
Every February 14th, millions of people rush out to buy heart-shaped chocolates, overpriced roses, and mass-produced cards, turning Valentine’s Day into a global cash grab. But how did a once obscure tradition become a billion-dollar industry?...
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Donald Miller
Foreign.
Kyle Reed
You're listening to the why that Work podcast, presented by StoryBrand AI. If you've ever wondered why certain brands, trends, or cultural phenomena find success while others don't, you're in the right place. Every week, we unpack why something worked, then give you actionable insights that you can use in your own life. Now let's dive in with your hosts, Donald Miller and Kyle Reed.
Welcome back to the why that worked podcast. Episode six, February 10th. If you're listening to us in real time. And. And I thought no better topic to talk about because it's Valentine's Day week.
Donald Miller
Valentine's Day. I have to point out that that's the first time you've said Valentine's Day correctly.
Kyle Reed
I started doing this.
Donald Miller
You're a Valentine's guy.
Kyle Reed
I didn't realize until you called me out, but I just. I think I didn't realize it.
Donald Miller
Nobody has ever called you out.
Kyle Reed
I just say it so fast that I kind of get through it, but I had no idea I was saying it.
Donald Miller
You know whose fault this is?
Kyle Reed
Whose?
Donald Miller
Your second grade teacher.
Kyle Reed
Probably so. Well, interesting enough, in second grade, my dad chose to move me to homeschooling. So it's my dad's fault.
Donald Miller
So it's your dad's fault.
Kyle Reed
Everything comes back to your dad. Right.
Donald Miller
He wanted it to be Valentine's Day.
Kyle Reed
Valentine's Day.
Donald Miller
And he didn't want.
Kyle Reed
And no one corrected.
Donald Miller
He didn't want the government institution of school to teach.
Kyle Reed
My mom would always say, put it in the washer. Machine.
Donald Miller
Washer.
Kyle Reed
So Indiana, very Midwest. So Valentine's Day, something. There's something there with that.
Donald Miller
The washing machine, but also Walmart instead of Walmart.
Kyle Reed
I don't say that, thankfully.
Donald Miller
Yeah. We had Kmark and Walmart.
Kyle Reed
Kmark and Walmart. Yeah. That's good. Well, there you go. A little bit more. The more you know about us, the better. Right?
Donald Miller
Here's a question for you.
Kyle Reed
Yeah.
Donald Miller
What percentage of marriage proposals take place on Valentine's Day? Or as you say, Valentine's Day.
Kyle Reed
Oh, my goodness. So not to offend every person listening to this, who has proposed on Valentine's Day?
Donald Miller
Be careful.
Kyle Reed
But is that, like, on the level of, like, proposing at a stadium on the Jumbotron? Like, it's pretty cheesy. Cheesiness.
Donald Miller
It is. My wife told me she knew we were gonna get engaged.
Kyle Reed
Yeah.
Donald Miller
You know, I sought permission from her father, all that kind of stuff. And all she told me was, if I'm on a Jumbotron, the answer is no. She wanted to be Quiet.
Kyle Reed
Did you surprise her? No.
Donald Miller
Yeah. I listened to my wife when she says, don't do this, I don't do it.
Kyle Reed
So what's the number? How many?
Donald Miller
10%.
Kyle Reed
10% people propose 10%.
Donald Miller
6 million couples a year get married on Valentine's Day.
Kyle Reed
Engaged.
Donald Miller
Get engaged on Valentine's Day. Is that surprising to you?
Kyle Reed
Yes and no.
Donald Miller
Makes a lot of sense.
Kyle Reed
It's kind of a layup for most people of, like, the natural, like, progression is. We should. I'm gonna propose on Valentine's Day. Christmas has got to be, like, right behind that too.
Donald Miller
You really think Christmas is a big one?
Kyle Reed
Yeah, People, they go home. It's this whole thing.
Donald Miller
Wow.
Kyle Reed
You know, I think Christmas would be.
Donald Miller
Right behind that, maybe higher, but that's interesting. I just didn't think it would be. It feels cliche to me.
Kyle Reed
Oh, totally.
Donald Miller
It feels like if you're getting. If you're getting engaged on Valentine's Day, are we gonna. We're gonna get in trouble for this? I just feel like it lacks creativity because there's.
Kyle Reed
There's some guy out there right now going, that's what he was planning this week. And we might have just shattered his entire. You go for it, man. Go for it. Join the temple.
Donald Miller
Because who the heck are we?
Kyle Reed
That's right.
Donald Miller
To tell you what to do in your love life.
Kyle Reed
That's right. I started with a jumbotron plan. And did you really? No.
Donald Miller
Were you gonna.
Kyle Reed
No, No, I didn't. I knew I was well enough. I knew well enough to go there, though. My mom.
Donald Miller
How long did you get engaged?
Kyle Reed
Let's see. 11 years ago.
Donald Miller
So you and I are the same. I mean, well, I've been married 11 years, so you to be.
Kyle Reed
Well, I'm coming up on year 11 of marriage, I guess. 12 years ago.
Donald Miller
We're exactly the same.
Kyle Reed
Wow.
Donald Miller
Yeah.
