289. From Big Tech to Startup CEO: The Self-Trust Shift Every Woman Needs with Anya Cheng

This episode explores how true confidence is built through self-trust, mindset shifts, and leading with belief, especially when titles, validation, and certainty fall away.

Guest Anya Cheng is the founder and CEO of Taeler, an AI platform that uses AI to help men choose outfits, and rent them. Having led teams at big brands such as Target, Facebook, eBay, McDonald’s, she’s a Mentor at ‘500 Startups’, Lecturer at Northwestern University, author and a TED speaker.

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Hello, hello, beautiful souls. Welcome back to another episode on the Lucy Liu show. And I have a special guest with me today.

Anya Chan. She’s the founder and CEO of Taelor and AI platform that uses AI to help men choose outfits and rent them. Having led teams at big brands such as Target, Facebook, eBay, McDonald’s.

She’s a mentor at 500 startups lecture at Northwestern University author TEDx speaker. How amazing is that? Welcome to the show Anya.

Hello, hello, this is Anya. I’m here in San Francisco. I now run a company called Taelor AI.

So you’ve led all these teams at big brands, as you started your own company and got backed by VCs behind 20 plus unicorns. How has your definition of confidence evolved as you moved from a corporate leadership to a founder and CEO role?

I would say the confidence is up and down, right? So because when I work working for big tech companies, people tend to like to talk to you. When I have the Facebook business card, people say, Yeah, I want to do business with meta or with Instagram, where I want to, I want to apply for a job there seems that people always want to talk to you.

And throughout I’m an immigrant from Taiwan originally. So throughout the last 15 years, kind of starting from working for like no one heard of type of a magazine company all the way to meta and leading team. But then being a startup founders, the confidence was just gone.

Because when I became a startup founder, I’m a CEO of Taylor, which no one heard of before. So then when I go to meetings, or Chamber of Commerce networking events, people tend to talk to those big IPO founders and definitely not small startup owner. So I remember one time when I went on a startup competition, and I prepare ahead.

So I found four more two judges beforehand, I practiced mock interview pitch with them. So when I went on the competitions, my pitch was perfect. But right after the pitch, the judge asked me questions, la la la la la, and I was stunned.

I couldn’t answer any questions wasn’t because I didn’t know the answer. I did. I totally knew all of the answers.

But in my head, I didn’t believe that I could answer those questions. I was trying to find an answer. Yeah, this question practice judge number 37 asked me, and I answered it in appendix number two, I wrote down his answer, which was blah, blah, blah, let me think about what was the answer.

Of course, I lost the competition, which was $100,000 award. And because I didn’t believe in myself, I’m just a startup founder. What do I know?

That’s not true. I worked 15 years before and I think about this topic all day long, way more than anyone else for years. So after that, we lost the competition.

And it was a hot moment that I realized people don’t follow people with scripts, people follow leaders with opinion and trust themselves. So I switch your mindset and think again. And in the future, every time when I go on competitions, I try to make sure I’m present and really sincerely tell them my point of view, because I trust that people like to hear my point of view.

And that’s how we end up one another 11 award, including last year’s e-magazine Best Startup of the Year and the year before Business Journal Most Innovative Startup in Silicon Valley. So it’s all about mindset change and about the confidence.

I love how you mentioned self-trust, because having that self-trust in rooms where you may be underestimated at first, right? So what helped you gain more self-trust in those rooms?

Yeah, I think some techniques that someone told me before was that we tend to sometimes talk about that I should do ABC. So well, today I should exercise more, I should lose weight, I should start my new year resolutions, I should launch these new business departments and these new initiatives. We have a lot that we should.

And the more we say we should, the more negative that we feel about ourselves. Because yeah, you should, why are you not doing that? But it should be different because you can say, I would like to.

I would like to start this new year resolution. I would like to start learning this sport. I would like to start spending more time with my family.

I would like to. It’s become more positive. It’s more action-driven.

It’s that you are motivated to do so, not you are blind that you are not doing so. So I think this little tip really helped me to feel great. And I also think that the list of doing things wasn’t very helpful before.

When I have a long to-do list before, I would write down what I want to do and write down what I want to do. And the list becomes 1 and 3 and 10 and 11 and 100 and 200. And then you never look at the list.

