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Full transcript: Your questions about cloud services, answered on Too Embarrassed to Ask

“I have so many cloud services and I don’t understand any of them — and I’m pretty smart about this stuff, too.”

Melbourne Racing Vince Caligiuri / Getty

On this episode of Too Embarrassed to Ask, Recode’s Kara Swisher and The Verge’s Lauren Goode bring on Chris Bourdon, CEO of cloud service Upthere, to help answer reader and listener questions about the cloud.

You can read some of the highlights from their discussion at that link, or listen to it in the audio player above. Below, we’ve posted a lightly edited complete transcript of their conversation.

If you like this, be sure to subscribe to Too Embarrassed to Ask on iTunes, Google Play Music, TuneIn or Stitcher.

Kara Swisher: Hi. I’m Kara Swisher, executive editor of Recode.

Lauren Goode: I’m Lauren Goode, senior tech editor at The Verge.

KS: You’re listening to Too Embarrassed to Ask, where we answer all of your embarrassing questions about tech.

LG: Because, really, there are no embarrassing questions. It could be about phones or laptops or wireless plans ... what the hell is going on with Uber, Kara? That’s my question for you this week. What is going on with Uber?

KS: A lot of things. We’re doing a lot of stories on it on Recode, and so are you on The Verge, but it’s pretty much a mess. It’s a huge HR nightmare after a woman engineer who worked there wrote a really devastating essay about her experience there, which includes sexual harassment and pretty much rampant sexism across the company.

LG: And you actually had the memo that Travis Kalanick sent out yesterday to his staffers, explaining what they’re planning to do to address this. In fact, by the time this podcast publishes this week, there’ll probably be three more updates on this story, at least.

KS: Absolutely. It’s a fascinating story, and it’s also one that’s been long simmering, so it’s going to be kind of interesting as people come out of the woodwork to talk about their experiences of working at that company — and by the way all Silicon Valley companies, because this is not limited to Uber. This is a problem I know you and I hear about all the time from women who work in tech.

LG: Yeah. Not just tech, too. We certainly do hear this a lot, so it’s something we’re going to be following closely. That was my question for you this week. That’s it. Podcast over.

KS: All right. Readers can send us questions about that if they want, and we really do read them all. Find us on Twitter and tweet them to us at @recode, or to myself or to Lauren with the hashtag #TooEmbarrassed.

LG: We also have an email address. It’s, and a friendly reminder that "embarrassed" has two r’s and two s’s.

KS: While you’re at it, have a listen to our previous episodes too, which you can find on iTunes at

LG: This week’s episode is partly inspired by my sister-in-law, and I hope she doesn’t mind that I’m calling her out a little bit on the show, because a couple months ago, I was home for the holidays. By the way, she’s a very smart woman, she has multiple degrees. She said to me, “I am paying for, I think, eight different cloud services right now. I have no idea why I’m paying for them, exactly what they do or how they’re different.” She was genuinely confused by what the cloud is. I thought, “This is a good question. At some point, we should really tackle this, and try to answer people’s questions about cloud services.”

KS: Yeah. I’m the same way. I have so many cloud services and I don’t understand one of them, actually, and I’m pretty smart about this stuff too.

When we told our readers and listeners that this was the topic this week, we had a whole bunch of questions about this, so many that we can’t even answer them all in one show, because the cloud is so important to people, and yet they really are confused by it. This is an important area of consumer tech. Really, everything is in cloud service now, from photo storage and backups, to streaming media service, anything connected to the internet.

So we’re very excited to welcome Chris Bourdon to the show to answer your questions this week. Chris is the CEO of cloud service Upthere, which offers, among other things, a service called UpThere Home, which is supposed to be one single online storage space for all of your videos, photos, music and documents. He’s here to talk not just about his service, because he’s not here to promote Upthere, but also, all the others and how you can figure yourself out through it.

LG: That’s right, because Chris also worked at Apple for 15 years prior to Upthere, where he led product marketing for OS X, which is Apple’s desktop software and Mac’s software. Chris, thanks so much for joining us today.

Chris Bourdon: Thank you for having me. It’s great to be here.

LG: Talk a little bit about your path from Apple to Upthere. How did you get involved in the world of cloud storage?

I had worked at Apple for about 15 years, and I was the product marketing manager for Mac OS X, and then I worked on Mac OS 10 since the very early days of OS X, before it was even a consumer operating system. It was actually a server operating system at the beginning. I was there through all the cat releases, and during that time, I worked with a man named Bertrand Serlet, who at the time was the senior vice president of software engineering at Apple. He ran the OS X engineering project, and eventually was the guy who incubated the IOS project at Apple. He’s a very scientifically minded person. He left the company maybe six or seven years ago to go off and think about bigger problems, non-product problems.

