2026-08-11 21:31:07
👋 Hey there, I’m Lenny. Each week, I share deeply researched product, growth, and career advice. For more: Lenny’s Podcast | Lennybot | How I AI | Become an AI-Native Builder and other favorite AI/PM courses
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Kristen does such an incredible job of introducing this piece that I’ll just skip my regular intro and jump right into it.
Kristen Lowe is an executive ghostwriter and narrative strategist, and the incoming Director of Founder & Editorial Communications at Scribe. Previously the Director of Operations at Hinge, she has built founder communication platforms across LinkedIn, Substack, X, and keynote stages, and written for leaders in every format from essays to TED Talks. You can find more of her work on AI, careers, and storytelling on Substack and TikTok.
It’s never been easier to start a company. It’s also never been harder to get someone to care that you did. Anyone can now go from idea to business in less time than it takes to hire a single engineer. But the same tools that make building simple make standing out a challenge.
As channels like X and LinkedIn flood with soulless AI slop, startups are having to work harder to grab people’s already fractured attention amid all the noise. But this moment presents an opportunity for founders who can say something honest and connective by “going direct”—or what I call founder-led communication. Today, a solid founder-led communications strategy is one of the lowest-cost, highest-leverage tools at your disposal to get people’s attention.
Most founders seem to know this. When I started writing for founders as an executive ghostwriter and comms strategist, the biggest surprise was the constant stream of inbound clients at all stages who thought they “should” be building a public platform but didn’t know how to start. I’d assumed people would want ghostwriting help because they just hated writing, but the number one reason founders reached out for help was “I have no idea what to say.”
There’s a discouraging misconception that for comms to be impactful, you have to be vulnerable, contrarian, or profoundly entertaining in every message you put out there. I hear from founders all the time who are daunted by that expectation. But in my experience, the only thing most people need to build a credible comms strategy is an answer to the question “Why did I start this company?”
This answer is usually the most narratively powerful idea to share about your business. Starting a company is a life-altering pursuit with a famously high failure rate. Whatever reason sent you down that path, it was once compelling enough to rearrange your whole life around and recruit others to do the same. Founder communications work because people care about and root for other humans, not entities or widgets.
More importantly, if you’re not excited about the story of why you started this company, you should probably look for a different line of work. As more people stray from traditional career ladders and as entrepreneurship becomes more popular, there will be a wave of founders who start companies simply because they can, or because it looks like a fast track to a lot of money. People can tell when you’re in it for the wrong reasons—which includes no reason at all. There’s no comms strategy for that. But for everyone else: if your reason was convincing enough for you, it’s convincing enough to make other people care too.
Once you know your “why,” this guide will help you figure out the right strategic communications choices for your business, so all you have to do is start writing and hit post.
While every founder’s “why” is unique, they almost always fall into one of three categories, each mapping to a founder archetype that can help you define your comms strategy:
The “Problem” founder: The person who started a company to solve their own problem
The “Insight” founder: The person who started a company to solve a problem only they saw
The “Vision” founder: The person who started a company because they imagined a better world
Lumping yourself into an archetype might seem like a counterintuitive way to build distinctive founder content, but the ways people connect with founders map to these three relationships: I identify with you, I trust you, I’d follow you. A unique story makes your content interesting, but your archetype determines which feeling it evokes in your audience, and cultivating the right one for your business requires different strategic choices.
Your founder archetype will guide you to the decisions that matter for a comms strategy:
Goal: What specifically your content strategy is meant to achieve
Voice: How you should sound
Messaging pillars: What you should talk about
Success conditions: How you’ll know if it’s working
What your founder archetype will not tell you are answers to questions like “How often should I post?” Founder comms are like workout routines: the best one is the one you can commit to. Regardless of your archetype, committing to any channel and cadence that works for you beats agonizing over the perfect one. And everything else you might be worried about—audience segmentation, attribution, earned vs. organic media balance—is secondary. You can tackle that once you have a substantial body of content to optimize around.
The Problem founder is someone who started their business to solve a problem that was personally tormenting them. Think Sara Blakely, who hated how pantyhose looked under her pants, so she cut the feet off them and founded Spanx, or Tobi Lütke, who tried to sell snowboards and got so frustrated with the existing e-commerce programs that he decided it would be easier to build Shopify instead.
