Tiger Sisters

Thank you SoFi for sponsoring this video. Sign up here: https://www.sofi.com/Tiger

Most people rush into a new year with new "goals" without ever questioning the systems running their lives. 

In this Tiger Sisters episode, Jean and Cherie sit down for an honest conversation about the rules they’re actually living by in 2026: the mental models, boundaries, and decision frameworks that reshaped their careers, relationships, energy, and sense of self over the past year.

This isn’t a goal-setting episode. It’s a conversation about how you DESIGN A LIFE you love.  Drawing from their experiences across Harvard, Stanford, Wall Street, Silicon Valley, and building Tiger Sisters, Jean and Cherie unpack what they’re keeping, what they’re letting go of, and what they’re refusing to negotiate going forward.

We break down:
✅ Why goals failed them — and what replaced them
✅ The personal rules that protect energy, focus, and relationships
✅ How to design a life around seasons instead of pressure

This episode is for anyone who feels successful on paper, but knows something NEEDS to change before the next chapter.

🐯👯‍♀️ We’re the Tiger Sisters — your Wall Street & Silicon Valley big sisters
Decoding Money • Power • Love
✨ New episodes every Monday | Shorts all week ✨

💌 Want to partner with us?
Sponsorships: [email protected]

⏰ Timestamps
00:00 Why this isn’t a goal-setting episode
02:15 What we stopped optimizing for in 2025
05:10 The difference between pressure and clarity
08:40 The rules we no longer negotiate
12:30 Designing life around seasons, not grind
16:05 Why curation is our new superpower
19:40 The decisions that quietly changed everything
23:15 Letting go of performative ambition
26:20 What we’re protecting in 2026
29:45 The question we’re using before every big decision
33:10 How we’re defining success differently now
36:40 The cost of staying in old systems
40:05 What this next chapter actually requires
43:30 Final reflections going into 2026

Why trust us?
▫️ Cherie Brooke Luo — 100M+ views demystifying tech, finance & MBAs
▫️ Jean Luo — ex-Goldman Sachs, ex-Snapchat exec, 50+ AI patents, startup investor
▫️ Together: 4 Ivy League degrees • built billion-dollar products • two startups — decoded for you

What you’ll get (and keep):
▫️ 🚀 Ivy League cheat sheets — no $250K tuition
▫️ Personal finance playbooks (salary, investing, negotiation)
▫️ Networking scripts behind $100M+ deals & job offers
▫️ Real conversations with CEOs, operators & investors
▫️ Mindset resets — clarity without the pricey coach
▫️ Systems for career, money, and long-term growth

💛 LET’S CONNECT

~ CHERIE ~
Instagram — /cherie.brooke
TikTok — /cherie.brooke
Substack — cherieluo.substack.com
LinkedIn — /cherie-luo

~ JEAN ~
Instagram — /jeanluo_
LinkedIn — /jeanluo

👉 Hit Subscribe & tap the 🔔, then leave a ⭐️⭐️⭐️⭐️⭐️ review on Spotify & Apple Podcasts.
It takes 10 seconds and makes a massive difference in helping new people discover Tiger Sisters.

🛍️ Items:
🍵 Sisters Matcha — www.sistersmatcha.com
🌀 Everything else — https://amzn.to/3z0dx5b

Thank you SoFi for sponsoring this video. Sign up here: https://www.sofi.com/TigerSisters

We’re bringing this conversation to you because most people never get a window into how leaders like this actually think, especially high-powered women who’ve built iconic careers in finance. In this Tiger Sisters episode, Jean and Cherie sit down with Holly MacDonald, CEO of Bessemer Trust – $298B in AUS (assets under supervision).

This is a rare conversation about leadership at the highest levels of finance, wealth management, family offices, what it actually takes to earn trust over decades, and how women navigate authority and credibility in rooms where decisions move billions.

Holly shares the lessons she’s learned rising to the top of one of the most respected firms in finance, from managing long-term client relationships to leading with clarity in moments of uncertainty.

