Mailbag for September 26, 2025

Public figure pressures, posts that make you click, adjusting to Search Engine Optimization in the age of AI, sports we play(ed), loving Japan, and future plans

Dear Squawkers,

Lainey and Sarah are coming off one of the busiest periods of the year and are running on fumes, so Emily and I are here to answer questions that relate to our side of the team. (It’s also someone’s birthday today, so there’s that.)

It’s been about a year since our last dedicated mailbag (aside from my answering relevant questions in the last year when Lainey or Sarah do lead these features) and a couple of you asked things that we’ve covered before regarding the day to day running of the website. Please click here for a fresher on Emily’s day-to-day, my feelings on how this turned into a business in the early days, website stats and most read content, and other things that might overlap since our focus is more on the business of running the sites and less the gossip itself. And for those of you who had questions about gossip, please either re-post them when we do our next mailbag, or I’m sure Lainey and Sarah will dive back into to this week’s gossip related questions to respond.

Before we get to the mailbag though, let me touch on something that really hit me from last week’s mailbag. Obviously, Kimmel has been the main story this week and last week Squawker Betts asked about fear and truth and speaking up, given all the targeting of media by governments and lobbyists, and the conflicts in the world garnering very passionate reactions from everyone with a social media account. Lainey’s answer, if you haven’t read it is here (last item).

As you all know, we’re married and we’re also business partners, so that in itself is a juggling act at times because not only do we often not agree about elements of running the site and need to find compromises - the other day we had an argument over text about what pieces we would be preparing for The Squawk which resulted in several circled screen caps by Lainey to which I replied with a less than productive circled screen cap of my own – but we also seek balance between TALKING about the business, period, and knowing when to shut it down and just be us. That part is difficult sometimes because we often don’t get much of a chance to chat or text during the day with her insane schedule, and when she gets home, I need to dump stuff that’s been on my mind all day when she’s mostly wanting to just check out. Those are some of the challenges of running a business with your spouse.

There are others. I cannot relate to some of her day-to-day experiences, of course, with her being a somewhat public figure. And there are also things of mine that she cannot relate to, like being the ‘silent’ partner behind the banner and the name who has to watch all the things that she goes through publicly and the scrutiny that goes with the job. The business partner in me accepts those parts and helps from behind the screen, so to speak, as much as I can. The husband in this partnership struggles with some of those things. For instance, our “old content-gate” from a few years ago was extremely challenging to observe from this vantage point because of how much of the blowback she faced head-on. And more recently, all of the emails for us to say this or that about what is happening in other parts of the world, or how disappointed some people were that we were so ‘silent’.

When I read her talk about broken dreams and fear, it kind of struck me how rare it is for her to acknowledge that these things do weigh on her. She has been so rock steady for so long, seemingly letting all the Twitter trolling, visceral emails, and hateful social media comments, whether it was for stuff she wrote or what she and the women of The Social said on air, seemingly roll off her back. Her reply reminded me that even this seasoned, thick-skinned pro can be vulnerable at times, and what pressures exist to not let that show. Most of the time.

JenAr had this to say in the comments below that post in response to Lainey’s answer:

“Thank you so much for articulating your thoughts around fear like this. As someone who lives with chronic, daily anxiety (I’ve heard it hilariously described as “fear of everything and nothing”), I am so tired of the toxic positivity/wellness/optimization bullshit that makes us feel like we’re only worthy if we stand up to, face, and defeat our fears. Being too afraid to try stuff is sometimes just a reality and it can be so exhausting to feel like you’re constantly fighting through those emotions. Sometimes acceptance and being kind to yourself despite fear is the bravest thing you can manage. And that’s ok.”

That part is the hardest. The husband part of the business partner who watches someone who most of the time compartmentalizes like no one else and just does the work. The part that wants to join Twitter or reply to that email and go tell some of these fine folks to go fuck themselves.

All that said, this isn’t meant to be some kind of rant about how she doesn’t deserve the heat. We are, after all, VERY privileged to be in a position where thousands of people come to our sites to read what we have to say. And as I write this I wonder if she’ll even let us post this because she has been SO allergic to sounding resentful about the valid criticism she has received, or making people feel like she should determine when enough has been said about the past.

However, the fear is always there. And over the years one of the things that I’ve tried to counsel her on while she privately dealt with some of these slings and arrows is that we cannot please everyone, but also that we cannot disavow what got us here in the first place. We would not be here today if we first weren’t that. We can only try to be a bit better and not feel like the past is a disqualifier of the moral authority to criticize the people and organizations that deserve it. And this week’s Kimmel saga was a reminder to us all of how important that is.

On to the mailbag!

Question from Hannah M.:

Forgive me if either of you have answered this before, but how do you know that a particular article on the site has made an especially loud splash? Is it just traffic to the site, or do you see more factors (like people signing up for the Substack)? I know posts about the British royals always get traction, and I assume anything re: Taylor and Travis does the same, but are there other subjects recently that are making noise?

