51: We’re back for season 2!

What’s up, folks? We’ve been away for a while, and we’re back in full swing for season number two with even better content than season number one. 

Today we’re going to tease some of the early season two episodes and catch you up on what Jon and I have been up to since our little break. 

Catching up with JT

JT in August of last year, your world changed in two huge ways. Your wife gave birth to twin boys, Felix and Clyde. You might hear them in the background of a few episodes, as we usually coincide with feeding time. But, man, huge family of six now, two boys, two girls. Are things starting to kind of settle down a bit or kind of cross the six month mark? How are you feeling, man? How have you been? 

It’s been like being strapped into a roller coaster without any restraints. It’s quite a wild ride. We welcomed two twin boys, a two for one deal on babies. We decided we would try to go for baby number three and we had a tag along. But we’re actually seven months out of this recording into twin life, and it’s been a wild ride. 

You definitely have a lot of learning to do and feel very sleep deprived as well at times. But it’s a big happy family over here, that’s for sure. And noisy, by the way. So, folks listening, you’re going to get to hear some of the background noise of my life. But, yeah, take it in stride. 

Haha, I’m hearing it on my headphones, running through just a tiny bit and haven’t done any editing on the episode yet, but curious if that’ll slide into the mic or not. 

Mixing up twin boys

As a hopeful parent one day myself, I have some questions for you with a big family now, the first is with your twin boys. Have you ever mixed up which baby is which and we’re just kind of like fuck it went with it? 

Haha! I thought you were Clyde, but now you’re Felix. That’s who you are from now on. So the boys are not identical. They’re fraternal twins. And there’s a solid pound difference between the two boys. One boy is kind of shaped like a banana, long and lean, a little bit like me. And then the other one is just stalky. He’s like a big bear that walks around, like, crawls around her house. So at a glance, you can kind of get mixed up here and there. They’re definitely brothers. Most people can tell them apart once they get to know them a little bit. 

Sleeping habits

Do they sleep the same? Like, are they still kind of on the same sleep habit, or is one much better sleeper than the other. 

Oh, yeah, we totally hired a sleep consultant, which, by the way, if anybody is thinking of a second career, it’s a very lucrative second career. And necessary. Parents will pay anything to get their kids to sleep. The boys have totally different sleep schedules. They’re both very individual, very different Yin Yang kind of thing going on. But they’re now on the schedule, whether they like the schedule or not. So it’s essential if you’re a new parent. 

My one piece of advice is get your sleep figured out. Don’t get any advice from Mum and Dad and grandma and grandpa. Go hire a sleep consultant. And you’ll be like, that’s the best money I’ve ever paid, because you’ll start to sleep through the night and you’ll have a schedule, and that’s what twins is huge, right? 

Like, what time do you put the boys down? 

You put one down and then the other one goes down and then the other one is up and it’s just a babyville. And you do need some downtime. The boys need it. We need it. The girls definitely need it. 

Time management

So walk me through pieces of that schedule, that routine of managing a tsunami of children. Now, when does Jon go to bed? Between all the diaper changes? Do you get any time for yourself yet? Are you starting to ramp up on that? Are you still finding yourself getting up super early? I know we did some episodes where we dived into routines and you were getting up at stupid early hours to learn to code and stuff. Is that still a thing? 

LOL… So first off, I got to shout out to my wife. She’s a true hero in this story. I’m just a passenger along the ride. So she’s on maternity leave and has the care of the boys while I work. So that’s my time for myself. I go to work and it’s like, yeah, it’s perfect. I find my Zen state there, grab the noise canceling headphones and crank up some tunes and good to go. 

You know, sleep is sleep. You get a lot of interrupted sleep with babies in the house. One or two babies, it doesn’t matter. But, yeah, I still get up stupid early, usually about 05:00am for those who actually care. 

Having a 4th kid is wild

You said to me at one point that having a fourth baby is like being handed a baby while you’re already treading water. Do you still agree with that going from zero to one is still the biggest transition now? Like, going from two to four? 

