If you had an opportunity to interview a self-made millionaire, what would you ask?
June 29, 2012 2:21 PM   Subscribe

If you had an opportunity to interview a self-made millionaire, what would you ask?

I'm working on a new podcast about startups and I'm looking for ideas from the general public about what they would like to know from successful entrepreneurs.
posted by joshuamcginnis to Work & Money (30 answers total) 6 users marked this as a favorite
"Is a million bucks as rich as you thought it would be?"

Because it probably isn't. Sad, but true.
posted by DarlingBri at 2:33 PM on June 29, 2012 [2 favorites]

What is your favorite thing about planet earth?
posted by Golden Eternity at 2:33 PM on June 29, 2012

What would make you lose all your money?

When did you first realize you were rich? What did you do?
posted by parmanparman at 2:39 PM on June 29, 2012 [2 favorites]

Since you've become a millionaire, have your political views changed?
posted by box at 2:41 PM on June 29, 2012 [9 favorites]

When you were 8, what did you want to be when you grew up?
posted by headnsouth at 2:49 PM on June 29, 2012

How did you decide who to partner with and when?
posted by Heart_on_Sleeve at 2:57 PM on June 29, 2012 [1 favorite]

What, outside of your business, are you passionate about? If you wanted to become an expert at something unrelated to your business, what would it be?
posted by tully_monster at 3:12 PM on June 29, 2012

Mod note: The question doesn't suggest that joke answers are what the OP is looking for, so please refrain, folks.
posted by restless_nomad (staff) at 3:13 PM on June 29, 2012

Why did you tell people you're rich?
posted by a robot made out of meat at 3:13 PM on June 29, 2012

And how do people treat you differently now?
posted by a robot made out of meat at 3:18 PM on June 29, 2012

Were you no longer wealthy, do you think you could (or would know how to) earn it all again from scratch? Do you think that some of your success is from luck or a one-time opportunity rather than sheer skill?
posted by Jehan at 3:19 PM on June 29, 2012

One point: "If you had an opportunity to interview a self-made millionaire, what would you ask?" is different than "If you had an opportunity to interview a very successful entrepreneur, what would you ask?"

I say it because I think it's relevant to your podcast. If I download a podcast about entrepreneurs, I'm going to have different expectations than I would for a podcast that just interviews millionaires. You can mix in different kinds of questions, but be sure to keep your eye on the ball: entrepreneurship.

My suggestions:
– What mistakes did you make related to your business? (Bad marketing campaigns, confusing website layout, hiring the wrong person, etc.)
– What do you know about your industry now that you didn't before you became successful?
– Was there a "turning point" for your business? (Endorsement from a celebrity, commercial going viral, angel investor, etc.)
– Are there any other industries you have thought about branching out into after the success of your current one?
– Did you run into any tricky legal problems that you wish you had anticipated before?
– What background do you have (professional, educational, or otherwise) that helped to make your business a success?
posted by hypotheticole at 3:22 PM on June 29, 2012 [5 favorites]

What % of how you got there was hard work and what was luck (being somewhere at exactly the right time, meeting a random person who really helped etc)?

Did you use a detailed business plan?

What advice do you have for people just starting out?
posted by meepmeow at 3:37 PM on June 29, 2012

Pretty much anything not related to money or business. They are probably sick of it, and the information is boring.

- Whats your favorite low key restaurant in town?
- Favorite brand of socks?
- Whats better, star wars or star trek, and why?
- Whats the most embarrassing thing you have done in the last month or so?
- Have you ever farted at a meeting? if so, did anyone catch on that it was you?
posted by couchdive at 3:40 PM on June 29, 2012

I would outline the very basic points found in The Millionaire Next Door and then ask if these points are true for them. If yes, how much has this mindset contributed to their current financial situation and what advice do they have for others ("if you could advise people to make only one change, what would it be"). If no, what do they think about the people reflected in the statistics found in that book/study, and how much do they think it reflects society today (15 years later).
posted by Houstonian at 3:45 PM on June 29, 2012 [1 favorite]

Do you really think you are a "self-made" millionaire?
posted by LeanGreen at 3:58 PM on June 29, 2012 [8 favorites]

Actually, I've interviewed many, but about specific business issues, rather than their success in life.
posted by LonnieK at 4:04 PM on June 29, 2012

How have your buying habits changed--or not--since you became a millionaire?
posted by MonkeyToes at 4:10 PM on June 29, 2012

I wouldn't ask them anything about being a millionaire at all. Surely that's the most boring thing to ask someone with the potential for awkwardness as well.

