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March 15, 2021, 6 a.m.
How Jake Bernstein Uses Omni Software

On today's Omni Show, we welcome cybersecurity lawyer, Jake Bernstein. Jake is the former regulator for the Washington state attorney general, and currently practices with Focal Law. His work includes advice & counsel on everything from data breach and GDPR to the California Consumer Privacy Act.

Show Notes:

In this episode, we chat through Jake's journey to discovering Apple and The Omni Group. We also talk about his use of OmniOutliner and OmniFocus to keep his practice and caseload running smoothly. Jake also shares some tips that have helped him along the way.

Some other people, places, and things mentioned:

  • Browserwrap
  • Clickwrap
  • DevonThink
  • Federal Trade Commission Act
  • Focal Law
  • iThoughts
  • Jake's Twitter Account
  • Kourosh Dini
  • MacSparky
  • Mailmate
  • Obsidian
  • Omni Automation
  • OmniFocus
  • OmniOutliner
  • OneNote
  • Scrivener
  • The Cyber Risk Management Podcast
  • VMWare
  • Transcript:

    Andrew J. Mason: You're listening to The Omni Show. Get to know the people and stories behind the Omni Group's award-winning productivity apps for Mac and iOS. My name is Andrew J. Mason, and today we talk with cybersecurity lawyer, Jake Bernstein, on how he utilizes OmniOutliner and OmniFocus.

    Andrew J. Mason: Well, welcome, everybody, to another episode of The Omni Show. Today, we are so honored to talk with cybersecurity lawyer, Jake Bernstein, on his usage of OmniOutliner and OmniFocus. A little bit about Jake, he was the former regulator for the Washington State Attorney General, and currently practices with Focal Law. His practice includes advice and counsel on everything from data breach and GDPR to the California Consumer Privacy Act. Jake, thank you so much for joining us today.

    Jake Bernstein: Yeah, no problem. Thanks for having me here.

    Andrew J. Mason: So, before our interview, you actually mentioned that you're relatively new to this space overall, but how did you come across this ecosystem, and how did you come across Omni software?

    Jake Bernstein: Yeah, so for me, I came to Mac new, relatively recently. I think, as you mentioned, 2017 was the first Mac I bought. And it was not the first Mac I had tried, I had played around with previous versions of the hardware and software over the years, but frankly, I was actually rather anti-Mac for quite a while. I was a gamer, and Windows was everything, and it really wasn't until I got an iPhone, then left iPhone for Windows Phone, and then came back to iPhone when Windows Phone went away.

    Jake Bernstein: And I joke only sort of that what drove me to the full Apple walled garden was Microsoft killing my beloved Windows Phone. And I actually ended up getting a little iPad mini from a Christmas party. Talk about your white elephant gift exchange, with an iPad mini. And I started playing around with it, and I discovered, wow, there's a lot of... By this time, it had been years since I'd switched to Windows Phone, and I hadn't really been keeping up with iOS and all of the advances that Apple had been making. And I just found the iPad mini to be really, really fascinating with all the different software that it offered.

    Jake Bernstein: It wasn't even my first iPad. I actually had an original iPad, but it was quite a few years, really, between the original iPad and that iPad. It was actually an iPad mini 2. And once I got that, I was like, "Okay." I had a colleague in my law firm, and he was Mr. Mac, and he would constantly harp on me for my Surface and using Windows, and he'd be like, "You don't know what you're missing. You don't get it. You can do all this scripting." He's trying to convince me. And ultimately, it worked. It worked extremely well.

    Jake Bernstein: And what I started with was just a Hackintosh. I took my gaming computer, I got some VMware, and I loaded up an image of a Mac, and I started playing around. And the Omni Group software was actually some of the first software that I installed that was like, "Okay, I think I need to get a Mac." And it's really fascinating, because here's a really simple example of the difference between the Mac and Windows for someone who's new is you don't realize how special things like global keyboard shortcuts are until you realize that they're this thing.

    Jake Bernstein: And so, the Omni Group's quick capture in OmniFocus is something that maybe everyone in this community takes for granted, but we shouldn't, because it's really incredible. It allows your computer to do things that are not so application focused. I can be doing anything else, and I can have an idea, and I'm like, "Oh, I need to remember that." And I'll just hit my control, option, space bar, and boom, I can type it in.

