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My best performer has been missing deadlines for two months straight
I'm seeing my first patient on my own and I'm scared I'll miss something important
My client wants a discount before signing but I'm scared saying no kills the deal
I want to break into a friend group at work but I don't know how to start
Ask the experts
Lorraine on getting noticed for your work“Doing great work doesn’t guarantee recognition. Make your impact easy to explain so people can advocate for you when you’re not in the room.”
Guillermo on building Vercel and Next.js“The best things we've done for our brand is the things that we did without thinking we're working on our brand.”
Alastair on handling a teammate who undermines you in meetings“I would name the pattern in private first: I noticed you agreed in the room, then raised concerns afterwards. If you disagree, raise it in the meeting so we can deal with it straight away.”
Peter on which AI tools are worth paying forLed product teams at Meta, Amazon, Roblox and reddit product 0 to 1M+ users.
Céline on protecting your health in a noisy information world“I protect my health the same way I protect my patients: by curating my information diet the way I curate my food. I go to the source, I follow people who've been right before and correct themselves when the evidence changes, and I stay open to changing my mind. Certainty that cannot bend is not strength; it is a vulnerability.”
Jason on when to keep fighting and when to wind down“I’ve seen this movie too many times: four months of runway with flat sales usually means the founder never found a repeatable motion, not that the market said no.”
Peter on taking back your evenings from your phone“I stopped checking messages after 6 pm and told my team to call twice if it was truly urgent; nothing broke, and I got ten hours back every week.”
Brian on scaling a company“The leadership style that gets you to ten employees won’t get you to a thousand. Your company can’t evolve unless you do.”
Spencer on life inside an NBA organization“I used to think pushing past your body meant toughness, but the league taught me that the hardest skill is staying on the floor.”
Pedro on where machine learning is headed“The same basic paradigms have been used since the 1950s. At the end of the day, we’re going to need some new ideas.”
Matthew on finding the right partner“You want to be happy enough that the right thing doesn’t become your everything.”
Lenny on breaking into product management“A few paths actually work. The safest is transitioning internally, partnering closely with a PM until you can make the case. The second is joining an early-stage startup where everyone does everything. Regardless of path, become the person who deeply understands the customer and can translate that into product insight.”
Vinod on which jobs AI will replaceLed KV's first OpenAI investment and juniper Networks: 2,500x return.
Nir on the science of living longer“To delay the biology of aging, we don't prevent just one disease, we prevent many of them. We used to think each age-related disease was separate, but they share common roots. Longevity becomes a side effect of staying healthy longer.”
Michael on building for the long term“You can’t build your future around protecting your past. Stay close to customers, keep learning, and be willing to reinvent the business.”
Jessi on deciding what comes first when everything is urgent“I learned in hospice that when everything feels urgent, the first thing is to steady my own nervous system so I can see what is actually life-or-death and what only feels that way.”
Grant on growing an AI startup“When growth stalls, doing more of the same won’t save you. Sometimes your small team needs to make one bigger bet.”
Jim on enjoying competition when teammates are more intense“I stopped enjoying baseball when I was chasing what everyone else valued, and I found my game again only when I started competing to raise my own level, not to beat theirs.”
Vanessa on sexual expectations couples never say out loud“I don't believe in a universal normal for any stage, but I do think it's completely natural for that early honeymoon frequency to taper off after about a year.”
Suzanne on what happens behind closed doors in a layoff“I've personally been involved in laying off well over a thousand people, and the part no one talks about is how fast the dignity gets stripped away: one minute you're trusted, the next a manager you've never met is reading you a script while someone cuts your computer access.”
Ask about real life
My design studio has had the same name and logo since I started it nine years ago. A client recently said our brand looks stuck in 2015. Revenue is fine, but I keep wondering if I'm bleeding new clients because of how we look. Is that a good enough reason to rebrand?
My coworker turned $3,000 into $40,000 on a single stock last year and now I keep looking at nvidia every night before bed. I have $5,000 sitting in cash and no idea if I'm buying in at the top or missing out for good. Is it too late to get in?
I've lost and gained the same 20 pounds three times in five years. Every photo from a friend's wedding last month, I picked myself apart before anyone else could see it. I know the number on the scale isn't the problem. What changes how someone sees their own body?
There are three of us starting this company: two of us quit our jobs to work on it full-time, one is staying at his job and advising on weekends. We're trying to decide if he still deserves an equal third of the equity. Whatever we agree on now, we'll be stuck with for years
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Top perspectives
Top perspectivesWriter of Lenny's Newsletter · Host of Lenny's Podcast · ex-Airbnb
“The honest answer: if you're not sure, you probably don't have it yet. When you truly have product-market fit, people are fighting to get in. You're not questioning it.”
Co-founder of Sundial · ex-VP Design at Facebook
“The clearest signal is retention: are the people who try your product coming back without you having to push them? If they are, you likely have product-market fit for a segment. If they aren't, the rest is noise.”
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Their Delphi, answering in their voice
I'm a solo founder and I honestly can't tell if I have product-market fit yet.
If you're not sure, you probably don't have it yet. When you do, people are fighting to get in. Start with the Sean Ellis “very disappointed” survey and look hard at retention. Those two give you the clearest read.
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