Kyle Reed
In so many ways.
Donald Miller
And so was there a cool. How'd you do the engagement, though?
Kyle Reed
I. I wanted to surprise my wife. I liked that. And so I had. We had some friends. You know them? The Whitakers. Carlos Whitaker.
Donald Miller
Yeah.
Kyle Reed
So his wife Heather was big, and, like, she'd throw these, like, elaborate parties and fun things. So I use that as my guys of, like, Heather's throwing this party in a park, and we're invited, and we need to just bring a bottle of wine, and we're gonna go to this park. And so we're driving to the park.
Donald Miller
Yeah.
Kyle Reed
And when we pulled up, I had rented out this, like, camp space, and it was all set up, and that's why I Surprised her.
Donald Miller
Were there a bunch of people there?
Kyle Reed
No, just me and her and foot. A friend of mine.
Donald Miller
Friend of yours set up like, okay, gotcha. Hiding in the bushes and interesting of.
Kyle Reed
Heather actually helped set it up. So she was.
Donald Miller
And she said yes, and the rest was history.
Kyle Reed
She said yes, and then we went back to. I flew all of her family in to surprise her.
Donald Miller
Very good.
Kyle Reed
So, yeah.
Donald Miller
So it worked out very good for you.
Kyle Reed
Thank you.
Donald Miller
I did the. We were in D.C. betsy was living in D.C. and I chased her to D.C. and so I took her to dinner at the Kennedy Center. You ever done dinner at the Kennedy Center? There's a restaurant up there with shag carpet. Like, I don't think since Kennedy was killed, John F. Kennedy was killed, they've changed a thing. Like, I don't think they've moved any art or. It's literally like bright orange. Red, red shag carpet.
Kyle Reed
What's it smell like in there?
Donald Miller
It smells like 100 years of old people.
Kyle Reed
Okay. Yeah.
Donald Miller
I mean, it's little. Like, there's busks of presidents and things. And so we did. I'd never scouted it, so I didn't know. And it wasn't the most romantic thing. And then we started walking around that beautiful balcony and it just doesn't feel right. Just doesn't feel right. And my wife turns and says, oh, I love that sculpture. There was a sculpture of John Kennedy's head and pre assassination because it's just cleaner. But they, you know, there's a sculpture of his head. And my wife says, is it too soon? My wife says, that's my favorite sculpture. And I remembered plan B was to go to the Einstein sculpture on the Capitol Mall. And it was the same sculpture who'd done it. He has a very specific style. And my wife, that's her favorite sculpture in D.C. and I'm like, okay, plan B. We're going with plan B because this doesn't feel right. There's too many people around. We get in the black car, they take us over to the sculpture, and there's people all over Einstein. And I'm like, dad, gumm it. Like, there's a bunch of kids. She doesn't want it to be. And not only that, the sprinklers are on on the sidewalk getting to the sculpture. So we're gonna get soaking wet. We're gonna get there as a bunch of people. And I literally. The true story, Kyle. I pray. I said, God, I gotta do this now. And I gotta do it at that sculpture. You gotta help me. And we're getting out of the car. Open the car. She gets up. The sprinklers literally die. And every single person, probably not exaggerating, probably eight people walk away, and the sprinklers die immediately. We walk on the sidewalk, and there's nobody there. And I get her down on one knee. She says yes. I stand up, I give her a hug, and like, six or eight people just walk up, and they have no idea what just happened. And my wife got her little personal thing, her personal moment. So we got married at that sculpture.
Kyle Reed
You're romantic.
Donald Miller
We got engaged.
Kyle Reed
Yeah.
Donald Miller
Wow. I'm strategic.
Kyle Reed
Yeah.
Donald Miller
I hope I'm romantic. But I knew, like, it's gotta be special. It's gotta be memorable. We gotta be able to drive by it someday and go, your mom and dad. Like, I can't wait to take Emmaline there when she's old enough.
Kyle Reed
My natural reaction would be like, look at all this I planned for you. I got them to turn the sprinkler, you know?
Donald Miller
But the fact that the sprinklers died and everybody walked away, that's amazing. I was like, it's almost like God.
Kyle Reed
Said, okay, I've gotta do this for him. That's exactly it.
Donald Miller
That's exactly it. Well, not just that, but, like, the boy's an idiot.
Kyle Reed
Yeah.
Donald Miller
He literally wanted to do this at a public park, and he thought he would have a private moment. I gotta help this boy out. Cause he's never gonna get married. Which is like, this is not how you make babies.
Kyle Reed
This ties into Valentine's Day because Today's.
Donald Miller
Episode, Us, 30 minutes later.
Kyle Reed
Us stupid men need a day. Yeah. Nothing like two to remind us to celebrate.
Donald Miller
Two guys on a podcast explaining the ways of love is gonna be a hit.
Kyle Reed
It will be, I think. Now, here's what I found about this day. Valen St. Valentine. What did you.
Donald Miller
Did you. Not to be confused with St. Valentine, who invented the clock?
Kyle Reed
Great guy for the Catholic church.
Donald Miller
He had a big.
Kyle Reed
That's pretty good.