Jacek’s Answer:

We had a similar question in last year’s mailbag about what has historically driven traffic to the main site and you can see those answers there. For the most part, those people have stayed consistent. Bennifer (then). The Royals. Taylor Swift. Blake Lively. Those articles always get the most reads. What we have tried not to do, however, is to chase those articles and force them knowing we get more clicks that way. Emily and I joke sometimes about how eager Lainey was to talk about K-pop on the site even though North America was slow to recognize what a huge cultural impact East Asian artists were having on pop culture. Not quite as sexy even to our more well-read demo than a good old Jennifer Aniston throwback.

What’s been harder to ignore since we launched The Squawk is how immediate the impact can be when we post something that is locked down behind a paywall and deemed to be juicy enough to pull out the wallet. Retro posts, especially like this one about Jennifer Aniston’s Vanity Fair interview do very well and generate immediate paid conversions. Or, again, anything about the Royals. This post about Kate’s hair a couple of weeks ago converted a bunch of free subscribers as well into paid ones.

We’re trying not to be driven by these as we go along but sometimes it’s hard to ignore the fact that the big stars generate the bigger paid conversions. That’s the way the world works, isn’t it?

Question from Monika T:

I have another question (sorry) Jacek, how are you incorporating “Search Everything Optimization” specifically how are you making sure LG site easily appears on ai apps like Grok, Perplexity, and ChatGPT?

Jacek’s Answer:

In the same way that we’ve tried not to chase clicks with our content selection over the years and write mostly what we felt people needed, my approach to SEO has been similar. For years there were all kinds of tricks to get more search visibility, like keyword stuffing, spamming other sites with links to your site to gain “link juice”, and other shady techniques that used to get results before algorithms became more sophisticated and started ignoring those ranking signals. We always focused on quality writing, trying to write informative metadata titles and descriptions, making sure the site was user friendly and quick to load, etc.

These days, as you’ve definitely heard, it’s all about AI and its impact on Search and the web traffic it drives. And there’s a shift that’s happening in the SEO (Search Engine Optimization) towards visibility to AI engines. Except there’s one big problem with this, and that is that those AI engines don’t actually move people to the source material. So there’s that.

Truthfully, I’m a bit exhausted with the degree to which this under-researched rush into AI is affecting the web and I haven’t yet tried to get my head deeply around how to adapt our site to the new era of AI driven traffic, if such a thing will even exist. What I do hope will save us and sites like ours is that with the exponential explosion of AI generated garbage on the internet, trusted voices with established followings will gain enough traction with readers who are willing to come directly to their sites because they trust what is there hasn’t been puked out by AI, or some AI “persona” who thinks it’s a human and has feelings.

Question from Charlotte:

Jacek/Emily - do either of you do a sport? Or did do a sport regularly sometime in your life? Do Lainey or Sarah? (I think carrying an Olympic torch must imbue one with sportiness even if you weren’t so blessed before.)

Emily’s Answer:

Swimming was my sport growing up as I’ve never been a team sport/competitive person. I’ve always loved being in the water but stopped swimming seriously in my early teen years because I made the mistake of going into synchronized swimming which totally killed my buzz for the sport. I lost all interest and wish I’d instead taken up racing or something more my….speed. I was very good and very fast and I wonder if I would still be swimming regularly if I’d gone with my gut on the synchro thing. It wasn’t cool OR fun!

The second reason I stopped swimming, and it hurts me to say this, is because I started to feel self conscious about being in a bathing suit once I hit puberty. My boobs were too small to fill out a suit. My ass was (is) crooked from being kicked by a horse when I was a kid (yes, I have been permanently deformed by a horse) so I wanted to wear shorts in the pool and not a proper bathing suit, which would have been required.

How many of us have stopped ourselves from pursuing something we love because of self consciousness? Especially in adolescence. Devastating.

While I don’t currently do a sport, I am pretty active. I walk daily and try to meet a goal of at least 10,000 steps a day.

I have a mostly at home yoga practice, I lift weights, and I go to clinical Pilates a couple times a month which I carry through to an at home mat practice. Pilates has been transformative for my lopsided body and I can’t recommend it enough.

Jacek’s Answer:

I never played anything at a high level. I played hockey growing up and would alternate between my organization’s A and House teams with each year, only because the group of guys one year older and one year younger than me were better and worse respectively, so it came down to whether as a group we were good enough to make it into A or double A. I wasn’t good enough to do anything with it. The “peak” of my hockey career was qualifying for an All-Star tournament of players in the Greater Vancouver area where we were pooled into groups of teams and played a round robin. And that week I got mono, so that was the end of my NHL dream 😊.

Not sure how old I was here. 15?

Otherwise, as you might have seen on Instagram, Lainey and I play golf once a week in the summer and on vacation, and I can be heard slamming balls into my simulator in the back yard on weeknights. I’m a golf freak. I have an old Scotty Cameron putter collection about 14 putters deep, I tweak my swing weight on my clubs CONSTANTLY thinking it’s the one thing holding me back from finally shooting my potential, and I also change clubs way more than a normal person for the same reason. But I love it, and have fully accepted, as has Lainey, that we play a pretty douchey, elitist sport.

