Lenny's Newsletter

Author, Lenny’s Newsletter and Lenny’s Podcast

Self Employed

Investor in 150+ companies including Figma, Linear, Substack, Vanta, Anduril, Whatnot, Webflow, Descript, Levels, Mindbloom, Reforge, Zip, Stytch, Runway, Census, Pachama, and many more: https://www.lennyrachitsky.com/investing

Angel Investor

Airbnb

Led the team responsible for driving consumer supply growth. This included:

* Performance marketing
* Conversion
* Referrals
* Awareness and consideration
* Re-engagement
* Retention
* Core host products

Previously, led three teams driving Instant Book Growth (grew usage from 5% to over 80%), guest booking conversion, and building new tools for hosts (e.g. dashboards, calendar, guest controls, publishing, messaging).

Also supported strategy of the Anti-Discrimination team, and helped on a few side-projects including  work with The Malala Fund.

Product Lead, Supply Growth

Drove growth through improvements to guest booking conversion, host experience (acceptance rate, response rate, more), and Instant Book.

Drove host quality through launching programs such as Superhost, Mentors, Host Dashboard, host quality standards, revamp of reviews system, and more.

Built Airbnb's first host community platform.

Built the first attempt at extending Airbnb beyond the home (now Airbnb Experiences).

Product Lead, Guest Conversion and Host Quality

Localmind

Acquired by Airbnb in 2012.

Localmind was an early location-based consumer app. We leveraged location data from Foursquare, Facebook, and Gowalla to capture location expertise of locals, enabling Localmind users to get real-time answers to questions about places they are thinking about visiting.

https://angel.co/localmind
http://ireport.cnn.com/docs/DOC-574061
https://techcrunch.com/2012/12/13/airbnb-acquires-localmind/

Co-Founder, CEO

Webmetrics/Neustar

Focused on innovations in web performance, cloud, and web operations, looking 2-5 years down the road. Prototype, research, and build. Also included business development with partners.

Engineer, Head of R&D

Managed the entire engineering department of Webmetrics. This included building the team, building the product, and maintaining a 24/7 operations culture. During this period we were acquired by Neustar, and the team grew 10x.

Sr. Manager of Engineering

Webmetrics

Built the core product offering for Webmetrics, a website monitoring and load testing product.

Acquired by NeuStar

Lead Engineer

LA.com

Basic web development for all the LA.com and sister properties (e.g. hawaii.com, texas.com, more)

Web Developer

Upcoming podcast lineup 🔥

Dharmesh Shah, co-founder of HubSpot
Mihika Kapoor, Figma design-eng-PM hybrid
Kayvon Beykpour , ex-Twitter head of product 
Claire Vo, creator of ChatPRD, 3x CPO
Dalton Caldwell, YC managing director
Hamilton Helmer, strategy legend
Annie Duke, decision-making legend
Rory Sutherland, Ogilvy co-founder
Bangaly Kaba, YouTube, IG, Meta, Instacart
Carole Robin, Ph.D. Robin, instructor of "Touchy Feely" at GSB
Uri Levine, Waze co-founder, author
Jeff Weinstein, Stripe product legend 
David DeSanto, GitLab CPO
Tomer Cohen, LinkedIn CPO

If there's a person you'd love to see on the pod, please leave a comment and let me know.

Lenny Rachitsky

Mihika Kapoor is a PM at Figma where she’s known as the go-to person for leading 0-to-1 products. She was an early PM of FigJam, is currently leading a new (undisclosed) product that’s launching at Figma’s Config conference this year, and is beloved by everyone who works with her.

In our conversation, we discuss:
🔸 Advice for taking ideas from 0 to 1 at larger companies
🔸 How to craft a compelling vision
🔸 How to tactically communicate your vision
🔸 The importance of vulnerability and feedback
🔸 Advice for building a strong team culture
🔸 Pivoting priorities with grace and enthusiasm
🔸 AI and its impact on PMs
🔸 Much more

Listen now 👇

YouTube: https://lnkd.in/gMed2MdG

Spotify: https://lnkd.in/gbNUk-Zc

Apple: https://lnkd.in/gNb4pBDy

Key takeaways:

1. Putting ideas out there, even if they are wrong, can lead to better solutions and more productive discussions. It’s not just about having a great idea or building a prototype; it’s about actively engaging and rallying others around that idea to create momentum and excitement. Whether it’s pitching ideas at events like hackathons or simply asking colleagues for assistance, the key is to not let perceived limitations hold you back from pursuing your vision.