    Jake Bernstein: And that is something that really drew me to the Mac, and probably spent about six to eight horrible months playing around with that Hackintosh before I bought the MacBook Pro, and haven't looked back since, really. Not even at all. In fact, I've gone so far the other direction, my desk has an iPad Pro, a HomePod mini, my MacBook Pro, an iPhone, I'm wearing an Apple Watch, and I've really gone all in, and it has paid dividends. We haven't really talked about it yet, but I think now's a good time to mention my career and how this all intersects.

    Andrew J. Mason: So let's hop over to your career trajectory for just a little bit, because I found it so fascinating. How does somebody end up becoming a cybersecurity lawyer?

    Jake Bernstein: So, it's a really interesting question, and it's quite a long story in some ways. I could start with it beginning with law school. And I don't mean just like, obviously, you have to go to law school. I mean, specific classes and even specific cases. Some of our audience will probably recognize the so-called browsewrap and clickwrap line of cases, but those are the law that allows you to create contracts online. And that was fascinating to me in law school, because everyone's used to thinking, "Oh, you have to sign something. You have to have a piece of paper," but there's all this law that basically goes into how you can make legally binding agreements with your mouse, and that's pretty fascinating. And that was 2004 that I first learned about that.

    Jake Bernstein: And so, fast forward, I'm looking for a summer job, and I end up at the Washington State Attorney General's office. And I really want to do consumer protection because of these cases. I found it really fascinating how contracts were formed and how that intersected with consumer protection issues. And what really evolved is that I got into the high-tech unit of the consumer protection division, and I was there for really the first eight years of my practice. And the thing about that is you have to somehow take a law that was passed in 1918, the Federal Trade Commission act is the basis for most of the consumer protection laws around the country, and apply that to the internet.

    Jake Bernstein: Obviously, you're talking about something that is just about a century before we even had this idea. And how do you do that? What does that mean? What does it look like? And the basic concept is unfair or deceptive acts or practices, they don't change. The concept is always the same, it's just the medium may change. And so, to bring this to cybersecurity, the FTC, which is the Federal Trade Commission, decided that cybersecurity is an unfairness problem. There's no specific law in the US that says you have to have cybersecurity. Instead, it says the Federal Trade Commission says that if there's a data breach and someone loses all of your data, that you've been harmed and there really wasn't much you could do about that, so that's kind of the essence of an unfair trade practice.

    Jake Bernstein: And because the job I was in was essentially enforcing what we call a baby FTC Act in Washington State, I got to start doing cybersecurity and privacy work sometime around 2013 and into 2014 and 2015. And there was no intent to do this when I went to law school, when I was in law school. Really, even the first several years of practice, it wasn't a thing. It wasn't something that anyone could think about. And what happened is that I started to see, I was always kind of a nerd, a techno-geek, and I started to see this is going to go places, this is really important.

    Jake Bernstein: Washington State, most people probably don't know this, but we passed one of the first anti-spyware statutes. Why? Because Microsoft wanted to do that and the legislature got on board with it. And the Washington State Attorney General's office used that law, and it was kind of the basis for a lot of the cases that I worked on initially. But eventually, we went past that, and man, I saw some cases where there was this anti-theft software for a rent-to-own company, and the employees would just abuse it. They'd be able to flip on the webcam, and I saw people getting undressed, they recorded it, they recorded screenshots. It was bad. Talk about a privacy violation.

    Jake Bernstein: And so, it was after that case wrapped up that I thought, "I'm going to have to go into private practice, because my wife wants me to get a real job." It's a joke, but it's so true. And, "What am I going to do? What am I going to do in private practice? I don't really want to just go be an insurance defense litigator. That would be boring. Consumer protection class action private work exists, but it's hard to get into."

    Jake Bernstein: And I thought, "I'm going to be a cybersecurity lawyer. And since that has literally zero meaning in 2015, I'm going to make it up as I go." And that really is what I have done. And so, my career has been leveraging the experience as a regulator into advising companies on how to maintain a reasonable cybersecurity program. And there's been some litigation on the side. I brought a case against a hacker who foolishly crowed from the rooftops what he'd done. And I have to say, it's been really, really fascinating.

