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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

Time to get organized! Dennis and Tom are moving along to the next phase of their Second Brain project—taking their captured data and deciding how to best classify and catalogue it. With easy, effective data access in mind, they talk about their preferred organizational structures, hash out their tendencies toward both apple-pie order and thinly veiled chaos, and examine the tools they think will be most helpful to their unique sensibilities.

In their second segment, they ponder the apparent revival of email newsletters. As many writers have moved toward launching independent, subscription-based newsletters in 2020, this formerly passé medium has suddenly found new popularity. Dennis and Tom discuss the viability of this shift and their thoughts on the pros and cons for this type of content.

As always, stay tuned for the parting shots, that one tip, website, or observation you can use the second the podcast ends.

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

Special thanks to our sponsors, ServeNow and Colonial Surety Company.

Mentioned in This Episode

A Segment: Second Brain – Organization, Part 1

B Segment: Newsletters are Hot Again

Parting Shots:


Kennedy-Mighell Report

Second Brain Project: Organization, Part 1



Intro: Web 2.0, innovation, trends, collaboration, software —

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: Welcome to episode 274 of the Kennedy-Mighell Report. I’m Dennis Kennedy in Ann Arbor.

Tom Mighell: And I’m Tom Mighell in Dallas. Before we get started, we’d like to thank our sponsors. First of all, we’d like to thank Colonial Surety Company Bonds and Insurance for bringing you this podcast. Whatever court bond you need, get a quote and purchase online at

Dennis Kennedy: And we’d also like to thank ServeNow, a nationwide network of trusted pre-screened 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.

Tom Mighell: And we want to remind you that the second edition of our book, ‘The Lawyer’s Guide to Collaboration Tools and Technologies’ is available on Amazon. Everyone agrees that collaboration is essential in today’s world but now more than ever, knowing the right tools is going to make all the difference.

Dennis Kennedy: And as I like to say at the start of our recent podcasts, actually all of them for 2020, “What a difference another week or two makes. And the big changes just keep rolling along.”

In our last episode, we went all in and I mean all in on virtual reality and the Oculus Quest 2, which we both love.  In this episode, we return to our big Second Brain Project and bring you an update as we focus on a new part of the Second Brain. Tom, 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 returning to our second brain project to give you an update on our progress and hit the next step in the process. In our second segment and under the category ‘Everything Old is New Again,’ we’re going to discuss the latest new content sensation, The Email Newsletter seriously 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, we want to give you an update on our Second Brain Project. In the first two episodes, we covered what we think is the first step to creating a Second Brain and that is capturing the information that’s important to you. If you want to catch up, if you haven’t listened to those episodes or want to refresh your memory, go back and listen again to episodes 265 and episodes 268 of the podcast.

But now it’s time to cover the next step in the process, which is organization. How do we take what we’ve captured and organize it so that it’s useful to us? So, Dennis, how do you want to approach and divide up this segment?

Dennis Kennedy: I was just realizing, Tom, as you said that the whole notion of organization just really makes me anxious. I mean, it’s like the most difficult thing for me. So. I’m thinking two parts here and I’m not sure I have quite the right words but I call one structure and so that would be tagging, naming, files and folder conventions, things like that. So, sort of the things that take place underneath what you’re doing and are maybe the structures that you put things into.

The second would be the interface. What is actually the interface or the tool that you use to access that information. When I was thinking of it earlier today, Tom, I was thinking that if you look at a document management tool, this to me is sort of my analogy here, that you’re doing documents and there are some things that are happening sort of underneath that document management tool when you create a new document. So, there’s metadata, there’s other things being captured, names, those sorts of things that happen and then you access those documents and so you find things and work with them in the actual document management tools so that could be world docs, net documents whatever, so that’s sort of the two parts that I see.

So, I don’t know, does that make sense?

Tom Mighell: Oh, it does! No, it makes perfect sense for me. I mean, first I think that when you’re selecting a way to organize it, you first have to decide how you like to organize your information, how you prefer it to be organized and we’re going to kind of get into a little bit of the details there in just a minute and then once you’ve decided what you like, you have to find the interface or the tool I guess, those two words we’ll use interchangeably that best supports your view, that best supports the way that you like to organize that information. And I think we’re going to talk about some of the options there as well.


