The CTO Show with Mehmet Gonullu #475 Focus, Grit, and Product-Market Fit: Lessons from Anya Cheng’s Startup Journey
In this episode, Mehmet sits down with Anya Cheng, the founder and CEO of Taelor, a fashion-tech startup revolutionizing how busy men dress—without shopping or doing laundry. With past leadership roles at Meta, eBay, and McDonald’s, Anya brings a unique product mindset and startup resilience that shines through her journey from MVP to raising millions.
This is a masterclass in product thinking, perseverance, and staying focused—even when things get scrappy.
🔑 Key Takeaways
• Start with real customer pain, not tech buzzwords
• Use product intuition and lean MVPs to validate ideas
• Why storytelling and empathy beat sales tactics in fundraising
• Fundraising is less about pitching, more about training champions
• Deep customer insight is your competitive moat
🎧 What You’ll Learn
• How Anya applied agile principles to build Taelor from a landing page
• The truth about launching AI products in fashion
• Lessons from her time at Meta, eBay, and Target
• How to approach investors with authenticity and relevance
• Why female founders and minority-led teams should lean into their strengths
👤 About the Guest
Anya Cheng is a serial builder and product leader turned founder. As a Mentor at '500 Startups' and ex-product leader at McDonald, eBay and Facebook, she has been listed in 'Girls Tech 40 Under 40' and founded a sustainable men clothing rental platform- Taelor (currently doing $1.5m in revenue).
She’s also a TEDx speaker and a mentor at 500 Startups.
At Taelor, she’s building “Netflix for menswear,” using AI to deliver rental clothing for men who want to look great without effort.
Use code PODCAST25 for 25% off your first month!
https://www.linkedin.com/in/anyacheng/
🧭 Episode Highlights
00:02 – Anya’s background and the aha moment behind Taelor
00:07 – Early MVP experiments and Taelor’s first 100 customers
00:12 – GTM lessons from Meta, eBay, and Target
00:15 – Knowing when to follow data—and when not to
00:18 – Building a product team with complementary pieces
00:22 – What Anya looks for in startup founders as a 500 Startups mentor
00:26 – Fundraising stories and mindset reframes
00:34 – Solving for a focused use case instead of chasing features
00:39 – Her perspective on being a female founder in tech
00:42 – TEDx behind the scenes and tips for pushing through hardship
00:47 – Mehmet’s reflections on podcasting, persistence, and building in public