WEBVTT

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Okay, I want to start this deep dive with a little

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psychological experiment. A word association

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game. Oh, I like this. Okay. I'm going to give

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you a single word, just one, and I want you to

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tell me the very first image, the most visceral,

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immediate picture that pops into your head. Don't

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overthink it, just react. Ready. I am born ready.

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Lay it on me. Oh, okay. Immediately, I see a

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brick. A brown plastic brick. Right. It is instantaneous.

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It's not even a question. You don't think of

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music. You don't think of software or the interface.

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You think of that specific distinctively muddy

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color. It's arguably one of the most memorable

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visuals in consumer electronics history. But

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for all the wrong reasons, it's the punchline.

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It really is. It's the scene in Guardians of

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the Galaxy where Star -Lord gets the Zune. And

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it's treated like this ancient alien artifact

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of failure. It became the cultural shorthand

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for the thing that tried to be an a**hole. iPod

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and lost. Exactly. It's the high profile underdog

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that never had its rocky moment. It's the device

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that you pull out of a drawer 15 years later

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and, you know, you laugh about it. You do. But,

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and this is why we are here today, I think we

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have completely misunderstood the Zune. I think

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the brown brick meme has actually obscured a

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much more interesting and frankly much more tragic

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story. I would agree with that completely. When

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you actually look at the documents, the internal

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strategy memos from Microsoft, the hardware specs,

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the review scores from the time and the postmortems,

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the story isn't. Microsoft made a bad iPod. No,

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not at all. The story is that Microsoft actually

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built the future of music streaming, packaged

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it in a device that was weirdly ahead of its

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time, and then accidentally set it on fire with

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terrible marketing and a few critical glitches.

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And that is our mission for this deep dive. We

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are going to move past the jokes. We're going

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to look at the Zune not as a failure, but as

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a fascinating case study in innovation, timing,

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and corporate hubris. For sure. We have a mountain

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of sources here. Tech reviews from 2006, retrospectives

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on the interface design, financial reports from

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the height of the MP3 wars, and even some deep

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dives into the code that caused it to freeze.

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And we're going to answer a specific question.

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How did a device that cost Microsoft billions

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of dollars end up saving their design soul? Because

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the DNA of the Zune is still running on the computer

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you use today, even if you don't realize it.

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So to understand the end, we have to understand

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the beginning. We need to set the scene. Take

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us back to the landscape of 2006. 2006. It's

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a different world. Twitter is just launching

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and nobody understands it. It's just people texting,

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I'm eating a sandwich to the internet. I remember

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that. Facebook is barely open to the public.

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It's still mostly just for college kids. But

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in the world of digital music, the war is over.

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And Apple won. Apple didn't just win. They salted

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the earth. By the time the Zune is preparing

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to launch in November 2006, the iPod holds a

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63 % market share of portable media players.

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63%. And that number actually understates it

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because in terms of cultural mind share, it was

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probably 99%. It was the Kleenex of MP3 players.

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You didn't say, I'm bringing my MP3 player. You

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said, I'm bringing my iPod. You saw those white

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earbuds everywhere. It was a status symbol. Exactly.

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And Microsoft is sitting there in Redmond. looking

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at this monopoly and they are panicking because

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up until this point, Microsoft had a very specific

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strategy for music and it was failing miserably.

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This was the place for sure era, right? Yes.

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And we have to talk about place for sure because

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it is the crucial context for why the Zune even

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exists. Even the name sounds desperate. Place

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for sure. It's like a car company calling their

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new model the it starts hopefully. It really

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does imply a lack of confidence, doesn't it?

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But the strategy was classic Microsoft. Historically,

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Microsoft is a platform company. They build Windows

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and they let Dell, HP, and Lenovo build the computers.

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The old model. They build the OS, you build the

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box. Exactly. They tried to do the same thing

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with music. So they had a DRM system digital

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rights management called Janus. And they had

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a music store called MSN Music. which launched

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around 2004. The idea was you buy a song from

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MSN, it's wrapped in Microsoft's encryption,

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and then you can put it on any device that has

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the Place for Sure logo. So who was making the

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devices? All the other guys? Everyone who wasn't

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Apple. Creative, Samsung, iRiver, SanDisk. There

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was this army of plastic gray rectangles flooding

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the shelves at Best Buy. I remember having a

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Creative Zen back in the day. It was fine, you

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know. It did the job, but it felt like a piece

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of lab equipment compared to an iPod. How so?

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It had distinct buttons, a weird menu system.

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It felt like a gadget, not an experience. It

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wasn't elegant. That was the problem. The user

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experience was fragmented. You'd buy a song,

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try to sync it to your Samsung device, and maybe

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the drivers were out of date. That's the drivers.

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Or maybe the firmware on the player didn't match

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the DRM version on your computer. It was clunky.

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It did not play for sure. It played, maybe. It

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played eventually if you reinstall the drivers.

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Meanwhile, Apple has the walled garden. They

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make the iPod. They make iTunes. They make the

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Fairplay DRM. It's a closed loop. You plug it

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in. It syncs. You walk away. It's simple. And

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Microsoft, being Microsoft, looks at the numbers

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and realizes, OK, our partners are incompetent.

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If we want to beat Apple, we can't rely on Samsung

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or Creative to design a cool gadget. We have

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to do it ourselves. This is a massive pivot for

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them. This is Microsoft saying, for one of the

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first times, we are going to become a hardware

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company. A consumer hardware company, which they

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had only successfully done once before. The Xbox.

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The Xbox. Right. That context is so important.

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The Xbox launched in 2001. And by 2006, the Xbox

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360 is a massive hit. It proved that Microsoft

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could make hardware that cool people actually

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wanted. That they could capture the living room.

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Exactly. So the executives in Redmond said, get

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us the Xbox guys. Do for music what you did for

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gaming. Enter Jay Allard. Jay Allard is a legend

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in Microsoft history. He was the visionary behind

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the Xbox. He was young. He was bald. He wore

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hoodies. He was the anti -Bill Gates in terms

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of image. He was the cool executive. He was their

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Steve Jobs in a way. In a way, yeah. They put

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him in charge of this new music project, codenamed

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Project Argo. Argo. I like that. It sounds adventurous.