The thing that he recognized, and that I also recognized when we were there was, the world was moving from something where we used one computer all the time to one where we had lots of computers. We had our laptops and our desktops, but now we added mobile phones and tablets and watches and all these other things. It became pretty apparent that the technology that all that was founded on, which was the same technology that was inside all the PCs, wasn’t really going to scale when we had all these different devices.

The company had set out to solve this problem with a new core technology that didn’t rely on the technologies that were kind of embedded in computers at the time, these older kind of UNIX-style POSIX filesystem-type technologies, and used a modern technology that was built specifically for mobile computing, where you had lots of devices, but you want to have all the same data available to you on all of them.

That’s kinda how I saw that this problem was emerging. I saw that, quite frankly, Apple was struggling with the cloud to do good stuff there, and I thought it was a great opportunity to go and try to really solve the problem at the core of the problem, not try to wallpaper over it, which is what sync does.

KS: What is the problem you’re trying to solve? What would you say if you make it easy for people? What would be the problem? It’s that there’s everything everywhere, right?

Yeah. I think that was kind of the problem is, in order to get your stuff on all your devices, you had to sync it all around, which is very complicated for people.

KS: It is.

It filled up your phone or it filled up your computer. People were having less and less storage space on their devices. Everyone has this problem “We’re running out of space because we have too many photos. We have too many applications on our phones.” That’s just because there’s this limitation to the size of these devices, and a limitation to the software that runs on these things.

Our goal was to build a new technology that would eradicate that problem, where we didn’t have to worry about how much space we had on our phones, that we could have very, very small amounts of storage on our phone, but yet have access to terabytes and terabytes of things. That was the foundational notion of why to go on to build this.

LG: How do you compete with giants like Apple and Google, Microsoft, people like Dropbox, as a cloud storage startup?

That’s a very good question. It’s obviously very hard to compete with them. First of all, our goal is to make the world’s best personal storage experience. We want this to be the best experience that anybody has available to them. We want to be as fast as possible, we want to take up no local storage, we want to have the best user interface and the best user experience. Job One for us is build the best product and the best experience for people. We provide one place for everything. When it comes to performance, we are faster than iCloud by about 2x. We’ve done the measurements on that. Goal One is: Make the best product possible.

We certainly recognize that there’s a difficulty competing with companies that have embedded the cloud, so to speak, into their devices. For us it’s going to be about ... we’re working on some new stuff. I don’t wanna talk too much about it now, but, that we think will ...

LG: It’s okay. It’s just us here. You can just tell us all about it.

We’re working on some new stuff that I think will show that we’re gonna aim at a particular kind of user who has a real need that’s not being served by these folks yet. The hobbyist photographer or the videographer, if you have a digital SLR, or you have an action cam, or you have a drone, these are very hard storage problems for people, very hard data-access problems for people, that these other services are not handling adequately right now. We’ve got something really interesting that we’re working on. Perhaps you’ll invite us back at some point and we’ll show you, that we’re really excited about that. We think it’s very differentiated from what’s happening in the markets today.

LG: It sounds like you’re going to be focusing more on a pro-level or hobbyist.

Yeah, it’s more hobbyist, travelographer, those kinds of folks. There’s a lot of these cameras in the world, that don’t have the convenience that your mobile phone has, when it comes to photos. They need to have that convenience, and that’s what we’re working on solving right now.

KS: All right. All right, you geeks, stop. Stop, you two geeks, for just a second. It’s really normal people, though, that have a problem. Most of us don’t fly drones around all the time, or other things like that. Could you just get into the idea of what the biggest problem of cloud storage service is right now for the normals, who just have photos, maybe some music, maybe some entertainment, videos of their family gatherings? I think that’s the use cases of most people.

Yeah. You know, I think if there’s a lot of choices, Lauren mentioned this at the beginning. You’ve got Dropbox, and you’ve got Box, and you’ve got Google and Microsoft and iCloud, and I think for consumers, Dropbox has really moved into more of an enterprise approach. They’re focusing a lot on the business. I think they’ve kind of left consumers behind. I don’t see a lot of stuff happening from Dropbox for consumers. Box has been in the business case for a long time.

I think that Google Photos is a really great service. If you’re looking for a place to keep your photos, other than, of course Upthere is a great one, but I think Google Photos does a really great job. You can get it in IOS, you can get it on Android. In fact they build it into Android, and it’s free if you buy the pixel phone, you get it for free. I think they do a really wonderful job. They’ve got great Search, they’ve got facial recognition and object recognition in there. They’ve got a lot of users. I think there’s a lot of really happy people.

I think the problem is, each of these services focuses on a very particular thing, and they try to do that one thing really well, so inevitably, if you want to get the best experience, you’re going to be using multiple clouds. Google does a great job with photos. If you have an iPhone, and you want to make sure that your phone is backed up and you can restore it if you lose your phone or you get a new phone, then iCloud is the only solution that you can get. There’s a free five gigabyte service there. You can pay a couple dollars to get 50 gigabytes, or a couple hundred gigabytes, and you’re going to have the safety and security of having your phone backed up. I think everybody wants that. If you lose your phone or you get a new phone, that’s really easy. I think Google Photos is great for photos. I think Apple’s iCloud is great for iPhone backup.

