In this episode of Be Anomalous, founder and CEO of Yes Plz, Jiwon Hong, joins me for a conversation about second chances, shifting mindsets, and building a company the second time around with intentionality, humility, and soul.
Jiwon shares her journey from growing up in Korea and moving to South Carolina in high school, to working at companies like Sony Music and Samsung, to launching not one, but two startups, learning to talk to customers, embrace failure, and build a recommendation engine rooted in real human behavior.
We talk about what it means to unlearn perfectionism, how cautious people can still take big risks, and how founders can use AI not just to build products — but to build themselves.
If you’ve ever wrestled with doubt, struggled to sell your ideas, or wondered if you're “doing it wrong,” Jiwon’s story will remind you that success isn’t about being right; it’s about being willing to change.
🎧 Listen to the episode
Spotify | Apple Podcasts
What you’ll learn
How Jiwon turned failure from her first startup into insight for her second
Why not talking to customers nearly sank her first business
The subtle but profound differences between the Korean and American work cultures
How she used ChatGPT to improve her sales strategy — and got called out
Tactical lessons on customer discovery, cold outreach, hiring, and pivoting
Why scaling means finding your own playbook, not copying someone else’s
The mindset shift from “being right” to “getting it right”
Favorite Quote
“As a founder, you have to find your unique path to success. If the playbook is already known, someone with more money and a bigger team will already be doing it.”
— from Blitzscaling by Reid Hoffman
Favorite Book
📖 Blitzscaling by Reid Hoffman
In this episode, we cover:
(00:00) Welcome and background — from Korea to South Carolina
(03:00) Cultural differences and how they shaped her mindset
(06:00) Studying economics and learning analytical thinking
(08:00) Her first startup — and what went wrong
(12:00) The decision to give entrepreneurship one more try
(15:00) Founding Yes, Please, and discovering a better way to shop online
(18:00) Bringing on her husband as co-founder
(20:00) Raising funding — why it happened faster than expected
(23:00) Getting first customers and building product-market fit
(27:00) Letting go of “being right” and embracing adaptability
(30:00) Her strength: doing things that make her uncomfortable
(32:00) Her weakness: being overly cautious — and how she works through it
(34:00) Hiring tips and what she looks for in early team members
(37:00) Sales lessons: how she changed her pitch and started converting
(39:00) Using ChatGPT as an honest sales coach
(41:00) The real AI advantage isn’t tech — it’s knowing your customer deeply
(44:00) Advice for new founders in an AI-saturated market
(47:00) Building a founder community — and how to start your own
(49:00) Her favorite book, quote, and biggest mindset shift
Where to find Jiwon Hong
Referenced in this episode
Startup Grind
ChatGPT for founder feedback
AI recommendation systems for retail