Dennis Kennedy: And then I’d say the other thing I sometimes think about this is there’s the invisible element and the visible element or maybe even the automatic elements, so things that just happen and then something that’s more intentional but I don’t really want to dive too deep into that but it’s a way that people might start to think of these two parts.

So, I think the first thing you always look to and this goes back to the earliest days of using computers, actually managing any kind of information because the metaphors are paper-based, which is sort of folders, categories and tags. And that’s something I’ve always struggled with because I have a habit of falling out of those systems and then the evolution of what I’m doing starts to make a lot of those systems less and less relevant, so it becomes harder and harder for me to find things and harder and harder to understand which folders, which tags and things to use. So, we’ll touch on this. So, sort of in my Second Brain notion, the tagging and a lot of these things should happen automatically, but we’ll talk about that later.

So I don’t know, Tom, I always have — so my notion of if I went onto your computer, which you would never allow me to do but I just sort of picture that there would be all these folders that were neatly organized and labeled and you could find everything at the tips of your fingers with all these cool categories and tags, so I could be wrong on that but what is your view of the files and folders in this this sort of structural layer?

Tom Mighell: So, in my line of work, information governance, when we talk to our clients about email, we kind of divide email users into two different categories. You’re either a filer or you’re a piler. You either like to have things organized into folders or you just like to keep it all in the inbox and use that search tool or use the filter or use some other way to find that information.

And I think that to a certain extent, we can divide most people with information management into one of those categories, at least preference-wise. You are correct. Well, you are partially correct. I am a filer. I tend to think of things in a hierarchical fashion. I like to think of a place for everything, everything in its place. But here’s the thing and here’s where I think figuring out what works best for you is where it gets hard and where I’m skeptical of your automatic approach.

When you find a note that you want to save, let’s say that you find an article on a legal topic that is relevant to things you’re working on right now. Do you save that note into a notebook with legal articles? Should it go into a notebook for the project that you’re currently working on that relates to it? Should it go into a notebook with research that you might want to go to in the future because it might be relevant to a client’s case in the future? Should it be all three?

I might want to use it in so many different contexts. I think it’s hard to know what one precise place to put it and so, frankly, I think that what you should be thinking about when deciding how you want to organize this information, one way to make that decision is the less you can predict how you’re going to use the information, the more flexible the system you’re going to need to organize it. The more you can predict how you’re going to use it, the less flexible, the more organized that it can be.

Now, as we’re going to talk, I am kind of a goldilocks kind of person and I’m finding that I kind of like something in the middle there and we’ll talk about that at the end of this and in the next podcast, we’ll talk a little bit more about how I work that. To me, those are the things you have to think about when you’re organizing thing is what use do you plan to make of it in the future and how do you want to get to it. And you have to be thinking about what future you is going to decide with this and that’s not always an easy thing to guess at this point in time.

Dennis Kennedy: Yeah, so a couple things really resonate for me their time, so one is oh my god, I am a total piler as opposed to a filer. And then I think there is that future you notion where that’s where I start to stumble and then how am I going and the idea of what is that future use going to be. So, let me just give you a quick example. This evening, before the podcast I watched a great presentation on open source software and actually the maintenance aspect of open source that was done by the Long Now Foundation.


It was fabulous. But if I were going to file that or a reference to that, then I’m kind of thinking, well, does that go under open source is a legal topic? Is it under open source software? Is it what I think will become an important topic for me in a couple years of maintenance? Or does it go into the file folder or under a potential class I might develop for law school or some other things?

And so, that’s where I really stumble because when I’m at the point where I want to file it, I feel like there are all those choices in front of me and we’ll talk about the automatic thing I think in a little bit. But what I found is that I end up with the system that I’ve described in the script as thinly veiled chaos. But if you look at what I do, I just decided the best thing for me to do is I just have folders that go by the year. Intense, everything that happens during the year, I throw it in. I used to have something I just called research, threw it in there and I’m like, “Hey, I’ll just do things by year and I’ll do search over it,” because if I have to make a decision early on, I can’t do that. It’s just become too difficult and that’s why I’m looking for something that would be automatic and we talk about some of the approaches. I’ll give some examples of — there are tools that do this automatic tagging that I think will be helpful.

