Trading Secrets - 307. Thirty Minute Thursday: Europe, Eras & Olivia Levin with Jason & Kathryn

Episode Date: June 11, 2026

This week on Trading Secrets: Thirty Minute Thursday, Jason and Kathryn are coming to you live from their European vacation! The duo shares updates on their travel adventures, what’s on the itinerary next, and some of the funniest moments from life on the road abroad.They also break down key takeaways from this week's conversation with Olivia Levin, including the lessons, insights, and moments that stood out most. Plus, Jason and Kathryn dive into all things Taylor Swift—from the latest headlines and fan-favorite moments to the cultural and business impact of one of the world's biggest stars.

We are back with another 30 minute Thursday. Now, we're recording this well before Thursday. That's because Catherine and I are in Europe. But we are doing this together. It seemed appropriate, given this is the first time ever that Catherine co-hosted with me, which was amazing. Swifties for eternity, Olivia Levin, an absolute beauty. So no David on the 30-minute Thursday here,

but from Europe, I have the one and only, Catherine Hurley. How are we doing today? So good. Waking up in Italy has been magical. Magical. I'll tell you what. It has been an amazing, amazing vacation from Santorini to Lake Como, two of the most beautiful places I've ever seen in my life. By a long shot. You can't even imagine it until you see it. And then you still don't even feel like you're actually looking at it in real life. I feel annoyed with myself looking at my, or listening to myself online. But I'm like, it just seems like AI. Like it literally looks like you put goggles on. And you.

you go to a dream place. And that's what it is. Yeah, that's the only way to really describe it. Like, it just doesn't feel like this could actually exist in real life. Yeah. It's not, it is just, it's nuts. And the food yesterday, we had our, I had my first plate of spaghetti and red wine in Italy. And when I took a bite, what happened? You literally had tears pooling in your eyes. It was the best, like, highest moment I have had. I mean, that bite of the spaghetti. with the sauce, the sauce. Oh, my God. I'm going to go back there tonight. I order three plates in the red wine. It was like magical. It's like what I honestly have dreamed of. Yeah. I said the only two times I've seen you emotional is like being in love with me and then eating spaghetti. That or yeah,

the bill's losing. That's very true. Well, what a privilege it is that those are the things that are driving emotion in my life. All right, Swift's fraternity. You were in the episode with me. what'd you think of it just being there? I didn't know too much about her. And I think my biggest takeaway is how impressed I was with her, like, as an individual. I think it's really easy to assume what professionally being a fan would look like. And she was just A to Z, very impressive, super articulate, fun, light, easy to talk to, and an incredible businesswoman.

You are very passionate, Swifty. I mean, what is your take? you're the one that got me into Taylor's with. What's your take on the whole idea of like turning that passion into a business and some of the tips and tricks she gave? Well, I'm mostly just jealous because I think that that's just like we're in this new age of people being able to take something they're really passionate to. And then with the invention of social media, being able to then pair that to like scale it. Like a hundred years ago, you could have been the biggest Beatles fan ever. But like, how are you going to do anything with that? So I think it was a really creative take on it. But it was also so natural. I feel like she kept talking about how like this thing happened and then this opportunity happened and then she just kind of like went with it. She didn't force it. And I think that's how easy it was to realize like it organically is that much of a passion for her. Like she really is that much of a fan. You couldn't afford. Like someone can't be like, ooh, I see what I could do here and like let me fake this. She's a real one. She's a real one. She is a real one. All right. There's a lot of, I mean, what else did you think though from the interview? Were there any questions, concerns, thoughts, takeaways? Where are your biggest takeaways?

The secret sessions, being able to get more insight into that was really cool for me just because I've like known that that existed for the last 20 years, but I've obviously never been in the same room with somebody who's like intimately been around Taylor Swift. I liked that she talked to them about each song and didn't just like roll through the record and like move on. Like that's so Taylor to be like, now let me tell you about this one and why I wrote it. And then her book, you know, I've read a couple chapters of it now. And I think I didn't know that she had had written that up until like the day we did the podcast. And I think showing how much it's bigger than just being a fan of Taylor Swift. And it's such a connection point for two total strangers. I said this to you. Like if I met somebody at a bar and I was like, I love Taylor Swift. And they were like, me too. I'd be like, I don't need to know anything more than that I would be your friend now. Like that's how fundamentally connected. I think people who identify with her music as much as some. someone like Swifties for eternity. What's your take on the, I think it's like, yeah, I think it's perfectly sad, especially now.

