“Oh, earth, you're too wonderful for anybody to realize you. Do any human beings ever realize life while they live it—every, every minute?”
- Emily Webb from Thornton Wilder’s Our Town
Welcome to the first official rebranded Tiger Sisters Newsletter. We are so excited to kick off this companion newsletter: think of this as the conversation that happens after the podcast ends. Each week, we’re sharing the behind-the-scenes stories, frameworks, recommendations, life updates, and advice we’re still thinking about long after we stop recording.
It’s a catch-up with your Wall Street and Silicon Valley big sisters. Grab your matcha or beverage of choice and let’s get into it ☕️
This week’s Tiger Sisters episode features a conversation we recorded live from Cannes Lions (in France!!) with Reddit COO Jen Wong.
In the episode, we discuss:
How Jen helped scale Reddit into a public company, leading its IPO
Why career reinvention is NEVER a linear path (even though it might look that way on LinkedIn)
How one of the greatest accelerators of success is to surround yourself with people who see your potential before you see it yourself
Also, can we talk about the fact that we recorded this episode in a literal fishbowl?! 🐠 The Reddit Deli activation at Cannes Lions was designed as a giant glass storefront, so we spent the entire interview with hundreds of conference-goers walking by, stopping to watch, and peering in like we were exhibits at an aquarium. A true Tiger Sisters first.
📚 What We’re Reading This Summer
Jean:
Title: These Walls: The Battle for Rikers Island and the Future of America’s Jails by Eva Fedderly
Description: A powerful inside look at the failures of Rikers Island and what its planned closure reveals about the future of America’s criminal justice system.
Jean’s take: I literally read this book cover to cover in less than a day. It’s a thoughtful, deeply researched read that explores how architecture and the design of our prison system can either reinforce injustice or become a tool for reform. Backed by compelling research and eye-opening statistics, the book makes a powerful case that mass incarceration remains a modern, state-sanctioned extension of America’s long history of systemic racism.
Cherie:
Title: Yesteryear by Caro Claire Burke
Description: A sharp and dark satire about a glam tradwife influencer who travels to 1855 and is forced to confront the reality behind the lifestyle she’s built her brand around.
Cherie’s take: Everyone seems to be reading Yesteryear, so I thought it was time to see what all the hype was about. I’m listening to the audiobook and I’m more than halfway through, and the protagonist drives me nuts. She’s a deeply unlikeable and unreliable narrator. Last year I read Yellowface by R.F. Kuang, and Yesteryear’s has a similar tone and voice – the way it weaves in the impact of social media on burnout and mental health (think doomscrolling through angry tweets written about you). I’d love to hear your take if you’ve read it, or whether it’s on your reading list.
Red Carpet Behind the Scenes: The Art of the Interview
Last month, we flew to Cannes Lions to interview some of the biggest names in media and tech. We were the Red Carpet Correspondents for People Inc.’s Sunset Villa Party. It got us thinking…We want to share more about the art of the interview. It’s an interviewer’s job to ask the good questions and to get a level deeper. Here are our top tips on how to show up.
Ask the follow-up questions. The first answer is polished, but the second response goes into the details. I get so annoyed when podcast hosts or interviewers can’t bring the conversation one level deeper. Ask a follow up.
Do your research. Then be okay to ditch the script so the conversation flows more naturally. When you’ve done your homework and are actually prepared, you’re more confident and can be more engaged with the guest in the moment.
The best interviewers are great listeners. If you are busy thinking about your next question, or what you’ll say next, you are probably missing an opportunity to connect.
Kill your imposter syndrome (because it’s not about you). You don’t need to prove you are smart. Or that you belong. It’s your job to make the other person feel understood.
Follow your genuine curiosity. People can tell when you’re asking a question because you have to versus because you genuinely want to know.
You can find the rest of our tips in our Tiger Sisters IG carousel here
⭐️ Highlight of the Week: What We’ve Watched
We are HUGE theater, film, and culture nerds and we’ve had the absolute pleasure of experiencing 3 incredible works of art over the last few weeks:
Alicia Key’s musical, Hell’s Kitchen
Christopher Nolan’s The Odyssey
Phantom of the Opera on Broadway
Our favorite was Phantom of the Opera, which is performing across the country as the cast makes its nationwide tour. I can see why this show ran on Broadway for 35 years. Please go see it if you have a chance!