So that’s my current approach. Tom, I am actually and I think the audience will be interested in some of the things you’ve learned with your work in information governance and how that translates to your own approach because I know you would never advocate — did anybody use the system I’m using?

Tom Mighell: Well, I mean if we’re going to go to my business of information governance, I’m going to tell you that in general, auto classification of information is still not there. It’s still not where it needs to be. We’ve had several clients who’ve developed their own auto classification tools, so we came in an audit and even after we said that we thought that it was reasonable, their legal department still said, “Nope, too many opportunities for false negatives or false positives so we’re not going to adopt such a tool.”

And so, I’m very interested in this notion of automatic tagging that you have and I really want to get into this but if we look at my approach, frankly, I’m not a very good organizer of information even though I organize, my folders on my OneDrive are organized by category and topic. I used to be a heavy Evernote user and I was mostly a heavy Evernote user just to grab anything that was important to me and put it in there and I would put it — I had a probably a couple hundred notebooks, I would tag stuff. But to be real honest, I didn’t really ever go back and use it. It was just kind of — in fact, when I moved to what is now my new tool, I wound up not even keeping any of my Evernote stuff. I just got rid of all the Evernote stuff and I started over completely from scratch, which was how little I thought of my past efforts at organization.

Dennis Kennedy: Yeah, so I think that sort of each path leads to its own set of frustrations and so, if I look at how I’d like to go forward, I’m intrigued by we’re both experimenting with the tool called, which is a bookmark manager. One of the things I like about it is that if I go to bookmark a page, it’s sort of automatically suggesting some obvious tags for it and I can just click on the ones that I like. So it’s almost like a prompt and I go, “Yeah, not exactly but it’s close enough,” and will help me find something and maybe over the long run, that will turn out to be useful to me but the concept is that what it’s giving me automatically is better than the nothing that I would do for myself.

And so I sort of say, as we move forward with this sort of promise of machine learning and things like that, if those systems suggesting the tags can do a better job of that, that’s interesting and then also, in some ways if they would do that without making me click on the ones that I want and I would just go like, “Hey, I think I can live with what they have. I think that’s helpful to me,” and it’s taking that step where I have to make a decision sort of out of the loop because then it’s forcing me to say, “Oh, do I really want to save this bookmark because then I’ve got to figure out how I organize it and I don’t really want to do that. I want to move more quickly.”


So that’s sort of one of the places I’m leaning and then I’m also trying to make that that infrastructure part of it like the file folders, the systems and nested stuff. I would like to make that invisible and not anything I have to think about or do much on.

Tom Mighell: So, I’m intrigued here about because I use it as well. We both use it. It’s my go-to bookmark manager now and once again, I’m a total filer there because I put things into folders and I access them that way. But here’s my question, so let’s say that you look up three articles on machine learning that you want to look at. I’m really intrigued to know, is it always going to recommend tags that are similar so that you can tag them because what I worry about with that auto recommendation of tags that by the end of three months from now, you’ll have seven million tags because they come up with something different based on whatever they’re reading on the page and I may need to go and try it out myself to see is it suggesting common tags for common content because that’s really what’s going to be the magic for you is making sure that whatever it automatically does, it’s accurate and it gives you the right tag every time.

Dennis Kennedy: Right and I think it comes down to as we think about algorithms, machine learning, and those things, you just want to go like, “Hey, at some point, hey LinkedIn, if you’re suggesting these are people I might know or I might want to connect to, I’m willing to trust your opinion.” “Hey, Amazon, if you say other people who bought this also bought this, that’s fine. I’ll look at it. That’s helpful to me.”

