Why Smart Leaders Let AI Pick Their Clothes (ft. Anya Cheng) | EP 106

Anya Cheng (00:00)
I spent time sleeping on different friends’ couches for months. One day, I really wanted to go to a conference because people told me you can meet a lot more people at a conference, which is much more effective. But conference tickets are very expensive. I decided to call a magazine company back in Taiwan. I said, “There’s an amazing conference in New York. Do you want someone to cover the story for free?” They said—

Paul Leon (00:03)
Hmm.

Paul Leon (00:03)
I have with me today Anya Cheng. She is the founder and CEO of Taelor, an AI-powered men’s clothing subscription service promoting sustainable fashion. A Silicon Valley entrepreneur, she has been recognized among Girls in Tech 40 Under 40 for her expertise in tech, product management, and marketing.

Anya played a pivotal role in launching Facebook and Instagram Shopping at Meta, led new business expansion at eBay, and helped grow McDonald’s global food delivery. She has also shaped Target’s mobile commerce and has led teams in AI, e-commerce, product management, and marketing across Fortune 500 companies.

Anya’s award-winning venture, Taelor AI, was named one of the Bay Area’s most innovative startups to watch by the Business Journal. It is backed by early investors in NVIDIA, TikTok, Facebook, Lyft, and Spotify. Anya’s work has earned her 30-plus prestigious tech and marketing awards. She is a bestselling author and a two-time TEDx speaker. She teaches at Northwestern University and is a popular keynote speaker worldwide.

She holds a master’s in Integrated Marketing Communications from Northwestern University and an MBA from the University of Chicago Booth School of Business.

There are three exclusive gifts in this episode of The Manager’s Mic that she has graciously offered.

Gift number one: Get 25% off your first month of men’s clothing subscription by using the code PODCAST25. You can sign up at taelor.style.

Gift two: This is actually really cool. You get 50% off your first month of women’s clothing subscription using the code ARMOIREXTAELOR, spelled A-R-M-O-I-R-E-X-T-A-E-L-O-R.

Gift three: You can get 10% off gift cards using the code PODCASTGIFTS.

If you want to leverage these gifts to give yourself the most important gift back—which is your time, convenience, and effortless style—I encourage you to visit those websites.

Anya, it is a real honor for me to welcome you to The Manager’s Mic. I’m really looking forward to our conversation today.

Anya Cheng (02:44)
Thanks, Paul. That was an amazing introduction. I feel like I’m ready to go home like, “Hey, you guys got a gift. Bye.”

Paul Leon (02:49)
(laughs)

Anya Cheng (02:52)
We’re an AI startup, but we serve customers nationwide. We use AI to pick clothes for busy men. Imagine in the old days, only celebrities had human stylists. Now, with AI, everyone can have a “human stylist” at their fingertips. AI will pick clothes for you, and we send you real clothes to wear for a couple of weeks. Once you’re done, return the dirty clothes and get the new ones. No more shopping or laundry.

I’m excited to share more about my experience as a manager over the last 15 years in big tech companies, startups, and across industries—technology, retail, and more traditional companies.

Paul Leon (03:32)
Thank you for being very transparent. I’ve done a lot of research and watched your TEDx speeches. They’re very impressive.

When I start a podcast, I like to reverse engineer someone’s story a little, if that’s fair. I’m so impressed with your website. I feel like I haven’t had somebody of your level of success in the clothing space, because I think it’s a tough business to thrive in—and you’ve been very successful at it.

What were the moment or moments where you said, “You know, Anya”—maybe you’re talking to yourself from a high-level view—“I really want to take the challenge away from decision fatigue in fashion and looking good.” What key things happened that made you say, “This is a journey I want to go on”?

Anya Cheng (04:18)
In fact, it’s highly relevant to my journey as a manager.

As you can probably tell from listening, I’m a woman of color. I’m an immigrant from Taiwan. Throughout my career in tech, as someone with a marketing background, I always felt imposter syndrome.

