Mailbag for September 6, 2024

Gossip turned career, who reads all those emails, most read stories, why fawn over Gwyneth, behind the scenes of LG, and what to do with a magic wand...

(Image Press Agency/NurPhoto/ Keystone/Zuma/ Gregory Pace/Shutterstock)

Dear Squawkers,

Typically, you’d hear from either Lainey or Sarah in this space on Fridays. They shared their TIFF schedules with our paid subscribers earlier this week on The Squawk and because it’s such a madhouse for them and they don’t have time to do a regular mailbag this week, Emily and I are taking over and answering your questions about the behind-the-scenes stuff we do at LaineyGossip that we don’t often talk about. 

Personally, I’m excited to be able to lift some of the editorial load off the two of them and I’m sure Emily will echo that sentiment. There are times during the year, like TIFF, when the busiest periods for Lainey are business as usual or even slow for me and Emily, and we wish we could step in and help out in some meaningful way without stepping too far out of our lanes. After all, no one wants to hear my thoughts on the Bennifer situation or whether or not Travis and Taylor will make it past Week 11 of this season on a regular basis. I can talk your ear off about politics, sports, and dog behaviour, but celebrity is not my expertise so most of you know more about pop culture than I do.  The inner workings of LG and the processes we use to deliver our stories to you each week is what we can talk about, so if you’re curious, read on!

On to this week’s questions!

Question from Chris:

Jacek, I’m super curious to know how you felt about Lainey’s gossip work in the early days. And at what point did you realize it was a real, career, money making opportunity? I assume Lainey realized it first, just wondering about the dynamics of your conversations as partners, when and how you came to the decision to switch careers and support the site full time, all that good stuff. We all know Lainey is super lucky to have you, I’m just really interested in your perspective of how her career, and therefore yours, has grown and evolved!

Jacek’s Answer:

Two things pinged me right away when I read the first line of this question, and it was the “gossip work in the early days” part that resonated but in different ways. 

First it was the career part of the question. Most of you reading this piece know Lainey’s backstory so I won’t go into the long details, but LaineyGossip started out as a newsletter. She was the office pop-culture gossip guru at her previous job and when she left, she started writing the newsletter purely as a passion and as a way to keep in contact with her friends who always enjoyed her takes on Hollywood. One thing led to another and the blog happened, and soon after that she was getting inundated with tips, interview requests, sponsorship asks, television gigs, and ad agencies looking to help monetize a site that was launched ad-free initially. 

Lainey in Canadian Business in 2006

So it became pretty clear pretty quickly that this was going to be our best chance to make some money and potentially have fun while doing it. I was in a job that was no longer fulfilling and had finished my degree while working not long before then, and I was ready for something new as well.  Taking on all the administrative elements of our new company and making decisions for ourselves was super exciting. This let Lainey re-focus entirely on what she did best without bogging her down with accounting, paperwork, client calls, ad tech, etc. 

I’ve been doing that ever since and that was 2007 when I finally left my day job, and looking back it’s been the job of a lifetime for us to have run our own business and kept it going this long. It’s been so great to experience directly and through the person I love all these far-from-normal things like seeing her carry the Olympic torch, covering the Oscars and the Super Bowl, writing a bestseller, the list goes on. My role has changed only slightly over the years and I’ll touch on that in a later question, so from a career perspective I have no doubt chosen to prioritise her path over mine in the sense that she’s “outside” (as Kathleen pointed out to me the kids say these days) and I’ve remained behind the scenes, but this also suits our personalities. She is the peacock and I’m a natural homebody, so in that sense it has been a perfect sharing of roles.

The second way in which that question pinged me was that since 2020 especially, when I see the words “early days” of the site my hackles go up a little bit. Again, if you follow this newsletter or our site, you’ll know that our writing has changed A LOT over the last 15 years, and a lot of our older content was by today’s standards (and some even by THAT day’s standards) hard to read. Unlike Lainey who had to face the criticism publicly, I’ve probably never fully reconciled with how that whole experience impacted us and her, specifically. Because I was behind the scenes, I harbour a degree of guilt that I wasn’t able to shield her from the vitriol and hate that was thrown at her when she faced up to that old content. I’m her business partner but her husband first and I wanted to throw the gloves on. “But, but, but…..”. Needless to say my approach would have been a lot less gracious than hers in terms of how she dealt with our old “sins”. I had seen her evolve and own up to the old stuff for quite a long time prior to the “outing” that occurred, as did many of our long-time readers based on the feedback and emails we got in support. So I just felt like screaming from the mountaintops that it was not fair and we had already addressed our shittiness for years.  I wanted to fight. Obviously, that wouldn’t have been the right thing to do and I am proud of how Lainey set a standard for how to own your mistakes and try to be better. It was so courageous and strong and I admire her for it greatly. The measured, rational part of me knows it was the only way forward. But I still dream of getting in the face of the people who orchestrated that outing and having little chat.

