Mike Fiorillo

Helping startups grow | CRO | PLG | Experimentation | Solopreneur | Ex-InVision, DuckDuckGo, FreshBooks | Reforge

Helping startups grow. Specialize in conversion rate optimization (CRO), user insights, and behavioral design/user psychology. Previously led growth at Temporal, DuckDuckGo, InVision. 1,000+ experiments across full-time roles and dozens of high-ROI consulting engagements.

Principal Consultant and Founder

Mike Fiorillo 🚀

I write Lenny's Newsletter (the #1 business newsletter on Substack), and host Lenny's Podcast (top ten tech podcast globally). Previously, I spent seven years at Airbnb leading supply growth, conversion, trip quality, and community, and before Airbnb, I was an engineer and a founder (exited to Airbnb).

Lenny Rachitsky

My biggest takeaways from Boris Cherny (Head of Claude Code):

1. Coding is now “solved” for most use cases. Boris hasn’t written a single line of code by hand since November, with 100% of his work now authored by Claude Code. At the same time, he remains one of the most productive engineers at Anthropic, shipping 10 to 30 pull requests daily while leading the team.

2. Anthropic has seen a 200% increase in engineer productivity since adopting Claude Code. As Boris notes, “Back at Meta, with hundreds of engineers working on productivity, we’d see gains of a few percentage points in a year. Now we’re seeing hundreds of percentage points.”

3. AI is moving beyond writing code to generating ideas. “Claude is starting to come up with ideas. It’s looking through feedback, bug reports, and telemetry, then suggesting features to ship.”

4. The next roles to be transformed are those adjacent to engineering. Product managers, designers, and data scientists will see similar transformations as agentic AI expands beyond coding. “Any kind of job where you use computer tools will be next.”

5. Build for the model six months from now, not today. One of Boris’s key principles is to design products for future AI capabilities, not current ones. “It’s going to be uncomfortable because your product-market fit won’t be very good for the first six months. But when that model comes out, you’ll hit the ground running.”

6. Watch for “latent demand.” Claude Code was built by observing what people were already trying to do, and then making it easier. Cowork emerged when they noticed people using Claude Code for non-coding tasks like analyzing MRIs or recovering wedding photos from corrupted drives.

7. Don’t optimize for token cost. Boris advises companies to give engineers unlimited tokens during experimentation phases. “At small scale, the token cost is still relatively low compared to their salary. If an idea works and scales, that’s when you optimize it.”

8. Underfund headcount on purpose. When Boris puts one engineer on a project, they’re forced to let AI do more of the work. Constraint drives creative use of AI tooling, not just faster typing.

9. The most successful people in the future will be generalists. “Try to be a generalist more than you have in the past. Some of the most effective engineers cross over disciplines. The people who will be rewarded most won’t just be AI-native—they’ll be curious generalists who can think about the broader problem they’re solving.”

10. Always use the most capable model, not the cheapest. A less intelligent model often burns more tokens correcting mistakes than a smarter one spends getting it right the first time. Boris runs maximum effort on Opus 4.6 for everything.

Here's the full conversation: https://lnkd.in/gxMjk8Az

Deeply researched no-nonsense product, growth, and career advice

My biggest takeaways from Jenny Wen (Claude design lead at Anthropic):

1. The traditional design process is breaking down. The classic discover-diverge-converge loop that designers have relied on for years doesn’t work when engineers can spin up seven coding agents and ship a working version before a designer finishes exploring options.

2. Design work is splitting into two distinct modes. The first is supporting execution: consulting with engineers as they build, giving feedback, polishing in code. The second is setting short-range vision, now scoped to three to six months instead of multi-year roadmaps. The vision work is still critical because when everyone can build anything fast, someone needs to point the team in a coherent direction.

3. Build trust through speed, not perfection. Anthropic ships products early, labels them research previews, and then iterates publicly based on real feedback. Jenny argues that what actually degrades a brand isn’t launching something rough; it’s launching something rough and then going silent. If you ship fast, respond to feedback visibly, and keep improving, users will trust you more, not less.

4. The most overlooked hire in design right now is the cracked new grad. Most companies are hiring senior designers with deep experience. Jenny argues that early-career people with blank slates, fast learning curves, and no attachment to legacy processes may be uniquely suited to this moment. They don’t carry baked-in rituals that are now obsolete, and their lack of expectations can actually be an advantage.

