Show Notes
today, we unpack the dark side of ambition - what happens when you tie your self-worth to success, why reaching milestones doesn't always bring relief, and our complicated feelings about burnout when we've technically "made it". If you've ever thought "when I get there, I'll finally be happy," this one's for you. this was a moment when I learned about the term "toxic gratitude" where you feel you're not allowed to complain and you should be grateful for the job or position you have. we just quietly suppress our struggles and then we implode by binging manhwa 😳- chlo & eric See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
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How do you go from a self-described “nobody PM” to becoming one of the most talked-about product managers in Silicon Valley? Holly Li’s career is kind of insane. She started at Google, bought a one-way ticket to San Francisco and convinced the team at Adept to create a PM role for her, became the founding PM of Figma Make, and is now building at OpenAI, where she famously launched Dots at OpenAI’s Dev Day.
We’ve spent decades making everything faster, easier, and more convenient, but what if we optimized away some of the things that actually make us human? Srinija Srinivasan is basically a founding mother of the internet. She was employee #5 at Yahoo, spent 15 years there as Editor-in-Chief and VP, helped shape how the early internet was organized, chaired the board of SFJAZZ, served on Stanford’s Board of Trustees, and later co-founded Loove, bringing technology and the arts together. And now, she’s building an entirely new kind of college. In this ep, we talk about: → what it was really like helping build Yahoo! in the early internet → what makes the best business partnerships actually work → why imagination, creativity, and curiosity matter even more in the age of AI → why art is so hard to make money from → the human cost of optimizing everything for efficiency → why convenience might be the wrong North Star for technology → how we can build technology that makes us more human
okay I need you to understand that this episode genuinely changed me 🥹✨ Deb Liu is one of the most decorated women in tech. She spent 12 years at Facebook where she founded Facebook Marketplace, rose to VP, and then became CEO of Ancestry.com. She has 4 million+ views on her Substack, she's a board member of Poshmark and Intuit. She is simply built different! In this episode we get into: → how Facebook Marketplace launched and immediately got a New York Times headline about drugs, guns, and baby hedgehogs 💀 → the invisible rules of power and influence that nobody tells you before you walk into a room → if work feels misaligned you might just need to be repotted 🪴 → how to hold high standards as a leader without traumatizing everyone around you → when to persist, pivot, or quit (and why quitting is actually the first chapter of her new book) → why ambition without joy becomes brittle this is the episode I have been wanting to make since I started Office Drama. Deb is one of those people who has an answer for every question because she has genuinely lived and reflected on such a variety of experiences in her life. This episode is true hopecore and Deb somehow makes you feel like everything is going to be okay 🥺
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