The Lenny Rachitsky Playbook : Prompts, Growth Frameworks, and Strategies - Part 1 of 2
Lenny Rachitsky built a growth engine with 1Mn subscribers. In this deep dive, I break down how you can use frameworks, growth loops, funnels and impactful strategies that Lenny implemented
I didn’t plan to write a case study on Lenny.
It just… happened.
I was trying to figure out why solo creators were building more momentum than most VC-backed startups. That’s when I opened Lenny’s newsletter again.
One post. Then five. Then the archives.
And two pieces hooked me hard:
How the Biggest Consumer Apps Got Their First 1,000 Users — broke down early-stage growth better than most books.
The Best of Lenny’s Newsletter 2021
Then I found this deep dive on Lenny over at Growth In Reverse:
At that point, I decided to write a detailed newsletter on “Lenny’s Systems and Strategies”.
Why?
Because Lenny’s not just a creator. He’s a one-man SaaS company — with better retention than most B2B startups.
He earns trust before selling.
He scales content like a product.
He builds a community that solves for retention.
And here’s the hack:
“ You can Lennify your business — even as a team of 10 (or a small growth team of 2) — using AI. “
→ AI can write.
→ AI can summarize.
→ AI can repurpose, distribute, organize, and personalize.
But it needs a system. And Lenny has built one of the best.
This case study breaks down how that system works — and how to replicate it with AI.
If you’re a founder, marketer, or growth leader… You’ll walk away with a smarter way to build and scale trust — at speed.
I’m breaking this playbook into two parts to keep it actionable, dense, and easy to follow.
In Part 1 (This Edition) — You’ll learn:
The user and revenue growth timeline
Key inflection points
Content + Monetization: The Freemium - With Prompts
The Community Flywheel: Why People Stay (and Pay) - With Prompts
Ecosystem flywheel that makes Lenny’s business unstoppable - With Prompts
Use-case Prompts: Lennify your Business
By the end of this edition, you’ll understand how Lenny engineered his growth engine — and what levers you can pull today.
In Part 2 (Next Week) — You’ll get:
The complete Enterprise Lennification Playbook
How large companies can replicate Lenny’s playbook across content, community, and product
Plug-and-play workflows for founders, marketing, product, and customer success teams
Quarterly OKRs and KPIs to measure impact
Real-world use cases and templates
Bonus: How internal teams (Sales, CS, Enablement) can leverage this system to drive GTM
This second part is for teams that want to scale trust like a startup — without losing the depth, voice, or momentum.
The user and revenue growth timeline - Lenny Rachitsky
Lenny didn’t set out to build an empire.
He just wanted to share what 7 years at Airbnb taught him.
That one post on Medium earned $1,700 and something more valuable — attention.
It was the moment of realization that there’s real demand for honest, tactical, behind-the-scenes content on product, growth, and startup life.
From there, he quietly built one of the most successful creator-led businesses in tech.
June 2019: Sharing lessons on Medium. No list. No business. Just essays.
Feb 2020: Switched to Substack. Better control. Direct audience. Still free.
April 2020: Launched paid subscriptions.
13,000 free subscribers
486 paid subscribers
$56,000 in ARR
Dec 2020: Gained serious traction.
45,000 free
3,300 paid
ARR crossed $360,000
2023: Hit 325,000 total subscribers
Revenue? “Significantly more” than his Airbnb salary
2024: Blew past 900,000 subscribers
18,000+ paid subscribers
Revenue crossed $2M per year
2025: 1Mn+ Subscribers
It was the result of clarity, compounding, and a few key plays.
What Founders and Growth Leaders should just adopt from Lenny Rachitsky
This isn’t just a case study. It’s a growth playbook.
If you’re building anything — a startup, a brand, or a revenue line — adopt these 3 lessons:
1. Give before you ask.
Lenny wrote for free for 9 months before charging a rupee.
2. Design for compounding.
A community, a referral loop, a podcast — each asset made the next easier.
3. Monetize the momentum.
He didn’t rush it. But when the time came, he stacked value: pricing tiers, perks, even bundles (free Notion + Superhuman access) to drive upgrades.
