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Building on last week’s very exciting launch of Lenny’s Jobs (that’s a lot of likes!), I’m thrilled to bring you a companion post that will help you clarify what job to look for in the first place.

Cliff Maxwell teamed up with the legend Bobby Moesta (co-creator of the Jobs to Be Done framework and a two-time guest on Lenny’s Podcast) to build Vocation, a career navigation platform that helps professionals figure out their next step. Cliff’s own career has spanned building CPUs, education research, product management, venture capital, and serving as Chief of Staff to the late Clayton Christensen. Based on insights from over 1,000 interviews with professionals changing jobs and hundreds of one-on-one coaching clients, this hands-on guide will help you take a step back and connect with what you truly want from your work—and life.

Let’s get into it.

It’s a disorienting time to work in tech right now. For some, the rise of AI is a thrilling adventure, but for others, it’s a source of existential dread. No matter how you’re feeling, change is coming. The World Economic Forum reports that by 2030, 39% of today’s skills will change or become obsolete, and more than 90 million jobs will be displaced even as 170 million new jobs will be created.

Every generation of workers in tech has lived through recessions, layoffs, and technological change, but AI’s impact on work will be fundamentally different. It won’t just require new skills. It is redrawing the boundaries between roles and changing the day-to-day responsibilities inside them. Work may feel unstable now, but this will likely be the most stable it feels for a long time.

With this much uncertainty on the horizon, it is imperative that you develop the ability to navigate change. As your responsibilities shift and new opportunities emerge, the durable career advantage will come from knowing what kinds of problems, people, and environments bring out your best work—and having a repeatable process for identifying your next step even when the ultimate destination is unclear.

For the past year I have been building career navigation infrastructure with Bobby Moesta, one of the creators of the Jobs to Be Done framework and a two-time guest on Lenny’s Podcast. Bobby brings a product-oriented lens to career change: you are the customer, and the right next career move is the product you are looking to purchase.

Through more than 1,000 in-depth interviews with professionals changing jobs (some by choice, some by necessity)—and hundreds more people we have coached since—we identified what helps people make a successful job transition, and built a process to support them.

This is not a laundry list of LinkedIn hacks, resume tips, or ideas for how to automate your recruiting efforts. This is a step-by-step formula for designing a system that allows you to understand yourself, your context, and your best next steps when you’re in a state of change.

In this post, I’ll help you answer six fundamental questions that will instill confidence and focus anytime you are navigating a transition at work. Each question comes with exercises and tools to help you build understanding.

1. What kind of career progress do I want?

2. What career quest am I on?

3. Which work brings out my best?

4. What possible moves should I explore?

5. Which tradeoffs am I willing to make?

6. Can I get what I need without leaving?

Once you know your answers, you’ll be equipped to find your bearings now and every time the labor market throws you a curveball.

1. What kind of career progress do I want?

About a year ago, we coached an individual who, after spending several years at a startup that was running out of funding, assumed his next step was another early role in a venture-backed company.

After evaluating his core motivations and reflecting on his growing desire for impact, he found an opportunity to lead the entrepreneurship center at a local university, a job that he previously would have avoided and that none of his peers would have recommended. When he met with the administration, they effectively hired him on the spot, telling him, “You are exactly who we were looking for.” He’s now crushing it in his new role.

This story demonstrates the difference between career “progress” and “progression,” a distinction that is critical to understand when you are at a transition point in your career.

Progression is the philosophy that underpins most people’s mental model of careers. You start as an IC, get promoted, and up and up you go on the imaginary career ladder. This mindset will become increasingly less relevant as AI continues its march through knowledge work. Job boundaries and job titles will continue to blur, new job titles will emerge, and companies will struggle to neatly map job descriptions and career pathways into their org chart or KPIs.

Progress, on the other hand, is contextual and dynamic. It is ultimately a question of what your professional Job to Be Done is, and allows you to chart your own course rather than follow a single, narrow path of progression. Depending on your context, progress may be about autonomy and flexibility, preparing for the future, respect and recognition, or simply collecting a paycheck during a time of instability. It can look like a more traditional step up, but it may also look like a lateral move or even like a step back from the perspective of others—while it solves the most important problem in your life and gives you space and time to move forward later on.

A focus on progress is an active commitment to putting yourself in environments that will bring out your best. It helps you stand out amid the army of applicants all reaching for the same rung on the career ladder. Progress gives you the freedom to see your career in chapters and create space to be emergent rather than assuming you have to write one linear story all at once. To do this, you have to define the progress you’re seeking right now.

A 10-minute progress exercise

Take a blank page (or, if you’d like a live template, we made one for you here) and complete the sentence: I want to leave or change my current situation because…

Write down every friction or negative force you’re experiencing right now, or that you last experienced at work. We call these pushes. Do not polish the language. “My manager changes priorities every three days, and it’s getting exhausting” is more useful than “I want better leadership.” Unpack each one of these, and ask yourself “why” until you get to the root cause.

Then complete this sentence: I want my next chapter to give me…

List the desired outcomes you wish were true right now. We call these pulls. Again, make them concrete. “Control over when I do focused work” is more useful than “flexibility.”

Now circle the two or three pushes and two or three pulls that carry the most emotional weight. When you see the forces together, you can start to assemble what progress means for you, not for anyone else. For example, two people may both feel overburdened by new management, but one wants to join a more supportive team while the other is seeking more autonomy to work alone. Your unique combination of pushes and pulls forms the basis for your career quest, or the core motivation guiding your desire for change.

Below is an example of how this might look for someone seeking a new role:

2. What career quest am I on?

When you are seriously considering a job change, or when change is forced upon you, it’s easy to label and hold onto your most immediate feeling, whether that’s burnout, the excitement of something new, frustration, or disrespect. But underlying these emotions, less-obvious and subconscious factors are working together in a unique combination to animate your core motivation for change. This is your career quest.

Your quest for progress should inform every aspect of your job search, but most people skip this diagnosis and go directly to job boards, answer the recruiter’s call, or ask their network about job openings. They are halfway out the door before deciding what they even need this move to accomplish.

For example, I once coached an individual who was frustrated by the lack of leadership opportunities in his product role at a large tech company. When he was recruited to lead and grow the analytics function at a nearby startup, he felt excited and flattered to finally have the opportunity to grow a team.

But as we explored other pushes and pulls acting on him, a more nuanced story emerged. Despite the lack of leadership opportunities, he fundamentally liked his job. He was also in the middle of renovating his home, he wanted to be able to spend more time with his two young kids, and he wasn’t all that excited about leaving product for analytics.

The new role solved his most immediate and apparent problem, but it wouldn’t offer him the progress he needed both personally and professionally.

In our work with professionals looking to make a change, we have identified four common quests for progress that emerge again and again.

These quests are not mutually exclusive; you can be on multiple quests simultaneously, though one usually dominates. Even if you have been laid off and the immediate goal is “I need a job,” reflecting on these quests can help you decide which opportunities deserve your attention, and which you can avoid.

Quest 1: Get out

You have hit a wall you cannot fix from where you stand. Something about the manager, culture, leadership, or environment has made it hard to succeed or remain healthy. The dominant feeling is escape, and the desire to get out is usually quick, not something you stew on for months at a time.

Common pushes:

• Feeling disrespected or not trusted to do great work

• Working for a manager who is wearing you down

• Losing trust or respect in leadership and/or your peers

• Not seeing a place to grow in your current organization

Common pulls:

• The pulls are often vague: a fresh start, a healthier environment, or simply “anywhere but here.”

