The public face of a startup CEO can seem pretty glamorous – dramatic product announcements, exciting travel, and speaking appearances, leading a team as it grows and takes steps to fulfill its mission.

What you don't see is what a CEO does on a regular basis, day after day after day. Nobody imagines Google CEO Larry Page working out the mechanics of the option pool or the global sales team's reporting structure and The Social Network certainly didn't include a montage of Mark Zuckerberg interviewing potential executives about the finer points of operating leverage. Nonetheless, these are the types of things that CEOs spend the vast majority of their time doing (as more than a couple of once‐eager entrepreneurs have learned, to their dismay). One startup CEO I know who has made those realities central to his public persona is Return Path's CEO, Matt Blumberg.

I've had the pleasure of working with Matt for many years. He was on my board of directors at FeedBurner before the Google acquisition in 2007 and he's been a valuable colleague and adviser ever since.

For nearly a decade, Matt has documented every element of the startup CEO experience. The product launches and mergers and acquisitions are all there – but so are the vacation policies, the meeting routines, the forecasting models, and the best practices for recruiting talent. They're not as glamorous as the Next Big Thing, but they're the key to every startup's success.

When he launched Return Path in 1999, Matt started with this simple idea: an “email change of address” database that would do for the digital world what the post office's “change of address” service does for snail mail. He and his team expanded their focus to a much wider set of email‐related problems: building distribution lists, conducting online customer surveys, and so on. As markets shifted, Matt narrowed the company's focus to “email deliverability.” As that business grew ever more successful, Return Path has set its larger sights on “email intelligence,” solving domain‐related problems like spoofing, phishing, and competitive tracking.

As a four‐time CEO (currently at Twitter), I can say this with a relative degree of certainty: most companies don't survive that many changes in direction over that many years. Return Path, by contrast, has survived and thrived: they have 400 employees around the world and they're closing in on $100 million in revenue. How did they do it? By focusing on all the unglamorous bits and building a company resilient enough to weather major pivots, the occasional divestiture, and (most recently) a global economic crisis.

Matt's experience proves that the hard work of building a company is far more important than the excitement of coming up with “The Idea.” Until this book, I have yet to see anybody lay out all the details of this extremely difficult and unique job. He started the process on his blog, Only Once, and he brings it to fruition in this wonderful book. Read it and you will get a master class in building companies from someone who's honed that skill for more than a decade.

Dick Costolo
CEO of Twitter
April 2013

The list of people to thank for their role in the development of this book is long but it has to start with my long‐time board member and friend, Brad Feld. Brad and I started our respective blogs, Feld Thoughts (www.feld.com) and Only Once (www.onlyonceblog.com) on the same day – May 10, 2004 – sitting next to each other in our shared office space in Superior, Colorado, and trying to figure out how to use Typepad templates. Brad has been a great friend and valuable business partner for more than a decade now. When Brad started writing books with John Wiley & Sons as his publisher, we had a conversation about my someday writing a book inspired by the content of my blog. I was one of the many contributors to his first book, Do More Faster: Techstars Lessons to Accelerate Your Startup; then when he asked me to read a draft of his second book, Venture Deals: Be Smarter Than Your Lawyer or Your Venture Capitalist, I returned the manuscript with a markup that became a series of about 40 or 50 sidebars called “The Entrepreneur's Perspective.” Brad got good feedback on those contributions from many of his readers and introduced me to his publishing team at Wiley about this book, and the rest is history. Brad offered a number of valuable insights on this book as well as helping me navigate the publishing process along the way, and he did so a second time for this second edition.

I would like to acknowledge the rest of our board as well for their contributions to my education as a CEO over the years as well as their specific contributions to this book. Fred Wilson, Greg Sands, Scott Weiss, Scott Petry, and Jeff Epstein all played a significant role as long‐term directors in my day‐to‐day life as CEO. Other Return Path board members over the years certainly added to my education as a CEO and deserve thanks as well, including Ben Perez, Bob Knapp, Jonathan Shapiro, Eric Kirby, Phil Summe, Chris Wand, Chris Hoerenz, James Marciano, and Pat Severson. The CEOs of the organizations on whose boards I've sat as a director or chairman, Dick Costolo, Jim Follett, Rand Fishkin, Sarah Bird, Tami Forman, Larry Kimmel, and Linda Woolley, have also significantly informed my experience as CEO by giving me a closer‐than‐average look at how other CEOs operate.