Donald Miller
Remember Flava Flav? This saint had a big clock around Flava Flav. Got it.
Kyle Reed
That was almost as good as your JFK little joke.
Donald Miller
You guys better not cut that.
Kyle Reed
No, we won't.
Donald Miller
By the way, the listeners should know they neuter me every episode. I rightly deserve. I rightly deserve to be canceled every time we turn the microphones on and I get neutered to save their jobs. They could care less about my reputation. They want to keep their jobs, so they neuter me.
Kyle Reed
It's strategic.
Donald Miller
Don't take the Kennedy head, you know, bit off. Don't take the Kennedy head bit off.
Kyle Reed
Send your. Send your letters to Donald Miller at StoryBrand 3.
Donald Miller
Yeah, just put 3 on the envelope. It'll get to me.
Kyle Reed
So here's what I found fascinating about this date. The history is interesting and we could talk about that for a little bit.
Donald Miller
Yeah.
Kyle Reed
What was more interesting for me at least, of why this day works. Because I'm not even gonna say what it's called anymore because you make fun of me. This day on February 14th works to some point. It made it across to America and it became commercialized really quickly.
Donald Miller
Well, but we gotta go back to Roman times because it was a pagan. It was kind of a pagan sex holiday. Lupercalia. If that's how it's pronounced.
Kyle Reed
Sounds right.
Donald Miller
Cooper. Lupercalia. Oh, he got you. We're getting a thumbs up. But it was sort of a pagan sex thing. Celebrated in mid February, the pagan festival honored fertility and the coming of spring, featuring rituals that included the clean version, the pairing of couples.
Kyle Reed
That's a great way to start.
Donald Miller
And the Christians came along and made it family friendly.
Kyle Reed
Thank you. As they do. Safe for the whole family.
Donald Miller
Those pesky Christians came along. To which we are all grateful, by the way. The last thing we need is a bunch of debauchery in the streets.
Kyle Reed
That's true.
Donald Miller
Yeah. But that. Now, is that what you got when you looked into it?
Kyle Reed
That's kind of early on, the story of St. Valentine. And there's some. I think. What did the conflicting stories about? You know, there was a story about him helping two couple in jail. There's also a story about he sent a letter to a love interest and signed it your valentine. So there's some different things there, if you notice.
Donald Miller
You go, I've heard there's been lots of St. Valentine's yeah.
Kyle Reed
Okay.
Donald Miller
The story that I heard was that he was one of the St. Valentine's or whatever he was at the time, was secretly marrying Roman soldiers because they weren't allowed to get married. And so he was marrying them on the side. And that's why he was executed.
Kyle Reed
Oh, okay.
Donald Miller
That's why the Romans executed.
Kyle Reed
Interesting.
Donald Miller
Yeah.
Kyle Reed
Like what? Like that was 400 or 500 is what I read.
Donald Miller
I don't know the date. 5th century.
Kyle Reed
5Th century.
Donald Miller
Yeah.
Kyle Reed
That sounds good.
Donald Miller
It was under Pope Galatius.
Kyle Reed
Here we go. Fifth century.
Donald Miller
496 AD is when he was killed.
Kyle Reed
Yes. They declared February 14th Valentine's Day.
Donald Miller
If you want to be famous for a really long time, just make sure. The Romans kill you. If you really want to be famous, come back from the dead a few days later. That's a great.
Kyle Reed
That's a good plot.
Donald Miller
That's a good way. It's a great way to. It's a good way to get name recognition. That. And be the son of God.
Kyle Reed
Yeah, that helps.
Donald Miller
Or be a virgin and be pregnant. That's another one. Great tactic. Talk about building a brand. Building a brand with.
Kyle Reed
I can tell you, cold plunged this morning.
Donald Miller
I got a lot of dopamine going through my face.
Kyle Reed
It's working.
Donald Miller
Oh, that's an episode. Cold, plunging.
Kyle Reed
Write it down.
Donald Miller
Okay, so Valentine's Day. Yes.
Kyle Reed
Let's get back to the subject now.
Donald Miller
But you're saying that the reason though, that it's here, which is always. It always comes to this on this podcast.
Kyle Reed
Yes.
Donald Miller
The ability for people to make a living. It's not the money that I'm talking about. Everything that we talk about is always like, okay, but how are people getting rich off of it? Because that is the number one telltale sign that something's gonna take off. And it's not about the money. It's about the ability to provide a living for you and your family off of this thing.
Kyle Reed
Yes.
Donald Miller
And Valentine's Day has done that. Did you get stats?
Kyle Reed
Yeah, we've worked on an episode about Michelin stars upcoming. And in that episode we kind of hinted around the same thing where they created this system to get people out driving on their tires, right?
Donald Miller
Yeah, it was about selling more tires.
Kyle Reed
One of the things I found. So Richard Cadbury, that name sounds familiar, right?
Donald Miller
Are you kidding? Is he the egg guy?
Kyle Reed
1860, created the first heart shaped box of chocolates. Damn. Tied it to Valentine's Day.
Donald Miller
Ka Ching.