• When someone is looking to get out, they often accept the first available escape but run the risk of landing in the same conditions at a different company.

Quest 2: Regain control

Work has swallowed too much of your life, even if you still enjoy the work itself.

This quest often follows a change outside work: a new child, caregiving responsibilities, a health issue, or a shift in what you want your life to look like. It can also emerge when a previously manageable role becomes chaotic, or when the way your manager or company leadership is running things no longer works for you.

Common pushes:

• Feeling worn down by management

• Work is dominating your life and you’re starting to make sacrifices

• Unpredictable demands, or feeling challenged beyond your ability

• Little control over your schedule or priorities

• A workload that no longer feels sustainable

Common pulls:

• More time to spend with others

• A job location that fits better into your personal life

• An employer who properly values your experience and credentials

• A scope of responsibility you can sustain

Quest 3: Regain alignment

Your job has drifted away from what you do best, what you value, or what you originally agreed to do. You may still be performing well. In some cases, that is part of the problem: you have become useful for work that does not fit you, and you don’t feel respected.

Common pushes:

• Being underused or miscast

• Watching your responsibilities move away from your strengths

• A growing gap between your values and the company’s

• Feeling unchallenged or bored

• Not seeing a clear place to grow inside the organization

Common pulls:

• Work that uses your full capabilities

• Greater alignment with your values

• Recognition that matches your contribution

• A role built around the things you do unusually well

Quest 4: Take the next step

You have completed something meaningful, mastered the role, or reached a point where the work no longer stretches you. Alternatively, you’ve hit a personal milestone (baby, move, etc.) and want a change. You are not necessarily unhappy. You are simply ready to be challenged and get the support you need to grow.

Common pushes:

• Hitting a personal or professional milestone

• Feeling unchallenged or bored

• Not seeing a clear place to grow

• Needing to provide more support for family or loved ones

Common pulls:

• Feeling like a job is a clear step forward

• Joining a tight-knit team you can count on

• Developing new skills as part of a stepping stone to something else

A quick quest diagnostic

Finish this sentence: More than anything, I need my next move to…

• Get me away from a situation I can no longer tolerate.

• Give me control over my time, workload, or life again.

• Let me do work that fits my strengths and values.

• Give me a new challenge or chapter.

How you finish the sentence will not capture every part of your situation, but it will usually reveal which quest you may be on—and also help you label what you don’t need right now.

3. Which work brings out my best?

Most professionals know their skills better than they know the conditions that allow them to do their best work. You take on responsibilities, become known for certain outcomes, develop valuable skills, but are often too busy doing the job to understand the circumstances you need to be successful and feel fulfilled.

Then a shiny title or compensation increase appears, and you accept a role that actually makes you miserable—an outcome common to ICs-turned-managers who realize too late how much they hate management.

You need to figure out what you need before you switch jobs (or are compelled to switch), not figure it out by switching. This is what building your energy profile is all about: it provides a blueprint for evaluating new opportunities, along with a starting point for questions you can ask a hiring manager or peer as you explore open roles.

Build your energy profile

To get started, grab some Post-it notes or spin up a Miro board, and make a simple timeline of roles you’ve held and the title, company, and duration for each role (including your current role if employed). If you want a pre-built template, we’ve got one here. The steps below will show you how to fill this out, and I’ve included an example of the beginnings of my own energy profile:

Step 1: Audit your calendar

Pull up the past month of your work calendar and list what you actually did, hour by hour.

Do not use the language of your job description. Describe the activity:

• Collaborative planning meeting

• Individual research

• Customer call

• Writing a strategy document

To help you through this, you can integrate your calendar with an AI agent of your choice (via a simple connection or MCP) and use this simple prompt:

“For the past month, make a list of core meetings and time blocks on my calendar and ask me 1-2 questions about each to uncover what I actually did during those blocks of time. For example, if you see a ‘team meeting,’ ask me briefly what my role was and how I contributed. Then produce a list of the 8-10 core activities in my work life.”

Step 2: List your energizers

Which tasks energized you?

Look for work where you lost track of time, volunteered extra effort, or kept thinking after the meeting ended. Include the tasks that left you with more energy afterward.

Step 3: List your drainers

Which tasks did you avoid, postpone, rush through, or perform adequately just to get them over with?

Include work you are good at but dislike. Competence and energy are not the same thing. Many careers get built around things a person does well but does not want to keep doing.

Step 4: Repeat the exercise across previous jobs

Review your last job, then the one before that. You can’t go hour by hour, but for each role there were likely six to eight core responsibilities or tasks you engaged in on a regular basis.

As you complete this, you will begin to see a history of your career written in the language of energy instead of titles or responsibilities.

Step 5: Identify themes among your energizers and drainers

Revisit the activities you collected in the last step and see if you can identify broader themes or clusters that emerge from tasks that energize and drain you. As you do this, clarity is key. “Working with others” is not a clear theme. Neither is “heads-down work.” Working with whom? On what? Under which conditions? Similarly, “office politics” is not a clear theme for what drains you. What relationship dynamics are problematic? What decision-making processes don’t work for you?

To help you do this, you can ask questions like:

• What is this more like?

• What is this less like?

• Which conditions need to be present?

Below is an example of unpacking a theme that emerged when I built my own energy profile: “environments that allow me to become an expert at the intersection of people and technology.”

As your themes begin to emerge, you’ll realize where you shine, where you check out, and what you want out of your next role. This is the foundational work necessary to begin prototyping potential opportunities.

4. What possible moves should I explore?

Read more

Grok Bot + Grok 4.6—what’s great (and what’s still hype)

Brought to you by:

Bolt.new—Turn your idea into a real product

Jira AI SDLC—Get your tokens’ worth with Jira

In this solo episode, Claire tests Grok Bot, Cursor Origin, and Grok 4.6 to figure out what’s genuinely useful and what’s still mostly hype. She shares the Grok Bot feature that immediately won her over, why she isn’t ready to replace GitHub with Origin, and how Grok 4.6 performed against GPT-5.6, Claude Sonnet 5, and Opus 5 in her own blind evaluations.

Biggest takeaways:

1. Grok Bot’s multi-account connectors solve a problem every other agent platform seems to ignore. Most platforms assume each person has one Gmail account and one Slack workspace. Claire has four email addresses and seven Slack workspaces. Grok Bot lets her connect all of them to a single bot, which made it genuinely useful from day one in a way that Codex and Claude still have not matched.

2. Grok Bot’s simplicity is both its greatest strength and its biggest limitation. Setup is fast, the iMessage-style interface is clean, and the built-in plugins actually work. But people who enjoy customizing their agents, choosing models, shaping personalities, and tinkering with every detail may find it almost too polished. Claire loves her OpenClaw agents partly because they are chaotic and high-maintenance. So far, Grok Bot has not given her much to wrestle with.

3. Cursor Origin is a compelling vision that is not quite ready for prime time. An agent-native alternative to GitHub makes a lot of sense, especially one where Bugbot, Cursor, and the entire pull request workflow are designed around how coding agents actually work. Today, though, Origin still feels like a more attractive version of GitHub with fewer features. Teams that rely heavily on GitHub Actions, code owners, and existing automations will need a much stronger reason to migrate.

4. Grok 4.6 is a genuine frontier-model competitor. That conclusion did not come from someone else’s leaderboard. Claire runs her evaluations blind, grades the outputs herself, and gives her own judgment 70% of the final weight. Grok 4.6 finished alongside GPT-5.6 Sol at the top of the Claire Index, ahead of both Sonnet 5 and Opus 5.

