
Need good interview questions for startup founders - y2002
I'm interviewing a lot of startup ceo/founders in the next few weeks for my website.  What are some great/insightful/funny startup questions you wish people would ask you?
======
trekker7
If someone paid you $1 billion right now, with the condition that you could
never work a day in your life again, and never start a company, would you do
it?

Edit: rms is right. How about "If someone paid you $1 billion with the
condition that you could never do _anything productive_ ever again, and
basically had to live a playboy's life forever, would you do it?"

~~~
rms
I think that's an easy question, as long as a non-profit doesn't count as work
or a company.

Edit: Revised question is really interesting. I don't know what my answer
would be.

~~~
diego
My answer would be a resounding no. Some things just cannot be bought.
Everyone knows what things they would never do regardless of the money
involved. If I could not do anything productive ever again, I'd be depressed.

Also, I think there is such thing as too much money. In terms of happiness,
money provides diminishing returns. I believe that having enough to not worry
about having to generate income is a good goal for most people. Beyond that,
it can create a feeling of alienation with regards to the rest of the
population, as you would be too far to the right on the wealth distribution
curve and would have few peers. What do you get in return? Fame (if you want
it) and access to extravagant toys. The real problems in life remain the same
whether you have 10M or 1B: you will get old, you may have family or health
problems, accidents happen, etc.

Alienation + productivity ban = sad life. No thanks.

~~~
swombat
Ditto. "Productive" is such a loose term. The question basically boils down to
"would you take a billion dollars along with an interdiction from trying hard
at anything that you think you might enjoy doing?"

Definitely no.

------
samratjp
The thing is that technology is only a means, so ask a real question such as:

What "can" you design under $1 that solves a major problem in the world?

Example answer: packets of salt and sugar is all it takes to prevent/solve
dehydration in many sub-saharan countries. Can it save the world? Yes. Is it
executable? Yes. Is the UI simple? Yes, ziplock sugar packets. Marketing
costs? evangelize.

Point is that the technical skills can be evaluated to a great accuracy more
or less, it is the real-time thinking skill that matters; i.e. it is extremely
ok to ask a question that demands considerable attention and problem-solving.
An ideal interviewee knows that a good answer is not a matter of complete
polarization, but careful articulation.

~~~
rms
How do salt/sugar solve dehydration?

~~~
plinkplonk
"How do salt/sugar solve dehydration?"

<http://en.wikipedia.org/wiki/Oral_rehydration_therapy>

------
DanielBMarkham
Okay. I have a few.

First question: why? You guys are smart/energetic/young/etc -- why do this?
Why not join BigCorp or become a priest or something?

Second question: What do you worry about the most? What keeps you up at night?

Third question: If you could only pick one thing to validate your reason for
forming a startup, what would it be? In other words, what would be the single
biggest indicator to you that you are doing the right thing?

------
skmurphy
1\. What have you learned?

2\. How have you changed since you started?

3\. What key skill or experience did you lack when you started that has caused
you the most problem?

4\. What has been the biggest surprise: what was one key assumption you made,
perhaps even unconsciously, that has caused the most grief?

5\. What development, event, or new understanding since you started has had
the most impact on your original plan? How has your plan changed in response?

~~~
skmurphy
We have a number of founder interviews up at
<http://www.skmurphy.com/blog/category/founder-story/>

I checked your profile but I can't determine your website, where will the
interviews be posted?

------
pierrefar
What was your biggest failure before starting up?

------
dusklight
If you had to choose between succeeding and finding the love of your life,
which would you choose and why?

------
itay
Things I am curious about:

1\. What made you first think that starting a company is right for you?

2\. Was there anyone/anything who inspired you to manage the company the way
you do, and to define the culture the company has?

3\. Was it obvious that the company needed to be in place X? If X is not in
Silicon Valley, why not? Do you think it was the right decision?

4\. Where is the best source of good people for you? What characteristics are
important for them to possess (good schools, lots of experience, dedication,
etc).

That's it for now. I'll add more if I think of any.

------
dkokelley
What stage are these founders in? Have they succeeded, are they on their way
there, are they just in a the planning stage? Different questions apply to
different stages.

~~~
y2002
These founders all have products at least in beta. They are in various stages
of funding: some are self-funded, some have angel investors, others have
institutional funding.

~~~
dkokelley
Ok then, my questions would be:

How much money do you think you'll make from this (to see how they evaluate
their chances and worth), do you want to sell or remain and make a salary (to
see what they are building the company for - longevity or a quick flip, not
that either are bad), and what do you see your retirement like?

------
luckystrike
In my opinion, the person should be clear why (s)he wants to do a startup.
Does the person aspire to (hopefully) earn a lot of money in a relatively
short time, or is it sheer satisfaction of doing your own thing or some other
valid reason?

It might be better if your core thinking and goals, match to some extent with
your probable co-founder.

Having said that, the 'skill set' of the person should compliment yours, so
that as a team you are able to achieve more.

------
vlad
Have you ever done/worked at a startup? I know you already prequalified your
interviewees, but I'd still ask that.

------
mattjung
How many iterations took it from the initial idea to the current product? How
did you get your first customers?

------
JacobAldridge
What did you decide not to do in order to focus on your startup?

When did the business model become clear for your business?

------
neilc
Which do you think is most important: the right market, the right product, or
the right team?

------
sgibat
What will you do if you fail?

------
paul9290
Did you consider yourself bipolar before or is this a new experience for you?

------
wheels
If your company tanked tomorrow, would the experience have been worth it?

