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The question

Can employer penalties replace broad immigration raids?

Target the incentive to hire illegally

Calacanis argues for investigating employers and imposing penalties rather than relying on broad street operations. He returns to that approach in February, describing payroll and tax records as evidence investigators could use to pursue businesses.

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Jason Calacanis · Jan 30, 2026 · 44:09
I've said on this podcast, like many times, but none of you will respond to it, why are they doing this instead of just finding the business owners? Wouldn't that be a better policy? And you're in the White House, you're around these people. Why don't you tell them, why don't we do that? Why don't we just give fines to business owners who hire illegals and stop the incentive to come here?
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Jason Calacanis · Feb 13, 2026 · 59:29
It's super simple. You go to the construction site. Everybody checks in in their morning. They have a truck. This has been done for decades, gentlemen. They take pictures of everybody. Then they go in at the end of the day, after surveilling for weeks, Chamath, and they have done this already. This is all facts. They've had multiple cases where they go to the construction site. They take pictures. They take a video. Then they go to the business owner and say, show us these people's pay stubs. And the business owner goes, I don't have pay stubs for these people. And they say, okay, here's a video of them working for eight hours a day. Where's their pay stub? Show us their taxes. The businesses are paying people off the books. That is tax evasion.
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Separate hiring violations from removing offenders

Sacks accepts that employer penalties may have merit but argues that they are insufficient for people already committing serious crimes. Friedberg also questions how investigators would establish unauthorized hiring. The dispute concerns what the policy can replace, not whether employers should face any accountability.

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David Sacks · Jan 30, 2026 · 45:00
Here's my proposal. Okay, Jay Cal, you may have a point there, Jay Cal. You may have a point, but I'm not sure that it's good enough in the case of an illegal alien who's already been in this country committing crimes. Okay? Yeah, I mean, we all agree on crimes. Hold on, if you have a drunk driver who has killed people through drunk driving and they're captured, I think it should be turned over and deported immediately.
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David Friedberg · Jan 30, 2026 · 44:27
How do you know that they hired illegals? How would you know that? And if you know that, then you know the individuals.
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What would help settle it

Distinguish workplace investigations, employer sanctions and removal of serious offenders. Compare enforcement reach, investigative burden and consequences for people wrongly targeted rather than treating these as one interchangeable policy.