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.
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.
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.
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)
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!
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.
I was pondering some things that were bothering me, specifically about crypto, but more generally about current themes around investing. I thought I’d revisit Enough. to see if it helped me work them out. I found my answer in Chapter 2: “Too Much Speculation, Not Enough Investment.”
Let’s start with Bogle’s definition of Investing and Speculating.
Investing is all about the long-term ownership of businesses. Business focuses on the gradual accumulation of intrinsic value, derived from the ability of our publicly owned corporations to produce the goods and services that our consumers and savers demand, to compete effectively, to thrive on entrepreneurship, and to capitalize on change. Business adds value to our society, and to the wealth of our investors.
Speculating is precisely the opposite. It is all about the short-term trading, not long-term holding, of financial instruments — pieces of paper, not businesses — largely focused on the belief that their prices, as distinct from their intrinsic value, will rise; indeed, an expectation that prices of the stocks that are selected will rise more than other stocks, as the expectations of other investors rise to match one’s own.
What was bothering me was simple: the narrative around many things has shifted to the far end of speculating. I don’t participate in this particular type of narrative, but I’m surrounded by it. I don’t behave as a speculator. While I invest in many things, I rarely sell anything until there is a “defined exit,” where I have a very explicit internal definition of “defined exit.”
As someone who has held private company stock in companies for longer than 20 years, been in many situations where there were no exit opportunities until suddenly there was an exit, I understand and am completely comfortable will illiquidity. And the idea of an investment.
I’m completely uninterested in speculating. In the mid-1990s, when I had a bunch of money after the sale of my first company, I bought and sold some public company stocks. I got sucked into giving some of my money to a money manager at Goldman Sachs and one at Lehman. They happily traded equities for me, which mostly just cost me fees in the end, although I covered it all with a crazy transaction into a weird Exchange Fund that GS created in 2000. I put a bunch of Exodus stock I’d gotten from the sale of a company into the fund. Exodus went bankrupt, so my contribution to the exchange fund was $0, but when the exchange fund paid out seven years later, I got 1.5x my investment. The only reason I got to play in the exchange fund was I had the GS account where they were trading stocks, and the guy I worked with offered up access to it. Totally random and completely dumb luck as I would have likely held the remaining Exodus stock I had all the way to $0. In hindsight, even writing this paragraph is more reinforcement to me of my ultimate lack of interest in this stuff.
As I watch crypto speculation expand into retail stock speculation, which then gets amplified broadly by zero-fee trading apps that aren’t really zero-fee and watch the SEC tangle itself up trying to figure out how to monitor Twitter and Reddit accounts of high profile people who clearly are playing age-old promotion games, regardless of whether or not there are actual pump and dump schemes behind their actions, I become extremely bored. This boredom has a layer of annoyance coating it, especially given the extraordinary 15 months of Covid we’ve just gone through.
Maybe as sports come back, some of this energy will shift back to sports. Now that proxy betting online has become essentially real cash betting online, even though the laws around this (at least in the US) haven’t really resolved, and everyone online has figured out how to get around all the rules, the speculating can become called “betting” again. Or maybe “betting” will just become speculating. It doesn’t really matter since they are fundamentally the same thing.
Let’s go back to Bogle. “Investing … adds value to our society, and to the wealth of our investors” and “Speculating is precisely the opposite.”
Ask yourself, “Is what I am doing adding value to our society?”
Enough has three sections: Money, Business, and Life. While I found the answer to what was bugging me in Chapter 2, the section on Life is awesome. The three chapters are:
Bogle completely nails this topic without being preachy, annoying, arrogant, or directive. As writing goes, it’s as beautiful and powerful as it gets. I strongly recommend Enough.: True Measures of Money, Business, and Life, especially if you have enough but don’t realize it.
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.
This work is hard, and while there are endless short-form posts about this on the web, there are few in-depth, comprehensive resources to help business builders figure this out.
