Archive - Venture Reflections

Uncomfortable and Unanswered Questions I Have as an AI Investor

I've been in a lot of rooms with a lot of smart people who are working on the future of AI and a few important questions still feel unanswered to me.

May 6 •

April 2025

What Does It Mean to Be a Venture Capitalist Today?

Some thought on our business and where things might go from here

Apr 9 •

February 2025

What if the Current Tech IPO Drought isn't a Drought but the New Normal for Venture?

What happens in a world where we have fewer, bigger IPOs that take longer to mature?

Feb 25 •

January 2025

Four Reasons People Leave Venture Firms

Every departure is unique but most fall into one of four categories

Jan 7 •

December 2024

Four Blog Posts I Didn't Publish This Year

A number of blog posts didn't get past the cutting room floor this year - here's why.

Dec 16, 2024 •

Three Future States of the Early-Stage VC Ecosystem

Sharing a slide from our annual meeting that sums up one of the things I've been thinking about for the majority of this year.

Dec 3, 2024 •

October 2024

No Longer Emerging, Not Yet Established

The Emerging Manager Circle was a good time to reflect on my own journey in venture capital and life as an "elder millenial" fund manager

Oct 18, 2024 •

September 2024

You're Not the Same Fund Manager You Were When You Started

A lot changes in terms of where you were when you started your fundraising journey and where you are today.

Sep 26, 2024 •

August 2024

Today's Era of AI Investing Reminds Me of 2000 Internet Investing (but not because it's a bubble)

Feels like we are in the midst of shift from unbridled enthusiasm to realizing it will take some time to fully realize the promise of AI.

Aug 3, 2024 •

July 2024

The last bit of runway has a way of focusing energy and attention on the things that matter. I want to find a way to get more companies to operate with…

Jul 12, 2024 •

June 2024

Why It's Hard for Small Venture Funds to "Play the Game on the Field" in AI Investing

I'm not sure the analogy of playing the game on the field works for small funds who are thinking about how to navigate the world of AI.

Jun 6, 2024 •

April 2024

What Happens If I Don't Make This Investment?

Sometimes there's nothing wrong with your company or pitch, the other person just doesn't feel like passing will be a decision they regret.

Apr 11, 2024 •

#nojs-banner { position: fixed; bottom: 0; left: 0; padding: 16px 16px 16px 32px; width: 100%; box-sizing: border-box; background: red; color: white; font-family: -apple-system, "Segoe UI", Roboto, Helvetica, Arial, sans-serif, "Apple Color Emoji", "Segoe UI Emoji", "Segoe UI Symbol"; font-size: 13px; line-height: 13px; } #nojs-banner a { color: inherit; text-decoration: underline; } This site requires JavaScript to run correctly. Please turn on JavaScript or unblock scripts