Trust Your Strengths (Not the Playbook) with Anya Cheng
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Trust Your Strengths (Not the Playbook) with Anya Cheng
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Anya Cheng has had a career most people would call “impossible” on paper: Sears, Target, McDonald’s, eBay, Meta and then the leap into founding her own company. In this conversation, Anya breaks down the real strategy behind those moves (and the mindset shift that changed everything): stop optimizing for “better” and start asking what you actually want.
We talk about playing the long game through community, referrals, and being a genuine connector (including how giving first helped her unlock key investor relationships). Anya also shares the origin story behind Taelor, an AI + human-stylist menswear rental that helps busy men look great without shopping or laundry, plus the surprising realities of fundraising as an immigrant woman founder and how she adapted without losing herself.
If you’re building your next chapter, this one is a reminder to leverage your strengths, stay in motion, and let courage look like your version of action.
Connect with Anya & Taelor:
🌐 Taelor: https://taelor.style
💌 Business partnerships / investors: anya@taelor.ai
🏷️ 25% off first month (menswear rental): POCAST25
🎁 10% off gift cards: podcastgift