What makes these founders compelling is that they understand the customer better than anyone else could, because they are the customer. When you’re solving a problem because it caused you so much pain that you restructured your life around fixing it, you have a unique power to make your customer feel seen and understood. You get to say that you’re working for “us,” not for “them,” and your success becomes “our success.” That narrative is a powerful tool for building affiliation and brand loyalty. The Problem founder has a singular ability to identify as a customer first and business owner second, which should anchor their entire comms strategy.
You’re a Problem founder if: you started your business to fix a problem you were personally experiencing, when you realized the only way to get it solved was to do it yourself.
Goal: Build a loyal following of customers who feel deeply understood and recognized by your product.
Ideal voice: Personal, honest, detailed, (appropriately) urgent/frustrated
Primary messaging pillar: The centerpiece of a Problem founder’s comms strategy is high-repetition, vignette-style storytelling about their experience with the problem. I think of this as the Taylor Swift method: communicate specific, scene-based details about an experience to evoke universal and strong emotional responses. You should have a well-rehearsed “origin story” that describes your experience with the problem and can be repeated across channels. For that story to connect, it can’t sound like “existing options weren’t working for me.” It needs to be more like “I was crying in my car during lunch.”
Additional pillars:
Product design. The Problem founder has one of the best excuses to talk about the product in granular detail because every feature likely has a personal origin story. Beyond telling the founding story, you should share the experience of building the product, the choices you made, what personal experiences led you to make them, and which features you love the most and why.
Community experience. The Problem founder can also engage and highlight early and devoted supporters of the company by recapping interactions with customers or directly sharing their stories. Share what it meant to you to hear from other people who needed your product. Use their words to explain why your product exists.
Founders who have done this well:
Sara Blakely (Spanx): Her LinkedIn posts are the template for talking about the problem, even after decades of doing so. If you want to hear what a detailed origin story sounds like in full, listen to her Masters of Scale episode.
Dave Gilboa (Warby Parker): His Good Life Project podcast episode and Daily Californian interview are excellent examples of how to tell the same story across mediums.
Will Ahmed (Whoop): His How I Built This episode sounds well-rehearsed but not canned. Check out his original Whoop “Locker Blog” posts and this tweet for short, effective examples of the written version of this storytelling mode.
Tope Awotona (Calendly): His How I Built This episode stands out because he also talks about companies he started just to make money. Listen to the contrast to understand why the personal narrative plays so well.
Common mistakes:
Overgeneralizing. A Problem founder who wants to decenter their story or who worries their experience is too niche often ends up talking about vague descriptions of the problem that anybody could share. Stay in the details. Remember, you are Taylor Swift, not a corporate sales team.
Slipping into CEO persona. A Problem founder who is busy thinking about the mechanics of their business can end up accidentally talking in the language of market gaps and competitor shortcomings instead of their actual experience. That slip pulls you away from the part of your identity that matters to your customer: your shared challenge or frustration.
Oversharing beyond your story. It’s easy to think that because people care about your founding story, they want to hear about your whole life, but a Problem founder who gets sucked into acting like an influencer can quickly dilute their message. You don’t need to reveal tons of information about your personal life. It sacrifices your privacy without bringing anyone closer to the business.
Best channels: Problem founders play well with organic storytelling opportunities and community-forward environments: social media, podcasts (think: How I Built This or The Diary of a CEO), and profile pieces. Go where your community already is, pick a short-form video platform you can commit to (if you’re willing), and try to get a conversation-style speaking engagement where you can tell your story in full. Then clip and spread it across your other channels. X is not usually your best storytelling channel, and panels won’t always give you space to tell your story. That doesn’t mean you should say no to them on principle, but your time is limited, so try to spend it where you can tell the full story and then syndicate.
How you’ll know it’s working: Customers will start telling you about their experiences in your comments, replies, and inbox instead of just writing “great post!” Followers will share and amplify your content.
Prompts to get you started:
What was the very worst day I ever had with this problem? (Be vivid!)
What was the tipping point when I decided I had to fix this myself?
