Anya Cheng, founder and CEO of Taelor, and a former Head of Product for Meta, eBay, Target, and McDonalds, shares the absolutely insanely tenacious path of networking to her first job, getting to Silicon Valley by accepting a job in Minnesota, an eye-opening story about the prejudices that still exist in the startup world, how to turn office busywork into project management, how to amplify yourself by amplifying others, the value in finding out that your business may actually have a different clientele than you imagined (and why that's OK), and the TRUE way to eat oatmeal in Japan.

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This is Anya from here in Silicon Valley. I'm

running AI companies, and so excited to share more. And

before that, I led the E commerce team for Meta, eBay and

Target.

Wow, I wish you had an impressive background.

haha, just a lot of big tech companies. Facebook

shopping, was head of product for eBay's new business in the

US and new market in Latin America, Africa, Asia, helped

McDonald's to build a full delivery business when Uber eat

just started, and helped Target to move its tech office here in

Silicon Valley. But my personal entrepreneurship journey just

started less than three years ago in the AI spaces.

Absolutely. Well, I want to start with, if

you don't mind, let's go back just a smidge, because you do

have an interesting background. Just walk us through where did

this love for tech, all things e, if you will, related. Where

did that begin for you?

Yeah, so maybe I share a little bit. I came to

the US in 2007 went to Northwestern University for my

master degree in marketing. When I graduated, it happened to be

right after Lehman brothers, went bankrupt. So there was no

job anywhere. I remembered I was waiting outside of other

departments building to, as soon as the interviewer came out of

building, I was, hey, this is my resume. I am not even student of

these departments, but people say that, you know, Anya, this

is dumb, job searching is about networking, you shouldn't be

cold calling or ambush people. So I realized that I don't have

much connection. But that's not true. I do know professors, no?

I was a student, right? So I knock on the door of every

departments professor, I say, I'm a student here. This is my

resume. Please connect me to someone on LinkedIn who I

already researched. This guy talked to you on LinkedIn, so I

want to talk to him or her. And then one day there was a

professor say, I don't know you, I cannot connect you to anybody,

but tomorrow, I have a panel, and you are welcome to come as

students and to listen to the panel. By the way, we need more

students. Can you bring 10 more people? And so I went. I my

English was so bad I didn't understand anything in the in

the speech. But after that, I went out and talked to the

speaker. Hi, I'm Anya great job. Really good on the speech. I

have no clue what she was talking about, and this is my

resume. Can I talk to someone in your company running department

on digital? And she said, Yes. So I went on job interview. I

thought it was perfect, everything they were looking

for. A few weeks went by. Nobody contact me. I follow up with a

recruiter. The recruiter pick up phone. Asked me, please do not

call me anymore, because I was layed off. So the recruiter was

layed off from the company. So I said, Okay, you have nothing to

do? Do you want to come out for coffee? She said, Okay, why not?

So we had a coffee. She told me a lot going on about the

company, who is a decision maker, what's the challenge of

the company? And she also gave me an idea. Anya, Chicago is the

third largest city in the US. Do you want to go to New York? And

LA, they are bigger city there for probably more jobs. So I

went and I printed out 2,000 alumni from Northwestern

University. I started cold calling each of them. I said,

I'm coming to New York. I'm a student. Can I meet you for

coffee. And with that, I met with a lot of people, but

everyone say that I am not hiring. So I call a company in

Taiwan, a magazine. I say, Hey, do you want to cover these

amazing conferences for stories in New York? They say, yes. I

say, I can be a reporter for free. And I call the conference

say, Hey, I'm a reporter from Taiwan. Can you give me a press

ticket? And I got into a conference, and end up I met

with a lot of people, so I called the companies, the

magazine company CEO again, I said, I learned a lot from your

competitor, and do you want to know what they are working on?

She said, Yes. Before I go, I put together a business plan,

because I remember I met with a recruiter who was layed off. So

I went on interview there. You need someone who knows a little

bit marketing, a little bit digital, ideally, not very

expensive, just out of college? And I know someone: me! So she

asked me, Do you want to be a contractor? Anyway, that's how I

got my first job.

Absolutely, incredible. What an incredible

story. And I've just got to go back and pick out a couple of

nuggets of things that I think really speak to your creativity,

your insatiable work efforts and desire for the outcome. I mean,

you're a masters student at Northwestern, that should be

enough to get you a job, but to your point where, you know, we

just launched the financial crisis of '07, '08, '09, you

take your time. You went face to face asking for researched

LinkedIn connection introductions. Do you know that

has got to put you in the like 0.01% of the population that

uses LinkedIn?

