Enhancing Productivity Through AI and Startup Insights

In this season opener, Jean and Cherie sit down with David Shim—former CEO of FourSquare, founder of Read AI, and the entrepreneur who sold his startup to Snapchat for $200M. He reveals how he overcame relentless rejections, launched his first business at age six, and why “letting it wash off you” can be a superpower in sales. Stick around for Jean and Cherie’s post-interview debrief, where they break down their biggest takeaways, share personal stories that connect with David’s journey, and offer practical tips you can apply to your own business or career. Don’t miss this eye-opening start to our new season of interviews with game-changing CEOs, entrepreneurs, and leaders!

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🐯👯‍♀️ Tiger Sisters Podcast | Career, Entrepreneurship, and Life

Welcome to Tiger Sisters, your go-to podcast for career mentorship and life guidance! Hosted by Cherie Brooke Luo and Jean Luo, we’re your internet big sisters here to demystify the ups and downs of navigating careers, tech, and entrepreneurship— all while staying healthy, stylish, and joyful along the way.

Cherie is an influencer who has broken down the complexities of big tech, finance, and MBA programs for millions of viewers, with over 100M+ views across platforms. Jean is a tech product executive and investor, holding over 50 AI patents, who has built an impressive career in product management and institutional investment at companies like Goldman Sachs and Snapchat.

Between the two of us, we’ve survived stints at top investment banks and big tech firms, founded startups, and earned four Ivy League degrees—if we’re counting Stanford! Yet, we still find time to focus on wellness, friendships, fashion, and skincare, always sharing the lessons we've learned along the way.

Whether you’re here for career advice, stories about balancing life’s challenges, or just to hear our honest takes on what it means to pursue fun, wealth, and joy in all areas of life, we’ve got you covered.

🍿 WATCH NEXT: 

Tiger Sisters Season 2: 

Our Upbringing as Harvard & Stanford MBA Grads [S2 EP1]

https://www.youtube.com/watch?v=ylbt-kqkPGk&t=13s 

Tiger Sisters Season 1: 

Networking 101 from Harvard & Stanford MBA Grads [S1 EP 10]

https://youtu.be/q2D1agAvgkw?si=syXSqjCohGplfdH_ 

Cherie’s Corner: 

Roelof Botha: Career & Personal Lessons from Sequoia Capital Managing Partnerhttps://youtu.be/5s9Y5c6OXzs 

The Internet’s Big Sister and Career Mentor: Jean Luo

https://youtu.be/V_J236VrkrY?si=aSukqYXTOvb5Z4Li 

💛 LET'S CONNECT: 

~ CHERIE ~

🤳🏻 Instagram – https://www.instagram.com/cherie.brooke 

📱 TikTok – https://www.tiktok.com/@cherie.brooke 

✍🏻 My Substack – https://cherieluo.substack.com/ 

👩🏻‍💻 LinkedIn – https://www.linkedin.com/in/cherie-luo/ 

~ JEAN ~

🤳🏻 Instagram – https://www.instagram.com/jeanluo_/

👩🏻‍💻 LinkedIn – https://www.linkedin.com/in/jeanluo 

🎵 Music produced by Sammy Signal https://open.spotify.com/artist/2HsyknHuxhT8RoZfn5rqMS

🛍️ Items Referenced:

🍵Sisters Matcha & SISTERS Merch:www.sistersmatcha.com

✨Tiger Sisters & Friends Japan Trip (May 2025):https://trovatrip.com/trip/asia/japan/japan-with-cherie-luo-may-2025  
♠️ Everything else:https://amzn.to/3z0dx5b

⏰ Timestamps:

00:00:00 – Season 3 Premiere & Introduction

00:02:38 – Meet David Shim: Entrepreneur Since Age Six

00:10:58 – “Throw Yourself Into it As Much as You Can” 

00:13:01 – “Forget Very Quickly”: Turning Rejection into Fuel

00:14:50 – Why Competition Can Be A Good Thing (Especially in AI)

00:16:08 – “You Were the Worst”: Nearly Flubbing the $200M Snapchat Deal 

00:24:56 – Jean & Cherie’s Debrief: Our Biggest Takeaways

00:46:03 – Wrap Up & Please Like, Comment, Subscribe, and Rate Us 5 Stars!