When did I realize that it wasn’t just me dealing with this?
Once I figured out how I wanted to fix this for myself, why did I feel like I had to fix it for other people too?
The Insight founder is someone who started their business because they saw or understood something before others did and decided to change it. Insight founders are intriguing because the inciting incidents in their stories usually take the same shape, but the motivations vary widely. Some Insight founders see a better way to do something and recognize the gap as a financial opportunity; others see a suboptimal system and are just so annoyed by the inefficiency that they have to fix it themselves.
Classic examples of Insight founders include Stewart Butterfield, who built Slack because he noticed that the workplace was running on informal communication without a specific product to support it, and Reed Hastings, who recognized that the most profitable part of the video rental business, late fees, was also the part customers hated most.
What makes Insight founders compelling is that they were right—early. Where Problem founders build customer loyalty by making people feel understood, Insight founders do almost the reverse. They make people feel smarter by helping them consider new perspectives, understand complex subjects, and form opinions that they otherwise wouldn’t have come up with. That relationship with customers is a slow build, but it’s a durable one. An audience that believes you understand things others don’t and trusts your read on an industry will borrow your language, repeat your conclusions, and eventually accept your opinions as a reason to believe in your company. Most founders you think of as “thought leaders” are Insight founders, and they’re uniquely positioned to share and debate their points of view.
You’re an Insight founder if: you spotted an incorrect assumption, a broken process, or a mispriced problem—and once you saw it, you dove in to correct it.
Goal: Build a following of people who trust your opinions and analysis enough to adopt your ideas and believe in your company.
Ideal voice: Clear, analytical but accessible, curious, opinionated, generous
Primary messaging pillar: The core communication pillar for an Insight founder is regular, incisive thought leadership about their industry. It’s easy to believe an Insight founder builds credibility by being right all the time, but the more important thing is being helpful. You can lend credence to your original insight by generously helping people understand other subjects with clear, explicit reasoning. The insight you’ll explain the most should still be the one that sparked your business. Speak about it frequently but not exclusively, so you don’t get branded as someone who was only right about one thing one time.
Additional pillars:
Predictions. The natural extension of sharing opinions about industry changes and events is predicting what happens next. Especially in high-ambiguity moments (like the current AI boom), the Insight founder is uniquely positioned to make a prediction early. If you’re right, it’s a major boost to your credibility, but too many wrong calls will catch up with you, even if you can explain what you misread. Only make predictions that you feel confident about your reasoning for.
Engaging with other thinkers. An Insight founder who only puts out their own takes can come across as interested only in their own thoughts. Interacting with other thought leaders will strengthen your thinking. Debate, share what inspires you, and comment on other people’s posts. This content is easy to produce and shows people you’re learning as much as you’re speaking.
Founders who have done this well:
Aaron Levie (Box): Aaron is the person I think about when I think about founders who do X well. He posts original insights, engages with others, and gets basically every part of this right.
Patrick Collison (Stripe): His Atlantic byline and personal website both illustrate how you can generate thought leadership without just talking about your company.
Jason Fried (37signals): His “Why work doesn’t happen at work” TED Talk is a brilliant example of explaining without patronizing. Also check out his posts on X and his Signal v. Noise essay for effective written examples.
Des Traynor (Intercom): The Intercom Blog is a strong model for company-hosted thought leadership, especially if social channels intimidate you.
Rahul Vohra (Superhuman): This First Round Review byline is a standout example of letting people into your reasoning. Awesome long-form.
Common mistakes:
Making people feel stupid. The Insight founder fails most consequentially when their reasoning is unintelligible to their audience or when they make people feel stupid for not seeing what they do. Watch out for being contemptuous or disrespectful to your audience or industry incumbents. Explain why people couldn’t see what you did (what you had access to that they didn’t or why the inertia was strong), not how dumb they were for missing it. Remember, your superpower is that you make people feel smarter. Do so carefully and generously.
Publishing “takes” without reasoning. An Insight founder who is all hot takes without reasoning can build a high-engagement platform and mistake it for a high-loyalty one. Remember that it’s your thinking that people care about and want to learn from. Don’t just shoot out daily hot takes without helping other people understand how to get to those conclusions. It reads as loud, and it makes being wrong more punishing.
