Category: Books
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.
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!
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:
- Too Much Focus on Things, Not Enough Focus on Commitment
- Too Many Twenty-First-Century Values, Not Enough Eighteenth-Century Values
- Too Much “Success,” Not Enough Character
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.
My newest book, The Entrepreneur’s Weekly Nietzsche: A Book for Disruptors, shipped today. It’s available on Amazon in Kindle, Paperback, and Hardcover. If you are so inclined, go buy a copy today!
I’m particularly proud of this book, as it is a more philosophical approach to entrepreneurship than my other books. I wrote it with Dave Jilk, the co-founder of our first company (Feld Technologies, 1987) and one of my closest friends for 38 years.
The book contains 52 individual chapters (hence the “Weekly” in the title) and is divided into five major sections (Strategy, Culture, Free Spirits, Leadership, and Tactics). Each chapter begins with a quote from one of Nietzsche’s works, using a public domain translation, followed by our own adaptation of the quote to 21st-century English. Next is a brief essay applying the quote to entrepreneurship. About two-thirds of the chapters include a narrative by or about an entrepreneur we know (or know of), telling a concrete story from their personal experience as it applies to the quote, the essay, or both.
Our goal with this book is to make you think, rather than try to tell you the answers. For example, here’s the Nietzsche quote from a chapter titled “Obsession” from the section on “Free Spirits”.
“The passion which seizes the noble man is a peculiarity, without his knowing that it is so: the use of a rare and singular measuring-rod, almost a frenzy: the feeling of heat in things that feel cold to all other persons: a divining of values for which scales have not yet been invented: a sacrificing on altars which are consecrated to an unknown God: a bravery without the desire for honor: a self-sufficiency which has superabundance: and imparts to men and things.”
Our interpretation is:
In other words: A noble man has exceptional passion, but does not realize just how unusual it is: he has high standards for success, enthusiasm for things that others find dull, a sense of what will be valuable in the future, intense but unexplained motivations, courage without the need for praise, and the ability to sustain and revel in this intensity without support from others.
And the chapter begins with:
You may have noticed that this chapter is titled Obsession, but Nietzsche seems to be talking about passion. For several years, Brad has written and spoken about the pitfalls of “passion” in entrepreneurs, distinguishing it from “obsession,” which is a quality he looks for. Dictionaries generally speak of passion as a strong emotion, while obsession is a preoccupation of the mind. We have a hunch that Nietzsche is trying to make a similar distinction here. The word “obsession” did not come into common use until later. Earlier in the text, he says, “What then makes a person ‘noble’?…Certainly not that he generally follows his passions; there are contemptible passions.” It is worth asking yourself whether you are obsessed with your business and the problem it solves for customers or merely passionate about it.
If you intend to disrupt an industry or change the world, you must expect people to see you as crazy, intransigent, and possibly sociopathic. Maybe you are. To sustain yourself and your efforts in such a climate, you must find your drive within. You must know your vision and why it matters to you. Importantly, you cannot feel that its correctness depends on your ability to explain it to others. You must be obsessed.
Each essay from us is two to three pages long, so they are easy to quickly consume and then reflect on. The narratives from entrepreneurs telling their story as it applies to the quote are also a few pages long.
For one more taste, here’s the Nietzsche quote and our interpretation chapter called “Attracting Followers” from the chapter on “Leadership”.
“Men press forward to the light not in order to see better but to shine better.—The person before whom we shine we gladly allow to be called a light.”
In other words: People are drawn to light because it shines on them, not because it shows them the way. A person who makes us shine is someone we gladly call a light.”
I hope this inspires you to get a copy of The Entrepreneur’s Weekly Nietzsche: A Book for Disruptors. I’d love to hear what you think about it.
My newest book, The Entrepreneur’s Weekly Nietzsche: A Book for Disruptors, comes out next Tuesday, May 25th.
This has been an on-again, off-again project with Dave Jilk that began in 2013. We were spending the weekend in Keystone with our wives (Amy and Maureen), which generally involved a lot of sitting around reading. Dave was reading On Nietzsche by Eric Steinhart. He read a quote to me and asked if I thought it sounded like an entrepreneur. Dave remembers me saying, “Hmmm, it sure does.” Then we both went back to our books.
At the time, I knew nothing about Nietzsche. Actually, I knew less than nothing since everything I knew about him was wrong.
Dave is one of my best friends. We met over 38 years ago, on my first day at MIT, right after the freshman picnic, when I ended up in a van that took me to ADP, the fraternity I ended up joining and living at for four years. Dave was a senior, and we became best friends. We started a company that year with Sameer Gandhi and Andy Mina called Martingale Software that failed pretty quickly. Several years later, we started Feld Technologies, which we ran together from 1987 to 1993 when we sold it to Sage Alerting Systems, which later renamed itself to AmeriData Technologies. We kept working together – him as an entrepreneur, me as an investor.
