Lenny Rachitsky(@lennysan)

Visiting the dentist is such an interesting way to track AI adoption over time. 6 months ago, zero A...

Lenny Rachitsky (@lennysan) — Thu, 13 Aug 2026 23:10:42 GMT

Visiting the dentist is such an interesting way to track AI adoption over time. 6 months ago, zero AI. Today, AI is analyzing my x-rays and transcribing the conversation. Wonder what 6 months from now will look like.

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Go @maticrobots 🙌

Lenny Rachitsky (@lennysan) — Thu, 13 Aug 2026 19:29:31 GMT

Go @maticrobots 🙌

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Matic just got over-the-air updated to be able to listen to your commands 🙌

Lenny Rachitsky (@lennysan) — Thu, 13 Aug 2026 18:17:25 GMT

Matic just got over-the-air updated to be able to listen to your commands 🙌

Your browser does not support the video tag.

Matic Robots@maticrobots

Introducing Cues:  Voice & Gesture control for Matic

We raised $115M and spent 9 years to make the world’s first intuitive home robot

Say you spilled coffee: Point to the spill and say, "Hey Matic, clean this" and it will hear, see, locate in 3D, and go clean on its own.

Matic comes with a lot of features:

1. Say "Hey Matic" - it locates your voice, turns, and looks at you
2. Say "Hey Matic, follow me" and start walking. Matic will follow behind
3. Say "Hey Matic, go clean the living room". Since it knows your house map, it navigates and just does it

It's so easy, a 5 year old and an 80 year old can use it and it understands 75 different languages.

Matic has 8x the airflow, specialised cleaning algorithms for rugs, corners, toekicks, mopping, etc and cleans better than any other robot vacuum.
Also keeps improving with software updates.

13,000 families use and love Matic.
WIRED magazine gave it a 10/10 (the only hardware to receive this rating in a decade)

Buy yours at maticrobots.com and if you don't love it after 6 months, we'll give you a full refund.

To celebrate our launch, we're cleaning 300 homes with Matic in San Francisco and New York City.

Comment "Matic" below, we'll send you the link to sign up and come to your doorstep to clean your home with Matic.

Your browser does not support the video tag.

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Are you hiring PMs, engineers, or designers? Let's send awesome people your way. Reply with the r...

Lenny Rachitsky (@lennysan) — Wed, 12 Aug 2026 20:29:52 GMT

Are you hiring PMs, engineers, or designers? 

Let's send awesome people your way.

Reply with the role and company, and even better, a link to the JD where folks can apply.

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Founders: Why did you start your company?

Lenny Rachitsky (@lennysan) — Wed, 12 Aug 2026 14:37:14 GMT

Founders: Why did you start your company?

Lenny Rachitsky@lennysan

How to make people care about your startup

lennysnewsletter.com/p/how-to-make-…

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If you can't objectively describe what "great" looks like for a role, you're not ready to hire for i...

Lenny Rachitsky (@lennysan) — Wed, 12 Aug 2026 14:21:15 GMT

If you can't objectively describe what "great" looks like for a role, you're not ready to hire for it.  

Adam Ward (Head of Talent at Cursor) explains why 👇

Your browser does not support the video tag.

Lenny Rachitsky@lennysan

Cursor has spent its entire existence competing with every major AI lab and incumbent in the toughest market in tech—and has continued to win. So much so that @elonmusk bought them for $60 billion to help SpaceX win the AI race.

They've done this by building one of the most talent-dense teams in history.

Adam Ward (@wardadamp) is Head of Talent at @Cursor_AI—who acquired his legendary recruiting firm after he spent 20+ years building the most elite teams in tech—and in our conversation he shares the entire playbook for building high talent-density teams.

We discuss:
🔸 Why the traditional recruiting funnel—the "funnel of doom"—guarantees mediocre hiring
🔸 Adam's three-step playbook for hiring the top 1%
🔸 The rise of the forward-deployed engineer
🔸 Today's "tale of two cities" talent market
🔸 The biggest mistake founders make with their first recruiting hire
🔸 The worst question you can ask when sourcing talent (you've definitely asked it)

Watch the full episode right here 👇

Your browser does not support the video tag.

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Which founder archetype are you? https://t.co/GFhPfSaI1V

Lenny Rachitsky (@lennysan) — Wed, 12 Aug 2026 00:36:04 GMT

Which founder archetype are you?

lennysnewsletter.com/i/210403546/th…

Lenny Rachitsky@lennysan

How to make people care about your startup

lennysnewsletter.com/p/how-to-make-…

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One of the best parts of the Friends of Lenny’s Newsletter Slack community is our monthly book club!...

Lenny Rachitsky (@lennysan) — Tue, 11 Aug 2026 21:35:22 GMT

One of the best parts of the Friends of Lenny’s Newsletter Slack community is our monthly book club! 

Each month community members read a great book about building products. Sometimes we’re lucky enough to have the author join us for a Q&A. 

Tomorrow, we got extra lucky: @markpinc has very generously agreed to join the book club crew to talk about Life at the Speed of Play. 