Never admitting uncertainty. The Insight founder should be confident enough for others to believe in their reasoning while also admitting when they’re not. You are allowed (encouraged, even) to publish takes about your uncertainty. Especially once you have a larger platform, people find it relieving to hear someone they trust say, “I’m not sure either, but here’s what I make of this so far.”
Best channels:
Go long-form whenever you can: Essays, newsletters, podcasts, and long panels. Best-case scenario, you eventually publish a book if you have a consistent enough thesis. Insight founders need space to explain the nuances of their thinking, so while you should stay present on engagement-heavy platforms like X and LinkedIn, you almost always benefit from some form of regular, long-form content.
My hottest take might be that you shouldn’t use LinkedIn as your platform for that content. LinkedIn rewards conclusion-forward takes, and it’s an AI bloodbath right now, so if you’re going to use it, at least use the newsletter feature instead of normal posts. Short-form video should distribute your long-form thinking, but it’s not a substitute for it.
How you’ll know it’s working: You’ll see your language getting recycled by other people, your reasoning will show up in other people’s arguments, and you will start receiving outreach and invitations to share your thoughts in new formats.
Prompts to get you started:
What about my life experience, background, and perspective made the idea that launched my startup clear when it wasn’t clear to others?
Why was my industry doing things the way it was?
What are three things about my industry that I find myself thinking about often? What’s my POV on them?
What’s something other people might struggle to make sense of in my industry that feels logical or intuitive to me?
The Vision founder is the rarest of the founder archetypes, and it is easy for Insight founders to mistake themselves for Vision founders by inflating the grandeur of their own venture. The Vision founder is someone who starts their business because they can imagine a radically different, nonexistent world that others can’t see and builds a company to get there. They’re not always solving a problem, at least not one that feels like a pain point. Steve Jobs, perhaps the most famous Vision founder of all time, didn’t think computers had to be ugly and inaccessible. Yvon Chouinard, who founded Patagonia, wasn’t willing to accept that profit and environmental stewardship were mutually exclusive and started a business to prove it.
Just as Problem founders make us feel seen and Insight founders make us feel smarter, Vision founders make us feel hopeful. We care about them and their companies because they are passionate and determined enough to try to change the world. Their recruits and investors tend to be like-minded, and their customers can feel like followers more than buyers. These founders are often charismatic and a little mysterious, but they are best positioned to make their audience feel like supporting their business is equivalent to being part of a movement.
You’re a Vision founder if: you started your business because you could picture a fundamentally different way the world could work, and a company was your way of getting people there. You are unironically trying to change the world.
Goal: Build a following of talent, customers, investors, and general supporters who are deeply invested in where you’re going and feel motivated to be a part of it.
Ideal voice: Expansive, certain, hopeful, and plainspoken
Primary messaging pillar: The Vision founder’s communication strategy is in many ways the least obvious of the three. Instead of focusing solely on the vision, it’s anchored in breaking down the assumptions that keep people attached to the status quo. The Vision founder has to disagree with a convention or belief about why the world is the way it is, and it is the disagreement—more than the vision—that makes them interesting. As a Vision founder, your primary messaging pillar is “x doesn’t have to be true,” and it should include fair and generous explanations of why the status quo logic needs revision. This requires repetition, patience, evidence, and thorough explanation, but it’s what prevents the Vision founder’s future from feeling naive and aspirational.
Additional pillars:
The vision (in detail). The Vision founder does need to talk about the future, and this pillar should show up often and across channels. To create a compelling vision, details are the game. “A better way of working” is intangible and uninspiring, but “Never being late to picking your kids up because…” is emotional and concrete. The trick is letting people visually locate themselves in your future and imagine their life in it. Like the Problem founder, you don’t have to speak to every single person; you have to capture an emotion that feels concrete and universal.
Milestones and progress. Launches, partnerships, new releases, and incremental business steps matter more for the Vision founder than the other archetypes. When you sign a partnership or launch a new feature, it’s proof that your vision is possible and you can actualize it. It’s why Vision founders do over-the-top launches and broadcast-scale product announcements. A keynote might not be in your budget, but try to find opportunities to show your progress.
