The 3 rules Chelsea Handler thinks you should break to make millions

What do you do when the world tells you to tone it down? If you’re Chelsea Handler, you turn up the volume—on confidence, career, and comedy. In this unapologetic and hilarious episode of The Burnouts, Phoebe Gates and Sophia Kianni sit down with the legendary comedian and bestselling author who’s built an empire on not giving a f***. They talk through confidence myths, investor pitch chaos, stand-up breakthroughs, and why Chelsea bought her ex 35 trees. Also: why burnout might actually be your breakthrough.

 

Chapters

1:22 – were you always this confident?

6:14 – how to say no (and mean it)

11:02 – kids, career, and confidence clashes

15:00 – real estate, financial freedom & female power

21:06 – mushrooms with your landscaper & other business lessons

25:45 – dating while dominating

30:12 – women, work, and not shrinking yourself

 

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About the Burnouts

As former Stanford roommates and now business partners, Phoebe Gates and Sophia Kianni share their experience as startup founders and the chaos of building something new—covering everything from pitching VCs to maintaining friendships, decoding financial literacy, and finding power in female-driven storytelling. With candid conversations and top guests (like Kris Jenners and Sara Blakely), The Burnouts is your go-to for smart, hilarious, and sometimes chaotic advice on how to build your career on your own terms.