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Like they're sailing into dangerous, dangerous

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waters. It was a serious initiative. They decided

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to kill Plays for Sure. They were going to burn

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their own partners. They told Creative and Samsung,

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sorry, we're competing with you now. Good luck.

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That must have gone over well. Oh, it was a bloodbath

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in the industry relationships. But Microsoft

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felt they had no choice. They needed to control

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the whole stack. The device, the software, the

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store. They were building an ecosystem, not just

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a gadget. They wanted to create an anti -iPod.

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But they didn't build the hardware entirely from

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scratch, did they? Because they were on a really

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tight timeline. I was reading in the notes about

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the Toshiba 1089. Right. So because they were

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in a rush to catch the holiday season of 2006,

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they couldn't engineer a device from the ground

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up in six months. That takes years. Impossible.

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So they partnered with Toshiba. There was an

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existing device called the Toshiba Gigabit S.

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The Gigabit. Another entry in the Hall of Fame

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of terrible MP3 player names. The MP3 era was

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a graveyard of bad names. It really was. But

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the Gigabit S was actually a decent device. Microsoft

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took the guts of the Gigabit, redesigned the

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shell, wrote entirely new software for it, and

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that became the first Zune. So it was a hybrid.

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It was. If you look at the FCC filings from 2006,

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the Zune is literally listed as the Toshiba 1089.

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So effectively, they took a Toshiba body, gave

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it a Microsoft brain, and painted it a very specific

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color. Which brings us to the launch. November

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2006 rolls around. They launched the Zune 30.

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The Zune 30, named for its 30 -gigabyte hard

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drive. A nice, straightforward name, at least.

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Let's talk about this device physically, because

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the specs were actually pretty competitive, weren't

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they? If you strip away the branding and just

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look at the sheet. They were better than competitive.

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In some ways, they were superior to the iPod

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Classic of the time. It had a larger screen,

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3 inches, compared to the iPod's 2 .5. Which

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was a big deal for video. A huge deal. And it

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had an FM radio, which people forget was a huge

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request back then. The iPod never had a radio.

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That was a big differentiator for commuters who

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wanted to listen to morning drive times or NPR.

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Apple always refused to add it because they thought

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it was old tech. Exactly. And the screen was

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landscape oriented, which made it better for

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video. Yeah. But none of that mattered because

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of the design choices. The aesthetic. The aesthetic.

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Microsoft used a manufacturing process called

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double shot injection molding. Basically, you

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have a layer of colored plastic and a layer of

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clear plastic over it. It gives it this depth,

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this premium feel. It sounds nice in theory.

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It is nice. If you hold a Zoom 30 today, it feels

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solid. It doesn't feel cheap. The color is deep

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inside the material. But the color choices, they

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launched with black, white, and brown. Why brown?

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I need to understand this. Who sat in a boardroom

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and said, you know what the kids want? The color

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of dirt. The color of mud. The logic was actually

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rooted. In high fashion, if you can believe it.

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I cannot. They were looking at luxury goods.

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Think about premium leather wallets, expensive

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belts, mahogany furniture, high -end luggage.

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They're trying to evoke a sense of warmth and

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organic texture. To contrast with Apple's sterile

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white. Precisely. They wanted it to feel like

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a crafted object. Apple is cold, clinical, sci

00:09:33.169 --> 00:09:37.850
-fi. We are warm, human, organic. But the execution

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didn't read as luxury leather. No. It read as...

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Well, poop. A turd. A brick of chocolate left

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in the sun. It was immediately mocked. The tech

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blogs, which were just gaining power at this

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time, sites like Engadget and Gizmodo, they tore

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it apart. They called it the brick. It looked

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clunky. It had hard angles. And that first impression

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matters so much. You're launching against the

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coolest product on the planet. You can't just

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be good. You have to be desirable. And brown

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is rarely the color of desire in consumer electronics.

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It's true. Even today, how many brown phones

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do you see? It's a risky color. And for a company

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like Microsoft, which was already seen as the

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uncool office productivity company, trying to

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pull off high fashion brown was a stretch. You

00:10:20.419 --> 00:10:22.139
just reinforce the idea that they didn't get

00:10:22.139 --> 00:10:24.539
it. But putting the color aside, the hardware

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didn't stay a brick forever. I feel like the

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Zoom 30 is the only one people remember because

00:10:29.620 --> 00:10:32.000
of the memes. But the evolution happened really

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fast. It did. The second generation arrived just

00:10:34.960 --> 00:10:38.049
a year later in 2007. Yeah. And this is where

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the hardware actually got really good. They introduced

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the Zune pad. This is the squircle. The squircle.

00:10:43.409 --> 00:10:47.149
A rounded square is a stroke of genius. Apple

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had the patent on the click wheel, which was,

00:10:49.570 --> 00:10:52.049
let's be honest, the greatest navigation tool

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ever invented for music. It was so satisfying,

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that circular scrolling motion. Microsoft couldn't

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use a wheel, so they made a touch -sensitive

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pad. You could flick your thumb up and down to

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scroll, like you do on a smartphone screen today.

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But you could also click the buttons physically.

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It was a hybrid. That's actually a really difficult

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engineering challenge, to mix capacitive touch

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with physical tactile feedback. It was. And it

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worked beautifully. It was fast. You could fly

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through lists of songs. They also expanded the

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line. They realized that hard drive players were

00:11:21.779 --> 00:11:24.139
heavy, so they launched the Zune 4 and Zune 8.

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A flash memory players? Right. Tiny credit card

00:11:27.559 --> 00:11:29.980
size to fight the iPod Nano. Yeah. And then...