    Jake Bernstein: Now, how does this all relate to Omni Group, and the Omni apps, and the Mac OS, and Macs? Well, let me tell you something. There's a big difference between being a government lawyer and being a private lawyer, and it is in the amount of work, the speed of work, the stress level of the work. And I found that when I left the state, my old system, and I use that with air quotes because there really wasn't one, just wasn't going to cut it. I got rapidly overwhelmed. I don't even remember. I think I was probably trying to use OneNote and they're built in to-do. I think for a while, I dabbled with Todoist, which is cross-platform. But quite honestly, none of it really worked.

    Jake Bernstein: And when I started fiddling around with that Hackintosh, and really listening to my colleague who kept telling me over and over to get a Mac, I discovered, "Wow, there's this thing called OmniFocus. There's this thing called OmniOutliner." And I thought to myself, "Man, why didn't I find this in law school? God, that would have been so much more convenient than taking notes in Word like I did." And at that point, the rest became history.

    Jake Bernstein: I just really dove in to the whole ecosystem and became enamored of the passion that the developer community and the user community has. I don't know if you all know this, but this is weird. This community of users, whether it's the podcast community, like Relay, or the Slack channel, where fans and users come and talk, this is not normal software development processes outside of the Mac community. And it's really, really special. It's been a pleasure getting to know it and know the people inside the community.

    Andrew J. Mason: Got it. So let's talk about your workflow. What does that happen to look like? I know you mentioned OmniOutliner.

    Jake Bernstein: Sure. So I do a lot of writing. That should come as no surprise. Lawyers do a lot of writing, and we write everything from a three-sentence email to a client, to multi-paragraph, but still relatively short form, advice memo, all the way to multi-section, 20 page briefs, and that's a lot of different styles of writing. And what I found, OmniOutliner is so great for is to basically just get the structure of whatever it is I'm writing down, and then I can take it, and one of the things I love doing is exporting an OPML and opening it up in iThoughts, or a mind mapping software, and then I'll play with it around in there.

    Jake Bernstein: Or sometimes, I'll go the other direction. Sometimes, I'll start with a mind map and then I'll export that into OmniOutliner, and then I'll flesh it out, and then I'll export that into something like Scrivener for the actual fleshing out of the writing. And once again, none of that exists in the Windows community, Windows world that I found. I mean, I certainly never found it in 25 plus years of using that software in a serious way.

    Jake Bernstein: And so, with OmniOutliner, this sounds silly, but if you've never used an actual outliner, people probably don't know what they're missing. The ability to shuffle around the lines in the outline, move them in, out, up down, this is basic functionality, literally OmniOutlining 101. But until you've experienced that, you don't know it even exists. And I think that's a real shame, because it's such a powerful software, and I think anyone who experiences it is like, "Oh, well, light bulb. This is so obvious in retrospect." But it just isn't.

    Jake Bernstein: If you don't have access to this kind of software, and what I like about the current world is that Mac seems to be taking off in a way that I'm not sure it ever has before. I think they're selling more, Apple is making more money on them, and the reason that's so exciting is that it means that companies like the Omni Group, their apps are just going to get a larger and larger audience. We haven't even talked about the iOS versions, but it's a good time to be a Mac fan, that's for sure.

    Andrew J. Mason: And then you mentioned using OmniFocus as well. Talk to us about that.

    Jake Bernstein: Yeah. So I've done all kinds of experiments with all sorts of different GTD apps, and ultimately, I always have come back to OmniFocus. My first version of it was OmniFocus 2, because I think that was a few years ago, and I haven't cycled away from OmniFocus at all in years now. And I use it for everything. It's not just for my professional life. I have a folder structure somewhat similar to folks like MacSparky and Kourosh Dini with areas of responsibility is the high level folders, and then it just gets more and more granular from there.

    Jake Bernstein: And the reason I do that is that when I've experimented in the past with using Apple Reminders alongside OmniFocus, I find that I just forget that Reminders exists. It's just not effective. If you're going to have one of these applications, you really should just put everything in one of them. There's a huge benefit to that. And others may disagree. Ultimately, this is very, very personal, but I think for me, that's what's worked best.

    Andrew J. Mason: Okay. So I would absolutely say that you've been on this path for a while. Do you have any advice for folks that are just getting started?

