Wes Kao is an executive coach, advisor, and entrepreneur who writes at newsletter.weskao.com. She is co-founder of Maven, an edtech company that raised $25M from First Round and Andreessen Horowitz. Previously, she co-founded the altMBA with bestselling author Seth Godin.

Newsletter for 60,000+ high performers on Wednesdays at 8am ET
-> weskao.com/newsletter

Live, 2-day course on Executive Communication & Influence 
-> https://maven.com/wes-kao/executive-communication-influence

1:1 executive coaching for tech leaders 
-> https://www.weskao.com/coaching

Wes Kao

Excited to be featured in Lenny Rachitsky’s “The AI-Native Product Manager” series. I’ll be teaching a free workshop on the topic “how to get buy-in as a PM.”

Of the 1,700 tech operators who have taken my course in the past 1.5 years, product managers are one of the biggest groups represented. About 1/3 of my private coaching clients are product leaders at companies like Meta, DoorDash, Atlassian, Amazon, Google, etc. I love working with product folks, and want to help you succeed because the bar for PMs is getting increasingly higher.

In this session, I’ll cover how to:

1. Present to impatient executives: Be prepared to move fast, speak directly, etc.

2. Manage up to senior leaders: Most PMs suck at managing up. We'll cover principles that will serve you now and throughout your career.

3. Anticipate questions and prevent skepticism: How to anticipate questions to avoid endless back-and-forth.

You will be able to apply these principles to stakeholders upwards, downwards, and laterally. 

The workshop will be on Friday, March 13 at 12pm ET. It will be an action-packed 30 minutes.

I rarely do free workshops, so if you’ve been curious about my course or found my Lenny podcast episode helpful, I hope to see you there.

Sign up link is in the comments.

a16z-backed founder turned executive coach. Helping tech operators improve their executive communication, leadership, and influence

Acquiring Inbound Leads for B2B Founders with Personal Content Programs • Explaining Content, one Ugly Drawing at a time

Content steals focus, I know. Writing, formatting, visuals, posting cadence, and keeping up with comments. It becomes a weekly tax, then it gets dropped, then inbound stays unpredictable.I build an Authority Engine for B2B Tech Founders. It turns your existing knowledge into consistent content that makes you look like the category leader, without you writing a word.What you get:1) 100% custom AI voice cloneWe extract your voice from your real materials. Whitepapers, sales calls, internal docs, Slack messages, past posts, and anything else that reflects how you think and speak. No generic templates.2) LinkedIn Autopilot5 high converting posts per week, ghostwritten, formatted, and ready to publish. You do not write, format, post, or search for visuals. You approve drafts with a simple yes or no.3) Search Dominance pack2 SEO optimized long form articles per month, derived from your LinkedIn content, so your authority compounds beyond the feed.First week of content can go live within 48 hours of onboarding. You can see engagement on day 1. Your only job is approvals.I will write 3 posts for you for free using your data, so you can see the voice match before you pay. If the first week does not sound exactly like you, or better, I rewrite it until it does, or you do not pay.Best for founders who have real insight and a real product, but do not want content creation to compete with building, selling, and hiring.If you want to test the voice clone, message me: “3 posts”.

Kuba Czubajewski

IMO, this is the only realistic "future" of content marketers:

Every week, I see here new tools popping up that promise my clients they can let all their content team go because AI can do it all for them.

Not once have I seen it actually work, btw.

Content is a much deeper thing than writing a bunch of paragraphs that sound good or an infographic that looks nice.

For me, it's all about connecting the dots that are usually VERY far apart and turning it into a fresh, impactful message.

This is why I'm in love how Dropbox Dash is approaching AI for creatives.

Instead of proposing yet another "I'll do it for you" tool, they're solving one major pain most of us feel:

Not being able to connect the dots because the dot you're looking for is in a file you forgot the name of.

Sounds trivial, but OH MY GOD, the amount of time I used to spend on scrolling through my G-drive is embarrassing.

And this is where I think the whole AI for content conversation should land.

AI is incredible at recall.

Humans are still the best at judgment what matters, what’s true, what’s new, and what’s worth saying out loud.