Founders who have done this well:
Steve Jobs (Apple): This was an internal speech, but his “Think Different” talk for employees is one of my favorite examples of being clear on what you stand for. Skip to 6:30 to listen to him talk about Apple’s “why.” It’s fantastic.
Melanie Perkins (Canva): Her “note to the Canva Community” illustrates how to make the biggest announcement of your company’s life without making it about you. Her SXSW interview showcases that messaging in a keynote setting.
Elon Musk (Tesla): His Master Plan essays (check out Part I and II) are a perfect example of how to prevent the vision from sounding too grand or naive.
Yvon Chouinard (Patagonia): “Earth is now our only shareholder” is top-tier “x doesn’t have to be true” messaging.
Note: Vision founders are rare, good ones are rarer, and a lot of Insight founders position themselves as Vision founders but don’t actually reach that bar.
Common mistakes:
Contempt for the status quo. Like the Insight founder, the Vision founder runs the risk of making people feel foolish. Be mindful to steer your tone away from “look at this ridiculous thing you’ve all accepted,” and keep it closer to “it makes sense that you believed that, but here’s what you can believe now.”
Making yourself the protagonist. The worst type of Vision founder is someone who wants to be at the center of the world they create. Although they need to be persuasive and energizing, the Vision founder best serves their vision by staying out of it. Keep your founder-specific content rare and narrow. The goal is not to make people think you’re a genius or aspiring world leader. You want to avoid cult-leader allegations and keep people focused on what you’re trying to achieve.
Talking in scale instead of shape. An excited Vision founder loves to talk about how big the coming transformation is. So much disruption, so many lives changed, etc. But talking about the scale instead of the specifics can make the future feel daunting and less achievable. The “what” is more important than the “how big.” Don’t get lost in telling people how different things will be; just be concrete in your descriptions of what will be different.
Best channels: Vision founders do best with video and audio, and there’s just no real way around that. The conviction you’re trying to build requires persuasive firepower—tone, cadence, body language—and most of your audience isn’t going to absorb that in manifesto form. Keynotes, launch events, TED-style stages, long-form video and audio, and anything clippable are where you’ll thrive. You’re the hardest archetype to run channel strategy for, because your best formats are scarce. That doesn’t mean you should say yes to every speaking opportunity, but any time you have a credible invite to a stage or a mic, take it. You need those opportunities more than the other archetypes do.
How you’ll know it’s working: People will start describing your world back to you in their own words and start championing the vision for you.
Prompts to get you started:
What does a day in my better world actually look like? What’s the best part of it?
What are people currently accepting as normal that’s actually just a choice? Where’d they learn it?
Why do I believe this is possible when most people don’t?
What makes my idea worth believing in, even if it’s hard to get there?
2026-08-10 23:01:49
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Claire built an AI agent that reviews pull requests, scores their risk, auto-approves the safest ones, and sends anything questionable to Slack. In this episode, she breaks down how she built the entire thing in one Codex session using Vercel Eve, and why letting AI review AI-generated code may be a lot less risky than it sounds.
You don’t need a human to review every AI-generated PR. That may sound reckless, but it’s increasingly looking like the smarter operating model. Intercom has already shown this can work at scale: PRs approved by its AI system move five times as fast as human-reviewed ones and have a lower revert rate. In other words, the AI-reviewed code isn’t just shipping faster—it’s less likely to need fixing after it reaches production.
The key is having a clear way to separate changes that can skip human review from ones that can’t. The risk model used here scores each PR across six dimensions: the size of the change, its blast radius, how easily it can be reversed, its data and security implications, its operational impact, and whether tests and CI have actually been completed. Anything below 24 points is classified as low risk and cleared by the agent; anything above 64 goes straight to a human for review. The exact numbers matter less than turning a vague judgment call into a repeatable system.
Vercel’s Eve may be the fastest way to deploy a serious internal AI agent across Slack and GitHub without spending weeks building infrastructure. It handles the annoying plumbing—connectors, refresh tokens, sandboxing, and routing across channels—so the actual work becomes writing instructions and skills in Markdown instead of babysitting OAuth flows.
