ShipSet vs Lenny's Newsletter
The most-read PM newsletter versus a 90-day daily-practice program for AI PMs. Different shapes, often complementary. Here is the honest split.
Read Lenny's for weekly essays, interviews, and the most active general-purpose PM community. Do ShipSet for structured 90-day progress to a portfolio with a working AI feature. They solve different problems and most working AI PMs do both: Lenny's for thinking, ShipSet for shipping.
At a glance
| Dimension | ShipSet | Lenny's |
|---|---|---|
| Format | 90 daily lessons, 15 min each | Weekly essays + community + occasional courses |
| Focus | AI PM specifically, build-first | General PM, thinking-first |
| Output | 10-piece portfolio + working AI feature | Informed thinking, weekly inputs |
| Cost | $79 founding / $99 year / $14.99 month | Free tier; $20/mo or $200/yr for paid |
| Community | Solo by design (no community yet) | Active Slack + Substack community |
| Resume signal | Public certificate + portfolio URL | None directly (makes you smarter) |
| Best for | AI PMs who want to ship evidence | PMs who want to stay current weekly |
Where ShipSet wins
- Structured daily progress, no decision fatigue
- AI PM-specific curriculum (evals, cost models, prompting)
- Portfolio + certificate as the deliverable
- 90-day completion arc with built-in accountability
- 5 lessons free, no card needed
- 7-day money-back on every paid plan
Where Lenny's wins
- Best weekly PM content on the internet
- Active community of working PMs
- Interviews with PM leaders at every stage
- Coverage of PM career, comp, hiring
- General PM (not AI-only) scope
- Free tier gets you 80% of the value
What does Lenny's actually deliver?
Lenny's Newsletter is the most-read PM publication in 2026. The format: 1-2 long essays per week, frequent interviews with PM leaders, occasional deep-dive guides, and a paid community Slack. Topics span product strategy, growth, hiring, career, monetisation, and yes, AI PM coverage.
The paid tier is the full archive plus the community Slack. The community is the best part: working PMs from real companies sharing actual decisions and asking the dumb questions that get buried in Twitter. The discussion quality is unusually high because the community filter is paid subscription.
The Lenny's value is weekly thinking input: stay current on PM craft, see how senior PMs frame problems, and have a place to ask questions of peers.
What does ShipSet actually deliver?
ShipSet is a 90-day daily-practice program for becoming an AI Product Manager. 97 lessons (including 7 always-free PM Primer lessons), 15 minutes a day, structured into Stage 1 (foundations), Stage 2 (eval + cost), Stage 3 (launch + interview). By Day 5 you ship a working AI agent. By Day 90 you have a 10-piece portfolio.
The mentor is Captain — an AI trained on senior PM playbooks that remembers your build across sessions. Captain can critique your draft PRD, scaffold your eval table, or help you think through cost variance. Always available.
The ShipSet value is structured daily output: a portfolio of shipped artifacts, a certificate hiring managers can verify, and a 90-day arc that turns "I want to become an AI PM" into "here is what I shipped, click to verify."
Why most AI PMs do both
The shapes are complementary, not competing. Lenny's gives you the meta-skills: how PMs think, how the industry is shifting, how to negotiate, how to interview. ShipSet gives you the AI-specific craft: how to write an AI PRD, how to build an eval suite, how to model cost, how to ship.
Reading Lenny's without shipping anything means you have informed opinions and no evidence. Shipping ShipSet without broader PM context means you have evidence and tunnel vision on AI specifically. Doing both gives you the artifacts plus the broader judgment to use them.
Reasonable weekly cadence: 30 minutes on Lenny's on Sunday, 15 minutes a day on ShipSet during the week. Total time investment under 3 hours/week. Compound effect over 90 days is substantial.
When to pick each
- · You are a generalist PM, not specifically becoming an AI PM
- · You learn best by reading and discussing, not by building
- · You already have a portfolio and want weekly inputs to stay current
- · Community matters more to you than structured progress
- · You are specifically targeting AI PM roles
- · You want a portfolio with evidence in 90 days
- · You learn best by building structured artifacts daily
- · Budget is tight and you want one product, not a stack
- · You want the AI PM portfolio and the general PM context
- · You can spare ~3 hours/week total
- · You are in interview prep mode and want every edge
ShipSet pricing
- Founding Lifetime · $79 one-time — first 50 members only, lifetime access, never renews.
- Annual · $99/yr — 7-day money-back guarantee.
- Monthly · $14.99/mo — cancel anytime.
- All paid plans include full 90 lessons + portfolio + Day 90 certificate. First 5 main lessons free for everyone, plus a separate always-free PM Primer (7 lessons).
- Indian residents see INR pricing automatically (₹2,499 / ₹3,499 / ₹699 via Razorpay).
Common questions
Day 1 begins in 2 minutes.
Take the 2-minute diagnostic. See your personalised 90-day plan, salary trajectory, and which lesson you start on. Free, no card.
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