2. Mihika likens the role of a 0-to-1 team within a large company to that of Hestia in Greek mythology, who is the “keeper of the hearth.” It is Hestia’s job to always keep the hearth burning, even while other gods go out on separate quests. This means always keeping the 0-to-1 project alive and helping it spread to others, mostly through setting vision and building hype.

3. To set the vision for a new idea, ask: “If I and my team do our job correctly, what does the world look like?” Then convey the pain point, solution, and proof in a format that can “show, not tell” stakeholders what you’re doing. For example, use prototypes, Figma mock-ups, and customer testimonials.

4. Internal hackathons are a great way to encourage innovation. Figma has a Maker Week where the entire company—including technical and non-technical employees—goes on pause for a week to work on ambitious ideas. Maker Week and other internal hackathons have led to many successful Figma products, including Jambot and Figma’s entire widget platform.

5. Figma implements a fun “hot seat” tradition, where each person takes turns being in the hot seat for a set amount of time. During their turn, the person can be asked anything by the other members of the group. By understanding what motivates each team member and building strong relationships, collaboration becomes more effective, leading to a more enjoyable work environment and ultimately better outcomes for the product or project. The key is to create a comfortable and friendly atmosphere where everyone feels open to sharing.

How to make an impact in your first 90 days

25 quick wins ideas from some of my favorite product/growth leaders in tech including Elena Verna, Geoff Charles, Jules Walter, Madhavan Ramanujam, Claire Vo, Jiaona Zhang (JZ), Christopher Miller, Melissa Tan, and many more

Don't miss today's 🔥 post by Kyle Poyar: https://lnkd.in/gKssce6F

Deeply researched product, growth, and career advice

💥🧑‍🎓 Announcing: Lenny’s Newsletter Fellowship Program 🧑‍🎓💥 

I’m launching a three-month fellowship program, and applications are now open.

What is it: Work alongside me to learn how I do what I do, share your unique knowledge with the world (through guest posts), and jump-start (or simply explore) a newsletter/podcast career.

Why: The best operators in the world are too busy doing real work to have time to write publicly or explore the newsletter or podcast life. I want to create a low-risk, low-friction way for you to unlock the knowledge in your head while benefiting the next generation of product builders and helping you explore the solopreneur path.

How it works: This is a paid fellowship lasting three months (you’ll be paid $30,000), limited to three people, beginning in July (although timing is flexible). We’ll collaborate on guest posts and the podcast (and anything else that interests you), and you’ll leave with published content and a pre-built audience. Expect to spend 5 to 10 hours per week during the fellowship, all async and remote; location doesn’t matter.

This is my first time doing this, so we’ll all learn as we go!

Click below to learn more about the ideal applicant, the expertise I’m most looking for, and other logistics 👇

docs.google.com • 1 min read

Apply to be a Lenny’s Newsletter Fellow ✨

The best way to learn how to use AI in your work is not to read about it—it's to use it.

The fine folks at GoPractice, Inc built a hands-on generative AI simulator designed specifically for PMs. Through simulations and real-time exercises, it teaches you how to apply generative AI to create products and automate processes at your company.

You'll learn how to do things that used to require an advanced ML team, that now can be done in a few hours by a single product manager.

Even better, for a limited time, they made the course completely free for people that follow me. Learn more and sign up here:
https://lnkd.in/gRTCc9xp

P.S. I'm not affiliated with these guys, and I'm not making anything off of this. I just think this is very cool, and will help a lot of people, so I'm happy to spread the word.

gopractice.io • 2 min read

Generative AI for Product Managers – Mini Simulator

Dharmesh Shah is the co-founder and CTO of HubSpot, and one of the most fascinating and first-principled-thinking founders I’ve ever met. Dharmesh is the keeper of HubSpot’s Culture Code, creator ChatSpot (an AI chatbot built on top of HubSpot CRM) and a game called WordPlay (which grew to 16m users), founder and writer for OnStartups.com (a top-ranking startup blog and community with more than 1m members), and that's just a small portion of the fun facts about Dharmesh.

In our conversation, we discuss:
🔸 How to decide what ideas are worth investing in
🔸 The biggest lessons he has learned from building HubSpot into a $30B+ business
🔸 Dharmesh’s unique strategy for public speaking
🔸 The importance of leaning into your strengths
🔸 The decision-making process at HubSpot
🔸 How Dharmesh developed HubSpot’s culture code
🔸 His contrarian approach to building products
🔸 Why founders and product teams are all fighting the second law of thermodynamics
🔸 How “flash tags” can save your team time
🔸 Much more

Listen now 👇

Spotify: https://lnkd.in/gdTgYZSj

Apple: https://lnkd.in/gUxGheaj

YouTube: https://lnkd.in/gsjqyvy5

Over the past five years, Duolingo has been on an unprecedented tear. They 6x'd their daily active users (from 5 million to nearly 30 million), and in just the past two years the stock has nearly 3x’d. For a company that’s over a decade old and that's gone through a multi-year growth deceleration—this is not something you see.

