I’ve published two editions of Startup CEO, a sequel called Startup CXO, and am a co-author on the second edition of Startup Boards. We also just (2025) published mini-book versions of Startup CXO specifically for five individual functions, Startup CFO, Startup CRO, Startup CMO, Startup CPO, and Startup CTO.

You’re only a startup CEO once. Do it well with Startup CEO, a “master class in building a business.”

—Dick Costolo, Partner at 01A (Former CEO, Twitter)

Being a startup CEO is a job like no other: it’s difficult, risky, stressful, lonely, and often learned through trial and error. As a startup CEO seeing things for the first time, you’re likely to make mistakes, fail, get things wrong, and feel like you don’t have any control over outcomes.

As a Startup CEO myself, I share my experience, mistakes, and lessons learned as I guided Return Path from a handful of employees and no revenues to over $100 million in revenues and 500 employees.

Startup CEO is not a memoir of Return Path’s 20-year journey but a CEO-focused book that provides first-time CEOs with advice, tools, and approaches for the situations that startup CEOs will face.

You’ll learn:

How to tell your story to new hires, investors, and customers for greater alignment How to create a values-based culture for speed and engagement How to create business and personal operating systems so that you can balance your life and grow your company at the same time How to develop, lead, and leverage your board of directors for greater impact How to ensure that your company is bought, not sold, when you exit

Startup CEO is the field guide every CEO needs throughout the growth of their company and the one I wish I had.

“Startup CXO is an amazing resource for CEOs but also for functional leaders and professionals at any stage of their career.”

– Scott Dorsey, Managing Partner, High Alpha (Former CEO, ExactTarget)

One of the greatest challenges for startup teams is scaling because usually there’s not a blueprint to follow, people are learning their function as they go, and everyone is wearing multiple hats. There can be lots of trial and error, lots of missteps, and lots of valuable time and money squandered as companies scale. My team and I understand the scaling challenges—we’ve been there, and it took us nearly 20 years to scale and achieve a successful exit. Along the way we learned what worked and what didn’t work, and we share these lessons learned in Startup CXO.

Unlike other business books, Startup CXO is designed to help each functional leader understand how their function scales, what to anticipate as they scale, and what things to avoid. Beyond providing function-specific advice, tools, and tactics, Startup CXO is a resource for each team member to learn about the other functions, understand other functional challenges, and get greater clarity on how to collaborate effectively with the other functional leads.

CEOs, Board members, and investors have a book they can consult to pinpoint areas of weakness and learn how to turn those into strengths. Startup CXO has in-depth chapters covering the nine most common functions in startups: finance, people, marketing, sales, customers, business development, product, operations, and privacy. Each functional section has a “CEO to CEO Advice” summary from me on what great looks like for that CXO, signs your CXO isn’t scaling, and how to engage with your CXO.

Startup CXO also has a section on the future of executive work, fractional and interim roles. Written by leading practitioners in the newly emergent fractional executive world, each function is covered with useful tips on how to be a successful fractional executive as well as what to look for and how to manage fractional executives.

A comprehensive guide on creating, growing, and leveraging a board of directors written for CEOs, board members, and people seeking board roles.

The first time many founders see the inside of a board room is when they step in to lead their board. But how do boards work? How should they be structured, managed, and leveraged so that startups can grow, avoid pitfalls, and get the best out of their boards? Authors Brad Feld, Mahendra Ramsinghani, and Matt Blumberg have collectively served on hundreds of startup and scaleup boards over the past 30 years, attended thousands of board meetings, encountered multiple personalities and situations, and seen the good, bad, and ugly of boards.

In Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, the authors provide seasoned advice and guidance to CEOs, board members, investors, and anyone aspiring to serve on a board. This comprehensive book covers a wide range of topics with relevant tips, tactics, and best practices, including:

• Board fundamentals such as the board’s purpose, legal characteristics, and roles and functions of board members;
• Creating a board including size, composition, roles of VCs and independent directors, what to look for in a director, and how to recruit directors;
• Compensating, onboarding, removing directors, and suggestions on building a diverse board;
• Preparing for and running board meetings;
• The board’s role in transactions including selling a company, buying a company, going public, and going out of business;
• Advice for independent and aspiring directors.

