In this episode, the Tiger Sisters interview Vu Tran, two-time Y Combinator founder and CEO of Butterflies AI, The First AI Social Network. Join us to learn about how questioning constraints and breaking rules helped him launch two startups before turning 22, why being dumb led to his success today, and how he continues to apply his “go max dumb” mindset.
Let’s get vulnerable together as we talk about Vu’s upbringing and why he considers poverty to have been a gift – and why embracing your roots might be your greatest advantage, too. Don’t miss our debrief at the end with just Jean and Cherie where we talk through our favorite learnings from Vu like an HBS case study for even more insights!
Our japan trip: https://trovatrip.com/trip/asia/japan/japan-with-cherie-luo-may-2025
------------------------------------------------------------------
🐯👯♀️ 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 3:
Facing Rejection to Selling His Startup for $200 Million: David Shim's Founder Mindset
https://youtu.be/tWxcgyd051c?si=ax60mnLAGKXo_uw4
Tiger Sisters Season 2:
Our Upbringing as Harvard & Stanford MBA Grads
https://www.youtube.com/watch?v=ylbt-kqkPGk&t=13s
Tiger Sisters Season 1:
Networking 101 from Harvard & Stanford MBA Grads
https://youtu.be/q2D1agAvgkw?si=syXSqjCohGplfdH_
Cherie’s Corner:
Roelof Botha: Career & Personal Lessons from Sequoia Capital Managing Partner https://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
🔮 Exhalation by Ted Chiang: https://bookshop.org/p/books/exhalation-ted-chiang/8605278
⏰ Timestamps:
00:00:00 – Welcome from Cherie and Jean 👋
00:01:57 – Meet Vu Tran: 2x YC Founder & CEO of Butterflies AI
00:03:04 – Questioning Constraints: Which Rules Are Worth Breaking
00:05:26 – “Don’t have the same regrets as me.”
00:06:25 – “Go Max Dumb”: How Vu Operates
00:10:09 – Refugee Camp Roots to First Job
00:11:16 – Vu’s Big Wake Up to See Two Paths in Life
00:13:23 – History: Interracial Marriage to AI-Human Romance
00:17:40 – Jean & Cherie’s Deep Dive Debrief
00:18:17 –Having Nothing Made him Unafraid
00:21:36 – Jean applied Vu’s advice of questioning constraints as a product manager
00:24:00 – “Go Max Dumb” at business school & when leading teams
00:27:34 – Zuck + Sheryl Sandberg as a great “Max Dumb” success story
00:29:00– Saying “If I had a time machine” vs “I regret”
00:31:35 – Jean’s process of “waking up” via a sabbatical
00:35:56 – We’re ready to meet our future grandchildren’s AI boyfriends
00:37:50 – Jean’s book recommendation: Exhalation by Ted Chiang
00:39:17 – Why everyone is obsessed with Japan – join our Japan trip in May 2025!
00:41:29 – Until next time! Rate us ⭐️⭐️⭐️⭐️⭐️ and leave us a review 🥰