We break down:
✅ What it really means to manage wealth across generations
✅ How trust is built (and lost) in high-stakes environments
✅ How women earn authority without performing or posturing
✅ The long-term thinking required to lead through volatility
✅ Why judgment, not charisma, is the most underrated leadership skill

🐯👯‍♀️ We’re the Tiger Sisters: Your Wall Street & Silicon Valley big sisters
Decoding Money • Power • Love
✨ New episodes every Monday | Shorts all week ✨
💌 Want to partner with us? Sponsorships: [email protected]

⏰ Timestamps
01:27 - What Is a Family Office?
03:00 - Running a $298BN Firm
05:21 - The Secret to Moving from COO to CEO in Finance
06:15 - Her Advice: Don't Do Everything
07:39 - You Can Have It All (At Different Times)
09:36 - Don't Step Out of the Race (DON'T LEAVE YOUR CAREER)
15:20 - How Do Family Offices Work? And What Can We Apply?
16:18 - What Is the Purpose of Your Wealth?
18:12 - What Is the Common Goal For Wealth?
22:30 - How Can We Translate Billionaire-Thinking?
26:30 - What IS YOUR MONEY FOR?
28:30 - What is Holly's Personal Financial Goal?
33:10 - How Holly Navigates Male Dominated Spaces (Finance)
36:00 - Accumulate Information & Know WHEN To Use It
38:57 - Career Starters, Give Your Input To Senior VPs!
40:52 - Fortune Questions Ice Breaker
43:28 - The Most Outrageous Thing You've Done For Love

Why trust us?
▫️ Cherie Brooke Luo — 100M+ views demystifying tech, finance & MBAs
▫️ Jean Luo — ex-Goldman Sachs, ex-Snapchat exec, 50+ AI patents, startup investor
▫️ Together: 4 Ivy League degrees • built billion-dollar products • two startups — decoded for you

What you’ll get (and keep):
▫️ 🚀 Ivy League cheat sheets — no $250K tuition
▫️ Personal finance playbooks (salary, investing, negotiation)
▫️ Networking scripts behind $100M+ deals & job offers
▫️ Real conversations with CEOs, operators & investors
▫️ Mindset resets — clarity without the pricey coach
▫️ Systems for career, money, and long-term growth

💛 LET’S CONNECT
~ CHERIE ~
Instagram — /cherie.brooke
TikTok — /cherie.brooke
Substack — cherieluo.substack.com
LinkedIn — /cherie-luo

~ JEAN ~
Instagram — /jeanluo_
LinkedIn — /jeanluo

👉 Hit Subscribe & tap the 🔔, then leave a ⭐️⭐️⭐️⭐️⭐️ review on Spotify & Apple Podcasts. It takes 10 seconds and makes a massive difference in helping new people discover Tiger Sisters.

🛍️ Items:
🍵 Sisters Matcha — www.sistersmatcha.com
🌀 Everything else — https://amzn.to/3z0dx5b

In this episode, we sit down with Admiral Mike Rogers, former Director of the National Security Agency (NSA) and Commander of U.S. Cyber Command, for a rare, wide-ranging conversation on how the world is changing, and what actually matters now.

Mike shares what he learned from nearly four decades at the highest levels of military, intelligence, and government leadership, including working under both President Obama and President Trump. But this isn’t just a conversation about power or national security. We also talk about love, relationships, and the personal tradeoffs that come with ambition: why success without meaning is empty, how leaders should think about partnership and family, and what really lasts when titles, money, and influence fade.

This episode is about leadership in every sense of the word: 
- What leadership looks like when the stakes are highest
- How global cyber risk and AI affect everyday people
- Why integrity is the non-negotiable trait of great leaders
- How to communicate effectively with radically different decision-makers
- National security vs. privacy — why it’s not a binary choice
- What the private sector and government misunderstand about each other
- Why love, not power or money, is the ultimate long-term investment

🐯👯‍♀️ We’re the Tiger Sisters — Your Wall Street & Silicon Valley big sisters
Decoding Money • Power • Love
✨ New episodes every Monday | Shorts all week ✨