Tom Mighell: Yeah, but the difference is is that with this information, you’re going to need to come well — the question is are you going to be able to come back to this information when you need it the same way that you might need to go back to that person on LinkedIn when you need that and say I need somebody who is affiliated with x, y, or z. Is this the same value to you because it’s like I want to see everything on machine learning. Here it is on this page or in this folder versus on LinkedIn, I want to see everybody who knows about machine learning and where are you going to find that? I’m assuming there’s a way to search for that type of information but to me, it’s not immediately obvious.

Dennis Kennedy: Yeah and so I think that I should go to use and that’s sort of like the end stage of the Second Brain is you like to say, “Okay, when I go to turn this into –,” what I call work product for — is it a good enough way to describe it for now. And I go, “Okay.” Let’s say I tag a bunch of stuff open source and then the decision I make is that I do want to develop a class on open source license law for law school, then what I would like to do is to say, “Let’s use that tagging to pull together everything to this smaller research folder,” that I know it’s an acceptable trade-off for me if I can pull all that stuff together, then I can do some more sifting once I’m in there and it’s going to be kind of an over-slice and that’s acceptable to me.

Other people, it wouldn’t be. You’re going want to have to say like, “No, I would want just the stuff that applies to the creation of class because I had put some thought into that earlier.” So again, it’s like the filer/piler sort of thing. So I’m like I know when I go to use something, I’m comfortable with the over resourcing it to say, “Okay, here are all these things,” and I’m going to have to do some sifting at that point but I can do a better job at that point.

And so, that I think gets us to — to me, I think there is this interplay that we’ve been touching on between search and organize and not to date ourselves, Tom, but I think that it goes back to sort of Yahoo! versus the search engines. I think that you could have lived in the early days on the Internet in the Yahoo! world where everything was like really categorized and you could like go to exactly what you wanted and everything was all neatly organized, but there got to be too much stuff and you just went to search. So, I think I still feel there’s too much stuff even for me personally, so I lean toward the search side versus to say, “Oh, here’s this nicely organized library,” and I go pull the book off the shelf that I need.

Tom Mighell: And I obviously lean more towards the organized side but I also and will demonstrate when we talk about kind of the interface and the tool that we’ve selected, I think that it is good to be flexible so I think the system I’m going to choose is going to have the best of both worlds.


It’s going to have the possibility for organization, but also the capability of search that can get you if the organization is not exactly what you want it to be. So is a great tool but it’s not going to be your Second Brain. It’s not going to serve as what that is. So maybe it’s time that we talk about some of the options, some of the tools that you should consider when becoming your Second Brain. maybe talk about some of the pros and cons of those tools and then maybe do a big reveal at the end of what we’ve chosen for each of our Second Brain interfaces. Do you want to get started with some of the tools? You want me to get started? How do you want to do this?

Dennis Kennedy: Yeah, why don’t you start because you think in terms of sort of three categories or three sort of competing areas and I’d like to have you sketch that out because I think you have an interesting take on the nuances between those.

Tom Mighell: So, yes. And I want to be very clear that we’re talking about personal knowledge management here. There are tools that can be used for team knowledge management that are corporate wide, that are law firm based and none of these are what I would think of as being suitable for your firm practice except under very interesting circumstances.

I do divide these up into three different sort of areas because I think that they all approach knowledge management and a Second Brain from different angles. The first I would say are the straightforward notebook apps: Evernote and OneNote. You probably all used to using one of them. We’ve talked about them a ton on this show before. I have been both an Evernote and a OneNote user. I enjoy using both of them but they are a very straightforward organizational process. You create notes and notebooks, you can tag them with topics, it is not flexible at all. If you use something belongs in multiple notebooks, you’ve got to make a copy to make it work. I’d rather have one version of the note accessible in multiple places and that’s kind of a pain to organize that. It’s just now that I’ve kind of looked at other things, I sort of feel like Evernote and OneNote are great, but they’re very linear. They’re very static in their organization and they are basically for, like I said before, the people who are more predictive in what you’re going to need it for. If you know where you’re going to need it and how you’re going to want to use it, then a tool like Evernote or OneNote is for you.