Yeah, you think about the people that are just major fans of anything. It could be anything from like Pokemon cards to bands to shows. And the fact that you can make legitimate businesses off it is crazy. I mean, yesterday online, I saw this woman who is a big fan of coaching yapping. Yapping is just speaking to camera. She created a YAP challenge and did 1.2 million. in sales of 13 days of these like Yap masterclasses in the world that we live in today. It is so incredibly wild how you can find ways to monetize.

And I think that's a big takeaway from this. Like the things that you love the most, there's businesses behind those things. The whole ticket war thing, before I get into Olivia's connection to the ticket war thing, with everything that happened with Ticketmaster and Taylor Swift, what was your vantage point is a fan looking to buy a ticket from afar? I think what was so interesting is so many people didn't know it was going to go that sideways with how her tickets were. So most people were just waiting in the little portal.

And then it went obviously so haywire so fast. And obviously most people can't say that their fans would turn their ticket sales into a federal investigation with how intense it was. I think a lot of people blamed her, which was unfortunate. And then, but Olivia's involvement obviously helped so many people. And I think that that, from Ticketmaster's standpoint, too, is what their goal was, is that people couldn't monetize what they were doing. But it was like sad. I think so many people who loved her didn't get to see her because people were like seeing it as a financial opportunity.

It's like F1. I think I read the other day that's like one or two percent of F1 viewers will actually be able to see an F1 event given the price point of the tickets. We just saw with the New York Knicks. there were some tickets going for over $100,000. The whole ticket game to me has gotten just crazy. I also saw a video of a Spurs fan in New York leaving MSG getting absolutely this shit kicked out of them. I was thinking of how tragic that is. That person just spent all that money.

And because you're a fan of another team and you're in a city that people are shoulder-to-shoulder acting like assholes in one wrong turn and you're getting this shit kicked out. You go into a game. I don't know. It's like the whole ticket thing is crazy. is you can't compare the tickets of a sporting event to a Taylor Swift concert or any show, honestly. Well, in some capacity, I guess you can. But yeah, the ticket game has changed.

It was interesting to hear about the ticket war. What's your takeaway? Like my understanding, right? So when we talked to Olivia, she is taking the tickets, finding them through a group of community that are willing to give them up at face value and then doing the administrative labor

of making sure that those tickets are then deployed to fans at a fair price point, the price point she received them at, and then charges a fee for them. I think I said this in the podcast, but I was like, that's so Taylor Swift of the fans to be like, I don't need to make any money on this. It's more important to me that this gets into the hands of somebody

who actually wants to go to the concert and who values that. So I think that she was the perfect connection point of making that happen because so many people got scammed. Like I think I may have said this too, but like my friend lost like $2,500. She sent to somebody who scammed her online. So yeah, I love that. I thought it was such a wholesome moment. Yeah, I think so too. I mean, brilliant. Honestly,

you should get paid for what you do, the work you do. You should get paid for trying to find ways to solve problems. That was a huge problem. He spent a lot of time doing it and you should be rewarded for that. Like to me, it just feels like more of a no-brainer. It gives $3. Like the fact that she got any flack on that is insane to me. Okay. So we do have some new Taylor Swift news this week, though. Lots happening. She just had her new single come out. Give me a breakdown from when we recorded this episode to where we're at now. What is going on in the world of Taylor Swift? So there are some Easter eggs for a hot minute, even with what she was wearing. She was wearing very toy story coated outfits, which is something she's done for a lot of her different eras.