This book would also not exist without my team at Return Path, who challenged, inspired, and taught me things every day. When I say team, I mean all 1300 colleagues who have ever worked at Return Path. I want to specifically acknowledge my long‐time executive assistant, Andrea Ponchione, and long‐term executive partners, George Bilbrey, Jack Sinclair, Anita Absey, Angela Baldonero, Ken Takahashi, Andy Sautins, Dave Wilby, Shawn Nussbaum, Cathy Hawley, Tom Bartel; and other executive team members, Wes Antrobus, Nick Badgett, Theo Noel, Michelle Pelletier, Tammy Shimp, Scott Ziegler, Louis Bucciarelli, Daniel Incandela, and Tami Forman. Extra thanks to George for lots of specific help on the book, especially on Part One.

This book would also not be possible without a few other people who have helped teach me my job along the way. Marc Maltz from Hoola Hoop has been one of my secret weapons as my executive coach. Members of my CEO Forum over the years have been unbelievably helpful: Adam Slutsky, Alan Masarek, Jonathan Zabusky, Clare Hart, Chad Dickerson, Cella Irvine (who sadly passed away between the publication of the first and second editions of the book), Jonathan Shapiro, and David Kidder (David's book, Startup Playbook, was researched and written as this book got under way – there are lots of synergies between the two, though they're quite different). The other senior leaders I've worked with at prior jobs, Andrew Jarecki, Bill Ford, Neal Pomroy, Eleanor Leger, and Mike Sargent, all helped me get where I am in business and influenced the way I manage and lead Return Path.

I want to thank the teams at Wiley and Techstars Press, Bill Falloon, Meg Freeborn, Pete Birkeland, and Rachel Meier, for their thoughtful feedback and editorial support. This book would also not be possible without the efforts of Hanny Hindi, who was the first edition's project manager, the curator of content I'd already written on my blog and my occasional ghost writer and editor. There's no chance I could have cranked out this many words on my own while running a company! Special thanks as well to Clare Tischer from Techstars, who volunteered to do a hardcore copy edit of the first edition for us, just because she liked the topic and wanted to help make the end product great when I didn't think I could possibly edit my own work effectively one more time.

I want to end by thanking my family for their insights and feedback about this book and their patience while I was doing double duty to write it and still do my day job. I owe the ultimate debt of gratitude to my parents, Bob and Joyce, for teaching me most of the life lessons I learned – all of which shape how I manage and lead – and to my dad, a fellow CEO, for a few additional content‐specific lessons related to this book's topic. My kids, Casey, Wilson, and Elyse, who didn't exist when I started the company, have been increasingly aware of the business as they've gotten older and were there to support me at the emotional time that came with the eventual sale of the company. Finally, I'm not sure I'd be nearly as successful of a CEO or grounded a person as I have been without Mariquita, the love of my life and my best and most reliable sounding board throughout the life of the business.

Matt Blumberg founded Return Path in 1999 because he believed the world needed email to work better and because he wanted to build a model workplace for the knowledge economy. Matt‘s passion about enhancing the online relationship between email subscribers and marketers so that both sides of the equation benefit was part of the formula that drove Return Path from an initial concept to a profitable company of almost 500 employees worldwide with $100mm in revenues and ultimately to its successful exit in a strategic sale to Validity in 2019.

After leaving Validity, Matt ended up doing a couple of Interim CEO stints, including one particularly interesting one starting up an organization for the State of Colorado called the Innovation Response Team. The role as leader of the Response Team required rapid‐response creative programs that were entrepreneurial, out‐of‐the‐box thinking. It also required deep connections to the private sector (as well as cross‐agency collaboration within various levels of government), integrated with the state's Emergency Operations Center. The impact as an interim leader of these two organizations led Matt and a group of former Return Path colleagues to start a new company called Bolster. In partnership with High Alpha and Silicon Valley Bank, Bolster is a talent marketplace that matches companies and executives on an interim, fractional, advisory, and project basis. Think of Bolster as “NetJets for senior executives.”