Am I ready to be a manager? Will people listen to me? I’m leading a 65-person team. I’m leading a $42 million budget in addition to salaries. Am I really ready? Will people find me fake? I felt imposter syndrome throughout my journey.

There was a moment when I was at Meta and eBay where I felt like I wanted to look good so people wouldn’t find out that I was freaking out every day. So I used some subscription boxes, like Stitch Fix and others. Traditionally there were companies like [as spoken], but those required you to buy.

They style you, you get the clothes, but the moment you receive them you have to decide: Am I going to wear these many times? Can I find them cheaper somewhere else? How do I pair this? How do I do the laundry? Does it require dry cleaning? How do I iron it afterwards? Folding the clothes—managing all that.

I realized I don’t want to own that much stuff, because once you own something, you have to decide to buy it—and then you have to do the laundry and folding. So I started renting. I used companies like Nuuly and Rent the Runway—women’s rental companies. They’re amazing because you don’t have to buy. You rent the clothes.

It’s like Uber: you get in the car, you get out of the car—you don’t own the car, but you always have a car ready. It’s like Netflix: you turn on the TV, you watch a show for five minutes. If you don’t like it, who cares—move on. Same thing for rental. You get clothes, you wear them for a few weeks. If you like it, great. If you don’t, return it.

I love it, but I also hate it because there are like 10,000 garments—swap, swap, swap. Browse, browse, browse. Pick, pick, pick. I hate it.

Paul Leon (06:09)
Yeah.

Anya Cheng (06:21)
I’m not someone who’s into fashion. I’m just a manager. I want to look presentable and ready to lead my team.

Then it hit me: there are no options out there actually built for managers. We just want to be ready for the day. I don’t want to read GQ every day. That’s why Taelor was born.

Paul Leon (06:25)
Yeah.

Anya Cheng (06:45)
I started doing research: Who thinks like me? Hates shopping, hates laundry, needs to look good, but is not into fashion.

Turns out most of them are men—busy men: managers, salespeople, executive recruiters, professors, accountants, consultants. You’re busy every day. You want to look presentable.

And you’re worried. You worry if people feel like you are too “control freak.” You worry people feel like you are too loose. You worry that if people perform better than you, you’ll get replaced. You worry that if people don’t perform, you’ll get replaced.

I realized I wanted to help people who are busy but want to look great so they can focus on what they do best—which is leadership. That’s why Taelor was born.

We use AI to style customers. We send people real clothes.

Paul Leon (07:31)
Yeah.

Anya Cheng (07:38)
They wear them. If they want to buy, great. If not, they wear them for a couple of weeks. They return the clothes with a prepaid envelope, drop it at any post office, or open the USPS app—one click, they pick up for free. Then in a few days you get the new shipment again. No more shopping or laundry.

Paul Leon (07:57)
It’s really impressive that you found this niche. When I look at your business from an 80,000-foot view and come down from that, I think about all the layers you had to figure out—and the mental toughness. Mental toughness is a key word here.

Watching your TEDx speeches, you’re very humble and very inviting to talk to.

When you were struggling with imposter syndrome—since you mentioned it—was there any quote, framework, or something you kept on loop? Maybe you’re walking on that treadmill, in that same place, and you keep referencing something to say, “This is how I get imposter syndrome under control.” If you’re comfortable, can we peel that onion?

Anya Cheng (08:43)
I think the first thing is: before the voice in your head says, “You’re not worth it. You’re not good enough,” it usually starts with a really small voice: “You’re not good. You’re not good.”

If you don’t shut it down, it gets louder. The trick is to shut it down before it becomes too loud.

I also think, throughout my career, there are things that are really important for me as a manager. Manager means two things: manage down, and manage up.

Let’s start with manage up. Early in my career, I wanted to be at the executive table. I wanted people to trust me and value my team. But I started as a marketer. People saw me as “the marketing girl.”