In fact, what I found most effective during the

search was actually one time I was rejected again. I walk out

the building. I was in a newsstand, so I saw there were

newspapers. And on the newspaper, what do you say? It

say publisher name, so and so, if you want advertise, call this

number. So I bought all the newspaper, and then I start

calling each of them. And somehow, for some reason, I was

able to actually get on and talk to New York Times, CEO senior

and VP and SVP, of like ESPN, all of those companies.

That is incredible. Talk about

determination. Holy Hannah. So then, did I hear you say you

printed out a list of 2,000 alumni and started calling them

all?

Yeah. And then my English was so bad I didn't know

even how to talk to them. So I went to a senior care center

near campus, and I practiced my interview with those seniors,

because you can... no one will judge your English. You spend

time with them. So that's how I did my interview practice. My 93

years old. Her name is Connie. She's from Japan, and I still

remember she will put the soy sauce into the oatmeal because

she said that's how she eat breakfast back in Japan.

So okay, so if you learn nothing else, if you

want to, you know, be like a true Japanese oatmeal eater,

you're going to want to put soy sauce in that. Got it, check.

So your first job is with this magazine. Take me on your

journey from there.

Yeah, so I was there for a few years, and I was

mostly focused on digital part of a business. At that time, I

didn't know what that means, like product manager. Then I

joined Sears, and Sears was looking for someone who helped

on deciding where to buy on digitally. So with my magazine

background, they feel like, Oh, great. Then you have the media

side the background. Now you can be the buyer side the background

to see, help us to evaluate where you would you buy media.

And while I was doing that quickly, we discovered the most

effective way of buying media is using data. And after I doing

that for a few, for a year or two, they say, Hey, Anya, when

they come to my website, the homepage. It doesn't make sense.

Would you like to come and help us to personalize our homepage

and websites? And that's how I started my career in product

management. And from there, Target hired me. I remember that

they they asked me if I want to move to Minnesota. I didn't want

to, but I say...

No, actually, I have no desire to go to

Minnesota. Thank you. Yeah.

Yeah, thank you. But, yes, my career goal at the

time was coming to Silicon Valley. So I was looking for a

job in Silicon Valley, but Target came to me and they say,

Hey, Target is cooler than Sears and Kmart, so you should come

join Target. So I accept the offer. I went to Minnesota. They

call me. Anya, I remember you say you don't want to come to

Minnesota. I said, Yes, yes, yes. They say, You know your

managers role was opening. But now I found a guy, but the guy

should be based in San Francisco, and he doesn't want

to move to Minnesota. But now, since you have a manager there,

you can actually work there. And that's how I actually moved to

the Bay Area, by saying yes to something that wasn't relevant

to the Bay Area yet at all. And from there, I help Target to

build their tech office here in the Bay Area. McDonalds come to

me, they say, it's amazing. You launch your tech office here in

for Target, you launch your apps. You won 11 a word Best App

of the Year by Apple. Can you do the same for our E commerce

team? We want to launch something for food delivery

globally, and you will be able to do similar things and help us

launch office here. And that's what I did. And then eBay came

to me. So I joined Ebay. I helped them to focus on product

for Africa. And then eventually the Meta came to me. They say,

Hey, you have experience in Africa. Do you want to go to

places in Africa that does not have internet? So, Nigeria,

Kenya, Tanzania, Uganda? That was my job. When I joined Meta,

helped bring internet to country does not have internet. But then

during that time, I realized that social commerce is big

game, live streaming and Tiktok shopping, and everyone is

talking about social commerce, shopping on social media. And I

realized that I did have a lot of E commerce experience from

eBay and McDonalds and Target. So they're like, Hey, why don't

you come and help just to build Facebook shopping. And that was

how I ended up my last job in big corporate was Facebook

shopping.

Okay, so just for some of our listeners, can

you just share with us what were some of the ways that you

overcame the challenges of being female, of being Taiwanese, the

language barrier, the stereotype barrier, the prejudices that we

just know are out there, intentional or unintentional,

other than just incredible determination and work, how were

some of the ways you were able to come overcome some of those

challenges?

I actually feel a little bit less of that before I

became a startup founder, but it's actually a lot more. You

can tell a lot more after becoming startup founder. In

the startup world today, in the US, there are 30% of us

businesses were founded by female. Where female, at least

one of the founding members female. In the US, 15% and in

the Bay Area, for tech companies, 30%. However, for VC

backed company, for VC money, only 1.8% goes to female founded

company, 1.8% it's actually down from two years ago, 2.1%. I

remember a month ago, I went on a startup competition, and one

of the finalists, she was actually really nice and she got

her hair up. So she was on the stage with 1000s of people, and

then I said, Wow, nice dress, nice hair. And I also love your

accessories. This is an amazing ring, like giant diamond ring.

