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 Melanie Perkins (CEO of Canva):

1. Build a ladder to the moon with small rungs. You need both a crazy vision that reaches all the way to the moon and tiny, concrete steps to get there. Canva’s mission to “empower the world to design” became actionable through specific pillars: empower everyone to design anything, with every ingredient, in every language, on every device. The first step might feel embarrassingly small compared with your enormous goal, but each small step compounds over time.

2. Most people plan by looking at what they have now and asking what they can build with it. Melanie calls this “column A” thinking. Instead, start with “column B”: imagine the perfect future you want to create, then work backward to find the steps that get you there. When she started Canva as a university student with no experience, column A thinking would have led nowhere. Column B thinking—envisioning what design tools should look like in the future—created a $42B company.

3. Canva estimated a frontend rewrite would take six months. It took two years. During those two years, this product company couldn’t ship any new features. They turned it into a game with rubber-duck toys on a board to track progress and maintain morale, but it was “a dark tunnel” they had to push through.

4. Your biggest goals should make you feel completely inadequate. If a goal feels comfortable and achievable, it’s probably too small. A crazy big goal should make you feel inadequate—and that’s precisely the point. When something happens and you hit a roadblock, a reasonable goal lets you quit easily. But when the goal matters deeply to you, you’ll push through obstacles because the vision is worth years of hard work.

5. Turn rejection into refinement. After being rejected by over 100 investors, Melanie turned each rejection into an improvement in her pitch deck. When investors said the market wasn’t big enough, she added a slide showing market size. When they said Canva was the same as competitors, she created a slide showing the gap in the market. Each specific rejection made the pitch stronger and more refined.

6. Celebrate achievements. Crazy big goals require celebrating milestones along the way. When Canva launched in Spanish, hit 100 languages, or achieved other major goals, they celebrated by smashing Greek plates, releasing doves, or throwing festivals. These memorable celebrations give teams a moment to feel proud before continuing the climb toward goals that take years to achieve.


7. Build wealth as a means, not an end. Melanie and her co-founder committed the vast majority of their equity in Canva (about 30% of the company) to philanthropy through the Canva Foundation. They give away $1.5B worth of product annually and have committed more than $150m to give cash directly to people in extreme poverty Their two-step plan: build one of the world’s most valuable companies, then do the most good they can do—with each step fueling the other.

Deeply researched product, growth, and career advice

Top takeaways from my chat with Grant Lee (CEO of Gamma):

1. The first 30 seconds of using your product should be so good it earns the next 30 seconds. When Gamma wasn’t growing, they stopped everything and spent three months perfecting just the first 30 seconds of using their product. They made it so compelling that new users would immediately tell their friends. This single change transformed their growth trajectory.

2. Focus on one simple promise, not many features. Think of it like throwing eggs to someone: they can catch one, but if you throw five at once, they’ll drop them all. Your users are selfish, vain, and lazy—you have 30 seconds to show value before they leave. Gamma focused on “create a slide in seconds” rather than listing 10 features.

3. Don’t spend on ads until over half your growth comes from word of mouth. If you try to buy growth before your product spreads organically, you’re wasting money filling a leaky bucket.

4. Work with hundreds of small creators instead of a few big influencers. Rather than blowing your budget on five or six well-known influencers who treat it like just another ad read, find thousands of micro-influencers whose audiences genuinely care about tools like yours. Teachers sharing with teachers, consultants with consultants—these tight communities create authentic word of mouth that spreads fast.

5. Spend time personally onboarding each early creator like they’re joining your team. Don’t just send influencers a script. Jump on calls, walk them through the product, help them understand what makes it special, and let them tell your story in their own voice. This investment turns them into genuine advocates who post about you repeatedly instead of treating it like any other sponsorship.

6. Hire painfully slowly and only exceptional people. Gamma serves 50 million users with just 50 people and makes a profit. All 10 original employees are still there five years later. They never set headcount goals because that makes you hire to hit a number instead of hiring only when you find someone exceptional. When someone is exceptional, give them more responsibility, not less—top performers want harder challenges.