Startup Boards draws on the authors’ experience and includes stories from board members, startup founders, executives, and investors. Any CEO, board member, investor, or executive interested in creating an active, involved, and engaged board should read this book—and keep it handy for reference.

Five new mini-books from Startup CXO, but with new bonus material and an obvious focus on each specific functional area.

Each book has several topics in common – chapters on the nature of an executive’s role, how a fractional person works in that role, how the role works with the leadership team, how to hire that role, how the role works in the beginning of a startup’s life, how the role scales over time, and CEO:CEO advice about managing the role.

In Startup CTO (Technology and Product), the role-specific topics Shawn Nussbaum talks about are The Product Development Leaders, Product Development Culture, Technical Strategy, Proportional Engineering Investment and Managing Technical Debt, Shifting to a New Development Culture, Starting Things, Hiring Product Development Team Members, Increasing the Funnel and Building Diverse Teams, Retaining and Career Pathing People, Hiring and Growing Leaders, Organizing Collaborating with and Motivating Effective Teams, Due Diligence and Lessons Learned from a Sale Process, Selling Your Company, Preparation, and Selling Your Company/Telling the Story.

In Startup CMO, the role-specific topics Nick Badgett and Holly Enneking talk about are Generating Demand for Sales, Supporting the Company’s Culture, Breaking Down Marketing’s Functions, Events, Content & Communication, Product Marketing, Marketing Operations, Sales Development, and Building a Marketing Machine.

In Startup CFO, the role-specific topics Jack Sinclair talks about are Laying the CFO Foundation, Fundraising, Size of Opportunity, Financial Plan, Unit Economics and KPIs, Investor Ecosystem Research, Pricing and Valuation, Due Diligence and Corporate Documentation, Using External Counsel, Operational Accounting, Treasury and Cash Management, Building an In-House Accounting Team, International Operations, Strategic Finance, High Impact Areas for the Startup CFO as Partner, Board and Shareholder Management, Equity, and M&A.

In Startup CRO, the role-specific topics Anita Absey talks about are Hiring the Right People, Profile of Successful Sales People, Compensation, Pipeline, Scaling the Sales Organization, Sales Culture, Sales Process and Methodology, Sales Operating System, Marketing Alignment, Market Assessment & Alignment, Channels, Geographic Expansion, and Packaging & Pricing.

In Startup CPO (HR/People), the role-specific topics Cathy Hawley talks about are Values and Culture, Diversity Equity and Inclusion, Building Your Team, Organizational Design and Operating Systems, Team Development, Leadership Development, Talent and Performance Management, Career Pathing, Role Specific Learning and Development, Employee Engagement, Rewards and Recognition, Reductions in Force, Recruiting, Onboarding, Compensation, People Operations, and Systems.

Book Short:  Next, Write a Sequel

Written by Rodd Wagner and James K. Harter and billed as “the long awaited sequel to First, Break All the Rules” (one of the best management books I’ve ever read), I thought 12: The Elements of Great Managing, was good, but not great.  12…, along with the original book First… and Now, Discover Your Strengths, the latter two both by Marcus Buckingham, are all based on an extensive database of research done on corporate America by the Gallup organization over many years.  All three are valuable reads in one way or another, although I found this to be the weakest of the three.  (Note that Now… is different from the other two in that it’s not about management, it’s about self-management — very different, though based on the same research.)

Anyway, the elements of great managing, so say the authors, is all about creating employee engagement.  I totally buy into that.  And since no book short on 12… would be complete if it didn’t list out the 12…

1. Do I know what is expected of me at work?
2. Do I have the materials and equipment I need to do my work right?
3. At work, do I have the opportunity to do what I do best every day?
4. In the last seven days, have I received recognition or praise for doing good work?
5. Does my supervisor, or someone at work, seem to care about me as a person?
6. Is there someone at work who encourages my development?
7. At work, do my opinions seem to count?
8. Does the mission/purpose of my company make me feel my job is important?
9. Are my co-workers committed to doing quality work?
10. Do I have a best friend at work?
11. In the last six months, has someone at work talked to me about my progress?
12. This last year, have I had the opportunities at work to learn and grow?

