Brad Feld

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.

Matt – thank you for making me snort or laugh out loud several times on the days you write.


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.

There is no doubt that we are in the middle of, well, whatever you want to call it. “Correction” and “Choppy Waters” is probably a generous phrase for what is going on.

Having lived through this as an entrepreneur in 1987, an entrepreneur and VC in 2001, a VC in 2008, and a VC today, I embrace that this is just part of the entrepreneurial and economic cycle. I also know that many people freak out at this moment. If you’ve never been through this (like I hadn’t in 1987), it can be terrifying. If you are experienced and suddenly find yourself caught flat-footed for any number of reasons, it can be equally terrifying.

I no longer believe in clichés or prognostications such as “make sure you have three years of money in the bank” or “do a RIF quickly and deeply regardless of the situation you are in.” Instead, I think it is crucial for each company to understand its current reality clearly and make rapid and appropriate adjustments. This could mean “do a RIF quickly and deeply or “make sure you have three years of money in the bank,” but there are many other things to consider and do.

I’ve been involved in companies that have used these moments to gain huge market share from failing competitors. I’ve also been in companies that, in these moments, simply failed. I’ve been involved in companies that made adjustments, soldiered through, and came out the other side stronger. And, I’ve invested in brand new companies founded during these periods that ended up creating entirely new categories and extremely successful companies.

I expect that’s the tone of what we will discuss on 7/14 as part of Bolster’s Speaker Series about the VC Perspective on Navigating Choppy Waters. Fred Wilson has been through this many times, and his post on Amy and my 29th anniversary in Staying Positive is a wonderful perspective. Martina Lauchengco and Heather Hiles are long-time operators turned VCs who have also been through many cycles.

Join us on 7/14 @ 3pm ET for a discussion on Navigating Choppy Waters that hopefully will not be full of the same old clichés currently making the rounds.


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!


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.

Effective boards are critical at this moment in the entrepreneurial ecosystem. While I hope this downturn is short, I think it will be long and painful. In either case, highly functioning boards can help startups navigate this moment, while dysfunctional and weak boards can accelerate the demise of startups.

If you have a board of directors, want to have a well functioning one, are a director, or want to be a director, I encourage you to grab a copy of Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors.


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.”

Now, I’m not encouraging anyone to do a down round if unnecessary., especially when many existing investors are currently willing to add on additional dollars at the most recent valuation. If you can do this cleanly, take the money.

Rather, when you have a choice between a financing at a lower valuation and a financing with all kinds of crazy structure to try to maintain a previous valuation, negotiate the best price you can but do a clean financing with no structure.

If you don’t know what I mean by structure, they are terms like:

  • Multiple liquidation preferences (you’ll start seeing lots of 2x and 3x on new money)
  • Participating preferred on new money
  • Weird ratchets (other than the typical weighted average), including full ratchets, on next round financings
  • Annual preferred return, including PIK and cash pay on new money
  • Blocks on all kinds of things that a new investor should not have blocking rights on

… and a bunch of other things.

Sometimes, given your syndicate configuration, you have no choice but to take structure in a new round. But if you can do a clean financing at a lower price, I always think that’s a better option for everyone (founders, employees, and existing investors.)

While my optimistic personality hopes this downturn/adjustment is short-lived, I fear it won’t be. So, as an entrepreneur, I encourage you to deal with reality.


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.

Sometime in the fall, Matt Blumberg (Bolster CEO) approached me about doing a 2nd Edition of Startup Boards. Matt and I were on the board together of Return Path, his previous company, for almost 20 years. So when Mahendra Ramsinghani came out with the 1st Edition of Startup Boards in 2013, Matt gave me plenty of feedback on the book. Then, in fall 2021, he correctly suggested that the book needed a significant refresh.

While I always felt the 1st Edition was an important book, I never loved it. Mahendra and I worked hard on it, but I felt like I forced a lot of my writing at some point. Long-time readers of this blog know I had an extended depressive episode in the first half of 2013, and this book was one of the chores that I felt like I just had to get done in that period. Mahendra was kind and patient with me, but I’m sure there were moments when he wanted to scream something like, “Brad, will you just do the writing you said you’d do so we can get this book finished?”

So, we decided to do a 2nd Edition which is now finished and shipping on 6/15. I’m psyched about it. Matt contributed a lot of new content, and I had a chance to rework and refactor the entire book. I had plenty of energy for it, and, given that I’ve written a few more books and thousands of blog posts since 2013, my writing has continued to improve.