5. For sharp, enjoyable agent conversations, Sonnet 5 is still the model to beat. When Claire wants an OpenClaw agent that is concise, responsive, and fun to talk with, Sonnet 5 continues to win. It has a conversational rhythm that feels more like working with a strong collaborator than issuing commands to a tool. Grok 4.6 does not yet compete in that category.

6. Cursor and xAI are assembling a surprisingly coherent enterprise stack. Grok Bot serves knowledge workers, Origin handles code hosting, Grok 4.6 provides a capable default model, and the Cursor IDE already sits at the center of many developers’ workflows. None of the pieces is perfect on its own, but together they are beginning to look like a credible enterprise platform. Large companies often prefer one vendor that can own the entire experience, and Cursor is increasingly positioned to become that vendor.

I spent $20,000 on Devin in a month. Here’s what I learned | Ryan Carson (solo founder)

Brought to you by:

• WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

• Jira AI SDLC—Get your tokens’ worth with Jira

Ryan Carson is a five-time founder and the solo founder of Untangle, a B2B SaaS platform for family law firms. In this episode, he breaks down how he manages up to 15 AI agents at once, ships as many as 40 pull requests a day, and uses Devin, Codex, and Claude Code to handle everything from engineering and QA to customer success and investor updates. He also shares why more AI output doesn’t necessarily lead to a better product, how a handwritten priority list keeps his agents focused, and why talking to one real customer changed the direction of his entire company.

Biggest takeaways:

1. The most important skill for a solo founder may be managing agents, not writing code. Ryan runs 10 to 15 Devin threads at once, organized into P0, P1, P2, and Bugs folders. He treats each thread the way a good manager treats a direct report: give it a clear goal, set the right priority, and avoid unnecessary hand-holding. That organizational discipline is what separates founders who gain real leverage from AI from those who simply accumulate open tabs.

2. A piece of paper can still be the best tool for protecting attention. Despite working across eight screens, Ryan keeps a handwritten list of his weekly priorities beside him. The simplicity is intentional. When agents are constantly generating updates, questions, and decisions, that physical list keeps him anchored to the three things that matter most before he gets pulled into whatever Devin surfaced overnight.

3. Ryan built an AI playbook that functions like a customer success team. His Watchdog workflow reviews every law firm account, pulls recent activity and errors from Sentry and internal logs, identifies the three most important problems, and checks whether a recent pull request has already fixed each one. Everything appears in a single Devin thread. Whenever Ryan feels the familiar anxiety of not knowing what is happening across his customer base, he runs Watchdog and quickly gets back up to speed.

4. Producing more with AI does not automatically lead to a better product. Both Ryan and Claire are skeptical of letting agents work without constraints overnight. Frontier models can generate an enormous amount of output, but they do not know what customers actually need. Product ideas, priorities, and market judgment still have to come from a human who talks to users. Ryan found product-market fit for Untangle not by shipping more code but by landing one meeting with family law attorney Renee Bauer and listening carefully.

5. Cloud agents may handle most engineering work, but Codex still shines when the frontend requires close attention. Ryan uses Devin for cloud-based work across bugs, pull requests, investor updates, and customer triage. He turns to Codex when a feature is visually complex and he needs to stay close to the implementation. The distinction is not about loyalty to a particular tool. It comes down to latency, browser access, and the ability to inspect and refine the interface in real time.

6. Coding agents can operate far beyond the codebase. Claire uses Devin for deal desk, custom quotes, and customer triage. Ryan uses it to prepare investor updates through a reusable skill. Both approach these agents with a broader question: What could someone accomplish if they understood the entire codebase and could write software to solve almost any problem? That framing reveals business uses that would never emerge from treating an agent as a simple coding assistant.

7. The best engineering interview may be a screen recording of the actual work. Ryan asks candidates to record themselves building a feature inside an existing application, with the entire screen visible and no introductory meeting required. In the next stage, he gives them access to Devin and reviews the replay of how they worked with it. This shows him how candidates think, build, and manage an agent under realistic conditions, which he finds far more revealing than a typical behavioral interview.

8. The strongest design workflow pairs Claude’s system thinking with Codex’s implementation ability. Claire used Claude Design to break a Figma file into reusable design tokens and a design.md specification. She then gave that specification to Codex, which created shared components across a monorepo. Claude is particularly good at translating a visual system into a portable spec. Codex is better at turning that spec into working, interconnected code. The workflow succeeds because each model is assigned the part it does best.

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.

Ryan Carson is a five-time founder and the current solo founder of Untangle, a B2B SaaS platform for family law firms. Before Untangle, he co-founded Treehouse, an online coding education platform, and has spent the better part of two decades building and leading tech companies. He’s active on X, where he shares his solo founder journey in real time, including what he actually spends on AI tools each month.

What you’ll learn:

1. Why Ryan manages 15 concurrent Devin agents with a folder system and a piece of paper, not a dashboard

2. The Watchdog playbook: what he built to replace a customer success team across every law firm account

3. How his LAN PR skill closes the loop on 40 daily PRs without a QA team reviewing a single one

4. Why he moved off local agents almost entirely, and the one situation where he still reaches for Codex

5. The design workflow we’re both using: Claude Design into a Markdown spec, then Codex to build the real thing

6. What he found when he got away from his computer and met a real customer, and why it changed his entire product direction

7. How he’s hiring his first engineer without a single phone screen or interview

8. Why we both think more AI output is actually the wrong goal, and what to optimize for instead

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Jira AI SDLC—Get your tokens’ worth with Jira

In this episode, we cover:

(00:00) Introduction to Ryan Carson

(02:55) Ryan’s update: Untangle, the divorce PMF pivot, and B2B growth

(07:35) Ryan’s current Devin stack: folders, P0 threads, and the paper list

(16:29) Watchdog playbook: account monitoring across every firm

(18:09) Managing agent decision fatigue: Ryan’s method vs. Claire’s

(20:32) Producing more output does not make a better product

(22:47) Using cloud agents for ops beyond just code

(25:14) When to use Codex vs. Devin vs. Claude Code

(27:15) Merge Mommy recap

(28:15) LAN PR skill: review loops, video walkthrough, and auto-merge

(30:20) Slack vs. Devin threads for async team communication

(35:58) Claude Design plus Codex for building a technical design system

(39:00) EA tools: Polly the OpenClaw vs. Claude Code on a Mac Mini

(42:09) Quick recap and final thoughts

Tools referenced:

• Devin (Cognition): https://www.cognition.ai/

• Codex (OpenAI): https://openai.com/codex

• Claude Code/Claude Design (Anthropic): https://www.anthropic.com/claude

• OpenClaw (Claude-based desktop client): https://openclaw.ai

• Cursor: https://www.cursor.com/

• BugBot (Devin’s built-in PR review): https://cursor.com/bugbot

• Sentry (error monitoring referenced in Watchdog): https://sentry.io/

• Ugmonk (analog to-do system): https://ugmonk.com/

Other references:

• Devin playbooks/skills documentation: https://docs.cognition.ai/

• Jack Dorsey/Buzz (async-first communication referenced): https://buzz.new/

• Merge Mommy (Claire’s Eve agent for PR risk scoring, deployed on Vercel): https://www.lennysnewsletter.com/p/build-an-ai-code-review-bot-in-30

Where to find Ryan Carson:

X: https://x.com/ryancarson

Untangle: https://untangle.us

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 jordan@penname.co.

