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Entrepreneurship Would You Rather

Challenging Would You Rather questions for founders and entrepreneurs.

Startup Dilemmas

  1. 1.Would you rather bootstrap your startup and own 100% or raise VC funding and own 20%?
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  2. 2.Would you rather build your MVP in one weekend with bugs or spend 6 months building it perfectly?
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  3. 3.Would you rather hire your first employee too early or wait too long and burn out?
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  4. 4.Would you rather pivot your entire business based on user feedback or stick to your original vision no matter what?
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  5. 5.Would you rather focus only on product for a year or focus only on marketing for a year?
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  6. 6.Would you rather launch with a terrible name you can change later or delay launch until you find the perfect name?
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  7. 7.Would you rather have 1000 users who love your product or 100,000 users who think it's okay?
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  8. 8.Would you rather copy a successful competitor's model or try something completely new and unproven?
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  9. 9.Would you rather work on your startup full-time with no income or keep your day job and work on it part-time?
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Build in Public

  1. 1.Would you rather share your revenue numbers publicly every month or keep all financial data completely private?
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  2. 2.Would you rather tweet about your failures and mistakes or only share your wins and successes?
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  3. 3.Would you rather open-source your entire codebase or keep your code proprietary?
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  4. 4.Would you rather share your product roadmap publicly or keep your plans secret from competitors?
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  5. 5.Would you rather respond to every critic on social media or ignore all negative comments completely?
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  6. 6.Would you rather livestream your coding sessions or work in complete silence and privacy?
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  7. 7.Would you rather share your startup costs breakdown publicly or keep your burn rate private?
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  8. 8.Would you rather announce features before building them or only announce features after they ship?
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  9. 9.Would you rather build an audience first then the product or build the product first then find customers?
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Investment & Growth

  1. 1.Would you rather take money from angel investors you like or take money from a famous VC firm you don't connect with?
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  2. 2.Would you rather give up 30% equity for $1M in funding or grow slowly with just your savings?
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  3. 3.Would you rather have one big customer that pays 80% of revenue or have 100 small customers?
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  4. 4.Would you rather pursue profitability from day one or pursue growth at all costs and worry about profit later?
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  5. 5.Would you rather sell your startup for $5M now or keep building with a chance at $100M in 5 years?
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  6. 6.Would you rather join an accelerator and give up 7% equity or figure everything out on your own?
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  7. 7.Would you rather raise a $10M Series A with aggressive growth targets or stay small and profitable with no outside pressure?
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  8. 8.Would you rather have investors who give great advice but want weekly updates or have hands-off investors who never help?
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  9. 9.Would you rather grow 10% month-over-month for 2 years or grow 100% once and then plateau?
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Problem Solving & Conflict

  1. 1.Would you rather fire an underperforming co-founder who is your friend or keep them and risk the company?
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  2. 2.Would you rather fix technical debt for 3 months or ship 3 new features customers are asking for?
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  3. 3.Would you rather fire a toxic high performer or keep them because they deliver results?
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  4. 4.Would you rather build what customers are asking for or build what you believe they need?
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  5. 5.Would you rather admit a major mistake publicly or fix it quietly and hope no one notices?
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  6. 6.Would you rather have a co-founder who disagrees with you often or a co-founder who always agrees with everything?
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  7. 7.Would you rather spend $50K on lawyers to protect your IP or risk someone copying your idea?
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  8. 8.Would you rather negotiate hard and lose a deal or accept bad terms to close the deal?
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  9. 9.Would you rather tell your team about runway problems early or protect them from stress until you have a solution?
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How to Use These Questions

These Would You Rather questions work great for exploring startup values.

  1. Use at founder meetups as icebreakers
  2. Discuss with potential co-founders to test compatibility

Pro Tips:

  • There are no right answers - these reveal values and priorities

Why These Questions Matter

Test Co-Founder Alignment

Discover if you share the same values.

Prepare for Real Decisions

These hypotheticals often become real choices.