Kyle Reed
Well, what's interesting is I'm always very fascinated about these people who see a problem in the market of going, how do we get more people to think about us? And then they strategically walk away and come up with a strategy to get them to think about that. The other thing I found interesting was the kind of go through history, even the way that they use Hollywood kind of in the late 80s, early 90s of like movies like you got Mail, Sleepless in Seattle, they kind of. They really played up this idea of Valentine's Day being a massive day of grand gesture of love. And it's like fascinating to watch that.
Donald Miller
So we would have to say the. The monetization of it, but also the existence of love, period. I really want to do an episode on why that worked on monogamy. I Think it would be fascinating to do an episode on monogamy and to get into all of the structures of how love between two humans works is both in a Darwinian sense and also a spiritual sense. But you would have to say that love is something that people want. Expressions of love is something that people want, especially women. Did you know that 60% of the roses bought on Valentine's Day are bought by women? Would you have predicted that?
Kyle Reed
No. Well, no, but I'm just deadbeat dudes.
Donald Miller
Is what that tells you, you know?
Kyle Reed
Well, that even spit moves into the rise. Like Galentine's day was a whole other spin off of it, right?
Donald Miller
Yep.
Kyle Reed
So that's interesting.
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Donald Miller
250 million roses are purchased on Valentine's Day. It is absolutely unreal.
Kyle Reed
So many.
Donald Miller
The flower market in Amsterdam. Did you know this about the flower market? If you. If, like I lived in Oregon, there was a tulip farm near us, and they made tons of tulips. If I went to Whole Foods and bought tulips, those tulips likely went from that farm physically to Amsterdam and back to the Whole Foods down the street. There's a physical flower market in Amsterdam that it's a giant rotating stage and hundreds of guys sit there with computers and they look at these flowers and they bid on them and they buy them for their various distribution networks and then they get distributed all over the world. And so can you imagine the influx of flowers at that market around Valentine's Day in the three weeks before Donald's? But it's like Christmas for them.
Kyle Reed
Yeah. That makes their whole quarter, right?
Donald Miller
Yep. 250 million roses.
Kyle Reed
No, I did not know that.
Donald Miller
Astronomical $2 billion worth of candy and chocolate are sold specifically for Valentine's Day. Okay, just guess how many Valentine's Day cards are exchanged in the United States.
Kyle Reed
This is where you're gonna. This reminds me of the population of.
Donald Miller
330 million, but that includes children.
Kyle Reed
I'm gonna look dumb here.
Donald Miller
I think you're gonna get it pretty close.
Kyle Reed
That's so much pressure. I say Valentine's Day so you.
Donald Miller
Much fewer Valentine's Day cards.
Kyle Reed
There's a market there. We need to work.
Donald Miller
There is a market for children.
Kyle Reed
I don't know. 800 million.
Donald Miller
There's 330 million people. They're each buying, like, three cards.
Kyle Reed
Well, I'm thinking, like, kids, classes. They could buy multiple. Okay, 200 million.
Donald Miller
You just ruin everything.
Kyle Reed
I know.
Donald Miller
145 million.
Kyle Reed
Wow.
Donald Miller
That many.
Kyle Reed
That's like when you walk home and your wife's like, guess what I did today? And you're like, there's no right way to answer this question. I'm going to just shoot high and hope that she doesn't hate me for my. Yeah, okay, say it again. How many?
Donald Miller
145 million.
Kyle Reed
Okay, so here's. That's interesting. Here's the.
Donald Miller
30 million people will dine out. 30 million couples will dine out.
Kyle Reed
That's massive. You better book your reservations for Valentine's Day. Right now.
Donald Miller
Valentine's Day is an easier time.
Kyle Reed
Okay, here's something I found. I don't know if you came across this, and I found it fascinating. The rise of the Industrial Revolution and the connection to Valentine's Day.
Donald Miller
I did not see anything about that in my extended research that I E. Conversation with Cooper walking here down the hallway.
Kyle Reed
That moment when we industrialize everything and we started to commercialize things was really when Valentine's Day took off.
Donald Miller
And I imagine a lot of other things.
Kyle Reed
Yes, absolutely. But it took the factory worker and gave them a day. But it also. The factory process of all the stats you just read, helped bring that industrial. Into a massive business for Hallmark, Cadbury, the flower. You know, the tulip shop in Portland, Oregon, that the rise of the Industrial Revolution was a massive inflection in that. In this holiday.
Donald Miller
Well, it probably turned a lot of things into sort of processes and monetization. And by the way, this is not a knock on that. I love the fact if you want something really wholesome and good to take off in the world, figure out how to monetize it. Figure out how other people can make a living doing it, and that will rise. And so I've got. I love Valentine's Day. I've got a wife who I'm Crazy about, you know, I've married way, way out of my league. And now I've got a daughter whose heart has just like taken over my life. And, you know, and so I love the formal expression of this sort of thing. It is a complicated. There's some pushback. Did you get into that at all?
Kyle Reed
No. What's the pushback?
Donald Miller
Well, I mean, think about it. If you're a woman and you're single and this happens to be a year that you don't have anybody, you're not gonna go, oh, I'm really sad you're gonna go. This holiday sucks. Right. And so there's a pushback against the sort of Valentine's Day. But I think most of that is resentment about the personal situation that somebody is in.
