This Week On Bullish: When To W2 That 1099

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Hello friends, and welcome back to another episode of Bullish, TechCrunch’s first talk show. This week we taped at Disrupt SF, so our setup looks slightly different than usual. It was also warm. We blame the sun.

Joining us this time around is Senator Mark Warner, a former venture capitalist and current member of our national Congress. The Senator and I chewed over an important question: When does a contractor become an employee? Given Sen. Warner’s experience in the technology fields, he knows a thing or two about hiring.

Do we need a third category between an employee and a contractor? It’s a line of questioning that has dozens of your favorite startups sweating.

Many young companies today employ contract laborers, lowering their labor costs. However, some argue that the system — often called the ‘gig economy’ — passes expenses unfairly to workers who, if they were full employees, would be able to keep more of their income. Uber is a classic example of the situation. Courts are on the case, as you might imagine.

We also took a moment to discuss the divide between Silicon Valley and the Capitol. Politics is increasingly dependent on technology at the precise moment that technology is more and more active in the political arena. Despite those colliding trends, there remains a lack of understanding between the differing camps.

The results of that coolness can be embarrassing.

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Join 10k+ tech and VC leaders for growth and connections at Disrupt 2025

Netflix, Box, a16z, ElevenLabs, Wayve, Hugging Face, Elad Gil, Vinod Khosla — just some of the 250+ heavy hitters leading 200+ sessions designed to deliver the insights that fuel startup growth and sharpen your edge. Don’t miss a chance to learn from the top voices in tech. Grab your ticket before doors open to save up to $444.

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Oh, and the senator declined to advocate for the entry of vice president Joe Biden into the presidential race. We’ll have to wait and see what happens there. Hit play and we will see you all next week back in our usual digs.

Bullish airs every Wednesday morning at 7 am Pacific, and 10 am Eastern. 

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