7. Test prototypes with 20 people on UserTesting before investing in a big project. Use platforms like Voicepanel or UserTesting to watch real people try your prototype. They’ll show you problems you never see because you’re too close to your product. Gamma goes from idea to results in a single day—morning idea, afternoon testing, evening results. This saves months of building things nobody wants.

8. Choose problems you’ll care about for 10 years. Before worrying about technology or tactics, ask if this problem matters enough to you personally that you’d dedicate a decade to solving it. Founders who are missionaries rather than mercenaries build better products because their authentic commitment shows through to customers and attracts people who want to build alongside you for the long term.

My biggest takeaways from Stewart Butterfield:

1. Product design is about creating understanding, not removing friction. Teams obsess over reducing friction and removing steps, but 70% to 80% of product design challenges are actually about helping people *understand* what your product does and what to do next. Users arrive barely interested and confused about what you offer. If they can’t quickly grasp what they’re looking at, they’ll leave. Making it easier to do confusing things just gets users to the exit quicker. The mantra should be “Don’t make me think,” not “reduce friction.”

2. You’re not selling features—you’re selling outcomes. Nobody wants a saddle; they want to go horseback riding. Nobody wants a hammer; they want something built. People understand cars and beer without explanation, but new software needs an explanation of both what it is and why they should want it. Slack wasn’t selling messaging features—it was selling better team coordination and reduced email chaos. If you can’t articulate the transformation your product creates in people’s lives, you’re just listing features.

3. Organizations naturally fill with fake work that looks exactly like real work, what Stewart calls “hyper-realistic work-like activities.” Meetings to preview deck slides, analysis of tiny feature differences, elaborate processes around insignificant decisions. People aren’t lazy; they’re responding to having more time than valuable work to do. Leaders must continuously ensure there’s enough valuable work and explicitly say no to projects that can’t possibly generate meaningful impact.

4. Small conveniences create emotional connections that drive word-of-mouth growth. No one switches products because of a good time-zone picker or smooth password recovery, but these details make users love or hate your product. Slack grew largely because people who used it at one company would join a new company and advocate strongly for adopting it. That advocacy came from accumulated small delights, not major features.

5. The “owner’s delusion” explains why bad experiences persist everywhere. Restaurant owners create terrible websites even though they’ve experienced the frustration of visiting other terrible restaurant websites. Business owners assume visitors care deeply about their product, when in reality people arrive distracted, in a hurry, just above the threshold of caring at all. The solution is to regularly step back, be a normal person with limited time and patience, and honestly evaluate if your product makes sense.

6. Only pivot after exhausting all reasonable ideas. The right time to pivot isn’t when things get hard—it’s when you’ve genuinely tried every non-ridiculous approach and can coldly, rationally assess that the expected value has dropped below alternatives. Pivoting is humiliating because you’ve convinced investors, employees, and users of a vision you’re now abandoning. That emotional cost means most people pivot too quickly or too late.

How tech workers really feel about work right now

With insights from over 8,000 of you (possibly the largest survey of its kind), Noam Segal and I are excited to share the results of our first-ever large-scale tech worker sentiment survey.

What we discovered is that tech professionals are experiencing a fascinating mix of emotions about their careers in 2025.

Our biggest takeaways:
1. Burnout is at critical levels: Almost half of our respondents are experiencing significant burnout.

2. Tech workers are more optimistic than we expected—but optimism is declining: 58.5% of tech workers remain optimistic about their roles, and 54.8% remain optimistic about their careers. However, there has been a significant negative sentiment shift over the past year.

3. Startup founders are the happiest people in tech: They’re the only group growing more optimistic while consistently outranking everyone else in workplace well-being.

4. Managers need help: Only 26% of tech workers consider their managers highly effective, while over 40% view them as ineffective.

5. Where people work makes little difference in how they feel about work—on the surface. But dig deeper, and hybrid workers are the happiest, remote workers are doing well, and in-office workers are experiencing hidden frustrations.

6. Small-company employees are doing the best: They outperform their large-company counterparts on nearly every work sentiment measure, from job enjoyment to sense of belonging.