The Inflection Points That Turned a Newsletter Into an Empire
Most newsletters slow down at 1,000 subscribers. Lenny didn’t just grow, but compounded.
1. The Substack Switch – Feb 2020
He left Medium for one reason: control.
On Medium, he had eyeballs. On Substack, he got emails.
Emails → relationships → revenue.
But there was more: Substack was quietly building tools that would soon fuel massive organic growth — like the now-famous Recommendations engine.
Founders: Own your audience. Always. Platforms come and go. Permission from subscribers will always be there (email subscriptions to newsletter in this case).
2. Going Paid – April 2020
COVID hit. Uncertain Times. Lenny made a bold bet:
He launched paid subscriptions at $15/month.
What happened?
486 people converted in 30 days.
He validated price and value instantly.
ARR: $56,000 from zero.
That was proof enough to go all in.
What worked:
He gave 9 months of free value first.
He didn’t just sell content. He sold outcomes (insight, clarity, community).
3. Community Is the Moat – Sept 2020
Anyone can copy content. But not a 20,000-member Slack group full of product leaders helping each other.
This community became the reason to stay subscribed.
Lenny barely had to moderate — it grew on its own.
Growth leaders: Don’t build a list. Build a room people want to stay in.
4. Substack Recommendations – 2022’s Growth Rocket
Substack flipped a switch. Literally.
Newsletters could now “recommend” others.
Lenny had built goodwill with hundreds of other creators.
When the feature launched, he was one of the most recommended writers.
What followed? A Hockey stick curve.
80%+ of new subs came from this engine.
By 2023, he hit 325K subs.
By 2024, 900K.
By 2025, 1Mn+
Lesson: Platform arbitrage > paid acquisition — when done early.
5. Launching the Podcast – March 2022
He was nervous. He didn’t think it would work. Then one episode with Harry Stebbings changed everything.
Within 2 years, Lenny’s Podcast hit 10M+ downloads.
It ranked in Spotify + Apple’s top tech charts.
Sponsors lined up. Revenue followed.
Even better? It fed the newsletter.
Every listener was a future subscriber.
Build once, distribute twice. Repurpose multiple times..
The Takeaway: Stack Your Inflection Points
Each move wasn’t just clever — it was compounding:
Substack gave distribution
Paid gave revenue
Community gave retention
Recommendations gave viral reach
Podcast gave new audience + sponsors
Content + Monetization: The Freemium Playbook
Lenny sold clarity, career momentum, and community — all bundled in a weekly email.
And he priced it like a SaaS founder, not a blogger.
Let’s break down what made it work.
The Freemium Funnel That Converts Like Crazy
Most newsletters either stay free forever or hide everything behind a paywall.
Lenny split the difference:
Free plan: 1 post per month + preview of paid posts.
Paid plan: Full weekly posts + Slack access + perks.
It’s classic freemium:
Give just enough value to hook.
Make the full experience irresistible.
Conversion rate? ~5% of total subscribers pay.
Freemium + Monetization Prompts
Build trust → then layer in value → then convert with precision.
Prompt #1 : “What value can I give away for free that builds trust, but leaves room for premium upgrades?”
Prompt:
I’m a serial founder and growth strategist designing a modern, content-led business engine inspired by Lenny Rachitsky — combining audience-first content, community, and smart monetization. I want to create a system where I give away high-trust, high-utility content for free, but leave clear and compelling reasons to upgrade to a paid tier.
Write a comprehensive, actionable guide answering this question:
“What value can I give away for free that builds trust, but leaves room for premium upgrades?”
Include the following:
1. Value Design Frameworks:- Explain how to craft free content that delivers “aha” moments without giving away the entire playbook.- Differentiate between “trust accelerators” (free) and “transformation enablers” (premium).
2. Examples of Freemium Models:- Analyze proven creator-led or SaaS-inspired freemium strategies (e.g. Lenny’s newsletter, Superhuman’s access model, Notion’s templates).- Include at least 3 real-world examples with what they gave away for free and what was gated.