They’d say, “We don’t need marketing until everything is figured out, and we just need more people to shop. Hey, marketing girl—now it’s your turn.” No. I wanted to be on the executive table. Call me before it’s last minute.

So I went into meetings and promoted “marketing, marketing, marketing.” That was useless. Because when you act like a department head only, you never get a seat at the executive table.

People don’t call “the marketing person” to the executive table. They also don’t call “the engineering person” to the executive table. People don’t call anyone to the executive table except problem solvers.

Because big problems are not well defined. When something becomes an engineering problem, or a marketing problem, or a finance problem, it’s usually a smaller problem.

Big problems start as something like, “We don’t have enough customers.” That’s not just marketing. It could be pricing. It could be customer service. It could be product, which needs engineering.

It starts as a problem no one knows how to solve—and executives come in to solve it.

I realized the way to be a great manager is to forget who you are. Forget that you’re a marketer. Forget you’re finance. Forget you’re engineering. Forget you’re supply chain.

Go into the meeting trying to figure out: What is the problem for the company? What is the problem for customers, clients? And solve the problem.

Don’t worry—because you’re still an expert in your own field. So the solutions you come up with will tend to be relevant to your team anyway.

“We don’t have enough customers.” No worries—maybe we do promotions. Maybe we attract the wrong customers. We should do research. Because you’re an expert, you’ll naturally bring solutions that support your team.

People don’t call you because of your department. They call you because they want a problem solver.

That’s managing up.

Now managing down: as people leaders, when I was younger, I wanted to be buddy-buddy with the team. I thought if I was close to them, they’d like me—and I was afraid they wouldn’t like me.

But whether people like you is less important. People want to make impact. People want to work for a company that’s successful.

It’s extremely difficult to lead a failing team. If the company is making money, everybody’s happy with their manager. If the company is losing money and laying people off, everybody hates their manager—no matter how close you are.

At the end of the day, your team has to win. Nothing else matters.

They can like you as a person, but if you’re on a losing team, people will leave. Look at LeBron: if he stays on a losing team, eventually he jumps to a championship team. You can’t retain people just by being liked if they feel like they’re on a failing ship.

Your job is to solve the problem—and to use your team to solve the problem.

But you’re not leading an all-star team. The NBA All-Star Game can be boring—everyone is an all-star, but they don’t play like a team. A championship team is worth watching. Not everyone is an all-star, but they play as a team.

As a leader, your job is building the puzzle: someone good with numbers, someone creative, someone risk-taking, someone research-focused to ground the numbers, someone upbeat to rally people, someone calm and cool.

So the team isn’t running around like chickens with their heads cut off. Your job is to figure out: What problem are we solving? What skills do we need? How do we assemble the team so they help each other—and your team can win?

Those are the two most important things as a manager.

Paul Leon (14:34)
That’s impressive. There’s a lot of wisdom in what you said—that they bring problem solvers to the table.

I know you’re speaking from true validity, because on the surface, one thing I’ll admit: I struggle with wanting people to like me. That’s something I personally struggle with.

You’ve been very successful at Meta, eBay, McDonald’s, and Target. These are not easy companies to earn rapport and build trust in, and to achieve results.

If you were to wave a magic wand, is there anything—maybe “mistake” is not the right word—but if you could eliminate certain things so someone can be a better problem solver, what would they be?

Anya Cheng (15:20)
There are a few mistakes people tend to make.

Number one: as a new hire, people come in and “poo-poo” people. “Your website sucks.” “This and that need improvement.” During interviews, that can sound great.

But once you’re onboard, the people you said “suck” are your colleagues. You’ve already pissed off a bunch of people. Who’s going to help you?

And usually those things “suck” for reasons: legacy technology, tiny budgets, user research is on leave, and so on. Those become your problems.