7. The mid-career slump: Mid-career workers are struggling the most with burnout, lower job enjoyment, and the most pessimism about the future.

8. A widespread gap in career clarity: Many tech workers don’t know what they should be doing to continue developing in their careers.

Two bonus takeaways you'll find at the end of the report:
1. Women are more burned-out (but more engaged) than men
2. AI is keeping tech workers up at night

Don't miss the full report: https://lnkd.in/g8RZeFja

AI makes it so much easier to build. But here's the catch: everyone else has that same speed advantage.

So you turn to distribution. But here’s the second catch: the channels you’ve long relied on for growth (virality, sales, SEO, ads) are increasingly becoming less effective—for that same reason.

So how do you get your product noticed?

The answer is *ecosystem*. Instead of going directly to your prospects, go through intermediaries who already have access and trust with your audience.

Tom Orbach, director of growth marketing at Wiz, said it best: “Why start at zero when you can start at 10,000?”

You’re likely familiar with the individual tactics within an ecosystem strategy: influencer and creator relationships, channel partnerships, developer relations, communities, product integrations, and customer marketing. But the growth unlock doesn’t come from any one of these activities on their own.

Instead, a flywheel emerges when you properly implement this overarching strategy: your ecosystem partners create and distribute content, you amplify and repurpose their efforts, together you drive greater reach and credibility, new customers and partners come on board, and the cycle strengthens with each turn. Now your ecosystem is a powerful extension of your GTM team.

In today's powerful guest post, Emily Kramer shares how you can implement this strategy yourself, including dozens of real-world examples of how top AI companies like Lovable, Gamma, Clay, Vercel, Supabase, Vanta, Baseten, HubSpot, and others are executing this strategy.

Don't miss this one: https://lnkd.in/gPNUKDzi

🎧 Here's my conversation with the one and only Dylan Field, CEO and co-founder of Figma

We discuss:
🔸 Why AI makes design, craft, and quality the new moat for startups
🔸 What actually happened with the Adobe deal, and how he kept morale up after it fell through
🔸 His approach to maintaining pace and a sense of urgency 13 years in
🔸 How to systematically develop taste
🔸 How Figma decides which product lines to add
🔸 Why you need to be obsessed with “time to value”
🔸 Much more

Listen now 👇
• YouTube: https://lnkd.in/gjhMnCXQ
• Spotify: https://lnkd.in/gmEvWJRd
• Apple: https://lnkd.in/gSJV-HKe

⭐ This entire episode is sponsored by Stripe — Helping companies of all sizes grow revenue: https://stripe.com/

Stewart Butterfield rarely does interviews. After 2 years of trying, I finally convinced him to come on. 

In this special conversation, Stewart shares the frameworks and mental models that most helped him build two of the most important products in tech history (Flickr, and Slack—which he sold for $28B, and which powers how basically every company collaborates these days).

We discuss:
🔸 "Utility curves" — his framework for prioritizing ideas
🔸 "The owner's delusion" — why restaurant websites suck
🔸 "Tilting your umbrella" — a hilarious Slack core value
🔸 "Hyper-realistic work-like activities" — my new  favorite concept
🔸 "Don't make me think" — Stewart's foundational design philosophy
🔸 The story behind "We don't sell saddles here"

Listen now 👇
• YouTube: https://lnkd.in/gA5pEgPg
• Spotify: https://lnkd.in/gGSMvJ8m
• Apple: https://lnkd.in/gKEmDYhR

Thank you to our wonderful sponsors for supporting the podcast: 
🏆 WorkOS — Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny
🏆 Metronome — Monetization infrastructure for modern software companies: https://metronome.com/
🏆 Lovable — Build apps by simply chatting with AI: https://lovable.dev

I'm really excited about what Casey Winters is building at SuperMe.

It's not just a product—it's a living system of collective intelligence, made up of the wisdom of hundreds of seasoned operators and all of their collective wisdom.

