Dave Hamilton is the co-founder of both The Mac Observer and BackBeat Media. He is also the producer and co-host of The Mac Observer’s Mac Geek Gab Podcast. Dave has been involved in the computer and technology industry for over 15 years, doing work as not only a consultant and trainer but also a network engineer, webmaster, and programmer. Earlier, in his consulting days, he worked on the Mac, all the various Windows flavors, BeOS, a few brands of Unix, and it is rumored he once saw an OS/2 machine in action. Previous to his consulting experience he ran some of the earliest Bulletin Board systems.

Dave maintains his blog at DaveTheNerd.com

Narrator: Speakers, publishers, coaches and infomarketers unite. The Speaking of Wealth Show is your roadmap to success and significance. Learn the latest tools, technologies and tactics to get more bookings, sell more products and attract more clients. If you’re looking to increase your direct response sales, create a big time personal brand and become the go-to guru, the Speaking of Wealth show is for you. Here’s your host, Jason Hartman.

Jason Hartman: Welcome to the Speaking of Wealth Show. This is your host, Jason Hartman, where we discuss profit strategies for speakers, publishers, authors, consultants, coaches, infomarketers, and just go over a whole bunch of exciting things that you can use to increase your business, to make your business more successful and more and more passive and more and more automated and more and more scalable. So we will be back with a great interview. Be sure to visit us at SpeakingofWealth.com. You can take advantage of our blog, subscribe to the RSS feed and many other resources for free at SpeakingofWealth.com. And we will be back with a great interview for you in less than 60 seconds.

Start of Interview with Dave Hamilton

Jason Hartman: Hey, it’s my pleasure to welcome Dave Hamilton to the show. He is the cofounder of MAC Observer and Backbeat Media. And he’s the producer and co-host of TMO’s Mac Geek Gab podcast. He’s got a long background in the computer industry and we want to talk to him today about get a little bit of Apple news but not only that – we want to talk to him about security for our emails and so forth and we always want to talk about how to become successful at things like blogging and podcasting. And his company, Backbeat Media, sells advertising on his outlets. So we’ll hear all about this stuff and it’s great to have him on the show. Dave, welcome. How are you?

Dave Hamilton: I’m doing great, Jason. Thanks for having me. It’s a pleasure to be here.

Jason Hartman: Well, the pleasure is all ours. And you’re coming to us from New Hampshire today I believe, right?

Dave Hamilton: I believe that’s correct, yes. If I look outside, it looks like New Hampshire to me. That’s right.

Jason Hartman: Fantastic. Well, tell us a little bit about your background. Before we jump into some of these other topics about being successful at publishing, podcasting and so forth, I want to ask you what you think Apple will announce next at their next meeting coming up.

Dave Hamilton: Yeah, okay, so background real quick – I started…It was my dream as a kid – this is gonna be weird – to be weird – to be a computer consultant. Okay, so I actually did that. I realized my dream and was doing that for a long time, and then realized I could not scale that business well. And this is gonna be me tooting my own horn right out of the gate – my clients didn’t want anyone that I hired to send to them, they wanted me. And so that is flattering and profitable to a degree, but I had to carry every elephant and earn every dollar. And so I decided sort of haphazardly to invest in what became the MAC Observer and that worked out really well because I didn’t know anything about publishing and I didn’t know anything about sales. And so I had to hire people to do these things that I couldn’t do and that was a much different experience and of course allows you to scale. And so that was 2 years ago we started the MAC Observer and I started with a partner who worked on the content and then our first full-time employee that we hired was a sales rep for the advertising on the site because I realized very quickly the sales have to be a full-time job because it’s so rooted in negativity that I would do other things during the day to feel productive. But, of course, we weren’t bringing in enough money. So from of that, many of our what I’ll call our competitors – I mean they were our MAC publishing brothers but we did compete with each other – they came to us and said, hey, will you sell our ads for us too so that we can just do the publishing thing because that’s what we do. And so that’s what called us to spin off Backbeat Media about a year in with the MAC Observer and both of those have been going strong since.