So people thought some things were going on. And then there was billboards popping up with TS all over it. But every time toy story has ever come out, it's always like said toy story and like, let alone like two, three, four, five. So the fact that it was like just TS was like strange and different. So yeah, everyone was right. And that's where we were talking about this earlier. But the Easter egg thing, I think a lot of people who aren't fans of Taylor Swift think that we're like crazy and making it up. But Taylor like really has embedded so many Easter eggs that ended up coming to fruition. So then what, like most fans, I think, consume content versus Taylor's Fiff fans investigate her content. Like, if you're a fan of Billy Eilish, you're like, wow, she's on a great last night

where like a Taylor Fiff fan's going to be like, why is she wearing those shoes? What color is her nail polish? But that's because she does that, right? Like, she intentionally leaves these clues as to what's coming next. Some of the clues, right, she was wearing the toy store colors for a while. You notice that her nail polish was orange, great before the, uh, left. if a showgirl was released. So this, I mean, they pay so close attention because she gives them reason to. Yes, but because we pay close attention to everything,

everything isn't an Easter egg. So that's where it's funny is like we also look like a bunch of goons sometimes because like for eight months, every other week people thought reputation on TV was getting dropped. And to this day, it hasn't gotten dropped. So tied to the Toy Story release, a lot of people think since this is her first country song in like 20 plus years,

that this might be the re-release of, Taylor Swift debut, which is her first album, which was her only like true, true country country album. But yeah, it's a great song. It debuted at number one on Apple. I think it's the most stream song of all time from a soundtrack already. And then it's their leading country single of the year. So I wonder, I mean, interesting. Like how far in advance, I'm just thinking like if you're someone who sucks at planning, although I'm doing a good job so far in Europe. Really? You're doing so good. I'm actually incredibly impressed with me. Really now. The guys might be a travel planner 2.0 after this. But how, like, okay, I think about

my outfit tonight. I'm going to, like, we got a nice little setup. Hopefully, Evan, don't screw it up. But we have a good setup here. And so I'm thinking about my outfit. I'm going to plan my outfit in right when we hang up here. She's planning outfits like six months in advance based on the color of what's coming out then in nine months. I just can't imagine living in a world in which you are planning so far advanced everything from what you say and how you say and what you look. But then I also think about like she is herself, like herself a multi-billion dollar business. It's like she is like if Amazon was a person, she's Amazon. So like imagine if Amazon didn't plan 10 years in advance. They couldn't. They plan that far in advance. So it is, it's just a

crazy concept that you have one human who's a multi-billion dollar business. And then that human from what she wears to how she dresses, to where she appears, to what she does, to how she talks, the lipstick she wears, the color she wears on her feet. Like, that does all be prepared. Yeah, she actually said once on Jimmy Fallon that her plans were three years plus in advance. So when she's planning a tour, when she's planning an album, that means, from a very, very, very early stage. She knew about all the re-releases that were going to be happening. You know, when she went off the grid for a very long time, when she moved to Europe,

she deleted everything from her Instagram for so long. How long? Probably like a year. So she just vanished from the planet for a year? Oh, she vanished from more than that. But like her Instagram was like literally she like deleted everything. And then she hadn't been posting for forever and then deleted everything. And then, you know, when people used to, you'd pull up your Instagram and you'd see like the three pictures in a row.

And that would be like a bigger photo. So she did that. And so the first one that came out, it looked like a little like black corner and then a scale. And then that she posted into a perfect square of nine. And that was the reputation era. That was when she came back. Yeah, but no one knew what the hell it was. It was like, why is there a gold snake?

And that's the only thing on your Instagram. So we obviously knew like a new album was coming. But that was like the biggest switch up. But again, like, you know, with the eras tour, when she comes out on stage, there's all these different doors. And like there's different eras of her, like dancers are dresses like debut Taylor, Evermore, Taylor. And the very last door was an orange door. And so for literally any other artists, you'd go, that's just an orange door. But that was, she'd enter an exit through it.

So it's because that's where the life of a show girl was the next era. And we didn't know that. How many artists, how many like realistically can you take a year off? How do you take a year off and then still become one of the most be one of the most relevant people on the walking planet? Like that seems while she takes that year off or the couple of years off, do you think she's still working every single day? Or what is the what do you think that looked like? Well, she from a music standpoint, she took way more than a year off. But like on Instagram it was at least that. I actually think it's so smart because it's like over exposure. It's like when you have any art. You know, you look at like the big ones like, Ariana Grande, Billy Eilish, like they're not dropping albums every year because people get annoyed of you. Like when they can't help that the radio only plays them every 10 seconds.

