Innovating in Style, with Anya Cheng – Episode 484 of The Action Catalyst Podcast

Anya Cheng is the 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.

About Anya:

Anya Cheng is a Taiwanese American technology executive and entrepreneur in Silicon Valley. Before launching her artificial intelligence (AI) startup, Taelor, she helped build Facebook Shop, a social commerce initiative where people can explore and purchase products directly on Meta (formerly Facebook) and Instagram. Before that, she led the go-to-market for Facebook’s Wi-Fi Tech and Innovation team where she improved digital literacy by bringing the Internet to countries without fast connections. As Head of Products, she transformed eBay Classifieds’ emerging business and built Target’s mobile tablet eCommerce app. As McDonald’s Senior Director of eCommerce, she launched their global food delivery apps from scratch.

Cheng is currently Founder & CEO of Taelor, a AI-powered menswear rental subscription platform busy men to rent styles and for brands/retailers to test products and predict trends. Taelor is an award-winning sustainability startup that has won various competitions hosted by accelerators including Draper University, University of Chicago Polsky Center and SPARK Accel.

Cheng is also an adjunct lecturer at Northwestern University and 500 Global (formerly 500 Startups) where she teaches software product management and marketing. She is the author of a best-selling career book, a TEDx Talk speaker, and a social media influencer.

Cheng was named a Girls in Tech 40 Under 40 in 2018 and nominated as a Marketer of the Year by Min Magazine U.S. in 2013. Her work has won 20+ awards including the Webby Award Best for Shopping App, The Communicator Award, and the Rising Star Award of Social Network Category by Mobile Village. She is a volunteer career coach who has inspired thousands of young professionals and currently serves on the volunteer boards for the North America Taiwanese Engineering and Science Association, Taiwan Tech Arena (a non-profit supporting minority founders) and STUF United Fund (a non-profit supporting charitable causes.)

Cheng received her MBA from the University of Chicago Booth School of Business and a Master of Science degree in Integrated Marketing Communications from Northwestern University. 

The Action Catalyst is presented by the Southwestern Family of Companies. With each episode, the podcast features some of the nation’s top thought leaders and experts, sharing meaningful tips and advice. Learn more at TheActionCatalyst.com, subscribe below or wherever you listen to podcasts, and be sure to leave a rating and review!

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(Transcribed using A.I. / May include errors):

Anya Cheng
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.

Stephanie Maas
Wow, I wish you had an impressive background.

Anya Cheng
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.

Stephanie Maas
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?

Anya Cheng
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.

Stephanie Maas
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?

Anya Cheng
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.

Stephanie Maas
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?

Anya Cheng
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.

Stephanie Maas
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.

Anya Cheng
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…

Stephanie Maas
No, actually, I have no desire to go to Minnesota. Thank you. Yeah.

Anya Cheng
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.

Stephanie Maas
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?

Anya Cheng
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.

Stephanie Maas
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.

Anya Cheng
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.

Stephanie Maas
That is so cool. Okay, anything that we haven’t talked about that you were hoping to address in our time today?

Anya Cheng
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 [email protected] 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.

Stephanie Maas
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.

Anya Cheng
Thank you so much.