On the very opposite end of the spectrum here, I’m going to place some tools that I don’t think we’ve talked about on this podcast before. One is called Roam Research and the other is called Obsidian. They are similar tools that work together. They are similar tools in relationship to each other and how they work and I would say that they are the very opposite of organizational.

Roam Research describes itself as a note-taking application for networked thought. And I want to talk real quick about what networked thought means in this context. I think the idea is really great. It’s designed to help you connect thoughts and group them together as they might be related and be in multiple places at once, which means that within a note, you can create links to other notes and move among and beyond them to see the connections between those notes.

So, let’s go back to the example of the legal article that you found. Let’s say you’re doing research on a family law topic. You found 5 or 10 articles you want to keep. If you add those articles to Roam, you can just type in somewhere in that article, you can type in the right and I’ll call it a tag, it can be a code, it can be whatever you want to call it, you can say it’s a community property. You can type it in at the top of each article and automatically, another page is created with links to all the articles that you just added.

So, let’s say six months from now, you’re going back to write an article on community property for a bar journal, all you have to do is go to that one page and you can see everything related to that topic. I think it’s pretty amazing how it works but I also have to admit that it is extremely overwhelming and confusing to me because I think it’s so lacking in organization. It’s basically opinionless on what you do with it. And so, it’s hard for me to really know what to do with it at all. The people who are using it are very smart people. I struggle to learn how to do it and so in the end, I really want to learn about using Roam, but I am going to go with a tool that I can best wrap my brain around and that’s something with some level of organizational structure, which leads to our last category, where I think doesn’t really belong in the Evernote-OneNote category, it’s not really in the Roam Research category and that’s Notion.

Notion is hard to describe because I think it can be a bunch of different things. You can use it for task management, project management. You can use it as a repository for documents.


I think that could be a drawback that it is so many different things. But I think for my purpose, maybe Dennis for your purpose, I’m going to describe it as a place where you can save notes, take notes and create databases that will link your notes to other areas and other databases so you can create that level of network thought, and this is why I don’t understand why you like Notion, Dennis, is it’s more organizational. It’s got more structure in it than something like Roam.

To me, it’s a good balance of organization with flexibility. I will talk more about this as we get to the next podcast, but I also can link to that information to other workspaces. I can organize it into workspaces. If it’s connected and relevant, it’s all there to me. I think you’re seeing where I’m headed with what my choice is and that’s my basic overview of those three tools. I’ll shut up now, Dennis, thoughts on those? Any further things to add?

Dennis Kennedy: Yeah. I mean, I think that for our listeners, these are the three categories to think about and we’re going to come to different places typically on these things and sometimes for different reasons.

I’ve used Evernote and OneNote for a long time. I would just say something is a little bit missing there for me because it’s never caught on for me. I use it. I collect things in there. I typically don’t pull stuff out of it in a way that’s really useful to me but they’re great tools and for certain uses and I would say OneNote especially, if you’re doing legal research and those types of things, I could see it could be exactly the right tool.

The Roam Research and Obsidian thing, and I thank Tom for not pointing out that I have an objection to Roam Research because their automated email note, when I applied for the beta, was just seemed really snotty to me so I vowed never to use it, something to think about when you do customer experience. I think that makes sense if I were doing a lot of academic research where I would call like footnoted articles and things. That’s where I see and then I’m taking a lot of notes.

So, for me, I joked around with Tom once where we were talking about this and I pulled out notes from a call that I had made earlier that morning and I said, “Here are my notes.” And I actually read four words to him, so like note-taking for me to use the Roam, Obsidian family of tools, I would have to have more discipline and a different approach to taking notes. So that would be the distinguisher and then I come to Notion and what attracts me and part of it is because of the potential, because there’s a lot of development going on and there are templates and you can kind of plug things in to do certain things. So, I like that, so there’s a lot of action around it and activity.

It’s also very visual to me and then I’m going to talk about something in the way that you can connect things in time, describe this and I know some people who like Notion, but they don’t like my description. It really seems like a Wiki to me and has the advantages of a Wiki with a more graphic approach and a more modular approach so I can see how I can connect things, move things around, rename things, pull things together. And so, of the three choices I’d like that, but part of it is the visual. It’s also I think all of these, you can just claim as cloud-based so you can use them on whatever device you’re on, which is another important factor.

