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Dennis Kennedy

Dennis Kennedy is an award-winning leader in applying the Internet and technology to law practice. A published author and...

Tom Mighell

Tom Mighell has been at the front lines of technology development since joining Cowles & Thompson, P.C. in 1990....

Episode Notes

What lurks in the dark corners of the internet? Will you, as a lawyer, ever need to access the dark web on behalf of a client? In this Kennedy-Mighell Report, Dennis Kennedy and Tom Mighell discuss the need for lawyers to have a basic understanding of the dark web – both its uses and dangers. They give an overview of the types of content that exist on the dark web and caution lawyers to utilize experts when navigating it for their clients. Also in this episode: Dennis and Tom discuss the Gartner Top 10 Strategic Technology Trends for 2019.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for the answers to your most burning tech questions.

Special thanks to our sponsors, ServeNow and TextExpander.


The Kennedy-Mighell Report

Illuminating the Dark Web



Intro: Web 2.0, Innovation, Trend, Collaboration, Software, Metadata… Got the world turning as fast as it can, hear how technology can help, legally speaking with two of the top legal technology experts, authors and lawyers, Dennis Kennedy and Tom Mighell. Welcome to The Kennedy-Mighell Report here on the Legal Talk Network.


Dennis Kennedy: And welcome to Episode #225 of The Kennedy-Mighell Report. I am Dennis Kennedy in Ann Arbor.

Tom Mighell: And I am Tom Mighell in Dallas. Before we get started, we would like to thank our sponsors.

Thanks to TextExpander for sponsoring our show. Communicate Smarter with TextExpander. Gather, Perfect, and Share Your Knowledge. Recall your best words instantly and repeatedly. Learn more at

Dennis Kennedy: And we would also like to thank ServeNow, a nationwide network of trusted, prescreened process servers. Work with the most professional process servers who have experience with high-volume serves, embrace technology, and understand the litigation process. Visit to learn more.

In our last episode we talked about our presentation on cybersecurity for collaboration tools at the recent College of Law Practice Management Futures Conference, some thought our perspective was a little pessimistic, let’s say. In this episode we decided to go even darker and try to shine a light on the dark web. Did you see what I did there, Tom?

Tom Mighell: I did.

Dennis Kennedy: What’s all on our agenda for this episode?

Tom Mighell: Well, Dennis, in this edition of The Kennedy-Mighell Report we will indeed be discussing the wild west of the so-called dark web. What legal professionals and others need to know about this little-known part of the Internet.

In our second segment we’ll talk about Gartner’s latest top 10 strategic technologies for 2019, and as usual, we’ll finish up with our parting shots, that one-tip website or observation that you can start to use the second that this podcast is over.

But, first up, the dark web; like most things the Internet has many facets, not all of them are well-known or even particularly good, one of these less known parts of the World Wide Web is what we’re going to be discussing today, the dark web, where all sorts of good, but also disturbing, probably illegal and dangerous things go on, not a place we’d want to visit, but definitely a place we all need to know about.

Dennis, what in the world got you thinking or interested about this topic?

Dennis Kennedy: So I saw this blog post by Chris Hoffman on the How-To Geek Blog recently, and that was called, ‘What is a “Dark Web Scan” and Should You Use One?’ And it got me thinking about the dark web. First of all what it is and then the tools that you might need to access the dark web and what might be out there.

And he talked about it in the context of having your data compromised and your information, Social Security Number, credit card numbers other things like that, being out, it’s stored and available on the Internet in this sort of secret, not well-known place generally known as the dark web, and this cottage industry that’s grown up around the dark web saying that we can go out and search it and find out whether your data is out there.

So, it’s just got me thinking a lot about the whole notion of the dark web and as we look at what people talk about hackers and all this information out there and all these bad things happening of state actors, organized crime, all sorts of different things happening on the Internet sort of below the surface in this area called the dark web.

It made me think this is something that probably we all need to know a little bit more about it even though as you said, Tom, I’m not sure it’s a place that any of us needs to visit for fun. We may have to that’s important or have someone visited for us if certain things happen. But I also thought it was an interesting topic to put through our technology competence analysis framework.