Questions from Caitlin M and Pankie:

Who is skimming all of our insane emails?! Emily, are you sending along piecharts to Lainey & Sarah showing the amount of people onside with TNT vs. those who wish they would get a room? Or is it a vibe check

and …

Emily - When/ how often do you review your editorial calendar with Lainey and Sarah? There are tent pole events and seasons, so those remind me of other industry edit calendars. Do you have calendaring process - post-its on the wall? Software? Do you ask the writers for themes for the year? Is there a lid on how many articles per day? Do you collaborate with the writers on how best (productive) to incorporate/ launch new sections, like Maria's Celebrity Social Media? Would LOVE to hear more about how you do your work!!

Emily’s Answer:

I am skimming the insane emails! You should see the one we got yesterday. Both Lainey and I have access to her lainey@laineygossip email address and we see the emails as they come in in real time. I will flag and forward anything that needs to be addressed right away such as invites, notifications for important or exclusive photo sets I know she and Sarah will care about, relevant concerns from readers, etc. A lot of what comes into that mailbox are alerts from our various photo agencies, PR releases – that kind of thing, and I delete those after a couple of days so our inbox doesn’t get clogged up. We don’t get as many emails from readers as we did a few years ago, and I’m sure some of this is because we can now let it all out at The Squawk. My Hate Mail folder has seen some things, I’ll tell you that.

To answer the second part of this question, I think people would be surprised at how little Lainey and I actually communicate with each other throughout the week. We email every day and throughout the workday, but phone calls don’t happen often. She has so much going on every day and one of the most important things I can do each day at LG is to help things go as seamlessly as possible, and this means bugging her as little as possible! I want to lessen her load, not add to it.

Team OG LG.

That said, of course there are times during the year when more planning and strategizing is necessary, like award shows, TIFF, and certainly when we were launching The Squawk.

There isn’t an official cap on number of articles per day, but we absolutely have to gear down for award shows, which is why you see celebrities grouped together in a lot of those pieces. Otherwise it would be a 30-article day. We used to do it that way and it was madness.

There are no post-its and there is no software! I’m a list guy myself and I use those to keep myself organized, but almost everything within our team that I’m involved with is done via email, including communication with our writers.

Question from JC:

What kind of stats do you track, in terms of LG website traffic, and what can we understand about LaineyGossip readers from them? How many people visit the site every day? Is there a particular time of day when we're all getting our gossip fix? Are there insane spikes in readership around events like the Met Gala or the TNT Superbowl? What was the most read post in the past 12 months?

Jacek’s Answer:

I use Google Analytics and Google Ad Manager to keep tabs on our traffic, ad delivery, revenue, etc.  Those tools do show you what people are reading, for how long, how many of them, and pretty much anything you want to pull about your site traffic. The update to Analytics is less robust IMO than the original that was just shuttered, but it still gets us some basic insights into what people are reading. There are definitely times when traffic spikes like when a big story hits or during awards show coverage. This is when readers who are aware of us but not daily gossips check in to see what we’re saying.

The data helps us understand trends, but we’ve never used that site data to determine what we want to write about. Lainey has always taken a story-first approach to deciding what goes up and the same is true for Sarah when she edits. I do share wins when a particular article does well, but over the last few years that has become more dependent on whether or not a post of ours gets picked up in Google’s Discover or how well it’s positioned in Google News. And when those tools do drive visits to those featured pages, they tend to dwarf the numbers that other articles are getting viewed that day. 

But for the sake of having some fun here, year to date these are the top read articles on LG so far:

1)      Bennifer: A Silent Anniversary

2)      Bennifer Zillow

3)      Our Intro for February 7, 2024 about Drake’s ‘penis leak’

4)      Bennifer Friday

5)      Bennifer Weekend

Notice a trend?

But again, all of these were a result of Google’s algorithm loving our Bennifer coverage. The sixth story on this list was one about a Henry Cavill role in Guy Ritchie’s film, so it can also be a bit random. But if I were to generalize and take out these algorithm anomalies, the articles that get the most comments and attention are exactly the ones you’re thinking. Beyoncé. The Sussexes. My GOD, the Sussexes. Bennifer. Buckingham Royals. Angelina Jolie.   And of course Taylor Swift.

Which leads perfectly to the next question and I know Emily will want a say here too….

Question from JenC:

What is a take of Lainey’s on a particular celebrity or a scandal or a scenario that you disagree with? Let’s stir the pot lol

Jacek’s Answer:

I don’t get Lainey’s obsession with Rihanna. She’s great and don’t come for me please, because I admire a woman who has built a mega empire and lives her life, but to me she gets a lot more praise on LG than she deserves. And of course, going back a way, I never understood why she was so into Gwyneth. Lainey, too, would probably look back at that and cringe (and has?) at her fawning over the woman, but really, is there a person who is less deserving of all the admiration she received on this site than 2005-2015 Gwyneth Paltrow?

