Lenny Rachitsky’s Post

One of my favorite tactical nuggets from Jeff Weinstein: Start tracking when your users have a "bad day" using your product

"The moment a customer felt compelled enough to go out of their way to talk about some problem with your product, to the world or to you, that's an unbelievable gift. That should be P0 alert-level intensity." —Jeff Weinstein Here's our full conversation: https://lnkd.in/gShRtsME

The London product community is incredible. What a turnout, and such ✨ vibes. Huge thank you to Index Ventures for hosting 👏

Jeff Weinstein is a product lead at Stripe where he helped grow their payment APIs to hundreds of billions in volume and transformed the way founders start companies into a few simple clicks with Atlas. Prior to Stripe, Jeff led several startups and sold companies to Groupon and Box. He’s known for his customer obsession, craft, quality, and building beloved products businesses rely on. In our conversation, we discuss: 🔸 The power of customer obsession and how to operationalize it in your product development process 🔸 How to pick the right metrics and use them to drive impact 🔸 Techniques for getting things done at big companies 🔸 A group practice Jeff started to uplevel product craft, called Study Group 🔸 The story behind Stripe Atlas and its mission to increase entrepreneurship globally 🔸 Lessons from working with the founders of Stripe Listen now 👇 YouTube: https://lnkd.in/gE2HeQq3 Spotify: https://lnkd.in/gdADCBQs Apple: https://lnkd.in/gW79ZutA Some key takeaways: 1. Before focusing on craft, experience, or quality, you need to ensure that you’re solving a burning problem for someone. One of Jeff’s first companies went offline for hours and not a single customer reached out—that’s when he knew they didn’t have product-market fit. If users aren’t clamoring for your product, you’re not solving a real need. Think about it this way: solving the core problem is the main course; perfecting craft, UX, and quality are the desserts. 2. Jeff emphasizes the “go, go, go ASAP + optimistic, long-term compounding” approach: seize opportunities with enthusiasm while maintaining a strategic focus on long-term growth. Stripe’s evolution in global payment methods exemplifies how combining rapid execution with thoughtful, enduring strategies leads to significant, sustainable results. 3. When customers take the time to complain or provide feedback, treat it as a gift. Respond promptly to complaints or feedback, even if it means interrupting other tasks, as it creates a direct signal between you and the customer. This responsive attitude can lead to a loyal customer base and product improvement. 4. Ask customers to describe what a “bad day” looks like when using your product, and then find ways to track metrics around those frustrations. You don’t necessarily need to solve every issue right away, but having this problem library builds awareness to inform your roadmap.

Mike Maples, Jr passed on Airbnb at a $1.5m valuation 🫠 Here's what he learned from that experience.

The 3 elements of breakthrough startup ideas from Mike Maples, Jr Here's the full conversation: https://lnkd.in/g_jVaKSb

How close is AI to replacing product managers? Closer than I expected. In collaboration with Mike Taylor(a professional prompt engineer and co-author of the O'Reilly book "Prompt Engineering for Generative AI"), we've begun to develop a benchmark to track how good AI is at the most common and hardest PM tasks. In our first attempt, AI beat humans at 2/3 tasks, including developing a product strategy 😮 Check out our approach, and the surprising results https://lnkd.in/gCBYVqt9

Typical comment I'm getting about my episode with Mike Maples, Jr Here's the episode: https://lnkd.in/gPjw8RXk

Mike Maples, Jr is one of the most successful startup investors in history. He's worked with more early-stage startups than almost anyone alive, and with his fund, Floodgate, helped pioneer seed-stage investing as a category. He's been on the Forbes Midas List eight times and has made early bets on transformative companies like Twitter, Lyft, Twitch, and Okta. In his new book (coming out this Tuesday!), Pattern Breakers: Why Some Start-Ups Change the Future, he shares the three common elements he's uncovered that separate startups (and founders) that break through and change the world from those that don’t. This research is rooted in his decades of notes, decks, and founder relationships, and is unlike anything I've seen elsewhere. In our conversation, Mike shares: 🔸 The three elements of breakthrough startup ideas 🔸 The importance of founder disagreeableness 🔸 Why you need to both *think* and *act* differently 🔸 How to avoid the “comparison trap” and “conformity trap” 🔸 How to apply pattern-breaking principles within large companies 🔸 Mike’s one piece of advice for founders 🔸 Much more Listen now 👇 - YouTube: https://lnkd.in/gPjw8RXk - Spotify: https://lnkd.in/gAUbgGxz - Apple: https://lnkd.in/g6t367uY Some key takeaways: 1. Get out of the present: Instead of just thinking about solving current problems, you need to immerse yourself in the future. Look for emerging trends, technologies, or shifts in behavior that suggest where the world is heading. Great innovations often stem from individuals who immerse themselves deeply in a niche or cutting-edge area. 2. Great startup ideas share three elements: a. Inflections: External shifts that create potential for radical change in how people think, feel, and behave. b. Insights: A unique understanding of how to harness these inflections and enable a future that the company believes in. c. Founder-future fit: An alignment between the founders and the future they envision, including their skills, motivations, and network. 3. Three things that successful founders do differently: a. Movements: A movement aligns early believers around a higher purpose, leveraging their emotional commitment rather than just pragmatic benefits. b. Storytelling: Frame your startup’s story as a hero’s journey. Position yourself not as the hero but as the guide (like Obi-Wan Kenobi) who invites customers (the heroes) to embark on a transformative journey toward a better future. Tailor your narrative to resonate with different stakeholders—investors, customers, employees—by emphasizing how they can achieve their aspirations through your vision. c. Disagreeableness: Founders who challenge the status quo often appear disagreeable because they defy conventional norms. They drive change by questioning existing patterns and persuading others to embrace new ways of thinking and acting.