The book fleshes out each of the 12, gives examples (some of which are better/clearer than others), and then addresses compensation in a very interesting chapter at the end.  Key takeaways on comp:

– Higher pay doesn’t guarantee greater engagement
– Good and bad employees are equally likely to think they deserve a raise
– Money without meaning isn’t enough
– Most employees, most of the time, feel undercompensated
– Individual pay can/should be private, but comp criteria should be very public
– People who feel well-compensated generally work harder

The book also cites a very provocative article suggesting that organizations would handle comp better if they made everyone’s comp public (in contrast to the final bullet above, yes).  I’m going to write more about compensation in future postings, so I’ll leave this section on those notes.

Finally, the book’s two closing thoughts are perhaps its most prescient:  one critical element of BEING a great manager is HAVING a great manager; and the managers who put the most into their people, get the most out of their people.

Half the Benefit is in the Preparation

This past week, we had what has become an annual tradition for us – a two-day Board meeting that’s Board and senior management (usually offsite, not this year to keep costs down) and geared to recapping the prior year and planning out 2009 together.  Since we are now two companies, we did two of them back-to-back, one for Authentic Response and the other for Return Path.

It’s a little exhausting to do these meetings, and it’s exhausting to attend them, but they’re well worth it.  The intensity of the sessions, discussion, and even social time in between meetings is great for everyone to get on the same page and remember what’s working, what’s not, and what the world around us looks like as we dive off the high dive for another year.

The most exhausting part is probably the preparation for the meetings.  We probably send out over 400 pages of material in advance – binders, tabs, the works.  It’s the only eco-unfriendly Board packet of the year.  It feels like the old days in management consulting.  It takes days of intense preparation — meetings, spreadsheets, powerpoints, occasionally even some soul searching — to get the books right.  And then, once those are out (the week before the meeting), we spend almost as much time getting the presentations down for the actual meeting, since presenting 400 pages of material that people have already read is completely useless.

By the end of the meetings, we’re in good shape for the next year.  But before the meetings have even started, we’ve gotten a huge percentage of the benefit out of the process.  Pulling materials together is one thing, but figuring out how to craft the overall story (then each piece of it in 10-15 minutes or less) for a semi-external audience is something entirely different.  That’s where the rubber meets the road and where good executives are able to step back; remember what the core drivers and critical success factors are; separate the laundry list of tactics from the kernel that includes strategy, development of competitive advantage, and value creation; and then articulate it quickly, crisply, and convincingly. 

I’m incredibly proud of how both management teams drove the process this year – and I’m charged up for a great 2009 (economy be damned!).

Book Short: How, Now

Every once in a while, I read a book that has me jump up and down saying “Yes! That’s so right!” How: Why How We Do Anything Means Everything in Business (and in Life), by Dov Seidman, was one of those books.  But beyond just agreeing with the things Seidman says, the book had some really valuable examples and two killer frameworks, one around culture, and one around leadership.

It’s a book about the way the world we now live in — a world of transparency and hyper-connectedness — is no longer about WHAT you do, but HOW you do it. It’s about how you can have a great brand and great advertising, but if your customers find out via a blog and YouTube clip that you run a low quality sweatshop in Malaysia, you are toast. It’s about you can…not outwork the competition, not outsmart the competition, but how you can out-behave the competition.

The book, which talks about principles like mutual gain, and thriving on the collaborative, reminds me a lot of a basic tenet of negotiation I learned years ago at the Harvard Program on Negotiation about finding a “third way” beyond a “me vs. you” negotiation by expanding the pie so both parties get more out of a deal.