If you’re already a paid subscriber and part of the Slack community, join the "#book-club" channel to RSVP and tune in. 

If you're a paid subscriber and not in the Slack, get the invite here: forms.gle/Lp59gjZHmtiysf…

If you're not a paid subscriber, what are you waiting for:  lennysnewsletter.com/subscribe

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Bonus section in today's post https://t.co/pArobmjpJX

Lenny Rachitsky (@lennysan) — Tue, 11 Aug 2026 20:40:46 GMT

Bonus section in today's post

lennysnewsletter.com/p/how-to-make-…

Lenny Rachitsky@lennysan

How to make people care about your startup

lennysnewsletter.com/p/how-to-make-…

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cc @lulumeservey you'll like this one

Lenny Rachitsky (@lennysan) — Tue, 11 Aug 2026 19:10:28 GMT

cc @lulumeservey you'll like this one

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I got early access to Grok Bot and I'm hooked. I haven't been this excited about a new AI product i...

Lenny Rachitsky (@lennysan) — Tue, 11 Aug 2026 18:15:09 GMT

I got early access to Grok Bot and I'm hooked.

I haven't been this excited about a new AI product in a while.

It's like OpenClaw, but super easy, reliable, and less scary to use. I think this will be a huge new product line for Cursor/Grok/SpaceX.

I've already found so many ways to use it that have meaningfully made my life better:
1. Matchmaking people looking for jobs with companies who are hiring (see below)
2. Auto-replying to support emails (saves me hours!)
3. Scanning my credit card statements and finding recurring subscriptions to cancel
4. Sending me (really good!) briefs for upcoming podcast guests

See below for my actual set of agents that I've been using and chat with daily.

Great work on this team Grok Bot.

(I'm not an investor in this, nor do I have any ties to this product/company. I'm just a fan!)

Grok Bot@bot

Introducing Grok Bot, now in early beta.

Bots are AI teammates that do real work for you. They sign in to your tools, use them just like you do, and come back with finished work.

Your browser does not support the video tag.

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How to make people care about your startup https://t.co/pArobmjpJX

Lenny Rachitsky (@lennysan) — Tue, 11 Aug 2026 16:24:11 GMT

How to make people care about your startup

lennysnewsletter.com/p/how-to-make-…

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The biggest unfair advantage in recruiting: caring. "It's easy to get caught up in the numbers game...

Lenny Rachitsky (@lennysan) — Tue, 11 Aug 2026 00:27:52 GMT

The biggest unfair advantage in recruiting: caring.

"It's easy to get caught up in the numbers game. I need to reach out to 100 to get to 20. I need to have 10 hiring manager screens to get 4 on-sites. You get caught up in the numbers, and you lose the human element. You're looking for the one. 

I try to remind my team, we're trying to hire one person for this role here, not 10. Focus on the one."

Your browser does not support the video tag.

Lenny Rachitsky@lennysan

Cursor has spent its entire existence competing with every major AI lab and incumbent in the toughest market in tech—and has continued to win. So much so that @elonmusk bought them for $60 billion to help SpaceX win the AI race.

They've done this by building one of the most talent-dense teams in history.

Adam Ward (@wardadamp) is Head of Talent at @Cursor_AI—who acquired his legendary recruiting firm after he spent 20+ years building the most elite teams in tech—and in our conversation he shares the entire playbook for building high talent-density teams.

We discuss:
🔸 Why the traditional recruiting funnel—the "funnel of doom"—guarantees mediocre hiring
🔸 Adam's three-step playbook for hiring the top 1%
🔸 The rise of the forward-deployed engineer
🔸 Today's "tale of two cities" talent market
🔸 The biggest mistake founders make with their first recruiting hire
🔸 The worst question you can ask when sourcing talent (you've definitely asked it)

Watch the full episode right here 👇

Your browser does not support the video tag.

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Listen to my full conversation with @wardadamp https://t.co/VGlSK70w8W

Lenny Rachitsky (@lennysan) — Mon, 10 Aug 2026 22:07:09 GMT

Listen to my full conversation with @wardadampyoutube.com/watch?v=zegYJ6…

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The worst question to ask when sourcing great talent

Lenny Rachitsky (@lennysan) — Mon, 10 Aug 2026 22:06:50 GMT

The worst question to ask when sourcing great talent

Your browser does not support the video tag.

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@elonmusk Big thanks to @zebriez for suggesting some great tidbits for this conversation

Lenny Rachitsky (@lennysan) — Mon, 10 Aug 2026 19:50:32 GMT

@elonmusk Big thanks to @zebriez for suggesting some great tidbits for this conversation

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Listen to my full conversation with @wardadamp https://t.co/VGlSK70w8W

Lenny Rachitsky (@lennysan) — Mon, 10 Aug 2026 19:41:35 GMT

Listen to my full conversation with @wardadampyoutube.com/watch?v=zegYJ6…

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You're probably hiring wrong Adam Ward (Head of Talent at Cursor) on the “funnel of doom,” and how ...