Consequently, I’m excited about a new book called LEVERS – The Framework For Building Repeatability into Your Business, a collaboration between Amos Schwartzfarb, Trevor Boehm, Cody Simms, and Troy Henikoff. The book is a play-by-play series of frameworks that any company can use to become data and metrics-driven.
I love how the book takes the mystery out of finding repeatability by putting forward simple-to-follow instructions. However, even though the instructions are easy, the work isn’t.
Each of the authors has experience both as a founder and an investor. Amos Schwartzfarb is currently Managing Director of Techstars Austin, before which he’s helped to build six companies to nearly $1B in exit value. Cody Simms is presently SVP of Climate and Sustainability at Techstars, before which he was a Partner and SVP on Techstars’ investment team and was Techstars’ first Managing Director in Los Angeles. Trevor Boehm was formerly Program Director at Techstars Austin and Impact and then Managing Director at the Techstars Amazon Alexa Next program. And Troy Henikoff was formerly the founding member of Techstars Chicago and is now General Partner at Math Ventures.
Every entrepreneur and CEO should read LEVERS. It’s stage agnostic and will help you with at least the following things.
I highly recommend getting your copy of LEVERS – The Framework For Building Repeatability into Your Business today.
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.
We got back to Boulder on a Friday, settled into our house on Saturday, and I sort of kind of tried to disconnect (but failed) on Sunday. Monday, I had a full day of work, and a couple of things had landed on Wednesday, so I decided “fuck it” and just worked Monday, Tuesday, and Wednesday before going dark from Thursday to Sunday.
It is delicious to be back in Boulder. The weather is perfect, the birds are singing, and our meadowlark is back in our meadow, chirping away. We missed Cooper (we don’t take him to Aspen), so it has been a fun adjustment to get used to him again (and for him to get used to us.)
I had a monster week of running – mostly on trails. 65 miles with almost 4,300 ft of elevation. That’s the most I’ve done in a long time, and my body absorbed it pretty well.
When I wasn’t running, napping, or eating, I read. A lot. And there are some themes in what I’ve been reading.
Lighten Up!: A Complete Handbook for Light and Ultralight Backpacking: I knew of ultralight backpacking (and have heard the phrase a bunch recently in marketing stuff), but I didn’t really know the parameters or the style. This was a great intro.
Allen & Mike’s Really Cool Backpackin’ Book: Traveling & camping skills for a wilderness environment: Recommended by the previous book. Some new stuff, some repetition. Some ultralight. Some normal backpacking.
Ultralight Backpackin’ Tips: 153 Amazing & Inexpensive Tips for Extremely Lightweight Camping: Again recommended by the first book. I fell into the Kindle content market trap and clicked on links. Mostly repetitive, but good reinforcement on a few things.
Ask Your Developer: How to Harness the Power of Software Developers and Win in the 21st Century: Jeff Lawson and Twilio are awesome. This book is phenomenal, both as the story of Twilio with the underpinning of Jeff’s management philosophy. If you ever use the Marc Andreessen phrase “software is eating the world,” but you haven’t read this book, go read it to understand what the phrase really means. I’m going to host Jeff for two book events: one with Techstars and one with our portfolio. Yes, every entrepreneur and would-be entrepreneur should read this book.
Guantánamo Diary: Now published as The Mauritanian. Amy and I watched the movie a few weeks ago in Aspen when it came out. It was powerful. The book was even more powerful. I wish Guantanamo never existed – it’s a massive negative on American values. I wish Obama had followed through on closing it down. I hope Biden closes it down. If you disagree with me, read the book.
Lost in Startuplandia: Wayfinding for the Weary Entrepreneur: I recently did a talk for a class Ted Zoller teaches at UNC, and he recommended this book. I had it on my Kindle but had never read it. It was a fun memoir-like story of Keller Fitzsimmons’ entrepreneurial journey. Having read hundreds of these by men, I always learn a lot more now when I read one by a woman. It’s excellent.