Every time you open a list, you feel like the list was laughing at you. Like, why are you not finishing me? So you feel bad about yourself every day.

But what I do nowadays was in the morning, I just write down one or two things that I have to do for sure today. But everything else, just follow the flow. Time is limited.

You can never finish everything that you want to do. You are doing great as long as you are prioritizing your time for the stuff that matters to you. And everyone’s definition of matters is different.

Yes. And I love how you mentioned, even though after losing the competition, you didn’t give up. You signed up again and again for more competitions and eventually won all those awards.

But you know, you still win and sold after getting those awards. So what was the scariest decision that helped you get there?

I think the scariest decisions would be being a startup founder, right? But I would say, I won’t say scary decision, but I would say the mindset change is very important. For example, when I started being a founder, I feel like the world is not fair.

People only want to talk to IPO founder. People are, when they see your business card is CEO of Taelor. What is Taelor?

Oh, how do you spell it? T-A-E-L-O-R. What does it do?

Oh, we do it for AI stylists. We do menswear rental subscriptions. And I feel like nobody cares.

But at that time, at first time, I feel like that’s bad. Why the world, everybody goes to talk to this big boss in those lunch meetings. Why people only talk, mostly when being invited to events, people ask you, how much revenue your company has?

So at the beginning, I feel sad about that. I feel like life is not fair. Only people who have a lot of money and very successful in the fields will be recognized and respected.

But then I quickly changed my mindset. I realized that it’s blessing. Because when I was working for big tech companies, Meta or eBay as a head of product, people talk to you.

And you don’t know if it’s because they truly respect you, they like you as a person, respect your opinion, they think you are a person with good integrity, or simply they just want to do business with your company. You don’t know. But now being a startup founder, you start to realize, hey, people do value your opinion.

And that’s why they partner with you. Our customers like that our stylists pick stuff for them, help them to look great, so then they get a job, get a date, close a deal. You are delivering value.

That’s why they engage with you. So it becomes a lot more clear who are nice person, want to help you, who really value your contributions, who really like you as a person, as a friend, versus who just want to use your big title to do something. So my mindset changed from just feel bad for the world, and feel sad about that, feel like I’m nobody again, why do I make decision to be a founder, I should be working for big tech company, to something that I realized that is actually a blessing.

Before when I got my Amazon package, they’re supposed to, they’re supposed to show up today. Why is half day late? But now being a startup founder, I knew the Amazon package showed up because 20 people work behind.

Our merchants talking to hundreds of vendors, find a great product. A buyer decide on a pricing after lots of a spreadsheet. Our engineers build out the software to track the systems.

Someone packing in a warehouse for you, putting on the tab. The post office pick up from the packaging from the warehouse. And then there’s shipping, someone driver driving in a rent, and trying to go home for their dinner.

And eventually they deliver to you, and here with another tracking back to the system. Lots of things behind, lots of hard work behind. I start becoming more appreciative for the world, and seeing more for the world.

And I think that’s the mindset change from sad to be feel that life is unfair, to feel appreciating those learnings, those opportunities, those be able to see quality people who truly want to help you and value the friendship. And I think there’s a mindset change that made me have an energy and motivation to continue on the journey.

Beautifully said. I love how you explained your mindset shift, because we as founders need that mindset shift at every level of our business.

Yeah, I think so. It’s not, no matter at what level, I think it’s never easy. I remember after being a startup founder, one time I talked to a reporter.

And as people know, a reporter is still pretty high up, even though the world has changed into being influencer or whatsoever. But still, it was a major media company reporter. So the reporter, we met in an event, she sent me questions for some interview, the questions were pretty long.

So I was trying to write down the answers for her. And I forgot. So it took me about a week that didn’t get back to her.

So she went back and talked to one of our investors and say, hey, she feel like I probably just feel like she’s not an investor. So I don’t care. So don’t even care to get back to her, which wasn’t the intention at all.

So I think that imposter syndrome happen in every level. Like even I were 15 years in career, leading teams and working for big tech companies, even the reporter, spending 15 years live and becoming a major key person for a major media company, it still happens. It happened a lot.

It happened to women. And it happened at any stage of the career or life where it happened to people becoming a mom becoming a new, different roles in a life changing environments. So I would say that the tip is, it’s hard.

