Get to know the people and stories behind Omni’s award-winning productivity apps for Mac and iOS.

Feb. 20, 2019, 6 a.m.
Brent Simmons, Marketing Human

Brent hosts The Omni Show and writes blog posts, articles, App Store descriptions, newsletters, and other things for The Omni Group. That is, he normally hosts The Omni Show, but this week we have a guest host, Rose Orchard, who graciously agreed to interview Brent.

Show Notes:

It’s tempting to say that if words and sentences are involved, then Brent probably works on it. But that seriously underestimates the sheer amount of writing that a software company produces.

Brent doesn’t write the manuals: Dave Lonning does. He doesn’t answer all the support email or write support articles: people on Brian Covey’s support team write those. He doesn’t write all the blog posts: Ken Case and others write blog posts too. He doesn’t write all of Inside OmniFocus either: a whole bunch of different authors write for that site. He doesn’t write release notes: the various Prime Ministers write release notes for their respective apps.

Even though he doesn’t do all these things, he does, somehow, manage to look busy. Well, somewhat busy. Busy-ish. :)

You can find Brent on the web at his long-time blog at And you can find him on the Omni Blog and the Omni Microblog.

Some other people, places, and things mentioned:


Rose Orchard: 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. Music.


Rose: I'm your guest host, Rose Orchard, filling in for Brent Simmons who is the guest for today's interview. Say hello, Brent.

Brent Simmons: Hello Brent.

Rose: Okay so, welcome to the show, Brent. I'm guessing this probably not your first time on a podcast?

Brent: No, but it's my first time as a guest on The Omni Show, so I'm pretty excited.

Rose: I'm very excited to be today's guest host.

Brent: Yeah, thank you for doing it.

Rose: So what do you actually do at The Omni Group? I mean, we know there's an Omni Show, and there are cat pictures.

Brent: Yes.

Rose: And there's a lunch menu every day, but what do you do at The Omni Group?

Brent: Well, I also really enjoy eating the lunches.

Rose: Oh, that's very important.

Brent: That's critical. I tend to write a post about what's coming up for lunch as soon as I start thinking about lunch, which is around 10, 10:15 AM every weekday. I realized that I'm the Garfield here. I would have several lunches a day if I could.

Rose: Okay, and how many of those would be lasagna?

Brent: None, unfortunately, due to my unfortunate lactose intolerance.

Rose: Oh, that's a shame.

Brent: It's sad, I love lasagna. I'm a handicapped Garfield, it's terrible.

Rose: Having just met lunch staff, I'm sure they would be willing to try a lactose free lasagna.

Brent: Yeah, they probably would or make me something equally yummy.

Rose: Yes, of course. So you work in the marketing department, you haven't always worked in marketing at Omni have you?

Brent: That's true. I was hired here as an engineer, because I do have some, well decades of experience doing engineering, so it seemed like a reasonable thing to do. I did that for, about three and half years, and last March I switched over to marketing. And it was strange going from opening Xcode every day and looking at the bug tracker and filing through stuff in that way, to opening up BBEdit every day but still looking at the bug tracker.

Rose: Of course. Old habits are hard to break.

Brent: Right, and there's a bug for this show, right?

Rose: Right, exactly.

Brent: The bug tracker runs everything.

Rose: Okay, yeah. So it's kind of like the backbone, in some ways, of what people are doing here?

Brent: Yeah, sure.

Rose: Help people keep track?

Brent: Mm-hmm (affirmative), yep.

Rose: What prompted you to switch to marketing?

Brent: I was asked by Grayson and Ken if I would like to make that switch. I had started The Omni Show before that and had started attending marketing meetings. Derek Reiff was the marketing guy at the time and Grayson was the boss, so I was attending with the two of them, so I was kind of in it a little bit.

Rose: Sneakily pushing your way into the marketing department.

Brent: Right, because for years as an indie developer working for a small company, I had to do a lot of the promotion myself, so I have many years experience with that, and been blogging for 20 years, done podcasts before, and I know my way around social media, so I was actually qualified for the job. Nevertheless, people were surprised, you're doing what‽

Rose: I'm sure people now wonder what you even do all day.

Brent: Yes, yes they do.

Rose: And then Friday comes and there are either cat pictures or dog pictures so far.

Brent: Uh-huh (affirmative), yeah.

Rose: So then people go, "Oh, so he was doing this all week."

