How to Get Your Business Recommended by ChatGPT, Claude and Other AI Search Tools
7/8/202630 min
Your customers stopped Googling. They ask ChatGPT now.
And when ChatGPT answers, it recommends someone. If that someone is not you, this episode explains exactly why, and exactly what to do about it. One founder already cracked it: 10 million impressions from ChatGPT, zero dollars in ad spend, and an American Marketing Association campaign of the year award to prove it was not luck.
Anya Cheng spent her career building products and marketing at Meta, eBay, Target, and McDonald's tech headquarters before founding Taelor, an AI-powered menswear rental company in Silicon Valley. She is a Northwestern lecturer, TEDx speaker, bestselling author, and mentor at 500 Startups. In this conversation, she opens the playbook most agencies are still guessing at.
The episode starts with the business itself: an AI stylist backed by human experts that dresses busy operators for the outcome they need. A deal to close. A courtroom to win. A first date that earns a second one. Then Kayvon does what he does on every episode and reverse engineers the real gold. The conversation turns to how Taelor actually acquires customers, and the answer is not ads. It is AI search. Anya breaks down why sentiment now outranks keywords, why Reddit threads and review platforms feed the machines, why AI can analyze your video and podcast content beyond the keywords Google Search relied on, and how a human-AI content flywheel turns proprietary data into a moat no competitor can copy.
This one is for founders, operators, and marketing leaders who feel the ground shifting under their acquisition strategy. If your growth plan still assumes people find you through a search bar, you are optimizing for a behavior that is disappearing.
The conversation covers answer engine optimization, AI SEO, generative engine optimization (GEO), and the practical mechanics of getting cited by the likes of ChatGPT, Claude and Gemini. It digs into proprietary data as a competitive advantage, building content flywheels that combine human expertise with AI scale, customer acquisition without paid ads, subscription business models, and what it takes to become an AI-native company instead of a company that merely uses AI.
Topics covered:
- How Taelor's AI plus human stylist model works
- Why fashion companies were built for the wrong customer
- The shift from Google search to AI recommendations
- Sentiment, reviews, and context: the new ranking signals
- The exact content system behind 10 million ChatGPT impressions
- Why proprietary data is the only real moat in the AI era
- The 40 percent problem: fashion's unsold inventory crisis
- Dressing for outcomes: deals, courtrooms, and second dates
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Transcript preview
First 90 secondsSpeaker 10:00
10 million impressions from ChatGPT, $0 in ad spend. That's not a typo. That's what today's guest pulled off, and it won her campaign of the year from the American Marketing Association. Anya Cheng spent her career leading product at Meta and eBay, then she walked away and built Tailor, an AI styling company that dresses busy men so they can get the job, get the date, and close the deal. But here's why this episode matters to you. Anya cracked the new search game. People aren't googling anymore, they're asking AI, and she figured out how to make her company the answer. If you're building a brand, selling anything, or wondering why your traffic is drying up, this is the playbook. Let's unlock it. [upbeat music] Anya, welcome to the show. I, I'm excited to have you. I, I think what you're doing is amazing. So just for l- for the listeners here, today is a little different episode here. Today, today is not about what you're doing in your business or how you're doing it in your marketing, today is how you show up. How are you looking when you're going into the meetings? How are you dressing? Anya has created what I think is a, a phenomenal opportunity for people to be able to get onto a subscription and wear high designer fashion at half the fraction of the cost.