it's a wholesale change, 180 degree change we see as opposed to buying dividend checks, you know, dividend stocks when you retire. Instead, we still like to say growth, growth, growth, even through retirement, especially if you're going to live into your 90s, right?

Right, guys? At 300, we're going to live in to our 90s. We definitely want that inflation hedge in stocks and real estate are really the two best areas to protect against inflation. How about you, Connor? Anything from, you know, when you're... What do people in their 20s think about the market? I hope they're getting involved as soon as possible.

I think the big thing to have is through work is passively investing in 401K. It's like, you know, it comes out of your paycheck. You don't really have to think too much. Hopefully you just check the large cap growth or growth allocation, all stocks. We talk to people about that all the time. Even into your 30s or 40s, that's not money you're going to use until you're probably at least 60 or 65 or older. I just hope that people are investing to some degree in stocks primarily. And yeah, for more aggressive people, maybe they have a different account.

You know, they can trade and stuff and look at Bitcoin or some of those more aggressive assets. But I just think a good play. You just have to start. You just have to have something. Let that compounding start young, you know, and that's a huge, huge part of the puzzle, I think. Yeah, Albert Einstein is a pretty smart guy. You said the eighth one of the world in Everis, listen, is kind of. compound interest. And it shows, you know, stacking returns on top of returns. And, you know, sometimes I'll get somebody retired at 60. They're like, I have a million dollars in a account. I can't believe it. But again, it was years of putting away pre-taxed dollar cost averaging towards growth. But again, I love that Albert Einstein who was, you know, a scientist, physicist, not really an investment person. But he did say the eighth one of the world is compound interest. How are you feeling about crypto? And, you know, I have Bitcoin ETF personally. So, you know, I'm always looking at.

are there more ETS coming? I was just saying, I believe the Vatican might be buying like a billion. I don't know if that's even true. Somebody, something I was reading, but new poll, maybe he's a trader there too. Maybe, but I know there's like a lot of people, a lot of traditional investment companies, a lot of companies are buying in Bitcoin, obviously, you know,

reaching those all-time highs again. I think it's definitely, it's a good trading vehicle for sure. I think I, BIT, there's BITX, is leverage. There's so many GVTC. There's so many different companies basically getting involved at this point. I think, you know, it's come to the realization that, you know, not even really knows what Bitcoin is or does. We just know it's an asset class that is moving in price. So it's a good trading vehicle, I think, for people. It's hard to say the actual, you know, par value, right? People say, oh, we can trade Bitcoin. It just was 1001.

thousand two days ago and now it's 110. So it's an extremely volatile vehicle. I do think it's pretty speculative asset, but then again, like I said, it's a good trading vehicle and more and more institutions seems to be getting involved, which legitimizes it further. I think there's some higher targets probably this year, 120, 125, something like that, you know, if you look at fibs and IBIT option flows and different things that are out there, it seems like, again, I think I talk about paths of least resistances, Bitcoin is probably higher in the next few months, six months. I've heard some people say could hit a million dollars at some point. Yeah.

I do think for some people, they see it's like their path to, it's like a self-fulfilling prophecy and trading at times. We all have this target in mind. We're going to all buy it up to these targets. And Bitcoin, like I said, is no earnings. There's no real fundamentals. it's kind of like a psychology training vehicle. So trading vehicle, yeah. And that's what the problem I have with it.

One wants to put like 5% in a portfolio of flying, but it's like business models, like Microsoft, right? They're into their own LinkedIn. They have all the gaming under Xbox and Windows this and Windows this and Windows that. I mean, if that's a real business, then, you know, the problem here's, here's the problem I have with it. Tell me one day I could take my wallet.

I'm not talking, I want my coin wallet, walk into Best Buy or walk into Barnes & Noble and use it, then I'm like, okay, we have something. So I'm still kind of a show me state. I'm older that I'm Generation X. That's why you Gen Z folks have a different take on this. I like businesses with cash flow that are more predictable. I know this can go up in value. So some clients, I guess you can recommend a few percent of anyone's holdings, I guess,

diversifying to it. But at the end of the day, I can't use the currency. And I'm told the reason why we buy it is that someone else buys at a higher price than you. I'm told the reason why to buy it is that you could transfer your money around. Well, I could do that with Zelle. I could do a PayPal. I could do that a whole bunch of other services. So until I get to me, anyway, until I get to use it to buy something,

what I actually call it like a legit currency or legit. Right. Seems like, you know, people see it as inflation hedge, maybe the digital inflation hedge alongside like gold as being a physical one or real estate or stocks in general. So it's, it's an interesting phenomenon. It's, it's pretty incredible. It's steward. Yeah, I like how you put that, Connor. You know, when I put it when I put money into crypto, I do just hope that it goes up. It is a self-fulfilling prophecy. Then maybe something that has a huge amount of uses yet. When it comes to the dollar, though, I'm curious about, I see, I think the dollar to the euro, the dollar was down. We were just traveling somewhere and I noticed my money didn't. go as far as it did last year sadly but what is there something that we can expect or hope to see and maybe this year when it comes to the dollar and then on top of that there's a lot of people

talking and there's a lot of rumbles about things replacing the dollar and such at you know how do you feel about that as well okay so i'll jump on that so as far as the dollar we still think it's going to be the world currency you know there was some nicks in april we had the liberation day which turned into a real mess and then, you know, and dollar went down and gold went higher and cryptos went higher and, you know, but now you start seeing the homostasis again, you start seeing a balance. And again, at the end of the day, I still see the U.S. dollar being the world currency. Now, it doesn't mean it won't have its bumps and bruises, but if you look at Europe, seriously, I don't get it. I mean, they over-regulate. There's hardly any innovation

there. I just don't get it. I don't know how the euro would be that. Japanese, they have their own issues and you know maybe we're the prettiest and the ugliest contest so to speak but it's good enough because again america uh with all the ingenuity that takes place yes we're trying to get better trade yes there's a lot of uncertainty but i still think the go to currency will continue to be the don't you know further in because i have a lot of questions um i know you have an incredible newsletter that i read every day the good thing about your newsletter is it's it's funny it's informative it's It's fun to read.

It's easy to read, which is something, you know, I enjoy, I can only read something I enjoy because I'm, you know, if not, I'm like the, you know, ADHD. But if people want to get in touch with you, though, they want to read your newsletter and everything, how can they do so? Yeah, so it's Mahoney, GPS.com, M-A-H-O-N-E-Y-GPS.com. Right there is our newsletter, sign up for it. We have a lot of ideas, as you can tell, and bounce off a lot of ideas. We just love it.

We literally breathe this stuff. And certainly it's an amazing, America's amazing, be able to have this opportunity to invest in the best companies, not in the US, but in the world. There's only one Apple, only one Navidia, one Microsoft. I could go on and on and on, truly innovative. And that's the spirit of America in the best companies in the world. And we have access to it 24-7, click, click, click.

You can buy stocks all day long. It is such an amazing opportunity that we have. Well, this has been great. Ken and Connor, father and son duo, not too many in the finance space that we've gotten to talk to at least. So it's always great to understand, you know, the different dynamics and age groups, everything that you're seeing, that you're working on. I know you're talking in like tons of media all the time,

but I just want to say thank you so much for joining us today. I thank for having us, Daniel. You're great questions and make this kind of think through it and help your viewers enjoy some of the commentary that we have.