Brent: I have a set of recurring tasks that I do each morning, and the first thing I do, and I actually have a task in OmniFocus for this, is to check Ken's tweets, because sometimes I learn things that way, but often there are good things to retweet or whatever, right? Step one, check Ken's tweets. I run the @OmniGroup account and we have a number of searches for different apps and there are mentions, go through that, do Mastodon, do Facebook, do and look at our emails sent to marketing. Really the first half of my day is just the same stuff that I do every day. Second half is mainly writing, so that's blog posts, that's things for Inside OmniFocus, or it might be coming up with a new tag line for a product, or it could be any number of different things, or writing the text for the app store. All that has to be written by humans and reviewed by humans, so it's just all kinds of stuff. Mostly writing. One part of my job that I really need to get better at is the screenshot taking. That's a tough one.

Rose: With shadow or without shadow?

Brent: Right. Well, getting the mouse pointer in there has been the real difficulty lately.

Rose: Doesn't macOS automatically remove the mouse pointer from screenshots?

Brent: Yeah, it does.

Rose: Okay, so if you want the mouse pointer in there ...

Brent: And if I want it then like how do I do that? Well there's an option, so I turn on the option, and it still doesn't appear. But the harder part is how do I make a screenshot that looks really really great? And that's actually a skill that takes a lot of practice and a lot of thinking.

Rose: And with something like OmniFocus you can't just take a screenshot of OmniFocus, you need to have good tasks in there that actually make sense or maybe they're a little bit funny, tell a story or something. It's probably a couple hours prep time just to get a test database, right?

Brent: Sure, yeah. We do have some test databases that we can reuse. But it's a matter of getting that on the right kind of device, and then setting up QuickTime Player, and all kinds of crazy stuff.

Rose: So you mentioned BBEdit for writing, have you always prefer BBEdit for writing?

Brent: I've been a BBEdit user since 2.5, or something like that, a long, long time ago. And it's a real Mac app. For instance, if I hit undo, it undoes the right amount instead of just character by character. Preferences is an actual window with check boxes instead of like, typing in Ruby or JavaScript configuration. It scrolls fast, handles really, really big files really well. Multi-file searching is great.

Rose: No, I love the multi-file search and replace in BBEdit. My blog is based of text posts, so if I make a mistake or I decide I'm changing a header or something then I can just do a multi-file search and replace and save, and its just done. It's like "whoa, did I really just do that?"

Brent: Yeah, BBEdit's amazing.

Rose: So, another big question for the writing, do you write in Markdown, or do you write in HTML, or plain text, entirely?

Brent: Markdown, everything's Markdown. Even notes to myself, even emails that don't get rendered as HTML, they just—

Rose: Like the email that you sent me yesterday, which is a plain text email.

Brent: Yeah, and said we have press releases and things. I have to write emails to special friends. It's all in Markdown. And it looks fine in email.

Rose: Exactly. Like I even use Markdown in [Messages] myself cause it doesn't render, but everybody knows what it means.

Brent: And that's part of the genius of it, I think, is that that works.

Rose: Do you use the original Markdown or are you using MultiMarkdown, one of the extended versions?

Brent: Really a subset of the original Markdown. So what do you call those marks, octothorpes? ...for heading level, and then any number of asterisks for bold or italic. And then there's that weird link syntax. I think that's about all of my Markdown vocabulary. You can write almost anything that way.

Rose: Yeah, exactly. And for people not so familiar, octothorpes are also called hashtags. Alright.

Brent: Pound sign, that's what we used to call them.

Rose: Yeah, it used to be called the pound sign on the phone. Which is weird because the British pound sign is completely different.

Brent: You know, I never made the connection between pound and pound, in those different contexts.

Rose: And there's also pounds, the weight, which is lbs.. Confusing. Okay so aside from BBEdit, what do you use to do your job?

Brent: Let's see, it will make a sound but I'll open my—

Rose: I mean we've heard OmniOutliner.

Brent: Right sure, yes.

Rose: you mentioned that on a couple of the Omni Shows that you do you outlines in OmniOutliner.

Brent: So, I keep Outliner open all day, and I have a file called "Log," and every day I record things like blogs or something, that might mention OmniFocus or OmniGraffle or something. So I record URLs, when I post the "What's coming for lunch today," I record that URL. I work on a given bug. I record what I did, write a draft, that kinda stuff. For each day and all that lives in OmniOutliner, which is nice. Also I have another one for meeting notes.

Rose: Of course, yeah.

Brent: And those are my two main uses for OmniOutliner. Of course, I mainly live in OmniFocus and mainly live in the Today, the Forecast view. Because, I'm at work today, and I need to know what I need to do today. And so that's essentially how I live.

Rose: Yeah, and with the new event view, you don't have to switch to the calendar to see if you have meeting now, for example.