Ask unique things - what insights do they have about the business landscape? What are their predictions for the industry they're in? What kind of thinkers in their business do they champion? Which ones do they deride? Is there a counter-intuitive hobby or source that they feel as taught them a lot about their business etc. Have they worked in other start-ups? How was theirs different from the one's that failed? Why are they interested in start-ups as opposed to your regular multinational?

Really a millionaire is neither here nor there; it's just a number and has no more meaning than 900k or 1.1m. Further, and I hate to sound like a bourgeois prat here, but it's not that much - unless they own it outright. Selling your business for 1m does not equal 1m; nor if you have a 900k mortgage.
posted by smoke at 4:28 PM on June 29, 2012

What was your most spectacular failure?
posted by lulu68 at 4:46 PM on June 29, 2012 [1 favorite]

I have heard that in Japan there is a saying to the effect that "luck is a skill". What skill or skills do you have that you think helped you "get lucky" or helped you be in the right place at the right time which might be non-obvious to other people?
posted by Michele in California at 4:50 PM on June 29, 2012 [3 favorites]

Is "millionaire" being used here as a shorthand for "really rich person"? Because, in the US, being a millionaire isn't that extraordinary (people who have fairly mundane occupations but have saved and invested assiduously for twenty or thirty years are often millionaires). So, to treat them as extraordinary simply because they have a $million+ net worth seems to be fairly naive.
posted by allnamesaretaken at 5:31 PM on June 29, 2012

Self made millionaire is not a narrow distinction. A sizeable fraction of the members of metafilter have probably got a million dollars worth of liquid assets. It is a lot more common than it was in the days when "millionaire" was more meaningful as a term of distinction. Look at the ask metafilter thread for "how much money do you consider to be 'fuck you' money.

Here is my current formula. Calculate your yearly burn rate. Take your net liquid assets and divide by your yearly burn rate. This is how many years you can not work and stay solvent. Look at the Social Security Administration life expectancy tables. If your years of expenses stashed is ten times your years expected to live, that is my formula for calculating 'fuck you' money.


30 000 / yr. burn rate. 1 000 000 dollars stashed. -> 33 years expenses stashed.

Remaining life expectancy: 30 years. YOU AREN'T EVEN CLOSE KEEP TOILING!

(What would most interest me in talking to a substantially wealthier person is how they would construct such a formula.)
posted by bukvich at 7:04 PM on June 29, 2012

@bukvich: OK, I'll bite.
When you say 'you aren't even close,' do you mean because:
a. Your life expectancy might beat the actuarials
b. Your 1mm stash could be wiped out in a crash
c. Something else
d. A combo of these
posted by LonnieK at 8:39 PM on June 29, 2012

Mostly economic crisis; my biggest fear in cutting it closer is the idea of thirty dollars for a loaf of bread. (Although I prefer to outlive the actuarials if I could do so healthfully.)
posted by bukvich at 8:46 PM on June 29, 2012

Over the years, I've had the opportunity to have conversations with some incredibly wealthy people - billionaires - and a few who I think are among the wealthiest on earth. I've learned more interesting things by listening rather than questioning. I think this is true of most situations though... a simple open-ended question or two is going to produce more substantive dialog than something that could lead to a simple yes/no.
posted by blaneyphoto at 9:37 PM on June 29, 2012

"How much tax do you pay?"
posted by Perodicticus potto at 12:33 AM on June 30, 2012

What were you taught about money growing up, and has 'making it' changed your attitude?
posted by EatMyHat at 5:50 AM on June 30, 2012

If you could go back and do you life over, would you strive for material success the next time through?
posted by hworth at 6:51 AM on June 30, 2012

Do you know how much a pint of milk costs?
posted by mippy at 4:12 AM on July 2, 2012 [1 favorite]

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