KS: Yeah, so essentially like streaming services. You’re gonna have to have all of them, because if you want Roku, if you want this, if you want that, you have to have several different ones. To me, that seems to be an enormous problem for people.

Yeah. I think that’s likely to be true. There’s a differentiation. The streaming services are trying to differentiate on content that they have on offer that you can’t get at other services, so you end up with a Roku and you end up with an Amazon Fire Stick, because you want Amazon TV. You end up with Apple stuff because you want their new TV show. In the case of cloud services for your things, yeah, they’re not particularly integrated. For photos you’re gonna use one thing, for documents you’re gonna use something else. That’s just how these services are, I think, evolving and becoming good at each of those things.

LG: It seems like, if you had to put this into different categories of users, you would say, “Okay. There are people who just want general backup.” They’re not thinking about it, they’re not doing anything manually, they just know their stuff, maybe on their phone, is being backed up somewhere.

Then you have the photo hounds, who say, “Okay. Where can I not only store but actually manage my photos?” You’ve got people who need backups to documents, and they might be using something like Google Drive or Microsoft OneDrive, and then you’ve got the people that Kara won’t let us talk about. The hobbyists and the nerds and the geeks. By the way, I would put myself a little bit in that category because at one point, I was a video producer.

KS: You can talk about ’em!

LG: I did a lot of manual control over what was being backed up. I never have liked the idea of thinking all the junk on my phone and on my desktop is just being uploaded somewhere. I would actually prefer to sort of manually manage it and put it into folders, but that’s a whole other topic.

How secure are most of these services, because that’s another thing that people ask us a lot. They say, “Okay, I’m starting to back everything up into the cloud,” and we’ve seen cases of celebrities having their cloud accounts hacked and photos being exposed. How secure is it?

I think the security of most of these services is quite excellent. The problem that you see particularly with the celebrity hacking of iCloud, was not so much that the service was insecure in and of itself, it was that people are largely insecure with their information. It’s fairly common for people to get phished or hacked for their information. I think that’s what happened in the iCloud incident. People sent emails to celebrities, or were able to find out personal information about them, that let the phisher change the celebrities’ passwords, so that they could get into their account.

That’s the weakest link right now, in all security, is the user password. Some services have a second authentication. That’s possible, so you not only have to have a password, but you have to have a code. That code can be delivered to your phone, either through SMS or through an application like Google Authenticator.

LG: Does Upthere have that?

We do, actually. We were one of the first services ever to launch on Day One with two-factor authentication. This give you an extra level of protection. I recommend anybody who cares about the security of their stuff, which should be everybody, should have a second-factor authentication enabled on for the service that they’re using.

The services themselves have proven to be pretty secure. You don’t hear very often about hacks of Google’s service or of Dropbox’s service, because it’s hard. It’s hard for even the best hackers to find ways into those services. They’re very well protected in lots of ways, both physically and through the software infrastructure. It’s much easier to try to get people’s password information, much easier to try to take personally identifiable information of somebody and try to hack their password. So that’s where people have focused.

It’s an area that I think still deserves a lot of development. It’s a big hassle to manage your passwords today. I use an app called 1Password to manage my passwords, and I have a hundred different entries in there, all with different passwords because that’s the right thing to do. You wanna have a different password for every service, you can’t remember 100 passwords, so it’s very clunky and cumbersome. It’d be wonderful to see the industry move forward in figuring out how to provide better authentication mechanisms, but that I think is the biggest security problem that we have today.

LG: Kara, are you ever worried about your iCloud services being hacked?

KS: Constantly. I have everything. All the authentication I have, I put in there. I think it’s one of these things, that you’re trusting everything not to some ... then at the same time, maybe you have a backup that’s just sitting in your house that could be stolen, but it’s a whole lot harder than it is with these things. So I’m constantly changing passwords and doing stuff like that. I think it’s a matter of time before most people are going to get into trouble on some account in this area. It’s like email and everything else.

All right, so in a minute, we’re gonna answer some questions from our readers and listeners about cloud services, but first we’re gonna take a quick break as Lauren reads a word from our sponsor. I have to say “ka-ching.”

LG: I don’t care and you’re not here this week. Again. You’re in D.C. What are you doing down there?

KS: Donald’s out of town and Melania invited me over for a ladies’ night. I’m very excited about that.

LG: Oh really?

KS: Yeah, mm-hmm. We’re close.

LG: What are you guys gonna talk about?

KS: You know, cloud services, probably, a little bit. Some other issues. No.

LG: Maybe you can tell her to get her husband off of that insecure Android phone while you’re at it.

KS: I don’t know, but we’re gonna take it and flush it down the White House toilet or something.