3. AI-Enhanced Trust Building:- Suggest how AI can be used to automate or personalize the free layer (e.g., summarization, recaps, quizzes, smart distribution).- How to use AI workflows to scale trust while keeping a human feel.
4. Premium Upgrade Triggers:- What to offer in the paid tier: exclusive content, community, toolkits, 1:1 support, live sessions, etc.- How to signal premium value without creating “FOMO fatigue.”
5. Conversion Psychology:- How to engineer desire for the upgrade: perceived exclusivity, career upside, speed of outcomes, or belonging.- Examples of how to phrase upgrade CTAs to emphasize outcome, not access.
6. Bonus: Offer a 3-tier freemium design template:- Tier 1: Free (trust builder)- Tier 2: Paid (transformation layer)- Tier 3: Premium or team plan (scale/career unlock)
Use language that respects the intelligence of the audience (founders, Product Managers, marketers), and give examples where possible. Every suggestion should tie back to creating momentum, compounding trust, and sustainable business leverage.Prompt #2 : “What 3 subscription tiers can I offer that increase perceived value — not just access?”
Prompt:
Act like a monetization strategist and audience-first product builder for creator-led businesses. I want to design 3 subscription tiers that go beyond “paywalling content” and instead increase perceived value, unlock outcomes, and create a sense of career or business acceleration.
Give me a breakdown of 3 smart subscription tiers I could offer — modeled after Lenny’s playbook — where:
- Tier 1 (Free) builds trust and delivers real utility- Tier 2 (Paid) feels like a professional edge or growth unlock- Tier 3 (Premium/Team) adds network, speed, and status to the experience
For each tier, describe:
1. The core value (what they get and why it matters)
2. What’s included (features, access, perks)
3. The perception driver (what makes it feel worth it)
4. Ideal price range
5. Example language or CTA to position it.
Focus on founders, product leaders, and high-agency builders as the target audience.
Bonus: suggest 1-2 bundled perks or services that make Tier 2 and 3 feel 5–10x more valuable than Tier 1.Prompt #3 : “How can I bundle tools, perks, or discounts to make an annual plan a no-brainer?”
Prompt:
Act as a growth strategist and monetization expert for audience-led businesses. I’m designing an annual plan that goes beyond content — I want it to feel like a steal because of the bundled perks.
Answer this: “How can I bundle tools, perks, or discounts to make an annual plan a no-brainer?”
Include:
1. Types of perks that create perceived and actual ROI — e.g., software credits, private group access, expert templates, AMAs, courses, 1:1 consults.
2. How to find bundle partners — tools, services, or brands my audience already loves (e.g., Notion, Superhuman, Loom, Figma).
3. Bundling strategies — e.g., “The Greatest Bundle Ever” playbook, limited-time perks, rotating partners, or community-curated perks.
4. Psychology of annual conversion — why bundles work, how to frame them, and how to make yearly pricing feel like an upgrade, not a lock-in.
5. Optional: Suggest 3 bundle ideas that align with my audience: founders, builders, product/growth leads.Use the tone and structure of Lenny’s playbook — high signal, tactical, actionable.Prompt #4 : “What can I sell that doesn’t just offer more content, but offers more outcome?”
Prompt:
Act like a productized expert strategist and transformation-focused monetization advisor. My goal is to sell offerings that don’t just unlock more content — they unlock better outcomes. I want people to feel like my paid product helps them do something faster, better, or more confidently — not just read more stuff.
Answer this: “What can I sell that doesn’t just offer more content, but offers more outcome?”
Include:
1. High-leverage outcome-based products — e.g., templates, decision frameworks, live working sessions, async feedback, career accelerators, or curated introductions.
2. Examples of content → outcome upgrades (e.g., blog post → checklist → tool → workshop → result)
3. Types of value delivery that scale outcomes:- Toolkits (Notion, Airtable, GPT prompts)- Community-solved problems (Slack, Discord, masterminds)- Personalization (1:1 reviews, audits, teardown libraries)- AI-enhanced accelerators (custom GPTs, automation flows)
4. How to structure these offers so they feel like momentum, not more homework.
5. Bonus: suggest 3 “outcome products” I could launch next quarter that align with founders, product/growth leaders, and solo builders as my audience.Prompt #5 : “Which pricing model fits my audience: monthly, annual, cohort-based, or value-tiered?”