-> Try it here: https://www.superme.ai/

Why it's so rad:
1. You can ask a business question you could use some advice on and get synthesized insights from multiple people who've actually navigated your challenges before.
2. They've already brought on some of my most popular podcast guests, like Elena Verna, Nikhyl Singhal, Brian Balfour, and many others.
3. Every individual on SuperMe sees what you ask their profile, and can chime in to add more context.

If you are an operator looking for battle tested advice on toughest problems, take a look at what SuperMe is doing.

You can also pick my brain here anytime: https://lnkd.in/gGsx8fJT

Open article: SuperMe - The Professional Network for the AI Age by superme.ai

SuperMe - The Professional Network for the AI Age

🎧 Watch me do a live coaching session with Rachel Lockett, a sought-after executive coach and former leader at Stripe and Pinterest.

We discuss:
🔸 When to coach vs. when to just tell people what to do
🔸 The GROW technique for helping people figure things out for themselves
🔸 Tips for making difficult conversations less difficult
🔸 Building and sustaining a healthy co-founder relationship
🔸 Avoiding burnout and designing a more energizing career
🔸 Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions

Listen now 👇
• YouTube: https://lnkd.in/gtYqcSF2
• Spotify: https://lnkd.in/g5sk_ZSE
• Apple: https://lnkd.in/gv4NBAzv

Thank you to our wonderful sponsors for supporting the podcast: 
🏆 Stripe — Helping companies of all sizes grow revenue: https://stripe.com/
🏆 Vanta — Automate compliance. Simplify security: https://vanta.com/lenny
🏆 Persona— A global leader in digital identity verification: https://lnkd.in/gn5Y6ict

Grant Lee on Gamma (valued at over $2.1B) being "just a GPT wrapper":

"When you think about literally only being a wraparound one model, yeah, maybe there's only a limited amount of utility or value add. But when you start going really deep into one workflow, and it's not just one model—it's maybe 20+ models powering all different parts of the product, your job is to maximize the value you're delivering to the end user in a way that's sustainable for you as a business.

For us, that's all we focus on—going deep into this workflow, being empathetic to the user and the job that you're trying to solve for them, and of course applying the best technology possible so that you're delivering on that promise of a product experience that's way better than the status quo."

Full conversation: https://lnkd.in/gZCZuVgh

InCharge Energy

Leading our software product team’s development of the InControl Charger Management System and our universe of ancillary and internal software tools.

Vice President, Digital Products

Director of Digital Products

Senior Product Manager

EVgo

Product Owner

Synacor

Product Manager for white labeled digital products including start.att.net, a news aggregator website with 3M daily unique visitors, and AT&T Live 2.0 Android app with an installed base of 800k+ devices. Coordinate three scrum teams for the web portal, which includes: research, analytics, ideation, feature and roadmap planning in AHA!, ticket writing in JIRA, sprint planning, and final approvals. PM a separate remote scrum team for the Android app. The job also entails client communication, collaboration, and reporting.

Product Manager

Supported management and product team with the development of web and native apps for Fortune 500 client. Responsibilities include reporting and analysis using Google Analytics, creating epics, stories and tickets in JIRA, tracking ideas in AHA!, ideation sessions and brainstorming on new features and capabilities, updating and maintaining the team Wiki in Confluence, tickets and preparation for A/B testing. Also wrote code for rapid prototyping project, including a live quiz app for Drupal (HTML, CSS, JavaScript, PHP) and a quiz skill for Amazon Alexa written in JavaScript/Node.js hosted with Amazon Lambda.

Product Management Intern

Self-Employed

I created, maintained, and updated websites on behalf of private clients. Projects included nonprofit, ecommerce, and portfolio websites. Utilized Shopify, WordPress, Squarespace, Amazon LightSail hosting and site builders. Customized sites writing custom HTML, CSS, JavaScript, jQuery, Ruby, PHP. 

Duties also included sales, client management, project management, QA/QE with unit testing, collaborating with design/UX and client, installing and analyzing tracking software for Google Analytics and HotJar heat mapping, integrating Stripe payment gateways, and content creation and copy editing.

Web Developer & Consultant

Climate Cents

Climate Cents is a platform for crowdfunding local, scientifically vetted, impactful projects that combat climate change. 