LG: Among other things, that’s kind of low priority right now.

KS: Yeah. Mm-hmm.

LG: Okay, well, I miss seeing you in person and hearing the “ka-ching.”

KS: Ka-ching! Go ahead, I wanna hear this ad now, so we can get to the questions from our readers.


KS: Well Lauren, that was a big ka-ching, as far as I was concerned.

LG: Ka-ching!

KS: Okay, if you’re listening to this show, you know how it works. Every week we take tech questions from our readers and listeners, and we try to answer everything we can. This week, we’re answering your questions on a whole bunch of different cloud storage and streaming media services. Lauren, why don’t you take the first question, and I’ll go from there.

LG: Sure thing. The first question is from Christopher Mims, who’s at the Wall Street Journal. By the way, we got at least two questions this week from other journalists.

KS: Oh, my goodness.

LG: Which is the funniest thing, because I’m like, “Guys, let me google that for you.” But Chris Mims from the Journal wants to know, “For a consumer, is one any better than the other, or are they all more or less commodities at this point?”

I’m gonna go through the pricing of these really quickly, and I won’t get too detailed because there’s a lot here. Basically, they’re all pretty similar at this point, from a consumer perspective. They do vary by region, so the prices might be different depending on where you are geographically, but a lot of them will start you with a certain amount of storage free, and then they get you to start paying.

Google Drive is 15 gigabytes free to start. Dropbox Basic is two gigabytes free to start. Apple iCloud, five gigabytes. Microsoft OneDrive, five gigabytes, so right off the bat we can see that Google Drive is the best deal. After that, you start to pay $1.99 a month, $2.99 a month for things like 50 gigabytes of storage, 100 gigabytes of storage.

Then if you’re really storing a lot of stuff, you can get up into terabytes. You can pay for one terabyte of storage on Google Drive for $10 a month, you can go up to 10 terabytes with that. Microsoft OneDrive goes up to one terabyte for $70 a year. Basically, you’re just going to have to look at the tiers of pricing and figure out what works best for you.

The one thing I will point out is that people look at Apple iCloud and Apple iCloud Drive, and they get confused. They say, “What is the difference between these two?” iCloud is really that thing, this is based on my experience, they’re gonna want to use, as Chris mentioned earlier, to just basically back up your phone. That’s gonna back up your phone, it’s gonna back up your Mac. If you wanted to get into more file management or document management, that’s when you’d start using iCloud Drive. iCloud Drive is sort of looped into the pricing, when you start paying for iCloud, along with Apple Photos and a bunch of other stuff like that. Maybe that’s one of the more confusing things for people, because almost every other service kind of has this singular name. Chris, is there anything you would add to that?

The services have become fairly commoditized when it comes to different pricing structures, and I think it’s because people just see gigabytes of storage, and not an experience behind it. For iCloud, I think you’re right, there’s one thing called iCloud, but there’s all these different services that go to fill up the iCloud storage. Same is true with Google. Your Google Photos, you’ve got Google Mail, you’ve got Google Drive. Those all contribute to the same quota of content that you use. But it’s one quota of content.

LG: Yeah, that’s a great point. People probably don’t think that much about Google Mail taking up their storage space.

That’s right.

LG: In terms of Upthere, you have a service, you have Upthere, but you have a service called Upthere Home. How many different services or tiers do you guys offer?

We give you three months for free, basically, use whatever you want, and then we simply price it a $1.99 for every 100 gigabytes you use. It’s a pay-as-you-go. We wanted to make sure you weren’t overpaying for your gigabytes. Most people have less than 100 gigabytes of stuff. If you are using Dropbox at $10 a month, you’re paying kind of a lot of money for those 100 gigabytes. We wanted to price it a little bit more in line with how people use their stuff, so $2 for every 100 gigabytes. Very simple.

LG: I feel like I just keep paying for more and more of these services, same problem that my sister-in-law has.

KS: I have ’em all.

LG: One day you wake up and you look at your credit card statement, and you say, “Wow! I’m really paying for a lot of this stuff!”

KS: I have every one of these. I have Google Drive, I have Dropbox, I have iCloud Drive and I have Microsoft OneDrive. It’s amazing. I just have ’em all for different things. I think about consolidating them a lot. I have also Google Photos, which is another one. I did have Flickr, many years ago, but who knows what’s going on there.

LG: Oh, Flickr.

KS: Next question is from Chris Davies, who’s also a journalist. I think that is that Chris Davies. “Which is the easiest to set up remotely if, say, you’re getting less tech-savvy friends up and running?” Chris, which one is the easiest besides yours? You cannot say your own.

Oh, goodness.

KS: Just say, “Mine and.”

Of course, Upthere and, but gosh, if you’re an Apple user, setting it up remotely for another person is going to be very hard. You really need to set it up when you set up your device, or when you get a new computer. You really need to do that. I think Google’s probably more abstract, in a way, from the device. I think they’re all hard to set up remotely, because, inevitably, you need to be in control of the email address that’s behind it. If you have control of the email address, then it’s easy to set up, because you get a verification in email, and you need to be able to answer that.

