Tiger Sisters

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

Most people spend more time with their boss than with their family. So if that relationship is toxic, it doesn’t just make work harder… it can actually impact your career trajectory, mental health, reputation, and financial future. 

In this episode, we break down how to identify a truly toxic boss (not just a demanding one), strategic moves if you realize you’re in a bad situation, and what to do if *you’re* actually the toxic boss. We also share YOUR anonymous workplace horror stories and discuss what we can learn from them.

Tune in for specific lessons on:

 ✅ The 5 biggest red flags of a truly toxic boss

 ✅ How toxic managers damage careers, teams, and mental health

 ✅ What to do before escalating to HR (and why HR isn’t always your savior)

 ✅ Strategic ways to protect your reputation and plan your exit

 ✅ How to evaluate whether a future boss is actually a great leader

 ✅ A self-check exercise: what if you’re accidentally becoming the toxic boss?

If you’ve ever wondered if your boss is toxic or if you’re overreacting, or why your job may feel so psychologically draining, then this episode is for you. Because at the end of the day: your boss can accelerate your career… or quietly destroy it. 

📝Resources mentioned in the episode: 

HBR’s 5 Red Flags of a Toxic Boss:

https://hbr.org/tip/2025/03/5-red-flags-of-a-truly-toxic-boss?utm_source=chatgpt.com  

HBR’s 10 Signs of a Toxic Boss:

https://hbr.org/2025/02/10-signs-of-a-toxic-boss-and-how-to-protect-yourself 

Laszlo Block’s Work Rules: Insights from Google That Will Transform How You Live and Lead:

https://www.amazon.com/Work-Rules-Insights-Inside-Transform/dp/1455554790 

Simon Sinek’s Leaders Eat Last: 

https://tinyurl.com/576s5dxt 

00:37: Episode goals

01:28: The universal experience of a toxic boss

02:40: Definition of a ‘toxic’ boss 

03:42: Jean’s anecdote of a toxic boss

05:42: 5 Red Flags of a truly toxic boss 

12:20: How toxic bosses create a culture of fear 

14:20: Reading your toxic boss horror stories 

18:15: Male vs. female toxic bosses 

21:40: Methods to navigate a toxic boss 

23:45: HR is not your friend 

25:08: What to do if you’re in a toxic work culture 

25:50: Laszlo Block on what to look for in a job

27:47: Simon Sinek on “leaders eat last”

30:00: Cherie’s positive boss experience

32:54: How to tell if *you’re* the toxic boss 

36:33: Action plan if you do realize you’re toxic 

37:00: Lasting thoughts and field research 

🐯👯‍♀️ 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]

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

Learn more about your ad choices. Visit podcastchoices.com/adchoices

Thank you SoFi for sponsoring this video. Sign up here:

https://www.sofi.com/TigerPlus

Most people still underestimate what the biggest creator-led businesses have quietly become. In this Tiger Sisters episode, Jean and Cherie sit down with Andrew Yaffe, CEO of Dude Perfect, the team behind one of the most iconic YouTube brands in the world, with 60+ million subscribers and $100M raised from Wall Street.

This is a rare, behind-the-scenes conversation about how a YouTube channel actually turns into a real, institutional-grade business spanning media, IP, merchandise, live experiences, and private equity investment. Andrew breaks down what it takes to scale a YouTube brand without losing its soul, why Dude Perfect waited YEARS before taking outside capital, and how they built a company that could outlast algorithms, trends, and platforms.

Tune in for lessons on: 

✅ How Dude Perfect scaled from viral videos into a diversified media empire

✅ Why Wall Street backed a YouTube brand with $100M in private equity

✅ How to build IP, not just content

✅ The biggest mistakes creators make when trying to “monetize” too early

✅ How Dude Perfect thinks about longevity, leadership, and staying relevant

If you’re wondering how investors evaluate creator businesses, how leadership decisions change at scale, and why the future of media looks more like a modern entertainment company than a YouTube channel… then this episode is for you.

🐯👯‍♀️ 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

1:11: Welcoming Andrew Yaffe, Dude Perfect’s CEO

1:26: Three goals of the episode

1:52: Dude Perfect in a nutshell

2:25: The secret to a viral video 

6:36: Andrew’s approach as a leader 

7:10: Key learnings from working at the NBA

10:38: Applying International impact of sports to strategy 

13:33: Growth tips for new creators 

17:50: To trust or question the algorithm? 

21:00: Building a real business around content

22:24: Why Dude Perfect waited to raise outside capital

24:54: Playbook for developing new business lines 

29:45: What’s the value of live experiences? 