Brent: Right, Right. I have my computer open, it says "The Omni Show, Rose Orchard, recording two shows."

Rose: Ooh, two shows. Letting the cat out of the bag.

Brent: Yeah, I know. Well, this will be published second.

Rose: Yeah, of course.

Brent: Then of course, there's mail, NetNewsWire, Calendar, MarsEdit, Slack, boy...

Rose: So you use MarsEdit for posting to the Omni blogs, then?

Brent: Yeah, yeah. Not always, I also use the Mac app.

Rose: Mm-hmm (affirmative) Yeah.

Brent: I really like, Slack is an awful app, but it's a great app for what it does.

Rose: Oh it is, yeah.

Brent: I mean, I just wish it was a real Mac app. But I have Slack open constantly, and I really enjoy The Omni Group slack.

Rose: Yes, it is a very fun place to hang out that's just full of friendly nerds.

Brent: And so I have a group for like, family, groups for some side projects, local people, stuff like that. What else do I use? Mattermost is our internal chat application. And I think we probably picked it because we can self-host, and we like that kind of privacy and security and everything. OmniBugZapper, listeners can't see but, I'm turning around to show Rose. This is our bug thing.

Rose: Okay.

Brent: Rose is know looking at all the tasks in red, which are mine, which are overdue. But yeah, its just basically a Mac app with the ability to do searches and assign bugs to people, add notes to bugs, all kinds of things. And it's in some ways the heartbeat of the company.

Rose: So you said, for example, this podcast episode is a bug, so everything here is a bug, right? Not just bugs.

Brent: Right. Pretty much everything goes through this. Except I don't have a bug for "Check Twitter every day." I mean, that would be silly. Let's see, I used to use Versions, because we're on Subversion here. And Versions is a desktop SVN client. I've moved my marketing stuff into Git lately, which I much prefer, and use the command line for that.

Rose: So you're not using a Git application like Sourcetree or anything?

Brent: I haven't been. So, my marketing repository is just me. And I'm a pretty simple Git user, but that's all I need. I just need to commit stuff and push it and whatever. That works out. I use Google Chrome entirely for the purpose of Facebook, when I have to do Facebook stuff. Because I wanna segregate that from—

Rose: Okay, so they can't track you everywhere else?

Brent: Yes, exactly.

Rose: That makes sense.

Brent: Mm-hmm (affirmative). Yeah, its a row of bookmarks, it literally has one bookmark which is to our Facebook page.

Rose: I think we can allow that. So you're not personally a Facebook fan, then?

Brent: ... No.

Rose: Despite working next door to them?

Brent: Yeah. I know, I know. In order to do my job, I had to actually create a Facebook account, so that I could update our Facebook page.

Rose: The trials and tribulations of being in marketing at Omni.

Brent: Yeah, right. It sounds like such an elitist position. Like "oh my god, for my job, which is nice and cushy, I had to make a Facebook account, oh no!"

Rose: Well, I will tell you listeners, I have seen Brent's office, and there is a very nice cushy bean bag in there, so he's not joking about the nice and cushy job here.

Brent: Yeah, it really is. The bean bag is huge, and it's the smallest one.

Rose: Yeah, bean bags can be. There's like, children's bean bags, which if you try and sit on them as an adult, looks ridiculous and is very uncomfortable. And then there's adult bean bags, which take up basically the whole room.

Brent: Yeah. And this is a small adult, but it's enormous.

Rose: But it looks very comfy.

Brent: It is, yeah. I do most of my best writing on the bean bag. So I get on the bean bag, move my office chair close enough to put my feet up on the chair, and relax on the bean bag with my laptop, in that Tyrannosaurus Rex position with the small hands on the laptop.

Rose: Does the chair not roll away when you do this?

Brent: No, no it doesn't. Yeah, it works out somehow.

Rose: Impressive. So you mentioned that you have NetNewsWire on your Mac, and that you have side projects. NetNewsWire is one of your side projects that recently came back to you, isn't it?

Brent: Yeah, it is. NetNewsWire, I started it in 2002, seems like quite a while ago now. And worked on it up through 2011 or so, when we sold it to Black Pixel. It kept it going and everything, but then, yeah, last year, I talked to them and got it back. It's like one of the greatest days of my career. It's the app I'm certainly best known for. I've put more of my own hard work, and self, and love into that app than into really anything I've ever done. It's wonderful to have it back, and now I'm working on version five. I never thought I'd be the NetNewsWire guy again, but I am, and I'm so glad.

