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Ask a quick question
My longtime client just renewed at the same plan and I want to pitch the premium tier without sounding greedy
I replay the same conversation in my head for hours after it's over
I have 200 happy customers but almost none of them leave a google review
I keep doing the work myself because asking my team feels like dumping on them
People keep asking if they can open a location like mine somewhere else
Everyone's talking about bitcoin and I want to know if I should buy in
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.”
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.”
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.”
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.”
Dharmesh on building products and company culture“Culture is how people make decisions when you’re not in the room. Be as deliberate about building it as you are about your product.”
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.”
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.”
Vinod on which jobs AI will replaceLed KV's first OpenAI investment and juniper Networks: 2,500x return.
Nick on metabolic health, nutrition, and brain healthHarvard MD, Oxford PhD, Dartmouth valedictorian and #2 Science Bestseller on Substack.
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.”
Matthew on finding the right partner“You want to be happy enough that the right thing doesn’t become your everything.”
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.”
Stanley on turning a scrappy experiment into a public company“We saw a macaroon shop in Palo Alto with orders they couldn't fulfill, so we built a static HTML site with a phone number and took orders by hand. The scrappy part isn't a phase you graduate from; it's a discipline. You automate after you understand the problem deeply, not before. Change everything except the mission if the data says so.”
Julie on becoming a better manager“Your job as a manager is to help other people do great work. Start by understanding what’s getting in their way.”
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.”
Kirsten on how AI changes what consumers buyTime 100 Most Influential People and dollar Shave Club sold for $1B.
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.”
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.”
Ask about real life
I'm 29, just paid off my loans, 80K saved and no idea what to do with it. Everyone has an opinion, index funds, real estate, crypto. Money was always stressful growing up, and I'm more scared of losing it than driven to grow it
Every time I rebuild my morning routine, one bad night's sleep knocks it out and I don't restart for weeks. The last one ran 11 days. I keep planning bigger ones. What would make a routine survive a bad day?
My boyfriend hasn't planned a single date in the two years we've been together. I book the trips, I make the reservations, I remember his mom's birthday. Last week I asked him to plan something, just once, and he said he'd think about it. He never brought it up again
I bring home $2,400 a month after rent and have $6,800 spread across three credit cards. Minimum payments alone eat almost $300 of that, and a collector called twice this week. I don't have room to snowball anything, so what do I cut first?
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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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