To solve problems, you need the team. Then you turn around and say, “Engineers, researchers, designers—help me.” Nobody helps you, because you just called their work “sucks” a week ago.

So number one: don’t create enemies at the start. Don’t put down people’s work. Appreciate what has been done, and build from there.

Another thing: change management has to start small.

At McDonald’s, they hired someone very cutting-edge. At that time, McDonald’s didn’t even have Google Analytics. This leader talked about flying drones to deliver food and self-driving cars.

But after three years, the person left. Big ideas were never realized, because change has to start small.

Change management is about small change daily. You barely notice it. Big change is hard for many people to accept.

It’s also important to know everyone is motivated differently.

Some people want to be product managers one day, but right now they’re data scientists. Give them work that builds product skills.

Some people value family time. They appreciate working from home sometimes to take care of pets and kids.

Some people are young and want to travel, meet people, and have experiences. Others have kids and hate traveling.

Figure out preferences. Figure out communication styles.

Some people want to be informed right away. Some want things in writing. Some don’t want to decide immediately.

For example, my co-founder and I think very differently. When we have problems, I do research by asking people. Her way is Googling and reading articles. At first, we clashed: she felt I wasted time talking to people; I felt she sent random articles.

Over time, we learned: she researches her way; I research my way. I interview people and write a summary—since she likes to read, she reads my summary. Then she reads articles and gives me her summary. We compare notes.

Instead of finding this out over time, just ask.

Ask people: “What’s your preference?” “What’s one thing you hate?” Some will say, “Don’t walk up to my desk—book time.” Others will say, “Come talk to me right away—don’t waste my calendar.”

Just ask. Most people want to work well with you. Ask from day one: “How do you work? What’s your style? What do people say about your style?” Ask your boss, your team, your colleagues.

Paul Leon (19:53)
I like that. I also like the change management insight. I just wrapped up a change management class in my MBA program. I still feel like a lot of what’s taught is a bit outdated, and your perspective feels fresh.

You mentioned your coworker and how you both manage styles—feedback, research, and different approaches.

Because of the size of teams you’ve dealt with, I’ve seen people with big personalities who really want to win, or two people who both want something. I’m going to make an assumption and you can push back.

If a manager has two people with big personalities and it’s hard to navigate, how should they handle it—especially during heavy, intense change?

Anya Cheng (21:43)
Don’t focus on it. The more you think, “This person has a big style,” the more you worry about it.

Come back to the goals. “Our goal is to get more customers this month. We want more people to sign up.”

Right now, our website sucks—conversion isn’t there. So focus on the goal: How do we achieve it?

You have your way. I have my way. As long as we divide and conquer, do what you’re good at, do what I’m good at, and achieve the goal, we’re good.

Changing other people is hard. Trusting people is hard. Making people trust you is hard.

Start by changing yourself. Start by trusting people first.

There’s a joke—just a joke, but it’s worth thinking about. A thief went house to house. One house didn’t lock the door. The thief left a note: “Thank you for trusting me, so I didn’t steal anything.”

When you smile at people, they smile back. When you get angry, people get angry back.

Start by trusting people. If you can change yourself, do it. If not, it’s okay—you still have a common goal.

Differences are good. A team without diversity usually sucks. The team is happy, but it sucks. If decisions are easy—everyone agrees—it often sucks, because you’re not thinking like your customer. Customers are diverse.

If you don’t have debate, you’ll create something bad.

When you have a diverse team, different points of view are good. Debate is good because it means people care. If people don’t care, there’s no debate—“do whatever you want.”

So appreciate debate. It means passion. It means the result will be better.

Focus on the goal, less on the person. You’re on the same boat.

Also: speak to the elephant in the room early.

You’ve probably been in meetings where someone disagrees, but they’re polite, and they wait until the end to say, “I disagree.” The entire time, they weren’t listening—they were waiting.

So from the start, open it up. Otherwise, they’ll be waiting and not listening.

