Investor DARES Congressman — Pay 5% First!

Person in business attire offering bundles of US dollar bills
Photo: RomarioIen / Shutterstock

A tech investor publicly dared Congressman Ro Khanna to hand over 5% of his own family fortune before asking billionaires to do the same.

Quick Take

  • Investor David Friedberg challenged Ro Khanna to donate 5% of his family’s $200 million net worth.
  • Khanna and Senator Bernie Sanders introduced the “Make Billionaires Pay Their Fair Share Act,” a 5% annual wealth tax on billionaires.
  • Khanna says the tax could raise $4 trillion over 10 years for childcare, health care, and public college.
  • Entrepreneur Mark Cuban called the plan “insane,” warning it could push founders out of state.
  • The fight touches a bigger question: is taxing extreme wealth fair, or does it cross a legal line?

A Public Dare Over Personal Wealth

David Friedberg, a tech investor and podcast host, challenged Representative Ro Khanna directly on social media. He wrote that he wanted to see Khanna “make a voluntary contribution of 5% of your family’s $200M net worth to the government for important healthcare, childcare, and jobs”. The comment turned a policy debate into a personal test of consistency.

Friedberg had first mocked the plan on social media, writing “why stop at 5%?! keep going, Ro, keep going!!” before shifting to a sharper accusation. He argued Khanna was pushing a policy that amounted to government seizure of private property rather than a normal tax. The exchange quickly spread across tech and political circles online.

The Case Khanna Makes For Taxing Billionaires

Khanna, a California Democrat, has defended the tax for months. He says about 900 billionaires hold 22% of the country’s economic output, and taxing that wealth could raise $4 trillion over a decade. He calls the country’s wealth gap a “second Gilded Age” and says the money would fund childcare, public college, trade schools, and expanded Medicare.

Khanna teamed up with Senator Bernie Sanders to introduce the “Make Billionaires Pay Their Fair Share Act” in March. The bill would place a 5% annual tax on the roughly 938 billionaires in America. Khanna argues billionaire wealth sits untaxed for years because it comes from stock and property gains rather than regular income, unlike wages most workers pay tax on immediately.

Pushback From Fellow Entrepreneurs

Not everyone in the business world agrees with Khanna’s framing. Billionaire investor Mark Cuban called a related California wealth tax plan “insane” during a public back-and-forth on social media. Cuban argued the state would effectively loan money to founders who would immediately hand it back as tax payments, calling the structure confusing and self-defeating for the people it targets.

Friedberg has said he does not fully disagree with Khanna on the broader problem. He has argued that tax policy in America is flawed and that capital gains on borrowed wealth should be taxed at a higher rate than they are now. His disagreement centers less on whether billionaires should pay more and more on whether Khanna should lead by personal example first.

A Deeper Legal and Political Fight

Khanna has pushed back on accusations of hypocrisy before. He has noted he won his primary election by a wide margin after publicly backing the 5% billionaire tax, arguing voters support the idea even in a district full of tech wealth. He also says a one-time version of the tax could offset health coverage losses tied to Medicaid cuts, citing conversations with economists who called the approach reasonable.

Beyond the personal dispute, legal scholars remain split on whether a federal wealth tax could survive a Supreme Court challenge under the Constitution’s rules on direct taxes. That unresolved question means the Friedberg-Khanna clash is really a preview of a much larger fight. Both sides agree the tax system needs fixing, they simply disagree on who should be forced to fix it first, and how.

Sources:

yahoo.com, aol.com, youtube.com, hotair.com, sanders.senate.gov