She Started a Company With a $10 Shopify Site. Then Ignored Her First Customer for a Month Because She Thought He Was a Scammer.

Anya Cheng grew up in Taiwan. Her dad worked in a factory. Her mom was a housewife. Nobody in the family had started a company, and she didn't even know what entrepreneurship was until a couple of years before she became one.

She now runs Tailor AI — a subscription service that uses AI to pick and rent clothes for busy men — has raised $2.3 million, and counts the YouTube founder as an angel investor. She was also, at one point, convinced her first U.S. employer wanted her to do plumbing.

This was recorded on the Startups with Stu show, and it's one of those conversations you find yourself rewinding.

The Principal's Office and the 200-Page Handbook

Before any of that, there was a high school in Taiwan that didn't allow new clubs. You got assigned to one of ten existing ones. That was the rule.

Anya wanted to start a media club. The school said no. So she went home, read the entire student handbook — hundreds of pages — and found a buried clause: you can start a new club if you collect a petition from a few hundred students. She went class by class. Got over 500 signatures. Her mom got called into the principal's office. Anya nearly got expelled. The club launched anyway.

She was eighteen. She didn't call it entrepreneurship at the time. But that's exactly what it was — find the real rule, not the assumed one, and work within it.

Couch-Surfing New York With 20 Alumni Letters

She graduated Northwestern with a marketing master's in 2008. Lehman Brothers had just collapsed. No jobs anywhere.

She showed up at other schools' career fairs — engineering, law, history — and handed her resume to recruiters as they walked out. People said that's not how networking works. She didn't know anyone, so she didn't have options.

Eventually a laid-off recruiter suggested she try New York. So she went. She couldn't afford to move there, so she stayed with friends week by week, called twenty Northwestern alumni she'd printed off the school website, met with executives at the New York Times and major media companies. Nobody was hiring.

Conference tickets were $2,000. She didn't have $2,000. So she called a Taiwanese media company, offered to cover the conference on their behalf for free, got press credentials, and walked in as a media representative.

She was doing all of this barely speaking English, with no contacts, no money, in the middle of the worst job market in a generation. She never framed it as hustle. She just kept moving.

The Plumber Misunderstanding and the First Real Job

She came back to Chicago ready to go home to Taiwan. But before she left, she called the trade magazine that had given her the press pass. Farmers and salon owners — niche as it gets. She told the CEO she'd just spent two months interviewing their competitors, advertisers, and readers. She'd put together a business plan with three specific recommendations. And she happened to know someone who had the marketing and media background to execute them.

They offered her a contract. She went home and Googled the word. She genuinely thought they wanted a plumber.

She built a digital marketing services department inside that farmers magazine. Her third entrepreneurial move, she said. The first was the high school club. The second was creating her own job.

Fifteen years followed — Meta (launching Facebook and Instagram Shopping), eBay (new markets across Latin America, Africa, Asia), McDonald's (food delivery, in-store kiosks), Target (Silicon Valley tech office). Always 0-to-1. Always building things that didn't exist yet.

The $10 Website and the Customer She Ignored

She left because of imposter syndrome. As a Taiwanese woman leading engineering teams without a technical degree, she wanted to look the part. Not for vanity — she described it as putting on a suit before an exam. You're not necessarily more ready. But you feel ready, and sometimes that's enough.

So she and co-founder Phoebe tested one hypothesis: will men rent clothes?

They spent $10 on a Shopify site. No inventory. Just a box that said: if you're interested, leave your email. A month later, a guy named Michael emailed saying he was eager to get started. Anya ignored him. Scammer, she figured. Who actually wants this?

He called a month after that. Real estate agent from San Diego. He'd found her number through AirDrop at a conference. He'd been on the waitlist for two months and assumed they were too popular to get to him yet.

They weren't popular. They just weren't ready.

She went to a department store sale, packed clothes into a shipping box, and mailed them to Michael. Then they did the same for a hundred people, interviewing every single one. The customer turned out to be busy, socially active men — consultants, sales guys — who needed to look good and wanted someone else to handle it entirely.

$2.3M, a School Rivalry, and 150 Brand Partners

For funding, they posted in WhatsApp groups for Northwestern and Chicago Booth alumni, hosted info sessions, and raised $1 million from their communities before speaking to a single VC. For the institutional money, a professor connected them to a founder. Anya spent the whole call genuinely trying to help him — he needed security company contacts, she had them from her Meta days in Africa. She forgot to ask for what she came for.

He circled back weeks later after landing a client through her intros. Asked how he could help. She remembered. He referred her to Bowling Capital, the top-ranked AI VC in the U.S. Half an hour later: $1 million committed.

For brand partners, she needed press. She'd won a startup competition co-hosted by Northwestern and the University of Chicago. She pitched it to the Northwestern school paper — not as a win, but as a rivalry story. A Northwestern faculty member winning a competition held at U of C? The paper ran it. An ABC affiliate called the next morning. She went on the morning show, took the clip, and sent it to the fashion trade publication that had already rejected her twice — as evidence they could use to convince their editor. The story ran. The first brand partner reached out within hours. Today Tailor AI has 150+ fashion brand partners.

What Stuck With Me

Only 1.8% of VC funding goes to female founders. Anya watched a three-time founder wear a fake wedding ring at TechCrunch's Startup Battlefield because research showed married women are perceived as more trustworthy. That image didn't make Anya angry. It made her strategic.

She redefined minority broadly — Italian Americans, Nigerian Americans, LGBTQ investors, people from finance backgrounds, anyone outside the default Silicon Valley majority — and rallied them. Her cap table now includes Google Gradient Capital, the YouTube founder, and Morgan Stanley's managing director.

She didn't fight the system. She found the people the system had also underestimated and asked them to bet on each other.

There's a pattern to Anya's story: she never assumes the rule is what people say it is. She reads the handbook. She finds the clause. She works within it until the door opens.

She wants to sell Tailor AI, get a PhD in behavioral science, and turn her research into the next company.

Of course she does.