Tactical thoughts on how to approach common and difficult questions.
▶ How much are you raising?
▶ You're raising at an $xx cap? How did you come up with that number?
▶ Why are you only raising $xM? That seems like not enough to get you to your Series A, and it may not be a big enough round for a fund of our size.
▶ Do you have any questions for us?
▶ Who else has invested? What's the status on your round / fundraise?
▶ Are you looking for (or do you have) a lead investor?
▶ What are your financial projections?
▶ Who are your previous investors?
▶ Who else (what other investors) are you talking to?
▶ Can I see your cap table?
▶ What are you looking for in a partner?
▶ What is your market size?
▶ How do you think about defensibility / why can't your competitors copy this?
▶ What's your moat?
▶ What questions should I have asked you that I didn't?
▶ How are you different than [competitor name]?
▶ Tell me about your competitive landscape.
▶ What's your GTM strategy?
▶ How are you thinking about spending the money you raise (and how this will affect your burn)? How long will it last you? What hires are you planning to make first?
▶ Why are you a solo founder?
▶ What are the biggest challenges you expect to have in the future? What would be a reason you may not succeed in building a billion $ business? If you fail, what will be the main reason?
▶ What keeps you up at night?
▶ What's your short term product roadmap look like, and what does the product look like 5-10 years from now?
▶ What is the top reason customers say no to buying your product?
Once you’ve got interest from investors, how do you pick the right one? Here are some thoughts on that.
Sources A good bit of what I learned came from writings and talks from Pear and YC . It only clicked after I made mistakes though, the hard way is sometimes the only way you can learn some things.