Sean Colombo (VP of Engineering) has been there through it all, and in today's newsletter, Sean shares his five biggest lessons about what has been driving Duolingo's exponential growth.

“How Duolingo reignited user growth,” by Jorge Mazal, is my #1 most popular post of all time, and this is a post continuation of that story.

Key lessons:
1. 📈 Maintain a sense of urgency to drive compound growth
2. ♟️ Identify your strategic advantage
3. 🫢 Copy first, then innovate
4. 🦢 Notifications are the goose that lays the golden eggs—don’t kill the goose
5. 🍕 Consider the whole pie (total impact) when prioritizing work

lennysnewsletter.com • 3 min read

The secret to Duolingo’s exponential growth

A semi-comprehensive list of the day-to-day work that a PM does, ranked by how much I believe AI will disrupt that work in the future, on a scale of 1 to 5 🤖s. The more 🤖s, the more AI will take it over.

Takeaways:
1. Soft skills—like influence, communication, product sense, creativity, and empathy—will become ever more valuable to the role of product management. Lean into building these skills.
2. Some of the most high-value skills—like strategy, vision, discovery, data fluency (and even engineering)—will be significantly impacted by AI. As a result, you’ll want to learn how to work with AI tools (e.g. asking great questions) to build leverage in these areas.
3. Broadly, PMs will continue to be the “glue” or “conductor” who ties everything together, helping your company’s most important assets (both people and AI) drive the most possible impact in the shortest amount of time.
4. The PM role isn’t going away, and I believe it will become even more important.

For a lot more on this topic (including favorite AI tools within each bucket), don't miss the full post: https://lnkd.in/g9R9YBcv

One of my favorite lessons from yesterday's post on Duolingo

Full post: https://lnkd.in/g2n4S8HW

Everyone loves launching new features, but in my experience, most growth comes from the less sexy work: incremental and consistent optimization of your core product.

Surprisingly, I’ve never seen a great framework for how to methodically think about increasing the adoption of features after they’ve launched. Until now.

Introducing the ARIA framework—by Ken Rudin: https://lnkd.in/g_ZZiwM9

Ken developed this framework over the course of his career. And his background is bonkers: He was one of the first senior execs on Facebook's legendary early growth team, led growth at Google for many years (including Google search, ads, and cloud), led the Growth and Analytics team at Zynga, was the first SVP of Products and Engineering at @Salesforce, and most recently helped ThoughtSpot (an AI-enabled analytics vendor) transition their growth motion from a traditional sales-led B2B SaaS model to product-led growth.

There’s a lot of hate for micro-optimization product work, and I’m here to tell you that this work is important. Maybe the most important. 👇

lennysnewsletter.com • 12 min read

How to accelerate growth by focusing on the features you already have

I spent a bunch of time thinking about how AI will impact/replace the PM role in the near future.

Broadly, the PM role isn’t going away, and I believe it will become even more important. PMs will continue to be the “glue” or “conductor” who tie everything together, helping your company’s most important assets (your people and AI systems) drive the most possible impact in the shortest amount of time.

Surprisingly though, I've realized some of the most high-value skills—like strategy, vision, discovery, and data fluency—will be significantly impacted by AI. As a result, you’ll want to learn how to work with AI tools (e.g. learning to ask great questions) to build leverage in these areas.

On the other hand, soft skills—like influence, communication, product sense, creativity, and empathy—will become more valuable. PMs should be leaning into building these skills even more.

To show you what I mean, I’ve created a semi-comprehensive list of the day-to-day work that a PM does and ranked how much I believe AI will disrupt that work on a scale of 1 to 5 🤖s (the more 🤖, the more AI will take it over). I’ve also included tools that can help with these jobs today that you may want to check out.

This is just the beginning of a long discussion that we'll all be having more and more. I'd love to hear what you think. Agree? Disagree? Any insights or lessons from your own experience so far?

lennysnewsletter.com • 8 min read

How AI will impact product management

Claire Vo is the creator of ChatPRD (likely the most popular PM-specific AI product out there, which she builds on nights and weekends), and is chief product officer at LaunchDarkly. Before LaunchDarkly, she was a longtime chief product officer at Color and Optimizely. Claire has also been a two-time founder, engineer, designer, and marketer.