31:17: Measuring brand connection 

35:20: Longevity in a platform-driven world

36:33: Advice from the Dude Perfect story 

39:20: Mild or Wild questions with Andrew

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

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

What if the real dating glow-up isn’t playing hard to get, landing a rich partner, or mastering “feminine energy”… but learning how to regulate your nervous system, set clean boundaries, and stop shrinking yourself to be chosen?

In today's relationship-focused episode, Jean and Cherie sit down with one of the internet’s most influential dating voices, Sabrina Zohar (The Sabrina Zohar Show), to break down the psychology behind modern love. From “If I’m too much, go find less” to the question we’re all secretly asking - "Can ambitious women actually find love?" - this episode dives into what advice is worth keeping… and what might be keeping you stuck.

Tune in as they cover:

💥What “self-regulation” actually means

💥 The difference between boundaries and ultimatums

💥 Platonic vs Romantic boundaries 

💥 Early signs you’re shrinking yourself in dating

💥 Popular online "dating gurus" & what they're really saying

Whether you’re anxious, avoidant, healing, thriving, career-obsessed, freshly divorced, or wondering if you’re “too much”… this episode will challenge the stories you’ve absorbed about love and teach you how to choose yourself rather than strive to be 'chosen' first.

TIMESTAMPS:

00:51 - Introducing Sabrina Zohar 

2:20 - Defining self-regulation 

5:30 - How to actually self-regulate

9:30 - Pattern recognition in trauma triggers

12:12 - Discussing the fear responses 

13:40: How to co-regulate with a partner 

18:55: Exploring boundaries: Why they’re important and how to set them

21:49: The reason boundaries are so uncomfortable 

22:58: Setting boundaries in platonic friendships

26:50: Allowing yourself to sit with emotions 

32:39: Cherie’s friendship break-up 

36:20: “If I’m too much… find less” - how not to shrink yourself

43:45: Dating with detachment (from the outcome)

44:05: How to be in your growth stage

48:20: Analyzing “dating gurus” online 

54:48: Conclusion and lasting thoughts

🐯👯‍♀️ 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]

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

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

What if the fastest way to become a CEO isn’t launching a startup, climbing the corporate ladder, or building a personal brand, but buying a business that already works?

In this episode of Tiger Sisters, Jean and Cherie break down Entrepreneurship Through Acquisition (ETA), also known as “M&A for Hot People,” and how people buy “boring” cash flow businesses that quietly create millionaires.

Tune in as we cover:

• Why “buy then build” can beat starting from zero
• Search funds explained, how they work, & who they are for
• The boring businesses that print cash and what to look for
• The biggest red flags, and who should not do this

Then special correspondent Codie Sanchez, the internet’s biggest advocate for buying boring businesses, joins Jean and Cherie for a big picture conversation about building financial freedom and how women can leverage their strengths to thrive as CEOs.

Whether you’re climbing the corporate ladder, an aspiring founder, a burnt out startup employee, or just curious about how wealth gets built outside of Silicon Valley & Wall Street, this episode will change how you think about ownership.

... because sometimes the hottest move is buying something boring 💅

Timestamps:

00:01:18 Our episode outline

00:01:55 Buying & then build the business

00:02:30 What is a search fund?

00:05:18 Jean’s experience with search funds

00:10:24 Factors to balance during acquisition

00:11:46 Stanford vs. Harvard search fund history

00:19:05 Who this is for and NOT for

00:19:57 Welcome Codie Sanchez

00:22:34 How to buy a business with $0

00:29:19 The risk for women in entrepreneurship

00:35:45 There is no last best deal

00:36:30 Learn on someone else’s dime

00:37:50 How women are losing as investors

00:44:09 Why women in business should wear makeup

00:48:20 Codie’s secret to negotiation

00:50:27 There are 3 types of men to negotiate with

00:55:54 Rollups and economies of scale

1:00:00 - Cherie’s traffic cone business anecdote

1:06:05 - Outro

🐯👯‍♀️ 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]

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

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

Is single actually the new power move? Or are we collectively living through a full-blown Relationship Recession? Or can both things be true?

In honor of "Galentine's Day," Jean and Cherie take you through another in-depth 'Cultural Investigation' where they trace the evolution of what a "woman should be" — from housewife, to rebel, to Girl Boss, to Trad Wife — and land on a potentially new archetype: the Successful Single Woman. 

