Making LinkedIn Weird: A Conversation with Jillian Richardson

Every time I open LinkedIn I lose a little bit of faith in humanity.

Not because people are bad. Because everyone sounds exactly the same.

Humble. Grateful. Excited to announce. It's like someone cloned a management consultant 50 million times and gave them all WiFi.

So when I got Jillian Richardson on Messy Growth, the woman arguably responsible for more personality on LinkedIn than the rest of us combined, I had a lot of questions. Some of them sharp. Some of them probably annoying. All of them worth asking.

Here's what I took away.

How "Make LinkedIn Weird" actually started

It wasn't a brand strategy. It was a rant.

Jillian was working at a content agency writing 200 LinkedIn posts in two months for founders. A genuinely insane amount of content that no human should ever have to produce. What she noticed was that the funny posts performed the best. And they were also the posts founders were most terrified to publish.

When she left that job she wrote a post almost off the cuff. "Hey, we should make LinkedIn weird." Hadn't posted in over a year. It went viral. Forbes. Business Insider. And suddenly she had a business.

The lesson: sometimes the thing you say for yourself resonates most with everyone else.

The ghostwriting question nobody asks directly

I pushed her on this one.

You help C-suite executives sound human. Isn't there something fundamentally broken about manufacturing authenticity on behalf of someone else?

Her answer was better than I expected.

Ghostwriting done properly isn't about making up thoughts for someone. It's about extraction. You sit down, you ask questions, you pull the good stuff out of their brain and put it into a format they'd never sit down and create themselves. The thoughts are theirs. The discipline and craft is hers.

The danger, she said, is when the ghostwriter's voice doesn't match the client's personality. She's worked with someone in supply chain. Dry industry, dry guy. If she wrote for him the way she writes for herself, he'd lose every client the moment they got on a call and realized the content sounded nothing like the actual human.

Authenticity in ghostwriting isn't about who wrote it. It's about whether someone meets you in real life and thinks "yeah, that tracks."

The gap between how executives see themselves and how they come across

This one was interesting.

Most senior people assume they need to share deep, profound industry expertise because they're surrounded by other experts all day. They forget that the most basic advice, the stuff they consider embarrassingly obvious, can genuinely blow someone's mind if that person isn't in their world.

Jillian calls it the 101 series. What's the thing in your industry you'd be almost embarrassed to post because it feels too basic? Post that. It's probably your best content.

The closer you are to something the harder it is to remember what it was like not to know it. Which is exactly why the people who just figured something out are sometimes better teachers than the people who've known it for twenty years.

Is "weird" just safe positioning?

I asked her directly: weird as a brand is extremely safe. It signals individuality without committing to anything specific. Is Make LinkedIn Weird actually weird, or just weird-adjacent?

She laughed. Then she made a good point.

Go to a party and mention LinkedIn. The reaction you get is: "Ugh, that place is so stuffy and boring and professional." That's what normal LinkedIn is. Weird LinkedIn is just normal. Talking like a human being. Having an opinion. Maybe making someone smile.

The bar for weird on LinkedIn is genuinely that low. Which tells you everything you need to know about the platform.

The loneliness thread

This was the moment in the conversation that surprised me most.

The Joy List. Hustle Fest. Make LinkedIn Weird. I pointed out that there's a loneliness thread running through everything she's built.

Turns out she wrote a book about it. Unlonely Planet, about creating community outside of organized religion. Loneliness has been the biggest struggle of her life. And like a lot of people who build things around a painful topic, she's built her entire career trying to solve the thing that's hardest for her personally.

She called it the wounded healer. The thing that hurts you the most becomes the thing you dedicate yourself to fixing. I thought about that for a while after we finished recording.

Key takeaways

Look, I walked away from this conversation with a few things rattling around in my head and I figured I'd share them because they're worth sitting with.

The posts that scare you the most are usually the ones you should publish. Every founder Jillian worked with was terrified of the funny stuff. Those were the posts that went viral. Fear is not a stop sign here. It's actually pointing you in the right direction.

