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Ask people who've lived it
Ask a quick question
I keep putting off the one email that would move my project forward
My instagram following has been stuck at 800 for two years and I don't know what moves the needle
My best friend and I haven't spoken in two months since our fight and neither of us has apologized
I replay the same conversation in my head for hours after it's over
What do I say when a customer wants a steep discount?
I have to let someone go tomorrow morning and I've never done this before
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.”
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.”
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.”
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.”
Kirsten on how AI changes what consumers buyTime 100 Most Influential People and dollar Shave Club sold for $1B.
Julian on using a system to curb phone distractions“I don't try to restart at full speed; I drop back to the mínimo viable version of each habit until the momentum returns, because a 20-minute workout and one focused block on the side project beats another day of zero.”
Alisa on growing from founder to CEO“The habits that made you a successful founder can become your biggest obstacles as CEO. Growth starts with seeing how others experience you.”
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.”
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.”
Nick on metabolic health, nutrition, and brain healthHarvard MD, Oxford PhD, Dartmouth valedictorian and #2 Science Bestseller on Substack.
Guillermo on building Vercel and Next.js“I want people to write these verification loops because it's gonna give me conviction in the product that it'll deliver to my customer.”
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.
Hal on keeping a morning routine alive after a bad night“I learned the hard way that my routine survives only when I make it so small that a bad day can't break it, like doing the 6-minute Miracle Morning instead of an hour.”
Roelof on what separates enduring companies from others“The enduring ones are willing to have what I call multiple founding moments. We have a wall at Sequoia that says, 'We're only as good as our next investment.' You have to stay paranoid. Never get crater-lazy.”
Matthew on finding the right partner“You want to be happy enough that the right thing doesn’t become your everything.”
Keith on spotting founders nobody has noticed yet“Stop looking at résumés the way Google does.”
Moses on making it to the top when you started with nothing“I had love for the game, parents who kept me grounded, and a city that taught me how to compete. What kept me going was consistency and curiosity. You control what you can control, stack good days, and let the game reward you when it's time.”
Ask about real life
I’m speaking at our company offsite tomorrow, and people are expecting another inspiring speech even though last quarter’s promises weren’t kept
I'm 41 and just moved for work. My only friends now are my spouse's coworkers. I tried two meetup groups but never went back after the first session. How do I turn one good conversation into a friendship?
We’ve interviewed 30 potential customers who all called our idea valuable, but none has agreed to pay for the prototype
My 15 year old son used to tell me everything. Since he started dating his girlfriend six months ago, he barely looks up from his phone when I talk to him. I don't know if this is normal or if I'm losing him
More on Delphi
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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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Go beyond reading or watching. Ask their Delphi a question, bring your own context, and follow the ideas that matter to you.
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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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