So I think that Taylor knew that at the end of the day, if she didn't go away for a little while, she was never going to be able to recover from public perception with like the Kanye stuff. So her being gone for as long as she was, I think allowed her to plan for a very long time. But also people's attention span I think finally moved on from hating her and we're ready to re-receive her. And, you know, she got

some block with the overexposure of Travis. But she's been on an uphill climb since, since she came back. When she said she's planning her life years in advance, you think that's actually true? Absolutely. How? Well, you kind of compared it to Amazon, which is true. Like Taylor Swift is a business, 100%. But I think that when you actually listen to her talk, like she's kind of a nerd. She loves the intricacies, the articulation of, like, her own life. And in that New York Times thing when she was talking about how like she just tries to be as observant as you are when you're 16 years old. And everything is a big deal and everything means something. So while it is strategic for, of course, money, of course success, of course fame.

Like she wanted to be, she doesn't ever hide that too. Like when she was like 13, she was like, yeah, I just want to be famous. And if I am, I will never, ever, ever take it for granted. and she hasn't. But I think she also gets that little scratch in her brain itched when she can be like, I know how much people will love knowing that I did this because I care about their experiences as a fan. Amazing. Years in advance. All right. Speaking about years in advance, wedding, we hear that MSG is the place. That's the news that has come out since we've had this podcast. Will her and Travis get married at MSG? What do you think? If they do, I will be shocked.

I think that is... Why? It's so not her. I mean, I know that there's supposedly a thousand people coming to the wedding, but there's plenty of venues. Someone would build a venue in six months if they thought Taylor Swift wanted to get married there. But MSG just is like, okay, I do.

I've been a stand of Taylor and Travis since Day 1. I love him so much. I love them together. But like MSG is giving Travis Kelsey would get married there. Yeah, like she doesn't get like a, what? It's like two bros would get married there. Like Taylor, so like she is so whimsical and like what her dress is going to look like and that's just not going to fit in MSG. So I think it's a diversion. Well, the only thing is you need at that level, you need enclosure, right? You can't have, like I remember Sarah Hyland's wedding and Wells Adams here talking about how there was someone, who flew a drone or something, or there was someone who was like sneaking in, like over, like literally sneaking in with a camera to get stuff. So you think about her, it has to be enclosed. Like there can't be any just a free outdoor space because there's too much risk. That's one.

Two, you need infrastructure that can have like the biggest and best security in the world. And three, it's got to be in a place that's like accessible to some of the most powerful people in the world that'll be there. So like your options become very limited. Like I know you're She's giving this face right now if you can't see. But the face is like, oh my God, no. Please tell me it's not MSG, please. But like where else could it? Where else could you get all that stuff?

Surely there are enclosures that can hold a thousand people that are not visible to the public. Yeah, yeah. But I think that you think about like the level of security you need is pretty much for something like that, is the level of security you need for like a president. Right. Think about how people with wealth have access. No one has more access because of wealth and her public poll. She could build her own security team and have, I don't know.

I just feel like it, I mean, listen, if she gets married to MSG, she better spend $100 million transforming it because those photos would be so ugly. Like how do you make a concert venue or a sports arena look pretty enough to get married? Especially when you compare like her engagement photos. Like how do you make, how do you create like that artistic vibe in a place like MSG? That would hurt. That would hurt me for her if it was. Would you get married in MSG?

I would not get married. Wow. Catherine really would not, but Taylor Swift would. I would marry you anywhere, but I really prefer to not get married. That's sweet. I love it. Unbelievable. All right.

Well, anything else on the Taylor Swift run we need to talk about? No, but we do need to listen to the song. I still haven't listened to it. That's really good. I'm going to listen to it. While I listen to it, I also want to give a shout out. We're on this European tour here. Santorini, then Lake Como.

From Lake Como, we are going to Tuscany, Tuscany to Florence, Florence to Venice, and then we are going to Croatia. Croatia, we are then flying into Nice and going to Cannes, for the Cannes Film Festival on the creative side. I'm speaking at a few panels and attending a couple events,

looking forward to that, and then back home to the boys, who we desperately desperately miss. But I want to give a shout out to Papua. So, Papua 2i is, did you know this? That the Rock's Cologne, they reached out to me to partner up with? You know that? You want to know another fact?

