Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada

2025-05-18 · 61 min · 70 entities

episode page audio

Asserted relationships

→ references Features product

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://github.com/features/copilot
→ references The Epic Split person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://en.wikipedia.org/wiki/The_Epic_Split
→ references Google Now person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://en.wikipedia.org/wiki/Google_Now
→ references Brief History Intelligence Evolution Breakthroughs book

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351
→ hosted by Lenny Rachitsky person

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evidence rules-v4
Feed author/publisher: Lenny Rachitsky
→ recommended Brief History Intelligence Evolution Breakthroughs book

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351
→ recommended Brief History Intelligence Evolution Breakthroughs book

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351
→ works at Shopify company

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CEO of Shopify
→ works at Shopify company

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CEO of Shopify
→ works at StackBlitz company

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evidence rules-v4
CEO of StackBlitz
→ works at StackBlitz company

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CEO of StackBlitz
→ works at Vercel company

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CEO of Vercel
→ works at Vercel company

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CEO of Vercel
→ discusses Technology company

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Feed category: Technology
→ discusses Business concept

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Feed category: Business
→ discusses Entrepreneurship concept

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evidence rules-v4
Feed category: Entrepreneurship
→ references penname.co website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://penname.co/
→ references replit.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://replit.com/
→ references cursor.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://cursor.com/
→ references lovable.dev person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://lovable.dev/
→ references bolt.new website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://bolt.new/
→ references granola.ai website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://granola.ai/
→ references deepseek.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://deepseek.com/
→ references Welcome website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://home.google.com/welcome
→ references Alan Kay person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://brainyquote.com/quotes/alan_kay_100831
→ references robinhood.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://robinhood.com/
→ references ebay.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://ebay.com/
→ references lens.google website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://lens.google/
→ references capitalone.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://capitalone.com/
→ references Saturday Night Live person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://nbc.com/saturday-night-live
→ references microsoft.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://microsoft.com/
→ references Ai Frontiers person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://microsoft.com/en-us/research/lab/ai-frontiers
→ references South Park Gnomes Season 2 Ep 17 website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://southpark.cc.com/episodes/13y790/south-park-gnomes-season-2-ep-17
→ references Microsoft Excel World Championship person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://fmworldcup.com/microsoft-excel-world-championship
→ references 67e940b7 Aab2 46ce A62b C7308cde9de7 website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://max.com/shows/hacks/67e940b7-aab2-46ce-a62b-c7308cde9de7
→ references sindhuvee.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://sindhuvee.com/
→ references natebargatze.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://natebargatze.com/

Entities found in this episode

websites 32

mentioned penname.co website

0.45

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://penname.co/
mentioned replit.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://replit.com/
mentioned cursor.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://cursor.com/
mentioned bolt.new website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://bolt.new/
mentioned granola.ai website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://granola.ai/
mentioned deepseek.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://deepseek.com/
mentioned Welcome website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://home.google.com/welcome
mentioned robinhood.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://robinhood.com/
mentioned ebay.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://ebay.com/
mentioned lens.google website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://lens.google/
mentioned capitalone.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://capitalone.com/
mentioned microsoft.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://microsoft.com/
mentioned South Park Gnomes Season 2 Ep 17 website

0.45

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://southpark.cc.com/episodes/13y790/south-park-gnomes-season-2-ep-17
mentioned 67e940b7 Aab2 46ce A62b C7308cde9de7 website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://max.com/shows/hacks/67e940b7-aab2-46ce-a62b-c7308cde9de7
mentioned sindhuvee.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://sindhuvee.com/
mentioned natebargatze.com website

0.45

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://natebargatze.com/
references penname.co website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://penname.co/
references replit.com website

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://replit.com/
references cursor.com website

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://cursor.com/
references bolt.new website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://bolt.new/
references granola.ai website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://granola.ai/
references deepseek.com website

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://deepseek.com/
references Welcome website

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://home.google.com/welcome
references robinhood.com website

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://robinhood.com/
references ebay.com website

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://ebay.com/
references lens.google website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://lens.google/
references capitalone.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://capitalone.com/
references microsoft.com website

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://microsoft.com/
references South Park Gnomes Season 2 Ep 17 website

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://southpark.cc.com/episodes/13y790/south-park-gnomes-season-2-ep-17
references 67e940b7 Aab2 46ce A62b C7308cde9de7 website

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://max.com/shows/hacks/67e940b7-aab2-46ce-a62b-c7308cde9de7
references sindhuvee.com website

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://sindhuvee.com/
references natebargatze.com website

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://natebargatze.com/

persons 16

mentioned The Epic Split person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://en.wikipedia.org/wiki/The_Epic_Split
mentioned Google Now person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://en.wikipedia.org/wiki/Google_Now
references The Epic Split person

0.77

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://en.wikipedia.org/wiki/The_Epic_Split
references Google Now person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://en.wikipedia.org/wiki/Google_Now
mentioned Lenny Rachitsky person

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evidence rules-v4
Feed author/publisher: Lenny Rachitsky
hosted by Lenny Rachitsky person

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evidence rules-v4
Feed author/publisher: Lenny Rachitsky
mentioned lovable.dev person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://lovable.dev/
mentioned Alan Kay person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://brainyquote.com/quotes/alan_kay_100831
mentioned Saturday Night Live person

0.45

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://nbc.com/saturday-night-live
mentioned Ai Frontiers person

