Podcast Summary

Episode Overview

Podcast: Neuro Performance by Andy Murphy
Episode: 445: (Interview) From Facebook & eBay to AI Entrepreneurship: Anya Cheng’s Journey to Disrupting Fashion & Tech
Guest: Anya Chen (Founder & CEO of Taylor)
Published: February 5, 2025

In this episode, Andy Murphy sits down with tech veteran and AI entrepreneur Anya Chen, whose career journey spans product leadership at giants like Facebook, eBay, Target, and McDonald’s, and her bold leap into fashion tech as the founder of Taylor, an AI-powered menswear subscription service. The conversation explores Anya’s personal immigrant story, her methods for managing high performance, the challenges of startup life, and her vision for making life easier—and more sustainable—for professionals through technology.

Key Discussion Points & Insights

1. Origins and Emotional Drive

[05:43] Anya’s background: Grew up in a blue-collar family in Taiwan, moved to the US 17 years ago, and faced language and cultural barriers.
Immigrant resilience: Shared humorous and poignant anecdotes about misunderstanding English (“Are you seeing someone?” “No, I don't see anyone behind me”) and struggling with job rejections.
Motivational story: Described a low point in New York: “my teardrop on the rice because it was such a simple and family meal back in Taiwan. But here it seems everything is so hard.” (Anya Chen, 07:10)
First break: Persistence led her to cold-call thousands of alumni and businesses: “I start calling every single newspaper. Hi, I'm interesting… eventually I actually met with New York Times CEO and all their company’s executive.” (Anya Chen, 08:38)
Mission: Her drive isn’t just about money, but about helping others be “the best version of themselves without worrying about things they shouldn’t.” (Anya Chen, 11:44)

2. Career Path Through Tech & Big Brands

[13:42] Recap of roles: Led Facebook/Instagram shopping at Meta; Head of Product at eBay; Senior Director at McDonald’s; pioneered at Target.
Impact: Helped build and transform multi-billion dollar departments and was pivotal in international expansion.
Cultural leadership: Often the only woman and minority in leadership (“the only minority and also only woman head of product in the company” at eBay).

3. Managing High Performance & Mental Health

[14:37]–[18:32] Switching hats: Learned to change mindsets for different task types—analytical, creative, execution—especially after COVID blurred work-life boundaries.
Daily habits: Sets a single key intention for the day instead of overwhelming to-do lists.
Recharge routines: Uses a deliberate “half-time” break each afternoon and treats herself like an athlete: “I try…definitely horrible in the running and everything, but I try.” (Anya Chen, 17:30)
Burnout: Calls “timeouts” and embraces rituals like swimming and ice cream breaks to restore energy.
Mental health awareness: “You probably always feel that if it's not successful it's all because you haven’t worked hard enough—and the fact is just not true.” (Anya Chen quoting Andy Dunn, 20:31)

4. Startup Vision & Disrupting Fashion

[25:19] The “Taylor” concept: Not just another menswear subscription. Inspired by her own experience of imposter syndrome and the desire for effortless style for professionals—especially men who are “purposeful,” dislike shopping, but want to look good.
Uniqueness: AI (and human stylists) select rental outfits tailored to each customer; clients can purchase favorites at a discount. Aims to remove the friction of shopping and laundry.
Why menswear, from two women founders? Spotting the unmet needs of male professionals who don’t want to engage with fashion but still need to look sharp.
Social impact: Tackles fashion sustainability—“10% of clothes go directly from factory to landfill…by giving the rental model, people give feedback right away” helping brands predict trends and reduce waste (Anya Chen, 29:58–30:35)

5. Leveraging AI in Fashion Tech

[31:44] Tech evolution: “The era of algorithm is dead…in the era of AI it’s all about data—unique data.” Data from user preferences, clothing quality, and feedback loop with 300+ brands feeds into Taylor’s proprietary AI for improved recommendations.
Differentiator: Not just automated fashion picks; their AI is enhanced with future trend data, real feedback, and professional human stylists—creating an adaptive, unique customer experience.
Licensing model: Taylor's tech is being licensed to other brands for AI-powered styling and content, opening new revenue streams and partners.

6. Fundraising, Networking, & Advice for Founders

[40:35] Origin of VC support: “Sometimes, money is there when you are not looking.” Anya shared how authentic networking—helping others without immediate ask—led to critical investor introductions and a million-dollar investment.
Pitching insights: VCs “spend 2.5 minutes on a deck, 45 seconds on the team slide…not just about how cool you are but how relevant your team is to what you're building.” (Anya Chen, 43:40)
Strategic team-building: Emphasized the value of complementary skills, using a basketball analogy—“all-star” teams can fail, but “championship” teams win through diverse, needed skills.
Practical founder tip: Understand feedback by asking “why,” not just accepting “what”: “When people give you feedback, do not take the what, ask for why.” (Anya Chen, 49:45)
Believe in yourself: Recounted a pitch competition where over-preparation led her to fumble—urges founders to trust their expertise and “be yourself.”