I would say, of those two, I don’t have a lot of experience with Microsoft. I think that if you’re using Office, you basically are being forced into the OneDrive cloud through Office Now.

LG: Office 365?

Yeah, Office 365 is kind of the way to get onto Microsoft’s cloud. So remotely, you really need to have access to either the email address, or sometimes a phone number in order to finish the setup. I think remote is tough, but probably Google is the easiest one.

LG: I know at one point I tried to set my dad up with Dropbox after a vacation, when there was lots of photo-sharing happening, and it was ... I think it was futile.

Okay, next question is from Jeremy Fake. He’s @jfake on Twitter. “I want to have my photos, including raw, in the cloud, but want facial recognition. What’s the best?” Okay, so for non-photographers, raw photos basically means the original photos in the largest file format, with all of the detail that your camera could possibly capture for that photo. In a lot of cases, photos end up being compressed, which means they’re no longer raw. This particular person says, “I want to have the giant, original photo stored in cloud service, but also facial recognition,” which is something that Google does now, Apple does now. What are your thoughts on that?

That’s a tough one. If you have JPEGs, obviously for the users that are Kara’s friends, your phone and the JPEGs that are taken on your phone are all easily facially recognized by all the services now.

Raw files, I’m not sure on. I know that Apple platform recognizes the raw file and can display some of them. I’ll assume that, that because they have facial recognition on the device, that they can apply that to the raw files. Usually, what happens from a Tentacle perspective is that the device or the cloud will convert it into JPEG, convert the raw into a JPEG and then do the actual facial recognition. I don’t know what Google does, honestly on that.

We support raw files, we don’t have the facial recognition part, but we have full raw file support. I’m not sure if anybody gives you those two combinations of things with a pure cloud service.

LG: That’s a really good question. We’re going to have to look into that further.

KS: Exactly. “Serious question, I want to use iCloud Photo Library, but I don’t want all my previous photos to be uploaded if possible.” Lauren says, “You mean the ones that exist on your iPhone now? You don’t want those backed up? Only new photos going forward?” and Don Juan says, “Bingo! Exactly that, or maybe I bought a new iPhone and I want all those new ones up in iCloud going forward.” A very sexy conversation. What do you think, Chris?


LG: I know. Hot! Hot TETA action.

Yeah, I mean, certainly the default setting for all these services is, “Hey, just give me all my stuff.” What you want to do is find a service that lets you selectively upload things, so that in addition to the option of enabling an upload of your entire photo gallery, that there’s also an alternative option, which is to selectively upload what you want. Upthere of course provides that. I think a lot of the services probably do.

I don’t know of anybody who says, “As of this date forward, I want to upload them, and not the old ones.”

LG: I would think that the way you’d have to do it, if I were to guess, would be, I’m just really kind of riffing right now, you’d take your existing iPhone, and you would plug it in, and you would dump all of your photos to a local hard drive, right?

Yeah. Then delete your phone.

LG: Then you’d wipe that phone, and when you got a new iPhone, you would not restore it from an iCloud backup.

KS: Oh, my God.

LG: You would just start it as a new phone, and at that point, set up your iCloud backup.

But I think if you set up iCloud at that point, for photos, it’s going to bring all the old photos.

LG: It will. It will, I’ve had that happen.

And move it from the cloud to your new phone.

LG: It just does what it wants. Really, it does.

This is a very ...

LG: It does. It just starts sucking things in.

I don’t know what kind of photos Don Juan has, “the past” ... those might be more interesting than this conversation about it.

KS: This next question, Lauren, ask this, because this is a problem I have had all the time.

LG: Okay, this is from Jamie Rwanda, who wants to know, “Is it easy to get your photos out of iCloud to transfer them to another service?”

KS: No, No. No.

LG: “Based on what I have read, it’s hard to do this in batches, that you can do it individually, but it’s hard to just export ’em all.”

KS: Yes. It’s horrible.

LG: What do you say, Chris?

I think I should, this shouldn’t be too hard.

KS: No. it is. Why isn’t it?

Oh it is. Okay. Here’s how I think about it. You’ve got all your photos on iCloud. If you install Google Photos app, and you say, “Upload all of my photos,” it’s going to go and it’s going to grab all the photos that are on your phone, but that essentially are also on iCloud. It’ll upload them to Google Photos. We do exactly the same thing, where you can just tap a button, and it will take all of your photos out of your IOS gallery, and it will upload them to Upthere. I assume other folks do that.

The problem is, you can’t get away from the iCloud gallery part of things.

KS: Exactly.

Because that’s essentially where all the photos go on IOS. You can move your photos to another service, but you can’t kinda get yourself out of the iCloud service part.

KS: You cannot.