Prompt:
Act as a monetization strategist for a high-trust, content-driven business serving founders, growth leaders, and solo builders. I’m building a system where content builds trust, community builds retention, and monetization is a lagging indicator of value.
Answer this: “Which pricing model fits my audience best — monthly, annual, cohort-based, or value-tiered?”
For each model, include:
1. How it fits (or doesn’t) with my audience’s psychology, budget cycles, and behavior.
2. Tradeoffs — conversion vs. retention, cash flow vs. LTV, friction vs. loyalty.
3. When to use each:- Monthly = low-friction entry, flexible- Annual = retention lock-in, bundle sweeteners- Cohort-based = scarcity, accountability, high-touch- Value-tiered = aspirational upgrades, team plans
4. Case studies or examples from creators or SaaS founders doing this well.
5. Bonus: Suggest a hybrid model (e.g. freemium monthly → cohort unlock → team tier) designed for an audience of product thinkers.Pricing That Signals Premium
Lenny didn’t underprice.
$15/month or $150/year
A higher “I Can Expense It” tier at $300/year
Group plans for teams
No $5 newsletter here. He knew his content saved PMs and founders time, confusion, and costly mistakes.
That’s high-ROI. And he priced accordingly.
Stacking Value with Perks
In 2023, Lenny launched “The Greatest Bundle Ever”
Free access to Notion, Superhuman, Linear, and more — worth $500+
Only available with annual plans
That bundle turned paid subscriptions into a no-brainer.
And it worked. Huge spike in upgrades. And more stickiness.
Content Strategy: Teach What People Pay to Know
What makes his posts binge-worthy?
Clear, step-by-step guides.
Real-life examples from companies like Airbnb, Figma, and Duolingo.
Topics people search for when they’re stuck:
How to improve retention.
How to hire a PM.
How to run weekly growth meetings.
Every post compounds trust.
Content Strategy Prompts
Write content that compounds trust and attracts the right audience.
Prompt #1: “What are 10 painful, high-stakes questions my ideal customer is Googling right now?”
Prompt:
Act as a content strategist and growth advisor for a founder-led media business that targets high-agency audiences (founders, product/growth leaders, and solo builders).
Answer this: “What are 10 painful, high-stakes questions my ideal customer is Googling right now?”
Include:
1. The exact phrasing they’re likely to search for (Google-style, not clever headlines)
2. The pain behind the question — what they’re struggling with or afraid of.
3. The intent — are they looking to fix something, decide something, or gain confidence?
4. Prioritize questions where an actionable post, playbook, or teardown would earn massive trust fast
Bonus: suggest one content format per question — e.g., newsletter post, teardown, checklist, AI prompt pack, Notion doc, or video walk-throughPrompt #2: “Which parts of my job or founder journey would my younger self pay to learn faster?”
Prompt:
Act as a strategic content coach for a seasoned founder who wants to turn lived experience into high-impact, evergreen content for other ambitious builders (founders, PMs, solo creators, operators).
Answer this: “Which parts of my job or founder journey would my younger self pay to learn faster?”
Include:
1. Specific moments of pain, confusion, or wasted time (e.g., hiring the wrong person, pricing too low, shipping the wrong thing).
2. Lessons learned the hard way — but now explainable in a playbook, checklist, or teardown.
3. Which of these lessons map to career unlocks or confidence builders for your audience.
4. Rank by urgency + value — “Would I pay $100 to learn this a year earlier?”
Bonus: suggest how to package these insights:
Evergreen blog post or newsletter
5-email onboarding series
Notion system
Founder AMA
AI prompt library
Keep the tone practical, humble, and story-driven — real scars, real takeaways.Prompt #3: “List my top 5 wins, failures, or systems — that could be turned into evergreen content.”
Prompt:
Act as a strategic editor and content repurposing expert for a founder-led business targeting builders, product leaders, and early-stage operators. I want to identify the 5 most powerful pieces of my experience — and turn them into evergreen, high-impact content assets.
