6. What percentage of the company are those XX,000 shares you're giving me?
7. What's the current valuation of the company?
8. How much runway do you have left? (Although you can probably infer this pretty easily by when they last raised.)
9. Since you're giving me a YY% haircut on my market-rate salary, what reasons other than the almost certainly worthless, say, 0.25% of the company you're giving me over four years should I be joining you?
10. I don't believe 60-80 hour weeks are productive, sustainable or healthy. What do you think about that?
#7 is a good question, but don't expect a tangible answer -- unless they just closed a round yesterday, it's truly impossible to say. That said, it's still a great question to ask to see how they value themselves, and what they feel potential acquirers or the public market would value them at.
#9 - I think that's a good question, though might be more diplomatically phrased. ;) (That said, be aware that "market rate" is extremely hard to pin down: for the same reasons you should expect an ambiguous answer to #7, your own "market rate" is similarly ambiguous.)
#10 - Agreed. I target 50, personally.
But even with the ambiguity, I expect the answers would still be enlightening.
It's been my experience that very few people "quit." Separations from startups tend to be very neutral, leaving it ambiguous whether someone quit or was let go. It's not hard to read between the lines, but discussions about this are not very up-front.
One reason to avoid these kinds of questions is because they can appear aggressive and people may not want to work with someone who is so up front on something that may or may not actually determine how well they can do their job, though obviously, churn can affect the over all work environment so it's good to know, but I think for most startups with <100 people you can easily figure this out on your own.
> "How many people do you hire in a typical month?"
Is there such a thing as a "typical month" in a startup? Isn't the definition of a startup that it's moving fast, things change and you have to roll with the punches?
> "Who was the last person to quit, and why?"
Good luck getting a real answer out of this question. They're not going to say that "he hated the atmosphere", or "the pay was too low". They're going to say something positive-sounding and completely bland. It tells you nothing about the company at all, unless they completely trash talk the person who just left.
> "When do you intend to raise money, and why?"
Again, you'll be lucky to get a real answer on this as well. If you get an "X months of runway before we need to raise again", there are a million assumptions built into that, and things change quickly. "Is the company primarily financed by selling product, or selling itself?" is probably a better question to ask.
> "Can I see where I’ll sit?"
Seriously? Again: it's a startup, things change. In the 2 weeks it might take you to start, the seating plan may have changed 3 times. Ask for a tour of the office, sure! Depending on the startup, it's unlikely that you'll be spending 2,000+ hours a year sitting at the same desk. Offices will move, things will be re-arranged, etc. Look at how the workspace is set up, to be sure; but asking something this specific seems like an odd request.
> "What do I want to do accomplish in my life, and how does this help me down that path?"
This one I agree with.
I actually like this question. You can tell a lot about a company by whether they're thinking about how to integrate new people. If they say, "We put new people right here next to Michelle for the first few weeks so she can show them the ropes," that's a pretty good sign. If they say, "We'll find something," that's a sign that they haven't really thought about what to do once they have somebody on board.
> How many people do you hire in a typical month?
1 per month? that seems low. Hiring is like everything else - subject to human cognitive biases. We all like to think that we can make the right decisions if we just put our minds to it, but the fact of the matter is a lot of it is just randomness. If I hired 4 people a month and I really fucked up on 3 of them I'd at least have 1 good employee left. That's a higher expected value than if I hired 1 person a month and screwed up just 5% of the time.
1) Have a p2p startup get acquired by Akamai
2) Want to do something financial
3) Financial == PCI compliance == super super expensive
4) Use p2p to build inexpensive PCI compliance