Jason Hartman: Okay, so here’s some questions for you because a lot of people listening, if they’re doing a podcast or thinking of doing a podcast, they’d really like to monetize it beyond…The traditional podcast monetization strategy is to build your brand and build your business which works great by the way and that has worked great for me. I’m very grateful with the results I’ve had from podcasting. But if you can add a layer of say advertising to it, hey, then you got 2 revenue streams, right? So Backbeat Media, you had one sales rep originally. How many do you have now? Just one still?

Dave Hamilton: No, we actually have 3 going.

Jason Hartman: Are they like fulltime people? Commission only, salaried?

Dave Hamilton: Mixture of both. Yeah, they have base salary and then commission on top of that. I firmly believe in paying salespeople a base salary because there’s gonna be times when I asked them to do thing and need them to do things that aren’t able to earn them a commission and I need them to feel responsible to do those things. You can work it out either way. If you’ve got good people, they’re gonna do the things that they need to do. But I found that to be an easier model.

Jason Hartman: And so is that a virtual company or do you have like a traditional office and everybody’s in one location?

Dave Hamilton: It is currently a virtual company. It started as a virtual company. We have had periods of time where we’ve had offices in various places, including down in Austin, Texas for a while, but we are back to being virtual now. And the MAC observer’s a virtual company as well. And that’s a very interesting thing. Keeping a team feeling like they are a team and working together is not something that happens automatically with a virtual company. And I think it’s a really important thing, so working every day making sure everybody’s in sync, we probably spend a little more time – I hate meetings in a general sense, but I found that you need to have some of time each day where everyone is talking to each other and then we all go off and do our work and we try to keep their meetings very short, but sometimes they go long and that’s okay. But the goal is 5-10 minutes maybe and then that’s that, but it does tie us all together and remind us that, yeah, we’re not just holed up alone.

Jason Hartman: Right, exactly. Do you mind sharing some stuff about that business model? And, if anybody listening is interested, we rep other shows. We just strictly do these MAC shows. Say someone listening wants to sell advertising on their podcast? Would you bring them the advertising dollars? And of course it’s the revenue share, I’m sure. So tell us a little about that.

Dave Hamilton: Yeah, it’s a rev share. And I’m totally find being public with our deal. It’s 50/50 with all of our publishers and that seems to work out very, very well for everyone involved. Obviously, the publisher pays us nothing until we sell their first ad, so there’s work done on both sides. But, yeah, we definitely work with other publishers than just the properties that I’m directly involved with and it works out very, very well. In terms of the websites that we rep, we’re very much focused on the MAC Apple-space. We have a huge foothold there. We have contacts throughout that. So that works very well for us. With podcasts, we’ve actually found that we can stretch out a little bit more than that. That’s sort of where we started but we’ve got shows like Coverville and things like that where it’s related enough that it makes sense for a lot of the advertisers we work with to be on those shows. So yeah, so it works out okay.

Jason Hartman: Good, good. How do you price podcast advertising? If someone wants to do it through your agency or do it themselves, what should they expect in terms of what they can sell advertising for?

Dave Hamilton: Yeah, there’s a lot of different ways to do it. We are firm believers in what I’ve always referred to as the Howard Stern model, but that’s because I grew up near New York and so Howard Stern was always on the radio every morning, but the talking points model which is what NPR does and a lot of other podcaster too. We’re not doing a canned spot, we’re doing the host read and really a host interpretation if you will of talking points that the sponsor provides. We provide them…We guarantee a minimum period of time for it to be discussed, but leveraging on that relationship that the podcaster has with their listeners. And it has to be an honest thing. The podcaster has to identify that they’re doing a sponsorship spot and that sort of thing, but it really works well.