I am providing full stack developer duties. This includes maintaining the legacy WordPress site that is utilizing Angular and Stripe for payment processing and a SQL database, and designing a new site. The completed new iteration is a Ruby on Rails application utilizing Bootstrap 3, JavaScript (ES6), Angular.js 1.6, Stripe, and PostgreSQL. We utilized Kanban and Lean methodologies to create rapid prototypes and then MVPs to roll out to users and investors. 

Supporting software included Asana, Amazon S3 and Route 53, Cloudflare, Heroku.

Developer

GameTree

GameTree is a new kind of social network for gamers offering personal recommendations for games, friends, news, and events. 

My duties included providing QA and testing and writing code for the marketing site. The site was written in Meteor utilizing JavaScript (ES6), MongoDB, SASS, and Bootstrap, and included exposure to CoffeeScript and Foundation in earlier iterations. I also wrote marketing copy and gave the occasional piece of strategic advice.

Extenda Communications

Extenda provides voice, contact center, and network hardware and software. Managing a team of 15, we transformed from a solely premise-based equipment and service company into a SaaS business with a significant book of recurring revenue. As Product Manager, I oversaw the launch of our virtualized cloud-based VoIP system (VoiceSide) and telecom partnerships with leading carriers. Some of our customers included Berkshire Hathaway Home Services, j2 Global, Guthy-Renker, Laureate Education, Universal Bank, and Enterprise Rent-a-Car. While at Extenda, I learned enough web development to be dangerous, developing our website and ecommerce site in PHP and later Ruby on Rails.

Chief Executive Officer

Beecher Investors, Inc

Beecher Investors is a New York-based wealth management company and hedge fund.

I performed trading, investment research, compliance, and client service duties for private clients and the Gazelle hedge fund. This included mentoring Junior Analysts and support staff, and reporting directly to the Principal/Portfolio Manager. While there, I learned Visual Basic for Applications to automate Excel- and Access-based trading compliance paperwork and portfolio rebalancing.

Senior Analyst

Los Angeles Economic Development Corporation

Researched and produced economic reports and analysis on the five county Los Angeles metropolitan area.

Summer Analyst

I have been leading teams that create great user experiences at the intersection of the digital and physical worlds. Whether I am building a new product from scratch, working on our go-to-market strategy, or revamping an existing product, I get excited about talking to customers to understand their problems and collaborating across design, engineering, and business stakeholders to come up with solutions.

My current position is with InCharge Energy, working with an amazing team developing solutions for electrifying and managing charging for commercial fleets.

I have really enjoyed working with startups and early stage companies. In my most recent role as Product Owner at EVgo, I led the development of next generation native mobile apps for our retail customers. My cross-functional team had developers, designers, and QA testers following Lean & Agile principles. Beginning with extensive user interviews and behavioral studies, we created customer personas, conducted competitive research, established stakeholder requirements, developed a product vision and strategy, and then began the marathon development of Android and iOS apps. I have been writing the user stories, conducting our sprint ceremonies, forecasting delivery dates, participating in ongoing user research and A/B testing, demoing the product, and presenting our progress and findings to leadership and the company at large.

Prior to EVgo, I was a Product Manager at Synacor. At the time, Synacor was revenue-sharing partners with AT&T for their Start news aggregator web portal and Android app. During my tenure, the Android app grew to 800,000 unique downloads, with ARPU tripling, while the web portal, with 3 million daily uniques, was able to maintain $40M in ARR despite long term structural declines in AT&T's DSL business, which was the portal’s main distribution channel.

I have worked with a number of startups as a contract developer with product management responsibilities, and was CEO of my own VoIP B2B service business for ten years, where I had the good fortune of a successful exit in 2015. Running a business made me humble and resourceful, while giving me a crash course in marketing, sales, janitorial services, and accounting.

I believe leadership is about creating an environment for people to bring their best self to work. I make every effort to build competent, collaborative teams empowered to make smart decisions while having some fun in the process.

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Lenny Rachitsky

Russell Schmidt

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The Battle

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Russell Schmidt

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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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