Be Dumb to Succeed (the secret according to two-time Y Combinator founder Vu Tran)

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! ------------------------------------------------------------------ 🐯👯‍♀️ 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 💛 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 ⏰ 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 🥰