I’m currently at the Global Entrepreneurship Congress 2025 in Indianapolis. Yesterday, at the end of the day, I spent several hours at High Alpha hanging out with my friends and then doing a Give First: The Power of Mentorship book event with them and about 150 people. One of the questions during the book talk was around mental health and entrepreneurship. I talked about my own experiences with anxiety and depression and explained that my core diagnosis, which I was diagnosed with in my 20s, was obsessive-compulsive disorder (OCD). I said that one of my goals for being open was to destigmatize mental health issues, especially in the context of entrepreneurship and mentioned that I periodically hear something like “I’m OCD and it’s my superpower” and dismissed that idea as nonsense, since OCD is an insidious thing that gets in the way of so many things in life.

A long time ago, in a galaxy far, far away, I was a CTO of a large, fast-growing public company. Well, I was a Quasi CTO in the same way the United States and the First French Republic had a Quasi War between 1798 and 1800 (basically, sort of a war; sort of a CTO … but not really.) As I rediscover my second love (my first love is Amy), I’ve relied on several mentors to help guide me. One of them is Michael Natkin, who has been helping me with Cursor in the background at a few key moments.

This played out on @bfeld on X, and I thought it was fun enough to replay it here for anyone who is struggling to get their minds around vibe coding and current AI tooling. If you are receiving this via email and the tweets/X’s aren’t showing, click through to the website as I’m still struggling to get Mailchimp working well after my hibernation. Perhaps it’s time to switch everything to WordPress…

As a voracious reader, I love a good table of contents (TOC) as the roadmap to a book. While fiction is often structured as Chapter 1, Chapter 2, Chapter 3, … Chapter N, some of the best fiction writers are creative with their TOC. Any non-fiction author who doesn’t provide a detailed table of contents TOC is missing an opportunity to help the reader understand the book’s flow before they begin reading it.

I did a talk with a private community of 100 GPs and investors in venture capital called Aces last week. It’s an off-the-record, confidential group organized by a few people, including Max Beaumont, who said I could mention him in this post. Max sent me the following summary. I asked him if I could post it, and he said yes. Thank you again for taking the time to join us yesterday, and for staying well past the scheduled end.. I could tell how meaningful the conversation was for those who stayed..

Registration for the Venture Deals Summer 2025 online, self-guided, free course by Techstars and Kauffman Fellows starts today. It’s based on the book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist. When Jason Mendelson and I wrote the first edition, one of our goals was to eliminate the massive information asymmetry between entrepreneurs and investors. Venture Deals is now in its 4th edition and has continued to be a popular and helpful book.

On Saturday, May 31st, from 3:30 to 5:00 PM in downtown Denver, I’ll have a public conversation with Phil Weiser about various topics, including technology and innovation in Colorado. We will also talk about what (and how) we’ve learned from each other over the years and how we’ve worked constructively through disagreements, conflicts, and mistakes.

I learned how to do deals from Len Fassler. Last week, I got an email from Dustin Kloempken, who sent me a few quotes he wrote down from the Berkshire Annual Meeting. One of them jumped out at me. “Turn every page. One important ingredient in the investment field that very few people do. And those people who did read every page aren’t telling you what they learned. You have to read every page.“

I’m going to have a Random Day on 5/28 at The Composition Shop in Longmont. I plan to be there from 11 am to 5 pm with a break for a lunch meeting from 1 pm to 2:30 pm. We will have copies of Give First: The Power of Mentorship in the store on sale, even though the book’s official release date isn’t until June 24th, because my Colorado friends get special bonus early bird stuff.