So, if lawyers have an ethical obligation of technology competence then I think that dark web is one of these topics where you say for lawyers is this a relevant technology that a lawyer needs to keep abreast of and I think it’s always interesting to ask that question about new technology, and something like this the dark web, which is a very old technology.


Tom Mighell: Well, and I think that the answer to that question, although we probably should ask this question maybe again at the end of this segment. I would argue that most lawyers who represent clients and if we think mostly in terms of family law or criminal defense knowing about what the dark web is, what it’s capable of, what can be done, I think is extremely important.

Depending on the type of law you practice, depending on what you do, it may be less important to you and your practice, but I think that at a minimum lawyers understanding what it is and what its capabilities are, what you can do, why you should stay away from it, all of those things I think are going to, as we discuss, are things that all lawyers should at a minimum have some knowledge of to do.

But I think maybe what we want to do first is let’s distinguish. I think we’re going to do a formal definition of the dark web in the second, but let’s first distinguish it from what other people may have heard and I’ve been at several conferences where people have, I would say, “mistaken”, but that’s probably not a fair word to use, mistaken the dark web for the deep web. You may have heard and I remember at least on this podcast and certainly on my blog for years, talked about the invisible web and talk about how that’s different.

Now what we consider to be the deep web or the invisible web is what we would consider to be the part that is not searchable by search engines, that’s not indexed by Google or other major search engines.

So, I would think that most government databases, anything that you need a password to get into, to search, to get information from Google and other search engines, they get stopped at that door and they can’t get in and search it either. So that’s part of the deep web.

I think the estimates right now are that search engines can really only index somewhere around 4% of what’s available on the Internet, so that’s I would call that mostly the deep web and then I think really kind of where the comparison goes is, is the dark web part of the deep web, because it’s likewise not accessible via a search engine, it’s not indexed in the same way and the way that you get to it is considerably different as we’ll talk about in a minute from actually accessing the Internet.

Am I heading down the right road, Dennis? Do you want to maybe give a definition of kind of what the dark web is or what we’ll be using for this episode?

Dennis Kennedy: Yeah. I always think of the dark web is this sort of probably a very small subset although it certainly gets a lot of attention in the news, but a small subset of what we call the deep web or the invisible web and some people would say that Facebook is one classic example of deep web, it’s a non-searchable part of the Internet but it’s definitely not part of what we call the dark web.

So, as in all things let’s go to Wikipedia for the definition. They say the dark web is the World Wide Web content that exists on dark net so that’s this sort of nefarious area of the Internet. Then they overlay networks and they use the Internet but they will require specific software configurations or authorization to access.

And so I think that is a notion, so typically you are not accessing the dark web through your standard browser and you’re not using Google or other search engines, so there are certain characteristics, it’s definitely going to be hidden websites where you may have to have certain knowledge or certain credentials to even know that these things exist. They’re not accessible by the standard browsers, you may need a special tool, and generally, you’re using this area of the Internet anonymously, very anonymously for a variety of purposes.

So, it’s beyond like where you’d say the deep web or the invisible web you might need a username and password, this is really a more anonymous part of the world. And I think that for me, Tom, as I look at the dark net, I think that non-browser access and probably this — I don’t know it’s fair to call it a browser tool, but there’s definitely a tool called Tor, that I think is probably key to our thinking about the dark web.


Tom Mighell: Well, that’s right. I mean, I think that you’ve kind of described it the right way that the characteristics are — it’s not something that wants to be found easily, although the dark web uses URLs and maybe not exactly traditional web addresses, but there are addresses to get to sites, there’s no guarantee that those URLs are going to stay the same from one day to the next. They change frequently, you’ve got to have that level of information.

And Dennis, as you say there are a couple of ways to access the dark web, probably the most common is using Tor. Tor is known as The Onion Router and when you’re using Tor you are in what is known as Onion Land and the reason for that is that there are those who would compare the dark web to an onion.

There are a number of layers that you have to navigate and get from one layer to the next before you can actually get to where you’re going, and for that reason getting into the dark web can sometimes be slow. The connectivity is not always good in that area, but you have to have a special tool.

