Entrepreneurship Handbook Weekly Wrapup for 9/26/2025

Everyone’s a Bot, No One Can Sell, and You’re Still Not Funded

Author

Entrepreneurship Handbook
September 26, 2025

This week’s stories are a little unhinged — but that’s fitting, because so is the current startup landscape. If you’ve ever wondered why your deck flops, your early startup feels like a joke, or your smartest strategy just alienates investors… these are for you.

OpenAI’s CEO Finally Admits That Everyone On the Internet is a Bot

ehandbook.com/openais-ceo-finally-admits-that-everyone-on-the-internet-is-a-bot-a63e543dcfdc?sk=86ac99398d018760a864e727cb19c55e

Your First Attempt at a Startup Is Supposed to Be Terrible

ehandbook.com/your-first-attempt-at-a-startup-is-supposed-to-be-terrible-9f3a39f45d3f?sk=9a106fde6bec4a0c21f7d26bd208c785

The Bootstrapped Billionaire Startup Advice You Probably Can’t Afford to Take

ehandbook.com/the-bootstrapped-billionaire-startup-advice-you-probably-cant-afford-to-take-d3a99860e4a3?sk=2a62fcfd163af3c0596b501416155dfa

The Challenge of Pitching an “AI-Powered” Startup

ehandbook.com/the-challenge-of-pitching-an-ai-powered-startup-7ca698ed7a39?sk=41d8e17b7712029dcbbd823858bee8c0

The Death of Caring: Why Rolling Stone Suing Google Uncovers Tech’s Real Problem

ehandbook.com/the-death-of-caring-why-rolling-stone-suing-google-uncovers-techs-real-problem-d7de04bb95f7?sk=f1ca9211e97edbd4c094aebfbd589048

Founders Can’t Sell for the Same Reason Middle Schoolers Can’t Flirt

ehandbook.com/founders-cant-sell-for-the-same-reason-middle-schoolers-can-t-flirt-80aa55dbb877?sk=6e858cbb8dbae334d0806cfc891d51eb

How to Be Worth 5x More Than Your Identical Competitor (Hint: It’s Not Marketing or Revenue)

ehandbook.com/how-to-be-worth-5x-more-than-your-identical-competitor-hint-its-not-marketing-or-revenue-6bf8b05fc742?sk=183892f15b19a8a87e8343793b69fc7f

The real moat isn’t tech. It’s the courage to do what boring founders do before they become interesting.

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