…Said no one ever, at least at first. Let me try to get you to a happier place about this — and also keep you from making the biggest mistake I’ve seen other entrepreneurs make in down round negotiations. You’ve toiled away since the last round. It’s been a super…

Instant delivery! Fast fashion! Buy it now! As as society, we seem to be moving continuously towards immediate gratification. Unfortunately, that isn’t going to be possible for some of our most pressing problems. We face some massive, fundamental, and unprecedented challenges, challenges for which solutions will be hard and complex…

One of my brilliant former students called me last week to ask me whether he should take advantage of a ‘free loan from the company’ to exercise the options of the startup he is with. The conversation was a reminder that even brilliant engineers can be unaware of the downsides…

This is a topic that has come up in a number of our portfolio companies of late. And, as the parent of a child who identifies as trans and non-binary, I’m also probably more attuned than most to the inequities as well as personally passionate about creating change. So, in…

Note: I wrote this five years ago. I’m reposting it today in honor of Trans Awareness Week and Trans Day of Remembrance. I have been thinking for weeks about the suicide of teenager Leelah Alcorn, and her wish that her death mean something. I’m sharing my story about what it has been like to be the parent of a trans kid in the hopes that if you are a parent struggling to…

This CEO is a master at interacting with her board. Here’s how she does it. My phone started ringing. It was a Saturday night in May around 10pm and I was hanging out with my daughter, watching a movie. She hit pause and said, “Let me guess, it’s Aicha.” It…

I just had an exchange this morning that was sadly similar to too many exchanges I’ve had in the past. Here’s how they tend to go. The CEO and board members of a company are searching to fill an open seat. They reach out to me as a known connector…

Hello Readers! I’m ending the year with a grab-bag of VC-related questions and answers. Keep those questions coming to helpmeheidi@threshold.vc, and happy holidays! — Heidi Q: I’ve heard that when raising from a VC you should never take a meeting with anyone but a partner, because they are the only…

Dear Heidi, I have a killer app that I think is going to be HU-U-U-UGE. I’ve been working on it every night and weekend for the last six months, and I think I’m ready to take the plunge, raise some money and quit my job to work on this full…