Question from Cassandra:

Emily! We only got bits and pieces of your Japan trip in the chat. We demand long form thoughts and impressions! (Well, not demand... but would appreciate and enjoy😁)

Emily’s Answer:

The pressure!

My first impression of Japan once we were off the plane and on the train was how lush and green it is. Bamboo forests everywhere. Regular forests everywhere.

The second thing that stands out is how respectful people are, how polite the culture is in general. No one is walking around the streets of Japan having conversations on their phones, and they are certainly not having conversations on speaker phone for everyone else to hear. Everyone is quiet on the trains. There is no eating or drinking on the trains. It’s basically frowned upon to eat and drink outside in public no matter where you are. Smokers are sequestered into smoking rooms behind double doors, or on tiny sections of the sidewalk behind glass walls where they belong. (Cigarette smoke is a major migraine trigger for me and I think smoking in public is the rudest fucking thing, can you tell?) People don’t leave their garbage everywhere like they do here in the west, though garbage bins are hard to find, so you have to be prepared to carry your trash with you. Everyone is mindful of the people around them, of the space they take up, of not allowing their energy to leach into anyone else’s bubble. It was jarring to come home and realize just how self-centred we are in North American culture. We don’t give a fuck about disturbing our neighbours and frankly, it sucks! We’d be happier if we took a few notes from the people of Japan.

It would be almost impossible to be vegan or even vegetarian in Japan, especially Tokyo, without a plan for where you’re going to eat. Our goal was obviously to eat as much food as possible, it’s one of the main reasons we went, but I was surprised by how difficult it was to find veggies. Fresh fruit and vegetables are rare commodities. There were several times we went into ramen places and there wasn’t a single option without pork. I’m not vegetarian but am also not a huge fan of pork. I wish we had planned the food part a little better because I wasn’t totally blown away by every single meal, and I was expecting to be based on what I’d heard about Japan. That said, we did have some killer ramen, great sushi, amaaaazing okonomiyaki in Kyoto, and all the onigiri we could shove into our faces from every 7Eleven we walked by. I should note that in Vancouver we have some of the best sushi and ramen in the world, so I have high/spoiled standards.

We went to a sumo match in Osaka, which felt essential and was simultaneously impressive and hilarious. They put on a great show for us.

We went to a baseball game in Tokyo, which I never would have signed up for (not a huge sports fan, but my partner is) but I would recommend to anyone who is visiting. It was the most fun. Japanese baseball fans are more dedicated to their teams than I have ever been to anything in my life. There was a lot of intense singing/chanting and it was glorious. The beer girls have kegs strapped to their backs and hustle the fuck up and down the stands, I swear they worked harder than the players.

I preferred Kyoto and Hakone to Tokyo and Osaka. The vibe was less hectic. The temples and nature were sacred and beautiful and if I were to go back, I would do less city life and spend more time in nature. In Hakone, we stayed at two different places with private onsen since we both have tattoos. Most public onsen don’t allow tattoos. Private onsen is where it’s at… 10/10 would recommend.

From Kyoto, we took a day trip to Nara and this is also a must just to experience being with the deer. You happen upon them almost as soon as you step off the train and they’re fucking everywhere begging for their deer crackers (which you can buy from vendors in the park). We were lucky enough to be there just after some of the babies were born.

Us in Nara

My partner is also a huge Disney fan, so I sucked it up and we did half a day at regular Disney and a full day at Disney Sea (basically a more grown-up Disney with better rides, like California Adventure), and this was one of the many things that I was pleasantly surprised by in Japan. Inexpensive! Churros for $5! Clean! Organized! Friendly! Even the children are better behaved in Japan… we spent a day and a half at Disneyland and I didn’t witness a single temper tantrum.

Us at Disney

Okay, I’m ready to go back now. Lainey? Jacek? Family trip?

Question from Cassandra:

There was a poll question a few weeks ago about paying for an ad free version LG - I would pay for access to a paywalled LG, but ads are not the make or break for me. Not knowing much about how all that works, would there be reason to not do paywall + ads?

Jacek’s Answer:

This is an excellent question and also one that is very relevant to some of my answers about Search Engines and traffic declines and the death of the open web.

We are currently in the process of scoping out a big move for LaineyGossip onto a new platform. It will give us the flexibility to roll out things like gated content (if needed), ad free experiences (for those who want them), newsletters or alerts, and other things that our present-day custom-built site cannot do without extensive upgrades. Not to mention at a fraction of the cost of the hosting fees that we pay today.

I hesitate to write too much about it as we’re still early in the process, but if it goes ahead, the idea is to make the transition as seamless as possible and offer free access to similar to what we do on LaineyGossip today, with the option of adding gated or exclusive stuff later on.

There are no plans of changing anything regarding this space (The Squawk) at the start, but this new platform will put us in a better place to pivot if we need to adjust to what’s happening on the ad-driven web in the months and years to come. Stay tuned!

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That’s it for this week’s mailbag. Next week we have something a little different planned for Friday that we’ll share with you later next week. Thank you for all your questions and for reading us!

Squawk often,

Jacek and Emily