In my conversation with Claire, we discuss:
🔸 Finding your zone of genius
🔸 Knowing what you want in your career
🔸 How to maintain a fast pace in larger companies
🔸 How to make it easy for your boss to help
🔸 Advice for navigating the tech industry as a woman
🔸 The emerging role of a CPTO
🔸 Why she built ChatPRD
🔸 Tips for building your own AI tools
🔸 The impact of AI on product management and what skills will continue to be important
🔸 Much more

Listen now 👇

YouTube: https://lnkd.in/gVkv2Evz

Spotify: https://lnkd.in/gKpNsDfc

Apple: https://lnkd.in/gTXP3mDW

David DeSanto is chief product officer at GitLab— one of the most unique companies I've encountered. They are valued at over $10B, are the largest remote-only company in the world, publish their internal team meetings on YouTube, and share their 2,000-page employee handbook which includes their company strategy, roadmap, HR policies, and more.

In our conversation, we discuss:
🔸 How (and why) GitLab operationalizes transparency
🔸 The philosophy behind recording and sharing team meetings on YouTube
🔸 GitLab’s core value of having “short toes”
🔸 Challenges and advice for doing remote work well
🔸 Strategies for ensuring effective communication in a remote work environment
🔸 GitLab’s breadth-over-depth strategy
🔸 The company’s unique approach to AI
🔸 The value of using humor in high-stakes conversations
🔸 Much more

Listen now 👇

YouTube: https://lnkd.in/gePqdbYr

Spotify: https://lnkd.in/gNcQBH53

Apple: https://lnkd.in/gyAaH6JY

Key takeaways:
1. The company shares internal meetings on YouTube, maintains a public issue tracker for projects, and provides a 2,000-page handbook detailing their operational procedures. This dedication to transparency has enhanced user trust and encouraged community engagement, retention, and growth.

2. In an all-remote culture, GitLab promotes overcommunication to maintain clarity and cohesion among team members. Clear, concise, and constant communication helps prevent misunderstandings and ensures that everyone is on the same page despite the lack of in-person interaction.

3. GitLab’s feedback approach:
a. Having “short toes”: GitLab emphasizes the importance of separating personal identity from professional output when receiving feedback. This concept encourages people to approach feedback with an open mind, focusing on collaboration and growth rather than defensiveness. By embracing constructive criticism as an opportunity for improvement, teams can foster an environment conducive to innovation.
b. Private delivery of negative feedback: GitLab advocates for delivering negative feedback in one-on-one settings rather than public channels. This approach promotes respect and professionalism, ensuring that constructive criticism is provided in a manner that preserves the recipient’s dignity. It also allows for meaningful dialogue and follow-up discussions to address areas of improvement effectively.

4. Kindness is a core value at GitLab, woven into collaborative principles such as expressing gratitude and apologizing when necessary, and delivering constructive criticism in private rather than public channels.

5. Responsibility is “driven down” to GitLab’s lower levels, empowering individuals and teams to own and manage their projects. This approach fosters efficiency by streamlining decision-making and maintaining a high level of project velocity.

Todd Jackson was VP of Product and Design at Dropbox, Director of Product at Twitter, Product Lead for Gmail at Google, PM for Facebook's Newsfeed, Photos, and Groups, and also the founder of Cover (which he sold to Twitter).

Today, Todd is a partner at First Round Capital where over the past year, he and his team have analyzed all of their internal data and the journies of the hundreds of startups they’ve worked with to put together a highly actionable framework to help founders find PMF. And it's amazing.

In our conversation, we discuss:
🔸 First Round Capital’s four-part PMF framework
🔸 Examples of companies at each level
🔸 How to know if you’re stuck at a level, and how to get unstuck
🔸 What to change when you’re stuck: persona, problem, promise, and product
🔸 The specific goals at each stage of PMF
🔸 The most common pitfalls at each stage
🔸 Much more

Listen now 👇

YouTube: https://lnkd.in/gBtVTKEs

Spotify: https://lnkd.in/gJ3JvXUm

Apple: https://lnkd.in/gw5y6dtD

Why India is great for MAUs but tough on ARPUs.

Clip from my conversation with Kunal Shah: https://lnkd.in/gptXnrq2

Pro tip for speaking well on the spot—use the simple structure:
1. What? 
2. So What?
3. Now What?

Clip from my chat with Matt Abrahams: https://lnkd.in/gmVV4gH5

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