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Grab your matcha, Tiger Fam because this week we're getting personal. 💔

Today, we're breaking down the Top 5 Lessons We Learned From Our Exes: the red flags we ignored, the mistakes we made, and the hard truths we wish someone had told us sooner. Because as we always say: relationships aren't just emotional, they shape your confidence, your finances, and your career trajectory too.

Think of this episode as a public service announcement from our former selves.

Tune in for:

✅ Why putting someone on a pedestal is actually a decision-making problem

✅ The real reason age-gap relationships can go sideways

✅ Why dating for money is the wrong move (and what to look for instead)

✅ The golden rule: Don't sh*t where you eat (we learned this one the hard way)

✅ How to spot a love bomber before you're already in too deep

Every lesson comes backed with psychology, research, and our own lived experience, because your love life deserves the same rigor you'd apply to any major life decision.

Consider this your relationship due diligence guide. Let's get into it. 🐯

Timestamps:

00:48: Episode Intro

02:08: Lesson #1: Don’t put anyone on a pedestal

02:50: Jean’s personal anecdote

07:28: Why it’s dangerous to put someone on a pedestal

09:00: The business lesson (don’t put founders on a pedestal)

12:12: How to know if you’re putting someone on a pedestal

13:08: Lesson #2: Mind the age gap

13:36: Cherie’s personal anecdote

16:13: Jean’s personal anecdote

24:54: Why the age gap matters in different life stages

26:21: Lesson #3: Don’t date for money: date for track record

31:17: What to look for in a partner *outside* bank account

32:45: Lesson #4: Don’t sh*it where you eat

33:37: 3 major risks of workplace relationships

34:10: Cherie’s personal anecdote

36:05: Why it’s difficult to work with friends

39:00: Lesson #5: beware of the love bomber

39:20: Jean’s personal anecdote

43:30: What to do if you’re being love bombed

45:30: The importance of boundaries

48:08: Conclusion and lasting thoughts

🐯👯‍♀️ We’re the Tiger Sisters — your Wall Street & Silicon Valley big sisters Decoding Money • Power • Love

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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

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Lessons From Our Exes: 5 Red Flags We Ignored

Tiger Sisters

Lessons From Our Exes: 5 Red Flags We Ignored