1. How much money did you make last year, and how much did you pay in taxes?

Do you use tax planning strategies to minimize your tax bill each year?

2. Did you inherit any money, and if so, how much?

What did you do with the money? Was there any family conflict or drama that arose over who would get what amount of inheritance money?

3. What was your biggest failure in business?

How have your actions since then been different as a result of that failure?

4. What’s the most in-debt you have ever been?

Was it business or personal debt? How did you get to that point?

5. What is your definition of capitalism, and do you believe it adds value to the world?

Do you think American capitalism needs to be reformed either with regulation or by weakening property rights to move us closer to a socialist system? Or alternatively, does American capitalism maybe need to be reformed by removing regulations and actually strengthening property rights?

6. What do you most want to improve in your decision-making process?

Do you wait too long to make decisions and wish you made them faster with less information? Are you conflict-avoidant and wish you made decisions that were better for the long-term even if that meant initiating more conflict in the short-term?

7. Have you ever lied on your tax return?

These could be business or personal tax returns.

8. Have you ever lied to your spouse about money?

Have you ever lied to your spouse about money? Did you hide a bank account, lie about how much you made, not tell them you spent a lot of money on something you were embarrassed about, etc?

9. What’s something you have done that you aren’t proud of?

This could be either in business or more generally in life.

10. Did you ever steal anything as a kid?

Did anyone ever find out?

11. Do you believe unions are good or bad for the economy?

Do they help workers in the short-term but not in the long-term? Should union-formation laws be reformed? Do unions hold back economic growth in states with strong union laws? What happens to the people who don’t get jobs because unions impose a barrier to competition?

12. Did you sign a prenup before getting married?

If so, how was it structured? Give me concrete details and numbers.

13. Is Bitcoin a pyramid scheme?

Or is fiat currency the pyramid scheme while Bitcoin is the only real money?

14. Do you think [Google/Facebook] should be broken up by anti-trust regulators?

Have big tech companies abused their market power? Should Google be broken up for its competitor-squashing practices? Should Facebook and Instagram be separated even though both face somewhat of an existential threat from TikTok?

15. Do you think Elon Musk is a good business man?

What do you admire about him, and what do you dislike about him?

16. Do you think Donald Trump is a good business man?

Would Donald Trump have been a successful business man without his inheritance?

17. In your opinion, what is Donald Trump’s most impressive business accomplishment?

What is the best thing for a business person to learn from him?

18. What is the probability of the U.S. and China going to war within the next 10 years? The next 50 years?

Are asset management firms foolish for investing in Chinese companies? Will those investments come back to bite them?

19. Do you think ESG initiatives hurt investors?

Will ESG initiatives decrease a company’s stock performance over the long term?

20. Do you think diversity, equity & inclusion initiatives help or hurt investors?

What are your thoughts about DE&I initiatives at companies? Do they decrease shareholder returns over the long term? Are they a cost of doing business to avoid being boycotted or cancelled (i.e. a sort of marketing cost)?

21. Do you think minimum wage laws help or hurt the economy?

If the U.S. had never implemented any minimum wage laws, would last year’s GDP have been higher or lower than it was with those laws?

Would the poverty rate be higher or lower than it was with those laws?

22. Do you think the U.S. will reach a point when debt service payments will exceed tax revenue?

If so, how long do you think it will take us to get there?

If not, do you think we will avoid it by decreasing government spending, increasing taxes, increasing GDP growth, or some combination of those things?

23. Should companies buy carbon credits to be carbon neutral?

Why should investors be okay with their money being spent to buy carbon credits instead of being spent to buy machinery and hire people to grow the business?

24. Do you think taxes should be higher on wealthy individuals?

How wealthy is wealthy? People with $1 billion in annual income? People with $1 billion in net worth? People with $1 million in net worth?

25. Do you think defense contractors are necessary, immoral, or both?

Would you ever start, invest in, or work in a defense contractor company?

26. Do you think companies should have racial diversity hiring quotas?

Or should companies focus on just hiring the most qualified people at a given hiring budget level, regardless of race?

27. What is your immediate emotional reaction to the phrase “living wage”?

Why do you feel that way?

28. Do you think college is worth the money?

Does it depend on the prestige of the college you go to and/or the major you pursue? Do you think everyone should go to college?

29. Do you think college should be free?

If so, how do you think the government should pay for it? And how would you keep college tuition inflation under control?

30. How much of a risk does climate change pose to coastal real estate?

Should investors in south Florida, Louisiana, Texas, New York, and other coastal areas be worried about rising sea levels or increased storm severity due to climate change? Is it worth investing in beach towns at all anymore or is the risk too high?

31. Do you think section 230 should be replaced with different legislation to govern social media censorship?

There is a growing dissatisfaction from both conservatives and progressives with how social media tech companies control online conversations. Conservatives think their voices are being suppressed. Progressives dislike that Elon Musk has control of Twitter and want hate speech to be banned. Do you think section 230 (the law that gives internet companies broad immunity from the content they host) should be repealed, replaced, or modified in some way to better meet the needs of society?

32. Should pension funds be allowed to invest the money of retirees in B corporations?

B corporations are companies that have weaker fiduciary duties than conventional C corporations. Executives of a C corporation are duty-bound to put the interest of their shareholders above all else, while a B corporation’s executives have the ability to spend money in a way that might reduce the company’s stock performance if they think there is some larger public benefit to be had.

Should fully managed pension fund managers be allowed to invest retirees’ money into B corporations?

33. Do you think the U.S. should fund universal healthcare?

Can the U.S. government afford this? Where would the money come from? How would we avoid the quality problems seen in places like the U.K.’s NHS?

34. Do you think the U.S. should fund universal daycare?

Is this more or less of a priority than free college?

35. What jobs are likely to be replaced by robots and/or AI within the next 10 years?

And what jobs are least likely to be replaced?

36. Have you or your business ever been sued?

Tell us the story.