And she was like, you know, I'm not married, and I wear this

because research shows women who are married, people trust them

more because someone trusts them. That's why I wear the ring

going on competition. I was totally in shock. And she is

white woman who has 15 years of career, very, very successful,

even she will have to put on the ring for the competition. So at

the beginning, I felt pretty disappointed. And then one day,

I thought of, you know, what, if people the world only give me

opportunity because I'm a minority, if only minority will

give me an opportunity, then I go or go find minority

investors. So I start talking to people who are Nigerians and

Kenyans and Italians and Spanish and from Mexico and from

different part of the world, and Paris and Singapore and Taiwans

and Japan. If I can combine every minority investors to be

my investor, I have more than enough. I am majority, right?

But throughout my career, in corporate, there are some tips

to share to people. For example, people tend to assign

miscellaneous work to woman, and the best way is not actually

saying no, because people hate you, like you're like, hey,

Anya, can you order lunch for us tomorrow? Can you host the

holiday party for the office? It's kind of hard to say no, but

what you can do is you say yes, but then you start putting

together a rotation plan, yes, yes. I will help. But then,

okay, week one is this person, okay, you will do this. Week two

is this person will do this. Week three, you're organizing,

but you don't do it yourself. You're organizing. So you plan

as project management, or, for example, people hate woman to

promote themselves, so always amplify each other. And this

when you are in the meetings and you say, okay, great, just

Stephanie, I really agree, and I want to echo Stephanie's point

of view. You help her, she will help you. And then amplify

people don't want to hear you promote yourself, but they will

listen to you when you promote others. And also, for example,

you can at a certain event that you know they are very few

women, and you can organizing it in a way that they will stay.

For example, you know that this is the tech competition that

usually less women participate. But then before that, you have a

company all hands, and in the end, you say, Okay, we have this

tech event right after. I encourage everybody to stay so

create an environment that's easy for women or minority to be

able to participate. And also, you know, guys, they actually

hang out with co workers on weekend, while women tend to

hang out with people who are nothing to do with their work on

weekends, you know the loose ties will help. So next week,

find someone who you are not very familiar with. Ask them for

lunch. Just a simple step, the loose tie will be able to give

you insights and secrets in the office or industry that can help

you. So invite someone who you are not very familiar with next

week for lunch.

Very tactical, super practical. So now let's

talk about where you're at today, owning your own business,

working with AI, share with us a little bit about that journey.

Yeah, I'm now running an AI company called

Taelor, and it's a company we use AI to pick clothes for men.

I actually constantly feel a little bit impostor syndrome. I

was the only few female leader in tech that didn't come from

engineering background, but lead large technology teams. So I

want to look great, and I try some subscription boxes, but you

have to buy and I didn't want to own that much stuff. And I don't

have fashion sense. I don't know which one looks good. I have to

decide, because it's a new item. So I have to think, can I buy

this in some other places that will be cheaper? And then I

also, if I buy it, I will have to do laundry and ironings, and

I don't want to do any of those things, so I try some rental

company, but most of them require you to browse through

1000s of items. It was a hard moment that I realized most of

fashion companies are designed for people who are into fashion.

They're not for people like me. I'm just a lazy person or busy

person who need to do good, want to be successful, but does not

care about fashion. I need to do good for my job, for my day, for

my work. I do not care if I wear red or blue. All I care is that

I am successful in the next meeting. I close the deal. I do

well in the social events. I did well in my TED Talks. So I start

wondering is, are there people like me? Hate shopping, hate

laundry, but very purposeful and need to look good? Yes, they are

busy men. They have no idea how to look good, but they need to

look good. And turns out that we are a menswear business, but to

serve them, you need service. You need to pick clothes for

them. But before Gen AI, it wasn't feasible. You have to

hire someone, spend hours and 1000s of dollars and buy the

clothes and someone style you, but now with AI three seconds.

AI can pick perfect outfits and become your personal stylist,

and that's how we started.

That is so cool. Okay, anything that we haven't

talked about that you were hoping to address in our time

today?

Yeah, I think it's just for people who want to try

something a little bit more like looking good and saving time and

feel confident, if you are also a business, who have something

that you can partner with us, we would love to see what we can do

with each other. For example, we partner with dating sites, we

partner with coaches, and we also partner with fitness

centers and people losing weight. And you don't need to

buy large, medium, small clothes. And you can actually

just rent the clothes during the journey, and eventually buy the

clothes or look great after you work out and you dress up. So if

you are any of those business, feel free to reach out. And I'm

at anya@taelor.ai that's a, n, y, a, at, T, A, E, L, O, R, dot,

a, i, and we would love to work with you and help to save the

environment.

Thank you so much for being here with us.

What an incredible story and journey. And I really love the

way that you're not just taking this passion for business, but

you're also combining it with your passion, as you said, for

sustainability, doing good in the world. Just thank you so

much for being here.

Thank you so much.