⚡ Rapid Fire with Jen Wong, COO of Reddit
Each week on the podcast, we ask our guests a few questions to get to know the human behind the résumé. Here’s what Jen Wong had to say:
📺 What are you currently watching?
Theodore Roosevelt, a documentary about Teddy Roosevelt on Netflix.
✈️ A destination you’d recommend:
Tokyo 🇯🇵
🧩 Your guilty pleasure?
Word puzzles and mobile games.
💭 A piece of advice you come back to again and again?
“You can say most things on your mind and there will be fewer consequences than you think there would be.”
🧠 Tiger Sisters Frameworks of the Week
The Dinner Party Test
One of the biggest takeaways from our conversation with Jen Wong is the “dinner party test”.
Whether you’re building a business, growing a personal brand, or creating content, the first thing you should ask yourself before posting is: “Would I say this if I were at a dinner party with people I didn’t know?”
If the answer is... “I’m just here to promote myself or sell my business”... then don’t post it. If the answer is “I’m here to contribute something thoughtful and interesting,” you’re on the right track.
Here are 3 key takeaways you can put into practice immediately:
Lead with value, not promotion. Share a lesson, observation, story, or resource that people would genuinely find useful – something that’s really shifted your thinking.
Write the way you’d naturally speak to someone across the dinner table. If it feels overly polished, corporate, or sales-y, people will tune out.
Build trust before you ask for attention. The more often you help or inform people, the more receptive they’ll be when you eventually promote something.
What do you think about the Dinner Party Test? You can find the full conversation with Jen Wong below.
How Can You Make Faster & Better Decisions?
When faced with a decision, put it through this lens: is it irreversible, or reversible? Determining this will help you save a lot of time, effort, and probably money.
In our recent episode, Everything I Learned at Stanford Business School in 90 Minutes, we discussed one of our favorite mental models from Jeff Bezos. It divides decisions into two types:
🔒 Type 1: One-way doors. These are difficult-to-reverse decisions (think: choosing a co-founder, quitting your job, or selling your company). Make sure to really slow down and think these through, carefully weighing the pros and cons.
🚪 Type 2: Two-way doors. These are reversible decisions and include things like: testing a new website feature, launching a content series, or trying a different marketing strategy. The key here is to move quickly, experiment, and learn.
🎧 Coming soon on Tiger Sisters…
These are some episodes we’re launching soon– stay tuned!
Engineering a Remarkable Life: What if you approached your life with the same intentionality you’d use to build a successful company? In this two-part Masterclass, Cherie distills one of the most legendary (and hardest-to-get-into) classes at Stanford Business School, taught by the late, great Joel Peterson. Through frameworks, mental models, and interactive exercises, you’ll learn how to engineer your life across three pillars:
A Person to Be: How to build a strong foundation by identifying your values, examining your personal history, and auditing your strengths and blind spots.
Someone to Love: Learn why your closest relationships shape every aspect of your life, and how to approach love, friendship, and family with intention.
The Work to Do: Discover how to build meaningful work, prioritize what truly matters, navigate adversity, and create a life of purpose that outlasts your career.
Revamping Your LinkedIn: LinkedIn can be cringe, but it’s also one of the highest-leverage career tools on the internet. Cherie spent years at LinkedIn and is a LinkedIn Top Voice with 35,000+ followers. In this upcoming two-part masterclass, Cherie teaches Jean (and all of us) how to build a profile that opens doors, focusing on the below areas for beginning, intermediate, and advanced profiles:
The About Me: How to tell your story, position yourself, and stand out.
Personal branding: Banners, proof points, hobbies, calls to action
Searchability: SEO, keywords, and how to use AI to improve your profile, without sounding like AI.
Glenn Kramon’s ‘Winning Writing’: Everyone has an email they’re terrified to send. Maybe it’s to a dream employer, an investor, a potential mentor, or someone who’s already ignored your first two follow-ups. In this exclusive interview, we sit down with legendary New York Times editor and Stanford professor, Glenn Kramon, to unpack the lessons from Winning Writing, one of Stanford Business School’s most beloved (and hardest-to-get-into) classes.
This is a communication masterclass from a legendary editor whose reporters have won 10 Pulitzer Prizes (and have been named Pulitzer finalists 25 times!)
Until next week...
Thanks for spending part of your Monday with us. Share this newsletter to someone who would learn something new from the Tiger Sisters! Reply to this email and tell us: What’s one topic you want us to cover next? We’re in the test-and-learn phase and would love to hear from you.
See you soon, Tiger Fam,
Cherie & Jean