Here are a few snippets from the book to inspire a purchase:

– How encouraging doctors to say “I’m sorry” radically reduces lawsuits

– How “micro-inequities” can subtly leech productivity from an organization

– How the majority of workers expect from their workplaces: equity, achievement, camaraderie

– How companies whose employees understand and embrace their mission, goals, and values see a 29% greater return than companies whose employees don’t

– How reputation is the new competitive advantage

– How people will do the right thing because in self-governing cultures, not doing the right thing no longer betrays just the company; it betrays individuals’ own values

– How increasing self-governance means moving values to the center of your efforts and making it clear — in how you reward, celebrate, communicate, and pursue — that those values form the guiding spirit of the enterprise

What type of organization do you run? One based on Anarchy & Lawlessness, one based on Blind Obedience, one based on Informed Acquiescence, or one of Values-Based Self-Governance? (Hint, it’s most likely the third category.) Read the book to find out more.

Book Short:  Entrepreneurial Lessons

The Startup Playbook: Secrets of the Fastest-Growing Startups from 42 Founders, by David Kidder, is the ultimate coffee table book for entrepreneurs and people who are interested in how they think about running their businesses.

David is the author of the Intellectual Devotional series (here’s a link to one of the five or six books in the series), he’s a good friend of mine and a member of a CEO Forum that I’m in, and my major disclosure about this blog post is that I’m one of the 42 entrepreneurs David interviewed for and profiles in the book.

The Startup Playbook is very different from my own book (in progress) on being a Startup CEO.  Where my book is going to go deep on different topics – think of it as a bit of a field guide – David’s book is extremely broad in its coverage of different entrepreneurs and their stories.  Taken together, the book paints a great picture of how CEOs think about the most important parts of the job.  It’s also a nice change of pace (for me, anyway) that David profiles some entrepreneurs who aren’t in the Internet/tech space.

It was an honor to be included in The Startup Playbook next to entrepreneurs like Reid Hoffman and Elon Musk.

Book Short:  A Primer on Viral Marketing

“People talk about Andy,” writes Seth Godin in the foreward to Andy Sernovitz’s new book, Word of Mouth Marketing:  How Smart Companies Get People Talking.   “He’s a living, breathing example of the power of word of mouth.”  Andy’s the CEO of WOMMA, the Word of Mouth Marketing Association, and a former colleague of mine.

Ever since reading The Tipping Point, I keep looking for the secret sauce around viral marketing.  What is it that makes something cool enough to buzz about?  My conclusion from reading Andy’s book is that secret sauce doesn’t exist.  Like everything else, being buzzworthy comes from hard work, being inherently good, AND using the techniques and understanding in Andy’s book.  Tables like “The Three Reasons People Talk About You” and “The Five T’s of Word of Mouth Marketing” are worth the price of the book in and of themselves, as they explain how to manage, handle, and drive viral marketing — once you have your own secret sauce down.

Andy’s wanted to write a book for a long time (in fact, he got us started on ours), and I’m glad he finally did it.  If you’re interested in an easy-to-follow, practical, hands-on guide to viral, or word-of-mouth marketing, this is the book for you.

Book Short:  Unsung Heroes

If you like “entrepreneurship by analogy” books, you’ll like The Innovators:  The Engineering Pioneers Who Made America Modern, by David Billington.  I have to admit some bias here — Professor Billington was my favorite teacher and senior thesis advisor at Princeton (I almost majored in civil engineering because of him), and this book is one of a number he’s written that are outgrowths of his most popular courses at Princeton.  And while there’s no substitute for the length or energy of his lectures, the book works.

The book is basically a person-focused engineering history of America from 1776-1883.  Billington talks about four classes of engineering product:  public structures (mostly bridges), machines that produced power, networks like the railroads and telegraphs, and processes like steel manufacturing.

His approach is to acknowledge that the Americans innovators couldn’t do much without the right context:  learnings from their counterparts in Britain, a supportive government here at home, and abundant raw materials and capital.  But with that backdrop in place, Billington tells the tale of a number of the inventions that built our modern society with a focus on the engineers who got things right.  While some of them are familiar names (Morse, Edison), many are not (Thomas Telford, J. Edgar Thomson, Joseph Henry).