Rose: I'm on the beta, and I'm in the Slack chat channel for that, and it looks like it's going really well.

Brent: Yeah, it's getting there.

Rose: Yeah, it's a very fun application to use, just for reading news, which ... yeah, reading news doesn't sound like fun, but when you can put anything into there, pretty much.

Brent: Yeah, right. When I started it, there was no Twitter or Facebook, or anything like that. And RSS was how you got news. Now people have a lot of alternatives. Which means a number of different things. One is, I don't have to write the great app that every human in the world is gonna want. I can write knowing that it's a niche audience, I can do the thing for that audience, and that's a lot of fun.

Rose: But you seem to have a lot of users that really care about the app, at least judging by the Slack channel, everybody's excited and willing to talk to you about stuff.

Brent: Yeah, and that's a lot of fun. When working on my own apps, I've never been the kind who just goes away in his office and is totally quiet. Back in the old days, 90s, when I had a mailing list, which was super active. Must've been, I don't know, a hundred people or something on it, and just constant talk. Because I'd say "You know, I'm thinking about this." And then I'd get a whole bunch of feedback and that was great, it was a very social way to develop. So I like doing that, only now with Slack these days.

Rose: Yeah, and I mean, I can imagine in some ways that must be quite hard, doing a side project officially by yourself, because NetNewsWire is yours. But because of the internet, it's not by yourself, is it? And other people, of course — because NetNewsWire is open-sourced, right? — So other people can make pull requests and so they did, which is nice.

Brent: Yeah, that's a brand new thing for me, but I've enjoyed it. For instance, Olof Hellman did all the AppleScript support, because he knows AppleScript. Daniel Jalkut added, I don't know what it's called... Safari Extension, for subscribing to a feed, so I didn't have to do that. A guy who I didn't know before, Maurice Parker, just went through and fixed a whole ton of bugs. So great.

Rose: The internet is awesome.

Brent: Truly is.

Rose: So NetNewsWire is not your only side project, is it? You've got a few other little things going.

Brent: So the other one is called "Rainier," and it's an app that's inspired by UserLand Frontier. Which never had a giant audience, but was a scripting application for Mac, back in the 90s. And still exists, I think, and could maybe run on a Mac today, but is not a modern Mac app. It may not have more than a couple active users, the main one being Dave Winer, whose company invented the app in the first place. So it's inspired by that, it's not compatible with it, and it's not gonna be the same, but it's gonna be very similar. Because I found the ideas in that app to be interesting and, at least back in the day, super powerful.

Brent: And so my theory is, if we bring back those same ideas, we might get some of that same invention and innovation that we had back then. Because it was in Frontier, for instance, that the early blogs were written. RSS was invented, podcasting was software running in UserLand Frontier, both reading and writing, before it was anything else. And so if we have something like that, what else can we create? I think we have a real need to get back to the open web, and the web of tinkering, and the web of where an individual can make a thing. So I really wanna bring that back. And it's gonna take me a while, because... nights and weekends, and I also have NetNewsWire to work on. It's also open-source and hopefully it will get some help, and that will be cool.

Rose: I'll cross my fingers because it really does look promising, and that's why I'm excited about it, because you're not making a thing, you're making a tool which makes things.

Brent: Yeah, right. Exactly.

Rose: I mean, it technically is a thing.

Brent: Yeah, right. But it's a development tool—

Rose: It's very free form.

Brent: Yeah. It's not Xcode, it would be meant for people who've never even programmed before, or should be able to pick it up. And people who have programmed before should hopefully find it powerful and fun and everything too. Super excited about it. I just wish I had two of me, so I could come to work and also stay at home, work on it all day.

Rose: Now, I remember, what was it? I think it was Bernard's Watch. It was a book years ago, where a boy had a pocket watch, where he could literally stop time, and run around and do stuff. And I so often wish that I had something like that, and it would be really useful for you too.

Brent: Yeah, yeah, For sure.

Rose: Come home, you could take a nap whilst also working at the same time, which, that would be amazing. So, what else do you do in your spare time? I've heard there's something about you being a musician?

Brent: Yeah, I play a lot of music, and I always told myself that, toward the end of my career, I'd allow myself to do that more and more. So I am. I'm actually working harder to get good at playing music. I've always been good enough to play songs around the campfire and people will sing and they'll be like, "Oh Brent, that was great thanks." But I wanna be actually really, if you heard me play, you'd be like, "Wow, that's actually quite good, thank you." So, I'm learning that.

Rose: What instruments do you play, then?