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Bigger hard drive ones, the 80 and the 120. And

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this is where they started doing the customization

00:11:33.889 --> 00:11:37.429
stuff, right? Zune Originals. This was a great

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idea. You could go to their website and order

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a Zune with custom artwork laser edged onto the

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back. I remember seeing those. They hired legit

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artists to do these designs. Psychedelic patterns,

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abstract art tattoos. You could pick crazy color

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combinations. Which is something Apple never

00:11:54.370 --> 00:11:57.100
really did. Apple was very... You will take the

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white one or maybe the black one and you will

00:11:59.259 --> 00:12:02.440
like it. Apple was uniform. Zune was trying to

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be expressive. Music is personal. Your players

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should be too. It was a smart angle. It gave

00:12:08.100 --> 00:12:10.159
them a personality that wasn't just we are the

00:12:10.159 --> 00:12:12.379
other guys. But if we are talking about the hardware

00:12:12.379 --> 00:12:15.360
peak, the absolute Mona Lisa of the Zune lineup,

00:12:15.480 --> 00:12:19.500
we have to jump to 2009. The Zune HD. The Zune

00:12:19.500 --> 00:12:21.399
HD. It breaks my heart a little just talking

00:12:21.399 --> 00:12:24.490
about it. Why? Because it is a genuinely magnificent

00:12:24.490 --> 00:12:26.750
piece of machinery that nobody bought. It's like

00:12:26.750 --> 00:12:28.750
a great album that never charted. Paint the picture

00:12:28.750 --> 00:12:31.710
for us. 2009. What was this thing? Imagine a

00:12:31.710 --> 00:12:35.629
slab of glass and aluminum. Screws exposed. Industrial

00:12:35.629 --> 00:12:38.690
chic. It was smaller than an iPod Touch. And

00:12:38.690 --> 00:12:42.669
the screen... It was an OLED. Explain why OLED

00:12:42.669 --> 00:12:45.309
matters here. Because in 2009, most screens were

00:12:45.309 --> 00:12:47.549
LCD, right? Everything was LCD. Yeah. Well, the

00:12:47.549 --> 00:12:49.830
T -screens have a backlight. Even when the screen

00:12:49.830 --> 00:12:51.950
is showing black, the light is on, so it's actually

00:12:51.950 --> 00:12:55.450
a dark gray. OLED organic light emitting diode

00:12:55.450 --> 00:12:57.730
emits its own light. Each pixel makes its own

00:12:57.730 --> 00:12:59.710
light. Exactly. So when a pixel is black, it

00:12:59.710 --> 00:13:03.529
is off. It is perfectly inky black. So the contrast

00:13:03.529 --> 00:13:06.230
is infinite. The colors popped in a way that

00:13:06.230 --> 00:13:08.919
nothing else on the market did. The iPhone didn't

00:13:08.919 --> 00:13:11.059
get an OLED screen until the iPhone X, nearly

00:13:11.059 --> 00:13:14.019
a decade later. A full decade. The Zune HD had

00:13:14.019 --> 00:13:16.600
it in 2009. That is wild. They were 10 years

00:13:16.600 --> 00:13:19.740
ahead on the screen tech. Inside, it had an NVIDIA

00:13:19.740 --> 00:13:22.419
Tegra chip. This was a powerhouse processor usually

00:13:22.419 --> 00:13:25.399
used for much bigger devices. It could play 720p

00:13:25.399 --> 00:13:28.700
HD video out to a TV via a dock. It had an HD

00:13:28.700 --> 00:13:30.919
radio receiver built in. It was arguably the

00:13:30.919 --> 00:13:32.639
most advanced portable media player ever made.

00:13:32.779 --> 00:13:34.620
And the reviews back this up. This wasn't just

00:13:34.620 --> 00:13:37.990
Microsoft hype. Overwhelmingly. Farhad Manjoo,

00:13:38.129 --> 00:13:41.009
who is not an easy critic to please, wrote in

00:13:41.009 --> 00:13:44.610
Slate that if you bought a Zune HD over an iPod

00:13:44.610 --> 00:13:46.230
Touch, you wouldn't have regretted it. That's

00:13:46.230 --> 00:13:49.230
high praise. TechRadar, CNET, they all praised

00:13:49.230 --> 00:13:51.470
the hardware. They said it felt better in the

00:13:51.470 --> 00:13:54.370
hand than the iPod. The build quality was exceptional.

00:13:54.950 --> 00:13:57.529
So we have a device that is objectively great.

00:13:57.669 --> 00:14:00.389
Superior screen, great build quality, snappy

00:14:00.389 --> 00:14:03.779
performance. Why didn't it work? Why didn't everyone

00:14:03.779 --> 00:14:06.039
throw away their iPods? Well, that leads us to

00:14:06.039 --> 00:14:08.080
the philosophy. You can have the best hardware

00:14:08.080 --> 00:14:10.299
in the world, but if your story doesn't resonate,

00:14:10.480 --> 00:14:12.899
you're dead. And Microsoft was trying to tell

00:14:12.899 --> 00:14:15.620
a very specific story with the Zoom. Welcome

00:14:15.620 --> 00:14:18.039
to the social. That was the tagline. Which, again,

00:14:18.080 --> 00:14:19.840
feels like a misread of the room. When I think

00:14:19.840 --> 00:14:22.240
of MP3 players, especially back then, I think

00:14:22.240 --> 00:14:24.720
of headphones on, world off. I'm on the subway.

00:14:24.779 --> 00:14:26.620
I don't want to talk to people. You want to be

00:14:26.620 --> 00:14:29.159
in your own bubble. Right. That was Apple's marketing

00:14:29.159 --> 00:14:32.860
genius. The silhouette adds. A person dancing

00:14:32.860 --> 00:14:36.179
alone against a bright background. Pure individualism.

00:14:36.399 --> 00:14:39.399
You are the star of your own music video. A private

00:14:39.399 --> 00:14:42.240
concert. Microsoft tried to zig where Apple zagged.

00:14:42.240 --> 00:14:44.940
They said, no, music is a communal experience.