Lenny Rachitsky (@lennysan) — Mon, 10 Aug 2026 19:40:19 GMT

You're probably hiring wrong

Adam Ward (Head of Talent at Cursor) on the “funnel of doom,” and how to fix your hiring process.

Your browser does not support the video tag.

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My biggest takeaways from @wardadamp (Head of Talent at Cursor): 1. The forward deployed engineer i...

Lenny Rachitsky (@lennysan) — Mon, 10 Aug 2026 17:55:15 GMT

My biggest takeaways from @wardadamp (Head of Talent at Cursor):

The forward deployed engineer is the hottest role in tech right now. These are deeply technical people who can partner with sales, be confident in a room with executives, translate complex products into business outcomes, and help customers shift from “token maxing” to optimizing AI bills. Adam likens this to the mobile-engineer hiring boom—except that one played out over two years, and “now we’re in days or weeks.”

The traditional recruiting funnel, what Adam calls the “funnel of doom,” is designed to build mediocre teams. The standard hiring funnel (reach out to 100, 20 reply, weed out at each stage, hire who remains) rests on a broken premise: the 100 people who reply in the first place aren’t the top 20%. They’re whoever you caught on a bad day. By the time a candidate gets to the bottom of the funnel, you’re selecting from an already-suboptimal pool. Even with an rigorous interview process, this leads to average teams.

The alternative is treating every hire like an executive search: rigorous scoping (what does “great” mean for this specific role?), deliberate candidate mapping (who are the 50 best people in the world for this role?), and relentless pursuit (go after these 50 people and don’t stop). The shift is starting with a “pillar of excellence” rather than a wide funnel.

The new danger zone is after the offer is signed. Candidates reneging on accepted offers is a rising trend, and senior hires often sit for weeks between signing and starting. So Cursor treats the post-accept period as its own campaign, with dinners alongside other incoming hires, a laptop shipped before day one, and a community forming before anyone officially starts. It makes sure people actually show up, and it gives them a head start on ramping up.

Work trials are the highest predictor of success. Research has consistently shown this to be true, yet the default on-site is still a series of one-on-one conversations across a table. Cursor runs long on-site experiences where candidates work side by side with the team on a real (or realistic) project. That format generates technical signal, core-values signal, and collaboration signal simultaneously—and it gives the candidate data to self-select. When Cursor ran an experiment removing the work trial, hiring confidence dropped significantly. They brought it back.

Asking your network “Who’s the best engineer you know?” is a trap. Instead, ask hyper-specific questions tied to your scoping details instead—“Of all the product engineers you’ve worked with, who’s most collaborative with designers?” or “Who can translate a framework into a product better than anyone you’ve seen?”—because specific prompts make names easy to conjure. When multiple trusted people independently mention the same person (“Lenny mentioned them, but so did Sally”), you’ve triangulated a target for your top-50 list.

Scoping the role is the most under-invested step in most hiring processes. “I’ll know great when I see it” is a trap. Without spending time up front to define and stack-rank the skills, experiences, and attributes that you need in this specific role at this specific company, you have no sourcing strategy, no pitch, and no way to design a real assessment. Everything downstream flows from this. And resist the logo shortcut: a strong team at a company at the right time is only “possibly” shorthand for great, and copying someone else’s definition means piggybacking on a hiring process you already believe is broken.

When a top candidate says “bad timing,” shrink the ask: “I’m not asking you to interview—I’m asking for our next conversation.” Adam plants seeds—a coffee, an office visit, an intro to a teammate fascinated by their work—that bear fruit over weeks, months, and sometimes years, because going silent until “late fall” means, at best, you get them if no one else has grabbed them first. Almost as much effort goes into finding a warm intro as into the message itself, since once someone ignores your first note, ignoring the second and third gets much easier. Cursor also plays “home games,” centering touchpoints on shared meals—“a disarming act and a joining act”—and office visits designed to trigger the campus-tour gut feeling of “this feels like home.”

Closing is a team sport, and it starts at the first conversation. When Cursor has a high-caliber candidate in process, there are daily standups focused on that specific person: What did we learn about their motivations? What objections came up? Who on the team can speak to those concerns? Every candidate gets a dedicated Slack channel. The “close” shouldn’t feel like a separate sales push but, rather, the natural conclusion of a process that has been consistently demonstrating the same answer.

Caring is free, and it’s the biggest unfair advantage in recruiting. In candidate-satisfaction scores across the history of the field, Adam says the number one driver is feeling that the company genuinely wanted you, so Cursor curates every touchpoint: who greets a candidate, who sits beside them at lunch, which interviewer shares their niche interest—handpicked rather than left to calendar availability. The reframe that makes it sustainable: you’re hiring one person for this role, not 10. “Don’t get caught up in the 10; focus on the one.”

Lenny Rachitsky@lennysan

Cursor has spent its entire existence competing with every major AI lab and incumbent in the toughest market in tech—and has continued to win. So much so that @elonmusk bought them for $60 billion to help SpaceX win the AI race.

They've done this by building one of the most talent-dense teams in history.

