THE QUESTION ARCHIVE
Every question we've put to the room.
Pick one you've lived. Answer it in a piece. Your reply becomes a permanent, SEO-indexed page on your author profile.
QUESTIONS
- 20 Apr 2026Ask the room: what's the best thing you paid for this year that was worth 10x what it cost?Could be tool, service, consultant, advisor, trip. Share where the value came from.Answer this →
- 20 Apr 2026Ask the room: if you could hire only one more person this year, what role and why?Be specific. Not a title — the actual problem they'd solve.Answer this →
- 20 Apr 2026Ask the room: what's the one phrase that describes your company's working style?One line. In the comments.Answer this →
- 20 Apr 2026Ask the room: what subscription or tool would you cancel today if you had the nerve?The one you're still paying for out of inertia.Answer this →
- 20 Apr 2026What metric did you obsess over that turned out not to matter?And what metric should have had that obsession instead.Answer this →
- 20 Apr 2026What did the first hire you made teach you about yourself?Name the hire, name the lesson, name what you do differently now.Answer this →
- 20 Apr 2026Describe the weekend you knew the company would survive.The concrete moment. Who was in the room, what was happening.Answer this →
- 20 Apr 2026Name a product feature that saved the company. What made it work?The ship, the customer response, the metric that moved.Answer this →
- 20 Apr 2026What did you give up personally to make the business work?Not martyrdom — the real trade and whether it was worth it.Answer this →
- 20 Apr 2026How do you know when you're building the wrong thing?The specific signal you watch for. The time you missed it.Answer this →
- 20 Apr 2026What decision were you making at 3am that you'd never make in daylight?And what that tells you about your decision-making system.Answer this →
- 20 Apr 2026Describe the first customer who paid you more than your rent.The deal, the conversation, what it changed.Answer this →
- 20 Apr 2026What's a piece of conventional business advice that's wrong for your company?And what the right advice is — specific to your shape.Answer this →
- 20 Apr 2026Write about a competitor you respected more than you admitted out loud.What they did better. What you learned from watching them.Answer this →
- 20 Apr 2026Ask the room: what piece of advice do you wish someone had given you in year one?One line answers welcome. Leave it in the comments of the piece.Answer this →
- 20 Apr 2026Describe a hire that was wrong from the start — what did you miss?The signal you ignored. Useful if you can name it.Answer this →
- 20 Apr 2026What's a habit that made you a better operator?Not productivity p0rn. One thing that moved something that matters.Answer this →
- 20 Apr 2026Write about the meeting you dread most. What would you change?Monday all-hands, 1:1, board prep — whichever. The real one.Answer this →
- 20 Apr 2026What did the first customer you lost teach you?Name the churn. What you thought the reason was vs what it actually was.Answer this →
- 20 Apr 2026What did raising your first round actually cost you?Not the dilution — the thing people don't talk about.Answer this →
- 20 Apr 2026What's the hardest part of running a company that no one warned you about?Specific and personal beats general.Answer this →
TOPICS IN MOTION
- 20 Apr 2026This week: product-market fitThe moment the pull started. The signal you'd missed. The numbers that moved.See the pieces →
- 20 Apr 2026This week: first customerThe first paying customer. The deal, the pricing, what it told you about the business.See the pieces →
- 20 Apr 2026This week: fundraisingEntrepreneurs on what their round actually cost them, what they wish they'd done, and the conversation they remember.See the pieces →
- 20 Apr 2026This week: retentionChurn is a teacher. Pieces on keeping the customers you already have.See the pieces →
- 20 Apr 2026This week: hiringThe hires that worked, the hires that didn't, the signals people missed.See the pieces →
- 20 Apr 2026This week: pricingEntrepreneurs writing about price changes, positioning, and what surprised them.See the pieces →
QUOTES WORTH SITTING WITH
- Patience is the hidden edge., Charlie Munger
- Speed is a habit. Once you have it, everything else is easier., Brian Chesky
- You don't rise to the level of your goals. You fall to the level of your systems., James Clear
- Hire people smarter than you. Then get out of their way., Lee Iacocca
- Your brand is what other people say about you when you're not in the room., Jeff Bezos
- Strategy is choosing what not to do., Michael Porter
- Quality is remembered long after the price is forgotten., Aldo Gucci
- Don't find customers for your products. Find products for your customers., Seth Godin
- Stay close to the customer. That's where the business is., Indra Nooyi
- Early on, speed is a better strategy than precision., Reid Hoffman
- Focus on the numbers that matter. Everything else is noise., Elad Gil
- The best founders are the ones who refuse to quit., Ron Conway
- Revenue is vanity. Profit is sanity. Cash is reality., Pehr G. Gyllenhammar
- Nothing great was ever achieved without enthusiasm., Ralph Waldo Emerson
- Chase the vision, not the money — the money will follow., Tony Hsieh
- The best product wins, but only if you let people find it., April Dunford
- If you're not solving a problem that someone will pay for, you don't have a company., Jason Lemkin
- Build what you wish existed., Austin Kleon
- The price you pay for avoiding conflict is an average team., Kim Scott
- The most underrated skill in business is the ability to sit still and think., Morgan Housel
- Move fast and fix things., Mark Zuckerberg
- The riskiest thing is to take no risks., Mark Zuckerberg
- A company's most valuable asset is its culture., Ben Horowitz
- Take care of the team, and the team will take care of the work., Richard Branson
- You can't shrink your way to greatness., Tom Peters
- Fall in love with the problem, not the solution., Uri Levine
- Speed is the ultimate weapon in business., Andy Grove
- Only the paranoid survive., Andy Grove
- The best way to predict the future is to invent it., Alan Kay
- Great things in business are never done by one person., Steve Jobs
- Don't be afraid to give up the good to go for the great., John D. Rockefeller
- Opportunities don't happen. You create them., Chris Grosser
- The first rule is to keep an untroubled spirit. The second is to look things in the face and know them for what they are., Marcus Aurelius
- If you double the number of experiments you do per year, you're going to double your inventiveness., Jeff Bezos
- Every no gets me closer to a yes., Mark Cuban
- The standard you walk past is the standard you accept., David Morrison
- Survival is a key metric. Be here in ten years., Sam Altman
- The top 10% of anything is where the compounding lives., Naval Ravikant
- It's not about money. It's about leverage., Naval Ravikant
- Ideas are easy. Execution is everything., John Doerr
- The day before something is a breakthrough, it's a crazy idea., Peter Thiel
- Culture eats strategy for breakfast., Peter Drucker
- Your margin is my opportunity., Jeff Bezos
- Be so good they can't ignore you., Steve Martin
- Start with one customer. Solve one problem. Compound., April Dunford
- If you're not embarrassed by the first version of your product, you've launched too late., Reid Hoffman
- Do things that don't scale., Paul Graham
- Make something people want., Paul Graham