Apple really does not want you to do that.

KS: Yeah. That’s the issue. I wanted to eradicate them.

Now, if you take a photo, I would send Apple email at, and ask them to allow third parties to just be the gallery for the phone. That would be one way to do it. Right now, you have to store all the photos taken on the iPhone to the iPhone’s gallery, and then you can move them in other services.

KS: You can erase them. I’ve talked to Apple about this, because it makes me mad that I can’t just get rid of photos if I want. I don’t want them on the iCloud service for example, and I should have the right to take them off, right, so that’s the idea? I think what I have done, is they said you have to delete them in batches, and I have, you know, 30,000 photos. I have to set aside a lovely afternoon to do it, and it’s really mind-numbing to do it. The only way to do it is to get rid of them all at once in batches of a thousand, or something like that. And then, future photos always get uploaded there anyway, so you have to remember to get rid of those. You have zero choice for it not to be your photo service, which is irritating.

I think you should check out one setting that exists, I believe in Google Photos. It allows you to delete the photos in the gallery. It’s not an on-by-default setting. If you go into the settings on Google Photos, there should be something that says, “Delete the photos from the gallery after I’ve uploaded them to Google Photos.”

LG: It sounds like, to answer Jamie’s question, it should be relatively easy to get your photos from iCloud to another service, but it sounds like it’s more challenging just to delete them entirely. That’s where you’re going to be spending some time going through and doing some manual deletion, which is annoying.

Our next question is from Joey Pore on Twitter. “Why hasn’t Apple made a family-compatible iCloud storage plan? I wish I could pay $10 a month for one terabyte for everyone.” That’s a good question. You know, Apple’s not the greatest at multiple accounts or users on, let’s say, one device, right? I think they do that in the education market, but for example, it’s not like you can just log your child in or out of your iPad, and then log yourself back in, and that sort of thing. It’s not surprising to me that they’re not doing iCloud storage that way anyway.

Then again, there are probably challenges around it. Like what if your child or your partner’s photos suddenly got interspersed with your own? How would you ...

That would be not fun. I think they have some family stuff, so when you buy music. They have a family music plan through iTunes or Music, or whatever it’s called now. I think it’s $15 a month for the music plan, and then everybody in the family can listen to music from the same account. They have the ability for families to share, I think, an app store as well. I know that I get messages from my son all the time asking to approve a particular application. I don’t know if they have the ability to share, sounds like they don’t have the ability yet to share gigabytes of storage in a family plan. That would be a really great thing for them to provide.

LG: It would.

There shouldn’t be any problem with user accounts. That part’s not hard. They should be able to do that.

LG: Another question about Apple from Gilbert Jaramillo. He’s @therealgrj on Twitter. “What’s the best solution for an Apple household to back up photos?” Probably iCloud. Unless you think at some point you’re not going to be an Apple device user and you just want your photos in a place like Google Photos.

Yeah, if you’re committed to Apple, then there’s nothing that’s going to be easier. They have access to the devices that other developers don’t have. I don’t think that necessarily makes it easier. I think Google Photos again is a great example of something that probably does a better job of holding your photos than Apple does. Dropbox has kinda gotten out of the photo game, for the most part, so I don’t think that’s a real good option.

There’s also, if you’re just thinking about backup, you’re not looking for access online, then you can look at things like Carbonite or CrashPlan, or other things that are just focused on backup, and they’re probably better backup solutions than Time Machine as of this point, which really hasn’t advanced much in the last buncha years.

I don’t know that the Apple-only solution is ultimately the best one. I think it’s convenient from an activation perspective, but I think the other things out there today are just as good, and they give you more flexibility. You may not like the next Apple device. You may like the Android. The Google Pixel’s a pretty nice phone. I have one. I enjoy it. I think having that kind of independence of our data from our devices is pretty important. When you start putting all of your eggs in one basket, so to speak, you’re really exposing yourself, not only to the fickleness of the company and how they decide that they’re going to pursue their business in the future, but also the security of that company and the longevity of that company. I think spreading your love around a little bit’s not a bad idea.

KS: Yeah. One of the things is that Apple’s iPhoto just is not a good program. You know what I mean, like that’s the problem with so much of their software, is that it’s just not a satisfying experience, compared to the others as they start to evolve. They don’t seem to be putting enough effort into it, given how the others have. I agree with you, it’s hard to ...

LG: I would make the argument that Apple Photos on desktop, I like for the editing that they offer in it now.

KS: Yeah, editing. Different.

LG: Because they have made a lot of changes to the Photos app. I think I like editing in Apple Photos on desktop better than I do Google Photos. There’s still just a lot of confusion around that.

KS: But finding, most people are just looking for a photo they took in Lisbon, you know what I mean? That’s the problem, is finding is literally almost impossible on Apple Photo service.

LG: Yeah. Just searching, like “Kara at White House Ladies Luncheon with Melania.” Just being able to search for that, you know?