And as far as pricing that, we do it as a flat rate per show, but the way that we come up with the price for each show is looking at the number of subscribers, the number of individual people that download each episode on average and then we multiply that by a CPM rate, cost per thousand in the advertising world.

Jason Hartman: So give us an example of that. Like what would a small or medium sized podcast have as a CPM and then what would they charge for that and what’s the revenue they could make?

Dave Hamilton: So the CPM rate for us in what I’ll call the tech world is arguably lower than what you’re gonna see elsewhere just because there’s a lot of inventory in the tech world. So, €that CPM for podcasts sit somewhere between about the $20 mark on the low side and maybe the $35 mark on the high side. So depending on not only how many listeners you have but what kind of cache, what kind of influence your show has in its respective industry, you can nudge that number of towards the higher side. And, of course, if you’re sold out, then that means your rates should go up – that’s sort of how that works. But let’s say somebody has a show where they’ve got 20,000 people that listen to the show, then you’re looking at $500-$600 bucks on the low-end and maybe $1000 on the high end per sponsorship per episode, and you might – depending on the length of your show – you might find that you can fit 2 sponsorships or maybe even 3 per episode. And if you’re doing say 1 to 3 minutes per sponsor, if you’ve got an hour long show, two ads in there is totally fine.

Jason Hartman: Good stuff. Just speak to us for just a moment. We’ve got a lot of stuff to cover, but how does someone become successful at podcasting?

Dave Hamilton: Yeah, so there’s two keys – and I’m gonna say there’s 2 and then I might list 4 – but the first is the easy part and that’s the passion. You have to want to do a podcast about something, right. It starts easy. Maintaining that passion, to do it regularly, is part of the trick. So you have to, like you’re doing here, you reach out and you find new people to interview and finding people to talk about and that excites you – presumably excites you enough to actually fire up the computer and turn on the microphone, right? That’s what you do.

Number 2 dovetails into that and it’s consistency. One thing I hear – and I don’t hear quite so often nowadays from podcasters – but certainly when things were starting out 8-9 years ago – I heard a lot of podcasters saying the best part is I can podcast on my schedule because then I just publish it to my feed and my listeners can listen whenever they want.

Jason Hartman: I’m so glad you brought this up because that is one of the things I say. I run a network of 16 different shows. We’ve got about 1200 episodes now, and podcasting has been great, but the fact that, like email and other forms of more modern communication, it’s asynchronous. So I can publish when I want, they can listen when they want. And I love that. And you know I’d say, on average on publishing, once a week, once every week and a half maybe. But it depends on the show. Some shows don’t get published too often at all and some are very regular – a couple of times a week. So am I getting knocked down in the iTunes algorithm for not publishing on like every Wednesday for example?

Dave Hamilton: I was gonna say I don’t think so, but really my answer is I don’t care.

Jason Hartman: You don’t care about me?

Dave Hamilton: Well, I think it’s more important to care about what works for your listeners and cater to that and then you will maintain and grow listeners. You’ll lose some – there’s gonna be attrition in the process – but you want to grow some. And the trick is maintaining consistency, because while you can publish when you want and they can listen when they want, the world, by and large, we run our lives on schedules, right. So if people know that they listen to Speaking of Wealth or Mac Geek Gab every Thursday morning on their way to work or every Tuesday afternoon at the gym, that’s their thing, right? And so if they get to the gym on Tuesday afternoon and they don’t have the most recent Mac Geek Gab episode, they’re still gonna work out at the gym and they’re gonna find something else to listen to. Now, if that happens once, that’s okay. But if it happens 3 or 4 times or if your show comes out at such an erratic schedule that they can’t work it into their weekly schedule, then that consistency for them gets lost and eventually a good chunk of those people are just not gonna listen, not that they don’t want to but they can’t fit it into their lives in a repeatable way. And so that’s why I really encourage people – even if you record 4 shows – I mean for what you’re doing, for the most part the information is not so timely that it has to come out right away.