Brent: Guitar is my main one, but also piano. I just got a banjo. It's really cool, it's an antique, it's about 80 years old, and it's older than the style of bluegrass picking you're used to hearing. So it's actually called a Plectrum banjo. Four strings instead of five, super long neck, and it was meant to be played in jazz bands of the era, or big bands. Has a resonator, so it's super loud. You play with a pick, but the idea is it could be heard over the saxophone to your left, and the trumpet players to your right. And it's gorgeous, has all this ornate woodwork and everything. It's a marvelous, marvelous instrument.

Rose: Nice.

Brent: And I have a whole lotta fun playing that thing. Mainly I think because it's super loud.

Rose: Yeah, and loud is always part of the appeal with music, right?

Brent: Yes right. But when it's loud and it's a banjo, people these days aren't expecting to hear that, that much.

Rose: Yeah, I mean I can imagine that being a very pleasant surprise. I hope your neighbors agree with me that it's a pleasant surprise.

Brent: So far, I've kept the windows closed.

Rose: Oh okay. Well, summer will come.

Brent: Yeah that's right. I will fill the neighborhood with really loud banjo music.

Rose: Excellent. And before summer you have time to practice as well, so you can be even better and stun them.

Brent: Mm-hmm (affirmative).

Rose: Should be good. Didn't you play with James Dempsey and the Breakpoints at WWDC last year?

Brent: Yeah, and at some of the Swift by Northwest conferences, yeah. A few times. Played piano at the Breakpoints show at WWDC, but normally I play guitar with James, and that's a ton of fun. I don't play in front of people all that often, but when I get to, yeah, I love doing it. And I realized at one point, that doing a prepared talk, I'm nervous. I mean, I hope it doesn't show terribly, but I am. But playing music in front of people, there's no nervousness whatsoever. I love doing it so much.

Rose: I'm the exact opposite. Like, a prepared talk, I can just go out there and do it, it's fine. I used to be a professional presenter, but going out and performing music, it's like, "What if I make a mistake? Its really hard to cover it up." The reality is, apart from professional musicians, most people aren't gonna notice a mistake, and even if they do you can be like, "It was intentional," and just pretend it was all fine. How long have you been playing music?

Brent: It started with guitar when I was 12, which, if I could do the math, was 38 years of guitar playing. But I've only recently started to get good at it. My obsession has been country blues. Very, very old school like, guy playing a guitar, could be on his porch or something, that kinda sound. And I had never thought about that, until I started to learn how technically difficult it actually is. I thought, "It can't be that hard." And then I learned, if you're playing fingerstyle, your thumb has to be completely independent of your fingers. Because your thumb is keeping a steady "thun thun," and then your fingers are doing all kinds of other crazy things.

Rose: Which is kinda like the piano, your left hand having to be completely independent of your right hand, but two levels up, because it's on the same hand.

Brent: Because it's on the same hand, yeah. That's super tricky. And lately I've been getting into, more and more, playing with the slide. I just adore the sound of a blues Bottleneck guitar, it's such a very vocal sound. It almost sounds like a human, and there's a kind of a crying element, a little bit, it's the blues, right? It's a very emotional kind of music. But I play the blues because it makes me happy.

Rose: Well, there you go. As long as it doesn't make you cry.

Brent: Right, exactly. The blues is an antidote to the blues.

Rose: Yeah.

Brent: That's the way I look at it.

Rose: I can see that working.

Brent: It does for me. People listening to it, maybe not. But it works for me.

Rose: Personally, I think if the musician is happy when they're doing it, when they're performing, then it's enjoyable to listen to.

Brent: Yeah.

Rose: Of course some music does make you cry.

Brent: Yeah, true.

Rose: Though, sometimes it's just because the playing is so terrible. Which I very much doubt yours is.

Brent: Well, who knows. I was thinking I was gonna demonstrate, but I went to change the strings on my guitar — I have a guitar here in the office — and because I had broken a string, so I'm just gonna change them all. And as I'm changing, restringing, I break the first.

Rose: Oh, of course.

Brent: So, I got nothing.

Rose: Aw that's a shame. Maybe you can slot it in afterward. I mean, Mark is a editor with the wiz —

Brent: That's true.

Rose: I mean, a wiz with the editing! [laughter]

Rose: So thanks Brent, how can people find you on the web then?

Brent: You can go to, right? And go to our Or Twitter, @OmniGroup there. And you can find my personal blog at

Rose: Excellent domain name. I'd also like to thank our intrepid producer, Mark Boszko. Say hello, Mark.

Mark Boszko: Hello Mark.

Rose: And I especially want to thank you for listening. Thank you. Music.