Answer this: “What are my top 5 wins, failures, or systems that could be turned into evergreen content?”
For each one, include:
1. The core lesson (what happened and what I learned)
2. Why this would resonate with my audience (pain, aspiration, relevance)
3. What format would work best (e.g. teardown, checklist, story thread, prompt pack, playbook, Notion doc, podcast episode)
4. A working title/headline for each — something clear, tactical, and curiosity-inducing
Bonus: how each piece could be reused across channels (e.g. LinkedIn → newsletter → podcast → community AMA)
Use the tone and clarity of Lenny’s posts — dense with value, light on fluff.Prompt #4: “What is one playbook or checklist I use that people ask me about often?”
Prompt:
Act as a systems-thinking content strategist for a seasoned founder. I want to turn my most-requested playbook or checklist into a trust-building, evergreen content asset that signals value and authority — and potentially anchors a paid offer.
Answer this: “What is one playbook or checklist I use that people ask me about often?”
Include:
1. Identify what system, template, or process I use that sparks repeat questions from peers, clients, or followers (e.g., launch process, pricing calculator, cold outreach script, async hiring doc, GPT prompt kit).
2. Why this system matters — what problem it solves and who benefits most.
3. How to turn it into a usable, skimmable asset (Notion doc, Google Sheet, Airtable base, AI prompt pack, 1-pager PDF).
4. A compelling title — something outcome-driven, curiosity-piquing, and credibility-rich.
Bonus: suggest how to ladder this asset into a larger offer — e.g., freebie → mini-course → paid community → annual subscription.Prompt #5: “Summarize everything I know about [X topic] in a way that a junior teammate can understand and apply.”
Prompt:
Act as a founder-educator who’s training the next generation of builders. I want to summarize deep, nuanced knowledge about a specific topic — not just to explain it, but to make it instantly applicable by a junior teammate, intern, or new hire.
Answer this: “Summarize everything I know about [X topic] in a way that a junior teammate can understand and apply.”
Use the following structure:
1. Topic overview — in 2-3 clear sentences, what it is and why it matters
2. Foundational principles — 3–5 rules, truths, or frameworks to understand it
3. Step-by-step process — how to apply it in real life, start to finish
4. Common mistakes — what junior folks often get wrong, and how to avoid them
5. Pro tips or shortcuts — what you learned the hard way
Optional: include 1 template, checklist, or Notion doc idea that could turn this into an evergreen training or onboarding asset
Use simple language but don’t oversimplify. Assume the reader is smart but new.Storytelling + Trust Building Prompts
Because no one shares “tips” — they share transformations.
“What’s a moment I failed, learned, and bounced back — that others in my niche can relate to?”“Which of my customers has a story others would want to hear — and how can I tell it with permission?”“What are the invisible scripts my audience believes… and how can I flip them?”“What’s a contrarian truth I believe in my domain, and how did I learn it?”“If I had to turn my journey into a story — what would the hook, challenge, climax, and lesson be?”Distribution: Built Once, Shared Everywhere
He didn’t just rely on email opens.
He built a content engine that pushed every post across:
X (Twitter)
LinkedIn
Substack’s network
Podcast mentions
Word-of-mouth in the Slack group
Each channel drove new eyeballs back to the funnel.
Distribution + Ecosystem Flywheel Prompts
Build a machine, not a moment.
Prompt #1: “What is the one channel I already own — and how can I repurpose everything through it?”
Prompt:
As a founder, marketer, or growth leader who owns at least one direct distribution channel (like an email list, newsletter, podcast, or community), I want to build a high-leverage repurposing engine using AI and systems thinking.
Act as a strategist who understands compounding growth, content ecosystems, and creator-led business models (like Lenny’s).
Help me identify:
1. The single most strategic channel I already own — one where I control access, communication, and engagement (not subject to algorithm shifts).
2. How to reverse-engineer a repurposing flywheel from that channel — turning each core piece of content into 5+ native assets (for LinkedIn, X, short video, podcast snippets, cold DMs, community posts, etc.).