Lastly, Lainey used to pick on Emmy Rossum all the time. No idea why. Probably it was that smile. I always found her to be HOT AS FUCK even when she was the butt of a lot of Lainey’s jokes on LG.  Never understood it and Emmy, call me.

HOT! Emmy Rossum at Apple TV+ 'The Crowded Room' Limited Series Premiere, New York, USA - 01 Jun 2023 (Gregory Pace/Shutterstock)

Emily’s answer:

We’re really doing this? Fine, but if I’m fired after this, it’s your fault.

I’m not falling all over myself for Beyoncé. I recognize and respect her talent, of course, and I like her music, but the obsession isn’t something I understand. Apologies to Lainey, Kathleen, and probably Duana.

Agree with Jacek on Gwyneth. I always thought that was weird. She is not someone to be admired, in my humble opinion.

Having said that, I think Rihanna deserves all the praise she gets on the site and more, JACEK.

Question from Myra:

Jacek - do men gossip about celebrities in the same way that women do? Emily - how much of the site content is planned in advance vs written last minute? J&E - if you had a magic wand how would you evolve LG?

Jacek’s Answer:

My group chats with my boys are disgusting and immature and we say shit we would NEVER say publicly. I’m sure everyone is the same. I’m pretty progressive and aware of the culture mainly, though, and I have to be if I’m to survive the feminist stronghold that is LaineyGossip and The Squawk, but I also like to poke fun at Lainey telling her I feel “triggered” when she says something benign or that she is “gaslighting me” when she claims she told me to buy the Almond Milk I forgot to get.  

To answer the celebrity part more directly, mostly my buddies and I gossip about sports. There’s a lot of gossip in sports as we know. And your question about evolving LG I’ll address below.

Emily’s answer:

I almost want to say that this is more a question for Lainey and Sarah than it is for me, because truthfully, I don’t always know how much of the content is written in advance vs. planned, I just know that when it’s sent to me, it’s time to edit and post!

On Thursday evenings, Sarah will send the first draft of the lineup for Friday, which is often edited/added to at least twice by Friday morning, and I wake up on Fridays with most of the day’s pieces in my inbox, give or take a couple. Regardless, I have a pretty clear idea of what the day looks like and how I should be timing my day and spacing out articles.

Monday – Thursday are, um, not as organized, but Lainey and I have been doing it this way for going on 15years (where did the time go? They grow up so fast!) and it works! Because her day on the site is often determined by her ETALK (and formerly The Social) schedule, mine is as well. She writes when her schedule allows and sends me each article as they are written. I know my day is going to start sometime between 5 and 6AM Pacific Time, but there is often no way to predict when Lainey will be able to get the next piece to me. 

As for the magic wand, The Squawk has been such an incredible evolution for us and I love the sense of community it’s brought to my work and to our team. At this moment, I can’t imagine anything better than being able to have these thoughtful and hilarious conversations with all of you.

Question from Lexi:

Jacek and Emily … what did y’all do before LG? Curious about your CVs and am too lazy to look you up on LinkedIn 😂

Jacek’s Answer:

I’ve done LG for SO long now that we’re going back quite a few years. I was a manager in the Rogers Call Centre in Burnaby when I left for LG full time. This is where I met Lainey, who also worked for Rogers at the time, as a corporate trainer. I managed the group of people you would get if you wanted to escalate your issue to a manager or director. Before that I was in a couple of other managerial positions and prior to those worked the phones myself for quite a few years while going through school. I worked in a sporting goods store coming out of high school and into university. 

Emily’s Answer:

My first “real” job was in the music industry at a record label/management when I was in my early 20s. I was working at Starbucks and interned at Nettwerk to get my foot in the door for six months before I was hired. I worked there for three and a half years – first in the merch department and then digital marketing - and then worked as office manager and front desk for a renewable energy company. It wasn’t at all what I wanted to do, but it was a paycheque while I was in limbo. Truthfully, what I wanted to do was work for Lainey. I had been a fan of the site, a daily reader since my Nettwerk days, and I knew through email that we had a good rapport. And then one day it fucking happened.

Question from Laura:

Question for Jacek: What exactly is your role behind scenes? And as the internet landscape is forever changing, what steps do you take to keep up with the changes? Like how did the evolution to Substack come about? Why were other choices like patreon not taken?

Jacek’s Answer:

In simplest terms it’s to take care of all the non-editorial elements of what we do with a couple of exceptions. 