Along with the Bolster team and a few former Return Path executives, Matt is working on another book, Startup CXO: A Field Guide to Scaling Up Your Company's Critical Functions and Teams. They share their collective wisdom of how to build and scale the different functions inside a successful high‐growth company.

Startup CEO is not a book about how to start a company or find early‐stage financing. While these topics are essential to entrepreneurship, they're well covered elsewhere. This book is also not about sales, marketing, engineering, finance, or other disciplines inside the company. It's not the story of my company, Return Path, though there are a lot of examples from Return Path in it. It's not my blog, Only Once (www.onlyonceblog.com), though my blog posts inspired bits and pieces of the material in this book and I still continue to write it.

I set out here to write the book I wish someone had given me on my first day of work as CEO of Return Path over 20 years ago. There is no instruction manual, no field guide, to being a CEO. If you become the CEO of General Electric or General Motors, you have been groomed for the job for decades. If you're starting your own company – and have never done it before – you don't have the luxury of that level of grooming. I believed I had as good experience as I possibly could have when I started Return Path at the age of 29. Management consulting. Venture capital. General manager of an Internet startup within a larger company, working for a CEO. Then I got into the job and realized that I didn't have a clue what I was doing.

There is a real craft to being a CEO and leading a full organization and there's no substitute for actually being in the job, especially early in your career. I've written a blog called Only Once since May 10, 2004, and I cover a few different topics but it is primarily devoted to posts about entrepreneurship, leadership, and management. My long‐time friend and board member, Fred Wilson, inspired the name of the blog with a post entitled “You're Only a First‐Time CEO Once.” In that post, he says:

The hardest job in management is the “first time CEO.” I have absolutely no data on this, but I suspect that at least 75% of firsttime CEOs fail at some level. Many get fired. Many go down with the ship when it sinks. Some quit. Many sell their businesses before they've realized their full potential because they just can't figure out how to do the job right.

But in venture capitalism, among the most pure forms of capitalism there is, failure isn't all bad. Because, as I said yesterday, “you are only a first time CEO once.” Most talented business people come up the learning curve quickly. And the next time, they don't make the same mistakes. They move faster. They listen better. They spend less. They hire better. The list goes on and on.

So, what does this mean for VCs? It means back serial entrepreneurs who have done it before. But if you can't do that, and are backing a first‐time CEO, recognize the risks of that. Mentor, coach, and pay a lot more attention.

What does this mean for entrepreneurs and managers? It means that the first time you run a business, you should admit what you are up against. Don't let ego get in the way. Ask for help from your board and get coaching and mentoring. And recognize that you may fail at some level. And don't let the fear of failure get in the way. Because failure isn't fatal. It may well be a required rite of passage.

As a CEO, I feel like I've made every mistake in the book at least once. I'm sure I've made a couple more than once. So this book is my hope to pay forward the lessons of my 20 years of experience as a first‐time CEO to other entrepreneurs, whether actual or aspiring. If I can help just one of them not get fired, not go down with the ship, not quit, and figure out how to do the job, then I will call this book a success.

Let me issue three caveats before I begin. The first is that this book is based on my experience and the experience of a handful of other CEOs whom I know well. For the most part, that means American CEOs running U.S.‐based companies, in and around the Internet sector, that got started between 1990 and 2010 and with fewer than 500 employees. I hope the book proves to be timeless and that it spans cultural and industry boundaries, but there will be some inherent limitations based on my own experience. I've tried to broaden that in asking a number of people to contribute sidebars, section openers, and section conclusions in this book, but that group of contributors is still largely made up of people generally like me.

The second caveat is that I don't have a single clever tagline or overarching premise that's going to answer all questions and challenges associated with the job. Being a CEO is an incredibly complex job at a company of any size and writing a book called Be Authentic or something like that wouldn't do it justice. That's why this book is designed more as a practical field guide than a lofty book on philosophy.

The third caveat is that I don't have all of the answers and I haven't figured everything out. The trouble is that no one else has, either. I have, however, figured out many of the questions to ask as well as the answers that come from my own experience. Running a company is situational. You can be a great CEO and miss the occasional curve ball that comes your way. This is my best shot at documenting what I've learned over the years in the job.