Kyle Reed
Why do you think that is? Why is that such a tough day for some?
Donald Miller
Well, I mean, you know, if there was a day. If there was a day on the calendar when it was a given to express how much you respect men and you were ignored that day, that would be tough. That would be really tough. And I think a woman's heart is designed, by the way, to be adored. I really do. And I'm gonna get mail on this, but I just do. I think they're different and I think they're designed to be adored. And I think when a woman's heart is not adored, I think something is broken in the system and it is an injustice. You know, it's somebody not getting food. And by the way, if you adore a woman in an appropriate, respectful way, watch her flourish. Just watch.
Kyle Reed
That's right.
Donald Miller
Yeah. And so that's one of the reasons I really love. I actually like this holiday. Cause it gives you a formal reason to actually do it and to sit down and take it seriously. Especially guys, if you have daughters, like, your wife is really important. But teach daughters that their heart was designed to be adored and a good man will notice and she's gonna end up with a better husband someday. Cause all this riff raff she's gonna kick to the curb. Appropriately, yes.
Kyle Reed
As a dad of daughters as well, I love that. I think that's a great reminder. It's funn as, you know, kind of the dumb male in me of just like, you know, you kind of sometimes need like the reminders to cherish that. Yeah, you kind of need those markers on the calendar to remind you, like, hey, when was the last time I took my wife on a date or told her, you know, I loved her? All those things. Sometimes we need those reminders and I'm with you.
Donald Miller
I love the difference between. We should do a Mother's Day episode. Think about the difference between Mother's Day and Father's Day and how much money is spent on Mother's Day versus Father's Day. It's because the male heart isn't designed to be. It doesn't need it as much. It does need respect, and it needs, you know, I think that's a true idea, that men are designed to be respected and women are designed to be loved in general, of course, every woman needs to be respected. Every man needs to be loved. But I think that's the difference. And so, you know, there's these holidays that have taken off because supply and demand. There is a demand for the woman's heart to be adored, and it's taken off. It works because there's a demand and it was an opportunity for people to monetize it.
Kyle Reed
It's good.
Donald Miller
And they did monetize it.
Kyle Reed
There's also feels like, I guess, feels like moments of life where we need markers, you know, in our life to kind of just again, go back to that. Being reminded of, looking forward to something. You know, I look forward to our. To our anniversary or I look forward to Father's Day. I look forward to birthday. You know, you kind of have moments where you need to break up some of that monotony of life.
Donald Miller
Yeah.
Kyle Reed
To be reminded of, like, this is a chance for me on any given day to express something and go above and beyond or have a nice dinner or celebrate the idea of real relationship and love. And I think the commercialization, you could go down that path and go, oh, it's just greeting card companies making a lot of money, all the flowers and this and that. But there's something special about it.
Donald Miller
We would be amiss to wrap up this episode, and it is two guys talking about Valentine's Day. So it should cut short.
Kyle Reed
We are very aware of that. Again, send your hate mail to Donald at three. At three.
Donald Miller
What do you. What are your tips to guys and dads? I've got one. It's just super, super simple. Yeah, it's actually super simple. It's very, very difficult for guys to pull off. But I've got one.
Kyle Reed
Well, I think the. The one that comes to mind right away was something you had mentioned in your proposal story, and that is pay attention. I think a movement of attention.
Donald Miller
Yes.
Kyle Reed
Is. Is far more bigger than a piece of jewelry. You.
Donald Miller
Exactly it.
Kyle Reed
And so finding some way. Just listen, you know, there's going to be moments.
Donald Miller
This does not have to cost you a lot of money.
Kyle Reed
And any just paying attention and just being proactive in the sense of taking some charge of that moment. You know, I'm always tempted. The enneagram tune me is to go, where do you want to go to dinner tonight? And whatever she decides I'm good with. But, you know, again, paying attention to go. I'm going to put a plan together because I'm going to be intentional.
Donald Miller
Yes, I would say that's it. The gift. The biggest gift that you could give your wife, your daughter, is the actual premeditated attention to honoring them. And one of the best. Look, if I went down to, like, King Jewelers here in Nashville and spent $1,500 on some earrings, brought them home for Valentine's Day or 90 minutes, sitting down with a piece of paper and a pen and thoughtfully explaining what a gift you've been to me, my wife would have. She could care less about the now. She's not a very materialist. I'm the materialistic guy in our relationship. She's not materialistic at all. So the jewelry is not going to mean anything to her. But that letter would mean the world. Yeah, and I tried to do that. But the other thing is, like, imagine your daughters with, you know, your daughters are kind of that right age now, you know, I mean, and so imagine them having a little, you know, you get them a little pink shoebox of some sort, and every year there's a date on top of a Valentine's Day letter from dad. You are doing more to set her up with a great husband, because that's what she's going to look for. You know, she's going to look for somebody who's thoughtful and intentional and who adores her. That letter is not just a Valentine's Day letter. It's development. Yeah, it's development. And it's part of protection and provision. You're providing for her heart and you're protecting her from the yahoos that she's going to show no interest in. You know, if there's a vacuum in her heart, it's going to be probably filled with junk food, you know, in the version. That version of a man. And so I, you know, I think actually just sitting down and it's really hard for guys to do this now. I'm going to do something that is going to turn every woman off. Great lead. I think you can go to storybrand AI or Perplexity or whatever you can say, here's the way. Here's everything that I feel about My wife, here's every reason I'm grateful and actually sit there and do the work and type it and say, hey, will you write me a short letter? And it will spit out. Because guys aren't writers, and this is very important. It needs to be clear. And sit there and read it and go, okay, I would change this. I would change this. In other words, edit it rather than write it and then rewrite it. Put it on a piece of paper, sign it. You work just as hard as you would. And by the way, if you would have written it yourself, it would have been not very well written.
