Alex Lieberman co-founded Morning Brew in college and grew it into one of the most-read business newsletters in the world before selling it to Business Insider. Now he’s the founder and CEO of the company Tenex. In this episode, Alex explains why distribution is becoming a durable moat, why founders and teams need to “climb Cringe Mountain,” and how he rebuilt his content process around AI without letting it produce generic slop. He walks us through every step of his Content Machine live: an Oracle that scans internal systems and the internet for content spikes, an interview panel that pulls out his real ideas, voice and style files that keep drafts sounding like him, an editorial council that scores and revises posts, and a lessons loop that learns from his feedback.

What you’ll learn:

1. Why the blank page is the biggest friction point in content creation, and how an AI Oracle eliminates it

2. How to map your current workflow before you add any AI

3. How Alex built a six-step Content Machine in Claude that goes from idea spike to publishable post

4. Why the interview step (not the drafting step) is where AI slop actually comes from

5. How to codify your voice in a Markdown file so an AI drafts in your register, not the internet’s average

6. Why your employees are your most underleveraged marketing channel right now

7. How the Tenex Creator Cup turned content creation into a team sport with a $5,000 prize pool

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In this episode, we cover:

(00:00) Introduction to Alex Lieberman

(02:35) Why Alex built a content machine

(06:56) Alex’s thoughts on AI slop

(09:00) Mapping the workflow from scratch

(13:24) The six-step Content Machine setup

(23:11) Live demo: Oracle, Interview Panel, and Writer’s Council in action

(30:38) Employee advocacy: the Tenex Creator Cup and $5K prize pool

(36:45) Lightning round: great engineers, AI use cases, slop fixes

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Tools referenced:

• Claude / Claude Code (Anthropic): https://claude.ai

• Wispr Flow (voice-to-text transcription): https://wisprflow.ai

• Notion: https://notion.so

• Linear: https://linear.app

• Slack: https://slack.com

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Other references:

• Morgan Housel: https://www.morganhousel.com

• David Perell: https://perell.com

• Shaan Puri / My First Million podcast: https://www.mfmpod.com

• Gary Vaynerchuk: https://garyvaynerchuk.com

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Where to find Alex Lieberman:

X: https://x.com/businessbarista

LinkedIn: https://www.linkedin.com/in/alex-lieberman/

Tenex: https://www.tenex.co/

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Where to find Claire Vo:

ChatPRD: https://www.chatprd.ai/

Website: https://clairevo.com/

LinkedIn: https://www.linkedin.com/in/clairevo/

X: https://x.com/clairevo

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email jordan@penname.co.

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How the founder of Morning Brew built a Claude content machine that never runs out of ideas and never sounds like slop | Alex Lieberman

How I AI (private feed for [email protected])

How the founder of Morning Brew built a Claude content machine that never runs out of ideas and never sounds like slop | Alex Lieberman