Being a CEO is also somewhat personal in nature. Because something works for me doesn't mean it will work for someone else. Each and every leader has a different style, different values and beliefs, and a different approach to the world. My intent here isn't to produce value judgments of “this is the only way to do XYZ task” so much as it is to document most of the primary jobs of a CEO in a company from the startup stage (fewer than 25 employees), through the revenue stage (fewer than 150 employees), and into the growth stage (fewer than 500 employees) and give some examples from my own experience of one or two ways of approaching each task.

Coming up with a framework for this book was challenging. I drew once again from one of Fred's blog posts, entitled “What a CEO Does,” where he quotes another experienced colleague of his from the venture business:

A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank.

I like the simplicity of that framework and I've adapted it somewhat into the outline of this book. Part One of the book focuses on the ideal way to communicate your vision: “Storytelling.” Part Two is entitled “Building the Company's Human Capital.” The outline got a bit beyond Fred's framework. While I generally agree that those three things are critical, it's impossible not to add a few other important topics to the list. First, I think you have to broaden the third topic. It's not just about making sure there's enough cash in the bank. It's about execution in general, so Part Three of this book is called “Execution” – both about having the money in the bank and about using it wisely through disciplined execution. Part Four covers a very unique aspect of the CEO's job: “Building and Leading a Board of Directors.” Part Five is more about the how of doing the job as opposed to the what: “Managing Yourself So You Can Manage Others.”

I want to emphasize here that even though “Managing Yourself” is addressed in Part Five, you shouldn't wait to implement the practices and tips I outline until after you have gotten traction in your business model. By then it will be too late and all your time (and your sanity!) will be absorbed by the business. It's vitally important to build your business in ways that keep you refreshed, energized, and operating at peak personal performance. Part Five contains the tricks I have learned and the tools I use to bring the best of myself to both work activities and relationships outside of work, every day. Part Six, new in the second edition, speaks to the process of preparing for, executing, and recovering from, the sale of the company.

This framework encompasses nearly every challenge a startup CEO has to face but it leaves out one crucial area: management and leadership.

As a manager and a leader, I had a number of positive influence points over the course of my career and a number of negative influence points. I vowed to learn from those, both the good and the bad, and bring them with me to my job as CEO. In particular, some incredibly poor management practices I'd seen over the years motivated me to create a different kind of workplace.

Sometime after a few years running the business, I took a different approach. I didn't pause when making tough decisions to consider what others would do if they were in my place. I started developing my own reflexes, my own instincts, and my own way of talking through things.

I can't remember what the turning point was in finding my voice as a CEO. It might have come out of some specific critical incident. It might have come from working with my coach. It might have just emerged slowly, without a turning point, as I spent more time maturing in the role. From the rearview mirror, I wish I had done more, earlier, to help me find my voice. Mostly, I wish I'd been deliberate about finding it; that certainly would have hastened the discovery!

Throughout this book, I'll introduce some of the management and leadership principles I've developed as a CEO in a feature called “Management Moment.” Think about what you agree with, where you're different, and what's missing that's important to you. I promise that both you and your organization will benefit from your strength and confidence as a leader.

Postscript for the second edition: When we sold Return Path in May of 2019, we were just a few months shy of our 20th anniversary. I learned a lot of new lessons in the seven years between writing the first edition of Startup CEO and today. I had three objectives in writing a second edition:

• Completing a brief “cleanup” of the first edition to make sure it feels as contemporary as possible, as a number of small things have changed since the original manuscript. Seven years is a lifetime in terms of changes to micro‐trends, language, business in general, and the world around us.
• Adding some topics that reflect heightened responsibilities of CEOs around moral and ethical leadership in an increasingly transparent and socially conscious world. Whether it's the #metoo movement, high‐profile failures of leadership like airline employees dragging customers off of planes, or something as simple as unconscious bias in the workplace, the best CEOs now need to approach their jobs differently.
• Adding a new section around selling a business. Startup exits are the important culmination of the startup experience and something that the first edition only briefly touched on.

The first edition of the book has sold something like 35,000 copies as of the writing of the second edition, which blew me away when I tallied it all up. I've received many notes of thanks from readers all over the world for the book, and I'm glad that the content has proved useful to so many people, noting from some of the more critical reviews on Amazon that it certainly doesn't scratch everyone's itch. I hope the changes in the new edition add even more value to the lives of entrepreneurs and startup management teams. That's really who the book is written for.