Jason Hartman: It’s not a news show, yeah.

Dave Hamilton: Bingo.

Jason Hartman: And that’s one of the other great things about it – no big pressure.

Dave Hamilton: Yeah, right. But if you can get one show out on regular basis each week, from what we found, that works much better for maintaining and building a listener base.

Jason Hartman: Okay, so it’s more about the listeners than it is about iTunes, because a lot of people – and I think this is a big area, it’s certainly a big area for my companies – we all have heard of and talked about and maybe hired someone to do search engine optimization for us, right, for our website. But iTunes SEO, if you’re a podcaster, I mean that’s huge, or if you’re an audiobook publisher or a musician with music on iTunes, SEO within iTunes itself is critically important.

Dave Hamilton: It is and good luck figuring it out.

Jason Hartman: Yeah, okay, well thanks a lot. Yeah, I thought you were gonna offer some hope here.

Dave Hamilton: I can tell you what I know about how things work behind the scenes at Apple. The first thing you have to remember is that podcasts don’t make Apple any money. So there are some great people working on the podcast team at iTunes but there aren’t’ many of them. And so a lot of what happens in iTunes is automated and then they do have their staff picks to highlight shows and this, that, and the other thing, and they’ll pick a genre and then highlight that, and they do a good job with it. In order for them to even consider picking your show, though, it has to meet certain criteria and some of that criteria is very technical – you have to publish your feed in a certain way so that they know that it’s gonna look good when they feature you. You have to have your artwork be JPEG or PNG image of 1400 pixels square. So they have published a spec document – make sure that your show fits that 100%.

The other thing is iTunes does not track downloads. They track subscriptions. So the charts where you see the top shows, those are the shows that people are subscribing to, not the shows that people are downloading because people don’t download from Apple. They download from you. Even though they’re using iTunes to do it or another client, it’s going direct to your site, to your servers. So Apple has no real way…I mean they have some metrics and they’ve gotten better, but just the way the infrastructure’s built, they just can’t do it. They don’t have that data. So making sure your listeners subscribe inside of iTunes, making sure they give you good ratings inside iTunes – the more frequent you get new reviews posted from listeners in iTunes, the better your chances of sort of lifting up above the fray. But it’s a very difficult way to discover podcasts. Yeah, word of mouth is better.

Jason Hartman: The day iTunes starts allowing podcasts to advertise by the featured show section, I will throw money at them.

Dave Hamilton: We all will.

Jason Hartman: That’s just so critically important to be found in iTunes. And with podcasting it’s really so organic. I keep thinking of ways that I’ve done business over the years. Can I just throw some money at this and make it go faster and grow bigger and faster? Not so much, huh?

Dave Hamilton: Not so much. You’re right, it’s very organic. It’s this very grassroots thing. And stuff like you and I are doing here, this is gonna benefit both of us because your listeners are learning about me and of course, because you have me talking here, I’m gonna tell the people that follow me, hey, I just talked to this guy – you might want to listen to my interview and then they like you and they go listen to other stuff you’ve done.

Jason Hartman: Yeah, I know. It’s very good that way – the viral component is definitely there, so that’s a great thing. Okay, anything else you want to mention about podcasting?

Dave Hamilton: No, I’m good. We could talk about microphones, but we can move on.

Jason Hartman: Technical stuff is not…It’s pretty easy to do. I had thousands of dollars’ worth of sound equipment – still have it sitting in a box, SLR microphones and all of that stuff. And, honestly, do you know when I’m talking to you on right now? And I think for the balance of practicality, simplicity, that’s what I like – simplicity. I’ve got a $50 iRig microphone that’s noise cancelling – it plugs into the headphone jack of my Mac – I’ve got a MacBook Pro Retina that’s fast and solid-state – and Skype call recorder, $20. I mean, come on, this is not hard.

Dave Hamilton: Nope. That’s right.