In a minute I’m going to kind of walk through the steps to take if you want to do it yourself and really how complicated and how many steps it takes to really do it in a way that’s safe and effective, but I think the bottom line is all of these tools, Tor, there’s a couple of others, Freenet, the Invisible Internet Project and they are all using IP addresses that have been masked so that you can operate anonymously, and so the desire is or design from this is that the tools that you have allow you to be anonymous although I think that we’re going to need to kind of point out that just because you’re using these tools doesn’t necessarily mean that you can stay anonymous on the dark web, which is part of the dangerous aspect of going online which is you can still give quite a lot of information about yourself to people that you probably wouldn’t want to see the information if you don’t take care of yourself when you venture out onto the dark web.

Dennis Kennedy: So, let’s talk a little bit about there is actually some — what I’ll call the good uses of the Darknet and they relate to anonymity. So, it’s a place where whistleblowers can share or release information or communicate with the press or do other things and do it anonymously and safely for them. If people are being censored, it’s another outlet for them if they’re protesting or they’re working against government authorities it’s another place that could use. So any place where anonymity is important for accomplishing what I’ll call good works, the Darknet can be invaluable in that.

However, most it’s called the Darknet for a reason and it’s generally considered a bad place, and Tom, on Wikipedia they list eleven types of uses for the Darknet and most of them are not good things, so let’s talk about what the Darknet is most commonly known for, and probably, I think that starts with the most famous example which is Silk Road if you want to talk about that.

Tom Mighell: Well — actually I don’t want to talk about that, I want you to talk about that. So, let me step back for a minute and say, one of the interesting things that I learned preparing for the podcast that I really wasn’t aware of is I was aware that obviously you can be anonymous on the dark web. What I didn’t realize was that actually the United States has something called the US Internet freedom agenda, which allows people who are in countries that have repressive regimes, that don’t allow you to express yourself, like you say, Dennis, it might censor you or otherwise try to arrest you, allows you to access information that might otherwise be unavailable to you because you happened to live in that country.

I also didn’t realize that there’s actually a different version of Facebook. It has its own version on the dark web that you can access and get to for those who are unable to do that. So I found that very interesting that there are many ways in which the dark web serves good purposes, but I think, more to get along the lines of what you’re talking about and although I want you to talk more about Silk Road, I mean, just some of the those eleven things that I can think of off the top of my head are that you can use the dark web to sell drugs or buy drugs, you can buy guns, there is human trafficking that takes place on the dark web.


Certainly one of the major uses of the dark web is stolen credit card numbers, lots of stolen identity information. Child pornography, I think it probably goes without saying, there’s quite a lot of that. I think one of the things that you’ll see a lot out on the dark web are data dumps from data breaches. I think the Ashley Madison data breach is one example of where a lot of the information from that was all put on to the dark web, so that people could go through and get passwords and other types of information. I think that’s how a lot of the people who are clients of Ashley Madison got threatened is people were able to access it on the dark web and use it for whatever means that they could come up with.

So, Dennis, you want to talk a little bit more about the Silk Road?

Dennis Kennedy: Yeah, so the Silk Road was probably the most famous example and people can dig into more details if they want, but basically the idea was created this online marketplace called Silk Road, where basically anything goes in — or anything went and you could buy and sell anything and from drugs to weapons, to hiring hitmen, so the stories were amazing, so it was like everything that you would be afraid of in your worst nightmare about the Internet and it was kind of rolled up and shut down, but it gave people a flavor of what might be out there and what might be possible and I think that’s — if you have an idea of what the dark web is it probably comes from the reporting around Silk Road and as Tom said the stories of what you can find out there are amazing, but a lot of it is that identity personal information and the concern is all out there and it could be purchased, also the tools you can use to break in the networks can be made available there or purchased there, so all sorts of different things can go on and then there is that notion — like I said, it’s like every nightmare that anybody would have about the Internet can probably found on the dark web or — so we’re told, I mean, obviously there’s not a lot of data and there’s not a lot of mapping of the dark web.

So, there are a lot of risks, but I also think that what people discovered is that a lot of these things, our scams, their hoaxes, their ways to trick people who think they are buying some other identity information, they are giving up their own identity, there are obviously lots of money scams, you should typically involving Bitcoin. So it is a very wild place that probably if you don’t know what you’re doing at all, you’re more than likely just to be completely ripped off.