A useful internal agent can now be built and deployed in a single Codex session, starting with a prompt that’s only a couple of sentences long. In this case, the initial ask was essentially: build a GitHub bot that waits for checks to pass; grades each PR as low, medium, or high risk; and automatically approves the low-risk ones. Everything after that was steering and refinement, not a giant up-front specification.
Browser use removes much of the configuration tax that makes agent setup feel harder than it should. Creating a Slack bot and GitHub app manually normally means clicking through endless permission screens, choosing scopes, and managing tokens. Codex handled almost all of that through the browser. The human’s job was mostly to click “save” and complete 2FA. What usually takes hours took minutes.
SOC 2 compliance and automatically approved PRs are not inherently at odds. The important part is making the process legible: the risk model needs to be reflected in the company’s code-review and security policies, every decision needs to be logged, and the resulting audit trail needs to be easy to query and defend. The security team’s role is to help design the right framework, not simply block automation because it feels unfamiliar.
The operational design matters just as much as the underlying technology. Merge Mommy doesn’t actually merge anything. Instead, it posts a gray check in GitHub as a signal, then sends a Slack message with the risk score and a note saying the PR is ready to approve and merge. That small handoff preserves human accountability for the final action while eliminating most of the cognitive work involved in reviewing a routine change.
Evals are what keep internal agents trustworthy after the novelty wears off. Intercom logs every PR review its agent produces and then has an engineer assess whether the score and recommendation were correct. That’s the same discipline strong teams already bring to customer-facing AI products. Internal agents may feel less visible, but when they touch something as important as the codebase, they need the same protection against regressions.
The surprising thing about building an Eve agent is how little “building” is actually involved. The full instructions for Merge Mommy fit on roughly a page: a few paragraphs, a handful of bullets, and a short skill file. There isn’t much framework-specific magic to learn. The core skill is simply being able to explain, clearly and precisely, what the agent should do.
How I Built ‘Merge Mommy’: My AI Bot for Auto-Reviewing Pull Requests with Vercel Eve: https://www.chatprd.ai/how-i-ai/merge-mommy-vercel-eve-ai-bot-for-auto-reviewing-pull-requests
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Grace Clarke is an AI educator and former marketing consultant who rebuilt her entire service business around Claude. In this episode, she walks through the three Claude skills that run her business: an hourly client pipeline, a proposal builder, and a voice guide that teaches Claude how she thinks. She also shows how she replaced Gmail with her own Claude-powered inbox, why she believes intent engineering matters more than prompt engineering, and how non-technical people can start building useful AI workflows without writing code.
You don’t need to be technical to build a business workflow with Claude. You need to be clear about what’s broken. Grace started by opening Claude Code and talking for a few minutes about everything driving her crazy: too many emails, client communication that didn’t feel warm enough, and 20 hours of admin every week. Claude helped turn that into an operating system for her business.
Intent engineering matters more than prompt engineering. Grace doesn’t spend time crafting the perfect prompt. She explains the problem, describes the outcome she wants, and asks Claude to come back with a proposal. Her philosophy is simple: the burden of figuring out what to do next shouldn’t always fall on the person. Give Claude enough context, and it should be able to study how you work and bring you strong ideas to react to.
Grace’s voice guide isn’t really a writing guide. It’s closer to a “think like Grace” file. It captures how she makes decisions, what she believes about teaching versus consulting, what good communication sounds like, and even the kinds of LinkedIn posts she never wants to resemble. Whenever she sees something that makes her cringe, she sends Claude a voice note and updates the guide.
Doing all of your email inside Gmail means almost none of that work compounds. Every response contains useful context: how a client communicates, what tone works with them, what they care about, and the history of the relationship. But if that context stays buried in Gmail, the AI never gets smarter from it. Grace moved her inbox workflow into Claude so every interaction can become useful context for the next one.
Grace has developed a surprisingly elegant way to move between Claude Code and Cowork. She uses Claude Code when she wants something proactive that will go figure things out. Then, when she wants a more visual and approachable environment, she has Claude Code create a Markdown handoff file and drops it into a new Cowork session. The result is a simple way to carry context from one environment to another without starting over.