Kyle Reed
No, that's a great idea. You've done that in the past, where you even said, I'll sit there and do some work. Someone sent me a question or a letter, and I don't really know how to respond. I'm going to use. That's an actually really positive way of using AI to help you clarify something and work through that.
Donald Miller
AI is shockingly good at relationships.
Kyle Reed
Yeah, it's.
Donald Miller
Can I tell you a story where AI corrected me in a way that I didn't ask it to?
Kyle Reed
No.
Donald Miller
Okay. So my wife had something happen with a person that we worked with, a vendor that we worked with, and there was a little bit of a strain in the relationship. And so my wife actually bought a gift and sent it to her with a note saying, hey, so sorry for the tension. Just know we really appreciate you and respect you. And I thought that was a pretty cool move. Well, somebody emailed me. A friend emailed me, and she had offended a big socialite in her area.
Kyle Reed
Okay.
Donald Miller
And so it's too long of a story, but, you know, not that big of a deal. But she just emailed me and said, hey, how would you handle this? And I thought, oh, well, you know, my wife bought this gift for this person and sent a nice note. And I said, and I thought, well, you know, buy our gift. And so I said to my wife, I'm going to tell, you know, this woman to buy a gift like you did, because that seemed to work really well. And my wife said, no, no, no, no, don't do that. That's a completely different situation. This woman is wrong to have done this to your friend, and you do not buy her a gift. Makes you look weak. And I roll my eyes and I'm like, nah, it worked too well. You know. So I go to AI True story. I go to artificial intelligence, and I say, will you help me come up with what to write on the card to go with the gift? Here's the situation my friend has found herself in. Here's how she was wronged. Here's how, you know, whatever. AI came back and said, don't buy a gift. I didn't ask it. I said, give me the. Write me the card. And it literally said, don't buy the gift.
Kyle Reed
Are you sure Betsy's not in control? I think she might be.
Donald Miller
I think she might be.
Kyle Reed
She's the founder.
Donald Miller
Yeah. So you can actually go to. You can actually go to AI and say, hey, I'm a dumb dude. I'm not very good at speaking my heart. And here's. But here's everything that I feel now. The hard work is actually sitting down and putting on a piece of paper and handing it to them.
Kyle Reed
Oh, yeah.
Donald Miller
And it's a vulnerable moment, and it's going to make you extremely uncomfortable. That's the gift.
Kyle Reed
Yes, that's it.
Donald Miller
That's the gift.
Kyle Reed
You know, the earliest part of my life where I saw this in action was. I remember I was like, maybe 7 or 8, and my grandpa and grandma lived on a college campus. And my grandpa was the printer. This is back in the day where they printed everything. Right. So he's a printer. And my grandma was a secretary. She worked inside of the. Of the admissions office. I remember I was. I would love in the summer to go hang with my grandpa, but for some reason, I was there around Valentine's Day, and I was with him, hanging, helping him print stuff. Just doing all the things. And he handed me a bag of those. Awesome. I like them. Those little hearts, those little candy hearts.
Donald Miller
Oh, with the sayings on them. Yeah, Yeah.
Kyle Reed
I think they taste good. Hint, hint. To my wife. And. And he handed them to me, said he go give these to your grandma with a card. That was the early. Like, one of my earliest memories of those. Like, and now I think about it, I'm like, that was, like, kind of lame, but she loved it so much. And it was that simple act of just. I'm paying attention.
Donald Miller
Yes.
Kyle Reed
And that stuck with me to today of just that little moment of seeing that. And that kind of like what I'm. This conversation. Yes. Is two men trying to talk about Valentine's Day and being loving.
Donald Miller
You have to give. Now the women who are listening to this are rolling their eyes and absolutely loving it. Right. Because they. Yeah. Armchair experts on love. Two guys that, you know, they're interested in that.
Kyle Reed
But I think it wraps to a bigger thing of the word I'm walking away with is intentionality in relationships.
Donald Miller
There you go.
Kyle Reed
That's that's really what we're circling around. We can talk. We're using Valentine's Day to talk about this. The reality is, is when we think about relationships that are deeper. Friends, colleagues, spouses, kids. What I'm walking away with, even hearing from you, with your daughter, with your wife, is I want to be more intentional. I want to find ways to pursue them and love them and care for them and nurture their heart.
Donald Miller
Express gratitude. I am not me without you.
Kyle Reed
So, Don, why does Valentine's Day work?