Early in the refactoring, we got feedback from several women that the 1st Edition wasn’t very accessible to them because all the sidebars and quotes were from men. So I made a Google Sheet of all the sidebars and quotes, and my brain broke for long enough that I had to go for a walk. So even though I thought I was self-aware and engaged in gender equity in tech in 2013, my actions, at least concerning this book, didn’t match my words.

Subsequently, we replaced about 50% of the sidebars and quotes with new ones from women and people of color. We also changed the pronoun dynamics to use the Singular They, which I am trying to do in all my writing (if you are interested in this topic, Khan Academy has an awesome video.)

Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors 2nd edition launch day is 6/15. If you are interested, pre-order it now.


Summer Vacation

Jun 14, 2021
Category Random

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.

If you want a hint, I’m taking inspiration from two books. The first is one of my favorite books: Zen and the Art of Motorcycle Maintenance. The other is from Michael Lewis’ awesome new book The Premonition: A Pandemic Story

Whenever I’m writing a lot, I read a lot, so you can follow along with what I’m reading at Goodreads if you want.


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.

Dave walked into Brad’s office after calculating preliminary financial results for January. Up to this point, we had mostly broken even, but the news was grim: we had lost $10,000 in one month. We had not seen it coming, and it took some effort for us to untangle what had gone wrong. Dave had been spending most of his time managing the part-time developers, who were primarily working on future products, instead of billing hours to clients. Brad had been selling computer equipment, which had low gross profit margins, instead of billing hours to clients. Much of our revenue for the month had come from one highly productive though erratic undergraduate developer, Mike, who was working on a billable client project.

Before we had a chance to figure out what to do, Mike quit, citing a need to focus on his studies. Now we had no choice: we fired everyone, shut down our month-to-month office, sold all the office furnishings, and moved the business to our apartments in downtown Boston. It was gut-wrenching. Brad wondered whether we had failed just as we got started. Dave worried about paying rent. We had long discussions about the future of the business, including whether or not to continue.

But we did have billable projects. We no longer had to spend our time managing people and had figured out where our bread was buttered. Results were good enough in February to calm our nerves and even better in March. Just as important, we had learned some crucial lessons and settled on a very different idea about how we would move forward with the business. The experience of hitting bottom and the lessons we learned became deeply ingrained in our brains and our company culture as we more methodically and progressively built the firm.

Fast-forward thirty years, when we were in the midst of writing this book, and Dave was reading Thus Spoke Zarathustra. He encountered a passage that said the highest mountains rise from the sea, and that fact is “inscribed…on the walls of their summits.” Because of our experience at Feld Technologies—and many times since—we knew immediately that this had to be a chapter in the book. We imagined the solace and instruction it might have offered us to have seen (and understood) this quote, to have read a short essay like the one in our chapter Hitting Bottom, where the starkness and promise of the situation are presented in black and white, or to have heard Walter Knapp’s story of the crash and rebirth of Sovrn, a genuinely disruptive company.

That is how we wrote most of the chapters and how this project began. In reading Nietzsche, we noticed ideas that reminded us of situations, questions, and concerns that frequently arose in our entrepreneurial and venture investment experience. Nietzsche had a way with words, and we found that some ideas were nicely encapsulated and phrased. We started playing with expanding upon his pithy aphorisms and gathering stories from entrepreneurs, and it clicked.

Feld Technologies never became a disruptive company, despite our ambitions. It plateaued at around $2 million in revenue before we sold it in 1993. Because we had built a solid foundation for a certain kind of success, we never again hit a deep low point, and consequently never again had the painful opportunity to rethink our premises. This point, too, is covered in Hitting Bottom and illustrates why we did not just skip Nietzsche, write some essays, and assemble some entrepreneur stories. Nietzsche—sitting or walking alone, in pain, almost blind—thought deeply and managed to share these thoughts with the world. We tried to follow his lead, thinking hard and pondering additional angles and situations to which the quote might apply. We want you to do the same, as you keep in mind that Nietzsche’s works have been highly influential throughout the 20th century and into the 21st.

In business and entrepreneurship literature, inspiration is sometimes more helpful than instruction. Though there is plenty of how-to information in this book, we aim to give you food for thought from a different perspective. We address issues of leadership, motivation, morals, creativity, culture, strategy, conflict, and knowledge. We push you to think about what you and your enterprise are made of. We expect you to question and ponder these ideas, not just put them into action. If we are successful, you will sometimes get angry and at other times feel pride. At times you will wonder what you really know, and at other times you will charge forward. We hope that the combination of Nietzsche’s colorful language, our elaborations, and some stories from entrepreneurs will offer you intellectual, emotional, and entrepreneurial inspiration.

