Back to HomeEntrepreneurship Would You Rather Questions
Challenging Would You Rather questions about startups, investment decisions, building in public, and founder dilemmas.
A) secure big vc round but no product B) have early users paying for your idea
A) tweet about your failures and mistakes B) only share your wins and successes
A) join as early engineer B) join as early designer
A) sell product to 500 users B) secure seed funding now
A) negotiate hard and lose a deal B) accept bad terms to close the deal
A) join an accelerator and give up 7% equity B) figure everything out on your own
A) launch mvp and seek funding B) bootstrap and grow slowly
A) spend 12 hours debugging B) cancel the product launch entirely
A) spend $50K on lawyers to protect your IP B) risk someone copying your idea
A) grow 10% month-over-month for 2 years B) grow 100% once and then plateau
A) give up 30% equity for $1M in funding B) grow slowly with just your savings
A) sell your startup for $5M now B) keep building with a chance at $100M in 5 years
A) build what customers are asking for B) build what you believe they need
A) take money from angel investors you like B) take money from a famous VC firm you don't connect with
A) pivot to a new market B) cut the team by 50%
A) secure seed funding quickly B) pivot to a new idea and raise again
A) admit a major mistake publicly B) fix it quietly and hope no one notices
A) have one big customer that pays 80% of revenue B) have 100 small customers
A) pursue profitability from day one B) pursue growth at all costs and worry about profit later
A) work on your startup full-time with no income B) keep your day job and work on it part-time
A) have 1000 users who love your product B) 100,000 users who think it's okay
A) livestream your coding sessions B) work in complete silence and privacy
A) launch with a terrible name you can change later B) delay launch until you find the perfect name
A) bootstrap your startup and own 100% B) raise VC funding and own 20%
A) raise a $10M Series A with aggressive growth targets B) stay small and profitable with no outside pressure
A) copy a successful competitor's model B) try something completely new and unproven
A) announce features before building them B) only announce features after they ship
A) respond to every critic on social media B) ignore all negative comments completely
A) secure $500k investment B) accept a $1 million acquisition offer
A) build an audience first then the product B) build the product first then find customers
A) pivot your entire business based on user feedback B) stick to your original vision no matter what
A) have a co-founder who disagrees with you often B) a co-founder who always agrees with everything
A) fix technical debt for 3 months B) ship 3 new features customers are asking for
A) open-source your entire codebase B) keep your code proprietary
A) tell your team about runway problems early B) protect them from stress until you have a solution
A) build your MVP in one weekend with bugs B) spend 6 months building it perfectly
A) have investors who give great advice but want weekly updates B) have hands-off investors who never help
A) share your revenue numbers publicly every month B) keep all financial data completely private
A) fire a toxic high performer B) keep them because they deliver results
A) fire an underperforming co-founder who is your friend B) keep them and risk the company
A) share your product roadmap publicly B) keep your plans secret from competitors
A) hire your first employee too early B) wait too long and burn out
A) share your startup costs breakdown publicly B) keep your burn rate private
A) focus only on product for a year B) focus only on marketing for a year