Books

John McPhee’s Levels of the Game was published when I was three. I’ve read many books about tennis, but it’s still my favorite, with String Theory: David Foster Wallace on Tennis coming in a close second. Both books share extraordinary writers and a topic I can relate to, given my short but profane junior tennis career. I’ve become annoyed by the writing that ChatGPT produces. At first, I was fascinated. As I saw more of it, I began seeing patterns. After reading Stephen Wolfram’s article What Is ChatGPT Doing … and Why Does It Work? my observation shifted to impatience. Most of my ChatGPT efforts now are making it hallucinate. ...

Chris Heivly released Build the Fort: The Startup Community Builder’s Field Guide . I encourage you to get Chris’s book if you are a startup community builder or are interested in startup communities. When Ian Hathaway and I started working on The Startup Community Way: Evolving an Entrepreneurial Ecosystem , we initially talked to Chris about writing a few chapters. Chris became an extensive thought partner with Ian, and we eventually decided to write two books. The Startup Community Way would be conceptual but filled with examples to make our points, and then a second book would be a practitioner guide. ...

The 2nd Edition of my book Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors launched today. My co-authors, Matt Blumberg, the CEO of Bolster , and Mahendra Ramsinghani, were a joy to work with. While the 1st Edition was a good book, I wasn’t particularly proud of it because I didn’t feel like it was my best writing. We worked hard on this edition, and I now feel like it’s equivalent in quality to my other books. ...

About a year ago, I decided to take a summer vacation from blogging. I didn’t feel like blogging when summer ended, so I extended my blogging vacation indefinitely. I figured I’d wake up one day and feel like blogging again or not. That summer vacation (from blogging) lasted a year. Initially, I was working on a new book that I got bored of midway through the summer. I put it on the shelf with several other partially completed books. Google Docs now has a surprising number of my started but unfinished books. ...

Matt Blumberg has a new book out titled Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams . It’s a follow-up to his previous book, Startup CEO: A Field Guide to Scaling Up Your Business. I’ve been working with Matt since 2000. That year, we merged two companies: Return Path and Veripost. Matt was the co-founder/CEO of Return Path. Fred Wilson was his lead investor. I was the lead investor for Veripost. The two companies did the same thing and were the only two competitors in a nascent category called “email change of address” (Veripost’s original name was IECOA which stood for “Internet Email Change of Address”). They were bashing each other over the head in a non-existent market as the Internet bubble began collapsing. ...

I reread Enough.: True Measures of Money, Business, and Life by John C. Bogle over the weekend. I’d read it in 2012 and it had a huge impact on me. If you aren’t familiar with John C. Bogle , he founded The Vanguard Group , is credited with inventing the index fund and is a spectacular writer (every one of his books is worth reading.) He passed away in 2019 at the age of 89, but I expect his legacy will last a very long time. ...

The best businesses are data-driven and metrics-driven. Instead of simply tracking top-line metrics, every person in the organization understands their role, how they impact the business metrics, and how this impacts its larger goals. One of the biggest mistakes I see companies make is fooling themselves into thinking they are metrics-driven because they are good at reporting high-level and often lagging metrics. Companies that achieve breakout success and longevity have a much deeper and richer understanding of their business’s nuances. ...

I sort of took a Q1 Vacation last week. 2021 didn’t really feel like it started for me until January 21st. Yeah, I took a company public on January 4th, but then January 6th happened. It was a cold, dark, and anxious stretch where January felt like it had about 51 days in it. Then I was deep in SPACland and lots of deals and financings. I definitely had some “I just need to get to March 26th, and then I get a break” in my head. ...

My favorite animal is a polar bear. For some reason, I have always related to polar bears. When I’m reincarnated, I hope I come back as a polar bear. I’ve always like octopuses but never thought much about why. After reading Sy Montgomery’s incredible book The Soul of an Octopus: A Surprising Exploration Into the Wonder of Consciousness, I now know why. It’s simple – we don’t understand how they think. ...

I read G. W. Constable’s near term sci-fi book Becoming Monday. If you are a fan of near term sci-fi, AGI, or the singularity, go get a copy right now – you’ll love it. I woke up in a customer service booth. Or perhaps more accurately, since I couldn’t remember a damn thing, my new existence began in that booth. If you’re born in hell, does that make you a bad person? ...