What we learned from our CEO's week-long marketing takeover

What does a CEO do when his head of marketing goes on vacation? Apparently, stage a full-blown LinkedIn mutiny.

It started as a joke. I was in Turks and Caicos — a trip we'd planned for over a year — and Josh decided to "prove marketing isn't that hard." So, he posted asking for everyone's worst marketing ideas. The comments exploded with suggestions like hiring your cousin to run social media and turning off HubSpot.

What he didn't expect? I had Wi-Fi. And a LinkedIn addiction that probably needs slight professional attention.

By Monday night, Josh had bought imsorryjess.com, hand-coded a website outlining every chaotic suggestion, and added a lead capture form on there to give away our swag. He shipped hundreds of Marketers Against Humanity decks from his garage with handwritten notes — no fulfilment plan, no pipeline, no regrets.

By the end of the week, he'd learned his lesson — marketing is kinda hard — and wrote a grovelling apology post which later got him cancelled. He really had a week.

But amongst it all, that spur-of-the-moment stunt became the moment our brand spilled over onto LinkedIn — and into real life. It was a total accident, and it worked.

In this episode, we unpack what happened, why it worked, and what it taught us about taking risks in B2B marketing.

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What you'll learn:

• Why the best marketing moments are often total accidents
• How Josh’s LinkedIn stunt turned our podcast dynamic into a recognizable brand
• Why most B2B marketing is boring — and what to do about it
• The case for posting from personal pages instead of your company page
• How to tap into your audience's sense of humor (yes, even engineers have one)

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TOP THREE TAKEAWAYS

Takeaway 1: Your brand is built in the moments you don’t plan

We'd already recorded Season 1 of the podcast. We had chemistry, but it lived inside the show — people who listened got it, but it hadn't broken out beyond that.

Then Josh decided to "overthrow" me while I was on vacation. I had no idea it was coming, and it took what we'd been building on the show and brought it to LinkedIn in the most organic way possible.

Josh leaning hard into the "CEO who thinks he can do marketing" trope. Me in the comments from a pool in Turks and Caicos, desperately pleading people to stop (with a cocktail in hand). It was chaotic, unscripted, and people loved it.

It snowballed. And somewhere along the way, people realized this wasn't just a podcast bit — this was the brand. Now we go to trade shows and people recognize us. They reference it. They say, "Oh my god, it's Josh and Jess!"

The lesson? You can't manufacture these moments. But you can create the conditions for them, by building something real, having fun with it, and letting your personality show up in public.

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Takeaway 2: Ideas are easy, execution is the hard part

By the end of the week, Josh had learned his lesson. And not in a cute, “oh well” kind of way. He genuinely realized marketing is harder than he thought.

It's easy to have a creative idea. The LinkedIn post went viral — the website was funny and the swag giveaway got hundreds of form fills. But none of those leads had converted as quickly as Josh thought they would.

Coming up with something clever isn't the job. Turning it into something that actually captures demand is. Ideas get the attention, execution gets the results.

Josh thought marketing was just ideas. Turns out, they actually have to work.

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Takeaway 3: Your people are your best distribution channel

This whole thing worked because it came from real people. Josh on his personal page, being chaotic. Me in the comments reacting in real time from a pool in the Caribbean. That's what people connected with.

LinkedIn's algorithm has made it harder for company pages to get organic reach. But even beyond the algorithm, people connect with people. A post from your founder will almost always outperform the same post from your company’s page.

If there's one thing to take away from this, it's to start leaning into your people as the deliverers of your campaigns, your ideas, your narrative. Let them be the voice. Your company page still has a role, and it should be to amplify your people's content.

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So, what did we actually learn from Josh’s week-long mutiny?

We didn't set out to create a defining moment for our brand. Josh wanted to mess with me while I was on vacation. But sometimes, that's all it takes — a bit of chaos, a willingness to try something different, and Wi-Fi in the Caribbean.

The whole thing was an accident. No strategy doc. No campaign brief. Just Josh being Josh, me panicking from a pool, and hundreds of people tagging me in the comments. And yet, it worked better than anything we could have planned.

Most B2B marketing is boring because people are afraid to take risks. But here's the thing: you're probably not going to break your brand by having a little fun. So stop overthinking it. Try something. See what happens.

And maybe don't overthrow your marketer. But if you do — at least hand-code the apology website.

Catch the full episode (and subscribe to This Meeting Could’ve Been a Podcast!) on YouTube or your favorite podcast platform.