Transitioning Roles: COO to CEO and Delegation

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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, incoming CEO of Bessemer Trust ($200B AUM).

his 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

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⏰ Timestamps01:27 - What Is a Family Office?

03:00 - Running a $200M AUM 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.brookeTikTok — /cherie.brookeSubstack — cherieluo.substack.comLinkedIn — /cherie-luo~ JEAN ~Instagram — /jeanluo_LinkedIn — /jeanluo

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