Jen Abel is the co-founder of JJellyfish and GM of enterprise sales at State Affairs. She is widely regarded as one of the sharpest practitioners in enterprise sales, and for that reason, this is her third visit to the podcast. In our first conversation we went deep on founder-led sales; in our second we mapped the $1M–$10M playbook. This time we do something I’ve never seen on another podcast: walk step by step through the full enterprise sales cycle. Most people think it’s five steps. Jen shows it’s closer to 15.

In our in-depth conversation, we discuss:

1. Why the standard five-stage CRM pipeline is a forecasting tool, not a sales process, and what the real 15-step cycle looks like

2. The “pincer model” for landing the first meeting at the executive and N-minus-one level simultaneously

3. How to craft a two-to-three-sentence message around giving them “alpha”

4. How to run an intro call that extracts maximum intelligence before you ever show a demo

5. The two-to-three-day pilot structure, how to define success jointly, and when to charge for a longer pilot versus giving it away

6. Navigating pricing, procurement, redline negotiations, and the final signature without losing momentum

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

Where to find Jen Abel:

• X: https://x.com/jjen_abel

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

• Website: https://www.jjellyfish.com

Referenced:

• State Affairs: https://stateaffairs.com

• The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel

• “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr

• SpaceX: https://www.spacex.com

• Lemlist: https://www.lemlist.com

• Palantir: https://www.palantir.com

• Jason Lemkin on X: https://x.com/jasonlk

• We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents

• Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org

• Careers at State Affairs: https://stateaffairs.com/careers

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

Read more

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This week I’m doing a solo breakdown of everything xAI and Cursor have shipped recently, including Grok Bot, Cursor Origin, and the Grok 4.6 model. I set up five Grok Bots, ran Grok 4.6 through my Claire Weighted Index against GPT-5.6 Sol, Claude Sonnet 5, and Opus 5, and spent time actually using Origin as a GitHub replacement. Here’s what’s worth your attention, what’s overhyped, and where I’m personally putting my time.

What you’ll learn:

1. The one Grok Bot feature no other agent platform has shipped yet, and why it made me actually use the product

2. What a week of real Grok Bot use revealed, and why I still reach for my OpenClaws

3. Whether Cursor Origin is a GitHub replacement or just a pretty redesign

4. Where Grok 4.6 landed on the Claire Index, and the one category where it genuinely surprised me

Brought to you by:

Bolt.new—Turn your idea into a real product

Jira AI SDLC—Get your tokens’ worth with Jira

In this episode, we cover:

(00:00) Why everyone’s quietly switching to Grok

(01:52) Grok Bot overview and setup

(03:22) My 5 Grok Bots

(04:30) The killer feature: multi-account connectors

(06:07) Grok Bot’s virtual machine and how it actually works

(06:41) Experience overview

(07:35) What I don’t love about Grok Bot

(10:08) Grok Bot use cases and my honest verdict

(12:20) Cursor Origin: the agent-native GitHub replacement

(13:47) What Origin actually looks like in practice

(14:59) Why I’m not switching from GitHub yet

(17:42) What would get me to move over

(18:52) Grok 4.6 and the How I AI Vibe bench

(20:41) Claire Index results: where Grok 4.6 ranked

(23:03) Design evals: where Grok surprised me

(25:00) My conclusion and how I’m splitting my time now

Tools referenced:

• Grok Bot: https://x.ai/bot

• Cursor: https://cursor.com/home

• Cursor Origin: https://cursor.com/origin

• OpenClaw: https://openclaw.ai/

• GitHub: https://github.com

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 jordan@penname.co.

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P.S. Get a full free year of Cursor, Notion, Replit, Lovable, Factory, Wispr Flow, Linear, ElevenLabs, PostHog, Brain.fm, Waking Up, and more, by becoming an Insider subscriber (while supplies last). Learn more.

My goal is to help you succeed in your career.

I’ve spent thousands of hours on my newsletter and podcast sharing advice on how to get better at your work. But all that advice doesn’t mean much if you don’t actually have a job—or work you’re excited about.

Over the past six months, I’ve been thinking long and hard about what more I can do to help people who are struggling to find a job they love.

Today I’m excited to announce the launch of Lenny’s Jobs—the best place in the world to find, vet, and land your dream job 🙌

What makes Lenny’s Jobs unique and awesome:

1. A laser focus on four builder roles at tech companies: product management, engineering, design, and growth/marketing. We focus exclusively on these roles because they’re what most of you are looking for—and because these roles are starting to meld together. We aggregate open roles from top startups and big tech companies, and unlike any other job directory, we vet every company we include and filter out ghost roles and generic staffing-agency posts. This is the highest-quality directory of open tech roles you’ll find anywhere.

2. Unlisted roles you won’t find on any other job site. Every month I poll my audience on X and LinkedIn for roles they’re hiring for, many of which aren’t listed elsewhere. Along with submissions from our private reader Slack community, we integrate these roles into the directory. Look out for the “Lenny’s Community” tag in the feed.

3. The Lenny 100. To help you prioritize your search, I’ve curated a list of the top 100 companies I’d most want to join if I were looking for a job. These are companies that IMHO have the highest talent density, are tackling the most ambitious problems, have the biggest upside potential—and are actively hiring. I’ll update this list regularly.

4. Custom-built AI tools embedded within each job post. For every role, you can quickly rate your fit, prep for the interview, develop an outreach plan, customize your resume, and more. I’m really excited about the potential here.

5. A custom-built AI interview and career coach. Incorporating Noam Segal’s incredible set of AI skills that readers have been raving about, the AI coach will help you with everything from building your pitch to doing mock interviews to analyzing and debriefing to handling compensation conversations and negotiating job offers. I don’t believe there’s anything out there like this, and we have some big ideas for where this coach can go. Try it out!

6. An AI agent that emails you the best new jobs for you. Tell us what you’re looking for and we’ll automatically notify you of newly posted jobs that would be a great fit. Set it up once and you’re all set. This is the only feature available exclusively for paid subscribers.

7. Rich company data and tech-specific filters. Every job post includes up-to-date data on company funding, layoff history, headcount growth, compensation, and employee sentiment, so you can quickly evaluate opportunities without tab-hopping across six different sites. Plus, more than 100 tech-specific search filters—including investors, valuation, and tech stack—help you find exactly what you’re looking for.

8. Curated interview and career resources. I’ve organized a small but powerful collection of my favorite third-party content, tools, and courses that have moved the needle for many people I know on interview prep, speaking confidence, choosing where to work, and more. I also share my favorite podcast episodes and newsletter posts on career and interviewing advice.

The site is free to use (and will continue to be), but paid Lenny’s Newsletter subscribers get higher AI feature limits, unlimited personalized results, and the proactive AI agent that notifies you about new jobs. To activate these benefits, first create a Lenny’s Jobs account, then link your paid subscription here.

A huge shout-out to Amit Taylor, founder of TrueUp, who I’ve partnered with on numerous State of the Product Job Market reports, for building this site with me. Also, a big thank-you to Ben Erez, Tal Raviv, and Noam Segal for tons of great feedback as this came together. We’re excited to get your feedback and keep making it better and more useful to you. And we’ve got some big plans:

1. Integrated white-glove recruiting services: direct intros between standout candidates and great companies

2. Personalized career and skills development: coaching, training, and curated recommendations for the best stuff out there

3. Ongoing state-of-the-job-market reports: data-backed updates on how the job market, roles, and skills are changing so that you can stay ahead

I don’t want to overpromise here, but I firmly believe there’s no better place for product managers, engineers, designers, and growth/marketing professionals to discover high-quality open roles.

