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Browse Entrepreneurship Would You Rather questions

Challenging Would You Rather questions about startups, investment decisions, building in public, and founder dilemmas.

74 questionsFree to playUpdated weekly

Showing 1–50 of 74

#1 · Would you rather
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A) bootstrap your startup and own 100% B) raise VC funding and own 20%
Good one?
#2 · Would you rather
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A) secure big vc round but no product B) have early users paying for your idea
Good one?
#3 · Would you rather
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A) tweet about your startup's failures and mistakes B) only share your wins and successes
Good one?
#4 · Would you rather
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A) join a startup as its first engineer B) join a startup as its first designer
Good one?
#5 · Would you rather
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A) sell product to 500 users B) secure seed funding now
Good one?
#6 · Would you rather
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A) give your investors a board seat and real control B) keep control and raise half as much money
Good one?
#7 · Would you rather
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A) have your startup on every tech podcast B) have ten customers who would never leave
Good one?
#8 · Would you rather
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A) grow your startup 10% month-over-month for 2 years B) grow it 100% once and then plateau
Good one?
#9 · Would you rather
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A) give up 30% equity for $1M in funding B) grow slowly with just your savings
Good one?
#10 · Would you rather
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A) take money from angel investors you like B) take money from a famous VC firm you don't connect with
Good one?
#11 · Would you rather
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A) spend your startup's last $40k on ads B) spend it on one senior engineer
Good one?
#12 · Would you rather
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A) have one big customer that pays 80% of revenue B) have 100 small customers
Good one?
#13 · Would you rather
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A) have your co-founder quit the week you raise B) have them stay and quietly check out
Good one?
#14 · Would you rather
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A) keep your company's headcount at five forever B) grow to two hundred and never know names
Good one?
#15 · Would you rather
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A) let your investors pick your next ceo B) stay ceo and stall the company's growth
Good one?
#16 · Would you rather
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A) hire your best friend into your startup B) hire a stranger who is twice as good
Good one?
#17 · Would you rather
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A) work on your startup full-time with no income B) keep your day job and work on it part-time
Good one?
#18 · Would you rather
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A) fire ten people at your startup in one morning B) cut everyone's pay and keep the team whole
Good one?
#19 · Would you rather
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A) livestream every coding session while you build your startup B) build it in complete silence and privacy
Good one?
#20 · Would you rather
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A) let your co-founder be the public face of the company B) take the spotlight and every angry email
Good one?
#21 · Would you rather
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A) work 80-hour weeks at your startup for two years B) work 40 and take ten years to get there
Good one?
#22 · Would you rather
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A) have a co-founder who ships fast and breaks things B) have one who ships perfect things slowly
Good one?
#23 · Would you rather
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A) raise a $10M Series A with aggressive growth targets B) stay small and profitable with no outside pressure
Good one?
#24 · Would you rather
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A) say no to your startup's biggest possible client B) say yes and become their in-house dev shop
Good one?
#25 · Would you rather
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A) copy a successful competitor's model B) try something completely new and unproven
Good one?
#26 · Would you rather
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A) build your company on a giant platform's api B) build it all yourself and ship two years late
Good one?
#27 · Would you rather
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A) respond to every critic of your startup on social media B) ignore all negative comments completely
Good one?
#28 · Would you rather
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A) have your startup's launch day break every server B) have a flawless launch nobody shows up to
Good one?
#29 · Would you rather
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A) secure $500k investment B) accept a $1 million acquisition offer
Good one?
#30 · Would you rather
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A) build an audience first then the product B) build the product first then find customers
Good one?
#31 · Would you rather
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A) pivot your entire business based on user feedback B) stick to your original vision no matter what
Good one?
#32 · Would you rather
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A) have a co-founder who disagrees with you often B) a co-founder who always agrees with everything
Good one?
#33 · Would you rather
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A) take a check from your investors' worst rival B) walk away and burn through your last month
Good one?
#34 · Would you rather
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A) keep your startup alive on consulting revenue B) kill it and go all-in on the next idea
Good one?
#35 · Would you rather
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A) fix technical debt for 3 months B) ship 3 new features customers are asking for
Good one?
#36 · Would you rather
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A) tell your team about runway problems early B) protect them from stress until you have a solution
Good one?
#37 · Would you rather
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A) double your startup's prices and lose half the users B) keep prices low and watch your margins vanish
Good one?
#38 · Would you rather
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A) have investors who give great advice but want weekly updates B) have hands-off investors who never help
Good one?
#39 · Would you rather
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A) take your startup public and answer to everyone B) stay private and never see a dollar of it
Good one?
#40 · Would you rather
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A) fire an underperforming co-founder who is your friend B) keep them and risk the company
Good one?
#41 · Would you rather
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A) hire your first employee too early B) wait too long and burn out
Good one?
#42 · Would you rather
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A) have investors who open every door but treat you badly B) have decent ones who can't open a single door
Good one?
#43 · Would you rather
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A) negotiate hard and lose a deal B) accept bad terms to close the deal
Good one?
#44 · Would you rather
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A) be the founder your team loves but investors doubt B) be one investors trust but the team fears
Good one?
#45 · Would you rather
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A) spend $50K on lawyers to protect your IP B) risk someone copying your idea
Good one?
#46 · Would you rather
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A) pay yourself nothing while your startup grows B) take a salary and slow the company down
Good one?
#47 · Would you rather
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A) sell your startup for $5M now B) keep building with a chance at $100M in 5 years
Good one?
#48 · Would you rather
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A) build what customers are asking for B) build what you believe they need
Good one?
#49 · Would you rather
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A) pivot to a new market B) cut the team by 50%
Good one?
#50 · Would you rather
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A) secure seed funding quickly B) pivot to a new idea and raise again
Good one?

About entrepreneurship dilemmas

Challenging Would You Rather questions about startups, investment decisions, building in public, and founder dilemmas. Every question below shows the live global split once you pick a side, so you can find out whether your take is genuinely rare or whether half the internet agrees with you. Nothing is behind a sign-up, and the questions are free to read out loud, print, or play on a big screen.

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