Charlie O'Donnell Charlie O'Donnell

Americans are Better Off Without TikTok But Banning It is Bad Policy

If there’s one thing that everyone can agree on with regards to the future of TikTok in the United States, it is that congressional leaders have embarrassed themselves during the questioning of TikTok’s US CEO as the government considers whether or not to ban the popular app.

Read More
Charlie O'Donnell Charlie O'Donnell

The Unbundling of Twitter

Do we retreat to our own verticals or does Twitter continue to limp along, buoyed by real-time, "Was that an earthquake?" checks?

Read More
Charlie O'Donnell Charlie O'Donnell

Grow Fast, Breakeven, or Die: How Moderate Cuts Will Kill Startups in 2023

I’m very worried about any company that has moderate growth plans for 2023 that expects to get another round of financing based on that result. To me, that has a high chance of putting off the inevitable—running out of money during a fundraising process.

It might work against all your instincts, but I can’t help but wonder if the better strategy is to go full Thelma & Louise—to accelerate your growth enough to get noticed while you’re running down the cash.

Read More
Charlie O'Donnell Charlie O'Donnell

NYC Public Schools' Move to Ban ChatGPT Exposes Adults' Failures to Teach Healthy and Responsible Technology Usage

Instead of banning the use of new technology, wouldn’t it be better to double down on the intrinsic value of actually learning something versus just copying and pasting it? There are always going to be ways to cheat the system in life. Do we curtail cheating by making it harder to cheat or do we just instill values that make people not want to take that road because it only hurts them? Let’s put honesty and hard work on a pedestal while making cheating socially unacceptable—not just something hard to get away with.

Read More
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.

Read More
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.

Read More
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.

Read More
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.

Read More
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.

Read More