This week’s lesson: Playing it safe can make you invisible. Invisibility is the enemy of creativity, leadership, and revenue.

Over the last few weeks, a snippet has been living rent-free in my head. It’s from Alex Karp, co-founder and CEO of Palantir, from his book The Technological Republic.

The piece is called “The Disapproval of the Crowd”, and in it, Karp writes:

“We have today privileged a kind of ease in corporate life, a culture of agreeableness that can move institutions away, not toward, creative output.”

He describes the “impulse—indeed rush—to smooth over any hint of conflict” as misguided. And he quotes comedian John Mulaney’s line: “Likability is a jail.”

That one stopped me because it points to a structural constraint in companies. The need to be liked is not just a personality trait but a structural constraint. It shapes how people behave, what risks they take (or avoid), and what ideas are worked.

And Alex is right. The most interesting founders, artists, and ideas are often a bit chaotic, a bit wild, and a bit difficult. They care more about the work than how it lands socially.

What resonated most with me was the tension experienced in most teams:

• We crave ease and approval → but real creation requires friction and resistance.

• We admire rebels and artists → but rarely want to manage or work alongside them.

It reminded me of something Rory Sutherland wrote and one of my favorite quotes to reference:

“It is much easier to be fired for being illogical than it is for being unimaginative. The fatal issue is that logic always gets you to exactly the same place as your competitors.”

Karp and Sutherland point to the same trap: We’ve overoptimized for likability and logic—for fitting in, being polished, and not rocking the boat. In doing so, we’ve made it harder to say something original, to do work that’s different, to take creative risks that don’t come with pre-cleared justification.

There are times when you shouldn’t have pre-cleared justification.
Pre-cleared justification kills creativity.

Every company says they want innovation, but very few are willing to make space for the friction that actually leads to it.

Without tension, weird ideas, or a little chaos, you get the same answers everyone else has already found.

So maybe the goal isn’t to be liked. Maybe it’s to be honest. Brave. Even a little strange.

Because “smooth” doesn’t change the game. But a little friction might.

♥️Kyle

Thanks to Share Your Genius, who is our first partner in the newsletter and podcast. I’ve known the team and their CEO for years. They are the best creative agency, helping brands build deeper relationships with their audience through binge-worthy podcasts and great content.

On Social Anxiety, Events, and Alcohol

I walked into a networking event last month and immediately scanned the room for the bar… not to drink, just to stand near it.

You know the feeling…

Something about holding a drink, even if it’s just club soda with lime, helps me blend in. It gives my hands something to do, and it makes me feel like I have a reason to be there.

Before I stopped drinking, this would’ve been a non-issue. I would’ve had a beer in my hand in five minutes and been deep in a conversation ten minutes later. Not because I was naturally comfortable. But because alcohol helped me bulldoze through the social anxiety I didn’t want to admit I had.

When I wrote about hitting six months without alcohol, I talked a lot about physical benefits… better sleep, more energy, mental clarity. But one thing I only scratched the surface of was this: social anxiety.

It’s wild how long I lived with it without naming it. I was never the life of the party, but I liked to have fun. I liked being around people. I liked being liked. For a long time, I thought that meant I was extroverted. But looking back… 

I wasn’t comfortable in those settings—I was just buzzed. Half the reason I drank was to take the edge off those moments. 

The low hum of awkwardness before a conversation starts. The flood of thoughts after you say something and immediately wonder how it landed.

Alcohol quieted all of that. It muted the noise just enough to feel like I belonged. Or at least to stop caring if I did.

Now, without it, all those feelings are front and center. That “edge” I used to take off? It’s still there. And now I need to learn how to carry it, not ignore it.

So it feels like starting from scratch when I’m standing in a room full of strangers with a soda water and lime, trying to work up the courage to say hi to someone I don’t know. And honestly? It’s kind of terrifying.

But it’s also real.

There’s no false confidence. No foggy memory of what I said. No second guessing whether I came off too strong or too quiet or too whatever. There’s just me… anxious, imperfect, and still showing up.

And that’s the part I’m starting to be proud of.

Because every conversation I have now is earned, every interaction is something I had to push through discomfort to get to. 

I still hate small talk. I still get nervous before events. I still rehearse what I will say while pretending to check my email. But I’m doing it. And I’m doing it sober.

That counts for something.

On DMs, AI, and the Art of Not Fumbling the Hand-Off

I’ve been following Sol Rashidi’s work for a while now.