Tom Mighell: Okay, so we’ve been talking about a lot of the reasons why the dark web is not a good thing, why there are a lot of bad things out there, I think that for the purpose of lawyers knowing this just to know that it exists and it’s out there, that’s a good thing, but are there ever — I think we probably should talk about are there ever occasions when a lawyer would need to access the dark web on behalf of a client? What would some of those circumstances be, Dennis?

Dennis Kennedy: We typically would think of is if you wanted to find out whether passwords or accounts or identify — identification information had been compromised or released, you say if I did a search and I found that Social Security Number or credit card numbers those sorts of things were out there and available and especially if they were being sold, that could be useful in any number of cases or representations.

I think to the extent that you find the tools that somebody could use to get on the Darknet as part of your regular discovery or forensics identification, it should tip you off that there could be some other things going on and it may give you some indications that are or follow up on some suspicions you might have that somebody is using what I’ll just call hacker tools because you can tell that they at least downloaded them from the Darknet, so those are probably the ones that come first to mind for me, Tom.


Tom Mighell: Well, no, I agree. I think those are generally the reasons why a lawyer wants to access the dark web but I think that I personally can’t think of any good reason why a lawyer would want to access the dark web on their own. I have no desire, I mean, even though I may have some type of morbid curiosity like I would want to watch an automobile accident or something like that to be able to go out and see some of this stuff. I really — I mean just hearing about all the things that can happen to you when you connect a computer to the dark web are pretty much enough for me to say, if I were a lawyer and I needed to get to this information, I would be hiring someone immediately to do it for me and not to do it myself.

And so I kind of was to demonstrate that, I consulted who I usually do when I want to talk about security and things like that, talk to our good friend Sharon Nelson and John Simek and they kind of provided a good list of here are the things that you need to do to access the dark web.

So, you’ve got to first utilize a dedicated computer, it’s got to be its own computer dedicated to access in the dark web, you have to create a virtual machine on that computer so that you can access it. You’ve got to make sure that your operating system is patched, there can’t be any flaws in it, it’s got to be the most recent version of your operating system.

You have to be able to make sure that the administrative access has changed so somebody can’t take control of that computer. When you access the dark web, you need to make sure you’re using a network that’s not connected to any way, shape or form to your network, make sure that you’ve got security software that’s installed. We talked about using that Tor browser tool to be able to access it, so you’ve got to install that. You’ve got to use a VPN before you connect to it. All of that just seems to argue to me why do this yourself? And then there is other rules, don’t transmit personal information while you are out there, don’t print anything, don’t open any downloaded files while you are connected.

All of this to me suggests if you’re going to use the dark web, make sure you get somebody who knows what they’re doing and can lead you through it safely.

Dennis Kennedy: Right. And so, I think that’s the notion where we say there are the white hat hackers who can help with this stuff, and so, I think that you would want — you typically looking where there would be some indication that something that you had been — that you are working on either could have been compromised in information released to the dark web or that your client or somebody else involved in the matter that you were working on was accessing the Darknet.

As Tom indicated earlier, probably access to the Darknet, it’s going to be based on what statistics they have, it’s going to suggest child pornography, and maybe a few other things. It could be that there’s a lot of stolen intellectual property, so people might access movies, music and stuff like that, probably less of that, it seems like a really complicated way to do that.

But I’m with Tom that this is probably not a place that you want to go. It sort of reminds me of like some high school kids saying like, oh, I have this great idea. I’ve found somebody who works for the Mafia, and I’m going to buy dope from them and like they collect money from their friends and they go and they get scared out for their life and the money taken away from them, they end up with nothing and you go like, who could be surprised about that.

So I think there is that notion where you’re going to be involved in this or need to be involved with the dark web. You 23:54 have somebody holding your hand who knows what they’re doing or probably you want to just pay them to do it for you because, Tom, you’re basically talking about setting up like almost a clean room to access it or a very clean computer, and I’m with you.

I will probably buy a Chromebook and that would be the only thing that I would use it for, and it would be a weird situation because that activity in itself is going to look very suspicious to anybody who sees it.

Tom Mighell: And I guess that’s as good a place as any to end this segment. Let’s take a quick break for a message from our sponsors.