But “business” is only a small part of our relationship. For any close friendship that lasts 38 years, he has a better understanding of me than almost anyone else on this planet (Amy has him beat.) So, theoretically, he knew what he was getting into when we decided to start writing a book together. I expect there was a moment, though, where he shouted at the top of his lungs, “Brad, enough with the fucking commas.”
We made progress in fits and starts. Most of the fits were a result of me getting distracted by something else. Sometimes it was work. Sometimes it was another book that got in the way. Sometimes it was burnout – writing, work, or just general lassitude. Dave hung in there each time, giving me space, moving things forward without me, and then when I resurfaced, quickly kicking back into gear on his end to respond to whatever I was doing.
I’ll write plenty more about the book, Nietzsche, and why we think Nietzsche is so relevant to entrepreneurs, but I want to end with two paragraphs of appreciate for people.
The first is Ryan Holiday, who was an inspiration for me with his book The Daily Stoic. I read a page almost every day. Ryan inspires me at so many levels, but his ability to make stoicism accessible to entrepreneurs has been magical and transformative for many people I know, including me. I’m hopeful Dave and I can emulate even a tiny bit of what Ryan has accomplished, but this time with Nietzsche.
The second is Reid Hoffman. He agreed to write the foreword several years ago when I first told him about this project. He waited patiently, and he produced a brilliant foreword that captures the essence of what we’ve tried to do with the book. In addition, as a bonus, he used Nietzsche’s writing style for some of it. Reid is a great human, and I deeply appreciate his involvement in this project.
I’ve been reading hard science fiction lately, along with some actual science. The hard sci-fi includes Dragon’s Egg and Starquake by Robert Forward (wow – awesome) and Nova by Samuel Delany (also awesome). The science includes The God Equation: The Quest for a Theory of Everything by Michio Kaku and Fundamentals: Ten Keys to Reality by Frank Wilczek.
In between runs this weekend I finished Nova (I was listening to it on Audible), Fundamentals (I was reading it on Kindle), and read most of Starquake (It’s only available in physical form.) I also started listening to Project Hail Mary by Andy Weir. The only thing that would have made this weekend better would be a third day to it, instead of the Monday in front of me.
Frank Wilczek is a legendary physicist who won the Nobel Prize in 2004 for “for the discovery of asymptotic freedom in the theory of the strong interaction.” with David Gross and David Politzer. His office at MIT is in the same hallway as Bernard Feld, my MIT namesake (Prof B. Feld, something I never became.) He also happens to be a spectacular writer.
Fundamentals is extremely accessible. After reading Michio Kaku’s The God Equation, I realized that I knew a lot of surface-level physics (and science in general), but there was a layer down, especially from the past 20 years, that was elusive. Kaku’s presented it in a way that one could understand without any deep quantum physics knowledge, so I went looking for more.
Wilczek delivered. The first part of the book, called “What There Is”, has five chapters.
- There’s Plenty of Space
- There’s Plenty of Time
- There Are Very Few Ingredients
- There Are Very Few Laws
- There’s Plenty of Matter and Energy
It’s brilliant.
As I read hard sci-fi, the entanglement of known science at the time (Nova was published in 1968; The Dragon’s Egg was published in 1980) along with speculation of where things were going (e.g. each book took place far in the future) created a contextual backdrop for me for Fundamentals that helped bring what we know, and what we don’t know, to the surface. Or, more specifically, what we knew (in 1968, 1980) that was right, and what doesn’t seem right anymore because it wasn’t known, or understood.
The shocker is how much is directionally correct. When I read Asimov from the 1950s (I, Robot is a good place to start), or Philip K. Dick from the 1960s (Do Androids Dream of Electric Sheep is a good place to start) I have the same feeling. Many details are completely wrong (e.g. how data is stored on auxtape) but others are completely correct (e.g. massive underground data centers). Hard sci-fi takes more risks on this dimension, and both Forward and Delany do an amazing job of both the science and the storytelling.
In the last 20 years, I’ve read a lot more sci-fi than science. That’s a miss on my part. Going forward, my diet will include both. And I hope to someday meet a Cheela. And a Shrike.
My partner Seth Levine and his co-author Elizabeth MacBride recently wrote an important book called The New Builders: Face to Face with the True Future of Business. It is out and available.
Foundry Group is hosting an open virtual event to discuss the book. Seth and Elizabeth will be moderating the discussion with special guests Colorado Senator John Hickenlooper, Makisha Boothe of Sistahbiz, Colorado Congressman Joe Neguse, and Lorena Cantarovici of Maria Empanada.
Sign up here for the virtual event at May 18, 2021 12:00 PM PT; 1:00 PM MT.
Seth and Elizabeth have spent the past year talking to entrepreneurs all over the United States as they’ve developed their thesis around The New Builders. The Covid crisis has accelerated the growth and development of many high-tech companies, including the largest companies that were recently young, entrepreneurial businesses. But, unfortunately, the Covid crisis has decimated many local businesses and dramatically impacted communities everywhere.