Nietzsche was not a fan of commercial activity or businesspeople. He saw the former as crass and the latter as lacking nobility. However, we suspect that if Nietzsche were alive today, he would view entrepreneurs differently. He adored intensity and fervor, deeply valued those who create things, and wrote at length about “free spirits” who do not feel bound to tradition or cultural norms. Nietzsche viewed his mission as the “revaluation of all values,” and he intended to disrupt the entire moral tradition of Europe in the late 19th century.


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.

The founders of each company talked and, in between efforts to decimate the other, agreed it might be worth merging to survive. This guy named Greg Sands at a firm called Sutter Hill had met with both and was interested in the category and encouraged them to merge, at which point he’d fund the combined company. Fred called me and said, “Let’s figure out a deal.” I said, “They are both worthless right now – how about 50/50?” Fred responded with, “I have more money invested in Return Path than you do in Veripost – how about 55/45.” I answered, “Deal.” So for the deal, investors on both sides converted to common, we split the combined company 55/45, Matt became CEO, and Greg led a new Series A financing into the combined company. Twenty years later, we sold the business, a $100 million, profitable company, to Validity. Matt was still CEO. Fred, Greg, and I were still on the board.

Last year, Matt started a new company called Bolster. He co-founded it in partnership with High Alpha (we are LPs) and SVB. Soon thereafter, USV (Fred’s firm – we are LPs) and Costanoa (Greg’s firm – we are LPs) invested. It’s off to a great start. If you are looking to expand your leadership team or board, are looking for a part-time executive role or board role, or are an investor looking for fractional executives to join your portfolio companies, you should become part of the Bolster network right now.

I’ve worked with Matt for over 20 years and have experienced many ups and downs. His hard-won lessons from Return Path show up in Startup CEO: A Field Guide to Scaling Up Your Business.

For lessons from Matt and his Return Path management team, many of who are now execs at Bolster, you want to read Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams. When I saw the outline for Startup CXO, I grinned a wry smile. The book is 132 chapters broken into 11 sections. After the intro, the following sections are written by each exec.

  • Finance – Chief Financial Officer – Jack Sinclair
  • People – Chief People Officer – Cathy Hawley
  • Marketing – Chief Marketing Officer – Nick Badgett and Holly Ennerking
  • Sales – Chief Revenue Officer – Anita Absey
  • Business Development – Chief Business Development Officer – Ken Takahashi
  • Customers – Chief Customer Officer – George Bilbrey
  • Product – Chief Technology Officer and Chief Product Officer – Shawn Nussbaum
  • Privacy – Chief Privacy Officer – Dennis Dayman
  • Operations – Chief Operating Officer – Jack Sinclair

There’s a final part on The Future of Fractional Executive Work with a chapter by a different leader for each area above. Matt’s writing shows up regularly throughout, including an ending chapter for each section titled CEO-to-CEO Advice.

Each chapter is two to five pages long. It’s tons of information, organized well, in tight, bite-sized chunks. For example, here are the chapters in Part Five: Sales by Anita Absey (p. 247-302)

  • Ch 54: In the Beginning: From Prospect to Customer
  • Ch 55: Hiring the Right People
  • Ch 56: Profile of Successful Salespeople
  • Ch 57: Some Myth Busting
  • Ch 58: Compensating Sales Team Members
  • Ch 59: Pipeline
  • Ch 60: Scaling the Sales Organization
  • Ch 61: Scaling Your Team Through Culture
  • Ch 62: Scaling Sales Process and Methodologies
  • Ch 63: Scaling the Operating System
  • Ch 64: Marketing Alignment
  • Ch 65: Market Assessment and Alignment
  • Ch 66: Expanding Distribution Channels
  • Ch 67: Geographic Expansion
  • Ch 68: Pricing and Packaging
  • Ch 69: CEO-to-CEO Advice

The brilliance of this book is that everyone on your leadership team, including the CEO, should read it and then discuss it. Pick one section each week. At the end of a quarter, the entire team will have discussed all the functional roles, have a deeper understanding of expectations and responsibilities, use a common language for talking about what people are doing, and be able to adapt things to your own company. Also, if you aspire to be a CXO – you can figure out your career path by understanding the whole functioning of the relevant and adjacent departments.

I’m going to encourage every leadership team I work with to take this approach with Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams.

Matt and team, thanks for writing this!