💌 Want to partner with us?
Sponsorships: ⁠[email protected]⁠

Timestamps:
1:16 Is the NSA listening to our conversation?
1:38 You need integrity as the foundation
3:38 He became a 4-star military admiral 
6:18 How to make decisions when there's no "right" answer?
7:25 Differences in working with President Obama vs. Trump
14:09 Are politics & business just pre-orchestrated?
17:58 Which is more important? National security or privacy?
20:51 Cybersecurity in the US government
29:58 Admiral Mike talks about love
36:56 Wrap up with Mike Rogers

▫️ Cherie Brooke Luo — 100M+ views demystifying tech, finance & MBAs
▫️ Jean Luo — ex-Goldman Sachs, ex-Snapchat exec, 50+ AI patents, startup investor
▫️ Together: 4 Ivy League degrees • built billion-dollar products • two startups — decoded for you
▫️ 🚀 Ivy League cheat sheets — no $250K tuition
▫️ Personal finance playbooks (salary, investing, negotiation)
▫️ Networking scripts behind $100M+ deals & job offers
▫️ Real talk with CEOs, operators & founders
▫️ Mindset resets — clarity without the pricey coach
▫️ Lifestyle, wellness & productivity systems that actually work

💛 LET’S CONNECT
~ CHERIE ~
Instagram: /cherie.brooke
TikTok: /cherie.brooke
Substack: cherieluo.substack.com
LinkedIn: /cherie-luo
~ JEAN ~
Instagram: /jeanluo_
LinkedIn: /jeanluo

👉 Hit Subscribe & tap the 🔔, then leave a ⭐️⭐️⭐️⭐️⭐️ review on Spotify & Apple Podcasts. It takes 10 seconds and makes a massive difference in helping new people discover Tiger Sisters.

🛍️ Items:
🍵 Sisters Matcha — ⁠www.sistersmatcha.com⁠
🌀 Everything else — ⁠https://amzn.to/3z0dx5b

In this Tiger Sisters episode, Jean and Cherie revisit one of the most shared conversations in our community: how to stop settling without blowing up your entire life. This episode is both a mirror and a roadmap — designed to help you get honest with yourself, listen to your body, and make intentional decisions about the year ahead.
We’re bringing this episode back because this is the exact moment people quietly lock in another year of a life that feels… fine. And you deserve more than fine.
We share:
✅ The simple question that reveals whether you’re settling
✅ Why your body knows the answer before your brain does
✅ How to get honest with yourself without burning everything down
✅ Why “stop settling” applies to careers, relationships, and identity
✅ How small decisions today quietly shape your next year
✅ Why this episode resonated so deeply with our audience
🐯👯‍♀️ We’re the Tiger Sisters — Your Wall Street & Silicon Valley big sisters
Decoding Money • Power • Love
✨ New episodes every Monday | Shorts all week ✨
💌 Want to partner with us?
Sponsorships: [email protected]
Timestamps:
2:10 Same job, same relationship patterns, same life
4:05 Why most people avoid answering this honestly
6:30 Don’t answer with logic — notice your body’s response
9:15 This episode is a mirror, not a judgment
11:40 Why “stop settling” doesn’t mean blowing up your life
14:20 The quiet decisions that lock in another year
17:05 Why this conversation resonated so deeply
19:45 How to create change without chaos
22:10 This applies to career, love, and identity
24:50 The cost of staying comfortable
27:10 What to do if you’re scared but know it’s time
29:10 Final reflection: choosing yourself

https://cherieluo.substack.com/
▫️ Cherie Brooke Luo — 100M+ views demystifying tech, finance & MBAs
▫️ Jean Luo — ex-Goldman Sachs, ex-Snapchat exec, 50+ AI patents, startup investor
▫️ Together: 4 Ivy League degrees • built billion-dollar products • two startups — decoded for you
▫️ 🚀 Ivy League cheat sheets — no $250K tuition
▫️ Personal finance playbooks (salary, investing, negotiation)
▫️ Networking scripts behind $100M+ deals & job offers
▫️ Real talk with CEOs, operators & founders
▫️ Mindset resets — clarity without the pricey coach
▫️ Lifestyle, wellness & productivity systems that actually work
💛 LET’S CONNECT
~ CHERIE ~
Instagram: /cherie.brooke
TikTok: /cherie.brooke
Substack: cherieluo.substack.com
LinkedIn: /cherie-luo
~ JEAN ~
Instagram: /jeanluo_
LinkedIn: /jeanluo
👉 Hit Subscribe & tap the 🔔, then leave a ⭐️⭐️⭐️⭐️⭐️ review on Spotify & Apple Podcasts. It takes 10 seconds and makes a massive difference in helping new people discover Tiger Sisters.
🎵 Music: Sammy Signal
🛍️ Items:
🍵 Sisters Matcha — www.sistersmatcha.com
🌀 Everything else — https://amzn.to/3z0dx5b

