Lessons From Our Exes: 5 Red Flags We Ignored

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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
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▫️ 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
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