Questions to Ask a Millionaire
Questions for a conversation with someone who has built substantial wealth: how the money was actually made, what it cost, how they invest now, and what changed once they no longer had to work. Written for interviewers, students of business, and anyone who gets one hour with a person worth asking.
The questions
Open any question for the note
How did you actually make your money?
Why ask it
Left open on purpose. People who built something tell it as a story with dates and setbacks, while people who inherited, married into it, or got lucky on a single asset answer in one sentence and change the subject.
What was the first year you earned more than you needed?
Why ask it
Pins down the year saving became possible at all. It is usually much later than people assume, and hearing the actual age deflates the idea that wealth either starts early or never.
What did you do with the surplus once there was one?
Why ask it
The gap between earning well and keeping any of it is where most high earners stall. Listen for whether money moved into assets automatically or only when they remembered.
What was the single decision that made the biggest difference?
Why ask it
Forces one answer instead of a list of ten. It is often something unglamorous, like refusing to move to a bigger house, rather than the deal they are known for.
What is the most money you have lost on one thing?
Why ask it
You want a number and a date. Anyone who says they have never lost money is either new to investing or editing the account for you.
How do you decide whether to put money into something?
Why ask it
Ask for the actual filter: position size, time horizon, and what would make them sell. Answers about backing good people usually mean there is no filter.
What share of your net worth is in the thing you know best?
Why ask it
Concentration is how most fortunes are made and how a good number are lost. The percentage tells you whether they are still betting or now protecting.
What do you pay other people to handle, and what do you still do yourself?
Why ask it
The list of things they refuse to delegate is usually the list of things they genuinely understand. Everything else has been outsourced to someone with a fee.
What did you cut back on, and for how long?
Why ask it
Turns abstract frugality into specifics: the car they kept, the holidays they skipped, the years it lasted. Months and a decade are very different answers.
What advantages did you start with that are easy to miss?
Why ask it
A fair-minded answer names family support, timing, a cheap city, or a degree somebody else paid for. A flat denial that there were any is also useful information.
Who told you no early on, and were they right?
Why ask it
Gets past the highlight reel. Some of those rejections were correct, and hearing one admitted is a sign you are getting the real version rather than the after-dinner one.
How did you handle the first year the numbers went the wrong way?
Why ask it
Recovery behavior matters more than upside. Ask what they sold, what they stopped paying for, and who they told, in that order.
What does your money let you say no to?
Why ask it
Concrete where a question about what wealth means invites a speech. Answers tend to be bad clients, a commute, a difficult relative, or a boss.
What do you spend on now that would have shocked you twenty years ago?
Why ask it
Lifestyle drift is far easier to admit through this door than through a question about spending discipline.
Has money changed which friendships lasted?
Why ask it
Almost everyone with money has a story here and few have been asked for it. Expect a pause before the answer, and let the pause run.
What have you told your children about the money?
Why ask it
Forces a stated position on inheritance, disclosure, and expectation. Most people have thought about this far more than they have said out loud.
What are you still worried about financially?
Why ask it
Worry rarely scales down with net worth. Health costs, a business that could turn, a dependent relative: the answer shows where they feel exposed.
How much of this could you repeat if you started again now?
Why ask it
Separates a repeatable skill from a set of conditions that happened once. Honest answers usually concede that a large share was the era they started in.
What do people ask you for that you have learned to refuse?
Why ask it
Money attracts requests. What they decline, and how they explain declining it, shows how they think about obligation to other people.
What should someone on an ordinary salary take from your story, and what should they ignore?
Why ask it
The second half is the point. It asks them to mark the parts of their own advice that do not generalize, which few people volunteer unprompted.
Getting a real answer
Practical guidance for the conversation itself
Before the conversation
Decide whether you want method or story
Method means numbers, filters, and time horizons. Story means decisions and the years around them. Both are worth having, but they need different questions, and alternating at random tends to produce neither.
Read what is already public
If they run a company, a fund, or a foundation, the basics are on record. Asking what you could have found in five minutes spends the goodwill you will need later, when you ask about losses.
Settle what is off limits first
Net worth, current holdings, and family are the three areas people most often decline. Agreeing that up front is better than watching an answer close halfway through a sentence.
Reading the answers
- A precise figure and a date for a loss is a good sign. Round numbers with no timeline usually mean the story has been retold more often than it has been examined.
- Watch the pronouns. Many people switch to we at the difficult parts and back to I at the successes.
- If every answer arrives with a lesson attached, you are hearing a keynote. Ask what the week was actually like instead.
- Note whether they mention timing at all. People who never bring up the decade they started in are usually selling something.
Common pitfalls
Asking for a tip
It ends the interesting part of the conversation and gets you the answer they give everyone at parties. Ask how they decide rather than what they currently hold.
Treating one outcome as evidence
You are talking to a survivor. The people who took the same risks and lost are not in the room and never will be, so the failure rate is invisible from where you are sitting.
Copying the move and skipping the conditions
Cheap property, low rates, an industry with no competition yet: most specific moves depended on conditions that have gone. Ask what would have to be true for it to work now.