The biggest barrier to adopting AI may be less about fear and more about muscle memory. Grace used to give students carefully engineered prompts so they could experience an immediate win. Her students told her that approach was actually making things harder. What helped more was building the habit of reaching for AI in the first place. Now she’ll do things like send a Slack reminder telling students to screenshot whatever they’re working on and drop it into Claude. No perfect prompt, no required outcome—just practice.
Skill files may be one of the most underrated ideas in agentic AI. Grace runs much of her business around three of them: a pipeline operator, a proposal maker, and a voice guide. Each is essentially a documented set of instructions Claude can reuse. She teaches students to build them the same way they would train a new employee: explain the job, walk through how it should be done, correct mistakes, and keep improving the instructions over time.
One of the best ways to sell someone on AI is to show them what it can do before explaining it. Grace gives new clients a password-protected, branded, interactive welcome experience she built in Claude. It’s part onboarding, part proposal, and part demo. By the time a client enters the password and starts clicking around, they already understand what makes this new way of working different.
Grace Clarke’s Claude Workflows for Business Automation and Rebuilding Gmail
https://www.chatprd.ai/how-i-ai/claude-workflows-for-business-automation-and-managing-gmail
↳ Automate Client Proposals and Onboarding with a Claude “Pipeline Operator”
↳ How to Rebuild Your Gmail Inbox Inside Claude to Manage Email
↳ Create an Automated Workout Tracker with a Simple Claude Voice Note
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
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2026-08-10 20:01:44
Grace Clarke is an AI educator and former marketing consultant who taught herself Claude Code earlier this year and built a curriculum out of the process. She now runs her entire service business on tools she’s built with Claude, including a pipeline operator, a proposal maker, and a Gmail replacement she created in under 30 minutes, and teaches individuals and teams to do the same.
Listen or watch on YouTube, Spotify, or Apple Podcasts
How to build an hourly pipeline in Claude that moves clients through your process automatically
Why Grace ditched traditional proposals for password-protected, interactive HTML documents built in Claude
How she uses a “voice guide” skill file so every Claude output sounds like her, not like AI slop
The two-step forcing function she teaches non-technical clients to build the muscle of opening Claude
Why she started building in Claude Code, then handed the work off to Cowork via a Markdown session file
How she replaced Gmail entirely with a custom inbox
Why she teaches “intent engineering” instead of prompt engineering, and what that looks like in practice
How she uses Claude on her phone, on walks, to track workouts and manage plants alongside client work
Bolt.new—Turn your idea into a real product
Hyperagent—Deploy fleets of agents that handle real work
(00:00) Grace’s background and why she started building with Claude
(04:48) The pipeline operator: what it is and how it runs her business every hour
(08:48) Building the muscle memory to use AI
(12:02) What goes into building a skill file (voice guide, proposal rules, versioning)
(13:50) How she built her proposal maker
(16:15) The voice guide: teaching Claude how she thinks, not just how she writes
(21:22) Live demo of the custom Gmail replacement built in Cowork
(30:44) Workout tracking, plant photos, and tiny daily Claude habits
(34:51) The biggest misconception holding people back from adopting AI
(38:36) What Grace does when Claude is not giving her what she wants
(40:38) Claude builds a proposal for Claire in real time
• Claude: https://claude.ai
• Claude Code: https://claude.ai/code
• Netlify: https://www.netlify.com
• Google Forms: https://forms.google.com
• Google Sheets: https://sheets.google.com
• Google Cloud (for service accounts and custom connectors): https://cloud.google.com
• Stratechery by Ben Thompson: https://stratechery.com
LinkedIn: https://www.linkedin.com/in/gracegclarke/
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2026-08-09 20:31:29
Adam Ward is the Head of Talent at Cursor, one of the fastest-growing developer tools in history. Before joining Cursor, he founded Growth by Design, an independent recruiting and talent strategy firm that helped build teams at the most ambitious AI and technology companies in the world. Adam has spent more than 20 years building elite, high-talent-density teams across the industry and is widely regarded as one of the most effective and creative recruiters in tech.