0.45

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://microsoft.com/en-us/research/lab/ai-frontiers
mentioned Microsoft Excel World Championship person

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://fmworldcup.com/microsoft-excel-world-championship
references lovable.dev person

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://lovable.dev/
references Alan Kay person

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://brainyquote.com/quotes/alan_kay_100831
references Saturday Night Live person

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://nbc.com/saturday-night-live
references Ai Frontiers person

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://microsoft.com/en-us/research/lab/ai-frontiers
references Microsoft Excel World Championship person

0.38

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://fmworldcup.com/microsoft-excel-world-championship

companys 11

mentioned Shopify company

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CEO of Shopify
mentioned StackBlitz company

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evidence rules-v4
CEO of StackBlitz
mentioned Vercel company

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evidence rules-v4
CEO of Vercel
mentioned Technology company

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evidence rules-v4
Feed category: Technology
works at Shopify company

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evidence rules-v4
CEO of Shopify
works at Shopify company

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CEO of Shopify
works at StackBlitz company

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evidence rules-v4
CEO of StackBlitz
works at StackBlitz company

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evidence rules-v4
CEO of StackBlitz
works at Vercel company

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evidence rules-v4
CEO of Vercel
works at Vercel company

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evidence rules-v4
CEO of Vercel
discusses Technology company

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evidence rules-v4
Feed category: Technology

concepts 5

mentioned Business concept

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Feed category: Business
mentioned Entrepreneurship concept

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Feed category: Entrepreneurship
discusses Business concept

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evidence rules-v4
Feed category: Business
discusses Entrepreneurship concept

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Feed category: Entrepreneurship
mentioned CPO concept

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evidence rules-v4
CPO

books 4

mentioned Brief History Intelligence Evolution Breakthroughs book

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evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351
references Brief History Intelligence Evolution Breakthroughs book

0.77

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351
recommended Brief History Intelligence Evolution Breakthroughs book

0.50

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351
recommended Brief History Intelligence Evolution Breakthroughs book

0.50

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351

products 2

mentioned Features product

0.90

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://github.com/features/copilot
references Features product

0.77

evidence rules-v4
Link in episode "Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada": https://github.com/features/copilot

Episode description as stored

Aparna Chennapragada is the chief product officer of experiences and devices at Microsoft, where she oversees AI product strategy for their productivity tools and work on agents. Previously, she was the CPO at Robinhood, spent 12 years at Google, and is also on the board of eBay and Capital One. What you’ll learn: 1. How “prompt sets are the new PRDs” and why prototyping with AI is now essential for effective product development 2. The three key characteristics of AI agents: autonomy (delegation of tasks), complexity (handling multi-step challenges), and natural interaction (conversing beyond simple chat) 3. Why NLX (natural language experience) is the new UX, requiring deliberate design principles for conversational interfaces 4. Why the PM role isn’t dying in the AI era—it’s evolving to emphasize tastemaking and editing 5. How living “one year in the future” can be operationalized with programs like Microsoft’s Frontier 6. How even traditional enterprises can balance cutting-edge AI adoption with appropriate governance through dual-track approaches 7. Insights on leadership differences between Microsoft’s Satya Nadella (known for multi-level thinking and early trendspotting) and Google’s Sundar Pichai (mastery of complex ecosystems) 8. The vision for human and AI collaboration in the workplace, where people and agents achieve outcomes greater than either could alone 9. A practical framework for evaluating zero-to-one product opportunities — Brought to you by: Eppo —Run reliable, impactful experiments Pragmatic Institute —Industry‑recognized product, marketing, and AI training and certifications Coda —The all-in-one collaborative workspace — Where to find Aparna Chennapragada: • X: https://x.com/aparnacd • LinkedIn: https://www.linkedin.com/in/aparnacd/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Aparna Chennapragada (04:28) Aparna’s stand-up comedy journey (07:29) Transition to Microsoft and enterprise insights (10:00) The Frontier program and AI integration (13:28) Understanding AI agents (17:59) NLX is the new UX (22:28) The future of product development (31:16) Building a custom Chrome extension (35:45) Leadership styles of Satya and Sundar (37:47) Counterintuitive lessons in product building (41:20) Inflection points for successful products (45:16) GitHub Copilot and code generation (48:34) Excel’s enduring success (50:27) Pivotal career moments (54:55) The future of human-agent collaboration (56:25) Lightning round and final thoughts — Referenced: • Google Lens: https://lens.google/ • Saturday Night Live : https://www.nbc.com/saturday-night-live • Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/ • Robinhood: https://robinhood.com/ • eBay: https://www.ebay.com/ • Capital One: https://www.capitalone.com/ • Microsoft: https://www.microsoft.com/ • Aparna’s LinkedIn post about enterprise vs. consumer: https://www.linkedin.com/posts/aparnacd_every-enterprise-user-feature-has-a-shadow-activity-7321176091610542080-8X-E/ • The Epic Split: https://en.wikipedia.org/wiki/The_Epic_Split • AI Frontiers: https://www.microsoft.com/en-us/research/lab/ai-frontiers/ • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Deepseek: https://www.deepseek.com/ • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/ • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Tobi Lütke’s post on X about reflexive AI: https://x.com/tobi/status/1909251946235437514 • GitHub Copilot: https://github.com/features/copilot • Sundar Pichai on LinkedIn: h