Charlie O'Donnell Charlie O'Donnell

How Generative AI is Going to Change Your Life and Mess Everything Up in the Process

Let’s not make the same mistakes we made with social media. As VC funds rush to fund the arms race of generative AI, they should be thinking about responsibility first—as it is not only core to the long-term viability of the technology as a business, but it’s just the right thing to do. Any investor that isn’t asking ethical and safety questions about the AI they’re investing in is not only dropping the ball as an investor but as a person as well.

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Charlie O'Donnell Charlie O'Donnell

I'll Fund a Startup n00b But Here's How Not to Look Like One

As insiders, we feel like the community is super open and transparent that we can’t imagine not knowing what someone’s pitch should look like or how someone could miss out on the language of fundraising, but actually, it’s super easy.

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Charlie O'Donnell Charlie O'Donnell

Pro-Choice is a Fiduciary Responsibility

If startup success and asset class performance correlate with having the best and brightest available and fully prepared for the kind of work that building a startup requires, you’re going to shrink that talent pool unless they can choose when it works for them to start a family.

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Charlie O'Donnell Charlie O'Donnell

Want to Recruit Top Talent? Start Thinking of Work as a Product That You Sell.

When you flip the script and you realize you’re selling your work opportunity to a discerning customer, you put yourself not only in sales mode, but in product marketing mode—making sure that what you’re offering clearly meets the customers’ need and that it’s fairly obvious to them that it does.

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Charlie O'Donnell Charlie O'Donnell

An Early Investor's Postmortem of The Wing

I’m writing because a lot of how the story played out obscures real lessons to be learned here, oversimplifies the issues, and scapegoats just one person—all while holding investors pretty blameless.

Plus, it bothers me that it gives the impression that, if you’re a female founder and you become the face of your company, you’ll inevitably get taken down—that anything short of unimpeachable success means becoming a target and getting kicked to the curb in a spectacularly disastrous fashion.

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