Evan told me, I kind of felt embarrassed when he said this because he's like, dude, you're never going to believe it. And I was like, what? Because he said in front of a group and I'm like, yo, shut up. I didn't say something like that. But he goes, he goes, I talked to the team at Papatouille. And I just asked him a random question. I said, be real with me, be honest, because we know the answer is no.

Does the rock know who Jason is? And they said yes. They said yes. Probably, honestly, what they did was they gave him a list of everyone that's going to be promoting and working with him. And he was probably like, okay. So that's probably the most of it. But he is a dream guest for the podcast, you know. I feel like you should just lean into the fact that he knows you.

Just will that into the world? Just own it? Yeah, I just own it. Hey, they said it. Yeah, be like, he's kind of my friend. We're friends and we're going to get him on the podcast. That's manifesting right there. But Papatoui is his new luxury cologne. And the three cents I have are P21, smoke and bourbon. Give this a little smell here. Catherine, tell me what you, when I spray this, tell me what you think. Oh, I like that one a lot. It reminds me that it would be titled like cashmere. Does that make sense? Okay, here we go. This is scent number two. Yeah, isn't that nice? That's like a nice like dessert with a whiskey or something. Okay, this is P-O-1, P-0-1, leather and woods. We'll spray over here so you can have like a new fresh smell.

Oh, that's very clean. Yes. That's like you just got out of the shower and you smell so good. That's giving like jumped into Lake Como coming out. Okay, the last one is P-07. This is Amber in Cyprus, okay? Also, these bottles are beautiful, hey? Yeah, they're very aesthetic.

I love our tough. No, this has got a very luxury feel to it. Okay, here we go. P-07. This is Amber in Cyprus. Ready? It's right over here. We got a lot of smells brewing over here. That was also very, very clean. This is giving like nice dinner. Nice dinner. Nice dinner. Good bottle of wine. Okay. Sounds like I should wear P-07 today. That's the Papatoui Amber in Cyprus. So of our lineup, all the spots, what has been your favorite memory so far? Favorite memory so far? We're only several days in, but your favorite memory so far.

It might be last night. Because the first couple of days, like so much was planned for us, like the catamaran. Like, you can't beat that. The views were insane. We had so much fun, good music, like hanging out with our friends. The wedding was also just spectacular. Congrats, Mel and Evan. But I think...

That wedding. Holy shit. Absolutely magical. But I think that getting here yesterday, we had to rent a car. There's travel. there's some stress. And so just being able to like walk out into this city and find a cute little Italian spot felt like just very us. And it was just the best dinner, the best wine and then getting stuck in a rainstorm. It was just really romantic. And we had great conversation. Yeah, we probably got there. I don't know, let's call it 738. We left at like maybe 1130. Last one's in the whole place. In the middle of this dinner, a massive rainstorm comes in so much that it hails. Everyone clears out. We keep ordering wine. the owners and end up like sitting down having dinner behind us. Not even, we're like, they don't even care that we're here.

Like we would have had to app, like we went to their table like, hey guys, can we get our check? That's the European way. But I just don't know if I've ever seen a place as magical as Lake Como. No. I also felt like not only did they not really care that we were there. It was almost like we were like mildly inconvenience. Like when I asked for the final glass of wine, she was like, what?

And I had to ask like three times. So it was just kind of like, we were just, hanging out there intruding on their space at the end. But it was, yeah, it was such a good night. I think the sunset cruise, I posted on my Instagram, but the views from Santorini, looking at the Greek island of Santorini from the water. The water is the most beautiful, magical blue you can imagine. And I mean, just like, I've never seen anything like it. Like, you've got to go to my Instagram and check out that sunset cruise. That was amazing. And there was something, like, here's how I would describe Santorini sexy. Like, Santorini's sexy. In Santorini, you know,

it's Santorini. Santerini is sexy, okay? Here's how I describe Lake Como. It's just romantic. Yes. This is beautiful. Like, you know what I'm saying? Like, you bang in Santorini and you make out in Lake Como. Yeah, I'm going to, I'm just going to let you lean into that one. I concur, though. You are correct. Okay. I also, this is a finance podcast,

so I do have to give some trading secrets on the podcast side with finance. The best way to travel when you are traveling abroad is to use point multipliers. So what does that look like? For American Express, I have strategically, oh, this is a little Taylor Swiftish several months in advance. I knew that we would have huge costs. So I got a new American Express card with a good introductory bonus, 350,000 bonus points if you hit the certain dollar amount. I knew that we would hit that dollar amount with furniture.