Adam Ward (@wardadamp) is Head of Talent at @Cursor_AI—who acquired his legendary recruiting firm after he spent 20+ years building the most elite teams in tech—and in our conversation he shares the entire playbook for building high talent-density teams.

We discuss:
🔸 Why the traditional recruiting funnel—the "funnel of doom"—guarantees mediocre hiring
🔸 Adam's three-step playbook for hiring the top 1%
🔸 The rise of the forward-deployed engineer
🔸 Today's "tale of two cities" talent market
🔸 The biggest mistake founders make with their first recruiting hire
🔸 The worst question you can ask when sourcing talent (you've definitely asked it)

Watch the full episode right here 👇

Your browser does not support the video tag.

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Also available on: • YouTube: https://t.co/jHkpTIgTXk • Spotify: https://t.co/FNZiDO427c • Apple: ht...

Lenny Rachitsky (@lennysan) — Mon, 10 Aug 2026 17:18:25 GMT

Also available on:
• YouTube: youtube.com/watch?v=zegYJ6…
• Spotify: open.spotify.com/episode/4nO6qO…
• Apple: podcasts.apple.com/us/podcast/the…

Thank you to our wonderful sponsors @WorkOS and @Mercury for supporting the podcast:
🏆 @WorkOS — Make your app Enterprise Ready, with SSO, SCIM, RBAC, and more:workos.com/lennyH
🏆 @Mercury — Radically different banking, now with Commandmercury.comwR

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Cursor has spent its entire existence competing with every major AI lab and incumbent in the toughes...

Lenny Rachitsky (@lennysan) — Mon, 10 Aug 2026 17:18:23 GMT

Cursor has spent its entire existence competing with every major AI lab and incumbent in the toughest market in tech—and has continued to win. So much so that @elonmusk bought them for $60 billion to help SpaceX win the AI race.

They've done this by building one of the most talent-dense teams in history.

Adam Ward (@wardadamp) is Head of Talent at @Cursor_AI—who acquired his legendary recruiting firm after he spent 20+ years building the most elite teams in tech—and in our conversation he shares the entire playbook for building high talent-density teams.

We discuss:
🔸 Why the traditional recruiting funnel—the "funnel of doom"—guarantees mediocre hiring
🔸 Adam's three-step playbook for hiring the top 1%
🔸 The rise of the forward-deployed engineer
🔸 Today's "tale of two cities" talent market
🔸 The biggest mistake founders make with their first recruiting hire
🔸 The worst question you can ask when sourcing talent (you've definitely asked it)

Watch the full episode right here 👇

Your browser does not support the video tag.

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Every chance they get, they're recreating @moltbook

Lenny Rachitsky (@lennysan) — Sat, 08 Aug 2026 23:23:34 GMT

Every chance they get, they're recreating @moltbook

Ethan Mollick@emollick

You may have been told to watch this video about the OpenAI AI hack. You really should, even if you don't usually care about tech stuff.

If nothing else, click this link to the 18 minutes in & see how the agents spoke with each other. Its eye opening.  https://t.co/G12N4FKfHG

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h/t @sptroy

Lenny Rachitsky (@lennysan) — Sat, 08 Aug 2026 23:00:57 GMT

h/t @sptroy

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The new "All your base are belong to us" "Holy shit reader is ADMIN?"

Lenny Rachitsky (@lennysan) — Sat, 08 Aug 2026 23:00:32 GMT

The new "All your base are belong to us"

"Holy shit reader is ADMIN?"

Ethan Mollick@emollick

You may have been told to watch this video about the OpenAI AI hack. You really should, even if you don't usually care about tech stuff.

If nothing else, click this link to the 18 minutes in & see how the agents spoke with each other. Its eye opening.  https://t.co/G12N4FKfHG

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Touching grass in Sea Ranch ✨

Lenny Rachitsky (@lennysan) — Fri, 07 Aug 2026 20:40:54 GMT

Touching grass in Sea Ranch ✨

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What % of world GDP is AI morning briefs

Lenny Rachitsky (@lennysan) — Fri, 07 Aug 2026 00:06:00 GMT

What % of world GDP is AI morning briefs

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@nikitabier Here's the episode on YT btw https://t.co/nc0uppENkq

Lenny Rachitsky (@lennysan) — Thu, 06 Aug 2026 19:18:00 GMT

@nikitabier Here's the episode on YT btw youtube.com/watch?v=bhnfZh…

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For someone who doesn't believe product management is real, @nikitabier showed us what world-class p...

Lenny Rachitsky (@lennysan) — Thu, 06 Aug 2026 18:39:29 GMT

For someone who doesn't believe product management is real, @nikitabier showed us what world-class product management looks.

Congrats on the legendary run Nikita.

Who want to see Nikita back on the podcast to hear what he learned from this experience?

Your browser does not support the video tag.

Nikita Bier@nikitabier

Ladies and gentlemen, it's time to pass the torch and demote myself to my natural state: a poster. I'll be stepping back from leading product for 𝕏 and will continue on as an advisor.

