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Best of Lenny’s Newsletter 2026

2026-01-06 21:45:22

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P.S. Insider subscribers get a free year of 19 premium products: Lovable, Replit, Gamma, n8n, Bolt, Devin, Wispr Flow, Descript, Linear, PostHog, Superhuman, Granola, Warp, Perplexity, Raycast, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas (terms apply). Subscribe now.

Anthropic co-founder Ben Mann’s words continue to ring in my ears: “This is as normal as it’s going to be. It’s going to be much weirder very soon.”

In the swirl of so much change, there’s a growing divide between the people who understand where things are going and are benefiting from it, and those who don’t and will have an increasingly hard time. More and more, I see my mission as making sure you’re in the first group.

Through deeply researched essays, in-depth interviews with world-class operators working at the bleeding edge, a thriving online and offline community, free access to the latest and greatest AI tools, and the surprisingly helpful Lennybot (trained on all of the newsletter and podcast content, it’s very good!), your subscription gives you a giant leg-up on the fast-approaching weird future.

To help you get ready for the sure-to-be-absurd year ahead, below are the 25 best and most popular posts from the past year, plus a few all-time classics. I know I put out a lot of content, so if you’ve still got 50 tabs open with posts you’ve been planning to read, close them all and check out the stuff below.

As always, I’d love your frank and honest feedback on what you love and what I could do better in the coming year. You can always find me at [email protected].

Finally, to keep myself accountable, here’s a quick look back at my goals for 2025:

Launching a new newsletter or podcast vertical ✅ — How I AI has been a huge hit (go Claire!), and I’m in the process of exploring the next addition.
Lenny and Friends Summit 2.0 🟡 — Stay tuned for some news on this 👀
Making the paid subscription an absolute no-brainer by adding more killer perks ✅ — The Product Pass has been a wild success, and wait till you see what we’ve got coming this year.
Launching a product ❌ — I decided it wasn’t the right year for this.
Above all else, continuing to deliver a high-quality newsletter and podcast every week ✅ — I think we achieved this, though I can always do better.

Now here are my goals for 2026:

Keep increasing the quality and value of the newsletter (possibly cutting back the quantity a bit)
Invest more into supporting the community around the newsletter and podcast
Launch an additional newsletter or podcast vertical
Lenny and Friends Summit 2.0 👀👀👀
Carefully balance content cadence between AI and non-AI, IC vs. manager vs. VPs, and product management vs. adjacent skills

Here we go.

📣 Quick heads-up: We’re refreshing our Product Pass partner lineup at the end of January

We’ve got some very exciting new products coming to the Product Pass in a few weeks, and to make room, a few current partners are rolling off the bundle: codes for Descript, Raycast, and Superhuman will expire on January 29th.

If you’ve been meaning to try any of these amazing products, this is your chance.

Head to LennysProductPass.com to grab your codes, and activate them by following the redemption instructions by January 29th. (Note: Descript is Insider-only, so if you’re at the Annual tier it’ll only be there if you grabbed it already.)

While you’re there, check out the other products too. Supplies are limited and deals do expire, so don’t miss out on the tools that you want to try out.

And now, the top posts from the last year . . .

Best on AI

An AI glossary—The most common AI terms explained, simply
Everyone should be using Claude Code more—How to get started with Claude Code, and 50 ways non-technical people are using it in their work and life
What people are vibe coding—Real-life examples of what non-technical people are building to inspire your own vibe-coding journey
25 proven tactics to accelerate AI adoption at your company—Practical advice from AI-forward companies like Shopify, Ramp, Zapier, Duolingo, Intercom, and Whoop
A guide to AI prototyping for product managers—How to turn your idea into a working prototype in minutes
Make product management fun again with AI agents—A guide to building AI agents

Best on career

Product manager is an unfair role. So work unfairly.—How to thrive in “the great flattening” by redefining work norms
State of the product job market in 2025—There’s a lot to be optimistic about
The definitive guide to mastering the analytical and product sense interviews—A step-by-step playbook to help you ace your PM interviews
The ultimate guide to negotiating your comp—The step-by-step guide that’s helped hundreds of leaders secure life-changing compensation
The Magic Loop—A framework for rapid career growth

Best on health

Why you’re so angry at work (and what to do about it)—A practical framework for transforming big feelings into wisdom
Why no productivity hack will solve your overwhelm—How the Internal Family Systems model can help you listen to your inner wisdom and get unstuck
How tech’s most resilient workers handle burnout—Introducing ARMOR: a new framework building on our tech worker sentiment survey insights
A builder’s guide to living a long and healthy life, with Justin Mares—For something a little different

Best on strategy

This week on How I AI: Zapier's CEO shares his personal AI stack

2026-01-06 00:03:32

Every Monday, host Claire Vo shares a 30- to 45-minute episode with a new guest demoing a specific, practical, and impactful way they’ve learned to use AI in their work or life. No pontificating—just practical and actionable advice.