Sound familiar?  It feels at many point in the book that you could insert some different names and dates and be reading a history of the Internet or information age.  And as with the Industrial Revolution, while many of the innovators in our world today are known (Bezos, Yang, Brin/Page), there are probably an equal number who are unsung heroes — either software engineers or even buisness model pioneers who haven’t sought or won’t end up in the spotlight even though their contributions to society or to their companies are giant.  I know there are a number of unsung heroes in our own engineering department at Return Path — people who aren’t market facing and who never get quoted in press releases, but who really make a difference in how the company works and how competitive we are.  This book celebrates those people as much as it does the entrepreneurs you’ve heard of.

Warning, there are lots of pages which are full of mathematical formulas, which may or may not be interesting to you, but the book still holds together 100% if you skip over them.

Book Short:  Deep Dive on Customer Development

I continue to be on a tear reading books about startups as I finish and get ready for the publication of Startup CEO (now available for pre-ordering at Amazon).   This week’s selection was The Startup Owners Manual:  A Step-by-Step Guide for Building a Great Company, by Steve Blank and Bon Dorf.  This book is a significantly more detailed version of Blank’s first book, The Four Steps to the Epiphany, which was a revolutionary book a few years ago that helped spawn the Lean Startup movement.

And when I say significantly, I mean it!  The Startup Owners Manual is 600 pages of really detailed how-to around the first two steps of Blank’s four steps, Customer Discovery and Customer Validation.  It doesn’t get into the last two steps at all, Customer Creation and Company Building.  It has a lot of overlap with Ash Maurya’s Running Lean (post, book), although it’s significantly more detailed.  And essentially, especially around the topic of “Company Building,” my book starts where this one stops.

One of Blank’s great lines in the book is that a “A startup is a temporary organization in search of a scalable, repeatable, profitable business model.”  That frames the whole Lean Startup movement really, really well.  The whole concept of Customer Discovery and Validation, of testing hypotheses, is critical to getting product-marketing fit right in a capital-efficient manner.  If I were starting Return Path today, we’d be using these methods from the get-go.

But Lean principles are wholly compatible with larger companies, as well, and in fact we use all of these principles in our product development organization today.  We adapt them for our size and scale and the fact that often we are selling either new or enhanced versions of existing product into existing customers, but our product teams have all embraced the Lean principles and the vocabulary around them, and our goal is that we should never bring a product to market that isn’t already being bought.

Book Short:  Scrum ptious 

I just finished reading Scrum: The Art of Doing Twice the Work in Half the Time, by Jeff Sutherland and JJ Sutherland. This reading was in anticipation of an Agile Facilitation training my executive team and I are going through next week, as part of Return Path’s  Agile Everywhere initiative. But it’s a book I should’ve read along time ago, and a book that I enjoyed.

Sutherland gets credit for creating the agile framework and bringing the concept scrum to software development over 20 years ago. The book very clearly lays out not just the color behind the creation of the framework, and the central tenets of practice again, but also clear and simple illustrations of its value and benefits.  And any book that employs the Fibonacci series and includes Theodore Roosevelt’s “Man in the Arena” quote — my all-time favorite — is off to a good start by me.

I’ve always appreciated a lot of the underlying philosophy of Agile, such as regularly checking on projects, course correcting in response to feedback from customers or other stakeholders, and working hard to remove any impediments to progress in real time.

One of the author’s most poignant points is that “multitasking makes you stupid.”  I hadn’t focused in the past how agile allows you to clear away context shifts to focus on one task at a time, but that’s another great take away from the book.

Our Agile Everywhere initiative, which is designed to improve productivity across the organization, as well as increase accountability through transparency, is even more critical in my view after having read this book.

The thing that I am left struggling with, which is still very much a work in progress for us, and hopefully something that we will address more head on in our training next week, is the application of the agile framework to teams that are not involved in the production of a tangible work product, such as executive or other leadership teams.  That is something that our Agile Everywhere deployment team has developed a theory about, but it still hasn’t entirely sunk in for me.

I can’t wait for next week’s training session!  If you have any experience applying the agile framework to different types of teams in your company I’d love to hear more about it in the Comments.

Startup CEO (OnlyOnce – the book!)