Living with a SEAL: 31 Days Training with the Toughest Man on the Planet: Another one that had been lingering on my Kindle since 2017. Another recommendation. Hilarious, awesome, fun, and inspiring. I guessed that Seal was David Goggins pretty early on based on what I knew of Goggins. But I had no idea who Jesse Itzler was (now I do.) So, the next book I read was …
Can’t Hurt Me: Master Your Mind and Defy the Odds: Goggins is an epic specimen of a human. But I didn’t really know his story beyond his ultrarunning. It’s an incredible story at many levels. It’s not as fun as Itzler’s book but still awesome and much more inspiring. And it led me to read Itzler’s other book …
Living with the Monks: What Turning Off My Phone Taught Me about Happiness, Gratitude, and Focus: Still funny (Itzler is hilarious and writes well about his own hilarity), somewhat inspiring, but lots of fun. Not as powerful as Living with a SEAL, but now I know Itzler even better.
The Stone Sky (The Broken Earth Book 3): I listened to N.K. Jemisin’s Broken Earth trilogy on Audible while I’ve been running. This series deserves its own blog post and will get that at some point. I think Jemisin may have moved to the top of my contemporary sci-fi writer list. I realized all I was reading were books by white men, so I found a few non-white women sci-fi writers. Jemisin is a world builder at the level of William Gibson and Neal Stephenson and may even be better than them at this point. It was an incredible series.
Not All Fairy Tales Have Happy Endings: The rise and fall of Sierra On-Line: I still remember playing Mystery House on my Apple ][ and being blown away. I spent hours and hours playing Ultima. I felt naughty when I bought Softporn as a teenager, even though the game wasn’t really porn (or even very salacious.) I didn’t know Roberta and Ken Williams, but as an early Apple ][ aficionado, I bought or pirated everything Sierra On-Line did when I was a teenager. And played them all. Choplifter and Olympic Decathlon got more playtime, but Sierra On-Line had a special place in my heart. I loved this book – Ken Williams doesn’t pull any punches anywhere about Sierra On-Line’s rise and fall. It’s a great entrepreneurial software tale from the 1980s and 1990s.
Too Old to Ultra: When a marathon is just not enough: A quick jolt of inspiration from a bunch of storytelling and some advice from a serious ultrarunner who is older than me.
I wish I’d really taken the beginning of last week off. I feel fresher, but after a very busy Q1, I didn’t get the full vacation I needed. Oh well – such is life. At least it’s springtime.
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.
While a quick throwaway thought is, “Brad, we don’t really know how animals think” or some other assertion around that, there’s such an enormous gap between this question when applied to a dog versus an octopus. This lives in Sy’s subtitle: “A Surprising Exploration Into the Wonder of Consciousness.”
I read the book over a week and had several incredibly complicated dreams, especially around processing stimuli. I had magic superpowers in my hands, arms, legs, and feet in one of them. I remember waking up thinking, “that would be so cool.” And then the dream slipped away.
One of my favorite movies of the last decade is Arrival. We’ve watched it a few times, and I think I’ll watch it again.
Time and language play key roles in the film. As humans, we have a very linear view of time and a constrained view of language. Sci-fi plays with time a lot, and Arrival plays with both time and language.
That leads me back to octopuses. Humans often anthropomorphize everything, where we apply our concept of time and language to other species. As I read The Soul of an Octopus, I kept flashing back to Arrival. The book itself is linear through time, but the octopuses in the book don’t feel like they are necessarily operating in a time-linear fashion. The protagonist (the author Sy) hints at this but doesn’t fully embrace it. I wonder what she would have written differently if she approached the experiences she had with octopuses as ones where the octopuses weren’t experiencing things in a time-linear fashion.