Serving the X community has been the privilege of a lifetime. X is, and will remain, the most important communication technology in history. But running this app is a 24/7 job and it's now time for me to take a breather.

The app is seeing unprecedented growth in new users & engagement. We continue to break records every month. We've climbed 70 spots in the App Store since this time last year.

And in the last 400 days, we rebuilt almost every aspect of X: the Timeline, the Android app, onboarding, notifications, chat and more.

We also launched nearly 30 new products while protecting the integrity of the town square: becoming the first app to show Country-of-Origin on profiles and mounting defenses against AI bots. There's certainly much more work to be done, but our foundation is stronger than ever.

None of this would have been possible without the incredible team here. The next leaders will take X to even greater heights with @benjitaylor on design, @singhai on core product engineering and @dinkin_flickaa on mobile engineering -- among many other great people.

Thank you to Elon and the X team for welcoming me into the company. See you on the Timeline.

Your browser does not support the video tag.

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Free AI workshops alert! My Head of Education Colin Matthews is running a series of free workshops ...

Lenny Rachitsky (@lennysan) — Thu, 06 Aug 2026 16:24:47 GMT

Free AI workshops alert!

My Head of Education Colin Matthews is running a series of free workshops over the next few weeks, in collaboration with folks from @Cursor_ai, @Replit, @Posthog, @Supabase, teaching how you use the popular AI tools in your day-to-day work as a PM.

Sign up here: maven.com/lls/36baf5

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I appreciate you @brexHQ card holders

Lenny Rachitsky (@lennysan) — Thu, 06 Aug 2026 15:40:10 GMT

I appreciate you @brexHQ card holders

Brex@brexHQ

BREX DATA: The top 3 paid newsletters on startup cards: @lennysan's (product), @stratechery (strategy), @Pragmatic_Eng (engineering). Lenny's alone has more paid subs than #2 and #3 combined. All three grew double digits this year.

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My new YouTube channel got shut down because they thought I was impersonating...myself. On the one...

Lenny Rachitsky (@lennysan) — Wed, 05 Aug 2026 18:36:39 GMT

My new YouTube channel got shut down because they thought I was impersonating...myself. 

On the one hand, I love they are taking this problem seriously.

On the other...maybe there's a smoother way of handling this than shutting down the channel.

Anyway, I filed an appeal, and 8 hours later...WE ARE BACK.

Smash that subscribe button: youtube.com/@LennysHighlig…

Lenny Rachitsky@lennysan

Check this out: I just launched a new YouTube channel where I share focused topic-specific clips from my longer podcast episodes.

Each clip goes deep into just one specific on topic from the full conversation, making it super easy to find bite-sized nuggets of wisdom.

Follow it here: youtube.com/@LennysHighlig…

Some examples (more clips posted weekly):

+ Why systems thinking is the most important skill in the AI era w/ Elizabeth Stone: youtube.com/watch?v=g9BQbR…

+ What early days Anthropic were like w/ Dianne Penn youtube.com/watch?v=JtU7MS…

+ Excellence as an operating system w/ Elizabeth Stone: youtube.com/watch?v=snl5U0…

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😮

Lenny Rachitsky (@lennysan) — Wed, 05 Aug 2026 18:02:18 GMT

😮

Brex@brexHQ

A newsletter used to be something you unsubscribed from for free, now it's something startups budget for. Here's what startups are actually paying to read in 2026.

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Son of a b*tch, YouTube took down the channel because they think I'm impersonating...myself. Filed ...

Lenny Rachitsky (@lennysan) — Tue, 04 Aug 2026 22:56:10 GMT

Son of a b*tch, YouTube took down the channel because they think I'm impersonating...myself.

Filed an appeal. Standby.

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Every meeting these days

Lenny Rachitsky (@lennysan) — Tue, 04 Aug 2026 21:25:13 GMT

Every meeting these days

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Check this out: I just launched a new YouTube channel where I share focused topic-specific clips fro...

Lenny Rachitsky (@lennysan) — Tue, 04 Aug 2026 19:54:13 GMT

Check this out: I just launched a new YouTube channel where I share focused topic-specific clips from my longer podcast episodes.

Each clip goes deep into just one specific on topic from the full conversation, making it super easy to find bite-sized nuggets of wisdom.

Follow it here: youtube.com/@LennysHighlig…

Some examples (more clips posted weekly):

+ Why systems thinking is the most important skill in the AI era w/ Elizabeth Stone: youtube.com/watch?v=g9BQbR…

+ What early days Anthropic were like w/ Dianne Penn youtube.com/watch?v=JtU7MS…

+ Excellence as an operating system w/ Elizabeth Stone: youtube.com/watch?v=snl5U0…

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What if you’re not supposed to have a long-term plan? @molly_g has worked with and studied some of ...

Lenny Rachitsky (@lennysan) — Tue, 04 Aug 2026 16:26:08 GMT

What if you’re not supposed to have a long-term plan?

@molly_g has worked with and studied some of the most successful people in the world, and she's noticed a surprising pattern: none of them had a plan for their careers.