Check out Lenny’s Jobs and let us know what you think.

P.S. See if you can find the Easter egg where you can watch the latest episode of Lenny’s Podcast while browsing the site.

If you’re finding this newsletter valuable, share it with a friend, and consider subscribing if you haven’t already. There are group discounts and gift options available.

Subscribe now

Sincerely,

Lenny 👋

How a solo founder used Codex and ChatGPT to launch a fashion brand without engineers | Yana Welinder

Brought to you by:

• Merge—Connective infrastructure for production AI

• Jira AI SDLC—Get your tokens’ worth with Jira

Yana Welinder is the solo founder of Yana Bana, an AI-native fashion brand she’s building without an engineering team. In this episode, she walks through how she uses ChatGPT and Codex to turn hand-drawn sketches into realistic product images, operate professional 3D fashion software, research and contact manufacturers, and build a complete e-commerce site with voting and payments.

Biggest takeaways:

1. The prompt is the spec, and the spec is everything. Before generating a single image, Yana creates a detailed “fashion prompt” describing the silhouette, the way the fabric should behave and move, and even the sound it should make. That upfront work leads to dramatically better results. The lesson applies far beyond fashion: the more clearly someone can define what “good” looks like, the better both AI and humans can deliver it.

2. For designers, following the vision matters more than producing something impressive. Many image models can create a beautiful garment, but it often looks like something that already exists. ChatGPT Images 2.0 stays much closer to Yana’s original sketches. For creative professionals with a specific point of view, accurately following the design is far more valuable than generating something flashy.

3. AI agents can make specialized software accessible without years of training. Yana used Codex to operate CLO, a professional 3D fashion design tool, and create the CAD files she needed for 3D printing, even though she had never learned to use the software herself. This points to a much bigger shift: people may no longer need to master every complicated tool before they can produce professional work with it.

4. AI is making previously impractical ideas possible. Yana designed a Ruth Asawa–inspired gown featuring large sculptural forms that would have been extremely difficult to produce before. The limitation was not the lack of 3D printing but the enormous amount of CAD work required to prepare the design. AI removed that bottleneck. Similar bottlenecks are hiding in nearly every industry, often preventing great ideas from being worth pursuing.

5. The near-term future is agents working through purpose-built software. Codex cannot create a finished CAD file on its own. But Codex operating CLO can produce exactly what Yana needs. That same pattern appears throughout her workflow: the AI serves as the orchestration layer, while specialized software handles the execution. SaaS is not disappearing; it is gaining a new kind of user.

6. Voice-first, asynchronous work is already changing what one person can accomplish. Yana can start a deep research task, step away to sew or drape fabric, then return and continue the work through voice. The AI keeps working while she focuses on the physical parts of her business. For a solo founder, this kind of asynchronous collaboration can dramatically expand what fits into a single day.

7. When the best path is unclear, humans and AI can work in parallel. One of Yana’s hardest remaining challenges is turning her designs into accurate sewing patterns. Instead of betting entirely on one approach, she has human patternmakers and Codex working on the problem at the same time. It is a practical way to move quickly under uncertainty: test both paths, compare the results, and let the better solution win.

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.

Yana Welinder is the solo founder of Yana Bana, an AI-native fashion brand built with AI as her technical co-founder, starting from hand-drawn sketches and ending with runway photos, CAD files for 3D printing, and a live Stripe-connected pre-order site—no engineers required. A former product leader, she brings an operator’s rigor to her creative process: her “fashion prompt” is a detailed spec covering silhouette, volume, fabric beavior, movement, and sound, and watching her use Codex plus computer use to navigate 3D design software that’s entirely new to her is a clarifying demo of what today’s toolset actually makes possible.

What you’ll learn:

1. How Yana uses a custom fashion prompt as a technical spec to get consistent, realistic, on-design outputs

2. Why ChatGPT Images 2.0 outperforms other models for fashion design

3. How she uses Codex plus computer use to operate CAD and fashion software she’s never personally learned

4. The workflow for taking a garment from hand-drawn sketch to product photo, runway photo, and influencer shot in a single session

5. How she ran vendor outreach end to end using deep research and browser use

6. How she built a full e-commerce site with voting, databases, and Stripe integration

7. Why she’s testing human patternmakers and Codex in parallel

Brought to you by:

Merge—Connective infrastructure for production AI

Jira AI SDLC—Get your tokens’ worth with Jira

In this episode, we cover:

(00:00) Introducing Yana Welinder and Yana Bana

(02:38) Tour of the Yana Bana site

(05:20) The fashion prompt stack

(07:39) Live demo: generating a jacket from a prompt in ChatGPT

(10:01) Why Image Gen 2.0 beats other models

(11:51) The “prompt as spec” principle

(14:02) Iterating the design

(17:12) Using Codex and computer use to build CAD files in 3D software

(20:50) Vendor research, outreach emails, and Superhuman browser use

(23:34) Building the full e-commerce site

(27:40) Quick recap and what’s still hard

(30:05) How Yana prompts when AI pushes back

(31:15) Where to find Yana and how to vote on her garments

Tools referenced:

• ChatGPT (Images 2.0): https://chat.openai.com

• Codex (OpenAI): https://openai.com/codex

• CLO 3D (fashion pattern software): https://www.clo3d.com

• Vercel: https://vercel.com

• GitHub: https://github.com

• Stripe: https://stripe.com

• Superhuman: https://superhuman.com

Other references:

• Ruth Asawa: https://ruthasawa.com

• SFMOMA (Ruth Asawa): https://www.sfmoma.org/artist/Ruth_Asawa/

Where to find Yana Welinder:

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

X: https://x.com/yanabana

Website: https://www.yanabana.com

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 jordan@penname.co.

Ian Silber is the head of product design at OpenAI, where he has led the design of ChatGPT, Codex, and all of OpenAI’s product experience for the past three years. Before OpenAI, he was at Artifact, the AI-powered news app built by the founders of Instagram. Prior to that, he spent eight years at Instagram, where he worked on products including Reels. Ian is one of the most consequential designers working in AI today, and he takes us inside how OpenAI designs ChatGPT, Codex, and the future of how we will interact with AI.

In our in-depth conversation, we discuss:

1. Why Ian believes this is the best time in history to be a product designer

2. Why engineers 10x’d with AI but design teams haven’t

3. What OpenAI looks for when hiring designers

4. “Just do less”: Ian’s counterintuitive advice to his designers

5. The future of ChatGPT as a super app

6. Where humans still win: user understanding, invention, and point of view

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

Where to find Ian Silber:

• X: https://x.com/iansilber

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

• Website: https://iansilber.com

Referenced:

• OpenAI: https://openai.com

• How tech workers are feeling in 2026: a workforce splitting in two: https://www.lennysnewsletter.com/p/how-tech-workers-are-feeling-in-2026

• Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom

• 3 Spiderman Pointing meme template: https://www.kapwing.com/explore/3-spiderman-pointing-meme-template

• OpenAI Codex lead on the new shape of product work | Andrew Ambrosino: https://www.lennysnewsletter.com/p/openai-codex-lead-on-the-new-shape

• Notion: https://www.notion.com

• The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead

• Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein

• Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next

• ChatGPT Work: https://openai.com/chatgpt-work

• OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai

• Please Stop the AI Confidence Theater: https://www.elenaverna.com/p/please-stop-the-ai-confidence-theater

• The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna

• Maybe Happy Ending: https://www.maybehappyending.com

• The Invite: https://www.imdb.com/title/tt14173636

• Rivian: https://rivian.com

• Waymo: https://waymo.com

• Groupon: https://www.groupon.com

• How a VC and a tech founder used AI to launch a brick-and-mortar business in their spare time | Andrew Mason (CEO of Descript) and Nabeel Hyatt (General Partner at Spark Capital): https://www.lennysnewsletter.com/p/how-a-vc-and-a-tech-founder-used

• Andrew Mason on X: https://x.com/andrewmason

• Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom

• Sam Altman on X: https://x.com/sama

Recommended book:

• The Design of Everyday Things: https://www.amazon.com/dp/0465050654

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

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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.

