What Questions to Ask an Entrepreneur
A narrower set than the general list, for when the part you want to understand is the money. It covers pricing and what a sale actually leaves, how long the business could run without new sales, how it was funded and on what terms, when the founder started paying themselves, and which numbers they check each week. For the wider story of how the business began, the standard questions to ask an entrepreneur set covers that.
The questions
Open any question for the note
How did you set your first price, and what has changed it since?
Why ask it
First prices are guesses and the revisions are where the learning is. Ask what evidence made them move the number.
What does a sale leave you once delivery, fees and support are counted?
Why ask it
This separates revenue from what the business actually keeps. Founders who can answer immediately usually run tighter operations.
How did you get your first ten customers?
Why ask it
This is the question founders answer most concretely, because early customers are remembered by name. Expect unglamorous answers involving personal networks and cold outreach, and be skeptical of anyone who credits a marketing channel at that stage.
When did you start paying yourself, and how did you arrive at the figure?
Why ask it
The date sets how long the founder subsidised the business. The method behind the figure shows whether pay is planned or whatever is left.
How many months could you run with no new sales?
Why ask it
Cash cover decides how a business behaves under pressure, more than turnover does. It also explains hiring and pricing choices.
What was the closest you came to shutting it down?
Why ask it
Nearly every business has a month it should not have survived, and the details of that month are worth more than any account of the good years. Watch whether the rescue was a decision they made or something that happened to them.
What is the hardest decision you have had to make about a person?
Why ask it
Firing a friend, buying out a co-founder, or keeping someone too long are the answers that come up, and they get at judgment rather than strategy. Founders who claim no difficult personnel decisions have either been lucky or have avoided the decisions.
Where does the money actually go each month?
Why ask it
The cost breakdown is rarely what an outsider guesses, especially the share taken by payments, software and insurance. Ask which line surprised them.
Which piece of standard advice turned out to be wrong for you?
Why ask it
This invites disagreement with received wisdom, which is where the useful specificity lives. It also tests whether they think from their own experience or repeat the conference consensus back to you.
How do you decide what not to do?
Why ask it
Most opportunities that kill small companies looked like growth at the time. Founders with a working answer can name a live opportunity they turned down and why, rather than talking about focus in the abstract.
What does it cost you to win one customer, and how did you work that out?
Why ask it
Many small businesses have never calculated this. Either answer is informative: the number, or how they operate without it.
How did you fund it, and what would you do differently?
Why ask it
Bootstrapping, debt, and outside investment each buy a different set of problems. The regret half of the question is where you learn what the money cost them in control, dilution, or the pace they were then forced to keep.
What did you learn about pricing the hard way?
Why ask it
Underpricing, discounting to close and free work for exposure are the usual candidates. The story tends to be specific and easy to learn from.
Who did you hire too late, and who too early?
Why ask it
Both errors are common and they teach different lessons about sequencing. The specific role named, whether it was a salesperson, a bookkeeper, or a second engineer, is more useful than any general theory of team building.
How do you handle customers who pay late?
Why ask it
Late payment is the quiet cash problem in most small businesses. The answer covers terms, chasing and when they stop working for someone.
What part of the work do you still do yourself, and why?
Why ask it
The answer distinguishes between the tasks they genuinely should own and the ones they cannot let go of. Many founders will admit, if asked plainly, that some of what they keep is habit rather than judgment.
What has this cost you outside of work?
Why ask it
Health, a relationship, years of weekends: the honest answers are specific and rarely offered unprompted. Ask it late, ask it once, and accept a short answer, since it is the question most likely to be genuinely private.
What would you change about how you funded it?
Why ask it
Loans, savings, investors and revenue each leave a different kind of regret. Ask what they would keep as well.
Starting again tomorrow with what you know now, what would you skip entirely?
Why ask it
Framed this way you get the negative list, which is more actionable than the positive one and rarely appears in interviews. Common answers include an office, a rebrand, a hire, and a year spent building before selling anything.
What should I be asking you that I have not?
Why ask it
Founders spend their days on problems nobody outside the company asks about, and this hands them the floor. It works best at the end, once they can see you have been listening rather than collecting quotes.
Getting a useful hour from a founder
Practical guidance for the conversation itself
Before the conversation
Do the twenty minutes of homework
Read what they have already said publicly and look at what the company actually sells. Asking what the business does wastes the part of the meeting where attention is highest.
Have one thing you want to leave with
A single decision you are trying to make gives the conversation a spine, and it lets a busy person be genuinely useful rather than generally encouraging.
Ask for a specific, short slot
Twenty-five minutes with a stated purpose gets accepted far more often than an open invitation to pick their brain, and it usually runs long anyway if the conversation is good.
During it
- Ask about their decisions, not about your plan. Founders are experts on what they did and merely opinionated about what you should do.
- Push once for specifics when an answer is abstract. Naming a number, a month, or a customer usually turns a platitude into something you can use.
- Do not pitch. If they want to invest or help, they will ask, and a conversation that turns into a request is rarely repeated.
- Take notes by hand or ask before recording. Founders speak more freely when they can see nothing is being captured verbatim.
- Watch the clock yourself and offer to stop at the time you asked for. This is the single behavior that earns a second meeting.
What not to do
- Asking for the secret of their success, which invites the rehearsed answer and closes off everything interesting.
- Asking for confidential numbers early. Wait until the relationship justifies it, or ask about ratios and directions instead of figures.
- Treating survivor stories as method. One person's route through a specific market at a specific time is evidence, not instruction.
- Asking a question you could have answered by searching for ninety seconds.
- Following up with a long document. A three-sentence thank-you naming what you are going to do is remembered; an attachment is not.
Afterwards
Write up the notes the same day
You will remember the story and forget the two sentences that mattered. Fifteen minutes while it is fresh is what turns a pleasant meeting into something you actually act on.
Report back once you have done something
A short update a month later, showing you acted on one piece of what they said, is the most effective way to keep the door open. Most people never send it.
Compare across people rather than deferring to one
Ask four founders the same question and you will get four incompatible answers. The overlap is the part worth trusting.