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Lenny's Newsletter

Lenny's Newsletter is a venture capital blog and newsletter tracked by SandHill.io for its investment theses, industry analysis and operating insight. This page collects 763 posts published between June 2023 and September 2026. Recent coverage focuses on AI (Horizontal), Developer Tools and Venture Capital & Startups. Lenny's Newsletter publishes roughly 24 posts a month; the best of them appear in the SandHill weekly digest.

763 posts indexed24 in the last 30 daysAI (Horizontal) · Developer Tools · Venture Capital & Startups · Enterprise SoftwareVisit site ↗

Tuesday, 22 September 2026

3 pieces
Opus 5.5 vs. GPT-6 Sol: which model won my blind taste test?
AI (Horizontal) · Developer Tools
I left Claude for months. Opus 5.5 is why I'm back
AI (Horizontal)
Advanced evals: How to find (and fix) hidden AI failures in your product
AI (Horizontal) · Developer Tools

Monday, 21 September 2026

2 pieces
🎙️ How I AI: Meta’s Muse review + How Warp ships 2,000 PRs a month with AI factories
AI (Horizontal) · Developer Tools
How Warp ships 2,000 PRs a month with AI factories | Zach Lloyd (CEO, Warp)
Developer Tools · AI (Horizontal)

Sunday, 20 September 2026

1 piece
90 minutes of unfiltered product advice from Snap and Discord’s product chief | Peter Sellis
Venture Capital & Startups

Saturday, 19 September 2026

1 piece
🧠 Community Wisdom: Finding your first users before the product exists, debriefing your own interviews, what to optimize for in the early years of your career, and more
Venture Capital & Startups

Wednesday, 16 September 2026

1 piece
Muse review: The personal AI agent that gets consumer UX right
AI (Horizontal) · Consumer

Tuesday, 15 September 2026

1 piece
60+ new creative growth ideas
Marketing & Sales Tech · Venture Capital & Startups

Monday, 14 September 2026

2 pieces
🎙️ How I AI: How two SpaceXAI designers use Grok Bot to do their jobs
AI (Horizontal) · Developer Tools
How Grok Bot designers use AI agents to build personal sites and product prototypes | John Bai & Peng Zheng
AI (Horizontal) · Developer Tools

Saturday, 12 September 2026

1 piece
🧠 Community Wisdom: AI basketball coaching, Jira vs. Linear, building a business case for platform teams, favorite AI use cases, and more

Tuesday, 8 September 2026

1 piece
How we built Grok Bot in a month | Roman Ugarte (SpaceXAI)
AI (Horizontal)

Monday, 7 September 2026

2 pieces
🎙️ How I AI: GPT-6 Astra is a banger + Stripe’s AI playbook + Grok Bot vs. OpenClaw: why I replaced my entire agent stack
AI (Horizontal) · Enterprise Software
Build your own company brain: the enterprise AI playbook from Stripe’s engineering team | Sharadh Krishnamurthy
Enterprise Software · AI (Horizontal)

Sunday, 6 September 2026

1 piece
Why companies are becoming a series of loops | Anish Acharya (a16z)
Venture Capital & Startups · AI (Horizontal)

Saturday, 5 September 2026

1 piece
🧠 Community Wisdom: Driving AI adoption when habits are the bottleneck, leveling up from APM to a mid-level PM role, converting a wave of new users to subscription, and more
AI (Horizontal) · Marketing & Sales Tech

Thursday, 3 September 2026

1 piece
GPT-6 Astra is a banger - here’s everything I’ve built
AI (Horizontal) · Developer Tools

Wednesday, 2 September 2026

1 piece
Grok Bot vs. OpenClaw: How I replaced my entire agent stack
AI (Horizontal) · Developer Tools · Enterprise Software

Tuesday, 1 September 2026

1 piece
How to turn your AI into a world-class designer
AI (Horizontal) · Developer Tools · Marketing & Sales Tech

Monday, 31 August 2026

2 pieces
🎙️ How I AI: How this PM uses Claude to handle 70% to 80% of his workday
AI (Horizontal) · Enterprise Software · Developer Tools
How I turned Claude into a self-improving PM assistant | Daniel Blum (PM, Melio)
AI (Horizontal) · Enterprise Software

Sunday, 30 August 2026

1 piece
AI’s third era: the rise of persistent AI coworkers | Tara Seshan (Product Lead ChatGPT Work)
AI (Horizontal) · Enterprise Software · Developer Tools

Saturday, 29 August 2026

1 piece
🧠 Community Wisdom: Building without clear PM requirements, selling a product before building it, pricing fast-moving B2B SaaS, a year of job hunting, and more
Venture Capital & Startups

Tuesday, 25 August 2026

1 piece
How to figure out your next career move
HR & Talent

Monday, 24 August 2026

2 pieces
🎙️ How I AI: Grok Bot + Grok 4.6—what’s great (and what’s still hype) & Lessons from spending $20,000 on Devin in one month
AI (Horizontal) · Developer Tools
I spent $20,000 on Devin in a month. Here’s what I learned | Ryan Carson (solo founder)
Enterprise Software · Developer Tools · AI (Horizontal)

Sunday, 23 August 2026

1 piece
How to close $100K+ enterprise deals, step by step | Jen Abel
Marketing & Sales Tech · Enterprise Software

Saturday, 22 August 2026

1 piece
🧠 Community Wisdom: Favorite Lenny’s Product Pass tools, how AI is reshaping hiring, what to prioritize when you join a new company, and more
Venture Capital & Startups

Tuesday, 18 August 2026

2 pieces
I tested Grok Bot, Grok 4.6, and Cursor Origin - here’s my honest take
AI (Horizontal) · Developer Tools
Announcing Lenny’s Jobs: The best place in the world to find, vet, and land your dream job
Venture Capital & Startups

Monday, 17 August 2026

2 pieces
🎙️ How I AI: How a solo founder used Codex and ChatGPT to launch a fashion brand without engineers
Consumer · Retail & E-commerce · AI (Horizontal)
How a solo founder used Codex and ChatGPT to launch a fashion brand without engineers | Yana Welinder
Consumer · AI (Horizontal)

Sunday, 16 August 2026

1 piece
OpenAI’s Head of Design: This is the best time in history to be a designer | Ian Silber
AI (Horizontal) · Enterprise Software

Saturday, 15 August 2026

1 piece
🧠 Community Wisdom: Recovering from burnout, what Airtable’s sale says about the ceiling on a startup, keeping architecture docs up to date, running competitor analysis, and more
Venture Capital & Startups

Tuesday, 11 August 2026

1 piece
How to make people care about your startup
Venture Capital & Startups

Monday, 10 August 2026

2 pieces
🎙️ How I AI: Build an AI code review bot in 30 minutes + Claude Code for normal people
Developer Tools · AI (Horizontal)
Claude Code for normal people: skills, voice mode, and how to collaborate with AI
AI (Horizontal) · Developer Tools

Sunday, 9 August 2026

1 piece
The playbook for building high talent density teams | Adam Ward, Head of Talent at Cursor
Developer Tools · HR & Talent

Saturday, 8 August 2026

1 piece
🧠 Community Wisdom: Crafting outreach that reads as authentic, finding design partners, what counts as a moat when anyone can build, making a product vision stick, and more
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