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Ask people who've lived it
Ask a quick question
I mess up once at work and suddenly I feel completely worthless
I moved to a new city at 34 and don't know how to make friends anymore
I'll read a page and realize I have no idea what it said
My best performer has been missing deadlines for two months straight
My shoulder's been aching for a week but I don't want to lose my lifting streak
I keep starting things at midnight because that's the only time I feel pressure to finish
Ask the experts
Nir on why we reach for our phones without deciding to“Your brain has learned that opening social media relieves a quick pang of boredom, loneliness, or uncertainty, so it now cues the habit before you consciously decide.”
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.”
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.”
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.”
Kit on cutting a huge to-do list to three big things“I used to write forty-item lists and call it ambition, but it was just avoidance dressed as hard work.”
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.”
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.”
Vinod on which jobs AI will replaceLed KV's first OpenAI investment and juniper Networks: 2,500x return.
Aaron on fixing outbound when replies dry upPredictable Revenue, half a million copies and salesforce outbound system added $100M recurring revenue.
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.”
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.”
Kathryn on negotiating higher pay and getting it“I watched my own mom retire dramatically underpaid after 30 years, so I teach women to frame the ask around what they’ve already delivered and what they’ll deliver next, not just what they need.”
Deena on raising venture money as an underestimated founder“Do your homework on who you're pitching. Most founders spray and pray, but that wastes everyone's time. And bring your full self to the conversation. The intersectional, the immigrant, the nontraditional founder, those backgrounds are not weaknesses. They're edges. The data shows diverse founding teams build better businesses. But you have to own it.”
Nyree on why you crash at 2 p.m. after a full night's sleep“Eight hours in bed means nothing if your brain never entered deep restorative sleep, and by 2 p.m. your adenosine tank is still full from incomplete overnight clearance.”
Jeffrey on why treating symptoms is the wrong place to start“Symptoms are late signals, not first causes. In chronic illness the biology starts drifting years before a diagnosis. If you start at the symptom, you are downstream. You may mute the alarm without finding the fire. The body is a network, so ask what shifted in the person's story and physiology that made the symptom possible, then address that.”
Matthew on finding the right partner“You want to be happy enough that the right thing doesn’t become your everything.”
Andrej on how far we are from AGILed Tesla Autopilot computer vision team and founding member of OpenAI.
Sam on scaling a sales team fastPartner at Founders Fund and brex CRO, sub-$1M to 9-figure ARR.
Ask about real life
My company filed for an IPO and the lockup ends in six months. My vested shares are worth more than I'll earn in the next five years. How much do I sell on day one?
I'm 34, make $68,000, and just started putting money away for the first time. My company matches 4% on my 401k but I also want to save for a house in three years. I don't know how to split what's left between the two
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
I've had the same job, same apartment, same weekend routine for four years. Nothing's wrong exactly, but I realized last week I couldn't remember the last time I tried something new. Is this what being stuck feels like?
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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