3. The AI workflows, tools, or frameworks I can use to automate this process without burning out.
4. A weekly content loop where the primary channel feeds distribution, lead gen, and conversion — with clear roles for each channel in the ecosystem.
5. A 3-month plan to test, measure, and refine this strategy using real engagement signals.
Bonus: Tie it all together with 1-2 examples from top creators or SaaS founders who turned a single owned channel into a repurposing machine.Prompt #2: “If I launch a podcast, newsletter, job board, or course — how will it feed my existing audience flywheel?”
Prompt:
As a founder, creator, or growth leader who already owns attention through a core asset (like an email list, newsletter, LinkedIn audience, or private community), I want to strategically launch new products — like a podcast, course, job board, or newsletter — in a way that strengthens my overall flywheel rather than creating silos.
Act as a strategist who deeply understands audience compounding, content ecosystems, and the business models behind modern creator-led SaaS or media companies.
Help me:
1. Map my current audience flywheel — including where I currently capture attention, build trust, and monetize.
2. Evaluate each new launch (podcast, job board, course, newsletter) not just as a standalone product, but as a force multiplier — how will it:
- Drive traffic to my owned channels
- Deepen retention or engagement
- Generate UGC, referrals, or partnerships
- Unlock new monetization paths
3. Design a content + distribution loop where each new asset feeds the existing ecosystem (e.g., newsletter → podcast → course → community → job board).
4. Anticipate friction points — what will get harder as I layer on more formats (e.g., bandwidth, quality control, content repurposing) and how to mitigate them using AI workflows or delegation.
5. Give me two examples of top-tier founders or creators who successfully launched one of these layers into an existing audience and compounded their momentum — break down what made it work.Lesson for Founders: Your Content Is a Product
Here’s the magic combo Lenny nailed:
Clear audience (PMs, growth leads, founders)
Consistent value (every Tuesday. No fluff.)
Compounding trust (over years, not weeks)
Smart monetization (freemium + perks + premium tiers)
That’s a framework any founder can steal:
> Content = your top-of-funnel.
Community = your moat.
Monetization = a lagging indicator of trust.
The Community Flywheel: Why People Stay (and Pay)
Content gets people in. Community keeps them coming back.
Lenny didn’t just build a Slack group.
He built a movement of product thinkers helping each other win.
Let’s break down how the community became his stickiest growth loop.
Slack Isn’t the Product. But It Feels Like It. (Product Management Folks were Fans)
In September 2020, Lenny quietly launched a Slack space for paid subscribers.
Today It’s 20,000+ members strong.
And it’s not noise. It’s:
1. Mentorship circles.
2. Job leads.
3. Feedback on resumes.
4. Tactical PM discussions.
5. Real-life meetups (nearly 200 in one year!).
For many, this Slack is the product.
Why It Works (And Most Don’t)
Most communities flop. Here’s why Lenny’s thrives:
It’s invite-only. You pay, you get in. That filters out the noise.
It’s role-aligned. PMs, growth folks, and founders speak the same language.
It’s lightly curated. Lenny set the tone, then let the members lead.
It’s integrated into the experience. It’s not a bonus. It’s a core feature of the paid plan.
This turns the Slack from a chatroom… into a daily-use tool for ambitious people.
Community = Retention Engine
When people stick around for the Slack — not just the newsletter — churn drops.
Even if they don’t open every email, they stay for the conversations, support, and identity.
And when your paying customers build relationships inside your product… they don’t leave.
Spillover Effects: The Side Quests That Scale
The community didn’t stop at chat.
It became the base for other business units:
Talent Collective: Recruiters pay to hire from Lenny’s Slack.
Job board: PMs post jobs. PMs get hired.
Summit events: Real-life meetups → full-blown conference in 2024.
The Slack group is now a source of revenue, retention, referrals, and product ideas.
Community Design Prompts
Design for belonging, retention, and internal virality.
“What would a daily-use community look like for my best customers?”“What incentives or rituals can I add to make members want to help each other?”“What onboarding message, pinned post, or welcome ritual can make someone feel like they’ve joined the right room?”“How do I filter in the right people and filter out the noise — without hurting growth?”“What unique value will members get from this community that they can’t get from Google or ChatGPT?”Ecosystem flywheel that makes Lenny’s business unstoppable - Frameworks and Growth Loops
Lenny didn’t build a newsletter. He built an engine.