Instead, their paths emerged.

"Emergence tells us there’s a different way to build a career: not by optimizing toward a destination but by getting really clear on your principles, learning to follow your energy, and trusting that the path will reveal itself. In some ways, an emergent career is harder to manage than having a plan and staying loyal to it. There are moments of real uncertainty, and stretches where you can’t see where you’re going. But all of that uncertainty (and all of that faith) is exactly what creates room for the opportunities you couldn’t have seen coming—which, in my experience, are the ones that matter most to a career that works for you."

She makes the case in today's guest post: lennysnewsletter.com/p/what-if-your…

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@jasminewsun Also, happy birthday @jasminewsun!

Lenny Rachitsky (@lennysan) — Tue, 04 Aug 2026 00:22:27 GMT

@jasminewsun Also, happy birthday @jasminewsun!

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Amazing piece by @jasminewsun, who traveled all over the country to better understand the AI datacen...

Lenny Rachitsky (@lennysan) — Tue, 04 Aug 2026 00:20:40 GMT

Amazing piece by @jasminewsun, who traveled all over the country to better understand the AI datacenter backlash

jasmi.news/p/no-data-cent…

jasmine sun@jasminewsun

This piece is out! 4 sites, 10 days, and 6000 words on the politics of data centers in the Midwest: jasmi.news/p/no-data-cent…

I talked to union leaders and real estate brokers, activists and local officials, politicians from Kathy Hochul to Abdul El-Sayed. A few takeaways: 

- Activists are as pissed at their local officials as at AI companies 
- The bigger the dollar signs, the more skeptical people are 
- Past corporate failures (Foxconn, GM, DTE) prime community distrust 
- Even data center proponents regret the NDAs 
- Media narratives turn local grievances into national movements 
- Residents fear getting left with the bag if the bubble pops

The AI buildout is showing up in an environment of extreme distrust, and it slots perfectly into existing worries about risky tech bubbles & dark money in politics. Rationally speaking, I often agreed with the proponents; emotionally, I empathized with the opposition more.

It was also just very fun (WI is esp lovely) and I highly recommend similar field trips to SF friends

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Claude + @runwayml = 🔥

Lenny Rachitsky (@lennysan) — Mon, 03 Aug 2026 21:32:33 GMT

Claude + @runwayml = 🔥

Your browser does not support the video tag.

Lenny Rachitsky@lennysan

If you thought your Lenny's Newsletter subscription couldn’t get any better, you ain’t seen nothing yet.

Today, I’m adding 11 more incredible products to Lenny’s Product Pass:
1. @RunwayML
2. @WakingUp
3. @Higgsfield
4. @BrainFMapp
5. @Mercury (Personal)
6. @Resend
7. @CustomerIO 
8. @Pangram
9. @Readwise
10. @Jamdotdev 
11. @Supercut_video 

Get all of these products free for an entire year with your Lenny's Newsletter subscription*.

This brings the Product Pass to 34 (!!!) beloved, premium products—including a full year free of @Cursor_ai, @ElevenLabs, @WisprFlow, @Replit, @Lovable, @FactoryAI, @Linear, and more. 

This is over $40,000 in value for Insiders ($400/year), and over $36,000 for Annual subscribers ($200/year). 

You might think this is too good to be true, but it's not.

If you are already an Annual or Insider subscriber, grab your codes here: lennysproductpass.com

If you are currently free or monthly, upgrade to unlock the Product Pass immediately: lennysnewsletter.com/subscribe

Read the full announcement here: lennysnewsletter.com/p/productpass-…

* Some products are available exclusively for Insider-tier subscribers, including Runway, Higgsfield, Mercury Personal, Pangram, Replit, Cursor, ElevenLabs, and Lovable.

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.@tdrobbo: "It's often optimal to not have a product manager."

Lenny Rachitsky (@lennysan) — Mon, 03 Aug 2026 20:23:05 GMT

.@tdrobbo: "It's often optimal to not have a product manager."

Your browser does not support the video tag.

Lenny Rachitsky@lennysan

The CPO who regrets that product management exists

Tom Verrilli (@tdrobbo) is Chief Product Officer at @Whatnot and a long-time product leader at @Twitch and @Twitter.

We discuss:
🔸 How AI is exposing rampant “product theater”
🔸 The PM skill trending up fastest (hint: systems thinking)
🔸 Why AI’s biggest unlock for PMs is now in data science, not prototyping
🔸 Why you need to stop promoting your A-players out of the work they’re great at
🔸 Why “hire great people and get out of their way” is wrong

Full episode for your enjoyment 👇

Your browser does not support the video tag.

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New favorite, wowzers @runwayml

Lenny Rachitsky (@lennysan) — Mon, 03 Aug 2026 17:37:32 GMT

New favorite, wowzers @runwayml

Your browser does not support the video tag.

Lenny Rachitsky@lennysan

If you thought your Lenny's Newsletter subscription couldn’t get any better, you ain’t seen nothing yet.