The New Builders are the future of business that will emerge from the Covid crisis, and the book argues for the future of American entrepreneurship. That future lies in surprising places and will rely on the success of women, Black, and Brown entrepreneurs. However, our country hasn’t yet recognized the New Builders’ identities, let alone developed strategies to support them.
Join the conversation about The New Builders with Seth, Elizabeth, John, Makisha, Joe, and Lorena on May 18th.
My long-time business partner Seth Levine has written a book with Elizabeth MacBride titled The New Builders: Face to Face with the TRUE Future of Business. It’s extraordinary – buy a copy now!
For many years, Seth has been frustrated about the entrepreneurial narrative around the White male tech founder. He’s been active as an investor and philanthropist around entrepreneurship in rural Colorado and with organizations, such as Entrepreneurship for All, that are focused on accelerating economic and social impact in communities nationwide through inclusive entrepreneurship. He’s been exploring this and investing both in the US and other places globally, including Africa and the Middle East.
Pre-Covid, he started working on The New Builders with Elizabeth MacBride. They made good progress, and I remember saying hello to Elizabeth in our conference room after she and Seth had taken it over for a few days of writing, back when we met in conference rooms. As the Covid crisis began, they started writing a series of OpEds that got a lot of play, including To save the US economy, policymakers need to understand small business 101, and Communities across America rush to save Main Street as federal relief for small business stalls. These articles foreshadowed what they were digging into as part of their research for The New Builders.
Seth and Elizabeth obliterate the myth of the White male tech founder. Through detailed history, current stories, and many interviews, they bring life to new businesses started by Black, Brown, Female, and Older people. These entrepreneurs, including immigrants, are the next generation of business owners. Post-Covid, they will be key to redefining our economy.
While this group of founders and business owners may not get the same press that tech entrepreneurs get, they profoundly impact their local communities. Their efforts are foundational to the health, development, and growth of American cities, enabling a future where people have the economic freedom to pursue their passions.
Seth and Elizabeth have issued a powerful wake-up call for America with The New Builders. It’s time to see, understand, and value the next generation of business owners.
Book: LEVERS – The Framework For Building Repeatability into Your Business
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.
- Create clarity and alignment across the leadership team and the entire organization
- Provide a straightforward way to communicate to all stakeholders
- Give the leadership team more control over the destiny of the company
- Explain a clear and data-driven plan on how to build a long-term and sustainable business
I highly recommend getting your copy of LEVERS – The Framework For Building Repeatability into Your Business today.
On my run to Boulder on Saturday, I listened to The God Equation: The Quest for a Theory of Everything by theoretical physicist Michio Kaku. My run was about four hours long, which was roughly the time it took to listen to this spectacular book. The quick summary from Wikipedia follows:
Kaku explores the history of unification theories of Physics starting with Newton’s law of universal gravitation which unified our experience of gravity on Earth and the motions of the celestial bodies to Einstein’s general relativity and quantum mechanics and the Standard Model. Kaku dubs the final Grand Unified Theory of relativity and quantum gravity The God Equation with an 11-dimensional String theory as the only self-consistent theory that seems to fit the bill.
I knew a bunch of the history Kaku covered, but he did it in a clear and beautiful way that built up to a bunch of contemporary theory that I couldn’t have explained prior to listening to the book. M-theory is still a complete mystery to me, but at least I understand the linkage to Trisolarans and their sophons a little better.
This morning, I had an email from Tom Keller pointing at a recent APOD from 4/16/21. It was additive to my experience running on 4/17 and listening to Kaku’s book.
Explanation: Light rays from accretion disks around a pair of orbiting supermassive black holes make their way through the warped space-time produced by extreme gravity in this stunning computer visualization. The simulated accretion disks have been given different false color schemes, red for the disk surrounding a 200-million-solar-mass black hole, and blue for the disk surrounding a 100-million-solar-mass black hole. That makes it easier to track the light sources, but the choice also reflects reality. Hotter gas gives off light closer to the blue end of the spectrum and material orbiting smaller black holes experiences stronger gravitational effects that produce higher temperatures. For these masses, both accretion disks would actually emit most of their light in the ultraviolet though. In the video, distorted secondary images of the blue black hole, which show the red black hole’s view of its partner, can be found within the tangled skein of the red disk warped by the gravity of the blue black hole in the foreground. Because we’re seeing red’s view of blue while also seeing blue directly, the images allow us to see both sides of blue at the same time. Red and blue light originating from both black holes can be seen in the innermost ring of light, called the photon ring, near their event horizons. Astronomers expect that in the not-too-distant future they’ll be able to detect gravitational waves, ripples in space-time, produced when two supermassive black holes in a system much like the one simulated here spiral together and merge.
You know nothing Jon Snow.