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Tom Mighell: And now let’s get back to The Kennedy-Mighell Report. I am Tom Mighell.

Dennis Kennedy: And I’m Dennis Kennedy. It’s Gartner time again. This time the well-known tech analytics company has released its 2019 Top Strategic Technology Trends. While learning to use the tech, we have today right in front of us is obviously incredibly important.

I have always believed that having an awareness of what tech trends and the big tech trends that are out there, heading our way is something that we just can’t forget about and it’s — I just think it’s vital to pay attention to. So the Gartner lists are always a good resource on this front. Their strategic tech trends for 2019 give us a good snapshot of some of the biggest of the big picture trends.

Tom, what struck you as particularly important on this list?

Tom Mighell: Well, I have to say two things about it, the first thing is strategic technology, I’ve got to be honest, has never interested me as much as the practical applications of that technology. So I look at this list and I have to tell you that I don’t think a list of technology has ever made me feel so dumb. There were so many things on this list that I either felt I didn’t fully understand or that I really had never even heard of.

For example, never heard of the term Digital Twins before, that’s on the list. I went and looked it up to see what is digital twinning, which is defined as the digital representative of a real-world entity or system. So, I assume it is taking and making a virtual version of it, so that you can work with it, if there’s a problem with that real world system then you can manipulate it in the virtual world and come up with solutions for it.

Interestingly, this has been a thing since 2002. So I am not sure why it’s just becoming a trend in 2018 but there it is. I do like the idea of smart spaces as a trend. I like the idea that they’re calling it smart spaces because it feels like it’s moving and recognizing that the idea of the smart home or the smart office, it’s expanding that there are more places that can be smart.

And so the idea is that there are spaces out there whether it’s a personal space or an office space or a business space or a public space that can become smart, I really like that idea. I would argue because I like to talk about ethics so much that one of the most important ones on the list as boring as it may sound, is digital ethics and privacy, technology is taking more-and-more information from us.

And the ethics part means, it’s important for us to be able to trust the technology that we use and the people who make that technology need to be able to instill trust in us to use that technology that they’re doing the right thing because otherwise, we’re not going to use it. They’re not going to be successful.

So, I think that’s one of the major trends that I’m seeing — that I see on that list that interests me and I think is important.

Dennis, I know you have completely different things from the list that were interesting to you.

Dennis Kennedy: One of the things I really like is we can look at these lists, the ones that interests you most are like always the ones that are completely the opposite, the ones that interests me. So, I mean, to go with a list, I mean there’s a couple things that are pretty obvious, Internet of Things, AI, although I think the spin on AI is kind of interesting. So that they’re talking about AI being used sort of collaboratively in development of software, which I think is really interesting.

So to pick out the ones that I liked to talk about augmented analytics, so I think there is this notion that I would call it sort of like cloud of analytics or data analytics as a service. So do we get some smartness built into analytical tools and make them easier to use and then use them on a per use basis? I think that’s super-interesting.


There’s a notion of the empowered edge and I think there’s this ebb and flow between sort of like smart at the center and dumb out at the outside in networks, and so, I think that because of the processing power and the other things that we have out there that the sort of devices connected to the Internet can have more power and capabilities built into them, which takes some the burden off the whole network, so that will be important in Internet of Things. Blockchain of course, and these days people are so — they’ve so had it with blockchain and in some ways I’m happy to hear people say that because there’s so much going on there that I think it’s so significant. I’m glad that people who think they know everything are not paying attention to it, because they’re missing some important things.

And then I think the one that’s out there on the radar, probably about five years is interesting because of its — especially if its security implications is quantum computing because the quantum computing works the way that people think it can, it puts a lot of the approaches that we have to encryption and other security of methods at high risk. So, I think watching the developments in that area is going to be super-important.

So now it’s time for our parting shots, that one-tip website or observation that you can use the second this podcast ends. Tom, take it away.

Tom Mighell: So, the only thing that makes me unhappy about my parting shot this week is that it is not a Google Assistant skill, but it’s an Alexa skill. There’s a whole new set of actually skills that Alexa has put out called Skill Blueprints and what it does is, is that it allows you to basically create your own customized skills to things.

