Blog - Charlie O'Donnell - Coach, Author, VC

“A phantom in a box, shadow in your head.” — White Zombie Nobody ever asked for VCs to start quoting song lyrics—but if you’re going to, it might as well be someone happily partnered for 20+ years, a longtime vegan and animal welfare advocate, and known f…

If I handed you the cash equivalent of your vested equity today — two million dollars, or whatever crazy number the last valuation of your company would imply — would you turn around and put all of it back into the current Series D?

Wait… what?

“What is all this?”

Lately I've been down a rabbit hole on the history of the commercialization of home pregnancy testing.

“I don’t know, Rob.

Founders aren’t the only ones under funding pressure.

Everybody's figuring out how to prompt an AI right now.

Some of the best operators I know are terrible in their own board meetings.

The first check I ever wrote into Edward Woodford of ZeroHash went into a company that doesn't exist anymore.

If you’re old enough to know the title reference and the image, please make sure you’re signed up for your regular colonoscopy.

I can't remember the last time I went through a drive-thru window.

Everyday, throngs of mostly junior investors join deal flow calls--regularly scheduled check-ins to "compare notes" on what's out there and being considered.

This is a Thingamabob—the main character in a children’s book that feels like it explains a lot about how startups think about their financials.

The most honest thing you can say about a formal advisor relationship is this: It's a workaround.

“Too many secrets.”

A few months back I got a backchannel reference call about a founder I'd backed.

If you haven’t already, check out my book, Founder Unfriendly: What Investors Won't Tell You About Getting Funded and my new AI fundraising coach and companion guide. _____ Strava's AI just told me I crushed the NYCRUNS half marathon in Brooklyn with my 1…

I mean… She’s the one killing all these people, right?

If you're a consumer founder who's gotten passed on by investor after investor, you've probably been told some version of "You're a little too early for us"—or you've assumed that most VCs just don't understand consumer.