Questions to Ask Entrepreneur
For the person considering doing this themselves rather than reporting on it. These questions are aimed at what you would need to survive the first two years: how the bills got paid, what took longer than expected, which standard advice turned out to be wrong, and which parts of their path you should not copy. If you are interviewing a founder for an article or a class, the standard questions to ask an entrepreneur set is the better shape.
The questions
Open any question for the note
What were you doing right before you started, and what made you finally leave?
Why ask it
The trigger is usually more specific than a passion for building things: a redundancy, a visa, a client who offered to pay, a manager they could not work for another year. That detail is the useful part, and it rarely appears in the public version of the story.
What did you have in place before you started that you would tell me to have too?
Why ask it
Savings, a first client, a working notice period, a partner's income. This turns their situation into a checklist you can hold against your own.
Who was your first paying customer, and how did you find them?
Why ask it
The answer is almost never a marketing channel; it is a person they knew or someone they contacted directly. Ask what they said in that first approach, since it is the closest thing to a repeatable lesson in the whole conversation.
How long did it take to earn what you were earning before, and did you expect that?
Why ask it
The honest answer is usually years rather than months. It is the single most useful number for anyone deciding whether to leave a salary.
How did you pay your rent in the first year?
Why ask it
Savings, a partner's salary, consulting on the side, family money, a loan. Whichever it was determines how much risk they could take, and it is the piece most often left out when their path is presented as replicable.
What did you believe about your market that turned out to be wrong?
Why ask it
Look for a specific correction: the buyer was a different person than expected, the pricing was too low to support a sales call, the problem was real but not urgent. Founders who cannot name one have usually not looked closely.
What did you spend money on at the start that you would tell me to skip?
Why ask it
Branding, offices, software, incorporation help: most founders can name at least one. It is cheap advice for you and easy for them to give.
Which piece of standard startup advice turned out to be wrong for you?
Why ask it
Gets you past the received wisdom that gets repeated on every podcast. Their disagreement is usually rooted in something concrete about their market, so ask why it did not apply rather than accepting the headline.
How did you split equity, and would you do it the same way again?
Why ask it
Equity splits and the absence of vesting are behind a large share of founder disputes. Most people who have been through one will speak plainly about it, and their regret is more instructive than any template.
What is the hardest conversation you have had to have?
Why ask it
Firing a friend, telling staff about a missed payroll, ending a cofounder relationship. This question moves the conversation from strategy to the part of the job that people are least prepared for and find hardest to delegate.
What broke first when the business grew?
Why ask it
Something always does: support volume, cash flow timing, a process that only worked because one person remembered everything. Ask when they noticed and what the warning sign was, since that is the part you could recognise early yourself.
What was your first hire, and what did you get wrong about hiring?
Why ask it
Early hires are frequently made for the wrong reason, availability, friendship, a skill the founder disliked using. Ask what they would hire for first if they started again, and whether the answer is the same role.
If you were starting again with no savings, what would you do in the first month?
Why ask it
This forces the answer into a shape that fits someone with fewer resources than they had. It is more transferable than the story of what they actually did.
How much of your time goes on things you never expected: contracts, payroll, support, tax?
Why ask it
The unglamorous overhead is what surprises people who imagine running a business as building a product. A rough percentage is a useful reality check if you are thinking about starting something yourself.
What is the closest you came to running out of money, and what did you do?
Why ask it
Nearly every business has this month, and the specifics, delaying salaries, a loan from a customer, a discount for prepayment, are the part nobody writes about. It also shows how they behave under real pressure.
If you raised money, what changed the week after?
Why ask it
Ask about the reporting, the board dynamics and the expectations, not the valuation. Founders often describe a shift in who they answer to that they had not fully anticipated when they signed.
What does your business look like from the outside that is not true?
Why ask it
Almost every founder has a version of this: the headcount looks larger, the revenue looks steadier, the growth looks smoother. Asking directly gives them permission to correct the picture, and most take it.
What should I test before I give up any income?
Why ask it
Founders are usually direct about this because they wish someone had told them. Expect a specific test rather than general encouragement.
What has this cost you personally?
Why ask it
Handled respectfully, this is the question founders remember being asked. Answers tend to be specific: a relationship, a decade of savings, health, friendships that quietly lapsed while they were busy.
Knowing what I have told you about my situation, what would worry you most?
Why ask it
Turning the conversation onto your own plan gets you a critique you cannot easily get elsewhere. Ask it near the end, once they know enough to answer.
What part of your path should I not copy?
Why ask it
Invites them to separate what worked from what merely happened to work out, including luck, timing and a market that has since closed. It is also a graceful way to end, and the answer is usually the most honest thing they say.
Making the conversation worth their time
Practical guidance for the conversation itself
Before you meet
- Read what they have already said publicly and skip those questions. Founders answer the same three questions constantly, and skipping them is the clearest signal that you prepared.
- Decide what you actually want from the conversation: a decision you are stuck on, a market you are researching, an introduction. Vague admiration produces vague answers.
- Ask for a specific, short slot rather than open-ended time. Twenty focused minutes is easier to grant than a coffee with no end.
During the conversation
- Ask about one instance rather than the general approach. What did you do in March when the contract fell through gets a story; what is your approach to resilience gets a platitude.
- Follow the numbers. When they mention a figure, ask what it was a year earlier. The trajectory is where the real content is.
- Let silences sit. The second half of an answer, after the pause, is usually the part that was not rehearsed.
- Do not pitch your own idea unless invited. If they ask, keep it to two sentences and one specific question.
What not to ask
- How do I get funding. It is too broad to answer, and it signals that you want a shortcut rather than a conversation.
- Anything you could have found on their website or in a recent interview. It spends the goodwill you came in with.
- Requests for a large favour in the first meeting. Ask for one small, concrete thing at the end, or nothing at all.
Afterwards
- Send a short note with the one thing you are going to do differently. It is specific, it takes them ten seconds to read, and it makes a second conversation likely.
- Report back when you have done it. Founders keep talking to people who close the loop, and almost nobody does.
- Offer something in return, however small: a customer introduction, a bug you noticed, a candidate. The exchange is what turns a single meeting into a relationship.