I still experience that every day. I’m no in positions in tell people what to do. I’m sure Lucy had better answer.

But I would say sometimes you start with a small voice in your head say, you cannot do it. You cannot do it. I think the tip is that you shut it down before you become too loud.

Because if you don’t shut it down, you will become, you cannot do it. You cannot do it. So you just shut it down when it’s small, still small.

And then I would say go out a startup founder or even being an employee for any company, you probably look at your company like, oh, this is wrong. And that’s wrong. And we have this whole bunch of things to do.

We have this customer complaint, we have these returns. But when you go out in conference or events, when you start talking to people, many times you will realize you thought you haven’t improved much. But just like your kids, you’re like, hey, they haven’t grown up, you turn around, oh my god, when do you are you as high as I am?

When do you start eating two bowls of rice, right? So you actually because the change is small, but change is frequent. So you actually don’t know how far you have already gone until then you go out there and talk to people.

So I would say heads up and start going out and talk to people you’re right, you realize there are a lot more people worse than you and you are actually doing really good.

Great reminder as a mentor and lecturer, you lecture on marketing, but what’s a pattern you see with maybe students you’ve had? What do they struggle with the most in marketing?

I will say I’ll answer the question differently. I will say, first of all, in general, what are the good students? Who are the good students?

I found that very interesting in my 10 years of teaching that the best students tend to be the that with little objective, which is very, very different from the education back when I grew up in Taiwan. It’s all about you have a clear goal and you achieve this goal. But somehow when I’m teaching at Northwestern University, turn out the best students in the class were those who have full with curiosity.

They learn, they take this course, not because the course has high score, not because that, oh, now AI is trendy, let me take the AI class. Oh, two years ago, five years ago, the analytics trendy, let me take analytic class. Yes, there could be a little bit, people all like popular stuff, but even more so, they are truly curious about this.

I think that’s very, very different from my mindset or the education I got because it’s all about, okay, Anya, you should know about what? What is the most important? Memorizing these things is important.

But then the more I grew up, I realized that the best students were those who actually care more about why. So from what to be how to be why. They were just curious about things because it makes sense because if you are only tracing trends, oh, this is popular, I should do this.

By the time that you know about this, it’s too late. The entire world is going to do so. Yes, you should be open-minded, learning new technology and new things, but you were just chasing the trend and you are always two steps behind.

10 years ago, I was doing personalizations and analytics and people at that time say like, yeah, that’s probably most of the fancy stuff will be working for like Time Warner, those type of amazing traditional company because they really own and then CPG, selling shampoo on P&G Unilever is the coolest company in marketing. And then what do you want to do marketing technology? What does it mean?

Nobody cares. You shouldn’t care about this. But fast forward, now you see those companies where even Netflix acquired a traditional company now.

So if you are just following the trend, then you are one step behind. So I would say, also believe in what you like. When I was studying marketing at Northwestern University, we had three tracks that people, students can select.

One is data and one is branding, which both are very cool. And there’s one called like media management, which no one knows what it is. For some reason, I don’t even know why, but I just really like the media management.

People say, no, no, no, no, no. You have to pick data because you are international student. Only data can get a job.

And people say, no, no, no, no, no. You should at least try branding if your math is bad, which is totally not true for people who do marketing analytics, not about math. But you should at least do branding because at least there’s a core of marketing.

But for some reason, I just like media management. I started my career in media company. I found it fascinating in media industry.

I just love it. So I decided to go with it. And when I graduated, Lehman Brothers went bankruptcy.

There was no job anywhere. But eventually in the entire class of like Chinese students or Asian or Taiwanese students, there are about 20 of us. And eventually there were two people stayed from the Taiwanese cohort.

And one is me who studied media management. And probably I will say I was definitely not top in the class, definitely in the bottom.

Yeah. But that would not have happened had you chosen the given way, right? The popular way.

I love that.

It is what I love. You are already whatever, 30, 40, 25 years old. So you are supposed to do what?

I feel like there’s never that true. And so that’s what I learned a lot in that. So back to the question on the marketing side, I think marketing is end of day.

It’s all about solving people’s problems. So it’s not just about beautiful slogans. And it’s about understanding people’s problem and then address that.