00:14:45.440 --> 00:14:48.740
Music is how we bond. Music is for sharing. And

00:14:48.740 --> 00:14:51.860
they built a feature to force this bonding. The

00:14:51.860 --> 00:14:55.379
infamous Wi -Fi sharing. Codenamed. And I'm sorry

00:14:55.379 --> 00:14:58.120
I have to say this. Squirt. Grown, stop. Let

00:14:58.120 --> 00:15:00.919
me squirt you this song. Who approved that? Was

00:15:00.919 --> 00:15:03.259
there no adult in the room? It was an internal

00:15:03.259 --> 00:15:05.879
engineering term, like squirting data across

00:15:05.879 --> 00:15:08.559
a wire, that somehow leaked out into the public

00:15:08.559 --> 00:15:10.620
consciousness, though they officially called

00:15:10.620 --> 00:15:13.620
it Zune -to -Zune sharing. Thank goodness. But

00:15:13.620 --> 00:15:15.639
the concept was actually revolutionary. How did

00:15:15.639 --> 00:15:18.840
it work? The Zune had Wi -Fi. The iPod didn't.

00:15:19.000 --> 00:15:21.299
If you and I were standing at a bus stop and

00:15:21.299 --> 00:15:23.700
I was listening to a great new track, I could

00:15:23.700 --> 00:15:26.639
press a button. Find your Zune wirelessly and

00:15:26.639 --> 00:15:28.559
beam the song to you. That sounds like magic.

00:15:28.940 --> 00:15:30.759
Today we have AirDrop, but that's mostly for

00:15:30.759 --> 00:15:33.100
photos or links. Sharing a song file instantly.

00:15:33.259 --> 00:15:36.000
That's the dream. It is the dream. Imagine discovering

00:15:36.000 --> 00:15:38.379
a band and spreading it virally through a crowd

00:15:38.379 --> 00:15:41.580
at a festival. But then, the lawyers got involved.

00:15:41.759 --> 00:15:44.559
Record labels? Of course. The record labels were

00:15:44.559 --> 00:15:47.220
terrified. They looked at this feature and saw

00:15:47.220 --> 00:15:50.799
Napster in a pocket. They thought if people can

00:15:50.799 --> 00:15:53.120
share songs, nobody will ever buy them again.

00:15:53.259 --> 00:15:55.740
So they forced Microsoft to cripple the feature.

00:15:56.639 --> 00:15:59.419
This is the three plays rule. Three plays or

00:15:59.419 --> 00:16:01.960
three days. If I sent you a song, you couldn't

00:16:01.960 --> 00:16:04.179
keep it. You would sit in your inbox. You could

00:16:04.179 --> 00:16:06.240
listen to it three times or keep it for three

00:16:06.240 --> 00:16:10.279
days, whichever came first. After that, poof.

00:16:11.269 --> 00:16:14.590
Gone. That is so frustrating. It takes a magical

00:16:14.590 --> 00:16:16.950
moment. Here's a gift. I love this song and turns

00:16:16.950 --> 00:16:19.250
it into a chore. Hurry up and listen to this

00:16:19.250 --> 00:16:21.710
before it explodes. It destroyed the value proposition.

00:16:21.970 --> 00:16:24.350
It felt stingy. It felt like a trial version,

00:16:24.590 --> 00:16:26.850
not a social connection. And here's the other

00:16:26.850 --> 00:16:29.669
problem. Network effects. Right. For Zoom to

00:16:29.669 --> 00:16:32.049
Zoom sharing to work, you need another person

00:16:32.049 --> 00:16:34.129
with a Zoom. Exactly. And because Zoom market

00:16:34.129 --> 00:16:36.730
share was so low. the odds of you actually meeting

00:16:36.730 --> 00:16:39.230
another person with a Zune in the wild were statistically

00:16:39.230 --> 00:16:41.570
insignificant. So you had this social feature

00:16:41.570 --> 00:16:43.470
that you could never use because you were the

00:16:43.470 --> 00:16:45.370
only guy at the party with the brown brick. It

00:16:45.370 --> 00:16:47.629
was a lonely social network. Ideally, they should

00:16:47.629 --> 00:16:50.190
have fought the labels harder. But I guess in

00:16:50.190 --> 00:16:53.830
2006, the labels still held all the cards. Streaming

00:16:53.830 --> 00:16:56.330
hadn't broken their power yet. They did. But

00:16:56.330 --> 00:16:57.970
there was another part of the service that Microsoft

00:16:57.970 --> 00:17:00.850
got right. And this is the part that really hurts

00:17:00.850 --> 00:17:03.450
to look back on. The Zune Pass. The Zune Pass.

00:17:03.830 --> 00:17:06.170
Okay, let's unpack this. Because when I read

00:17:06.170 --> 00:17:08.710
about this, I realized I'm basically paying for

00:17:08.710 --> 00:17:11.109
Zune Pass today, just under a different name.

00:17:11.269 --> 00:17:14.849
You are. We all are. In 2006, the dominant model

00:17:14.849 --> 00:17:18.750
was iTunes. You pay 99 cents. You get one song.

00:17:18.829 --> 00:17:21.470
It's a digital record store a la carte. You own

00:17:21.470 --> 00:17:23.650
the file. Ownership was king. That was the whole

00:17:23.650 --> 00:17:25.869
idea. Ownership was king. Microsoft looked at

00:17:25.869 --> 00:17:29.430
the future and said, subscription. For $14 .99

00:17:29.430 --> 00:17:32.289
a month, you got the Zune Pass. Unlimited downloads.

00:17:32.430 --> 00:17:34.170
You could download the entire catalog if you

00:17:34.170 --> 00:17:37.269
had the hard drive space. So it was Spotify before

00:17:37.269 --> 00:17:40.529
Spotify. It was Spotify, but downloadable. You

00:17:40.529 --> 00:17:42.650
didn't need a constant internet connection. You

00:17:42.650 --> 00:17:44.730
synced the songs, and as long as you kept paying

00:17:44.730 --> 00:17:47.690
the monthly fee, they worked. But $15 a month

00:17:47.690 --> 00:17:50.190
felt expensive back then. People were used to

00:17:50.190 --> 00:17:53.339
buying one album a month for $10. It did. which

00:17:53.339 --> 00:17:56.240
is why Microsoft added the Keep incentive. This

00:17:56.240 --> 00:17:58.880
was the best deal in the history of digital music,

00:17:58.980 --> 00:18:01.559
bar none. I still can't believe they offered

00:18:01.559 --> 00:18:05.000
this. The 10 tracks rule. Yes. Every month, on

00:18:05.000 --> 00:18:06.980
top of the unlimited listening, you could pick

00:18:06.980 --> 00:18:10.259
10 songs to download and keep forever, DRM -free.