 🔎Along the way, they break down:

- How 1st, 2nd, and 3rd wave feminism have shaped women’s options and expectations

- Why we’re seeing record levels of singlehood across genders 

- What Bumble founder Whitney Wolfe Herd represents in the “have it all” era

- How dating apps, modern burnout, and rising standards are changing what people will tolerate in love

And make sure to stay tuned for Jean's first ever "Recession Lesson" where she applies economic recession frameworks to relationships and shows why you DON'T need to be fully depressed about our 'Relationship Recession' 🤓

Whether you’re single, coupled up, in a situationship (hopefully not), or exploring other unconventional partnerships: this one’s for you.'

Timestamps

00:50:  Introduction + Focus of Episode 

1:20: Stats about Singlehood 

1:45: Female Archetypes throughout history 

3:57: SoFi Ad 

4:25: Origins of “Galentine’s Day”

5:11: Defining 1st, 2nd, and 3rd Wave Feminism 

7:40: 4th Wave Feminism & the freedom to choose an archetype

8:46: Case Study of the “OG Girl Boss” - Whitney Wolf Herd

11:57: Girl Bossing too close to the sun 

13:13: The Resurgence of the “Trad Wife”

14:05: The ability to choose your own archetype 

15:47: SoFi Crypto Ad 

16:34: Introducing the Relationship Recession (facts & figures)

19:20: Challenging the idea that having a boyfriend is “embarrassing”

22:11: Jean’s “Relationship Recession” Lesson 

24:10: Solutions for the Relationship Recession 

26:57: Cherie applies the “Pattern Interruption’ framework to dating

32:04: Cherie’s takeaways from the episode 

34:10: Jean’s takeaways from the episode 

35:06: Explaining a “celebration cake” to celebrate small wins 

36:05: Conclusion

🐯👯‍♀️ 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]

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

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

Is the “Male Loneliness Epidemic” actually an epidemic, or is there something else going on here? Are men actually lonelier than women, or just louder about it? Why is male loneliness framed as a public crisis, while female loneliness is treated as a private burden? After examining the increase in loneliness across the board, Jean and Cherie sit down with first ever “Male Correspondent,” Ron Busby, to learn more about his experiences and ideate on solutions. 

This episode is for anyone who’s been affected by loneliness or isolation in one way or another, and anyone who wants to help build a more connected world.

If this conversation brings up difficult feelings or you’re struggling with loneliness or depression, you’re not alone. In the U.S., you can call or text 988 to reach the Suicide & Crisis Lifeline — a free, confidential support line available 24/7

📖 Additional Resources from Ron:

For men:

The Will to Change—by Bell Hooks

The Adonis Complex—by Harrison Pope

Masculinities—by Raewyn Connell

Giovanni’s Room—by James Baldwin

For women:

We Should All be Feminists—by Chimamanda Ngozi Adichie

The Second Sex—by Simone de Beauvoir

Gender Trouble: Feminism and the Subversion of Identity—by Judith Butler

For a better community:

Here for It—by R. Eric Thomas

Between the World and Me—by Ta-Nehisi Coates

Loneliness—by John T. Cacioppo

If you want to get involved in the work Ron is doing: 

@ronbusbyjr across all socials for personal updates

@seedthevote to get involved in volunteering (door knocking and talking to rural communities during election seasons; flights/hotels/rental cars covered.) 

 @byblack.us - Ron’s day job :)

🐯👯‍♀️ 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

0:00: Cold Open

1:12: Introduction 

1:36: Three action items for today’s episode 

3:57: Defining loneliness in its many forms

7:06: Scott Galloway on rising levels of loneliness in men

8:25: Male loneliness as a public vs private problem

11:05: Did Cherie just solve male loneliness via gardening?

18:18: Welcoming Ron Busby to the show

19:38: Male loneliness vs male alienation 

22:48: Defining the “manosphere”

27:50: Exploring an inclusive strategy to alleviating male loneliness

29:36 Defining a “Chad”

30:40: New beauty standards for men

39:00: Analyzing male loneliness in the dating world

40:45: Solutions for men and women to alleviate the issue

48:00 Lasting thoughts and key takeaways 

✅ 988 Suicide & Crisis LifelineCall or text: 988Chat: 988lifeline.orgAvailability: 24/7, free, confidentialThis is the gold standard right now. It’s not only for people in immediate suicidal crisis — it’s also for those feeling lonely, depressed, overwhelmed or supporting someone else who’s struggling. If you’re outside the U.S., visit findahelpline.com to locate a local support line in your country.

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

💛 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.

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

Learn more about your ad choices. Visit podcastchoices.com/adchoices