Notable Quotes & Memorable Moments

On perseverance and the immigrant journey:
“As soon as the waitress served the dish, my teardrop on the rice because it was such a simple and family meal back in Taiwan. But here it seems everything is so hard.” (Anya Chen, 07:10)
On the Taylor mission:
“The mission for Taylor is not just about picking clothes for you, it’s about how can I help you to take one thing, even one tiny thing a month off your busy plate, so then you can focus on being the best version of yourself.” (Anya Chen, 11:44)
On using AI and data:
“The era of algorithm is dead…in the era of AI it’s all about data—unique data…when you pick the clothes with AI support, it’s what you truly love, not just because it’s in discount.” (Anya Chen, 31:44)
On high performance habits:
“I used to create a to-do list like this…very quickly the 3-item to-do list becomes 300…and then you just hate the list…In the morning I will ask myself, okay, what's one thing I have to get done today?” (Anya Chen, 17:30)
On founder mindset:
“I know more than what I thought as a founder. Like, you think about a problem 24/7, right? Probably you are one of the 10 people in the world who know this topic more than anyone else.” (Anya Chen, 48:05)
On authentic networking:
“You were genuinely just intrigued and interested…and you gave him value, right? You didn't ask for anything, you didn't take. And I feel so many entrepreneurs get that model wrong. They're all about just taking. There's no giving.” (Andy Murphy, 45:33)

Key Timestamps for Important Segments

05:43 — Anya’s origin story, tough immigrant journey
13:42 — Anya’s rapid career overview (Meta, eBay, McDonald’s, Target)
15:19–18:09 — Managing high performance, daily routines, “half-time” breaks
20:31–23:54 — Mental health, founder burnout, creating a “superpower” product
25:19 — The birth of Taylor and identifying the need for AI-powered menswear
29:58–30:35 — Fashion sustainability crisis, role of Taylor’s model
31:44–35:10 — AI’s role, data as the unique differentiator, licensing technology
40:35–49:51 — Fundraising stories, VC insights, team-building, practical founder advice
51:46–57:56 — Anya’s heart: Why helping others is her true motivation and the deeper mission behind Taylor

Tone & Style

Genuine, motivational, and practical. Anya balances humor, vulnerability, and technical depth while Andy Murphy’s warm and inquisitive style elicits behind-the-scenes wisdom, not just business success stories.

For Listeners

If you want to understand the intersection of tech, AI, and fashion entrepreneurship—and what it truly takes to build something from scratch as an outsider—this episode will inspire and equip you. Anya Chen’s journey is as much about grit and giving as it is about data, disruption, and high performance.

Discount Mention:
Taylor Style offers 30% off for the first month for podcast listeners—promo code: NEURO30.

[Podcast ads, intro, outro, and non-content were omitted from this summary.]

Podcast Summary

Episode Overview

Key Discussion Points & Insights

1. Origins and Emotional Drive

[05:43] Anya’s background: Grew up in a blue-collar family in Taiwan, moved to the US 17 years ago, and faced language and cultural barriers.
Immigrant resilience: Shared humorous and poignant anecdotes about misunderstanding English (“Are you seeing someone?” “No, I don't see anyone behind me”) and struggling with job rejections.
Motivational story: Described a low point in New York: “my teardrop on the rice because it was such a simple and family meal back in Taiwan. But here it seems everything is so hard.” (Anya Chen, 07:10)
First break: Persistence led her to cold-call thousands of alumni and businesses: “I start calling every single newspaper. Hi, I'm interesting… eventually I actually met with New York Times CEO and all their company’s executive.” (Anya Chen, 08:38)
Mission: Her drive isn’t just about money, but about helping others be “the best version of themselves without worrying about things they shouldn’t.” (Anya Chen, 11:44)

2. Career Path Through Tech & Big Brands

[13:42] Recap of roles: Led Facebook/Instagram shopping at Meta; Head of Product at eBay; Senior Director at McDonald’s; pioneered at Target.
Impact: Helped build and transform multi-billion dollar departments and was pivotal in international expansion.
Cultural leadership: Often the only woman and minority in leadership (“the only minority and also only woman head of product in the company” at eBay).

3. Managing High Performance & Mental Health

[14:37]–[18:32] Switching hats: Learned to change mindsets for different task types—analytical, creative, execution—especially after COVID blurred work-life boundaries.
Daily habits: Sets a single key intention for the day instead of overwhelming to-do lists.
Recharge routines: Uses a deliberate “half-time” break each afternoon and treats herself like an athlete: “I try…definitely horrible in the running and everything, but I try.” (Anya Chen, 17:30)
Burnout: Calls “timeouts” and embraces rituals like swimming and ice cream breaks to restore energy.
Mental health awareness: “You probably always feel that if it's not successful it's all because you haven’t worked hard enough—and the fact is just not true.” (Anya Chen quoting Andy Dunn, 20:31)

4. Startup Vision & Disrupting Fashion

[25:19] The “Taylor” concept: Not just another menswear subscription. Inspired by her own experience of imposter syndrome and the desire for effortless style for professionals—especially men who are “purposeful,” dislike shopping, but want to look good.
Uniqueness: AI (and human stylists) select rental outfits tailored to each customer; clients can purchase favorites at a discount. Aims to remove the friction of shopping and laundry.
Why menswear, from two women founders? Spotting the unmet needs of male professionals who don’t want to engage with fashion but still need to look sharp.
Social impact: Tackles fashion sustainability—“10% of clothes go directly from factory to landfill…by giving the rental model, people give feedback right away” helping brands predict trends and reduce waste (Anya Chen, 29:58–30:35)

