EP 20: What VCs Won’t Tell You About Getting Funded with Charlie O’Donnell

In Episode 20 of AI in NYC, we welcome back our original guest — Charlie O'Donnell — to talk about his upcoming book 'Founder Unfriendly: What Investors Won't Tell You About Getting Funded.' Charlie has spent years in the NYC venture ecosystem helping founders navigate the opaque, often misleading world of fundraising, and this book is his attempt to arm the 99% of founders who aren't insiders with the real playbook.

Charlie breaks down why the feedback you get from VCs almost never reflects the real reason they passed, how junior associates can inadvertently string you along, and why the fundraising process actually starts way before you ever pitch a deck — possibly as far back as high school. He also shares a fascinating look at how he used AI to organize and structure a 250-page book from a messy list of inside-joke chapter titles.

We also discuss the emotional arc of founding a company — including why the day you announce your startup might be the most dangerously misleading day of all. If your network congratulated you but didn't offer a single customer intro, that's a signal worth paying attention to. Whether you're a first-time founder or a repeat entrepreneur, this episode is packed with honest, practical insight you won't hear in a typical VC blog post.

Sponsored by BePresent (bepresentapp.com) — the #1 app in its category that uses social media engagement techniques to keep you OFF your phone.

Also: join us April 15th at 5:30 PM for our first in-person Cloud Code class for non-technical people in NYC!