2025 AI Recap & 2026 Predictions: Winners, Losers, and What's Actually Working
Fri Jan 02 2026
Happy New Year! In this episode, Matthew and Sam break down what actually happened in AI during 2025 and make predictions for what's coming in 2026.
We cover the biggest winners and losers, the apps and tools that changed how we work, who to follow for smart AI takes, what surprised us most, and where we think things are headed.
Key topics:• Why companies that stayed curious won 2025• OpenAI's fall from dominance to a three-horse race• Claude Code and why it changed everything• The tools we actually use daily (Whisper Flow, Granola, Cursor)• Why vibe coded apps are passing enterprise code reviews• Google's image generation breakthrough• Our custom CRM build and the future of back office AI• Why product managers are the winners of 2026• The coming downfall of SaaS and low-skill trades
Plus: We launch our new Run Point Magazine and Sam accidentally emails hundreds of people.
🔗 Get the Run Point Magazine: [link]🔗 Subscribe to our newsletter: [link]
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## Chapters
0:00 - Intro & Happy New Year0:39 - Biggest Winner of 2025: Curious Companies2:16 - Claude Code Changed Everything4:04 - Biggest Loser of 2025: AI Resisters5:25 - Why OpenAI Lost Ground in 20257:07 - Best App of 2025: Claude Code & Whisper Flow9:17 - Granola, Transcripts & the Transcript-to-Action Pattern10:29 - Why Cursor Won the IDE Wars11:33 - Best Thinkers to Follow: Tyler Cowen & Twitter Curation14:40 - The Run Point Magazine Launch (and Email Disaster)17:17 - Biggest Surprise: Enterprise-Grade Vibe Coded Apps20:35 - Google's Image Generation Breakthrough22:53 - Best Thing We Built: The AI-Powered CRM27:08 - Worst Things We Built: Complex RAG Systems28:52 - 2026 Predictions: Product Managers Win Big30:37 - 2026 Loser Prediction: Half of SaaS Dies32:28 - Why Low-Skill Home Services Are in Trouble35:04 - AGI Is Basically Here (Contrarian Take)38:10 - Why "Vibe Coding" Will Get Rebranded38:38 - 2026 Resolutions: Back Office AI & Continuous Learning41:01 - Wrap Up
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Happy New Year! In this episode, Matthew and Sam break down what actually happened in AI during 2025 and make predictions for what's coming in 2026. We cover the biggest winners and losers, the apps and tools that changed how we work, who to follow for smart AI takes, what surprised us most, and where we think things are headed. Key topics:• Why companies that stayed curious won 2025• OpenAI's fall from dominance to a three-horse race• Claude Code and why it changed everything• The tools we actually use daily (Whisper Flow, Granola, Cursor)• Why vibe coded apps are passing enterprise code reviews• Google's image generation breakthrough• Our custom CRM build and the future of back office AI• Why product managers are the winners of 2026• The coming downfall of SaaS and low-skill trades Plus: We launch our new Run Point Magazine and Sam accidentally emails hundreds of people. 🔗 Get the Run Point Magazine: [link]🔗 Subscribe to our newsletter: [link] --- ## Chapters 0:00 - Intro & Happy New Year0:39 - Biggest Winner of 2025: Curious Companies2:16 - Claude Code Changed Everything4:04 - Biggest Loser of 2025: AI Resisters5:25 - Why OpenAI Lost Ground in 20257:07 - Best App of 2025: Claude Code & Whisper Flow9:17 - Granola, Transcripts & the Transcript-to-Action Pattern10:29 - Why Cursor Won the IDE Wars11:33 - Best Thinkers to Follow: Tyler Cowen & Twitter Curation14:40 - The Run Point Magazine Launch (and Email Disaster)17:17 - Biggest Surprise: Enterprise-Grade Vibe Coded Apps20:35 - Google's Image Generation Breakthrough22:53 - Best Thing We Built: The AI-Powered CRM27:08 - Worst Things We Built: Complex RAG Systems28:52 - 2026 Predictions: Product Managers Win Big30:37 - 2026 Loser Prediction: Half of SaaS Dies32:28 - Why Low-Skill Home Services Are in Trouble35:04 - AGI Is Basically Here (Contrarian Take)38:10 - Why "Vibe Coding" Will Get Rebranded38:38 - 2026 Resolutions: Back Office AI & Continuous Learning41:01 - Wrap Up