She’s smart and credible, sharing some of the most thoughtful takes on AI in marketing. So when I got a LinkedIn message from someone reaching out on her behalf, I was actually interested.

Which is rare for a cold DM. But then… it got weird.

The first message said someone on my team had contacted Sol about one of her publications.

That caught my attention. I didn’t remember anyone doing that, but hey, maybe someone did?

So I replied: “Who from my team?” They answered. Kind of.

“Hey Kyle, We saw our LinkedIn analytics, and employees from your company were in the engagement demographics for Sol's posts. Happy to setup a chat with her if it can be helpful as you go about scaling Al across your workforce and solutions.”

It turns out the message was based on LinkedIn analytics. A few folks from my company had engaged with Sol’s content, but no one had actually reached out.

And just like that, the story shifted. What started as “you contacted us” turned into “we saw some data and decided to pitch.”

That may seem small, but it changes the entire dynamic. It turns a warm lead into a credibility issue.

A quick note on “behalf” outreach…

I have no problem with someone reaching out on behalf of a founder or executive. It can be efficient and thoughtful when done right.

But be upfront. Say who you are and why you’re reaching out. Don’t build the message around a shaky premise to create false urgency.

This one felt like it was working overtime to justify the outreach. Just be real. I already follow Sol. You don’t need a hook if the person’s already paying attention.

They missed an opportunity to be human and relevant… 

First, the follow-up was loaded with credentials: IBM Watson, 200-plus AI deployments, and Big 4 consulting experience. All impressive. But none of it was connected to what I actually do.

I’m not at a consulting firm. I’m not deploying Watson. I’m running marketing and go-to-market inside a SaaS company trying to scale with focus.

Impressive doesn’t mean relevant.

Second, I replied and said, “I’m a huge fan of Sol.” That’s not subtle. That’s an open door.

Instead of stepping through with a human reply, the message stayed formal. Third person. Scripted.

If someone says they’re a fan, don’t send them a polished bio. Just talk to them like a person.

Here’s how I would have rewritten it… 

Hey Kyle - Saw a few folks from your team engaging with Sol Rashidi’s AI content on LinkedIn, and thought I’d reach out.

Sol’s been working with CMOs and growth leads on practical ways to use AI, especially around content velocity, personalization, and cutting through the hype.

Since you already follow her work (and clearly get it), I figured I’d offer to set up a quick chat in case you’re thinking about it this quarter.

Totally up to you.

– Sarah (On Behalf of Sol) 

See the difference? It starts honest, tailors the message to the recipient, and keeps it human. I would've respected the approach even if I had passed or ignored the message. 

I’m still a fan of Sol and think her work is top-notch. But the outreach failed because it wasn’t clear, relevant, or real.

If you’re going to reach out to someone, especially someone who already likes what you’re doing? Don’t fumble the handoff.

On Figma’s Slides Launch and What We Can Learn

We don’t usually think of presentations as beautiful. Or emotional. Or inspiring. Most of the time, they’re the thing we survive to get to the actual conversation.

That’s why I was so surprised when I watched the launch video for Figma Slides.
From the first frame, it didn’t feel like a product demo.

It was enjoyable. 

No “Here’s a better way to make slides.” No feature dump.
Just: This is what it could feel like to build ideas together.

The video showed the product, sure. But more than that, it told a story—a story about collaboration, design, and putting something out of your head and into the world with other people.

And that’s what great marketing does. It doesn’t just tell you what a product does. It makes you feel like it was made for you.

Figma’s campaign isn’t just good. It’s a reminder that even a category as tired as “presentations” can be reimagined if you lead with emotion, if you lead with the human… not features.

It left me asking:  What are the stories we’re telling around our work?
And are they good enough to make someone feel?

So, what should we learn from the launch and the video? 

Lead with feeling, not functionality. Figma didn’t open with a feature list. They recreated a situation we’ve all experienced.

Create movement, not just a message. The positioning isn’t “a better way to present.” It’s an invitation to rethink the whole experience of sharing ideas.

Design your campaign like you design your product. Every video frame is crafted with the same precision and intention as the product itself. Don’t ever underestimate the value of brand consistency. It builds trust.

Speak to the frustration and then show the freedom. Everyone has felt boxed in by clunky slide tools. Figma didn’t say, “We fixed it,” they showed what it feels like when the box disappears.

Say less, make them want more. The video is short. The product walkthrough is light. But somehow, I get it. And I want to see more.

Figma reminded me: If you want someone to adopt your product, don’t just explain it. Make them feel like they’ve been waiting for it.