The three founder archetypes

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:

1. The “Problem” founder: The person who started a company to solve their own problem

2. The “Insight” founder: The person who started a company to solve a problem only they saw

3. 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:

1. Goal: What specifically your content strategy is meant to achieve

2. Voice: How you should sound

3. Messaging pillars: What you should talk about

4. 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.

Archetype 1: The “Problem” founder

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.

The Problem founder playbook

• 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?

Archetype 2: The “Insight” founder

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.

The Insight founder playbook

• 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?

Archetype 3: The “Vision” founder

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.

The Vision founder playbook

• 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?

When (and how) to use AI in your content process

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Build an AI code review bot in 30 minutes with Vercel Eve

Brought to you by:

WorkOS—Make your app Enterprise Ready, with SSO, SCIM, RBAC, and more

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.

Biggest takeaways:

1. 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.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

7. 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.

8. 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.

9. 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.

Claude Code for normal people: skills, voice mode, and how to collaborate with AI

Brought to you by

• Bolt.new—Turn your idea into a real product

• Hyperagent—Deploy fleets of agents that handle real work

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.

Biggest takeaways:

1. 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.

2. 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.

3. 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.

4. 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.

5. 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.

6. 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.

7. 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.

8. 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.

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.

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.

What you’ll learn:

1. How to build an hourly pipeline in Claude that moves clients through your process automatically

2. Why Grace ditched traditional proposals for password-protected, interactive HTML documents built in Claude

3. How she uses a “voice guide” skill file so every Claude output sounds like her, not like AI slop

4. The two-step forcing function she teaches non-technical clients to build the muscle of opening Claude

5. Why she started building in Claude Code, then handed the work off to Cowork via a Markdown session file

6. How she replaced Gmail entirely with a custom inbox

7. Why she teaches “intent engineering” instead of prompt engineering, and what that looks like in practice

8. How she uses Claude on her phone, on walks, to track workouts and manage plants alongside client work

Brought to you by:

Bolt.new—Turn your idea into a real product

Hyperagent—Deploy fleets of agents that handle real work

In this episode, we cover:

(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

Tools referenced:

• 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

Other reference:

• Stratechery by Ben Thompson: https://stratechery.com

Where to find Grace Clarke:

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

X: https://x.com/graceclarke

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 jordan@penname.co.

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.

In our in-depth conversation, we discuss:

1. Inside today’s “tale of two cities” talent market

2. Why the traditional recruiting funnel—what Adam calls the “funnel of doom”—leads to mediocre hires

3. Adam’s three-step playbook: scoping, mapping, and relentless pursuit

4. The worst question to ask when sourcing great talent

5. The rise of the forward deployed engineer—and how to become one

6. The biggest mistake founders make when hiring their first recruiter

Brought to you by:

WorkOS—Make your app enterprise-ready, with SSO, SCIM, RBAC, and more

Mercury—Radically different banking, now with Command

Where to find Adam Ward

• X: https://x.com/wardadamp

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

Referenced:

• 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

Recommended books:

• 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 podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

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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.

What you’ll learn:

1. Why AI-generated PRs create a review bottleneck and why the answer isn’t reviewing all of them

2. How Intercom 5x’d PR approval speed and reduced revert rates by putting AI in the review loop

3. Why Vercel Eve is the simplest framework I’ve found for deploying AI agents in Slack and GitHub

4. How I built a full PR review agent in Codex with one prompt and a few steering turns

5. The six components I use to score PR risk (blast radius, reversibility, data security, ops impact, verification gap, and change surface)

6. How I used Chrome browser use to handle Slack bot and GitHub app configuration so I never had to click through setup screens manually

7. Why auto-approved PRs can be SOC 2 compliant as long as the process is auditable, queryable, and in your risk policy

8. How to set up Slack escalation so low-risk PRs become a two-click merge with no manual review

Brought to you by:

WorkOS—Make your app Enterprise Ready, with SSO, SCIM, RBAC, and more

In this episode, we cover:

(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

Tools referenced:

• 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

Other references:

• 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/

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 jordan@penname.co.

Subscribe now

P.S. Get a full free year of Cursor, Notion, Replit, Lovable, Factory, Wispr Flow, Linear, ElevenLabs, PostHog, Brain.fm, Waking Up, and more, by becoming an Insider subscriber (while supplies last). Learn more.

Molly Graham’s first guest post, The Waterline Model, quickly rose to be my 7th most popular post of all time—extra impressive for not being about AI. I suspect this post will rise even faster.

Below, Molly introduces the concept of emergence as an alternative to conventional career advice. What she describes is exactly what my career path has looked like, and it’s a pattern I’ve seen across most of the successful people I know. If you’re worried about not having a plan for your career, or if your plan isn’t going according to plan, you’ll feel better after reading this post.

If you’re not familiar with Molly, she’s . . . incredible. She was an early employee at Google and Facebook, COO at Quip (working closely with Bret Taylor), helped build the Chan Zuckerberg Initiative (working closely with Priscilla Chan and Mark Zuckerberg), co-founder of Glue Club, co-founder of The Guild, and most recently, host of TED’s WorkLife podcast (taking over for Adam Grant). At 22, she was leading 75-day wilderness expeditions in Patagonia and Alaska for the National Outdoor Leadership School. Tl;dr, she’s seen and done a lot.

Let’s get into it.

Sheryl Sandberg once told me that everyone should have a two-year plan and a 20-year plan. The first, I could figure out; 20 always looked fuzzy.

I’ve never had a career plan. And I’ve always felt a little broken because of it.

We’re taught that careers should look like a set of stairs—you decide where you want to end up and march upward. When you look at many successful people, their careers can often appear like that from the outside.

My resume includes jobs at some big-name companies, C-level titles, and fun-looking solo ventures, but I have always wondered if it suffered from lack of design or clear destination in mind. At times, it has felt more like a game of chutes and ladders than any kind of stairs.

But recently, a conversation with Mark Rober completely changed how I think about my career. Don’t know Mark? Ask any 8-year-old who he is. He is one of the most popular creators on YouTube—76 million followers, 16 billion views—and he’s built that audience by making science genuinely fun and accessible. He’s put out one video a month on YouTube for 15 years, with remarkable consistency.

I asked him how he’s stayed grounded across a career on a platform with its own relentless pressures. Mark said he’s never had a long-term plan. Fifteen years of consistency, and none of it was by design. Instead, he has a clear set of principles that guide him, and he focuses only on the next step in front of him. And then, according to Mark, “good shit’s gonna happen.”

Then Mark introduced me to the scientific concept of emergence, a process that occurs in nature when multiple parts come together to form a complex whole without a clear plan or intention. I had a strange feeling when I heard him talk about how he trusts an emergent philosophy to guide his own career. He was describing something I’d already been doing for years, without ever having a name for it.

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.