So all the stuff for the house has gone on this credit card. And I've earned 350,000 point multiplier. Now, while I'm just, can you do me a favor as your internet working? Google the value of 350,000 AMX points. While you're Googling the value of those points, at Hilton, they did a bonus transfer where I could transfer my American Express points to Hilton. And for every thousand points I transferred, I got 2,400 points from Hilton. I then went to one of the nicest Lake Como hotels.

I looked at how much it was per night in points while we're staying here. It's around 1.3, I didn't even tell you this, 1.3 million on average points to stay there. but on Friday night it was 170,000 points. So I took roughly around, I think it was like, I don't know, I ever do the math. It was like 70,000-ish points from Amex, transferred them to Hilton. I got 2.4 X that. So then based on the points I had, that it gave me enough 170,000,

and I got that room on Friday night in Lake Homo. That typically goes for over a million points with the bonus transfer and timing it right. going on the right night, it's pretty sweet. So one of the big things you can do with airline points, MX points, all different points is they will have transfer opportunities. We will get multipliers if you take your points from like, let's say, that airline and bring them to another airline. It's like buying loyalty. So you can do, you can get like three, four times points at the right time. Is there a service that like teaches you this or does this for you? Well, the points guy. I mean, I mean, first of all, your answer is there's a lot of services. The one I recommend because he's

been on the podcast twice now is the points guy. He's got an app. You can go on there and they can have calculators. They can do all this. They can help you through this all and calculate like what the value your points are. Did you did you did you did you did you get it up? 350,000 points. 350,000 amex points is equivalent to what? $2,500 is a statement credit. $3,500 when redeemed for flights through MX travel or 35 to 7,000 plus when transferred strategically to airline or hotel partners roughly one to two cents per point, sometimes higher. a premium cabin flight. See, there you go.

The transfer was the biggest value there. So that's what you got to do. You got to do that transfer. I'm going to leave that point transferring to you. Point transfer guy. The other thing too is, oh my God, do you want to know how much? We did not buy these, by the way. We did not buy these.

A laydown flat to go from JFK to Athens was $13,000 per laydown flat or $450. thousand points. Absolutely insane. We sat and we had our own two chairs in economy by ourselves. We put the arm seat up. It was fine. It wasn't the best, but it was fine. Yeah, travel is never going to be your favorite, anyone's favorite thing to do. So I would rather have a slightly less comfortable flight and spend money on other things than like splurge. I know some people are very much the opposite that, but I would have to be like a billionaire to and $30,000 on a flight. That's just just down the toilet to me. 13. Well, especially when the alternative is like less than a thousand dollars.

You know, you look at the alternative of an economy flight. It's like less than a thousand dollars or 13 to 14,000 to lay flat. Like, get the fuck out of here. It's crazy. This reminds me of like when people like will dog on like men more in particular. But like, we used to go to war. Like we can, we're still in, well, we're literally in war. But like when we think about making ourselves uncomfortable for a little while, like, we can do it. We don't need to lay down for an eight hours. Deal with it. And the way to beat jet lag, by the way, take a red eye, land and go right to it. So we land and we went right to the catamaran. We were so tired, powered through, but then got to bed at that night. I slept probably 12 hours

the next day and on where we are. So Euro 2026. Next stop is Tuscany. We have a long time between now and Tuscany. But Catherine, thank you for joining me on this three. 30 minute Thursday, David, we missed you. But Catherine, always, always a pleasure. Got anything you want to leave us with? No, just happy to be here. Happy to have you here. Hope you guys thought this was another episode of training secrets one you couldn't afford

to miss.