Listen on YouTube, Spotify, and Apple Podcasts
Inside today’s “tale of two cities” talent market
Why the traditional recruiting funnel—what Adam calls the “funnel of doom”—leads to mediocre hires
Adam’s three-step playbook: scoping, mapping, and relentless pursuit
The worst question to ask when sourcing great talent
The rise of the forward deployed engineer—and how to become one
The biggest mistake founders make when hiring their first recruiter
WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more
Mercury—Radically different banking, now with Command
• LinkedIn: https://www.linkedin.com/in/adampward
• Cursor: https://cursor.com
• Trilogy: https://trilogy.com
• Brie Wolfson on LinkedIn: https://www.linkedin.com/in/brie-wolfson-17758724
• Inside Cursor: https://colossus.com/article/inside-cursor
• SpaceX: https://www.spacex.com
• Joe Gebbia’s website: https://joegebbia.com
• The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell
• The Pitt on HBO Max: https://www.hbomax.com/shows/pitt-2024/e6e7bad9-d48d-4434-b334-7c651ffc4bdf
• The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f
• Granola: https://www.granola.ai
• Wispr Flow: https://wisprflow.ai
• 11 products I love, free for a year—the biggest Product Pass expansion in 2 years: https://www.lennysnewsletter.com/p/productpass-summer2026launch
• How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working
• The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham
• Emotional Intelligence: Why It Can Matter More Than IQ: https://www.amazon.com/dp/055338371X
• High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100
• Scaling People: Tactics for Management and Company Building: https://press.stripe.com/scaling-people
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.
2026-08-09 01:08:14
👋 Hello and welcome to this week’s edition of ✨ Community Wisdom ✨ a subscriber-only email, delivered every Saturday, highlighting the most helpful conversations in our members-only Slack community.
2026-08-05 20:04:01
AI writes most of my code now, and that created a new problem: a PR queue I couldn’t keep up with. In this episode, I walk through how I built Merge Mommy, a Vercel Eve agent that reads every PR after checks pass, scores it across six risk dimensions, auto-approves the low-risk ones, and pings me in Slack for anything that needs a human. I built the whole thing in one Codex session, it’s SOC 2 compatible, and it’s already cleared my backlog.
Listen or watch on YouTube, Spotify, or Apple Podcasts
Why AI-generated PRs create a review bottleneck and why the answer isn’t reviewing all of them
How Intercom 5x’d PR approval speed and reduced revert rates by putting AI in the review loop
Why Vercel Eve is the simplest framework I’ve found for deploying AI agents in Slack and GitHub
How I built a full PR review agent in Codex with one prompt and a few steering turns
The six components I use to score PR risk (blast radius, reversibility, data security, ops impact, verification gap, and change surface)
How I used Chrome browser use to handle Slack bot and GitHub app configuration so I never had to click through setup screens manually
Why auto-approved PRs can be SOC 2 compliant as long as the process is auditable, queryable, and in your risk policy
How to set up Slack escalation so low-risk PRs become a two-click merge with no manual review
WorkOS—Make your app Enterprise Ready, with SSO, SCIM, RBAC, and more
(00:00) The PR review backlog problem nobody’s talking about
(02:35) Why you don’t have to review every AI-generated PR
(05:14) How Intercom built AI-approved PRs (and proved they’re safer)
(06:10) How the Eve framework works (directory, skills, channels, connectors)
(09:16) The Codex prompt I used to build the entire bot
(11:36) What the agent actually does: read, score, approve, or escalate
(13:07) Setting up your Eve agent
(15:47) The six-component risk scoring model
(17:23) Merge Mommy in action: three live PR examples
(21:10) Recap and how to build your own version
• Vercel Eve: https://vercel.com/eve
• Vercel AI SDK: https://sdk.vercel.ai/
• Vercel Chat SDK: https://chat-sdk.dev/
• Codex (OpenAI): https://openai.com/codex
• AI is approving our pull requests: Here’s how we made it safe: https://www.intercom.com/blog/ai-is-approving-our-pull-requests-heres-how-we-made-it-safe/
• Review is the bottleneck now: How we let AI approve pull requests (safely): https://rewind.com/blog/ai-approve-pull-requests-safely/
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].