00:18:10.339 --> 00:18:13.000
Even if you cancel the subscription, those 10

00:18:13.000 --> 00:18:16.329
songs were yours. So let's do the math. 10 songs

00:18:16.329 --> 00:18:19.910
on iTunes costs $10. The subscription is $15.

00:18:19.930 --> 00:18:22.890
So you are basically paying $5 a month for unlimited

00:18:22.890 --> 00:18:25.269
access to all the music in the world. Correct.

00:18:25.450 --> 00:18:27.430
It was practically free streaming. It was an

00:18:27.430 --> 00:18:30.750
incredible value. But consumers just couldn't

00:18:30.750 --> 00:18:32.289
wrap their heads around it. We weren't ready.

00:18:32.509 --> 00:18:34.430
We weren't ready to stop owning our music. People

00:18:34.430 --> 00:18:37.250
looked at the $15 fee and said, but I don't own

00:18:37.250 --> 00:18:39.690
anything at the end of the month. The concept

00:18:39.690 --> 00:18:41.950
of access over ownership hadn't clicked yet.

00:18:42.049 --> 00:18:44.869
It's the curse of being too early. You look wrong,

00:18:45.009 --> 00:18:47.970
even if you're right. And Microsoft was terrible

00:18:47.970 --> 00:18:50.690
at explaining it. Their ads were weird and abstract.

00:18:50.990 --> 00:18:52.670
They should have just put up a billboard that

00:18:52.670 --> 00:18:56.269
said Spotify for $5. But Spotify didn't exist,

00:18:56.349 --> 00:18:58.210
so they couldn't make the comparison. They were

00:18:58.210 --> 00:19:00.309
describing a color to people who had only ever

00:19:00.309 --> 00:19:02.789
seen black and white. Perfectly put. So they

00:19:02.789 --> 00:19:04.890
have the tech Wi -Fi sharing. They have the business

00:19:04.890 --> 00:19:07.849
model subscriptions. But they can't sell it.

00:19:08.130 --> 00:19:12.170
And then the glitches start. We can't do a deep

00:19:12.170 --> 00:19:14.130
dive on the Zune without talking about the Great

00:19:14.130 --> 00:19:17.130
Leap Year meltdown. The Zune 30 freeze, New Year's

00:19:17.130 --> 00:19:20.069
Eve 2008. The story is incredible. It's like

00:19:20.069 --> 00:19:22.609
Y2K, but it actually happened, and only to people

00:19:22.609 --> 00:19:25.410
with brown bricks. It's at the scene. It's December

00:19:25.410 --> 00:19:28.250
31st, 2008. People are getting ready for parties.

00:19:28.490 --> 00:19:30.589
They plug in their Zunes to load up a playlist

00:19:30.589 --> 00:19:33.750
for the night, and the screen freezes. Just freezes.

00:19:33.930 --> 00:19:36.130
It gets stuck on the loading bar. You reset it,

00:19:36.150 --> 00:19:38.430
it freezes again. You hard reboot, it freezes

00:19:38.430 --> 00:19:40.890
again. And it's not just a few people. It is

00:19:40.890 --> 00:19:44.990
every single first -generation Zune 30 on the

00:19:44.990 --> 00:19:47.930
planet simultaneously. That must have been terrifying.

00:19:47.930 --> 00:19:50.549
Did people think it was a virus? A kill switch?

00:19:50.890 --> 00:19:54.109
The forums were on fire. People thought Microsoft

00:19:54.109 --> 00:19:56.109
had bricked the devices remotely to force them

00:19:56.109 --> 00:19:59.529
to buy the new Zune. Panic. Conspiracy theories.

00:19:59.789 --> 00:20:02.869
But the reality was much, much dumber. It was

00:20:02.869 --> 00:20:05.670
a driver bug. Specifically, the internal clock

00:20:05.670 --> 00:20:08.069
driver. It was a piece of code written by a component

00:20:08.069 --> 00:20:10.960
supplier called Freescale. The code's job was

00:20:10.960 --> 00:20:13.119
to calculate what day of the year it was. In

00:20:13.119 --> 00:20:17.500
2008 was a leap year, 366 days. Exactly. The

00:20:17.500 --> 00:20:20.119
code had a logic loop. It said essentially, if

00:20:20.119 --> 00:20:23.559
days is greater than 365, subtract 365 and add

00:20:23.559 --> 00:20:26.559
one to the year. But the way it was written on

00:20:26.559 --> 00:20:30.670
the 366th day. It entered an infinite loop. Oh,

00:20:30.670 --> 00:20:33.490
no. It kept asking, is it day 366? And the answer

00:20:33.490 --> 00:20:36.069
was yes. So it just spun in circles, burning

00:20:36.069 --> 00:20:38.150
the processor. The device wasn't broken. It was

00:20:38.150 --> 00:20:40.049
just thinking really, really hard about what

00:20:40.049 --> 00:20:42.049
day it was. It was an existential crisis for

00:20:42.049 --> 00:20:45.029
the microchip. What day is it? It can't be today.

00:20:45.130 --> 00:20:47.309
Try again. What day is it? So what was the fix?

00:20:47.430 --> 00:20:49.650
Did they have to issue a patch? They couldn't

00:20:49.650 --> 00:20:51.849
patch it because the devices wouldn't boot. Microsoft

00:20:51.849 --> 00:20:54.049
engineers scrambled, found the bug in the source

00:20:54.049 --> 00:20:57.069
code, and then realized the solution was... to

00:20:57.069 --> 00:20:59.549
do nothing. Microsoft's official advice was,

00:20:59.670 --> 00:21:02.190
wait. You had to let the battery drain completely

00:21:02.190 --> 00:21:05.269
so the internal clock would stop. Then, wait

00:21:05.269 --> 00:21:09.049
until noon GMT on January 1st, 2009. Why noon?

00:21:09.630 --> 00:21:11.250
So that the entire world was safely into the

00:21:11.250 --> 00:21:13.710
new day. Once the calendar rolled over naturally

00:21:13.710 --> 00:21:16.210
to a non -leap year day, the math worked again.