So, that’s how I see the pros and cons, Tom. And I think that probably there’s some similarities in approach but I’ve sort of committed at this point to going with Notion although I’m going to explore Obsidian potentially as something to use and I may use OneNote as a transition tool for certain things where there’s not a way to pull things directly into Notion yet. But I would expect those to happen.

I would say the one drawback about Notion that I’ve run into with some of my friends who are very graphic and do mind mapping and stuff is that you can’t do the whiteboarding and stuff right now but it’s on the roadmap. Like I said, with Notion, you’re kind of looking out a year or two to see what it will be. That’s an important thing for me.

I’d also say that the Roam and Obsidian to me feel really techy to me. Like you’re talking about markup language and other things like that, so that could be difficult for some users.

Tom Mighell: Two things about that: One of the what Dennis is talking about that some of this stuff around mind mapping will be available is is that until what is about to be very soon, Notion has lacked an API to connect with other apps.


Tom Mighell: A Notion has lacked an API to connect with other apps, but its API is scheduled for release any day now is what we keep hearing. And so, that’s very exciting. I think that when they’re able to plug into other apps, that’s when we start to really see what’s going to be interesting about it. In terms of difficulty, I would put it in between Evernote OneNote and on the easy side, and then I put Roam Research and Obsidian on the hard side. I would say Notion is not dead simple to learn how to use, but it’s also not too really hard to use it. It’s I think part of it is there are so many different ways to use it that figuring out the best way for you is going to be what’s important.

Now, we’re going to go into a deep dive in part two of this organized topic that we’ve got. So, let’s end the topic right now. Let’s stop Notion in very quickly. Any tips for our users on choosing an interface? I’m going to give two tips and then, Dennis, you can close out the segment. I’ll go back to what I said before. When you’re choosing the right interface to organize, you need to think first about how do you plan to use the information you keep? What is the future you’re going to need to make of that information? Do you need something that allows you to be more flexible in case there’s a use for the information you don’t know about yet or are you okay with it being organized because you know exactly what’s going to happen? I think that’s going to guide your way on figuring out what the best interface for you to use this. Obviously, I’m happy to talk about it more if you all want to give us a question for our B segment or just shoot us a message on Twitter or LinkedIn. Dennis?

Dennis Kennedy: Yeah, I think this is really jobs to be done stuff here is important. So, if you go back to our episode with Bob Mesta, where we really walk through that, but you really are thinking okay, what am I hiring these tools to do? What problem is the second brain going to resolve? I think your Notion of future you is really important and then to kind of figure out how it’s going to work in connection with the other things that you’re using. So, I think a lot of people could do really well as a starting tool with OneNote or Evernote. I think it’d be hard as you said. I assess the difficulty in the way that you do.

At a time, I would say if i were doing academic work with lots of footnotes, IE might gravitate toward the Roam Research Obsidian side, but Notion is kind of a nice middle ground for me right now, and I think we’re at the point in our project time where we’re looking to commit to some tools, and this one feels comfortable to me and it’s also I’m using it with a number of other people, which is another thing that will sway your decision on all of these tools because if you’re using it with somebody else, that is a big reason to give extra weight – you need to put extra weight on.

Tom Mighell: And there you have it. We will be getting to work on using these tools more carefully and catch up with us in the next couple episodes. We will continue this discussion on Notion with Part Two of our series on organization.


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Tom Mighell: And now, let’s get back to the Kennedy-Mighell Report. I’m Tom Mighell.

Dennis Kennedy: And I’m Dennis Kennedy. One of the hottest trends these days is believe it or not for pay email newsletters. So, people are talking a lot about a platform called Substack, an individual newsletter publishers making hundreds of thousands of dollars on paid email newsletters. So, email newsletter boom or bubble. Tom, what the heck is going on with this new trend and what do you think of it especially, for me, people like me who are trying to get email newsletters out of my inbox?