Editorially, I curate and cut the article summary teaser videos you see that dock to the bottom right of the desktop site or the top of the mobile site. I also edited the podcasts we once did. And of course when Emily is off, I do the posting, which involves pulling the photos we need from our various agencies, resizing a labelling, posting and editing the articles, creating meta titles and descriptions for SEO, and maintaining Squawk chats. I also shoot and edit most of the paid Instagram content we create when we partner with brands, and take care of all the administrative elements of running those campaigns including getting legal terms finalized, copy drafts prepared, and reports and invoices complied and sent.

The non-editorial stuff consists of compiling, analyzing, and auditing all of our different ad vendors revenue reports from the previous day and making required adjustments based on how bids are performing, day to day accounting and bill payments, managing our PR, ad and photo agency relationships, keeping on top of SEO and privacy trends (mostly with a whackload of google alerts but I also jump on webinars and calls offered by, for instance, our Consent Management Platform about changes and updates). I’m also the first point of contact for Emily when something happens to the site, which I’ll either deal with myself if it’s simple enough or get our server admin or developer involved if we have to. We don’t have the budget to staff those folks but instead have them on a retainer and pay hourly when stuff gets done. 

In terms of the more “visible” contributions I’ve made over time, the design of LaineyGossip.com that you see today was mostly my work. I initially contracted out to a design firm when we needed to update the site and they came back with stuff that was so far off what we needed in spite of what we had discussed, that rather than spend MORE money hoping someone else came back with something good, I decided to give it a shot myself.  I used Adobe Photoshop and XD to create mocks, my web developer sliced it up and programmed it, and we launched RIGHT when the pandemic hit! Yay!

I also brought forward the idea of launching The Squawk, which is the second part of your question.  For years we had this disconnect where we wrote this highly personal diary-style summary of pop culture but never meaningfully interacted with our readers. We talked for years about launching a comment section but never did for many reasons we’ve discussed before. I was also seeing how the ad tech industry was eating off its arms and taking publishers’ limbs with them as privacy regulations were tightening without a decent alternative in place, so we had to find a way to supplement and expand beyond ad revenue to keep doing what we were doing. I knew that our friends Heather and Jessica over at Go Fug Yourself (subscribe to Drinks with Broads!!!) had launched a Substack and got their feedback about what they experienced, and it seemed like the perfect fit. And it truly has been.

As for why Substack? It’s built for writers and publishers first and foremost. Patreon offers a lot of functions around video that Substack is only expanding into, but the paid support layers were simpler for what we were looking to do and I read feedback that with Patreon, the layering of paid-add-on benefits and having to deliver this graduated, granular offering really made things complex and added pressure to deliver those benefits.  Substack seemed simple and seemed to check so many boxes for us, including the ability to post those informal daily chats that are so alive each day. 

This seems like a perfect jumping off point and I’ll address Myra’s question from earlier about how we’d like to evolve LG if we had a magic wand. The Squawk is one of those steps in that evolution.  We believe writers, content creators of every kind, should be paid for what they do. For so long we got used to things being “free” on the internet and never gave much thought to how it was paid for.  It was always paid for by the data that was shared by the big platforms, app makers, and websites about your browsing habits so that ads could be placed in front of you that were interesting and relevant to you.  All this is started getting turned on its head resulting in unsustainably low ad digital rates across the industry, so pay-for-access is starting to become the norm on the internet and small sites are shutting down. 

So my magic wand would put in place a structure that maintains this “free” and open internet while allowing entities to thrive other than the giant, greedy platforms who claim to have your privacy first and foremost in mind (looking at you first, Apple, but also Google and Meta). You should have the choice to whether or not you’d rather pay for what we create or offer up meaningful and useful data so advertisers you want to see can reach you without having that decision be made for you by default by these self-serving giants who mostly just do these things to cut each other’s knees off and to keep tunnel-visioned legislators off their backs.  Without that, I see LaineyGossip and a lot of other sites our size eventually either shutting down or scaling back, or becoming paywalled, gated, very intimate places that are mostly found through sharing and word of mouth and not on the open internet.  

Sad as that sounds, it’s a very broken industry right now but we’re trying and so are other publishers who rely on your support, whether that’s allowing targeted ads (never mind not using blockers!) or paying a bit for access to the sites you care most about. 

There are other things we want to do, creative projects we have on the go behind the scenes that may or may not come to fruition, but mostly we’d love to keep giving you guys a place to gossip about celebrities in a forum that isn’t shat on by trolls that have no interest in meaningful discussion, so we’re really grateful for this space and your participation in it.  

It’s renewal season for many of you and I know we’re beating you all over the head with requests to keep supporting us, but if you enjoy LaineyGossip.com or The Squawk or both, please know that by getting a paid subscription to the Squawk you’re supporting both sites.  All of our work. 

Squawk often,

Jacek and Emily