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Entrepreneurship Would You Rather Questions
Challenging Would You Rather questions about startups, investment decisions, building in public, and founder dilemmas.
- 1.Would you rather remote team issue or office culture clash?Rate this question
- 2.Would you rather secure big vc round but no product or have early users paying for your idea?Rate this question
- 3.Would you rather sell your startup for $5m now or keep building with a chance at $100m in 5 years?Rate this question
- 4.Would you rather pivot your entire business based on user feedback or stick to your original vision no matter what?Rate this question
- 5.Would you rather focus only on product for a year or focus only on marketing for a year?Rate this question
- 6.Would you rather launch with a terrible name you can change later or delay launch until you find the perfect name?Rate this question
- 7.Would you rather have 1000 users who love your product or 100,000 users who think it's okay?Rate this question
- 8.Would you rather copy a successful competitor's model or try something completely new and unproven?Rate this question
- 9.Would you rather work on your startup full-time with no income or keep your day job and work on it part-time?Rate this question
- 10.Would you rather share your revenue numbers publicly every month or keep all financial data completely private?Rate this question
- 11.Would you rather tweet about your failures and mistakes or only share your wins and successes?Rate this question
- 12.Would you rather open-source your entire codebase or keep your code proprietary?Rate this question
- 13.Would you rather share your product roadmap publicly or keep your plans secret from competitors?Rate this question
- 14.Would you rather respond to every critic on social media or ignore all negative comments completely?Rate this question
- 15.Would you rather livestream your coding sessions or work in complete silence and privacy?Rate this question
- 16.Would you rather share your startup costs breakdown publicly or keep your burn rate private?Rate this question
- 17.Would you rather announce features before building them or only announce features after they ship?Rate this question
- 18.Would you rather build an audience first then the product or build the product first then find customers?Rate this question
- 19.Would you rather take money from angel investors you like or take money from a famous VC firm you don't connect with?Rate this question
- 20.Would you rather bootstrap your startup and own 100% or raise VC funding and own 20%?Rate this question
- 21.Would you rather have one big customer that pays 80% of revenue or have 100 small customers?Rate this question
- 22.Would you rather pursue profitability from day one or pursue growth at all costs and worry about profit later?Rate this question
- 23.Would you rather sell your startup for $5M now or keep building with a chance at $100M in 5 years?Rate this question
- 24.Would you rather join an accelerator and give up 7% equity or figure everything out on your own?Rate this question
- 25.Would you rather raise a $10M Series A with aggressive growth targets or stay small and profitable with no outside pressure?Rate this question
- 26.Would you rather have investors who give great advice but want weekly updates or have hands-off investors who never help?Rate this question
- 27.Would you rather grow 10% month-over-month for 2 years or grow 100% once and then plateau?Rate this question
- 28.Would you rather fire an underperforming co-founder who is your friend or keep them and risk the company?Rate this question
- 29.Would you rather fix technical debt for 3 months or ship 3 new features customers are asking for?Rate this question
- 30.Would you rather fire a toxic high performer or keep them because they deliver results?Rate this question
- 31.Would you rather build what customers are asking for or build what you believe they need?Rate this question
- 32.Would you rather admit a major mistake publicly or fix it quietly and hope no one notices?Rate this question
- 33.Would you rather have a co-founder who disagrees with you often or a co-founder who always agrees with everything?Rate this question
- 34.Would you rather spend $50K on lawyers to protect your IP or risk someone copying your idea?Rate this question
- 35.Would you rather negotiate hard and lose a deal or accept bad terms to close the deal?Rate this question
- 36.Would you rather tell your team about runway problems early or protect them from stress until you have a solution?Rate this question
- 37.Would you rather give up 30% equity for $1M in funding or grow slowly with just your savings?Rate this question
- 38.Would you rather build your MVP in one weekend with bugs or spend 6 months building it perfectly?Rate this question
- 39.Would you rather hire your first employee too early or wait too long and burn out?Rate this question