You won't win because you can generate 50 posts a day.

But if you can pull the right inputs fast, then make a call on the angle, and ship a message people actually remember, you will win.

PS. this is not sponsored by anyone, I just saw their launch and loved it.

I’ll write 3 LinkedIn posts for free, in your voice. If it sounds like you (or better), we install your AI Authority Engine in 90 days.

I started with no money, no contacts, no fancy city office.

Picture this:

A small apartment in Poland.
No team.
Nothing to “show off.”
No one backing me up.

Every day – me, my laptop, and clients who didn’t know my name.

Most days felt like:

Write posts.
Wait.
Hope for an inbound lead.

(Usually nothing.)

B2B tech leaders... yep, tough crowd.

I’m creative, talkative, maybe too much for some.

Every call made me sweat.

Every pitch was incredibly awkward.

Sometimes I wondered if I was nuts for picking this path.

But I couldn’t quit.

I learned to spot what they really needed.

I tried new ideas - most failed, a few worked.

I worked with scraps.

Fixed broken things.

Built trust, one honest message at a time.

I got used to hearing “no.”

I got used to waiting.

But I kept sending, kept building, kept showing up.

Then, slowly...

A “maybe.”
A client who said, “you get what we need.”
A few more.

Then referrals.

All because I'm too stubborn to stop.

Now, I help B2B teams turn strangers into real leads.

One content system, built from scratch.

Starting with nothing makes you sharp.

You learn what matters FAST.

If you feel lost in your work, or your niche feels impossible, keep at it.

Your “weirdness” or “wrong fit” could be the thing they need most.

PS. What did you learn from your first clients when you started from zero?

No alternative text description for this image

Here's a 10-min flow I use with founders to create weeks of content for them:

The goal is to create one small, high-integrity narrative object that can survive multiple contexts without losing its meaning. 

The easiest way to do that is to start with a 10-minute CEO video (use Tella or Loom), because spoken answers preserve something writing tends to bleach out: conviction, nuance, and those small qualifiers that signal real experience. 

I beg you, don’t ask for “thought leadership.” 

Ask one tight prompt that forces specificity, like what buyers are getting wrong about a problem right now, what that misunderstanding costs them, and what they should do instead.

Once you have the Loom, the extraction step matters more than the editing. 

You’re looking for a structure:

Pull out:

- one contrarian claim that creates tension
- one vivid symptom that makes the claim relatable
- one constraint that makes it believable
- one before/after framing that makes the shift obvious
- one proof detail that anchors it in reality

That proof detail can be lightweight. It can be “we heard this on 12 calls this month,” or “this showed up in every deal we lost last quarter.” 

Now you take those five ingredients and you write one “source paragraph” in plain language. Don't think of any platform yet. 

Just articulate the idea clearly as if you were explaining it to a smart friend over coffee. This paragraph becomes the anchor. Every other asset is a translation of it, not a reinvention. That’s how you keep integrity when you repurpose.

From there, I like to create three outputs that each do a different cognitive job:

First, a short text post that opens with the contrarian claim and immediately explains the symptom. 

The mistake people make is opening with the claim and then drifting into abstraction. Don’t. 

Earn the reader’s trust by describing what they already see in the wild, the call snippets, the internal debates, the marketing copy that “sounds right” but doesn’t move anything.

Second, a simple carousel where each slide is a single unit of meaning. Not “tips,” but progression. The before model, the cost of that model, the constraint that keeps people stuck, the after model, and then one practical move they can try this week. 

If you can’t fit the idea on five slides without it turning into fog, the idea isn’t ready yet.

Third, a longer form piece where you unpack the constraint and the proof detail. 

This is where nuance belongs. Why the obvious fix fails. What tradeoff you’re making. What to watch out for. 

This is also where you can safely include a real example, even if it’s anonymized, because you have space to set context.

Two quality checks before you hit publish:

• If the post could apply to any company, it’s too generic. 

• If the reader can’t repeat your point in one sentence, it’s too complicated.

If you want, reply with your niche and I’ll give you 5 tight CEO prompts that reliably produce these “weeks of content” anchors.

