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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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🎧 Highlights:
[00:00:00] From freelance writer to $10M ARR founder
[00:03:36] How Pepper scaled from a marketplace to an AI-powered content engine
[00:05:06] The hybrid model: humans and AI creating together
[00:07:12] Building “Nimbus” — Pepper’s internal AI platform
[00:08:24] Re-optimizing thousands of old pages automatically
[00:13:03] Why FAQs and freshness signals help you rank in AI results
[00:15:00] GEO: Generative Engine Optimization explained
[00:16:12] Tracking brand mentions across ChatGPT, Claude, Gemini, and Perplexity
[00:18:00] Using AI to generate videos, voices, and creative assets
[00:25:12] Scaling creative testing with 30,000+ AI-made ad banners
[00:27:18] How smaller creators can apply these lessons today
[00:30:27] Reddit, LinkedIn, and UGC as new AI search signals
[00:33:00] Cold-emailing OpenAI’s Greg Brockman and getting access to GPT-3
[00:34:21] Building PepperType.ai and learning from early AI adoption
[00:35:30] Using AI personally to optimize meetings and calendar time
In this episode, Andrew Warner interviews Anirudh Singla, founder and CEO of Pepper, a company that uses AI and human expertise to produce hundreds of thousands of pieces of content for enterprise brands.
Anirudh shares how he went from writing on Upwork to building a platform now doing over $10M ARR, powered by a blend of automation, creativity, and data. He reveals how Pepper uses AI agents to write, edit, and even refresh old content — and why the next big wave isn’t SEO, it’s GEO: Generative Engine Optimization.
8 episodes