Jason Hartman: But I used to have a whole studio and mixer boards and the whole bit and, I don’t know, it is better – I’ll give you that, but I think it’s a marginal improvement considering portability, convenience. When I’m in Europe and I want to record and do a show, the simplicity of this setup is just beautiful.

Dave Hamilton: I agree 100%. Yeah, simplicity can win out as long as your sound quality is above a certain level. And yours is – you actually sound pretty good. I mean it sounds like you’re speaking into a $50 mic which is what you’re doing.

Jason Hartman: Thank you very much.

Dave Hamilton: There you go. But you get mic technique. I’m not hearing your room behind you bouncing around which I get with a lot of people that use those $50 mics, right? So because you owned thousands of dollars’ worth of stuff, you probably learned a little bit about how to use it. And that translates to what you’re doing right now.

Jason Hartman: Yeah, fair enough. Well, hey, everybody wants to know about Apple mostly, except those non-Apple users, so I thought the last worldwide developers conference was really a bit of a disappointment. I mean they announced a new OS, but it’s not here yet. It’s gonna come out in the fool. They announced the new…What is it, their most powerful machine, the desktop one?

Dave Hamilton: The Mac Pro.

Jason Hartman: Yeah, the Mac Pro, that’s not here yet but we’re gonna come out with one. I mean I don’t know – I’m getting a little worried about one of my favorite companies.

Dave Hamilton: Obviously, I’ve been following Apple for a long time – first as only a fan and then when we started publishing things it became more than that, but WWDC is this weird thing for Apple because the show is for the developers. But the keynote becomes this huge media event. But most of the time what they announce at that show is geared towards the developers. And it is really important that Apple have a relationship with their developers because if their developers don’t know about the new stuff that Apple is coming out with – and Apple balances their secrecy here of course, but they need developers to start several months early developing their applications for something like IOS 7 or OS X Mavericks so that when Apple releases those OSes, it doesn’t take the developers by surprise and suddenly all their apps don’t work. They came out with two OSes this year at WWDC, right? IOS 7 and OS X Mavericks.

Jason Hartman: And for the phone, right.

Dave Hamilton: Yep, one for the phone, one for the Mavericks. And they have to tell developers about those early, but because it’s Apple and we all watch them so closely, they have to do it as a press event, otherwise the information will leak out in ways that Apple doesn’t like and blah, blah, blah. So, yeah, I can see from the end-user perspective that being a disappointment. Because it’s like, oh, this looks great, I want to touch it. And, in fact, no you can’t touch it yet – it’s only for this select group of people. So, yeah, I can see that.

Jason Hartman: Okay, so what do you think is next for Apple? I mean I just think they need a real homerun soon. They gotta do something sort of amazing.

Dave Hamilton: Yeah, you’re not wrong. I think we’ve got this event, the rumors are pointing to September 10th. I honestly don’t have any direct confirmation from Apple on that one way or another, but I think that’s probably right based on what we’ve seen out there. What will they announce then? I think they’re gonna do one event this fall. Last fall they did 2, right, they did an event for the iPhone 5 in September, and then about 6 weeks later, in October, they did the event for the iPad Mini and the iPad 4 and the whole iPod lineup for the fall and for the holiday season. This year, though, I don’t think it’s gonna be an iPhone 6, I think it’s gonna be the iPhone 5S and maybe this iPhone 5C which is this lower-priced version of the iPhone, something like that. My guess is they’re not gonna do one event just around speed-bump type upgrade for the iPhone. So I think we’re gonna get the retina iPad Mini at this event and perhaps some other things too. Now, the real question is, if they do all that in one event, are we gonna see this watch this year or this wearable thing?

Jason Hartman: And I’m worried about the iWatch concept. Wearable computing, I believe in it, I can’t wait until I can use it myself, but how are you gonna take a picture with a watch? Youo know, it’s probably gonna pop out like a little iPod Mini does now or whatever that one’s called, but I don’t know. I just don’t know.