Donald Miller
Valentine's Day works because the two main reasons are there's a need. It meets a need in the human heart, especially a female heart, not just females, but especially a woman's heart, to be rightly adored. I really believe that. I believe they're supposed to be adored, and I think they know it. I mean, how many times have you even. 11 years into a marriage, my wife will say something or do something. I look up at her and it's like the first time I've ever seen her. Now, I'm not saying this happens often. I'm not like a mushy, romantic guy, but I'm like, holy crap, that woman is gorgeous. Right? She's designed for that. Guys are not designed for that. Guys are just trucks. It's like you can use it to move a lawnmower around. It's very useful. And I will argue that till I die. Men are useful, so stop knocking us.
Kyle Reed
That doesn't bother me. Yeah, I like it.
Donald Miller
So I think that's reason number one. And reason number two, millions of people could make a living off the monetization of this expression on a specific day. Right. How much money does the Hallmark store make? Right. And because of that, it's sustainable and it grew.
Kyle Reed
Yeah.
Donald Miller
And then the myths about, you know, some. Some saint somewhere. The reason, like, nobody knows about that guy is because it's not actually that important.
Kyle Reed
Yeah, yeah.
Donald Miller
They found that stuff was necessary to make it work. That's my. Those are my two reasons. You got anything different or you.
Kyle Reed
No, that's. I think that's great. That, that. I think that wraps up really well why this day is important. But also happy Valentine's Day. Thank you.
Donald Miller
Happy Valentine's Day.
Kyle Reed
I'm working on that card.
Donald Miller
Just you for me?
Kyle Reed
Yeah, sure.
Donald Miller
Well, I want the little candies. You know, there's nothing that really says I didn't think about you more than a heart shaped box of candy. I thought about you while I was getting some Rolaids at cvs and I want to tell you this right now. I want to tell you right now. I would accept that from you.
Kyle Reed
That's fine.
Donald Miller
A heart shaped box of chocolates.
Kyle Reed
I'll take any candy you want to give me. Yeah.
Donald Miller
Because I'll put them all in a bowl and heat them up in the microwave and put some peanut butter on top. And those candies taste just as good as anything else.
Kyle Reed
Perfect. Because men are trucks and we're very simple. That's right.
Donald Miller
Put on some football.
Kyle Reed
Yeah. Well, Happy Valentine's Day to everyone listening to this. Hope you enjoyed this.
Donald Miller
And Happy Valentine Day, a lesser known holiday that takes place in August.
Kyle Reed
For the 10 people out there who celebrate Valentine's Day, all of you are.
Donald Miller
Big day for us 8 years old and under. God bless everybody.
Kyle Reed
Thanks for listening to the why that Worked podcast presented by StoryBrand AI. If you like the show, follow wherever you get your podcasts. And if you're Enjoying this on YouTube, hit that subscribe button and leave a comment letting us know what you think and what you want the guys to talk about in a future episode. Curious about how StoryBrand AI can help you create clear, effective messaging? Well, you can try it out right now and create a free customized tagline for your business. Just go to storybrand AI. Thanks for listening and we'll see you next time.
Podcast Summary: Why That Worked – Episode #6: Valentine’s Day—The Surprising Economics and Evolution of Love’s Biggest Day
Introduction
In Episode #6 of "Why That Worked," presented by StoryBrand.ai and hosted by Donald Miller with co-host Kyle Reed, the discussion centers around Valentine's Day. Released on February 10, 2025, the episode delves into the historical evolution, economic impact, and the enduring significance of this widely celebrated holiday. The hosts explore why Valentine's Day has persisted as a major cultural and commercial event, dissecting both its romantic allure and the strategic monetization behind it.
Personal Anecdotes and Engagement Stories
The episode kicks off with Donald Miller and Kyle Reed sharing personal stories about their own marriage proposals, highlighting the blend of romance and strategy involved in making these pivotal moments memorable.
Donald Miller's Proposal: At [05:00], Donald recounts his proposal at the Kennedy Center in D.C., detailing how the setting initially felt unromantic until a spontaneous moment at the Einstein sculpture made it perfect. He shares, “We walked on the sidewalk, and there's nobody there. And I get her down on one knee. She says yes” ([06:00]).
Kyle Reed's Proposal: At [03:42], Kyle describes orchestrating a surprise engagement in a park, which involved renting a camp space and orchestrating a gathering with friends to create an unforgettable moment. "Heather actually helped set it up... we got her down on one knee. She says yes," he explains ([04:25]).
These stories set the stage for exploring the broader themes of intentionality and the importance of creating meaningful experiences.
Historical Evolution of Valentine’s Day
The hosts delve into the origins of Valentine's Day, tracing it back to ancient Roman times and its transformation over centuries.
Ancient Beginnings: At [09:21], Donald explains, “It was sort of a pagan sex holiday. Celebrated in mid-February, the pagan festival honored fertility and the coming of spring, featuring rituals that included the pairing of couples.”
Christian Adaptation: They discuss how the Christian church adapted the pagan festival to make it more family-friendly, moving away from its original themes of fertility ([09:57]).