For example, at Taelor, we are an AI company that picks clothes and rents clothes.

Sharing is everywhere: Uber, Netflix, Airbnb. You sleep on hotel beds that many people slept in. In restaurants, the spoon and fork have been used by many people. Secondhand is everywhere.

But investors might say, “I have custom suits. I would never wear secondhand clothes.”

So instead of waiting until the end, I open with: “You’re probably curious—why would anyone wear secondhand clothes? But it’s trendy. Gen Z loves access versus ownership.”

People don’t want to own as much. Ownership means laundry, ironing, folding, and less variety. Renting means freedom and convenience.

By addressing it upfront, the person listens, because they feel heard from the start.

Paul Leon (26:29)
I love that. One thing I want to call out—this wasn’t in my notes—but I enjoyed your website because you put out a lot of good information on your blog about fashion tips. Your solution takes the pain away from deciding what’s fashionable and professional, but you also have practical guides. I was reading your blog about what to wear at a comedy show, and I found that interesting because I had to pause comedy after doing it for five years while finishing my MBA.

I think it’s innovative to combine AI with clothing. I’m not asking you to share your IP.

If someone wants to incorporate AI more into their workflows or management, what upfront things should they expect? If you could go back and start again, what would you do differently when incorporating AI into a workflow or business?

Anya Cheng (27:38)
Number one: we all know AI is good for productivity. Anything repetitive, AI can probably do.

But it’s important to figure out: What value do you bring to your customer?

At Taelor, people think we’re a clothing company. We’re not.

For fashion brands, we’re a data company. We help brands get customer feedback and reduce waste. Today, about 30% of clothes go from factory to landfill, generating about 10% of carbon emissions and about 20% of water pollution. We collect insights and return data to brands and retailers to help predict what will sell.

For consumers, people think we’re a clothing company. We’re not.

We’re more like an executive assistant—a service company powered by AI.

Customers use our service because they don’t want to spend mind space on fashion. They want to look good so they can get a job, get a date, close a deal.

If someone comes to us and says, “I’m going to a conference,” we might send an interesting print as a conversation starter. Someone says, “Nice shirt—dolphins.” Then the customer explains the rental model and AI styling. It becomes a conversation starter.

For dates, we send a jacket when it’s cold. You put it on someone’s shoulders. You get a second date. It’s about achieving the goal.

So: on one hand, use AI to remove bottlenecks—what’s stopping growth, retention, and customer acquisition?

On the other hand, understand your value proposition.

Target is inspiration—people walk in for one thing and buy 20. Walmart is value pricing. Amazon is convenience and service.

Understand your value prop. Use AI to remove your bottleneck and reduce repetitive work.

Paul Leon (30:57)
That’s impressive.

I watched your TED talk and I’d encourage people to watch it. It’s titled “How to Keep Going When You Want to Give Up.”

I’m attracted to people who are humble. I still try my best to look good for my wife. I take her out on date nights, put a coat on her shoulders. I’ve had more than a second date, so I think I’m doing something right.

What I like about professionals like you is your humility, and when we peel back layers, it’s cool to meet someone who went through a lot of resistance.

My question is: when it comes to resistance—a word we have to get comfortable with—what do professionals need to accept about resistance when pursuing the business outcomes they want?

Anya Cheng (32:13)
That TED talk was about using your strengths.

When I graduated from Northwestern University, it was 2008—right after Lehman Brothers went bankrupt. There were no jobs. My only job before was being a reporter back in Taiwan. I had a master’s degree in marketing, and I was looking for marketing jobs. As someone who barely spoke English, it was really hard.

I waited outside buildings for other departments because I couldn’t even get campus recruiting for my own department. As soon as a recruiter came out, I gave him my résumé.

People said, “You’re crazy. That’s too aggressive.” But it wasn’t hard for me, because my only job before was being a reporter. Waiting outside and giving people my camera and microphone—that was normal.