Tom Mighell: So, I would say first I would be very interested to know the exact number of people who are making lots of money from something like Substack.


I think there are people who are making hundreds of thousands of dollars, but I want to say that that’s a smaller group than are actually using the site, but I think there are two reasons why newsletters are so hot these days, and there’s one implication for me though anyway, which is one, these days there are so many sources of information trying to get competition for eyeballs is hard, and I think that one but it’s all in Twitter. It’s on blog. It’s in everywhere, but one place where I think you stand a better chance of capturing someone’s attention is in email. It’s where they look. You can get their soul attention there where everywhere else there’s noise. But to do that, you have to provide substantive, good, thoughtful content. The people are smart. They’re not going to subscribe a thing that doesn’t anything that doesn’t have a good content.

So, I think we started seeing a lot of newsletters come out that are kind of a revised source of information, and the ones I subscribe to are really good, thoughtful and have tons of content. The second reason, I think we’re seeing this at least this year, is the economy. I see a ton of journalists who are leaving their media jobs and saying, “I’m going to start a newsletter. I’m going to start charging people.” At least three people I follow at various tech sites have left in the past few months and they have started their own pay newsletter and, apparent by all intents, they’re being very popular.

You know, using a site like Substack, you can create your own newsletter. You can charge people to read it. I have a free newsletter on there. I don’t think that what I what I do on there is worth charging for people, and I think that a lot of people are starting to make some decent money. There are other tools by the way that do it not just Substack. There’s a tool called Ghost. There’s a tool called Buttondown. So, Substack is not the only game in town but, frankly, here are the implications.

Here’s what really worries me about it. It’s difficult for me because it can be quite expensive to follow the writers that you like because I’m following — you know, I found a group of productivity writers who have sort of grouped themselves together to offer five or six or seven different newsletters a week on productivity topics. I pay a flat $170 a year for that, and I really like the content. But, I’m not sure I want to pay for any more newsletters to anybody else because that’s — it can start to get very expensive, and it really start to add up. I sort of feel like this is the new streaming service because each newsletter you subscribe to, that’s another 10 bucks a month that you’re paying and it can all add up fast. Dennis, where are you with newsletters?

Dennis Kennedy: Geez, you know, I thought about doing my own paid newsletter for the last couple years, and I just decided against it because I don’t like email newsletters anymore, which seems like they’re people who just subscribe you, and then you’re always having to clear out your inbox, you know. So, the medium doesn’t make sense to me anymore. So, that’s part of it. There is all this content, and I think the email newsletters do offer this in this whole big ocean of content. They do offer curation and aggregation that has its value. I’m not sure like the $10 a month sort of thing makes sense as opposed to these sort of invisible or automatic micropayments, which might be a better model. But, we don’t have that as an option.

So, I think that’s tricky. I think that there’s so much as we like to call it fake news and all these other information. So, you’re looking for trusted sources. So, it could be that this is a flash in the pan because of 2020 that these things kind of hit. I’m also surprised it’s not video or audio that’s become hot instead of email newsletters. I guess the one thing that’s sort of interesting to me is it does offer a way to support the people who you like, which you are doing, Tom. So, which I think that’s a good thing. Then, also I think as you go to news sites, newspaper sites, and you hear all the media sites complaining that people aren’t paying attention to them and you go to their site. You get assaulted by their ads and all the other things that they do. There is something to be said for getting this email newsletter of content that you actually want where you don’t have ads and that has a certain value and maybe that is from $4 to $10 a month or two to $10 a month. So, I can see something there, but it is just sort of feels like a bubble before we move past email into other media.

Tom Mighell: Well, so I just want to respond to that because I’m not sure that this is a bubble and here’s the reason why because what newsletters feel like to me are they feel like a way to put it is, —


You’re receiving a blog post directly to you. I really think that RSS has failed to really catch on among those people. I mean, most people aren’t reading a news reader to catch up on the news and read blog posts. So, if you want to see what’s happening on your favorite blog, receiving it by email may be the way to get it done.

