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