Each piece of his business isn’t just a revenue stream — it’s a growth loop that powers the others.
Let’s map it out.
Step 1: Newsletter → Trust + Audience
Weekly tactical posts.
Read by PMs, founders, VCs, and operators.
Shared across LinkedIn, X, and internal Slack channels at top tech companies.
This is the top-of-funnel.
It builds reach, trust, and thought leadership.
Step 2: Newsletter → Paid Subscribers → Slack
A portion of readers upgrade.
They want:
More content
Access to the Slack
Perks (like tool discounts and bundles)
Now they’re not just readers — they’re members.
Step 3: Slack → Engagement + Retention
Daily activity.
Mastermind groups.
Peer support.
Real-time help.
This builds retention.
People stick because their identity is now tied to the community.
Step 4: Slack → Podcast + UGC Fuel
Members share ideas, frameworks, success stories.
Some become podcast guests.
Some get hired, promoted, funded — and post about it.
Now Lenny has unlimited user-generated content, plus credibility boosts from community wins.
Step 5: Podcast → New Reach → Newsletter
Every episode plugs the newsletter.
Guests promote it to their own audiences.
New listeners become subscribers.
It’s a self-refilling funnel.
Step 6: Ecosystem → New Offers (Uncover Jobs, Courses, Events)
Now that he has:
An audience (newsletter)
A community (Slack)
A voice (podcast)
He can launch anything:
A job board (Lenny’s Jobs)
A hiring collective (recruit top PMs)
A live summit (sold out in 2024)
And every new product gets its first 10,000 users… from the flywheel.
If you're building a business, steal this for your growth loops:
> Don’t build one channel.
Build a system where every action creates momentum.
Lenny didn’t rush. He layered.
Each layer strengthened the next:
Content → Community
Community → Retention
Retention → Revenue
Revenue → Freedom to explore
Use-case Prompts: Lennify your Startup for Founder-led Growth
Here’s a list of exact use cases Lenny has executed in his growth journey — each paired with a ready-to-use prompt founders and growth leaders can apply in their own playbook.
1. Use Case: Building a Newsletter That Sells Trust
What Lenny Did:
Turned personal lessons from Airbnb into tactical, weekly advice for PMs and founders.
Started free. Built trust. Monetized later.
“Write a weekly email sharing 1 actionable, personal lesson from my founder journey that would’ve saved my past self 6 months of trial and error.”
Prompt:
As a founder who writes high-signal, trust-building newsletters rooted in personal experience, I want to identify and repurpose my most valuable content to 10x its reach across LinkedIn, X, and Slack — without burning out or diluting the message.
Act as a growth strategist and content ops expert who deeply understands platform-native behavior, content flywheels, and strategic repurposing.
Help me:
1. Audit my existing content library (newsletters, blog posts, threads) to identify the top-performing pieces — based on metrics (opens, replies, shares) or qualitative signals (DMs, saved posts, screenshots, comments).
2. Match each piece to its ideal repurposing format based on the platform’s strengths:
- LinkedIn = long-form reflections, personal frameworks, story-driven slides
- X (Twitter) = threads, bold takes, 1-line quotables
- Slack (or community) = bite-sized tips, conversation starters, micro-cases
3. Reframe and rewrite the hook or CTA of each post for its destination platform — while maintaining the core insight
4. Recommend a lightweight workflow (or AI stack) to systematize this — including tools for summarizing, clipping, formatting, and scheduling
5. Build a weekly content loop where every newsletter feeds 3-5 touchpoints across other platforms — and each one leads back to the core asset (email list, lead magnet, Slack, or product page)
Bonus: Suggest a naming system or tagging strategy so I can easily resurface, rotate, and remix evergreen content every 90 days2. Use Case: High-Converting Freemium Model
What Lenny Did:
Offered 1 post/month free + paywalled the rest.
Used pricing ($150/year) to signal value.
Added perks and a Slack community.
