Questions to Ask an Entrepreneur About Starting a Business
For someone thinking about starting something and getting time with a founder who already has: twenty questions about the first version, the first ten customers, what the early money looked like, and the month they nearly stopped.
The questions
Open any question for the note
What did the first version of this look like, and what did it cost to make?
Why ask it
Founders remember the first version fondly and describe it accurately, and it is almost always cruder than outsiders assume. The cost figure resets your sense of what you need before you start.
How did you get your first ten paying customers, one by one?
Why ask it
One by one is the important part, because it forces specifics rather than a channel strategy that only existed later. Most honest answers involve people they already knew, which is worth knowing before you budget for advertising.
What were you living on in the first year?
Why ask it
Savings, a partner's salary, contract work, staying at a parent's house: the answer explains how they survived the period with no revenue. It also tells you what runway you would need to copy their approach.
When did you leave your job, and what was the trigger?
Why ask it
The threshold people actually use, a signed contract, a set number of months of expenses saved, a manager who forced the choice, is more useful than advice about following your gut. Ask whether they would use the same threshold again.
How much money went in at the start, and where did it come from?
Why ask it
Savings, a credit card, family, a small loan, a grant, an investor: each carries different pressure, and the source shapes every decision that follows. A founder who started with a family loan and one who took a bank loan will give you different advice for the same reason.
What did you spend money on early that you would not spend again?
Why ask it
The list is usually short and specific: an office, a logo, a custom-built system, a trade show, legal work done too early. This is the cheapest lesson available in the whole conversation.
Which month were you closest to stopping?
Why ask it
Asking for a month rather than a feeling gets you a real story instead of a resilience speech. What they did that month, borrowed, cut, sold something, asked for help, is the practical part.
How long was it before the business paid you a wage you could live on?
Why ask it
This number is often years rather than months, and it is the one most likely to be softened in public accounts. It sets your expectations better than any revenue figure.
What did you get wrong about who your customer was?
Why ask it
Nearly everyone aims at the wrong buyer first, and the correction usually came from a sale they did not expect. Ask how they found out, because that method is something you can repeat.
How did you set your first price, and what happened when you raised it?
Why ask it
First prices are usually guesses copied from a competitor, and the story of the first increase tells you how much room was there. Watch for how many customers actually left, which is nearly always fewer than they feared.
What did you keep doing yourself for too long?
Why ask it
Bookkeeping, support, deliveries, the website. The answer marks where their attention was trapped and often where growth stalled for a year.
What legal or tax setup do you wish you had sorted out on day one?
Why ask it
Common answers are a separate bank account from the start, registering the right entity, written agreements with a co-founder, and getting a bookkeeper before the first tax deadline. Cheap at the beginning and expensive to unpick later.
Who was your first hire, and would you hire that role first again?
Why ask it
Many founders hire someone like themselves and later wish they had hired the opposite. The answer tells you what work they had misjudged as easy.
What did you promise a customer early on that nearly broke you?
Why ask it
Everyone overcommits when they need the sale, and the story usually involves a deadline, a custom feature or a price. Ask what they say now when the same request comes in.
What number were you watching to know it was working?
Why ask it
Repeat orders, weekly bookings, referrals, a shortening sales cycle. If they were watching nothing, ask what they wish they had counted, because that answer is just as useful.
What did it cost you outside of money?
Why ask it
Time with children, a relationship, sleep, health, friendships that went quiet. Founders rarely volunteer this and often answer it seriously when asked directly.
Who did you have to ask for help, and how did you ask?
Why ask it
The wording of a request for a loan, an introduction or a favour is a skill, and most people who built something have got good at it. Ask what they said, not just who they asked.
What advice did you take that turned out to be wrong for your situation?
Why ask it
It is the most useful question you can ask a mentor, because it teaches you to filter rather than obey, including filtering what they are telling you. Raise capital early, hire fast and niche down all show up here.
If you started again with a fraction of what you had, what would you do in the first ninety days?
Why ask it
The constraint is what makes this worth asking, and it strips away the advantages they may not realise they had. Listen for whether the answer starts with selling something or with building something.
What should I stop romanticising about the early days?
Why ask it
A closing question that invites them to puncture the version of the story they usually tell. The answers tend to be about admin, loneliness and the sheer number of small decisions.
Getting Real Answers From a Founder
Practical guidance for the conversation itself
Ask about their business, not business in general
Anchor every question to a transaction
How do you find customers produces a lecture. Tell me about the third sale you ever made produces a story with a name, a price and a reason. Keep pulling the conversation back to single events.
Ask for numbers with a range attached
People who will not name their revenue will happily tell you how many months it took to break even, roughly what they started with, or what a typical order is worth. Ranges are enough to plan against.
Follow up with what happened next
Most first answers stop at the decision. The consequence, whether the customer stayed, whether the hire worked out, is where the lesson actually is.
Ask what they would need to be true to give the opposite advice
It is a gentle way to test whether a strong opinion is a rule or a preference, and it usually gets them to name the conditions their advice depends on.
Correct for the fact that they made it
- Ask what they had that you might not: a spouse's income, an existing client list, industry contacts, a technical skill, a period of cheap rent, timing.
- Ask about the competitor who did roughly the same thing and did not survive. It is the fastest way past the story that success was inevitable.
- Take patterns from several founders rather than a plan from one. A single account is a case study, not evidence.
- Remember that they are describing a market that existed when they started. Ask what has changed since about customers, costs and competition.
- Notice how much of their explanation is luck being retold as strategy. Most people do this without meaning to.
Respecting the meeting you asked for
- Ask for a specific slot, thirty minutes, and end at thirty minutes even if they are enjoying it. That is what gets you a second conversation.
- Send one short paragraph in advance saying where you are and the two things you most want to ask. It saves ten minutes of context and gets better answers.
- Do not bring a pitch or ask them to sign a confidentiality agreement. You came for their experience, not to sell them anything.
- Do not ask them to tell you whether your idea is good. Ask what they would test first if it were theirs.
- Take notes by hand, and write down their exact words rather than your interpretation.
- Follow up within a month saying what you actually did with the advice. It is rare, it is remembered, and it is the whole basis of asking again.
What to do with the answers
- Turn the advice into one testable next step this week: ten conversations with buyers, one paid pilot, a price on the table.
- Write down which of their claims you can check, then check them: what things cost, what a licence requires, how long an approval takes.
- Verify anything legal, tax or regulatory with someone qualified in your own jurisdiction. Founders are describing what happened to them, not what applies to you.
- Keep a note of the advice you decided not to take, with the reason. It is worth rereading in a year.