The Brilliance of Bloomberg's Matt Levine

Of all the business and technology writers out there, including bloggers, I think the best one, at this moment, is Matt Levine. He’s the only person currently writing on Planet Earth that I find myself reading every word of everything he writes. For the last few months, he has been mostly writing about three topics: The Twitter Elon Musk Soap Opera Why (and How) Much of Crypto Is A Plain, Old, Ponzi Scheme Other Crazy and Fucked Up Things in Finance For a flavor of his writing, read the following 11 chapters of Matt’s writing (listed in chronological order). Then, subscribe to his newsletter and get a magnificent medium-form article in your inbox every other day or so.

July 18, 2022 · 2 min

Navigating Choppy Waters

In the last seven months, the venture / entrepreneurial world has gone from “the only thing that matters is massive growth” to “the world is going to end.” For perspective, all you need to do is look at a dozen high-flying IPOs from 2020 or 2021 to see that the peak happened just before Thanksgiving. The private markets lag the public markets. That’s not new. This time around, the lag was about a quarter, as many VCs started to talk about what was happening around the beginning of Q2.

June 30, 2022 · 3 min

The Evolution of Apple macOS

My partner Ryan shared this with me. It’s a 10-minute video showing the evolution from System 0.97 to macOS 13 Ventura. I had an original Macintosh 128K which is now enjoying its retirement at the Media Archaeology Lab. Enjoy!

June 23, 2022 · 1 min

Book: Startup Boards, 2nd Edition Is Available

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.

June 15, 2022 · 1 min

Down Rounds: Deal With Reality

Connie Loizos is one of the long-time tech industry writers who I respect. I don’t respond to many interview requests these days, but I’ll always talk to her. She has a good article today in TechCrunch titled Embrace the down round (it’s going to be okay, maybe). I like the quote she pulled out of me in our conversation. [Brad Feld] says his “strong belief” that “just doing a clean resetting — at whatever the valuation so that everybody is aligned and dealing with reality — is much, much better for a company.”

June 10, 2022 · 2 min

Summer Is Here

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.

June 8, 2022 · 3 min

Summer Vacation

This blog has decided to take a summer vacation. I’ve been blogging regularly since 2005 (typical 15 – 20 posts a month.) I’m going to take a break for a while. Now that The Entrepreneur’s Weekly Nietzsche: A Book for Disruptors is out, I’ve started working on my next book. I’m trying some different stuff with this new book and decided to focus all of my writing over the summer on it.

June 14, 2021 · 1 min

Why Philosophy and Entrepreneurship?

Since releasing my newest book The Entrepreneur’s Weekly Nietzsche: A Book for Disruptors I’ve been continually getting the questions “Why Philosophy and Entrepreneurship?” and “Why Nietzsche?” Dave and I cover this right off the bat in the book, so I thought I’d toss up an excerpt that addresses the question with part of my own origin story with Dave. It follows. Nietzsche? For entrepreneurs? It was the end of January 1988, about nine months since we had embarked on turning Brad’s solo consulting shop, Feld Technologies, into a real business. We were fraternity brothers and close friends and opened our first office directly across the street from our fraternity chapter house in Cambridge. We planned to use smart yet inexpensive software developers to build business application software. We employed half a dozen programmers, most of whom were undergraduates from our fraternity working part-time. We didn’t have any financing except for Brad’s credit card and the $10 with which we had purchased our common stock.

June 11, 2021 · 5 min

Startup CXO: A Field Guide to Scaling Up Your Company's Critical Functions and Teams

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.

June 9, 2021 · 5 min