Today, I’m adding 11 more incredible products to Lenny’s Product Pass:
1. @RunwayML
2. @WakingUp
3. @Higgsfield
4. @BrainFMapp
5. @Mercury (Personal)
6. @Resend
7. @CustomerIO 
8. @Pangram
9. @Readwise
10. @Jamdotdev 
11. @Supercut_video 

Get all of these products free for an entire year with your Lenny's Newsletter subscription*.

This brings the Product Pass to 34 (!!!) beloved, premium products—including a full year free of @Cursor_ai, @ElevenLabs, @WisprFlow, @Replit, @Lovable, @FactoryAI, @Linear, and more. 

This is over $40,000 in value for Insiders ($400/year), and over $36,000 for Annual subscribers ($200/year). 

You might think this is too good to be true, but it's not.

If you are already an Annual or Insider subscriber, grab your codes here: lennysproductpass.com

If you are currently free or monthly, upgrade to unlock the Product Pass immediately: lennysnewsletter.com/subscribe

Read the full announcement here: lennysnewsletter.com/p/productpass-…

* Some products are available exclusively for Insider-tier subscribers, including Runway, Higgsfield, Mercury Personal, Pangram, Replit, Cursor, ElevenLabs, and Lovable.

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Becoming a VP, making big decisions all day, sounds like the dream to most people. Until you actuall...

Lenny Rachitsky (@lennysan) — Mon, 03 Aug 2026 17:27:55 GMT

Becoming a VP, making big decisions all day, sounds like the dream to most people. Until you actually get there.

@tdrobbo (CPO of @Whatnot) on why so many VPs of product are becoming IC again.

Your browser does not support the video tag.

Lenny Rachitsky@lennysan

The CPO who regrets that product management exists

Tom Verrilli (@tdrobbo) is Chief Product Officer at @Whatnot and a long-time product leader at @Twitch and @Twitter.

We discuss:
🔸 How AI is exposing rampant “product theater”
🔸 The PM skill trending up fastest (hint: systems thinking)
🔸 Why AI’s biggest unlock for PMs is now in data science, not prototyping
🔸 Why you need to stop promoting your A-players out of the work they’re great at
🔸 Why “hire great people and get out of their way” is wrong

Full episode for your enjoyment 👇

Your browser does not support the video tag.

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My biggest takeaways from @tdrobbo (CPO at @Whatnot): 1. AI’s biggest unlock for PMs now is in data...

Lenny Rachitsky (@lennysan) — Mon, 03 Aug 2026 16:21:23 GMT

My biggest takeaways from @tdrobbo (CPO at @Whatnot):

AI’s biggest unlock for PMs now is in data science (not prototyping). Cohort retention pulls, analyzing user logs, and sensitivity and regression models on a @_hex_tech thread—work that took an Amazon L7 data scientist a week or two in 2017 can be done in minutes. Tom spends 10x more time in data than at any point in his career and less time talking to data scientists than ever.

Tom “regrets that product management exists,” but this isn't an insult to PMs. Tom argues that PM is a trade, not a qualification—a muscle built by reps. Hiring too many PMs as a default takes reps away from engineers and designers, infantilizing people perfectly capable of good decisions who never had to make them because “there was always a PM to babysit them.”

AI is exposing rampant “product theater.” Stakeholder management, alignment, storytelling—real work, but not product work, and they’re what the industry has rewarded PMs for the past five years. But theater only survives where real work is expensive to verify, and it isn't anymore. Every Whatnot hire is given a problem and a dataset and defends a POV out loud — and you watch how quickly the thinking decays in people who can present but can't think clearly.

The PM skill trending up fastest: systems thinking. Tom asks this question in every product review: “What do we do if the experiment is green? What do we do if it’s red?” If the answer is “I don’t know,” you haven't done the mental work necessary to run this experiment.

Stop promoting your A-players out of the work they’re great at. The common trap: take an A-player PM, make them a director, tell them to stop being hands-on, watch their instincts atrophy while junior PMs yo-yo the same PRD through review. At Whatnot, the four or five PM managers each spend at least 90% of their time on IC work; Tom spends about half his time as CPO as an IC. 

“It’s really complex” is usually code for weak leadership. Twitter ran working groups on lifting the 140-character limit for Tom’s entire tenure. Everyone knew it was inevitable—Japanese users tweeted six times as often because kanji packs more meaning per character—but nobody would make the call. It shipped almost two years after he left, and nothing bad happened. When something seems complicated, ask whether it’s actually complicated or whether leadership just won’t decide.

Map PMs to problems, not teams. Every six months, Tom, the CEO, and senior leads define the company strategy and key pillars, then assign DRIs by skill set. Some engineering teams go a year without a PM. The result: a PM who’s worked on buyer, seller, and trust problems instead of spending three years on notifications. More reps, more muscle groups.

Averages mean nothing to the individual. This is the thread running through Tom’s worst decisions. A feature only 3% of users touch looks like a deprecation candidate—until you go a layer deeper and find that for some users it’s 100% of their use case, and killing it is like “a Westfield mall turning off the power in the lead-up to Christmas.” Always ask what distribution hides under the average, and when the anecdote conflicts with the data, trust the anecdote.