Yeah, it’s an interesting question. Zero to one is a big transition for your life as an adult, especially like, my wife and I were married seven years before we started creating a tsunami of humans at our house. So we had so much time to go for dinner, late night walks and all this stuff that visiting friends. It was just so easy. Just throw your jacket on and go. Now leaving the house is like packing for a camping trip. And we’re just going down the street to the neighbor’s house for a play date. So there’s a lot that just comes with that zero to one transition. I’d say is the bigger of the two transitions. I’d say going from two to four, you strap yourself in. It’s pretty wild because you have a lot of family dynamics. Now the older two are playing together, which is like a saving Grace. So there’s no boredom in our house, that’s for sure. But yeah, two to four is a pretty steep transition as well. 

Investing in a sauna

So you mentioned you get some of your you time when you get into work mode. I know that another way that you’ve been kind of doing this has been… just tell our listeners about the freaking sauna that you bought and how that’s changed your life. And are you still making that a big part of the routine?

The infrared sauna. So, yeah, I got an infrared sauna last year. And for those who know me, I’ve talked long about buying a sauna for myself. So it’s a bit of a spoil me. Yeah. It’s just forced meditation time. I go in there with maybe light music and then just me and the sauna and some heat. 

You come out very relaxed. The sauna is, for the most part, soundproof, too. So it’s truly like a little yeah, I got like a little rug. I got some decorations around it, and it’s perfect. Ton of life. 

Almost sounds like an incubation tank where you get to hide out from the rest of the world, sweat all that power. Yes. Like the isolation tanks. I know. The Joe Rogan life. No, thanks. 

Back at Klipfolio

So after your parental leave, you kind of took back the helm of leading Klipfolio’s marketing team. Talk to me about Klipfolio, about what’s exciting. What’s the thing you’re the most excited about cooking up these days? 

Free promotion on our show. Yeah. Honestly, for me, the work at Klipfolio, I’ve been there for so long. Right. Like ten years of my career. For me, the challenge is still there. The mountain is still there to climb. 

We’ve got a good team. Like, you know, some of our team members as well. There are new team members and we execute. And that’s what I like about marketing. I don’t like theoretical marketing. I like marketing in live environments with real data to see what works and what doesn’t work and keep iterating. 

So lots of cool stuff going on on the product side, the Power Metrics products, which we launched last year, two years ago. So lots of interesting features and developments in the next couple of months coming up. So, yeah, cool stuff going on. 

Yeah. Still friends with a lot of Klipfolio and alumni Klipfolio, too. 

Yeah, there’s always the alumni Slack channel, which I actually signed out of permanently because I feel like I’m crossing Church state lines here. 

So that’s been my break. But Phil, you’ve not been quiet yourself either. You’ve got a lot going on. 

Catching up with Phil

You started at Automattic, WordPress.com in June last summer. You’re like ten months into this gig. And I know we’ve talked a lot on the show about startup life, enterprise life, consulting life. And I always felt like there was that little bit of a curiosity spark for you. Now going enterprise. So what’s it like? 

Yeah, it’s been pretty wild, honestly. Automattic is like a mini Berkshire Hathaway type of holding company of sorts. Housing many different products and brands under one roof. We have colleagues that work on WooCommerce, the open source Shopify. We have Tumblr, Taylor Swift’s favorite social media platform is still kicking around. And some coworkers work with me on WordPress.com. But we have WordPress VIP, Jetack, LongReads, SimpleNote, like a big list of companies. And even since I joined, they acquired some cool companies like PocketCasts, one of the best podcast apps that I use all the time. If you’re listening to us right now on Apple Podcast or Spotify, check out PocketCasts. It’s a much better listening experience, especially the Discovery engine, but also a big fan of Day One that we acquired. It’s kind of like a Journaling app that I’ve been using for over a decade now. 

But yeah, WordPress.com isn’t a 2,000 person company. Automattic is like 2,000 ish people, but WordPress is 400 ish people, but still like the biggest marketing team I’ve ever been part of for sure, like comparing it to some of the earliest days at Klipfolio, or even like my days that Close, talking about a much bigger team, like, much bigger pieces of the puzzle. 