5. Chat as an interface isn’t going away. Despite expectations that chatbots were a temporary stop on the way to richer UIs, Jenny sees chat as a permanently valuable interface because it offers infinite flexibility. But she expects a hybrid future where models increasingly generate UI elements on the fly for specific tasks (like the interactive widgets Claude recently shipped) while chat remains the connective tissue between them.

6. Jenny went from design director (12 to 15 reports) back to IC. She questioned whether middle management had a safe future and wanted hands-on time during a period of rapid change. The IC time is giving her hard skills she wouldn’t have gained while managing.

7. AI will likely get better at taste and judgment. Jenny says designers may be holding onto “taste” as a moat too tightly. But someone still has to be accountable for what ships, the same way an engineer is accountable for AI-generated code.

8. Figma is still essential, but for different reasons. Jenny says Figma remains the best tool for rapidly exploring 8 to 10 different design directions on a canvas, something that coding tools handle poorly because they’re too linear and create investment bias toward one direction. For micro-level visual and interaction decisions, spatial exploration still beats sequential iteration.

Watch our full conversation: https://lnkd.in/gunZXqq8

Claude design lead: The classic design process is dead.

Here's what's replacing it.

Jenny Wen leads design for Claude at Anthropic, was previously director of design at Figma, and a designer at Dropbox, Square, and Shopify.

In our in-depth conversation, we discuss:
🔸 Why the classic discovery → mock → iterate design process is becoming obsolete
🔸 What a day in the life of a designer at Anthropic looks like, including her AI tool stack
🔸 Whether AI will eventually surpass humans in taste and judgment
🔸 Why Jenny left a director role at Figma to return to IC work
🔸 The three archetypes Jenny is hiring for now

This conversation changed how I think about the future of design.

Listen now: https://lnkd.in/gXH8vmM9

Thank you to our wonderful sponsors for supporting the podcast: 
🏆 Mercury — Radically different banking: https://mercury.com/
🏆 Orkes — The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/
🏆 Omni — AI analytics your customers can trust: https://omni.co/lenny

Also available on:
• Spotify: https://lnkd.in/gaeTW3Hg
• Apple: https://lnkd.in/gUBY2Nt3

I've teamed up with the team at Maven to put together a series of LIVE workshops centered around the theme of "The AI-Native PM," featuring a stacked lineup of product leaders: Tomer Cohen, Wes Kao, Hamel Husain, Peter Yang, Marily Nika, Ph.D, Tal Raviv, Aman Khan, Hila Qu 曲卉, Ben Erez, Ethan Evans, Caitlin Sullivan, and many more.

The workshops are across 3 themes and all totally free:
1. AI workflows
2. Becoming more technical
3. Product sense & influence

A few years from now, these skills will be table stakes for PMs. If you want to learn where things are heading in a hands-on way, this is the perfect way

Open article: The AI-Native Product Manager by bit.ly

Today I'm releasing my entire newsletter archive (350+ posts) and all podcast transcripts (300+ episodes) as AI-friendly Markdown files. Plus an MCP server and GitHub repo.

A few months ago I shared my podcast transcripts on a whim, and y'all built the most amazing things—an RPG game, a parenting wisdom site, infographics, a Twitter bot, and 50+ other projects.

Let's see what happens when I give you even more data.

Grab the data here: LennysData.com.

Paid subscribers get all of the data (some 350 posts and 300 transcripts). Free subscribers get a subset.

I don’t think anyone’s ever done anything like this before, and I’m excited to give you this excuse to play with that AI tool you've been meaning to try.

Check out today's newsletter post by Ben Shih for inspiration on what you could to build: https://lnkd.in/ggUNqEsb

Here’s my challenge to you: build something, and let me know about it. I’ll pick my favorite and give you a free 1-year subscription to the newsletter. Just post a link to your project in the comments here: https://lnkd.in/ggUNqEsb.

If you’ve already built something, slurp in this new data and submit it, too. I’ll pick a winner on April 15th.

LFG.

When a team is underperforming, most people's first instinct is to blame the people. That's almost always wrong.

After 20+ years at Meta, Google, and Chan Zuckerberg Initiative — and advising leaders at Stripe, Anthropic, OpenAI, and more — this week's beloved guest author Molly Graham has learned that blaming people for structural problems is one of the biggest leadership traps there is.