00:21:16.369 --> 00:21:18.650
You recharged it, turned it on, and it was fine.

00:21:18.910 --> 00:21:21.990
That is humiliating. It was the final nail in

00:21:21.990 --> 00:21:24.569
the coffin for the brand's reputation. Here's

00:21:24.569 --> 00:21:26.789
this device that is already the butt of jokes,

00:21:26.950 --> 00:21:29.069
and now it can't even tell time on New Year's

00:21:29.069 --> 00:21:31.190
Eve. It just reinforced the narrative. Apple

00:21:31.190 --> 00:21:34.849
is polish, Microsoft is buggy, Apple works, Zoom

00:21:34.849 --> 00:21:37.529
crashes. It became a joke on late night TV. The

00:21:37.529 --> 00:21:40.009
Zoom is hungover. And the marketing didn't help.

00:21:40.069 --> 00:21:42.250
I remember seeing a website called ComingZoon.

00:21:42.250 --> 00:21:45.829
Oh, God. ComingZoon. Spelled C -O -M -I -N -G

00:21:45.829 --> 00:21:49.599
-Z -U -N -E. Yeah. It was this weird, artsy,

00:21:49.599 --> 00:21:51.759
viral marketing campaign. They tried to create

00:21:51.759 --> 00:21:54.200
a grassroots movement. They hired Zoonmasters.

00:21:54.559 --> 00:21:56.500
Zoonmasters? What is a Zoonmaster? College campus

00:21:56.500 --> 00:21:58.880
reps. They would walk around with Zoons, trying

00:21:58.880 --> 00:22:01.339
to act cool, handing out stickers, hosting parties.

00:22:01.460 --> 00:22:04.019
But it felt so forced. It felt like a corporation

00:22:04.019 --> 00:22:06.940
wearing a backwards baseball cap saying, how

00:22:06.940 --> 00:22:09.220
do you do, fellow kids? Authentic cool cannot

00:22:09.220 --> 00:22:12.420
be manufactured. You can't buy cool with a marketing

00:22:12.420 --> 00:22:15.789
budget. And the retailers smelled blood. By 2008,

00:22:16.329 --> 00:22:18.269
GameStop announced they were pulling Zunes from

00:22:18.269 --> 00:22:21.009
their shelves. That's a bad sign. When the video

00:22:21.009 --> 00:22:23.309
game store, which is arguably your core demographic,

00:22:23.730 --> 00:22:26.809
Xbox Gamers, says, we don't want this, you are

00:22:26.809 --> 00:22:29.069
in trouble. They cited insufficient demand. The

00:22:29.069 --> 00:22:30.890
numbers were brutal. Give us the scorecard. How

00:22:30.890 --> 00:22:33.950
bad did it get? Launch week in 2006, they managed

00:22:33.950 --> 00:22:38.009
a 9 % unit share. Not terrible, but mostly powered

00:22:38.009 --> 00:22:40.609
by initial curiosity and Microsoft loyalists.

00:22:40.769 --> 00:22:43.440
Okay, a toehold. A toehold. But it never grew.

00:22:43.559 --> 00:22:46.240
At its absolute peak, they maybe hit 10 or 11

00:22:46.240 --> 00:22:48.380
percent of the hard drive player market. But

00:22:48.380 --> 00:22:51.859
then the slide began. By 2009, the year of the

00:22:51.859 --> 00:22:54.380
magnificent Zune HD market share in the U .S.

00:22:54.400 --> 00:22:57.240
had fallen to 2 percent. 2 percent. That is a

00:22:57.240 --> 00:23:01.140
rounding error. Meanwhile, Apple held 73 percent.

00:23:02.400 --> 00:23:05.079
SanDisk, the budget option, was beating Microsoft.

00:23:05.700 --> 00:23:09.259
Creative was beating them. In early 2009, Microsoft

00:23:09.259 --> 00:23:13.160
reported a $100 million drop in sales revenue

00:23:13.160 --> 00:23:15.980
from the previous year. It was a money pit. But

00:23:15.980 --> 00:23:18.299
we have to zoom out here. Because even if the

00:23:18.299 --> 00:23:20.640
Zoom was perfect, even if it was gold -plated

00:23:20.640 --> 00:23:23.079
and made you coffee, it was doomed, wasn't it?

00:23:23.140 --> 00:23:26.099
This is the tragedy. Microsoft was fighting a

00:23:26.099 --> 00:23:28.640
war for a territory that was sinking into the

00:23:28.640 --> 00:23:32.200
ocean. The smartphone. January 2007. Just two

00:23:32.200 --> 00:23:34.720
months after the Zoom launches, Steve Jobs walks

00:23:34.720 --> 00:23:37.779
on stage and introduces the iPhone. He calls

00:23:37.779 --> 00:23:40.940
it a widescreen iPod with touch controls, a revolutionary

00:23:40.940 --> 00:23:43.740
mobile phone, and a breakthrough internet communicator.

00:23:43.859 --> 00:23:46.279
The widescreen iPod part is the key. The moment

00:23:46.279 --> 00:23:48.579
the iPhone existed, the standalone MP3 player

00:23:48.579 --> 00:23:51.420
was deadwalking. Why carry a phone in a Zoom

00:23:51.420 --> 00:23:53.920
when your phone is an iPod? So Zoom was fighting

00:23:53.920 --> 00:23:56.319
for the scraps of a dying industry. Microsoft

00:23:56.319 --> 00:23:58.680
was obsessing over how to beat the iPod classic,

00:23:58.839 --> 00:24:01.279
while Apple was busy making the iPod irrelevant.

00:24:01.920 --> 00:24:04.039
It's a classic case of what Simon Sinek calls

00:24:04.039 --> 00:24:07.009
the infinite game. Explain that concept. Cynic

00:24:07.009 --> 00:24:09.450
argues that there are finite games and infinite

00:24:09.450 --> 00:24:13.609
games. A finite game has rules, a beginning and

00:24:13.609 --> 00:24:17.670
an end. The goal is to win. Football is a finite

00:24:17.670 --> 00:24:20.569
game. Microsoft was playing a finite game. Beat

00:24:20.569 --> 00:24:22.849
the iPod. Right. They looked at Apple specs and

00:24:22.849 --> 00:24:25.170
tried to top them. They have 30 jibby. We have

00:24:25.170 --> 00:24:27.410
30 jibby. They have a screen. Ours is bigger.