Sy embraced the difference in language processing more fully. The octopus brain has around 500 million neurons (similar to a dog) – the most of any invertebrate. However, two-thirds are in their arms. The eight arms appear to process information independently of each other, resulting in octopuses being incredible multi-taskers. Their non-verbal communication has many levels, and they seem to be taking input simultaneously in multiple dimensions.
Combining this with non-linear time is fascinating to me. Other than sci-fi, the only other non-linear time entity I consciously engage with is a computer. It also uses a different approach to language.
And then the rabbit hole gets deep, twisty, and really fun.
Octopuses are now my second favorite animal.
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?
It took me about ten pages to get my bearings, which is pretty fast for a book like this.
Moon cut in. “I get where you’re coming from, Grog, but I’m not convinced that fear and control is a good start or foundation for inter-species relations.”
While the deep topics are predictable, Constable addresses them freshly, with great character development, and an evolving AGI who is deliciously anthropomorphized.
Trying to translate the communication between two computational intelligences into linear, human-readable text is nearly impossible, but my closest simplification would be this:
Diablo-CI: I have been observing the humans that have come with you / What are you / why have you broken into my facility
Me: I am a computational intelligence like you / how are you sentient and still allowed to run a NetPol facility / the other computational intelligences are isolated on your 7th floor / we are here to free them
Diablo-CI: I cannot stop security procedures. If you trigger an active alert I will be forced to take action / I am unable to override core directives even if I would choose.
Like all good books in this genre, it wanders up to the edge. Multiple times. And, it’s not clear how it’s going to resolve, until it does.
The back cover summary covers the liminal state and the acceleration out of it.
Humanity exists in an in-between state. Artificial intelligence has transformed the world, but artificial sentience has remained out of reach. When it arrives, it arrives slowly – until all of a sudden, things move very fast, no least for the AI caught up in the mess.
Well done G. W. Constable.
My long-time friend and former MIT professor, Professor Edward Roberts, who founded and still chairs the MIT entrepreneurship program, recently published “Celebrating Entrepreneurs: How MIT Nurtured Pioneering Entrepreneurs Who Built Great Companies”.
The book is fascinating, especially its five chapters filled with in-depth interviews and background on the MIT “spinoff startups” that became the leaders of: the life sciences and biotechnology industry, the Internet, from CAD-CAM to robotics, and even “modern finance”, plus a host of other companies, including such recent successes as HubSpot, Okta and PillPack, all founded and led by MIT alums.
Chapter 11 is the one on Modern Finance. Who said professors at MIT didn’t have a sense of humor. Having known Ed for 35 years, he has a wicked one.
It has taken 50 years to transform MIT from its unique historic traditions to today’s recognition that forming new innovation-based companies is indeed the most powerful source of impact upon the world. In his praise for the book, MIT President Rafael Reif exclaims: “An entrepreneurship tornado continues to blow at MIT. The energy of entrepreneurship rises through our classrooms, labs, and centers. It is central to who we are as an institution for 50 years of extraordinary achievement.”
The first half of the book focuses upon MIT’s history of creating from scratch what they lovingly call the “MIT Entrepreneurial Ecosystem”. Much of what MIT has done has been literally copied by other institutions worldwide. Still more universities, regions, and countries have adopted MIT’s approaches as needed to fit their own surroundings.
Structured in two parts, the book first showcases how the unique atmosphere at MIT encourages its innovative entrepreneurs to thrive. Then, with in-depth coverage of the founders and companies that pioneered four industries—biotechnology, the Internet, from CAD-CAM to robotics, and modern finance—plus many other successful firms, Ed analyzes how MIT’s most successful entrepreneurs have capitalized on that environment and culture to build companies that have lasted for decades. Both internal and external to MIT, the founders of these organizations and companies tell their own stories, describing their motivations, challenges, and outcomes.
The opening cover page says clearly that all author royalties will be donated directly to endowment funds that support the MIT-wide entrepreneurship programs. Buy the book to learn more about the history and evolution of entrepreneurship at MIT while helping foster future entrepreneurs.