    Jake Bernstein: Definitely. Two words: fail forward. Really, it's about experimenting, seeing what works, seeing what doesn't work. And let's be honest. When you're learning this stuff, you're going to fail a lot more than you succeed. You're going to get frustrated. You're going to feel like this doesn't work. You're going to feel like, "Oh, this app isn't working, so I'm going to go try this other app." And that's fine. I think everyone needs to take their own journey on this path.

    Jake Bernstein: Now I do sound like some of the community luminaries who have recently been on this podcast, but really, the nature of task management and project management is fairly personal, and you shouldn't be afraid to just try it out and see how it works for you. I cannot emphasize the need for experimentation enough. There are many, many books written about OmniFocus. There are screencasts, there are whole podcasts dedicated to explaining GTD and how to use that concept. You don't have to be an expert. You don't have to record how-to videos in order to get something out of the software. You just need to try it.

    Jake Bernstein: And I think that there's no wrong way to try it. If all you do is use the inbox, that's fine. And I've heard others say this, and I'm just repeating it as someone who's gone through it in the relatively recent past. At the same token, there's common advice. Don't plan it out. Don't build out this whole structure in, for example, OmniFocus folder structure. Part of me agrees with that. I think experience has shown that that's good advice, but don't be afraid to try it. Go ahead. There's no wrong way. Ken Case isn't going to show up at your door and say, "I'm sorry, but you can't do that with my software." That's just not how this works.

    Jake Bernstein: Instead, build whatever you want, and you're going to know relatively quickly if it works. And I think, for me at least, I don't even know how many times, to borrow a programming term, I've refactored my task management system. One of the beautiful things about software is that you can do that relatively easily. At its core, OmniFocus is a big database and it doesn't really care at all how you use it or organize it. It will take whatever you throw at it and it will do what it's told. And I say, use that. Use that to your advantage.

    Andrew J. Mason: So you mentioned that phrase, fail forward. Do you have anything that you consider to be a point of failure or a sticking point in your system currently, or maybe where you tried something recently and you were just like, "Okay, oops. That didn't work."

    Jake Bernstein: It's happening right now. I'm kind of stuck with my tags, what tags to use. And this is kind of funny. At one point, I had this really complex tag structure where I differentiated all sorts of legal professional activities from review, to revise, to research, to write, to draft. I think I had write, draft, analyze, research, revise, all of these different tags, and I just, at some point, was like, "I spend more time figuring out how many tags to apply to this task than it might actually take me to just finish the task," and I stopped. I stopped doing that. I'm still not happy with my tag list, but it's way better and more useful to me.

    Andrew J. Mason: Absolutely. I think we have all been the victim of the rabbit hole where you just see something, and you're thinking, "Man, if this could make the difference, I'll just spend 10 minutes on it to see if this works," and then it becomes a thing. There's a difference between, "This is helping me go faster," and, "It's a thing."

    Jake Bernstein: It's so true. And defer and due dates, you can also get down this rabbit hole in the same exact way. You could carefully curate your defer dates if you want, but I think a rule that I've discovered for all of these systems is that if maintenance of the system requires more effort than what the system is giving back, you need to change the system. And in a way that's obvious. You're not going to do something to support some goal when doing that thing takes more effort and energy than doing the goal does.

    Jake Bernstein: And let's be honest, the community has Kourosh Dini, who's a psychiatrist, practicing doctor, and he will tell you, and as someone with ADHD who discovered it only into mid-adulthood, that it is really easy to pretend to be working, when what you're actually doing is shuffling chairs around on the deck of the Titanic. And in this case, the Titanic is OmniFocus, and the chairs are my tasks, and projects, and folders, and texts. And it doesn't do anything. If you do it too often, it becomes a form of procrastination. And that is something that you have to watch out for.

    Andrew J. Mason: Whenever we interview somebody new, we're always curious also about how Omni software fits in the rest of their personal application stack. So what other go-to software do you use day to day?

    Jake Bernstein: As an attorney, a lot of my work comes through email. We can't avoid it. I know there's all kinds of commentary about only check your email once or twice a day, stay out of that inbox, et cetera, et cetera. I can't do that. I have clients over the world, and so they have time zones all over the world, and so my email inbox is always active. I can't just turn off my email. So because of that, a lot of my work starts in email, and my current application of choice there is MailMate, which is about as nerdy as it gets, but I love it.