Emergence can look like magic

A murmuration of starlings—thousands of birds moving together in those wild, shape-shifting clouds you see in videos—has no choreographer. Each bird follows three simple rules: stay close to your neighbors, don’t collide, and move in the same general direction. That’s it. From those three rules, something breathtaking appears. An outcome no single bird designed or planned.

Same with a beehive. No bee has the blueprint for the colony. Each bee just follows its local rules—tend the larvae, forage for pollen, respond to signals. But the colony as a whole can regulate its own temperature, navigate to food sources miles away, and survive for decades. A single ant isn’t intelligent in any impressive way. Yet an ant colony can find food, build bridges, regulate temperature, wage war, and adapt to changes in its environment. That capability doesn’t exist in any one of them; it only comes together in the colony as a whole.

That’s the strange magic of emergence: the whole becomes capable of things that are completely invisible at the level of the parts. Emergence is what happens when simple, consistent principles—applied locally, over time—produce something complex and beautiful that couldn’t have been predicted or designed in advance.

In an emergent career, you are both the individual bird and the whole murmuration—the one following the rules and the one becoming something those rules couldn’t have predicted. Every decision you make, every person you work with, every risk you take or don’t take—those are your local rules in action. You can’t see the pattern they’re creating from inside it. You can only see the next step. Yet over time, something emerges. A body of work, a reputation. Something that looks, in retrospect, like it was designed, even though no single decision along the way felt like a plan.

My whole career has been example after example of the power of emergence, but I’ll give you the best one, which is also the most recent. I stepped off the traditional career path four years ago with no plan. I simply started saying no to the jobs I was known for—COO roles at bigger and more impressive companies—because they no longer brought me joy. It was scary, and it felt necessary. I explored a bunch of different paths and worked hard to learn to listen to the parts of myself other than my ego. It was hard. I felt exhausted and confused a lot, particularly when someone offered me some new fancy job I knew I’d be great at. My ego really, really wanted to say yes. I kept saying no.

I built the leadership communities Glue Club and The Guild. I wrote on LinkedIn and Substack. Not because I had a vision for what any of this could become or because any of it made sense to anyone else, but because they made me happy every day. I was learning, working with people I loved, and having the kind of impact that mattered to me. All of it brought me energy, and I was committed to focusing on that compass. That said, more than any other time in my career, I felt like I was walking through a dark tunnel, with no sense of where I was going. Every magical moment in my career has been entangled with periods of confusion, discomfort, and darkness.

Then TED asked me to give a talk, and I said yes because I was excited about what I would learn and how I could connect with people through the talk. It felt a little random at the time but turned out to matter more than I expected. Someone on my team said, “I think this might be the beginning of something.” I said, “I just want the talk to be good.”

A year after my talk came out, TED came back and asked me to take over WorkLife, the podcast that TED and Adam Grant had spent seven years building. When they made that offer, it was like someone had turned the lights on in the tunnel. They saw me in a way that I could not see myself. That offer transformed my weird, disconnected pile of projects into a whole that felt like magic.

When I’ve talked to successful people about their own career path, almost all of them have a story that sounds like emergence.

As an example, I asked my friend Claire Hughes Johnson, the former COO of Stripe, about how she’s made career decisions and how she thinks about her life’s work. On paper, Claire’s path—politics, to senior operations and product leadership at Google, to COO of Stripe—looks very methodical and designed. But in conversation, she makes it clear that she never had a plan and was just focused on the right next step:

“Am I learning? Am I motivated? Am I in the right job? Is this the right impact? Is this what I want to be doing? . . . I think some people look [at my career] and they’re like, oh, you charted this course of success.

No, I was kind of unsatisfied, and just kept trying to find the thing . . . I don’t feel like I will figure out what my life’s work is. It will end up being the work that I did.”

It’s pretty weird to hear someone as successful as Claire say, even at this point in her career, that she doesn’t know what her life’s work is. But it honestly made me feel less crazy. As Claire explains it, she has two principles—she wants to learn and have a significant impact—and focuses on making the best next decision based on those.

To embrace emergence in your career, you have to do exactly what Claire does. You have to push past the traditional questions “How do I get where I want to go?” or “What is my life’s work?” and focus instead on asking, “What’s the right next step for someone with my principles, my energy, my values?”

That can be a harder question: Knowing your principles requires knowing yourself. Taking the next step in line with them often requires risk. You must tolerate uncertainty and real discomfort. You have to bet on yourself and have faith that the path will reveal itself.

After reflecting on my own experiences and hearing so many stories from brilliant successful people through WorkLife, I’ve come to believe that the two keys to an emergent career are defining (and redefining) your own local rules to help you make the next best decision, and following a few universal principles that increase the likelihood of career magic.

And then releasing control and having faith that those two frameworks will lead you to where you’re supposed to be.

Establish your own local rules for work

Developing your local rules that guide how you make decisions requires listening to yourself and the data you collect over the days, months, and years of work. The ongoing challenge of an emergent career is honing and evolving those rules over time and experience.

I didn’t go looking to prove this theory. I stumbled on it by asking successful people how they made decisions. When they answered, they all offered up their own principles as guiding forces.

Rules help you take the right next step

Mark Rober’s local rules are: focus on content that teaches, not just entertains; quality over quantity always; and sustainability over everything. He talked about how each of these have helped him decide when to grow his company and when to ignore the YouTube algorithm’s demand for daily posts.

Claire Hughes Johnson told me her compass has always been two words: learning and impact. If a decision gives her both, she moves toward it. If it doesn’t, she doesn’t.

One of my greatest mentors, Patty Stonesifer—an early executive at Microsoft, the first CEO of the Gates Foundation, and one of the first independent board members of Amazon—described four principles that she articulates in a mission statement: love and be loved, seek justice, learn, and laugh. She uses them to evaluate how she spends her time (she literally has a monthly worksheet she prints out to plan and evaluate her time against her principles).

Adam Grant, the organizational psychologist, has three. He talked about the principles that guide how he chooses which book to write next on WorkLife, but in a follow-up email, he crystallized his career decision principles down to: interest (“Will I wake up in the morning excited about it?”), importance (“Does it align with my values?”), and impact (“Can I make a unique contribution?”).

While writing this post, I asked Lenny what his are, and he said: follow my energy, keep the quality bar high, and be useful.

Mine, for the early part of my career, were three things: learning, people, and mission. I thought of it as a three-legged stool.

Learning, for me, didn’t mean a little learning—it meant a curve so steep I was terrified. I get energy from being in over my head. People meant I needed to be surrounded by people I was excited to learn from. And mission meant I needed to feel like the problem I was working on actually mattered and that I personally wanted to devote my time and energy to solving it. Not every important problem is the right one for me.

The point of these rules is to guide your personal decision-making. When presented with two choices, how do you decide what the right next step is? How do you explain why something that might feel so right to someone else feels wrong for you?

When Bret Taylor asked me to join him at Quip and help figure out the business, I ran it through my principles almost instinctively. Learning? Terrifying amounts of it—I’d never built a SaaS business, never done sales or marketing before. People? Bret is someone I was excited to keep learning from, and I knew he’d assemble an extraordinary team. Mission? Well, productivity software for teams didn’t feel especially meaningful to me—my stool had one wobbly leg—but I felt that the other two were so strong that it didn’t matter. I went in with my eyes open about why I was there and placed a bet based on my principles.