St. Valentine’s Legends: Donald shares various legends about St. Valentine, including his secret marriage ceremonies for Roman soldiers, which ultimately led to his execution in 496 AD under Pope Gelasius ([10:31]-[11:08]).
These historical insights underscore how Valentine's Day evolved from a fertility festival to a day celebrating romantic love, influenced by cultural and religious shifts.
Economic Impact and Commercialization
A significant portion of the episode is dedicated to analyzing the economic aspects of Valentine's Day and how commercialization has fueled its success.
Market Statistics: At [15:10], Donald reveals that “250 million roses are purchased on Valentine's Day,” emphasizing the massive scale of floral sales. Additionally, “$2 billion worth of candy and chocolate are sold specifically for Valentine's Day” ([16:00]-[16:16]).
Flower Industry Mechanics: They explore the logistics behind the flower market, particularly the role of Amsterdam’s flower auctions in distributing roses globally, especially in the weeks leading up to February 14th ([15:17]-[16:10]).
Historical Commercial Strategies: Kyle discusses how companies like Cadbury introduced the first heart-shaped box of chocolates in 1860, tying it to Valentine's Day, and how Hollywood films in the late 20th century, such as "You've Got Mail" and "Sleepless in Seattle," amplified the holiday’s romantic image ([12:34]-[13:19]).
Industrial Revolution’s Role: At [17:43], the conversation touches on how the Industrial Revolution enabled the mass production and commercialization of Valentine's Day goods, making the holiday accessible and profitable on a large scale.
These discussions highlight how strategic marketing and industrial advancements have cemented Valentine's Day as a lucrative commercial event.
Psychological and Social Aspects of Valentine's Day
The hosts examine the psychological needs and social dynamics that make Valentine's Day resonate deeply with individuals, particularly focusing on expressions of love and intentionality in relationships.
Emotional Needs: Donald emphasizes that “Valentine’s Day works because there's a need in the human heart, especially a female heart, to be rightly adored” ([30:37]). He contrasts male and female emotional needs, suggesting that women particularly value expressions of adoration and respect.
Intentionality in Relationships: Kyle and Donald discuss the importance of intentional actions in nurturing relationships. At [23:35], Donald states, “The biggest gift you could give... is the actual premeditated attention to honoring them,” advocating for thoughtful gestures over material gifts.
AI’s Role in Enhancing Relationships: The conversation extends to how AI tools, like StoryBrand AI, can assist individuals in articulating their feelings and enhancing communication in relationships. Donald shares a story where AI provided a better response in a delicate situation than he initially planned ([26:07]-[28:28]).
These insights reveal how Valentine's Day serves as a focal point for practicing intentional love and communication, reinforcing relational bonds.
Cultural Reflections and Modern Challenges
Donald and Kyle reflect on the cultural significance of Valentine's Day and the challenges it poses for those who may feel left out or pressured by its commercialization.
Mixed Feelings: Donald acknowledges that while many celebrate the day, there is also "pushback against the sort of Valentine's Day," particularly from individuals who may feel lonely or excluded ([19:07]-[19:24]). He relates this to broader societal expectations and personal circumstances.
Gender Dynamics: The hosts discuss how societal norms influence gender expectations during Valentine's Day, noting that women are often more actively involved in purchasing gifts and organizing celebrations ([14:01]-[14:17]).
Alternative Celebrations: Kyle mentions the rise of alternative celebrations like Galentine’s Day, which caters to different relationship dynamics and offers a broader perspective on expressing love and friendship ([14:04]-[14:13]).
These reflections highlight the complex interplay between cultural traditions, commercialization, and personal experiences surrounding Valentine's Day.
Conclusion and Key Takeaways
In wrapping up the episode, Donald and Kyle summarize the dual factors that make Valentine's Day successful:
Emotional Fulfillment: There is an inherent need for expressions of love and adoration, particularly aligned with societal expectations of relationships and gender roles.
Economic Sustainability: The ability for millions to generate a living through the commercialization of Valentine's Day ensures its persistence and growth as a cultural phenomenon.
Donald concludes, “Valentine’s Day works because there's a need in the human heart, especially a female heart, to be rightly adored,” and “millions of people could make a living off the monetization of this expression on a specific day” ([30:37]-[31:45]).
The hosts encourage listeners to embrace intentionality in their relationships, using Valentine's Day as a catalyst for meaningful expressions of love and appreciation.
Notable Quotes
Donald Miller at [06:00]: “We walked on the sidewalk, and there's nobody there. And I get her down on one knee. She says yes.”
Kyle Reed at [04:25]: “Heather actually helped set it up. And she said yes, and then we flew all of her family in to surprise her.”
Donald Miller at [30:37]: “Valentine’s Day works because there's a need in the human heart, especially a female heart, to be rightly adored.”
Kyle Reed at [23:07]: “You have to give... the gift that involves attention and intentionality.”
Final Thoughts
Episode #6 of "Why That Worked" provides a comprehensive exploration of Valentine's Day, blending personal stories with historical context and economic analysis. Donald Miller and Kyle Reed offer valuable insights into why this holiday remains a significant cultural and commercial force, emphasizing the importance of intentional love and the strategic monetization that sustains its legacy.
Happy Valentine's Day to all listeners!