What are you making?
How does your product work in more detail?
Who needs what you’re making?
How do you know customers need what you’re making?
How will customers and/or users find out about you?
Where do your new users come from?
What makes new users try you?
Why do the reluctant users hold back?
Where is the rocket science here?
What is the next step in product evolution?
What’s new about what you make?
What are the top things users want?
What has surprised you about user behavior?
How are you understanding customer needs?
Who were your first customers?
How are you meeting customers?
How many people are in your target market?
How many $B is the market?
How fast is the market growing?
Who are your competitors? Who might become competitors?
Which competition do you fear most?
How many users do your competitors have?
How much are your competitors making?
How much time and money do users in your target market waste before switching to your product/service?
What are some trends in your target market, and related markets?
If your startup succeeds, what additional areas might you be able to expand into?
How do you think about your ASP (average selling price) over time? Do you think this will go up, down, or stay about the same? Why?
What could you do to expand your TAM?
How big is this market, really?
How do you know that this isn’t just for [subculture or niche user base]?
What is your growth like?
How many users do you have?
What is your user growth rate?
How many users have ever engaged?
What is your burn rate?
What’s the conversion rate?
What’s the repeat buyer rate?
What’s the churn rate?
How much does customer acquisition cost?
What is the average price of a [purchase, subscription, etc]?
How many users have ever engaged?
How many are currently active users?
Total revenue
Total costs, fixed and marginal
Acquisition funnel conversion rate
Customer acquisition cost
How many users are paying?
Are your customers one-and-done, or do they come back?
What are other ways people solve this problem?
What are your numbers? (to be elaborated into more questions)
Why haven’t you made more progress?
How will you make money?
Why is your product priced the way it is?
For marketplaces: why is your commission so high?
For marketplaces: why is your commission so low?
Why do you want to be part of YC?
What are you going to do next?
Would you relocate to Silicon Valley? (maybe not relevant anymore)
How long can you go before funding?
Will your team stick at this?
How do we know your team will stick together?
Are you open to changing your idea?
What’s the worst thing that happened?
What’s the biggest mistake you have made?
What problems/hurdles are you anticipating? How will you overcome them?
What will be the biggest challenge two years from now?
Who are your competitors?
Who do you fear the most?
What do you understand that others don’t?
Why isn’t someone already doing this?
How is your product different?
What, exactly, makes you different from existing options?
Who might become competitors?
What do you understand about your users?
What are the key things about your field that outsiders don’t understand?
Won’t [big company] just launch a [whatever your company does] feature and kill you?
Why did you pick this idea to work on?
Have you raised funding?
What’s the funniest thing that has happened to you?
Tell us something surprising you have done?
What’s an impressive thing you’ve done?
What systems have you hacked?
Will you reincorporate as a Delaware C-Corp?
What side of the marketplace is harder, demand or supply?
Is it harder to find suppliers to list [whatever good or service], or buyers to buy?
How do you plan to build the marketplace from scratch?
How would it work to expand geographically?
How do you all know each other?
Who are the other founders? (If you have <10% ownership founders)
Why did your team get together?
How did your team meet?
Who in your team does what?
Who would be your next hire?
Who would you hire or how would you add to your team?
Who is “the boss”?
What domain expertise do you have?
In what ways are you resourceful?
Author: John Sillings and few others