5. Leveraging AI in Fashion Tech

[31:44] Tech evolution: “The era of algorithm is dead…in the era of AI it’s all about data—unique data.” Data from user preferences, clothing quality, and feedback loop with 300+ brands feeds into Taylor’s proprietary AI for improved recommendations.
Differentiator: Not just automated fashion picks; their AI is enhanced with future trend data, real feedback, and professional human stylists—creating an adaptive, unique customer experience.
Licensing model: Taylor's tech is being licensed to other brands for AI-powered styling and content, opening new revenue streams and partners.

6. Fundraising, Networking, & Advice for Founders

[40:35] Origin of VC support: “Sometimes, money is there when you are not looking.” Anya shared how authentic networking—helping others without immediate ask—led to critical investor introductions and a million-dollar investment.
Pitching insights: VCs “spend 2.5 minutes on a deck, 45 seconds on the team slide…not just about how cool you are but how relevant your team is to what you're building.” (Anya Chen, 43:40)
Strategic team-building: Emphasized the value of complementary skills, using a basketball analogy—“all-star” teams can fail, but “championship” teams win through diverse, needed skills.
Practical founder tip: Understand feedback by asking “why,” not just accepting “what”: “When people give you feedback, do not take the what, ask for why.” (Anya Chen, 49:45)
Believe in yourself: Recounted a pitch competition where over-preparation led her to fumble—urges founders to trust their expertise and “be yourself.”

Notable Quotes & Memorable Moments

On perseverance and the immigrant journey:
“As soon as the waitress served the dish, my teardrop on the rice because it was such a simple and family meal back in Taiwan. But here it seems everything is so hard.” (Anya Chen, 07:10)
On the Taylor mission:
“The mission for Taylor is not just about picking clothes for you, it’s about how can I help you to take one thing, even one tiny thing a month off your busy plate, so then you can focus on being the best version of yourself.” (Anya Chen, 11:44)
On using AI and data:
“The era of algorithm is dead…in the era of AI it’s all about data—unique data…when you pick the clothes with AI support, it’s what you truly love, not just because it’s in discount.” (Anya Chen, 31:44)
On high performance habits:
“I used to create a to-do list like this…very quickly the 3-item to-do list becomes 300…and then you just hate the list…In the morning I will ask myself, okay, what's one thing I have to get done today?” (Anya Chen, 17:30)
On founder mindset:
“I know more than what I thought as a founder. Like, you think about a problem 24/7, right? Probably you are one of the 10 people in the world who know this topic more than anyone else.” (Anya Chen, 48:05)
On authentic networking:
“You were genuinely just intrigued and interested…and you gave him value, right? You didn't ask for anything, you didn't take. And I feel so many entrepreneurs get that model wrong. They're all about just taking. There's no giving.” (Andy Murphy, 45:33)

Key Timestamps for Important Segments

05:43 — Anya’s origin story, tough immigrant journey
13:42 — Anya’s rapid career overview (Meta, eBay, McDonald’s, Target)
15:19–18:09 — Managing high performance, daily routines, “half-time” breaks
20:31–23:54 — Mental health, founder burnout, creating a “superpower” product
25:19 — The birth of Taylor and identifying the need for AI-powered menswear
29:58–30:35 — Fashion sustainability crisis, role of Taylor’s model
31:44–35:10 — AI’s role, data as the unique differentiator, licensing technology
40:35–49:51 — Fundraising stories, VC insights, team-building, practical founder advice
51:46–57:56 — Anya’s heart: Why helping others is her true motivation and the deeper mission behind Taylor

Tone & Style

For Listeners

Discount Mention:
Taylor Style offers 30% off for the first month for podcast listeners—promo code: NEURO30.

[Podcast ads, intro, outro, and non-content were omitted from this summary.]

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445: (interview) From Facebook & eBay to AI Entrepreneurship: Anya Cheng’s Journey to Disrupting Fashion & Tech

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Summary

Podcast Summary

Episode Overview

Key Discussion Points & Insights

1. Origins and Emotional Drive

2. Career Path Through Tech & Big Brands

3. Managing High Performance & Mental Health

4. Startup Vision & Disrupting Fashion

5. Leveraging AI in Fashion Tech

6. Fundraising, Networking, & Advice for Founders

Notable Quotes & Memorable Moments

Key Timestamps for Important Segments

Tone & Style

For Listeners

Summary

Podcast Summary

Episode Overview

Key Discussion Points & Insights

1. Origins and Emotional Drive

2. Career Path Through Tech & Big Brands

3. Managing High Performance & Mental Health

4. Startup Vision & Disrupting Fashion

5. Leveraging AI in Fashion Tech

6. Fundraising, Networking, & Advice for Founders

Notable Quotes & Memorable Moments

Key Timestamps for Important Segments

Tone & Style

For Listeners