Transitioning to asynchronous

But I think honestly the biggest transition period for me was less about working for a bigger team and more about trying to figure out how to work productively asynchronously across multiple different teams. We use a tool called P2, which is another product that we run. It’s like an open source collaboration tool built on top of Gutenberg, and it’s how we mainly communicate with each other. 

So we did one episode in season 1 about what is asynchronous communication. And it’s not like ditching email completely. But aside from a few HR emails for us at Automattic, I don’t think I’ve ever really had an email from a colleague. Like, we don’t do email at all. Everything is P2 or Slack, and we have these synchronous Zoom calls here and there, but any key decision and everything we kind of do project wise is P2. 

Think of all the slide decks that you do, the teams that you run through, all the synchronous meetings you have everything that’s kind of like output related or even brainstorming strategy. All of that is posted back on P2. So a lot of our time is actually spent on written asynchronous communication. So yeah, it’s like a forcing function, but there’s also a big reading piece of that too, like catching up on what other teams are kind of working on. 

I remember working at synchronous companies and if you missed a week of vacation, I was like, shit, I need to chat with X, Y and Z, get them into the room together. Like catch me up. Like, what did I miss? But that’s not a thing in an asynchronous company. All of those teams have been pumping out updates during the week that you’re off and it’s up to you to spend half a day just reading and catching up and commenting and then participating in discussions and stuff. 

But yeah, man, I want to say it feels like a different world, but I think it’s where the world is moving. Everyone is kind of remote nowadays, but everyone is struggling with 9 to 5 Zoom meetings and just like, how the fuck am I going to be productive like this? Asynchronous I think is the future. 

Joining an asynch company

And we talk offline quite a bit about this, but this is an area where I just have unending curiosity, the idea of asynchronous. I love it. First of all, you come back from vacation and you have all the updates that you need, but it’s easy to write an update sent to fire off a quick update. What is it like and how do you manage your process on staying updated across the company? And when you join the team, how the heck did you even get in and get yourself all the contacts you needed to be productive? 

Yeah, joining was really tough. It was like drinking out of a fire hose. But it’s like that for everyone, like whether it’s synchronous or not, you’re joining a new company, you’re inundated with information and you’re like, Shit, what’s important? What do I need to figure out now? But it is trickier here for sure because as the company grows, more and more individual teams create their own P2s and you’re just like, what do I need to read what’s important to me right now? 

I think that’s the skill that I’ve sharpened over the course of my first year here is figuring out based on my role, what impacts what I do day to day. What are the P2s that I need to read? So I start off my day with 15 to 20 minutes of just reading and catching up on P2 because we’re global company. There’s people posting stuff throughout the night when I’m sleeping. I usually start work at 7:30. So a lot of folks are posting from 330 to eight and then catching up on those updates. 

So on my calendar I have carved out pieces of just P2 reading. And then as part of my role at the end of the week, we ask everyone on Slack to post what they’re shipping next week or what they’re planning on shipping next week into a big doc. And then we share that and cross post it in a bunch of different other teams. Our Happiness engineers like those are the folks on customer support. They know all the time what the marketing team is shipping, what the product team has coming down the pipe. So yeah, there’s like a process to it. And honestly, you talk to different folks and it’s a bit different for everyone. 

Saving meeting time

And probably you have public access to a whole bunch of different projects across different teams. You get nosy in a hurry or down a rabbit hole. My curiosity is how much meeting time do you think you save? Like how many video calls do you think you not have to have because of async. 

I’ll show you right now, my calendar on a weekly basis: I have two or three recurring meetings, like with my direct team, a couple of one on ones with my team members and my CMO that I’m reporting to. And that’s pretty much it. Compared to previous jobs, I would say that I’m saving maybe a good 10ish hours per week of synchronous meetings, of not having to do face to face stuff and then take down notes and those notes kind of never go anywhere and you don’t share it across folks. 

The meetings that I do have synchronously that are with other teams and if we come up with a decision or there’s like a cool brainstorming topic, I take 10 minutes and I write those down in a P2 post and we share meeting minutes from that meeting itself. So we saved that time from synchronous meetings, but we spent a good chunk of it writing updates. And I’ve gotten a lot better at it now from figuring out what is important, what isn’t important, and how to just communicate faster than I did before. 