When I was using my strengths, I could try again and again.

I went to New York because someone told me Chicago was small and New York and LA had more jobs. I went to New York and slept on friends’ couches for months.

Then I wanted to go to a conference, but tickets were expensive. So I called a magazine in Taiwan and said, “There’s an amazing conference in New York. Do you want someone to cover the story for free?” They said yes.

Then I called the conference and said, “Hi, I’m a reporter from Taiwan. Can you give me a press ticket?” And I got in for free.

People think that’s crazy. But for someone who was a reporter, covering a conference was easy. I didn’t know what else to do, but I knew how to use my strengths.

When you use your strengths, you’re not as afraid. You try again and again because you feel, “I can do that.”

I continued looking for opportunities. I thought I should do marketing for media companies, because I had been a reporter. That was a bad idea—I didn’t realize media companies don’t need marketing the way I imagined.

I bought newspapers from newsstands and called publishers. In the old days, newspapers listed publisher names and phone numbers. I called and asked for informational interviews.

Again, people think that’s crazy. But as a former reporter, I knew how to call people and ask for interviews.

Looking back, it wasn’t that I was resilient. It was that I was using my strengths.

Your strengths are different from mine. Maybe you’re a people person. Maybe you’re a numbers person. Maybe you’re full of curiosity. Maybe you came from big companies with strong SOPs, or startups where you wear multiple hats.

Your background, resources, and network are different. There’s no good or bad.

The best way not to give up is to use your strengths. Then you don’t feel out of options. Trying again and again gets you to the light at the end of the tunnel.

Paul Leon (36:17)
That story is powerful. I was in Toastmasters for 10 years. I was a president. I worked with engineers who couldn’t articulate a story like that.

One of the best pieces of advice I heard is: what comes from the heart goes to the heart, especially in storytelling.

You’ve talked about imposter syndrome, leveraging strengths, and that story. Would you say your advice to early-career employees is: even though it’s tough now, lean into your strengths?

Anya Cheng (37:23)
I really like what you just did. Let me repeat what I heard from you—and you tell me if I’m right.

This is a very powerful technique: repeating what you heard. People repeat themselves when they think you’re not getting it or not listening. As a manager, it’s powerful to repeat back, because the other person realizes you got it—or they realize they weren’t clear.

It’s a very powerful technique.

As an early manager, it’s important to do what your manager is doing. Your job is to replace your manager so your manager can be promoted.

If your manager can’t be promoted, and you’re not promoted, it’s often because people don’t think you’re qualified yet. You have to be doing their job.

For example: I had an amazing employee who managed paid search. One day he said, “Anya, paid search has become a bottleneck. It hasn’t performed the last few months. That’s my job and my fault. I think it’s time for you to fire me as the paid search manager. I found a contractor who can take it to the next level.”

Are you going to fire that person? No. You love them even more, because they’re doing your job. They’re thinking like you: “I’ve hit my ceiling. We need a new level.”

Then he said, “Our website conversion rate isn’t high. I have growth and product experience. I can use the time freed up to improve conversion rate.” Amazing—he created his next job by thinking like a manager.

Another example: a team member goes to a meeting, comes back, and says, “I heard the big boss wants to do a new strategy. Whoever focuses on it gets budget from the central team.”

That’s information I should know. Sometimes peers won’t share it because they’re afraid of losing budget. But because my employee is networking and thinking like me, they bring it back. That’s doing my job.

Also: when you do a presentation to your boss, the reader isn’t actually your boss. They may not care, even if they say it’s great.

Your real audience is your boss’s boss.

After the presentation, two scenarios happen:

One: it’s amazing, and your boss takes it to their boss and says, “We should do this.” That’s impact.

Two: it’s bad, and your boss gives feedback so you can improve. That’s still useful.

But if they say “great” and put it in a drawer, you wasted their time. Nothing improves. The company doesn’t improve. You don’t improve.