Most people think career success is ALL about working harder. It’s not. It’s also about how you’re perceived, how you communicate, and whether the right people see your value. And no one is taught these rules.
In this remix episode of Tiger Sisters with Lorraine K. Lee and Leah Wyar, we bring together two of our most impactful conversations to break down the invisible dynamics that determine who gets promoted, trusted, and listened to at work.
Executive presence expert Lorraine K. Lee explains how body language, communication, and visibility quietly shape credibility. Media and Entertainment Leader Leah pulls back the curtain on what actually happens inside organizations — the politics, the pressure of climbing, and the emotional labor no one prepares you for. This episode is for anyone who’s doing great work but feels overlooked, underestimated, or stuck.

We share:
✅ Why hard work alone doesn’t lead to promotion
✅ How perception quietly determines influence and opportunity
✅ The body language and communication habits that signal leadership
✅ Why visibility compounds — and how to build it intentionally
✅ How to navigate loyalty, boundaries, and self-advocacy without burning bridges
✅ What executive presence really means in real life and on Zoom

This isn’t about becoming louder or more aggressive. It’s about learning the unspoken rules so you can move with clarity and confidence — on your own terms.

🐯👯‍♀️ We’re the Tiger Sisters — your Wall Street & Silicon Valley big sisters.Decoding Money • Power • Love
✨ New episodes every Monday | Shorts all week ✨

💌 Want to partner with us?
Sponsorships: [email protected]
👀 Newsletterhttps://cherieluo.substack.com/
Timestamps:
0:58 - End of Year Remix: Lorraine & Leah Interviews
02:15 - Perception + Influence = Power
02:35 - Welcome Lorraine K. Lee
05:52 - First Impressions (Fix Your Face)
15:20 - Create Your Personal Brand (In-Person & On LinkedIn)
18:00 - This ONE Word Makes You Sound More Persuasive
34:16 - The Conversations To Get Promoted At Work
39:15 - Lorraine Recap And Bridge To Episode 2
40:15 - Welcome Leah Wyar
55:54 - Say Yes In Life and In Romance!!
1:06:57 - Navigating Workplace Politics
01:22:35 - How High Powered Women Think About Love
01:32:23 - Closing Thoughts From Cherie & Jean

Why trust us?
▫️ Cherie Brooke Luo — 100M+ views demystifying tech, finance & MBAs
▫️ Jean Luo — ex-Goldman Sachs, ex-Snapchat exec, 50+ AI patents, startup investor
▫️ Together: 4 Ivy League degrees • built billion-dollar products • two startups — decoded for you
What you’ll get (and keep):
▫️ 🚀 Ivy League cheat sheets — no $250K tuition required
▫️ Personal finance playbooks — salary, investing, negotiation
▫️ Networking scripts behind $100M+ deals & job offers
▫️ Real talk with CEOs, operators, and builders
▫️ Mindset resets — clarity without the pricey coach
▫️ Career systems that actually work

💛 LET’S CONNECT
~ CHERIE ~Instagram — /cherie.brookeTikTok — /cherie.brookeSubstack — cherieluo.substack.comLinkedIn — /cherie-luo
~ JEAN ~Instagram — /jeanluo_LinkedIn — /jeanluo👉 Subscribe, tap the 🔔, and leave a ⭐️⭐️⭐️⭐️⭐️ review on Spotify & Apple Podcasts. It takes seconds and helps more people find Tiger Sisters.

🎵 Music: Sammy Signal
🛍️ Sisters Matcha — www.sistersmatcha.com
🌀 Everything else — https://amzn.to/3z0dx5b