KS: Exactly.

LG: “Kara riding a horse in the style of Putin.” I just want to be able to pull that up.

KS: It’s hard to pull that up. Yeah, yeah absolutely. All right, the next question from Zach Dubos: “The Nextbit Robin is really cool. How well does this work, and do you think other brands will implement this?” I don’t even know what that is! Why don’t you explain, Chris or Lauren?

LG: Ohhh!

KS: Ohh.

LG: Do you mind if I weigh in? The Nextbit Robin, I have some feelings on this. Nextbit is a startup company that was making Android phones, unlocked Android phones. They had this very cool design. There were like these square, robin-blue-colored phones. More than the aesthetics, what they were doing that was interesting, was they would basically uninstall apps that you were not using, or actively using, to save space on your phone. They would arbitrarily do this, and then if you needed to use the app again, you would tap on it and it would reappear on the device.

They were doing this kind of behind-the-scenes, proactive, cloud-storage management of some of the stuff that was going on on your phone. Nextbit happened to have just been acquired by the gaming laptop maker Razer. My understanding is that they’re still gonna continue to make phones. It was cool. I only used the Robin for a short period of time, but in some ways it reminded me a little bit of iTunes Match. The idea of taking the apps on your phone and saying, “Okay, we’re gonna decide for you that this one is going up in the cloud now.” That kind of arbitrary decision-making around cloud stuff tends to bug me a little bit, but it’s a cool idea. What are your thoughts on it?

Yeah, I think philosophically, it’s interesting. Inevitably, I think we’re gonna get there. We don’t wanna keep buying phones with 256 gigabytes of memory in them, that kind of sounds silly. Because, inevitably, we can’t keep our things on there. I think philosophically, they have a good idea of, “Hey. My apps take up space, my photos take up space. Let me sync off all my photos, and then delete them locally. Let me sync off my apps and then delete them locally, and then leave a little thing behind.”

I think that the problem is that their approach is largely fairly kludgy to this, and inevitably, applications need to change underneath the covers. You know, the technical aspect of the apps need to adjust in order to behave properly in this environment, to actually give you the real benefits of having an app that is not locally resident, but yet performs as if it feels like it is. As far as photos go, that’s a long way to go just to do a photo gallery in the cloud, which already exists either through Google or Apple or us. It feels like having a whole new phone for this is unnecessary, that a lot of this benefit is given to us through services that exist already.

LG: So you don’t need to buy this special “cloud phone.” You can buy any hardware you want, and have most of those cloud services. I guess the idea that it was sort of baked in, I don’t know.

I actually saw someone on the street the other day using the Nextbit Robin, and I think that was one of the few times I saw it in awhile. Then again, we’re in San Francisco. I feel like this is also where people were wearing Google Glass for a while, so let’s not talk about that.

We actually got a couple of streaming music questions. As we mentioned earlier in this show, all of these are cloud services, but there’s definitely a difference between cloud storage and then media streaming services, like your favorite video or music streaming apps. But people did send us some questions. Kara, do you want to read them?

KS: Sure. The first one is from Tech Coolness, to you Lauren. “Too lazy to google this.” Who’s too lazy to google anything? That’s really lazy. “Is there a way to get all of Google Drive, plus YouTube Red, minus Google Music, with a single subscription?” I have no idea. I don’t use any of these things.

LG: Is there a way to get a singular Google messaging app, while we’re at it? Google just seems to ... they love having multiple services that do a variation of the same thing.

KS: They want lotsa hooks into you, that’s what they like. Why is that, Lauren? What’s the deal with the Googles?

LG: If you’re paying for Google Drive, that’s a separate fee than what you’re going to pay for the $10 a month for access to YouTube Red, which is YouTube without ads, and/or Google Music, which is their music streaming service. I believe the company is making moves to combine them, possibly. They combined the teams, we reported recently. They were working on YouTube Red and Google Music. In short, “No,” Tech Coolness. You’re gonna end up paying for Google Drive. After you get through that 15 gigabytes of free storage you’re gonna end up paying a couple dollars a month, or whatever it is, and then you’re gonna pay for streaming music in some capacity.

KS: Yeah. So you’re just gonna keep paying Google.

Yeah, the business models there are just so different.

KS: Right? Chris, you’re gonna pay Google all the time, really. In some way.

You are. Or they’re gonna sell your data for you, to monetize it through ads. Either way.

KS: Yeah. Oh, I’m already all over that. Yeah, of course they are.

LG: Yeah, right! As we said in last podcast, “No free lunch.”

No free lunch.

KS: Can I ask you, Chris? Is that harder, because they’ve got lotsa ways, lotsa leverage to make money. When you’re competing, they can make it through advertising, they could make it through all these subscription services, and then Drive and everything else. Is that harder to compete against? I would assume the answer is yes.