Ghostwriting is not what you think it is. Nobody is sitting there making up thoughts on behalf of some executive who has nothing to say. The good ones are extracting what's already in your head and putting it in a format you'd never sit down and create yourself. If your ghostwriter is inventing your opinions, you hired the wrong person.

Your obvious is someone else's breakthrough. The stuff you think is too basic to post, the stuff that feels almost embarrassing because surely everyone knows this already, that's often the content that connects most. Because they don't know it. That's literally why they're following you.

Stop treating LinkedIn like it requires a personality transplant. Talking like a normal human being on that platform is apparently so rare it's considered weird. That's genuinely insane. And genuinely an opportunity.

Frameworks worth stealing

The envy-disgust matrix

I love this one because it's actually useful and not just a fancy name for common sense.

Jillian tells her students to map two things. First, whose content makes you jealous? Like you look at it and think "damn I wish I posted like that." Move toward that. Second, whose content makes you cringe so hard you'd rather quit LinkedIn entirely than post something similar? Move away from that.

Your personal line sits somewhere in the middle. Nobody can tell you where it is. You have to figure it out yourself by actually posting things and seeing how it feels.

The 101 to 401 stack

Most executives only ever post at the advanced level. Deep expertise, nuanced takes, industry jargon that only the inner circle understands.

The 101 stuff, the basic foundational things they'd be almost embarrassed to say out loud because it feels too obvious, that's usually the content that reaches the most people and builds the most trust. Your audience is not all experts. Most of them are trying to get to where you already are.

Earn the right to optimize

Three videos in and you're already researching thumbnail psychology. Ten LinkedIn posts in and you're reading books about hook formulas.

Stop. You cannot optimize a system that doesn't exist yet. Post fifty times. Have a thousand sales conversations. Get two hundred customers. Then look at what's broken and fix it. The optimization conversation only makes sense after you've actually built something worth optimizing.

Quotes worth keeping

These are the lines I'm still thinking about a week later.

The parts of myself I judged the most ended up being the things that made me successful.

That one I had to sit with for a minute honestly.

Your personality, your story, your insights, what makes you different, that's the only thing you have in the age of AI.

If I ask someone questions about themselves and they can't answer them, ghostwriting isn't going to work. You have to know who you are first.

And this one is the simplest thing she said but probably the most actionable.

Publicly ask for what you want. It's a cheat code and almost nobody uses it.

Rapid fire round

Same questions every guest. No prep. No warning. Here's how Jillian handled it.

Best advice you've ever received? Ask other people what they're doing. Sounds simple. It isn't. When you actually hear that real people are charging certain rates or trying certain things, your brain stops treating it as some scary abstract concept and starts treating it as something you can do too. Changed her whole approach to pricing.

Advice you wish you'd listened to? Don't overshare early on. She was writing deeply personal essays, putting everything out there, thinking that vulnerability would make her more comfortable in her own skin. It doesn't work like that. Turns out discernment is something you have to earn through a few cringeworthy mistakes first.

What would you tell your younger self? "The parts of yourself you judge the most will end up being the things that make you successful." She said this like she'd thought about it a thousand times. Probably has.

Ongoing challenge that keeps you up at night? Long term planning. Two months from now she genuinely has no idea what's coming in. From the outside it looks effortless and fluid. From the inside it's just a very well disguised version of the same uncertainty everyone else has.

Favorite spot in New York? Bathhouse or Othership in Flatiron. Saunas, cold plunges, group screams and a gong. I asked zero follow up questions because honestly what would I even say to that.

Tool you can't live without? Gamma. Deck creation software. She did a paid post for them and still uses it every day. That's the real endorsement right there.

One piece of advice for someone starting out? Publicly ask for what you want. Post it. Say it out loud. Most people are too scared to do it, which is exactly why it works for the ones who do.

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Jillian Richardson is the founder of Make LinkedIn Weird, a ghostwriter, certified coach, and Amazon bestselling author. Find her on LinkedIn.