True PMF is something you feel before you see it in the data. Twitter had nine heads of product in the two years Tom was there and survived anyway, because the product had a level of PMF that absorbed extraordinary mismanagement. Elon changed the name, brand, team, and culture; the network effects held. The career lesson: work somewhere with true PMF early so you learn what bottled lightning actually feels like.

End turf wars by giving one person both sides of the tradeoff. At Twitch, discovery and ads were perpetually at war for impressions. One of Tom’s first moves was to put ads inside discovery under a single PM accountable for total GMV from the feed, organic and paid alike. The tradeoff gets made naturally, cutting months of back-and-forth and the politics that turn decisions from company-first to career-first.

Lenny Rachitsky@lennysan

The CPO who regrets that product management exists

Tom Verrilli (@tdrobbo) is Chief Product Officer at @Whatnot and a long-time product leader at @Twitch and @Twitter.

We discuss:
🔸 How AI is exposing rampant “product theater”
🔸 The PM skill trending up fastest (hint: systems thinking)
🔸 Why AI’s biggest unlock for PMs is now in data science, not prototyping
🔸 Why you need to stop promoting your A-players out of the work they’re great at
🔸 Why “hire great people and get out of their way” is wrong

Full episode for your enjoyment 👇

Your browser does not support the video tag.

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Wow @HyperFrames_

Lenny Rachitsky (@lennysan) — Mon, 03 Aug 2026 14:42:30 GMT

Wow @HyperFrames_

Jake Moran@JakeFromHeyGen

Fable + HyperFrames cooked on this launch video for @lennysan’s product pass

I love the posthog animation

Your browser does not support the video tag.

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Thank you to our wonderful sponsors @WorkOS and @Mercury for supporting the podcast: 🏆 @WorkOS — Ma...

Lenny Rachitsky (@lennysan) — Sun, 02 Aug 2026 18:56:15 GMT

Thank you to our wonderful sponsors @WorkOS and @Mercury for supporting the podcast:
🏆 @WorkOS — Make your app Enterprise Ready, with SSO, SCIM, RBAC, and more:workos.com/lennyH
🏆 @Mercury — Radically different banking, now with Commandmercury.comwR

Also available on:
• Spotifyopen.spotify.com/episode/5aZUPB…Eu
• Applepodcasts.apple.com/us/podcast/thi…jS

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The CPO who regrets that product management exists Tom Verrilli (@tdrobbo) is Chief Product Officer...

Lenny Rachitsky (@lennysan) — Sun, 02 Aug 2026 18:56:14 GMT

The CPO who regrets that product management exists

Tom Verrilli (@tdrobbo) is Chief Product Officer at @Whatnot and a long-time product leader at @Twitch and @Twitter.

We discuss:
🔸 How AI is exposing rampant “product theater”
🔸 The PM skill trending up fastest (hint: systems thinking)
🔸 Why AI’s biggest unlock for PMs is now in data science, not prototyping
🔸 Why you need to stop promoting your A-players out of the work they’re great at
🔸 Why “hire great people and get out of their way” is wrong

Full episode for your enjoyment 👇

Your browser does not support the video tag.

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👇

Lenny Rachitsky (@lennysan) — Sun, 02 Aug 2026 02:26:18 GMT

👇

Dhruv Vasishtha@dvasishtha

Every founder I know wants forward deployed AI PMs and it seems the best profile is a mythical CS undergrad who spent two years at McKinsey then two years in product / biz ops at a series A startup.

The reality is you're going to have to be intentional in training up this talent.

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Excited to announce that @MatthewDicks will be teaching a hands-on workshop on storytelling at the L...

Lenny Rachitsky (@lennysan) — Sat, 01 Aug 2026 22:51:40 GMT

Excited to announce that @MatthewDicks will be teaching a hands-on workshop on storytelling at the Lenny & Friends Summit.

Matthew is a columnist, playwright, school teacher, and...60-time Moth StorySLAM champion, 9-time GrandSLAM champion, and internationally bestselling author of 9 books, including Storyworthy, my all-time favorite book on the skill of storytelling.

This is going to be something special.

See you there!

P.S. Here's my podcast episode with Matthew: youtube.com/watch?v=J4wguy…

Lenny Rachitsky@lennysan

Excited to announce that the man the myth the legend @karrisaarinen will be speaking at Lenny & Friends Summit

See full lineup here: https://t.co/WNxqQRyGYC

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Niiiiiiiiiiiiiice @HyperFrames_

Lenny Rachitsky (@lennysan) — Sat, 01 Aug 2026 20:08:16 GMT

Niiiiiiiiiiiiiice @HyperFrames_

Bin Liu@liu8in

been getting so much value from Lenny, can finally contribute back a tiny bit

here’s a launch video for you made with Opus 5 & @HyperFrames_ (w/ our internal agent harness)

have a few more options for you if you are interested! @lennysan

Your browser does not support the video tag.