00:24:27.529 --> 00:24:29.430
But Apple was playing the infinite game. Right.

00:24:29.509 --> 00:24:32.200
The infinite game has no finish line. The goal

00:24:32.200 --> 00:24:34.940
is to stay in the game and evolve. Apple wasn't

00:24:34.940 --> 00:24:37.640
trying to beat Microsoft's MP3 player. They were

00:24:37.640 --> 00:24:40.240
trying to reinvent how humans interact with information.

00:24:40.579 --> 00:24:42.759
They cannibalized their own product. They cannibalized

00:24:42.759 --> 00:24:45.920
their own golden goose, the iPod, to create the

00:24:45.920 --> 00:24:48.240
iPhone. Microsoft wasn't willing to do that yet.

00:24:48.359 --> 00:24:50.680
They were protecting the Zune while Apple was

00:24:50.680 --> 00:24:53.339
killing the iPod to birth the iPhone. Exactly.

00:24:53.680 --> 00:24:56.359
Sinek calls the Zune a triumph of design but

00:24:56.359 --> 00:24:59.359
a failure of strategic thinking. They built the

00:24:59.359 --> 00:25:02.099
best buggy whip right as the Model T rolled off

00:25:02.099 --> 00:25:04.559
the assembly line. So the end comes. When did

00:25:04.559 --> 00:25:07.019
they finally pull the plug? It was a slow, painful

00:25:07.019 --> 00:25:10.660
fade. March 2011, they announced no new hardware

00:25:10.660 --> 00:25:13.500
would be developed. October 2011, officially.

00:25:14.480 --> 00:25:18.019
And finally in 2015, the Zune music service was

00:25:18.019 --> 00:25:21.059
shut down and users were migrated to Groove Music.

00:25:21.279 --> 00:25:23.299
Which nobody used either. Which was also eventually

00:25:23.299 --> 00:25:26.839
killed. RIP Zune. But wait, we can't end on the

00:25:26.839 --> 00:25:29.220
RIP. Because this is where the story gets really

00:25:29.220 --> 00:25:32.000
interesting. This is the legacy part of our deep

00:25:32.000 --> 00:25:34.779
dive. The slate theory. The flop that saved Microsoft.

00:25:35.099 --> 00:25:37.359
It sounds counterintuitive, doesn't it? How does

00:25:37.359 --> 00:25:39.460
a financial disaster save a company? You have

00:25:39.460 --> 00:25:42.119
to look at what Windows was in 2006. Windows

00:25:42.119 --> 00:25:45.980
XP. Windows Vista. It was gray. It was cluttered.

00:25:45.980 --> 00:25:48.000
It was a spreadsheet. It was designed by engineers

00:25:48.000 --> 00:25:51.400
for engineers. Bevels, shadows, drop -down menus,

00:25:51.599 --> 00:25:53.940
inside drop -down menus. There was no joy in

00:25:53.940 --> 00:25:56.039
it. It was work. Then look at the Zune HD interface.

00:25:56.240 --> 00:25:58.880
It didn't use icons. It used typography. Big,

00:25:58.880 --> 00:26:02.960
bold words. Music, videos, social. The words

00:26:02.960 --> 00:26:04.599
were the navigation. You swiped through them.

00:26:04.660 --> 00:26:06.359
It was fluid. It was animated. It felt alive.

00:26:06.660 --> 00:26:08.779
The content was the hero. This was the birth

00:26:08.779 --> 00:26:12.279
of the Metro design language. Yes. They used

00:26:12.279 --> 00:26:14.799
a font called Segoe, which Microsoft still uses

00:26:14.799 --> 00:26:18.240
today. They prioritized content over Chrome,

00:26:18.440 --> 00:26:20.880
meaning the borders and buttons. They realized

00:26:20.880 --> 00:26:23.019
that the interface should recede and the content

00:26:23.019 --> 00:26:24.720
should come forward. And they took this little

00:26:24.720 --> 00:26:26.960
design experiment from the failed music player

00:26:26.960 --> 00:26:29.319
and they injected it into the main bloodstream

00:26:29.319 --> 00:26:32.519
of Microsoft. It became the interface for Windows

00:26:32.519 --> 00:26:35.380
Phone 7. It became the dashboard for the Xbox

00:26:35.380 --> 00:26:38.630
360. And eventually it evolved into the tile

00:26:38.630 --> 00:26:41.289
interface of Windows 8. The live tiles. Even

00:26:41.289 --> 00:26:43.170
today, if you open the start menu in Windows

00:26:43.170 --> 00:26:46.529
10 or 11, that clean, flat design, the reliance

00:26:46.529 --> 00:26:49.309
on typography, the lack of fake 3D effects, that

00:26:49.309 --> 00:26:51.690
can all trace its lineage directly back to the

00:26:51.690 --> 00:26:54.910
Zoom team. So in a way, the Zoom died so that

00:26:54.910 --> 00:26:57.289
Microsoft could learn how to design. It taught

00:26:57.289 --> 00:26:59.750
them that user experience matters, that you can't

00:26:59.750 --> 00:27:02.069
just throw features at a user. You have to curate

00:27:02.069 --> 00:27:04.730
an experience. Before Zoom, Microsoft was an

00:27:04.730 --> 00:27:06.930
engineering company. Zune forced them to become

00:27:06.930 --> 00:27:08.609
a design company, at least in their consumer

00:27:08.609 --> 00:27:11.109
products. It humanized them. There's also this

00:27:11.109 --> 00:27:13.250
funny little lingering ghost of the Zune that

00:27:13.250 --> 00:27:16.630
I absolutely love. It involves airplanes. United

00:27:16.630 --> 00:27:19.849
Airlines. This is a great trivia nugget. Tell

00:27:19.849 --> 00:27:22.250
the listeners about this, because this proves

00:27:22.250 --> 00:27:25.309
the brand had a weirdly long half -life. So,

00:27:25.349 --> 00:27:27.529
United Airlines had a partnership with Microsoft

00:27:27.529 --> 00:27:31.049
to provide the audio for their Inflate Entertainment