Oh, for sure. If somebody’s offering something for free, then you can see the traction that free services get over non-free services. The data is out there. It’s important that people who are using free services know who the customer is. The customer’s not you. The customer is the ad network.

Look, when it comes to streaming TV shows and video, you don’t really care, right? You don’t own those things, so having some ads on there is no big deal. For Facebook, largely no big deal that you have some ads on there. It’s not really like your stuff.

My perspective is, and I feel very strongly about this, this is my stuff. I’ve made this stuff, I want to keep this stuff for a long time, I want to keep the full fidelity of this stuff. I don’t want my stuff to be at the whim of a decision that a company makes because they’ve got a business change or a business challenge that they can’t meet properly. I feel like when there’s a direct relationship between me and the company, as a paying customer, that company is properly incented to do the right thing for my things. That’s the philosophy for us at Upthere, and why we charge $2 a month for 100 gigabytes, because we want the relationship to be directly with the customer. We think that’s the right thing.

KS: No, I think that’s correct. I think it’s hard, because it’s like Amazon and Netflix in a lot of ways. Amazon’s doing a lot of other things besides making “Transparent” or selling you music or video. They’re also selling you toilet paper, which is part of their business plan. Netflix does not have toilet paper to sell, so it’s an interesting problem. You have to just be better, just better in some way that differentiates you.

Why don’t you ask the last question, Lauren.

LG: The last question is from F. Reed. He’s @lowtech on Twitter. Honestly, this question, I feel, could spawn an entire separate podcast, so at some point, we are going to have to do a podcast just about streaming music services. This person asks, “Is streaming music worth it? I can buy 10 songs a month for what streaming music costs, and own those songs forever.”

I think it depends on your listening habits, personally. I realize that I am the type of person, I will wear a song or an album out, for a period of time, and just listen to it over and over again because I’m really into it, and then I’m over it and I move on to the next thing. So for me, I feel that paying $10 a month for having unlimited listens and all of that to something I might eventually grow tired of and not want to own, is a good deal for me. But some people are really audiophiles, and they’re really into their music, and they still like owning music. I think that all just depends on your mentality, around that. What do you guys think?

KS: Oh, well I think buying music is over. Buying music is over, pretty much. I have piles and piles of CDs and everything else, and stuff that’s in my stuff. Streaming music is where it’s at. I don’t know. Chris, why don’t you have the last word on this.

I agree that it’s by use case. I agree that I think pretty much everything is gonna be streaming music. The reason is, you actually don’t own that music. Ownership of a file is kind of a bygone notion for music. There are different use cases for listening. I think like Lauren said, if you’re an audiophile, and you want to listen on a very nice set of speakers or headphones, you want high-quality, high-resolution music. And you can get that from services, like Title, for example. I think there’s, Deezer, I think, had high resolution music. If you just want to listen to the latest hits on your iPhone, with the ear pods or whatever, then Apple Music or Spotify or whatever, at 256 megabits streaming, is perfectly adequate. You’re not gonna hear the difference.

I do think that owning the files is something for the past, and that streaming music is the way to go. You just need to find the one that gives you the experience that you wanna have, given your listening needs.

LG: One of the things that I’ve had happen recently, is I’m using a lot of streaming music services, and iTunes is now also kind of arbitrarily throwing songs up in the cloud when it feels like it, right? Whether you’re paying for iTunes Match or not. I’ll forget to go back in and tap a little cloud to re-download the song before I get on a plane or something, and then I have no service for awhile and I have no music to listen to, or I don’t have the music that I want to listen to.

KS: Oh dear.

LG: Because you can sort of store the things locally, but it’s not the same as having files, you know the MP3 stored locally.

I think this is a weakness of the services that haven’t been creative enough in applying the right technology to solving that problem. You can’t have all the music on your phone, but there’s some subset of music that you wanna have on your phone. You don’t wanna have to think about putting it on your phone. I don’t think it’s a particularly complicated technical problem to cache music and to cache things on the phone, and have them when you need them. This is just, these services need to evolve more.

KS: Absolutely.

LG: You know what, if you guys ever pivot, Chris? Do that, please. Fix that.

KS: All right.

LG: That would be amazing.

KS: You could also, Lauren, just sit on a plane and think to yourself. I know that’s a hard concept to imagine in this day and age, but you could actually just have a moment of reflection.

LG: I do that sometimes! I do that for the first, you know 20 minutes or so, until we reach 30,000 feet.

KS: All right! Oh, my God.

LG: Or whatever it is, and then I’m like, twitchy.

KS: Must be crazy-making. Anyway, thank you so much, Chris, for coming on the show. Chris Bourdon from Upthere, which is a cloud storage service. It’s still confusing to do this, but over time let’s hope a lot of this stuff gets very intuitive and changes even more, so that it’s easier for us not to even think about it.

This has been another great episode of Too Embarrassed to Ask. Thank you, Chris, for joining us.

Thank you, Kara and Lauren.

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