Dave Hamilton: The watch reminds me a lot of the iPad itself, because Apple certainly wasn’t the first one to market a tablet, right? I mean, there were many, many people before them and it never really caught on. The tablet thing just didn’t exist in the public consciousness until the iPad came out. And Apple, to their credit, they waited – remember, the iPad was designed before the iPhone even. They developed the whole touchscreen and what eventually became iOS for the iPad. And once they got that inertial scrolling happening, that’s when they said wait a minute, as the story goes, Steve Jobs said, wait a minute – this could work on a phone which was something else Apple had in there. So they put the iPad on the shelf and they took the whole thing and they made it smaller and then they released the phone and then years later of course the iPad came out. And I think the iWatch, if an when Apple releases it, is gonna be seen as the same type of thing, that Apple waited, they did it their way, they figured out how not to do it, they figured out how not to do it, they figured out how to do it and then rolled it out when they were good and ready. I hope that that’s what they do. I hope that they don’t try to race it out. Like you said, I mean, they do need a homerun. If they feel that that pressure is on them and they rush it out a year or two early, that’s not gonna be a good thing for them long term.

Jason Hartman: Well, I agree. We shall see. Anything else you want to mention on Apple?

Dave Hamilton: Can’t wait to get my hands on a new Mac Pro.

Jason Hartman: Yeah, for the real techie people like yourself, that is going to be an incredibly powerful machine there. Talk to us a little bit about your business of Mac Observer. I mean building traffic, getting loyal blog readers and so forth – any tips and things like that?

Dave Hamilton: Yeah. The thing that we remind ourselves every day, and it is easy to lose focus of this, is that we want to publish content – in a broad sense, we want to publish the site that we want to read. And it’s really easy to lose sight of we could just publish that and it would grab a lot of eyeballs and get a lot of traffic, and sometimes we wind up doing that, but those readers are not sticky readers. They are fleeting views – you get something posted on Reedit or Google News or any one of the kind of high traffic aggregator type sites and it’ll pour traffic at your site for a little while and then it goes away. And it’s good for keeping your name out there and all of that good stuff, but really, I’ve mentioned passion with podcasting, it’s the same thing with writing content for the web, too. You just have to publish stuff that you believe in and that you can look back on 3 years later and say, yeah, I’m glad I wrote that, not looking at it and saying I’m glad about the eyeballs I got from writing that – you want to say I’m glad I wrote that. And that will keep and build that loyal audience.

Jason Hartman: Yeah. Any things on site design or do you ever do any contests or things like that? I’m not much into contests but I kind of think I need to be. But it seems like there’s an opportunity there – I don’t know – maybe some might consider a little bit hokey.

Dave Hamilton: No. You and I both need to do more of them. Yeah because, you have to remember you’ve got this audience that, in some way, feels like your show is partially theirs, right, or your blog or whatever it is. If they’re coming back regularly, they feel that that’s partially theirs. And you want to, A, reward that, but also, B, encourage other people to think that way. And contests in that sort of ancillary engagement I’ll call it, comments and forums and all that stuff that’s about the content obviously is good to have, but also that ancillary engagement where you’re saying, okay, this is what we do, but let’s have some fun too now that we’re all here together. And yeah, contests are definitely part of that.

But also selling t-shirt or selling mugs, whatever it is, that kind of thing helps people feel a bond. No one is more invested in someone else’s success after they have spent money to prove their loyalty to that person or product.

Jason Hartman: Yeah, very good point, very good point. Hey, since it’s so in the news nowadays, I thought we could get some free techie and security advice for our listeners and you were gracious enough to share that – this is going to be valuable, folks. But we all know who Edward Snowden is now. He’s living in Russia and he’s got a year there I guess as a reprieve. We’ll see what he ultimately does. But he’s the guy who exposed our government spying on us, and on one hand I kind of think he’s a hero, on the other hand I’m not sure if there are any true legitimate national security secrets that he exposed – I obviously wouldn’t support that. But, whatever the case and wherever he stands, we know about the NSA now and what they’re doing. And we know that privacy and the constitution is being trampled all over. I mean, I think everybody would agree with that on both sides of the aisle.

