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.

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.

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.

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.

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.