Thank You to Our Sponsors!

✹ Storyblocks: unlimited stock footage, music, and SFX for creators → https://storyblocks.com/officedrama

✹ Granola: your AI notepad for meetings → https://granola.ai/officedrama

✹ Hostinger: build your website with AI and get 10% off with code OFFICEDRAMA → https://hostinger.com/OFFICEDRAMA

What does it actually look like to build wealth as a woman in 2026 ~ when you have a corporate career, a creator business, and more ways to make money than ever before?

Jenny didn’t leave corporate to become a creator... she built both at the same time, made six figures from content, and still genuinely loves having a job 😭 which makes her perspective on money, ambition, and the creator economy so interesting.

In this ep, we talk about:

→ why Jenny became a creator

→ why she still refuses to quit her corporate job

→ how she made $100K as a creator with only 60K followers

→ what actually makes brands want to work with you

→ why women feel guilty for wanting more money

→ how creators are making millions from online courses

→ whether selling a course is actually a “grift”

→ why white women tend to do well as influencers

→ how women are making crazy money in 2026

→ scarcity, competition, and representation in the Asian creator community

→ why women should feel empowered to build wealth

→ Find Jenny on Instagram: https://www.instagram.com/mohae.jennypark/

→ Find Jenny on TikTok: https://www.tiktok.com/@mohaewithjennypark

→ Find Jenny on LinkedIn: https://www.linkedin.com/in/jenniferkimpark/

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: [email protected]

#officedrama #officedramapodcast

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

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: [email protected]

#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: [email protected]

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: [email protected]

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: [email protected]

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 Sponsors!

✹ Storyblocks: unlimited stock footage, music, and SFX for creators → https://storyblocks.com/officedrama

✹ Quince: high quality essentials, radically low prices → https://quince.com/officedrama

✹ Granola: your AI notepad for meetings → https://granola.ai/officedrama

Duolingo has become one of the most recognizable brands on the internet, but what does it *actually* take for a language-learning app to become a cultural phenomenon?

Katherine “Kat” Chan, Sr. Director of Marketing at Duolingo, has spent her career at the intersection of tech, culture, and creativity. Before helping turn Duo into the internet’s favorite unhinged owl, she worked at Red Bull, Tesla and Facebook, alongside some of the biggest names in tech like Elon Musk and Mark Zuckerberg.

And despite all of that, Kat has almost no digital footprint. She rarely does interviews, which made this a very rare chance to unpack how she actually thinks about creativity, taste, ambition, and building brands people genuinely care about.

In this ep, we talk about:

→ how Duolingo built a brand that moves at internet speed

→ why most companies can’t simply copy the Duolingo playbook

→ what “good taste” actually means and whether you can learn it

→ how Kat hires and identifies exceptional creative talent

→ where AI can make creatives better... and where it makes us dangerously average

→ what working at Tesla and Facebook taught her about prestige, burnout, and choosing the right environment

→ and the question I can’t stop thinking about before becoming a mom: can you actually have it all?

This episode is a masterclass in taste, creative leadership, internet culture, and building an ambitious career without letting ambition consume you.

→ Find Kat on Linkedin:

https://www.linkedin.com/in/yotsechan/

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~

Apple Podcasts: https://podcasts.apple.com/us/podcast/the-art-of-being-tastefully-unhinged-sr-director/id1752596006?i=1000785565362

Spotify: https://open.spotify.com/episode/05BVa2zx0dWMAWCgFTtHwl?si=5LL91A13T262DbQW6zPsAg

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:

[email protected]

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

Half of 2026 is officially over... and I've never felt this behind in my career. 😅

In today's episode of Office Drama, I'm doing my mid-year review out loud: what went wrong, what I'm scared of, and the 6 commitments I'm making so December-me doesn't have to go through the same existential disappointment.

Today, we talk about:

→ Why I felt so behind at the half-year mark of 2026

→ The motherhood penalty: how does it impact your career? 👀

→ A mutual creator who lost 10,000 followers overnight after announcing her pregnancy

→ "Would you rather be pregnant or successful?" and why I don't want to choose!

→ My 6 commitments I want us to try for the rest of 2026

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!

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:

[email protected]

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 Sponsors!

✹ Storyblocks: unlimited stock footage, music, and SFX for creators → https://storyblocks.com/officedrama

We've heard time and time again about the burnt out tech employee who quits a stable job to chase the dream. This time we're exploring the reverse!

