Office Drama

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.

In this ep, we talk about:
→ how Holly became one of the hottest PMs in tech
→ how she landed PM roles in AI
→ how she became the founding PM of Figma Make just weeks after joining
→ what the OpenAI interview process is actually like
→ what most candidates get wrong in interviews
→ what happened at her live demo during OpenAI Dev Day
→ how to become a better presenter on stage
→ why AI needs more women, creative people, and people with taste
→ what is Dots?
→ how Dots differentiates itself in the current “AI assistant race”

→ Find Holly on LinkedIn:
https://www.linkedin.com/in/hollyli2018

Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions

If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It’s free~

𝙎𝙊𝘾𝙄𝘼𝙇𝙎
🌸 instagram → https://www.instagram.com/chloe.shih
OD instagram → https://www.instagram.com/officedrama.pod
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama

✹ business inquiries: business@colorsofchloe.com

#officedrama #officedramapodcast
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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

Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions
If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~

𝙎𝙊𝘾𝙄𝘼𝙇𝙎
🌸 instagram → https://www.instagram.com/chloe.shih
OD instagram → https://www.instagram.com/officedrama.pod
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama

✹ business inquiries: business@colorsofchloe.com
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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 🥺

➔ Deb's Substack:
https://debliu.substack.com
➔ Deb on LinkedIn:
https://www.linkedin.com/in/deborahliu
➔ Deb on Instagram:
https://www.instagram.com/debliu_

Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions

if you enjoyed this episode please follow, rate 5 stars ⭐️ and drop a comment — it helps more people find the show and means everything to us 🥹

𝙎𝙊𝘾𝙄𝘼𝙇𝙎
🌸 instagram → https://www.instagram.com/chloe.shih
OD instagram → https://www.instagram.com/officedrama.pod
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Thank You to Our Sponsor!
✹ Granola: your AI notepad for meetings → https://granola.ai/officedrama

Ellie Rui got promoted every single year of her career. Six years at Microsoft, from new grad PM to Principal, and now she's a beloved senior PM at Netflix. Her answer for how is simpler than you’d think: hard work doesn't paint the full picture. We get into what actually drives fast career growth, how one great manager changed the trajectory of her entire career, and how the PM landscape is changing faster than ever.

In this ep, we talk about:
→ how she got promoted every single year for six years
→ what a great manager actually does for your career
→ what separates junior, senior, and principal PMs
→ whether AI will actually replace PMs
→ why new grads should pick startups over big tech right now
→ and how to be likeable at work!

→ Find Ellie on LinkedIn: https://www.linkedin.com/in/ellierui/

Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions

If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~

𝙎𝙊𝘾𝙄𝘼𝙇𝙎🌸
instagram → https://www.instagram.com/chloe.shih/
OD instagram → https://www.instagram.com/officedrama.pod/
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama

✹ business inquiries: business@colorsofchloe.com
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Creators got CANCELED for attending an AI brand trip...and we're finally addressing it. 🫣
Today, I have the privilege of hosting Megan Lieu (data science + tech creator) on Office Drama to uncover what really went down on that trip and what it was actually like as a creator "getting canceled".
I've worked professionally in Trust & Safety. I'm passionate about tech ethics, creator industries, and how we all should work together. And I really hope we can actually have constructive conversations on this platform that may push cultural, product, and policy changes for the better.
It's very daunting as a female creator to address a situation like this, so I hope we can show up with empathy, curiosity, and constructive dialogue together. 🫶 Thank you for always making me feel safe to speak up.

In this ep, we talk about:
→ what actually happened on the brand trip
→ the video Megan posted and the moment she realized it was going sideways
→ how the press reaches out when they already know the angle they want
→ why this trip hit a nerve when other AI brand trips didn't
→ why the women creators took the brunt of the backlash
→ how brands and creators should actually give each other feedback
→ where tech creators sit between Silicon Valley's echo chamber and everyone else

→ Find Megan on LinkedIn: https://www.linkedin.com/in/meganlieu

Submit your Coworker Confessions 👇
https://bit.ly/coworker-confessions

If you like what you hear please follow, rate 5 stars on Spotify and Apple Podcasts ⭐️ and leave a comment! 🫶 It's free~
𝙎𝙊𝘾𝙄𝘼𝙇𝙎
🌸 instagram → https://www.instagram.com/chloe.shih
OD instagram → https://www.instagram.com/officedrama.pod
tiktok → https://www.tiktok.com/@chloeshih
threads → https://www.threads.net/@chloe.shih
linkedin → https://www.linkedin.com/in/chloe-shih/
patreon → https://patreon.com/OfficeDrama

✹ business inquiries: business@colorsofchloe.com
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.