Dave Hamilton: I certainly would.

Jason Hartman: Yeah, definitely. And so there’s a lot of talk and interest now in securing one’s communications. And one part of that is the ability which I think is fairly easy to encrypt our emails. And we talked about that just a little bit before we started and you knew all about it, so I wanted to ask you about that.

Dave Hamilton: Yeah. So it has been possible to encrypt your email for years. And, in fact, Apple’s built-in mail client with OS/10 and with iOS has the ability to both encrypt and decrypt your email. Right there, what you need first is you need a certificate. And you can actually get a free one. A company called Comodo will provide you with a one year certificate for free, and then you can go and create a new one each year and renew it until they stop offering it for free and then somebody else will.

I’ll give you the link so that you can put it in your show notes so people don’t even have to hunt, but if you just hunt for “Comodo Free Email Certificate” you would find it. You go there, you sign up, you put in your email address, you put in some information. Comodo is a trusted security certificate vendor. So they are able to say, yes, this guy is who he says he is, and when you attach that certificate to your emails, people get this note or indicator I should say. What their email is saying, yes, it’s Dave Hamilton that signed this email. Once they have your signature that comes along with what’s called your public key – and this is where things get really interesting – you get 2 keys when you get this email certificate, and the good part is mail will just take care of this magically for you once you have your certificate.

Jason Hartman: Apple Mail.

Dave Hamilton: Apple Mail will, yes.

Jason Hartman: But what about non-Apple mail users and then we’ve got mobile devices with email and then we’ve got the website – say, for example, you use Apple Mail as your email client, but then you’ve got Gmail behind it. And Google has been completely rather open about how they don’t care about our privacy. They’re gonna share everything with the government and everybody else, advertisers, etcetera.

Dave Hamilton: Let me very quickly finish with the 2 key thing because it’s key to understanding how this works. So, when you go get your email certificate, you get 2 keys. You get one that’s your private key that you don’t share with anyone, and then you get a public key which you share with the world. That public key only allows me to encrypt data and it won’t allow me to decrypt it. Once I’ve encrypted data with that public key, even I can’t decrypt it, only you can decrypt it using your private key. So it’s great – you send me your public key, I want to send you an email. I type the email, I say encrypt this with Jason’s public key, you receive this encrypted file as an attachment to your email and then you decrypt it with your private key, and as I said, Apple’s mail client on both Mac and iOS will use these keys that you can get from Comodo and it’s transparent. It just automatically decrypts it once you’ve installed the key and it works great.

Jason Hartman: So the person on the other end, it depends what email client they’re using. I can just see this turning into a giant hassle.

Dave Hamilton: It is.

Jason Hartman: It is? Okay, great.

Dave Hamilton: Yes and no. Outlook and those sorts of things also support these public keys. It is a standard. It’s not Apple proprietary by any stretch. So it’s pretty easy to make these S/MIME keys work across all your email.

And you mention Gmail, let’s say you have a Gmail account and I sent you an encrypted message and you logged into Gmail to see it, you would just see an attachment. You would not see any text. You would see that you got an email from me, so the sender and the subject are not encrypted, but the text of the message is and it’s just an attachment. You could then download that attachment and decrypt it locally or there’s add-ons for Firefox and those sorts of things that’ll try and manage that for you better inside Gmail. But there’s a problem with this whole thing and the problem is where we started. It’s that Comodo has generated these certificates for, in this case, you. We don’t know if Comodo takes that private key and shares it with anyone like, say, the NSA. So it’s entirely possible that we could have this encrypted email exchange that the NSA has the keys to unlock.