Zapier’s CEO shares his personal AI stack

Brought to you by Brex—The intelligent finance platform built for founders

In this episode, Wade Foster (co-founder & CEO of Zapier) shares the actual way he’s leading real AI adoption inside Zapier—by using it hands-on himself to understand company culture, evaluate candidates, and find talent most recruiters never see. We get concrete workflows Wade uses everyday: building interview-evaluation agents, using tools like Grok to surface diamonds-in-the-rough candidates, and analyzing meeting transcripts to uncover Zapier’s “unspoken culture.” He also explains why AI fluency can’t be delegated, how leaders should create safe “play spaces” for experimentation, and why the definition of “top talent” is rapidly changing.

Biggest takeaways:

CEOs must do more than write an “AI memo.” Wade sees many executives fall into the “delegation trap”—writing a memo about AI adoption then expecting it to filter down through the organization. Instead, leaders should create “play spaces” like hackathons and show-and-tells where teams can experiment with AI tools without pressure.
You can build an interview evaluation agent in minutes. Wade demonstrated a simple Zapier agent that analyzes interview transcripts against job descriptions and company values, then recommends whether to advance candidates. This provides an unbiased second opinion that helps catch things human interviewers might miss.
Use Grok to find “diamonds in the rough” talent. While most recruiters focus on LinkedIn, Wade uses Grok to search X/Twitter and YouTube for potential candidates who match specific criteria. This surfaces people who might never appear in traditional recruiting channels—especially in communities that are active on these platforms.
Extract your “unspoken culture” from meeting data. Wade uses Granola’s meeting transcripts with a simple prompt to generate a document that reveals how the company actually operates—not just what’s in the official values doc. This uncovers specific behaviors and expectations that even the CEO hadn’t articulated, creating a powerful tool for hiring, onboarding, and performance management.
Top talent is still in demand everywhere. Despite AI transformation, Wade says Zapier remains “insatiable” for engineering talent and continues hiring across all functions. The difference is that “what it means to be top has changed”—the best people now leverage AI to multiply their impact.
Make AI fluency expectations explicit. Zapier has created rubrics that clearly define AI fluency expectations for different roles. This gives employees specific skills to develop rather than vague directives to “use more AI.”
AI adoption requires hands-on experience. When people actually use AI tools, “some of the fear goes away.” Users quickly discover both the capabilities and limitations, developing a more pragmatic view than the “boogeyman in the closet” portrayed in media narratives.
Use AI to test your stated values against reality. By analyzing how people actually communicate and operate, AI can reveal whether a company’s lived culture aligns with its stated values—giving leaders powerful insights for course correction.

▶️ Listen now on YouTube | Spotify | Apple Podcasts

If you’re enjoying these episodes, reply and let me know what you’d love to learn more about — AI workflows, hiring, growth, product strategy, anything.

Catch you next week,
— Lenny

P.S. Want every new episode delivered the moment it drops? Hit “Follow” on your favorite podcast app.

Zapier’s CEO shares his personal AI stack | Wade Foster

2026-01-05 20:03:50

Wade Foster is the co-founder and CEO of Zapier. In this episode, Wade shows how he uses meeting transcripts, Zapier agents, and even Grok to analyze company culture, evaluate interview candidates, and source talent from unexpected places. He explains why CEOs need to lead by example when it comes to AI adoption and shares practical workflows that any executive can implement to make hiring more effective and efficient.

