What does it take to sell your companies to both Apple and Discord? In this spirited episode, the Tiger Sisters chat with cybersecurity expert and serial entrepreneur John Redgrave—and his energy is totally infectious.

John opens up about how he wishes he took risks sooner, building an unstoppable work ethic, and why he believes anyone can become a master storyteller by learning from music, arts, and even corporate America.

He dishes on his favorite public speaking hacks (including a ChatGPT tip you can do today), and even reveals his hot take on how the U.S. stacks up against China in AI development.

Tune in for a fun, rapid-fire, no-fluff talk that just might inspire your next big leap!

note: Jean mentioned “Walter Mondale” but meant “Walter Cronkite” ;) 

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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.

💛 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 Cold intro: “No might be a gift”

00:01:14 Meet John Redgrave

00:02:08 John’s track record: Palantir, Apple, Discord

00:03:40 Advice to 29-year-old self

00:04:20 Becoming a powerful storyteller

00:05:56 John’s first job in the ‘90s

00:07:11 Micro-failures and reframing losses

00:09:37 “Sometimes no is better than yes”

00:11:27 John’s AI hot take (US vs. China)

00:12:27 Public speaking secrets

00:14:35 Using ChatGPT for media training

00:16:32 John’s travel picks

00:19:05 Tiger Sisters’ debrief: our takeaways

00:19:55 Jean’s favorite takeaway: public speaking

00:23:01 How to stay calm

00:25:41 Cherie’s favorite tip from John: storytelling

00:31:34 Seeking out micro-failures to level up