Jason Hartman: Right, yeah.

Dave Hamilton: That’s where something called GPG tools comes in. And this may actually be even easier on everything but your mobile device. If you to GPGTools.org, you download it for your platform and they have it for OS/10 and every other platform, too. And this is a 3rd party thing that runs for OS/10 and it hooks right into your email, and you generate your own keys. So the only place that private key has ever existed is on your computer. And, that way, you know you’re the only one that can decrypt it. But I’m not so sure how GPG Tools is gonna work with mobile devices and so you may not be able to decrypt messages there.

It’s funny you mentioned it because just yesterday, John Brown – John’s my cohost with Mac Geek Gab – and we were talking about GPG Tools, we said, yeah, we gotta dig into this with iPhones and see how it works and then you asked me about it today.

Jason Hartman: Yeah, that’s funny how that works. But when someone endeavors to do this, do you just decide, hey, there’s a couple of people, like maybe my accountant for example, or my mortgage rep…

Dave Hamilton: Or your bookie.

Jason Hartman: I don’t have a bookie, thankfully.

Dave Hamilton: I know, I couldn’t resist.

Jason Hartman: But encrypt with them only and then everybody else is just normal email communications.

Dave Hamilton: That’s right, yeah.

Jason Hartman: Okay, so you can do that. Besides the NSA, I mean, let’s go beyond that, do you need to worry about someone intercepting your emails? How can that be done? Or is that an important concern?

Dave Hamilton: It is. It’s actually less of a concern than it was years and years ago. It used to be, when you sent an email, it hopped through a dozen machines to get from where you were to the server that I would go check. Nowadays, you put your email up on the mail server that you’re sending out, that talks directly to the server I’m gonna receive at and so there’s not a lot of people kind of in the middle there, but there are people in the middle there, and it is entirely possible. That traffic looks very predictable, and so you could say I just want to sniff email packets. And you could even say I just want to sniff email packets for emails sent to Dave Hamilton. And if you’re able to kind of get in there, you could do that.

Jason Hartman: But can they do it from our homes or offices or only from like a public Wi-Fi at a coffee shop for example?

Dave Hamilton: Yeah, so public Wi-Fi obviously makes it easier, but if someone is inside your office, they can definitely do it without question. In fact, it’s probably very, very easy for say your network administrator at your office to sniff your personal email packets as they’re on their way out to whatever mail server you’re choosing to use.

Jason Hartman: But nowadays, people are using cloud-based systems anyway. I mean, Google is your network administrator if you’re using their suite for example.

Dave Hamilton: And you just need to decide how much you want to trust Google.

Jason Hartman: Yeah, well that’s a good question. By the way, listeners, I did a show on that with the author of the book entitled Search and Destroy and it was about Google’s abuses, so they make everything wonderful and convenient and they have awesome products – I use them – but you should know the other side of that too, that’s all I’ll say.

Dave Hamilton: No, that’s right.

Jason Hartman: You should know what you’re getting into for sure. But Dave Hamilton, thank you so much for joining us today. Tell people where they can find you and learn more about all the awesome stuff you’re doing.

Dave Hamilton: Sure. So you can find me on Twitter @DaveHamilton, you can find Mac Observer at MacObserver.com and that should get you to where you need to go.

Jason Hartman: Fantastic. Dave Hamilton, thanks again for joining us.

Dave Hamilton: Thanks for having me, Jason. This is awesome.

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Narrator: This show is produced by The Hartman Media Company, all rights reserved. For distribution or publication rights and media interviews, please visit www.HartmanMedia.com or email [email protected] Nothing on this show should be considered specific personal or professional advice. Please consult an appropriate tax, legal, real estate or business professional for individualized advice. Opinions of guests are their own and the host is acting on behalf of Platinum Properties Investor Network, Inc. exclusively. (Image: Flickr | yyq123)

Transcribed by Ralph


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