Listen or watch on YouTube, Spotify, or Apple Podcasts

What you’ll learn:

How to use meeting transcripts to extract your company’s “unspoken culture” and compare it against your stated values
A workflow for creating AI interview evaluators that assess candidates against your job descriptions and company values
How to use Zapier agents to provide objective feedback on candidate interviews while checking your own biases
Why CEOs should participate in AI “hackathons” and “show and tells” rather than just delegating AI adoption
A surprising technique for using Grok to find “diamonds in the rough” talent outside traditional recruiting channels
How AI enables companies to complete tasks that were previously not economically viable

This entire episode is brought to you by:

Brex—The intelligent finance platform built for founders

In this episode, we cover:

(00:00) Introduction to Wade Foster

(02:32) Zapier’s AI adoption

(06:50) Creating AI fluency rubrics

(08:37) Using Granola to extract company culture from meeting transcripts

(10:49) Practical use cases for company culture rubrics

(13:38) Building an AI interview evaluation agent in Zapier

(16:50) Using Copilot to improve agent prompts

(18:49) Ideas for enhancing the interview agent

(22:31) Mistakes people make when using agents

(25:11) Using Grok to find talent on social media platforms

(33:39) Recap of AI workflows for recruiting and hiring

(34:40) Lightning round and final thoughts

Tools referenced:

• Zapier: https://zapier.com/

• Zapier Agents: https://zapier.com/agents

• Granola: https://granola.ai/

• Grok: https://grok.x.ai/

• ChatGPT: https://chat.openai.com/

• Copilot: https://copilot.microsoft.com/

Other references:

• Zapier values: https://zapier.com/about

• How Zapier’s EA built an army of AI interns to automate meeting prep, strengthen team culture, and scale internal alignment | Cortney Hickey: https://www.lennysnewsletter.com/p/how-zapiers-ea-built-an-army-of-ai

• How this CEO turned 25,000 hours of sales calls into a self-learning go-to-market engine | Matt Britton (Suzy): https://www.lennysnewsletter.com/p/how-this-ceo-turned-25000-hours-of

Where to find Wade Foster:

Zapier: https://zapier.com/

LinkedIn: https://www.linkedin.com/in/wadefoster/

X: https://twitter.com/wadefoster

Where to find Claire Vo:

ChatPRD: https://www.chatprd.ai/

Website: https://clairevo.com/

LinkedIn: https://www.linkedin.com/in/clairevo/

X: https://x.com/clairevo

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale

2026-01-04 21:31:22

Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth.

Listen on YouTube, Spotify, and Apple Podcasts

We discuss:

“Give away your Legos”: a framework for scaling yourself as a leader
“J-curves vs. stairs”: the two paths of career growth, and why you should pick the scarier path
“The waterline model” for diagnosing team problems (and why you should “snorkel before you scuba”)
Six rules for creating effective goals (and aligning everyone around them)
Rules of thumb for leading through rapid scale and change
Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor

Brought to you by:

DX—The developer intelligence platform designed by leading researchers

Brex—The banking solution for startups

GoFundMe Giving Funds—Make helping a habit

Where to find Molly Graham:

• X: https://x.com/molly_g

• LinkedIn: https://www.linkedin.com/in/mograham

• Substack: https://mollyg.substack.com

• Website: https://glueclub.com

Referenced:

• Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora

• Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652

• Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage

• Quip: https://quip.com

• He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor

• Chan Zuckerberg Initiative: https://chanzuckerberg.com

• 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths

• ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups

• The Muppets: https://muppets.disney.com

• Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell

• J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve

• Forget the corporate ladder—winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks

• Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath

• Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921

• Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you

• Zevi Arnovitz on LinkedIn: https://www.linkedin.com/in/zev-arnovitz

• Peopling 101: The Waterline Model: https://christinehaskell.com/blog/peopling-101-the-waterline-model

• Introduction to NVC: https://www.cnvc.org/learn/what-is-nvc

• I hate OKRs... and other thoughts about goal setting: https://mollyg.substack.com/p/i-hate-okrs-and-other-thoughts-about

• Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics

• James Clear’s quote: https://www.goodreads.com/quotes/9614600-problem-1-winners-and-losers-have-the-same-goals

• Founder mode: https://paulgraham.com/foundermode.html

• Stripe: https://stripe.com

• Patrick Collison on X: https://www.linkedin.com/in/patrickcollison

• John Collison on X: https://x.com/collision

• Seth Godin’s best tactics for building remarkable products, strategies, brands and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products

• Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow

Recommended books:

• The Artist’s Way: https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252

• Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212

• Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr)

2026-01-01 21:31:28

Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed.

Listen on YouTube, Spotify, and Apple Podcasts