In her powerful post, she shares a simple diagnostic tool she's used since leading wilderness expeditions in Patagonia at age 22: the Waterline Model.

The Waterline Model helps you answer one question: What's going on below the surface that's making things harder than they should be?

In other words, "snorkel before you scuba."

Read it here (and share it with your manager):

Open article: How to debug a team that isn’t working: the Waterline Model by lennysnewsletter.com

How to debug a team that isn’t working: the Waterline Model

Marc Andreessen calls him "the best AI CEO nobody knows about."

Elad Gil calls his company "the most successful, most quiet company in AI."

Qasar Younis is the co-founder and CEO of Applied Intuition—which brings AI to vehicles, like tractors, planes, submarines, mining rigs, cars, and more.

The company is valued at over $15B, with 18 of the top 20 global automakers (and the U.S. Department of Defense) as customers.

As Qasar shared, "not many people run a $15B+ physical AI company with revenue and free cash flow. And by not many, I think literally zero other people."

And Qasar's personal story is wild: Born on a farm in Pakistan. Emigrated to the U.S. and grew up in Detroit managing engine lines at GM. Harvard MBA. Became COO of Y Combinator (during the era that funded OpenAI, Cruise, DoorDash, and Coinbase). Then left to start Applied Intuition in 2017.

In a rare and in-depth interview, we discuss:
🔸 The counterintuitive reason he's stayed quiet and built in private
🔸 Why reading old books and cleaning your own office makes you a better founder
🔸 How to build a culture where the best idea wins, not the loudest voice
🔸 Why the best companies show traction early—and what to do if yours doesn't
🔸 How physical AI will transform farming, mining, and construction before it ever reaches your home

Listen now 👇
• YouTube: https://lnkd.in/gHzqY9-n
• Spotify: https://lnkd.in/gXQgxMvF
• Apple: https://lnkd.in/ghm3BEmu

Thank you to our wonderful sponsors for supporting the podcast: 
🏆 Omni— AI analytics your customers can trust: https://omni.co/lenny
🏆 Vanta — Automate compliance. Simplify security: https://vanta.com/lenny
🏆 Lovable — Build apps by simply chatting with AI: https://lovable.dev/

Head of Claude Code Boris Cherny: "Everyone's going to be a product manager. Everyone's going to code."

This week's post on using AI for your job interview has proven very popular, in particular the AI interview coach that's included in the post.

To take this even further, Noam Segal took all of the feedback he's received about the interview coach and made three major improvements:

1. Enhanced memory: It now tracks which questions companies actually ask, what patterns keep showing up, and what's working (or not) for you specifically.

2. Higher challenge: The coach will push back a lot more, stress-test your stories, and give you more hard truths.

3. More guidance: Every command now ends with a specific recommendation for a next step, vs. waiting for you to figure it out.

Download v2 of the coach here: https://lnkd.in/gZkCBR34

PMs, engineers, and designers are the worst negotiators in tech.

Jacob Warwick negotiates comp for Fortune 500 execs, professional athletes, and Hollywood talent. He's helped his clients secure over $1B in additional comp.

And he says most product people leave at least 20% on the table—because they're afraid to say one sentence.

As someone who's been terrible at negotiating my whole life, this was one of the most valuable conversations I've had on the podcast. Jacob shares his full playbook:
🔸 Why a simple "What's the chance there's a little more here?" often unlocks a 20% bump
🔸 When negotiation actually starts (hint: it's much earlier than you think)
🔸 Why Jacob sees 40% average movement when negotiations are run well
🔸 Why you should never negotiate over email (and what to do instead)
🔸 How to dodge "What's your comp expectation?" without anchoring too low

Listen now: https://lnkd.in/g9BvQ9KZ

Thank you to our wonderful sponsors for supporting the podcast: 
🏆 Orkes — The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/
🏆 Mercury — Radically different banking: https://mercury.com/
🏆 Omni — AI analytics your customers can trust: https://omni.co/lenny

Also available on:
• Spotify: https://lnkd.in/gMCmEEhV
• Apple: https://lnkd.in/gXBAjDHc

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Lenny Rachitsky

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The Battle

Mike Fiorillo 🚀

Lenny Rachitsky

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Lenny Rachitsky's LinkedIn Performance

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Performance ScoreLenny Rachitsky's LinkedIn Performance