    Jake Bernstein: And I have got a very quick little automation setup. I just Ctrl+D when I've got an email highlighted, and what that does is it'll auto-populate an OmniFocus quick entry with the subject line of the email and a link back to that email in the note. Basically, I mean, so much of my work starts that way, with Ctrl+D in MailMate. And once that happens, it's sitting, waiting for me in my inbox, and I will go in. And I've been a real big fan of Hook recently.

    Jake Bernstein: I know, actually, the creator of the Hook app was a recent guest on this podcast, and he's pretty active in the community as well. He's a great guy. A lot of smart people in this community, aren't there? Rather over-educated bunch, aren't we? I find it very useful to invoke Hook on one of those tasks and create a note in Drafts. And this is not an uncommon, as you put it, application stack. It's funny to be a lawyer and not be a programmer or a coder and still realize, "Oh yeah, I have a tech stack." And they really do all work together. So the action in OmniFocus will get linked via Hook to a task in Drafts.

    Jake Bernstein: I haven't mentioned DEVONthink, but it's a major, major component of my practice and my organization system. It's hooked into my law firm's Google Drive backend. And all of that works together to surface the information for the tasks that I'm working on when I need it. And in terms of actually completing the work, a lot of stuff gets done with just that set of applications. I have to write an email back. I'll often start it in Drafts, and then I'll take it there. I've been using Obsidian a lot because it frankly just works well with the existing infrastructure I have. And then, when needed, when I'm doing long-form writing, that's when I pull out the OmniOutliner and the Scrivener and go from there.

    Andrew J. Mason: I don't always do it, but I'm so glad when I remember a catch-all question. You have a billboard to Omni software users. What do you say? What's the one thing you would share with everybody if you could?

    Jake Bernstein: Yeah. I think the Omni Automation functionality is really just getting started in what it's capable of. And I mentioned how this is very personal software, right? A system, so to speak, a GTD system is a very personal thing. It's awesome that we have the community members that we've already mentioned who are willing to spend time and put out books and screencasts. Those are great, incredible starting points.

    Jake Bernstein: But what you have to do is engage with the software and use it yourself. And the thing about Omni Automation is it allows you to take that personalization to the next level. I've often, I suppose you could say, bemoaned the lack of keyboard shortcut functionality in... As much as OmniFocus already has, there's always more that you want it to do. But with Omni Automation, you can make any keyboard shortcut you want for almost any function you want.

    Jake Bernstein: And at first I was like, "Oh man, I wish they would just do this so any user could just easily have a keyboard shortcut for this specific function." Then I began to realize, "Well, what if most people don't want that function?" How do you know? If you're the Omni Group, how do you know what functions people are going to want or need? But by creating the Omni Automation, you don't have to answer that question.

    Jake Bernstein: You can provide that functionality, the community will provide the functionality, and then anyone can set it up how they want. That was a very brave decision, I think, when you compare it to software like Things, which has some really great keyboard functionality, but that's what you're stuck with. It's limited. What the developers wanted is what you get. And I just think, keep creating, community. Keep going with all of the Omni Automations. They are a tremendous value add that I think very few other software development companies are doing.

    Andrew J. Mason: That is excellent. And I know we're so proud of it, too. If folks are interested in finding out more about what you do or who you are, just want to connect with you in a different way, do you have any ways we could do that?

    Jake Bernstein: I do. So, I'm actually a co-host of a podcast called the Cyber Risk Management Podcast. Everyone gets one guess to figure out what that's about. And I mean, honestly, we don't have a super clever domain name for it at this point, but if you Google The Cyber Risk Management Podcast, I promise you'll find us. I'm on Twitter, sort of. My screen name is @JakeBernsteinWA, no need to spell that out. If someone really wants to find me, they can. But really, I'm all over the community. And of course, I do have a profile page on my law firm, which is, If you can't remember any of the other stuff, maybe you can find that. So, there you go.

    Andrew J. Mason: Jake, that is awesome. Thank you so much for spending some time with us today. We're very honored to have you as a guest on the show.

    Jake Bernstein: No problem. Thanks for having me here.

    Andrew J. Mason: And thank all of you for listening today. Hey, we're curious, are you enjoying the shows? Are you enjoying learning how people are getting things done utilizing Omni software and products? Drop us a line at The Omni Show on Twitter. We'd love to hear from you there. You can also find out everything that's happening with the Omni Group at