I recently changed my banner to this one below and you might think I went insane:

This is not a typical path content people choose for their businesses.

“Free value” beyond a regurgitated ChatGPT lead magnet is a rare thing here.

My thinking is this:

I built an Authority System for copying B2B founders’ voice with AI.

It’s GOOD. Took me about a year to get here. 

And the easiest way to prove it is to show my potential clients how it works.

Yes, building a sample assistant is harder than posting fancy carousels and “vulnerable” fake-ass stories

But I’ve always been more of a show-don’t-tell kinda guy and not planning to stop now.

Curious how it works? Dm me “3 posts”

"comment on other creators' posts" is sh!tty advice:

I used to spend 2 hours per day here commenting on probably all of them big creators.

Most of them don't give a rat's a*s about me or my content.

And that's perfectly fine. Why would they?

Not once have I reached out to them in a DM, they have no reason to see my comment and think:

"I wonder what this guy is about?"

But the folks I exchanged DMs with are consistently showing up under my posts.

Because we established a more meaningful connection than a [put an insightful comment here so they see you're trying hard]

See what I'm getting at?

Connection > tactics.

Build the first one and you'll never need to think about the second one again.

A year ago I thought I had it figured out:

Build a content agency for B2B founders. Use AI to do the heavy lifting. Keep costs low, scale fast. Simple.

What actually happened: 

I spent months building something nobody wanted to pay for.

The first version of the system was basically:

1. take the founder's old posts
2. dump them into a prompt
3. generate something that kind of sounded like them

The output was fine. Technically competent. The kind of content that gets 15 likes and zero leads.

I wasn't impressed with myself tbh. Neither were my clients.

So I overcomplicated everything:

A 12-step onboarding process, 5 different content formats, a pricing page that looked like a software feature comparison matrix...

I was trying to cover every possible use case for every possible client, and the result was that nobody could figure out what I actually did.

The solution was so stupidly simple, I facepalmed when I finally got there:

I started interviewing founders instead of just ingesting their existing content.

Turns out the best content a founder can publish isn't what they've already written.

 It's what they say when someone asks them the right questions:

- the unguarded takes
- the specific stories
- the things they'd never think to write down but say out loud constantly

Once I built the system around that – extract the thinking first, then write – the output stopped sounding like AI trying to be human and started sounding like the founder on their best day.

That took about a year to nail.

The offer got simpler too:

Interview you -> Write it up -> Publish it -> You approve the drafts. 

That's the whole thing.

If you want to see what it looks like, DM me "3 posts" – I'll write them for free before you spend anything.

I had a chat with a B2B founder that told me he struggles with referrals because his clients "can't explain his value." Here's how I'd fix it with content:

When clients can't explain your value, it usually means one of three things:

1/ You solved a problem they didn't know they had.

2/ You fixed something so complex they can't see the full scope.

3/ You delivered value that's invisible until it breaks.

Your content needs to make the invisible visible.

Instead of writing about what you do, write about what breaks when you're not there.

"What happens when your data pipeline fails during your biggest sales quarter"
"The hidden cost of manual processes that only surface when you try to scale"
"Why your competitors can respond to market changes faster than you"

This type of content does two things:

1/ It helps prospects recognize problems they didn't know they had.
2/ It gives current clients language to explain why those problems matter.

When clients forward your content about "hidden operational risks," they're not just sharing an article.

They're explaining why they needed you without having to understand the technical details.

Your content should make the case for your category of work, not just your company.

The better prospects understand the problem you solve, the easier it becomes for clients to refer you.

A thing we rarely discuss in marketing is how customers perceive our narrative through preloaded meanings:

We think we’re publishing a simple story about a benefit. They’re interpreting a signal about power, intent, and control. 

That gap is what Ring ran into with its Super Bowl ad about a lost dog found through a neighborhood camera network. The creative aimed for warmth and community. 

The audience, already saturated with years of privacy discourse and surveillance headlines, watched the same 30 seconds and didn’t primarily evaluate the plot. They evaluated the infrastructure implied by the plot. 

“AI + cameras” isn’t a neutral prop anymore. It’s a symbol, and symbols arrive with cultural baggage attached.