Oh, you have this problem. You feel like you are getting out of a concert and couldn’t find some things that easily to help you to go home. How about try Uber?

Uber can get you even with a large amount of people outside. You don’t have to wait in the rain and then trying to find the next taxi on the street. It’s about understanding the pinpoint and communicate with people with relevant information.

Okay, thank you for your expertise. You mentioned networking events, right? And obviously, your company would not be successful today without getting backed by VCs.

So how can women build powerful networks so they get they can get what they want, whether that’s funding or marketing, or what it is that is they needed to grow their business?

I think a lot is just give or skim and then find people who really have common interests where you feel good chemistries together. For example, we are backed by Bling Capital, which is the Madness List’s best VC in the US, which means their performance for the investors is high and top 10 in the US. But how did I get this investment was because another, I talked to another founder, and I was trying to ask him to introduce his investor to me.

But in a conversation, I forgot. I talked to him, he does like security camera. And I shared with him about how we use AI to pick cloth format, how we send people for people to rent.

And he really loved the idea for sustainability that helps people to look great while also helping the world reduce future inventory. So we’re just a great conversation. And after that, I forgot about the investor thing.

I connect a whole bunch of potential clients to him. I used to work for Meta and help bring internet or connectivity to countries that didn’t have internet. So I spent a lot of time in Africa, where we usually have bodyguards.

So I connect a whole bunch of bodyguard companies to him, and he got those leads. So a month after he reached out back to me, he said, thank you so much for those amazing clients. By the way, what were you reaching me out for?

How can I be helpful? Oh, yeah, yeah, yeah, I wanted you to help me to connect to your investor. So with half an hour conversation, we got a million dollar from Bling Capital, which is early investor between behind Lyft and Instacart.

So I would say give a scam and help build our connections with just genuinely with people who appreciate your business and help them out.

Yeah, so help each other collaborate and really putting yourself out there because you actually first of all, you had to introduce your idea, right? And that takes courage. I love that.

So for the women listening who has bold ideas, but is hesitating or has some type of fear before leaping to their next big endeavor. What is one last thing you want them to hear today?

I think you have to be something that you really like, because being a startup founder is not like a job you can work for a year or two or three. It’s usually three, four years or more time of a journey. So you have to like the idea.

So I personally, for example, when I was working for Meta, I want to look great, but I feel I because I feel impossible syndrome and then large technology team, I came from marketing and data scientist background. So I started looking for options like subscription boxes out there, but you all have to require me to buy. They style me, but I have to buy before I can wear.

So I start renting clothes using company like Newly, Render Runway or more, which some of them make a 500 million per year. But then I realized I have to browse through 10,000, 100,000 Garmin and spend hours. So it was a hard moment that I realized the world has been designing for people who love fashions versus for people who are not into fashion, but just want to look good to achieve their goals.

For me, it was just so then I can get rid of my impossible syndrome because I feel like I looks ready every day when no one knows I’m freaking out behind. So when I doing research and realize a lot of people actually think like me, but a lot them hate shopping and laundry and they are mostly guy, single guy and sales guy. And throughout the career in the last 10 years, I have always been passionate to help people achieve their goals.

I published books, I have online courses and I share on social media just because I think since I came from blue collar family, a lot of people help me. So I want to help more people to achieve a goal and it kind of tied to the business that I’m doing that people can look great and dress like who they want to be. At the same time, I have a co-founder, she came from a background, she really, really into sustainability.

She grew up wanting to be a fashion designer, but end up she became an accountant because she also grew up in the Asian family who say, you should have be a finance person. So she loves sustainability and renting clothes actually helping to reduce, to help on address the issue that today 30% of clothes goes to landfill generating 10% of carbon emissions. So I think both of us have that something that we truly believe and that’s why we decided to start a company.

So for people who want to have a next big idea, you just have to do something that you do like, not something they feel like, oh, this we just can make a lot of money or this is trendy right now because it’s going to be a long journey. If you don’t love it, you’re going to hate it because you are going to spend a lot of time 24 seven to think about it.

Beautifully said. Well, thank you for being with us. Anya’s info is linked below.

So feel free to connect with her and check out her website. If you know a man who needs to rent some clothes.

Yeah, feel free to email me too. I’m my email is Anya. Anya at Taelor.ai