Questions to Ask About Entrepreneurship
Questions for talking with a founder about how their business actually started, how it is funded, what the job costs them, and what they would do differently. Useful if you are considering starting something yourself, joining early, or writing about someone who did.
The questions
Open any question for the note
How did you decide this was the problem worth spending years on?
Why ask it
Founders who lead with market size usually picked the problem after the fact. The ones who name a specific frustration they lived with picked it first. Listen for whether the story predates the company.
What were you doing before you started, and what made you leave?
Why ask it
The push out often matters more than the pull in. Leaving a job they liked suggests conviction. A layoff or a bad manager is a fine origin too, but it changes how much weight the founding story deserves.
What did the first ninety days actually look like?
Why ask it
Founders remember year one as a montage. Narrowing to ninety days forces detail: who they called, what they built, what they charged. Vagueness here often means someone else did the early work.
How did you find your first ten customers?
Why ask it
Naming them one by one is the test. Answers like word of mouth or a launch post can mean nobody ever learned to sell, which surfaces later when growth stalls and there is no repeatable motion to fall back on.
What do you know now about pricing that you got wrong at the start?
Why ask it
Pricing is the mistake founders admit most freely and remember most precisely. You will usually hear that they charged too little, and hear how long it took to raise it and who churned when they did.
How do you and your co-founder settle it when you disagree?
Why ask it
Every pair has a tiebreaker, whether it is written into the docs or not. If they cannot describe one, the disagreement is probably still live rather than resolved.
What does a normal week look like now compared with year one?
Why ask it
The contrast shows whether they built a company or a job. Weeks that look identical two years apart mean nothing has been handed off, and the business still stops when they stop.
How did you fund it, and would you raise the same way again?
Why ask it
Funding regret is specific: the terms, the timing, the investor they wish they had skipped. A founder who says they would do it identically has usually not run the dilution math.
What number do you check first thing in the morning?
Why ask it
The metric someone looks at unprompted is the one they actually manage by. If it is signups or follower count rather than revenue or retention, that tells you where their attention goes.
Which hire changed the company most, and which one did you get wrong?
Why ask it
Asking for both directions gets past the highlight reel. The bad hire usually produces the more useful answer: what they missed in the interview, and how many months they waited before acting.
What are you spending money on that you cannot fully justify yet?
Why ask it
This surfaces their real bets. Unjustified spend is either conviction or drift, and the way they explain it tells you which one you are looking at.
What have you decided not to do, even though you could have?
Why ask it
Focus is subtractive. Founders who cannot name a customer segment, a feature, or a market they turned down are usually saying yes to everything and calling it opportunity.
What is the part of this job nobody warned you about?
Why ask it
Gets past the standard line about long hours. The honest answers tend to be the isolation, the admin, or the endless work of chasing invoices that nobody describes as entrepreneurship.
How do you pay yourself, and how long did it take to get there?
Why ask it
Salary history is a plain measure of how tight things have been. Still taking nothing after several years says something about the business, not about their commitment.
What happened the closest you came to shutting it down?
Why ask it
Near-death stories are where the real decisions live: the payroll they nearly missed, the anchor customer who left. A founder who says there was never a close call is either very lucky or editing.
Which competitor do you actually worry about?
Why ask it
Founders who name one have usually lost deals to them and know why. Answers like nobody, we are creating a category often mean they have not asked buyers why they said no.
What would have to be true for you to sell the company?
Why ask it
A number and a timeline reveal their real horizon. Hesitation here often means the founders have never discussed it with each other, which becomes a problem the week an offer arrives.
How has running this changed what you are like to live with?
Why ask it
Moves the conversation from the company to the person. Answers about a partner's patience or the birthdays missed are the cost accounting founders rarely volunteer on a panel.
Starting over tomorrow with what you know now, what would you change about the first year?
Why ask it
Broad enough to get the lesson they most want to pass on, specific enough that they cannot fall back on generic advice about hiring slowly and firing fast.
What would you tell someone about to quit their job to do this?
Why ask it
Whatever they emphasize first, runway, a partner's income, health insurance, is the risk that actually kept them awake. It is often nothing like the risk the listener is worried about.
How to use these questions
Practical guidance for the conversation itself
Getting past the pitch
Ask for dates and numbers
Founders have a rehearsed version of their story. Asking when something happened, how much it cost, or how many customers there were at the time breaks the script, because the rehearsed version rarely carries specifics.
Ask about the thing that did not work
Failures are usually described more honestly than successes, partly because there is less incentive to tidy them up. The abandoned product line will teach you more than the one that worked.
Say why you are asking
A founder answers a curious stranger differently than someone weighing up the same leap. If you are considering starting something, say so early. You will get warnings instead of highlights.
Leave the personal questions until later
The questions about pay, near-failure, and family strain land badly cold. Put them after twenty minutes of business talk, once it is clear you are not collecting a cautionary tale.
What tends to go wrong
Treating survivors as a representative sample
The founders available to talk are the ones still going. Their approach to risk looks smarter than it was, because the people who made the same bets and lost are not in the room.
Asking for advice instead of history
What should I do gets you generic answers. What did you do at this stage gets you something you can compare against your own situation.
Confusing stage with strategy
Advice from someone running a hundred-person company often describes their current problems, not the ones you have with three people and no revenue. Ask what stage they were at when they learned it.
A workable order for a first conversation
Roughly forty minutes
- 1Open with how they chose the problem and what they left behind, which gets the story out in their own words.
- 2Move to the first ninety days and the first ten customers to force concrete detail.
- 3Then funding, pricing, and the number they watch each morning, once they are talking freely about mechanics.
- 4Close with the near-death moment and what they would change about year one, which is where the honest reflection sits.