How to Money · Friday, October 2, 2026
Matt points out significant drawbacks for self-employed individuals, citing a report that half of them are not contributing to retirement accounts. He also highlights healthcare as a major challenge, noting that individuals must navigate and pay for their own insurance, a stark contrast to employer-sponsored plans.
“Half of folks who are self-employed aren't contributing to a retirement account, which is, oh, my gosh.”
“And obviously, health care is the other massive component. con to working for yourself, right? And that's something that you and I have had to negotiate.”