“Design a freemium content model where the free tier builds trust and the paid tier feels like a career unlock for my audience.”
Prompt:
As a founder, creator, or subject-matter expert building a content-driven business, I want to design a freemium model that builds deep trust at the free tier — and delivers career-transforming value at the paid tier.
Act as a strategist who understands freemium SaaS, content monetization, pricing psychology, and audience-first product design (inspired by playbooks like Lenny’s Newsletter).
Help me:
1. Design a freemium architecture for my content — clearly outlining what belongs in the free tier (to build trust and reach), and what goes in the paid tier (to drive upgrades).
2. Define the transformation the paid tier should deliver — what career unlock, system, or outcome will make it a “no-brainer”?
3. Suggest 3 tiered pricing options that reflect increasing value (monthly, annual, team plan, or an “expense-it” premium tier).
4. Recommend bundled perks or bonuses (e.g. Slack access, templates, discounts, Notion docs, 1:1 consults) that boost perceived value and retention.
5. Build a lightweight upgrade funnel — from first free interaction → value drip → conversion triggers
Bonus: Include 1 example of a real-world newsletter, course, or media product that nails this model — and break down why it converts.3. Use Case: Viral Community as a Retention Engine
What Lenny Did:
Created an exclusive Slack group for paid subs.
It became 20,000+ members strong.
Peer value > platform value.
“Design an invite-only community for my best users where the daily conversations, job leads, and peer support make it more valuable than my product.”
Prompt:
As a founder or creator with a high-value audience, I want to build an invite-only community that becomes the most valuable part of my product experience — driving daily engagement, referrals, and retention.
Act as a community strategist who understands how to design social environments that create identity, status, and compounding value (like Lenny’s Slack group or On Deck’s early cohorts).
Help me:
1. Design a community experience that makes members say, “This is more valuable than the product itself” — through daily use, job leads, mentorship, accountability, or high-signal conversations.
2. Recommend access rules and filtering criteria to make the space feel curated, role-aligned, and high-signal (without killing growth).
3. Define the daily, weekly, and monthly rituals that keep members engaged — think recurring prompts, spotlight wins, expert Q&As, and small group formats.
4. Outline the onboarding flow — from welcome message to first post — that immediately creates belonging and participation.
5. Suggest lightweight systems for moderation, seeding valuable discussions, and measuring engagement/retention inside the community.
Bonus: Give 1 example of a community that’s become more valuable than the core product — and break down why it worked.4. Use Case: Leveraging Platform Loops (Substack Recommendations)
What Lenny Did:
Got recommended by 1,000+ newsletters.
80% of growth came from Substack’s own algorithm.
“What platforms already reward quality in my space (like LinkedIn, Medium, Substack)? How can I reverse-engineer getting recommended or algorithmically boosted?”
Prompt:
As a founder, creator, or content strategist, I want to grow by tapping into the built-in recommendation engines of platforms like Substack, LinkedIn, Medium, and X — rather than relying only on paid ads or manual hustle.
Act as a platform growth strategist who understands the engagement signals and algorithmic behaviors of modern distribution platforms — especially how creators like Lenny leveraged Substack Recommendations and social proof loops to 10x visibility.
Help me:
1. Audit the platforms in my space that currently reward quality — whether through recommendations, discoverability, replies, saves, or featured placements (e.g. Substack recs, LinkedIn Trending, Medium curations, X Threads).
2. Break down the exact mechanics of how their algorithms or social signals work — what kind of behavior or formatting gets boosted? What patterns show up in high-performing content?
3. Give me a playbook to reverse-engineer visibility on one core platform:
- Who to collaborate with
- How to format or schedule posts
- What to measure (e.g., comment/save ratio, recs per post, link velocity)
4. Suggest a weekly engagement flywheel I can use to systematically get recommended, reposted, or linked — including mentions, recs, replies, and UGC
5. Recommend tools, habits, and rituals to track my signal strength and spot early signs that the algorithm is working in my favor
Bonus: Give me 1 case study of a solo creator or founder who built momentum by mastering a platform’s growth loop (not via paid ads), and explain what they did differently.Loved this post?
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