This is the real mechanism behind “losing the narrative.” It’s rarely about execution quality but about the interpretive surface area. 

When a story leaves room for people to fill in the blanks, they will. And they’ll fill them with the strongest available frame in their mind, usually the one that best matches their anxieties. 

In this case, the counter-frame was waiting in the wings, mass surveillance disguised as safety. 

Once that frame establishes itself, everything that follows stops being “new information” and becomes “supporting evidence.” 

That’s why Ring’s sudden move away from a planned partnership with Flock Safety was immediately absorbed into the same storyline. Regardless of internal motives, it read like validation, not coincidence.

The takeaway isn’t “be careful with your messaging.” That’s too shallow. 

The takeaway is that narrative is not a message you transmit. It’s a negotiation between your intent and the audience’s prior beliefs. 

And prior beliefs are not something you overcome with a nicer tone. They’re something you have to design around. If your product or campaign touches an area where trust is already fragile, you should assume your audience will run an adversarial interpretation, even if they like you, even if the ad is well made.

A better move is to treat messaging like you treat product design:

Reduce ambiguity. Anticipate misuse scenarios. Make the boundaries legible. 

Don’t just tell a heartwarming story about what your system can do at its best. Show that you’ve thought seriously about what it could do at its worst, and what you’ve done to prevent that. 

In 2026, “we’re doing this for safety” is not a persuasive claim by itself. People want to know who gets visibility, who gets veto power, and what recourse exists when the system is wrong.

Curious how you think about this. When was the last time you watched a brand’s “feel good” story and immediately felt the darker subtext the audience would attach to it?

Quick tip if you hate when AI says "It's not X, it's Y..."

This rhetorical device is called "contrastive reframing using antithesis structure."

Hard-prompt it into your content assistant to avoid it (example below).

Also, from my tests, Claude 4.6 is much better at this that GPT models.

PS. Let me know any other annoying things AI uses - I'll show you how to remove them from the outputs.

How I helped a B2B consultancy business (very niche) start showing up in AI search:

We focused on turning their LinkedIn content into long-form SEO articles built around real opinions, specific frameworks, and language that maps to actual buyer problems.

AI tools cite sources that are clear and substantive. Since their LinkedIn content had this already, expanding it into articles became much easier.

The results measured over the last 90 days:

Overall: 1,619 AI bot hits → 4,163. That's 3x.
Homepage: 514 → 946. Almost 2x.

Every hit is ChatGPT or Perplexity pulling from their site while a buyer is actively researching. That's pipeline you'd never see in a cold outreach report.

If you want to see what this looks like for your niche, reply ENGINE and tell me what you sell.

200,000 people just watched a creator get stood up by a brand's AI chatbot:

Reformation used AI to manage its influencer outreach. It confirmed a collaboration, set up a store visit, and ran weeks of back-and-forth with a creator.

She drove an hour to the store, shot video in the dressing room... The manager had no idea who she was.

TikTok called it "an AI bot that went rogue." Reformation sent her a sweater as an apology.

Here's my read on what actually happened: 

AI made commitments nobody at the brand had authorized. And no human was watching the inbox it was running.

The bot did exactly what it was built to do - respond, confirm, follow up. 

But nobody told it where to stop. That's a systems failure.

AI doesn't know when it's overstepping. The tool runs until you build a stop - and plenty of AI marketing setups skip that step entirely.

There are places where automation works well: segmentation, sequences, content drafts.

And then there are contexts that require a human in the seat: real commitments, real relationships, anything a creator or partner will hold you to.

I put a lot of emphasis on that while working with my clients on their content assistants.

First draft can (and should) come from the AI. But the human editor before anything goes live is a must. 

Doesn't matter how good your AI tool is. If there's no one monitoring what it's agreeing to, you're one post away from a mess.

The CEO of impact put it well: "Human credibility becomes more valuable, not less."

That's the thing marketing teams running AI tools aren't accounting for right now, imo.

taplio

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Wes Kao

Kuba Czubajewski

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taplio

The Battle

Wes Kao

Kuba Czubajewski

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Wes Kao's LinkedIn Performance

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Performance ScoreWes Kao's LinkedIn Performance