But in the early days, I don’t know if the trade off was apples to apples, because the time I was saving from synchronous meetings, I was spending all that writing and trying to focus on: Do I have any typos in there? I need to write really well. Like I’m on the marketing comms team. I need to eloquently say what I’m trying to do. But the process is a bit better now, but yeah, definitely saving a ton of time on that. 

Exciting work projects

Yeah, cool. I like that. I think a lot of listeners will think like there might be a hybrid strategy, especially if you’re going back to work in the office. I think a lot of people, their companies are either asking them to come back to the office or mandating it to some extent, but I feel like there’s a sweet spot for everybody here. Like more asynchronous communication, less meetings, but still informed on all the information. 

You’re coming up to one year at WordPress.com, what are you most excited about? 

A bunch of stuff, man. I think I’ve sharpened my growth, experimentation skills, for sure. I dive into a lot of email copywriting. I think though, that WordPress, the product itself, is fascinating. As part of a new mandate, we got to take a tiny part in rolling out FSE, which is the Big 5.9 update that came out a couple of months ago and it was a big chance of just diving really close into the product, like kind of wearing a product marketing hat for a bit and yeah, just like massive scale. 

It’s been really fun to work on small startup teams and do a bunch of shit and celebrate 1,000 visitors on the site and consider that like a big win for a little startup. But the WordPress scale is like crazy, man. Our 5.9 update is now downloaded by over 60 million people. It’s been super fun to work on stuff that has so many different eyeballs, but yeah, really fun tagging along on some of that stuff and seeing everything else coming down the pipe. But yeah, man, it’s been a fun time for sure. 

On NFT and web3 communities

I know you talk about this and this stuff goes over my head all the time, but you’ve been getting into NFTs. You said W three, is that right? Am I sounding cool enough? 

Yeah, definitely haha. I’ve been diving into web3. I think one of my goals in January was just to really figure out what the hell is going on in that space. Kind of been dabbling a little bit in crypto and Bitcoin and stuff for the last couple of years. But web3 kind of really blew up on social and online and stuff and bought my first NFT a couple of months ago, joined my first DAO community. It’s called Decentraliens, Invisible College. Super cool stuff. 

And yeah, we’ve actually got some NFT, like web3 related type content coming up on season two. One of our guests that he just confirmed last week with us. He’s one of the founders of the community I joined. So yeah, really excited to dive into that. I’m just like a huge nerd when it comes to just diving into new tech, new changes, like trying to stay on top of shit, even though I don’t really understand most of it. Like excited to learn about that new world. 

Coming up on season 2

And yes, maybe we can chat about what season two is kind of coming up here with the craziness in your life. Jon, it’s been easier for us to kind of like jump into really focusing on getting some really good quality guests on the show for season two. 

We’re going to hold out some names here. Maybe we’re going to tease it out on Twitter, but we are working on some illustrations for some of those cover arts. We’ve got a couple of episodes recorded already. Some big names, man. 

Not that we didn’t have big names in season one, but some folks are really huge on Twitter. Some folks are like C-level and big tech and some are still kind of the up and coming superstars that we’ve mostly had in kind of season one. And, you know us, we’ve got a nice mix of folks and wide ranging topics and opinions and. 

Yeah, really excited to get going again, man. Yeah, it’s been a long break, like you said. I’ll just reiterate we’ve got some killer guests and I think every guest we bring onto the show has a really solid purpose for us in terms of what we’re trying to achieve. Like the up and comers. I think of great perspectives on your own career if you’re coming up to that promotion point. But we’ve got some in particular, some subject matter experts to get me excited to get technical on the cast with. And yeah, I’m pumped. 

Alright, folks, so yes, looking forward to seeing you in the comments for season two. We’re still aiming for Tuesdays and yeah, we’ll be teasing out our launch dates, but by the time you listen to this, we’ll be launched already. So catch you guys next time.


Intro music by Wowa via Unminus
Cover art created by SLB

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