So, for example, you can put together a chore chart that will let the people in your household know what chores need to be done. The reason why this is so interesting to me is, is that my dad is getting to the point where he’s forgetting a lot of things. I like the idea that there’s a skill that you can use to basically ask Alexa to remind you, tell me what things I need to do before I leave the house each day, or tell me what things I need to do to get the house ready when it’s going to be freezing weather.

There’s a skill for a house guest. Welcome your guest to the to the house with a guide on your home in your neighborhood where they can ask easy questions and get back answers that you give to it. I think it’s really fascinating that you can start customizing the information that Alexa gives you. My only hope is that Google can come up with something that mimics or is similar to this, because I think it’s a really useful tool to have and it’s free to use.

Dennis Kennedy: Yeah, I really liked this one too when I heard about it, Tom, and it’s something I’ll probably play with, but the guest thing was especially cool. The guest could say like where are the guest towels and things like that and you could customize this whole experience for people.

So, yeah, it’s really fascinating. Although there was this part of me that said, I wish you could do a skill that said, where did I leave my keys? But I realize that’s sort of beyond the capability of Alexa at this point.

Tom Mighell: Yeah, it’s not going to help you in the moment of where you left something, but it can, both Alexa and Google, can remind you of certain things. If you want it to say, remind me what my spouse’s anniversary is and it will tell you what it is. So, you can actually train it to remind you certain things. It’s not going to tell you where you put things in the moment, but it’s getting smarter every day.

Dennis Kennedy: Well, and also you could have the guest ask, when the guest asks what’s the Wi-Fi password/ It would be great to just have Alexa rattle that off for them. So, yeah, I like that parting shot, Tom.

So, I have something that’s based on the class I’ve been teaching at Michigan State and I’ve just grown to like the two tools that we’ve been using to look at business models and to turn business ideas into actual action and to move them forward, and they both come from One is the business model canvas and the other is the value proposition canvas, and these are — these are some of my favorite tools where you start to — once you use them and you say, wow, everything looks like I can use this tool with.

So, Tom and I want to figure out like how to promote our book better. We’re going like, oh, we could just use the business model canvas and figure out the components of that promotion project or a new business or whatever.


And so, I really like that, and then the value proposition canvas is super-simple, and it puts your focus right on the customer or the user of what you’re doing and it says, what — what do they hope to gain if they make a change in what they’re doing and what are the pains they are hoping to remove and then you can look at your product or service and say what pains does it remove, what gains does it deliver and see how it matches up, and then you can kind of shape your product or service.

So, really simple tools, graphic, visual, but they really allow you, they really give you a lot of insight. So highly recommend and I am really enjoying working with them with my students.

Tom Mighell: And so that wraps it up for this edition of The Kennedy-Mighell Report. Thanks for joining us on the podcast. You can find show notes for this episode at

If you like what you hear, please subscribe to our podcast in iTunes or on the Legal Talk Network site, where you can find archives of all of our previous podcasts.

If you like to get in touch with us, you can reach out to us on LinkedIn, on Twitter, most of the social network venues. Leave us a voicemail though. We still love to get voicemails, we can feature your question or comment on our B segment. That number to call us at is at (720)441-6820.

So, until the next podcast, I am Tom Mighell.

Dennis Kennedy: And I am Dennis Kennedy, and you have been listening to The Kennedy-Mighell Report, a podcast on legal technology with an Internet focus.

If you like what you heard today, please rate us in Apple Podcasts and we will see you next time for another episode of The Kennedy-Mighell Report on the Legal Talk Network.


Outro: Thanks for listening to The Kennedy-Mighell Report. Check out Dennis and Tom’s book, ‘The Lawyer’s Guide to Collaboration Tools and Technologies: Smart Ways to Work Together’ from ABA Books or Amazon, and join us every other week for another edition of The Kennedy-Mighell Report, only on the Legal Talk Network.


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Episode Details
Published: November 16, 2018
Podcast: Kennedy-Mighell Report
Category: Legal Marketing
Kennedy-Mighell Report
Kennedy-Mighell Report

Dennis Kennedy and Tom Mighell talk the latest technology to improve services, client interactions, and workflow.

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