Daniel "Tafo" Lee has lived more careers than I can count on two hands. JPL engineer, coach to Melee god Mang0, Yahoo Esports show host, CLG General Manager, the internet's Tetris teacher, Web3 economist, Andreessen Horowitz, and now, at 37, starting over in big tech. He's no stranger to the creator economy and his honest take on who should actually pursue it might save you five years of your life.

In this ep, we talk about:

→ how he coached a Melee god while working full time at NASA JPL

→ the ultimatum from his wife that finally made him quit and move to Esports

→ why 90% of streamers won't make it, and why minimum wage might be the better option

→ betting on yourself at 37: relearning how to code from scratch in the AI era

→ and how becoming a dad made him reevaluate the value of his time

This episode is for anyone who's ever been told to follow their passion and quietly wondered if that advice is a trap. Tafo is proof that the real flex isn't dying on one hill but maybe knowing when to walk away towards the next one.

→ Find Tafo:

https://www.instagram.com/tafokints

https://www.linkedin.com/in/daniellee912

https://x.com/tafokints

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:

[email protected]

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

Nobody tells you that when you get cast on MasterChef, you get to choose three people to fly out as your friends and family. Jaime (  @igumdrop  ) chose Aria (  @AriaSaki  ) , Kimi (  @AngelsKimi  ) and I, and we spent a week on set with NO phones, 7AM call times, and a front-row seat to watching her cook on the biggest stage of her life.

In this ep, we talk about:

→ why Jaime almost went alone

→ the mandolin accident that didn't make it to air

→ what Gordon Ramsay is ACTUALLY like

→ the moment Aria destroyed a MasterChef contestant

→ what traditional TV gets right that creators don't

→ why chasing perfection as a creator isn't sustainable

→ the narratives that get rewritten about women in gaming and streaming

→ Find Jaime:

https://www.youtube.com/@igumdrop

https://www.twitch.tv/igumdrop

https://www.instagram.com/igumdrop/

https://www.tiktok.com/@igumdrop

→ Find Aria:

https://www.youtube.com/@AriaSaki

https://www.twitch.tv/ariasaki

https://www.instagram.com/ariasaki/

https://www.tiktok.com/@ariasaki

→ Find Kimi:

https://www.youtube.com/@AngelsASMR

https://www.youtube.com/@AngelsKimi

https://www.twitch.tv/angelskimi/

https://www.instagram.com/angelskimi/

https://www.instagram.com/gentleflamestudio/

https://www.tiktok.com/@angelskimii

A huge thank you to the MasterChef production team for letting us share these stories!

#MasterChef #MasterChefGlobalGauntlet @MasterChefonFOX @FOXTV @FoodClubFOX

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: [email protected]

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

Over the past decade, Jaime (@iGumdrop) has built a 2M+ following, founded her own successful clothing brand, dropped out of college to pursue streaming, and now she's on the cast of Season 16 of MasterChef!

In this week's episode of Office Drama, we get into the version of the story you don't see on TV.

In this ep, we talk about:

→ why she almost said no to MasterChef

→ what it's like to be on the cast of MasterChef

→ the insane reality TV background check nobody warns you about

→ what Gordon Ramsay is ACTUALLY like in person

→ the roti canai controversy

→ the truth about agents, managers, and the people you work with as a creator

→ why "the interview never matters" and what she actually hires on

→ how she skipped the 5-year plan and went straight to a deathbed plan

This episode is for anyone who's ever been underestimated, boxed into one version of themselves, or scared to take the leap because they might look like a fool. Jaime is one of the most earnest, chaotic, hilarious people I know, and watching her bet on herself, publicly, after ten years of quietly putting in the work is exactly the kind of story I started this show to tell.

→ Find Jaime:

https://www.youtube.com/@igumdrop

https://www.twitch.tv/igumdrop

https://www.instagram.com/igumdrop/

https://www.tiktok.com/@igumdrop

A huge thank you to the MasterChef production team for letting us share these stories!

#MasterChef #MasterChefGlobalGauntlet

@MasterChefonFOX @FOXTV @FoodClubFOX

Submit your Coworker Confessions 👇

https://bit.ly/coworker-confessions

Thank You to Our Sponsors!

✹ Storyblocks: unlimited stock footage, music, and SFX for creators → storyblocks.com/officedrama

✹ Quince: luxury-quality essentials without the markup → quince.com/officedrama

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:

[email protected]

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