You would lose that bet. 12 million Americans filed a Schedule D with $5k+ in capital gains in the last year the IRS has stats on. (That's 1 out of every 8 re

You would lose that bet. 12 million Americans filed a Schedule D with $5k+ in capital gains in the last year the IRS has stats on. (That's 1 out of every 8 returns.) https://www.irs.gov/uac/soi-tax-stats-individual-income-tax-returns-publication-1304-complete-report#_pt1 https://www.irs.gov/uac/soi-tax-stats-individual-income-tax-... There are numerous other ways to have income outside of formal employment in the US. The most salient one for tax purposes is self-employment.