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

Fintech | Embedded Finance | E-commerce

I am a fintech enthusiast and product leader passionate about crafting simple solutions for complex problems. I have successfully launched several products in the payments and fintech space, consistently driving growth for early-stage startups and enhancing customer satisfaction for established ventures. Additionally, I run the Fintech Wrap Up newsletter, sharing the latest industry news and insights, and serve as a pro bono peer mentor in product management, demonstrating my commitment to giving back to the community.

Sam Boboev

Today I took a step that feels both exciting and terrifying.

After almost seven years working in the fintech industry, I made the decision to leave my full-time job and focus fully on building my own media venture.

Fintech Wrap Up started as a side project. I worked on it late at night, on weekends, during flights and in between meetings. I never imagined it would grow into a community of people who trust my voice and look for clarity in a very noisy industry.

But the more I learned, the more I realised something important. Customer acquisition is hard. Brand trust is hard. Reaching the right audience is hard. I felt it myself for years.

So I am choosing to build something that helps solve this. I want to help fintech, payments, crypto and banking teams reach a real audience, tell their stories with confidence, and grow in a smarter way.

I am excited. I am scared. But I am ready.

I am also opening up to collaborations and conversations with brands that want to connect with this audience in a meaningful way. And I will start creating more video content to share insights and stories that matter in our industry.

Thank you to everyone who has supported me. This is the start of a new chapter.

Founder & CEO at Fintech Wrap Up | Payments | Wallets | AI

🚨 BREAKING: Checkout.com adopts ACP, backed by OpenAI, to power agentic commerce for enterprise merchants

What does that actually mean? It means AI agents can now discover stuff, choose what to buy, and check out for you. All inside platforms like ChatGPT.

And Checkout says this is not some cute side project. Their research shows agentic commerce could take twenty one percent of monthly household spending in the next five years. That is insane.

Here is the wild part.

Enterprise merchants will get instant, secure checkout inside AI chats.
And they still keep full brand control while the agent does the shopping.

Checkout is also building the guardrails. Verified onboarding, identity, fraud tools. Basically a whole trust layer for AI agents to spend money safely.

And they are already partnering with Visa, Mastercard, Google. Working on global standards for tokenized, intelligent payments.

So yeah. The shift from users to agents is not coming. It is happening right now.

🚨 BREAKING: Visa and AWS announced a major collaboration focused on agentic commerce.

Visa is listing Visa Intelligent Commerce in AWS Marketplace, giving developers direct access to payment tools like authentication, tokenized payments, personalization, and intent capture. AWS for Financial Services and Visa are also releasing open blueprints in the Amazon Bedrock AgentCore repository for fully automated workflows across industries. These include travel booking agents, retail shopping agents, and upcoming B2B payment and reconciliation agents.

The blueprints define how AI agents can handle discovery, comparison, booking, checkout, payment, tracking, and refunds end-to-end. All workflows integrate with the Visa MCP Server and APIs for secure, contextual, network-agnostic transactions. AgentCore provides identity, runtime, gateway, memory, and observability for orchestrating these agent systems.

Visa positions Intelligent Commerce as the trust layer for the agent economy, enabling safe, autonomous payments at scale. AWS frames the collaboration as a way to simplify fragmented commerce systems and make it easy for customers to build and deploy real agentic workflows.

The partnership aims to move agentic commerce from concept to developer-ready, with early collaborators including Expedia Group, Intuit, lastminute com, and Eurostars Hotel Company.

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The Battle

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Sam Boboev

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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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