So remember: whatever you prepare is not just for your boss. It’s for what they need as the next step. Think on behalf of your manager, and act like your manager—then you will become your manager.

Paul Leon (42:50)
When I talk to you, I feel like I should know these things, but hearing it this way is refreshing and empowering.

I have two questions, with your permission. One is impromptu.

Earlier you said it’s important to ask for feedback, so I’m going to apply your advice. This is intimidating for me to ask.

Anya Cheng (43:03)
(laughs)

Paul Leon (43:14)
What do you think of this cowboy hat from a style perspective, since you’re the expert? I’m nervous to ask, but if I don’t apply your advice, what’s the point?

Anya Cheng (43:26)
It looks great. Anything that makes you feel confident and like yourself is great.

The point of looking good is to feel like yourself—the best version of yourself.

A simple tip: look in the mirror before you go out. Believe it or not, most people don’t. They rush out the door. If you look in the mirror, you’ll realize you’re doing great.

Another simple tip: your belt color should match your shoes. And if you look head to toe—including backpack and accessories—no more than three colors. Dark blue and light blue count as one color.

If you like trendy: shorts are getting shorter, skinny jeans are out, baggy is in.

The color of the year is maroon and also light brown—mocha colors.

But the most important thing is you feel like yourself.

Paul Leon (44:18)
Really?

Thank you. You’re too kind. Now my ego is inflated a little. I’ve got to stay humble.

My last question: it’s a time-travel question. You can go back 10 years. I don’t know your age—you look very young.

You can talk to Anya, and you can only tell her three things. But the catch is: you cannot tell your younger self it’s you. You can pick any moment in time.

What three things would you tell that Anya to accelerate her career growth even further?

Anya Cheng (45:22)
Number one: get involved with things you don’t think are useful yet.

I’m Asian, from Taiwan. In our culture, we educate “what,” not “why” or “how.” “Study engineering because it makes money.” “Be an accountant because it makes money.” “Learn AI because it’s the future.”

We like practical things with immediate results. But life is never what you expect. Learning things that aren’t useful yet is actually very useful.

I teach at Northwestern University. My best students are full of curiosity. Because the moment you realize something is useful, it’s too late.

“I should be a data scientist.” Everyone already says that. “I should invest in AI.” Everyone is already investing in AI.

If you realize it’s useful too late, you’re not an expert yet. Then it takes five more years to become an expert—and by then, you’re behind. If you chase trends, you’re always late.

As a startup founder now, I regret that when I worked at a big company, I didn’t get more involved in startups. I should have been an investor. Many investments start at $10,000 or $25,000. Many startups take small checks. As an investor, I could have seen many startups and learned how they work.

But I didn’t, because I thought it wasn’t useful. “Why do I care about startups if I work at Meta, eBay, Target?” And then I became a startup founder. I wish I knew more people in that space earlier.

Also, early in my career, as a marketer, I never thought I’d lead engineering teams. I thought that was for people with engineering backgrounds. But I became a product manager, then head of product, and I led engineering and technology teams.

I started attending coding classes later. I wish I did it earlier.

You can’t predict what’s next. Be curious. Follow your heart to learn. Make new friends. Break your comfort zone. Meet people outside your current circle. Learn something different.

Eventually, all of those become resources for your future.

Paul Leon (48:12)
I love that. I feel like I’ve grown from our conversation. It’s been empowering. I’m looking forward to publishing this episode, and I’m going to do my best to make it as attractive and fashionable as I can. I know I’m not going to meet your standards, but I’m going to give it my all.

Anya Cheng (48:37)
Thank you so much. If anyone wants to keep in touch, reach out to us. I’m at anya@taelor.ai—A-N-Y-A at taelor.ai, T-A-E-L-O-R.ai.

If you are an investor, supplier, fashion brand, or want to partner with us as a marketing partner, we partner with executive coaching companies, dating sites, and fitness centers.

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