00:27:31.049 --> 00:27:33.710
systems. You know, the little jack in the armrest

00:27:33.710 --> 00:27:35.509
where you plug in the plastic headphones? The

00:27:35.509 --> 00:27:37.670
one that always sounds staticky and plays a loop

00:27:37.670 --> 00:27:41.630
of classical music. That's the one. Well, long

00:27:41.630 --> 00:27:44.289
after the Zune hardware was discontinued, United

00:27:44.289 --> 00:27:48.079
kept using the branding. So in 2010, 2011, even

00:27:48.079 --> 00:27:50.740
2012, if you were flying to Denver or Chicago,

00:27:51.119 --> 00:27:54.039
you were listening to Zune contemporary pop or

00:27:54.039 --> 00:27:57.420
Zune piano jazz. That is fantastic. A zombie

00:27:57.420 --> 00:28:00.180
brand cruising at 30 ,000 feet. While the devices

00:28:00.180 --> 00:28:02.559
were gathering dust in pawn shops, the brand

00:28:02.559 --> 00:28:04.900
was flying high. It just shows how deep the corporate

00:28:04.900 --> 00:28:07.160
deals went. And the software lived on, too, right?

00:28:07.279 --> 00:28:09.859
The Zune desktop software, which, frankly, was

00:28:09.859 --> 00:28:12.500
much better than iTunes on Windows, became the

00:28:12.500 --> 00:28:15.420
sync tool for Windows Phone. If you bought an

00:28:15.420 --> 00:28:17.319
early Windows phone, you had to use Zune software

00:28:17.319 --> 00:28:20.359
to manage it. I remember that. So for a few years,

00:28:20.500 --> 00:28:23.259
Zune was the gateway to Microsoft's mobile strategy.

00:28:23.559 --> 00:28:25.359
So it really was the bridge. It was the bridge

00:28:25.359 --> 00:28:28.680
from old Microsoft to modern Microsoft. It was

00:28:28.680 --> 00:28:30.640
the necessary failure. Sometimes you have to

00:28:30.640 --> 00:28:33.240
fall on your face to learn how to run. Jay Allard

00:28:33.240 --> 00:28:35.980
and his team taught Microsoft that they could

00:28:35.980 --> 00:28:38.220
make something beautiful, even if they couldn't

00:28:38.220 --> 00:28:40.859
sell it. So as we wrap this up, I want to pose

00:28:40.859 --> 00:28:43.410
a what -if scenario. Because we talked about

00:28:43.410 --> 00:28:46.589
the Zune Pass, the subscription model. Microsoft

00:28:46.589 --> 00:28:49.069
had the rights. They had the catalog. They had

00:28:49.069 --> 00:28:51.309
the streaming tech. They had it all. But they

00:28:51.309 --> 00:28:53.750
locked it to the Zune hardware. You had to buy

00:28:53.750 --> 00:28:55.809
the brown brick to get the service. Correct.

00:28:55.890 --> 00:28:59.009
That was their fatal error. Imagine if in 2008

00:28:59.009 --> 00:29:02.470
or 2009, Microsoft had said, you know what? We

00:29:02.470 --> 00:29:03.970
aren't going to beat the iPhone with hardware.

00:29:04.130 --> 00:29:07.109
Let's put the Zune Pass app on the iPhone. That

00:29:07.109 --> 00:29:09.309
is the multi -billion dollar question. If they

00:29:09.309 --> 00:29:11.829
had launched a cross -platform music subscription

00:29:11.829 --> 00:29:15.009
service four years before Spotify launched in

00:29:15.009 --> 00:29:17.809
the U .S., would we be using Zune instead of

00:29:17.809 --> 00:29:20.069
Spotify today? It is very, very possible. They

00:29:20.069 --> 00:29:21.670
had the infrastructure. They had the Head Start.

00:29:21.849 --> 00:29:24.869
They had the artist relationships. But they were

00:29:24.869 --> 00:29:27.230
blinded by the hardware envy. They wanted a cool

00:29:27.230 --> 00:29:30.069
gadget. They wanted to be Apple so bad that they

00:29:30.069 --> 00:29:32.430
forgot they were Microsoft, a software company.

00:29:32.509 --> 00:29:35.150
They missed the forest for the trees. Or the

00:29:35.150 --> 00:29:38.930
cloud for the brick. They insisted on selling

00:29:38.930 --> 00:29:40.789
the box when they should have been selling the

00:29:40.789 --> 00:29:43.250
service. If they had pivoted to services just

00:29:43.250 --> 00:29:46.269
a few years earlier, Zune could be the biggest

00:29:46.269 --> 00:29:48.569
music platform in the world right now. And that,

00:29:48.569 --> 00:29:51.650
my friends, is the tragedy of the Zune. A brilliant

00:29:51.650 --> 00:29:55.410
service trapped inside a misunderstood... occasionally

00:29:55.410 --> 00:29:58.269
frozen box. A box that was ahead of its time

00:29:58.269 --> 00:30:00.430
but just couldn't tell the time. Exactly. So

00:30:00.430 --> 00:30:02.630
the next time you see that punchline on TV or

00:30:02.630 --> 00:30:05.210
you see a picture of a Zune, don't just laugh.

00:30:05.369 --> 00:30:07.630
Pour one out for the squircle. It deserves a

00:30:07.630 --> 00:30:10.289
little respect. It really does. Thanks for taking

00:30:10.289 --> 00:30:12.190
this deep dive with us. It's been a trip down

00:30:12.190 --> 00:30:14.509
memory lane. A brown, double -shot injection,

00:30:14.890 --> 00:30:18.069
molded memory lane. The best kind. Thanks for

00:30:18.069 --> 00:30:19.670
listening, everyone. We'll catch you on the next

00:30:19.670 --> 00:30:20.109
deep dive.