One of the things I’ve often thought over the years since starting Return Path in 1999 is that there’s no instruction manual anywhere for how to be a CEO.  While big company CEOs are usually groomed for the job for years, startup CEOs aren’t…and they’re often young and relatively inexperienced in business in general.  That became one of the driving forces behind the creation of my blog, OnlyOnce (because “you’re only a first time CEO once”) back in 2004.

Now, over 700 blog posts later, I’m excited to announce that I’m writing a book based on this blog called Startup CEO:  A Field Guide to Building and Running Your Company.  The book is going to be published by Wiley & Sons and is due out next summer.  The book won’t just be a compendium of blog posts, but it will build on a number of the themes and topics I’ve written about over the years and also fill in lots of other topics where I haven’t.

The catalyst for writing this book was Brad Feld.  Brad has been a friend, mentor, investor, and Board member for over a decade.  We’ve had many great times, meals, and conversations together over the years, not the least of which was staggering across the finish line together at the New York City Marathon in 2005.  Brad started writing books a few years ago, and I’ve been peripherally involved with them, first with Do More Faster:  TechStars Lessons to Accelerate Your Startup (I contributed one of the chapters) and then with Venture Deals:  Be Smarter Than Your Lawyer and Venture Capitalist (I wrote all the “Entrepreneur Perspective” sidebars).

Those are great books, and they’ve been incredibly well received by the global entrepreneurial community.  But then Brad got the bug, and now he’s in the middle of writing FOUR new books with Wiley that will all come out over the next year.  They are:

• Startup Communities:  Building an Entrepreneurial Ecosystem in Your City
• Startup Life:  Surviving and Thriving in a Relationship with an Entrepreneur
• Startup Metrics:  Making Sense of the Numbers in Your Startup
• Startup Boards:  Reinventing the Board of Directors to Better Support the Entrepreneur

These four books, plus the two earlier ones, plus Startup CEO, are all part of the Startup Revolution series.  While I’ll continue to do most of my blogging and posting here on OnlyOnce, I’d also encourage you to check out the Startup Revolution site and sign up to be a member of that community.  I’ll be doing some things on that site as well in connection with Startup CEO, and it’s a more concentrated place to post and comment on all things Startup.  In addition, we’ll be putting a bunch of add-ons to the book on that site closer to publication time.

I hope Startup CEO becomes a standard for all new CEOs.  I don’t think I have all the answers, but at least others can benefit by learning from my 13 years of successes and mistakes!  Now all I have to do is go write the darned thing.

I haven’t done short book summaries in a LONG time, but I’ll try to start adding that back into the mix as I read interesting and relevant books. Here’s one to add to your list: One Life to Lead, by Russell Benaroya. I was recently connected to Russell by a mutual friend, TA McCann at Pioneer Square Labs. TA had a sense Russell and I would hit it off, and we did. Russell is a multi-time founder/CEO, a Coach, and an author, so we have a lot in common.

One Life to Lead is an excellent book. First, it is short and easy to get through. Unlike a lot of business books, it doesn’t go on too long or contain anything extraneous. It’s to the point!

Second, the book is a business book that’s not really about business. It’s about life and what Russell calls Life Design, which is a great framing of how to be intentional about leading your life. While I have become less and less of a life planner as I’ve gotten older under the headline of “man plans, God laughs,” I am a huge believer in being intentional about everything, which I talk about in Startup CEO quite a bit in the nuts and bolts context of building your business.

Finally, Russell’s framework is easy to understand and full of concrete exercises you can to. Here are his five steps, but you’ll have to read the book to get the details:

• Ground stories with facts. This reminds me a lot of the principles we have taught team members over the years in our Action/Design (and related) trainings. First, start with absolute concrete facts that everyone will agree are facts.
• Establish your principles. This is brilliant. Your company has documented values or operating principles. Why don’t you?
• Harness energy from the environment. Figuring out what makes you tick, and what drains your energy, is so important.
• Get in and stay in your genius zone. Shouldn’t we all focus our time on the things we do best and love the most?
• Take action. How to put it together and make it all happen.

If you don’t get out in front of life, it will happen to you, and Russell’s framework is about how to make sure you are in the driver’s seat of your own life. Here’s to that.