And so for that segment of the audience getting it by email and in my parting shot I’m going to mention, you don’t have to get them all by email. You can get them in different ways because email is a pain to have them in, but I really think that I don’t think that this is just of — what I’m worried more about is that somebody decides to purchase a tool like Substack and then charge for everything. You know, that’s Spotify or audible or somebody decides to purchase something like that and then charge for all of the newsletters that are in there and a subscription price for maybe making it like the Netflix of newsletters. I’m worried a little bit more about that happening because then the whole newsletter world goes crazy when that happens, but I’m more bullish on this at least for the next couple of years.

Dennis Kennedy: Yeah, and I guess there is a concern that it’s going to be a tool that seems like it’s something that’s going to support the independent writers and content producers like you and me, and it actually in turn drives us out. So, I think that is a huge danger. And the other point, you’re right, Tom. I just realized this that my experience of the internet, your experience is different than so many other people because you’re going like why would I want to email when I can get RSS? And, you know, I shifted some of the email newsletters I wanted to read to actually get them in Feedly, which is my RSS reader, but I realize that for a huge percentage of people using the internet, RSS is not anything that they use or understand. It’s time for our parting shots that one tip website or observation, you can use the second as podcast since. Tom, take it away.

Tom Mighell: Okay, I’m going to continue this topic very quickly in talking about newsletters by talking about some ways to consume them not necessarily in email. Dennis already mentioned one of them. The Feedly app allows you to subscribe to newsletters and you can review them that way. I have not been satisfied with that because I’ve not been able to make it work in a way that separates it from going through blog feeds and RSS feeds. It feels the same, and I need it to be different the way I consume newsletters. For a time, I was a subscriber to an email call an email service called I may have mentioned it on the podcast before. I ultimately left the email service, but one of the very cool features they have is something called the feed, and you can assign emails to the feed that become sort of your newsfeed. And I put all of my newsletters in there and then all I had to do was just click a button and there they were and I could just read them one after the other, read all those newsletters, and it was very pleasant. I just wish I liked the rest of the email service better.

But, what I am using now is an app called Stoop, S-T-O-O-P. And what Stoop does is it gives you your own email at You subscribe to your newsletters there, and then they just show up and it’s just a separate program for all of your newsletters. So, I can organize them by the newsletters I get. I can organize them chronologically. It tells me how long they are to read them. It provides them in a very nice ad free environment. It takes all of the ads out of the newsletters, which is nice, and it just makes for a much more pleasant experience. It’s free to use, but it’s also got a freemium plan for like $30 a year. So, it’s not terribly expensive, but that’s I think it’s either Stoop or Stoop Inbox. I’ll put the link in the show notes. Dennis?

Dennis Kennedy: So, I want to mention my new project, which is a course on innovation skills leading to prioritization in law and it’s at Check it out. See if it makes sense for you, and I also – Tommy, we’re talking and I’m not saying this is any of our friends who do this, but we’re talking about something that we see in Zoom meetings and, you know, people do some bad things in Zoom meetings that you read about, but the one that’s kind of funniest is that you have people on Zoom and they’re just showing like the very top of their head in the camera.

So, it’s like they don’t even check what they look like and it’s comical. So, I found this great little article by Sydney Butler on It’s called Seven Zoom Tests to perform before your next meeting, and there is just like it’s a handy checklist of the things you should do before a Zoom meeting just to make sure that you’re set up the right way, —


That you’re not on mute, those sorts of things, and it just makes you a better participant in any Zoom meeting that you’re on, so a really helpful set of tips.

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 on the Legal Talk Network’s page for the show. 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 shows along with transcripts. If you’d like to get in touch with us, you can reach out to us on LinkedIn or remember we’ve got a voicemail. Leave us a voicemail, so we can use your question for our B segment. That number is (720) 441-6820. So, until the next podcast, I’m Tom Mighell.

Dennis Kennedy: And I’m Dennis Kennedy and you’ve 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 podcast, and we’ll see you next time for another episode of Kennedy-Mighell Report on the Legal Talk Network.

Male: 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 20, 2020
Podcast: Kennedy-Mighell Report
Category: Legal Technology
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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