Your rules will evolve

My local rules have changed over time—what I needed from work at 30 was different from what I needed at 40—and almost everyone’s do. Sometimes career decisions help you discover a rule (or a nuance of a rule) that you didn’t know was so important to you. That happened to Patty Stonesifer in the middle of her career. After leaving a senior executive role at Microsoft, she accepted a senior position at DreamWorks because it sounded cool. But about three months in, Bill and Melinda Gates approached her with the opportunity to help create and build the Gates Foundation, and she realized that at DreamWorks she was missing some pieces that were really important to her. That gut check led her to create her mission statement and articulate her “seek justice” pillar.

In that WorkLife conversation, she also shared that her enthusiasm for learning, one of her principles, can overpower everything and, like my wobbly stool legs, she’s had to think about ensuring that there is the right balance across the different principles to not let one of them guide all the decisions.

For me, the only principle that hasn’t changed at all is learning. I still need to be terrified or I’m bored. But I’ve gotten much more clear on the impact that matters to me, and the people leg of my principles has gotten more specific—I need people I look forward to working with every day, people who see me clearly, and people I can clearly unlock. I’ve added some new rules too, like “seek joy,” which wasn’t a priority for me earlier in my career. These days, loving my hours and days is one of the main ways I measure my overall career satisfaction.

How do you figure out your local rules?

The most powerful signal I’ve found for defining your own local rules is your energy. Not your ambitions, not what looks good on paper, not what your parents think—what work energizes you. The question to ask is “What actually lights me up today?” not “What should I want?”

There are a bunch of exercises out there that can help you do this. Here are two that have been really useful to me:

1. Spend a week scoring your energy after every part of your day. For many of us, this can be broken down into 30- or 60-minute segments like meetings or work blocks. At the end of the day, sit down and score each 30-minute block on a scale from 1 to 10. My coach, Maggie Hensle, had me do this when I was at a lost moment in one job, and it came back all 1s and 10s. My day was filled with an almost equal amount of work that lit me up and work that made me want to bash my head against the wall. But most importantly, when I really dissected the 10s, I realized that the best work for me was coaching, mentoring, sponsoring, and connecting with people. It was an important insight that indirectly led me to the community work that I do now.

2. Identify your peak moments. Whenever I am trying to understand the work that lights people up, I ask them a series of questions: “Looking back over the past three to five years, what are three key moments when you felt like you were at your best? What are the work moments you are proudest of over those years? When you think about activities where the time flew by or you felt like you could have kept going forever, what were they?” Questions like these help you describe the type of work that excites you and brings out the best in you. The ideal way to do this exercise is with a coach or a best friend—someone who is rooting for you and will hear the patterns when you describe your answers. That person can share back with you some of the words or themes that come up over and over again.

Whatever exercise you choose, you are looking for patterns. Those patterns are your local rules in disguise.

Increase your surface area for magic

Knowing your local rules tells you how to decide on your best next step. But the truth is that there are also universal principles that increase the odds of magic. These behaviors and actions are not a plan. Instead, they’re creating the conditions for “good shit” to happen (to borrow Mark Rober’s words). And without them, you’re probably leaving a lot of magic on the table.

1. Be the person everyone wants to work with again

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ChatGPT Codex Voice + browser + Sites: an expert’s AI workflow | Nick Baumann (OpenAI)

Brought to you by:

• Bolt.new—Turn your idea into a real product

• Hyperagent—Deploy fleets of agents that handle real work

Nick Baumann from OpenAI joins Claire to demonstrate how he uses ChatGPT, Codex, and Voice to automate huge parts of his work and life. He walks through advanced workflows for managing tasks in parallel, monitoring email and expenses, booking travel, building and publishing websites, and even turning dozens of raw clips into finished videos.

Biggest takeaways:

1. ChatGPT Codex Voice doesn’t just answer questions. It can actually operate your computer while you keep talking. Nick Baumann demos the new interface live: he triggers it with a hotkey, the orb reads what’s on his screen through Appshots, and Codex spins up separate threads to book a flight, file an expense report, and check his calendar at the same time.

2. One of Codex’s most powerful features is also one of its least understood: thread-forking. When a task gets complicated, Codex can open a new thread, branch from an existing one, or pull context from previous conversations on its own. Users don’t have to manually organize everything first.

3. Heartbeats in ChatGPT Work offer a practical glimpse of always-on agents. Nick gets notified when a suspicious charge appears, a package is nearby, or an email needs his attention—and he set it all up without writing code.

4. ChatGPT Sites looks much closer to a real deployment platform than a lightweight demo. It includes a SQL database, file storage, environment variables, and email-based access controls. During the episode, Claire and Nick build and publish a live How I AI tips site, organized by tool and job function, in roughly the time it would normally take to set up a CMS template. For internal tools, small apps, and private resources, that starts to feel genuinely useful.

5. Nick’s video-editing workflow is one of the clearest examples of AI cutting real production work. He records 50 or 60 raw clips, uploads them, talks through the rough story he wants, and lets a custom plugin transcribe everything, scan the footage, choose the strongest takes, and assemble finished vertical videos overnight. What would normally eat up most of a content team’s day is largely handled while he sleeps.

6. Voice may be the best way to give AI context because it removes the pressure of figuring out exactly what to type. Claire calls this the “yapper’s API,” and the idea is simple: people often get more useful results when they talk freely than when they stare at an empty prompt box trying to be precise. Across two-person voice chat, mobile dictation, and Codex’s orb interface, the same pattern keeps showing up—people who talk to AI tend to give it more context, and more context usually leads to better work.

7. As AI gets more capable, latency is becoming a much bigger product decision. Nick often uses the highest-intelligence mode in Voice, but once a model has the tools it needs, speed can matter more than another small jump in reasoning quality. A lot of AI products are still designed around the assumption that waiting is unavoidable. As that changes, the tools that feel immediate will have a major advantage—especially for users who currently find AI too slow to bring into a live workflow.

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.

Nick Baumann is on the Developer Experience team at OpenAI, where he spends his days building with, testing, and communicating the capabilities of ChatGPT Codex and ChatGPT Work. In this episode, Nick walks me through several features that have launched or evolved recently: the new voice interface with its screen-reading orb, the Heartbeats automation system in ChatGPT Work on mobile, the live ChatGPT Sites deployment feature, and his personal use case for AI-assisted UGC video editing.

What you’ll learn:

1. How two-person voice chat works

2. How Heartbeats work

3. How to build and deploy a live website with ChatGPT Sites

4. How to delegate a flight search, hotel booking, and expense report to Codex in a single voice conversation without opening a single app manually

5. Why ChatGPT Work on mobile is the most underutilized AI workflow for people already using the ChatGPT app

6. How to use a custom UGC Video plugin to feed 50 raw clips into ChatGPT, let it pull transcripts, pick the best takes, and assemble a finished vertical video overnight

Brought to you by:

Bolt.new—Turn your idea into a real product

Hyperagent—Deploy fleets of agents that handle real work

In this episode, we cover:

(00:00) Introduction to Nick Baumann

(02:56) What’s new in Codex

(05:40) ChatGPT Work and Heartbeats

(06:40) Live Codex voice demo

(13:25) Latency vs. intelligence

(14:36) Quick recap

(15:04) Voice on mobile and the ChatGPT Sites workflow

(21:24) Live UGC video demo

(32:30) How I AI website results

(34:04) Lightning round and final thoughts

Tools referenced:

• ChatGPT Codex: https://chatgpt.com/codex

• ChatGPT Sites: https://chatgpt.site

Where to find Nick Baumann:

LinkedIn: linkedin.com/in/nick--baumann

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 jordan@penname.co.