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.
The Ideal Team Player: How to Recognize and Cultivate The Three Essential Virtues(hardcover,kindle is Patrick Lencioni’s latest and greatest. It’s not my favorite of his, which is still The Advantage (post,buy ), but it’s pretty good and well worth a read. It builds on his model for accountability in The Five Dysfunctions of a Team (post,buy)and brings it back to “how can you spot or develop and a good team player?”
The central thesis of the book is that great team players have three attributes – hungry, humble, and people-smart. While I can’t disagree with those three things, as with all consultants’ frameworks, I sound two cautionary notes: (1) they aren’t the absolute truth, just a truth, and (2) different organizations and different cultures sometimes thrive with different recipes. That said, certainly for my company, this framework rings true, if not the only truth.
Some great nuggets from the book:
-The basketball coach who says he loves kids who want to come to practice and work as hard as they can at practice to avoid losing
-The concept of Addition by Addition and Addition by Subtraction in the same book – both are real and true. The notion that three people can get more done than four if the fourth is a problem is VERY REAL
-When you’re desperate for people, you do stupid things – you bring people on who can get the job done but shouldn’t be in your environment. I don’t know a single CEO who hasn’t made this mistake, even knowing sometimes that they’re in the process of making it
The framing of the “edge” people – people who have two of the three virtues, but not the third, is quite good:
-Hungry and Humble but not People-Smart – The Accidental Mess Maker -Humble and People-Smart, but not Hungry – The Lovable Slacker -Hungry and People-Smart, but not Humble – The Skillful Politician
In my experience, and Lencioni may say this in the book, too (I can’t remember and can’t find it), none of these is great…but the last one is by far the most problematic for a culture that values teamwork and collaboration.
Anyway, I realize this is a long summary for a short book, but it’s worth buying and reading and having on your (real or virtual) shelf. In addition to the story, there are some REALLY GOOD interview guides/questions and team surveys in the back of the book.
I enjoy reading books written by people I know. I can always picture the person narrating the book, or hear their voice saying the words, I can periodically see their personality showing through the words on the page, and books bring out so much more detail than I’d ever get from a conversation. Loved: How to Rethink Marketing for Tech Products, by Martina Lauchengco, is one of those books. Martina is an operating partner at Costanoa Venture Capital, an investor in both Return Path and Bolster, and I’d known Martina for several years before she joined Costanoa through Greg Sands. She’s the best product marketer on the planet. She’s the also one of the nicest people around.
Product Marketing is a tricky discipline. A brand marketer on my leadership team years ago referred to it somewhat derisively as a “tweener” function, one of those things that’s not quite marketing and not quite product. We didn’t get the function right for many years at Return Path because we treated it that way, thinking “well, it’s neither fish nor fowl, so we’re not quite sure what to do with it.” Then we hired Scott Roth, who has gone on to have a storied career as a multi-time CEO. Scott’s background was in product marketing. He said to me in his interview process, “Product Marketing isn’t a tweener function with no home. It’s a glue function. It holds product and marketing together.” It’s amazing how that simple change in framing, combined with great leadership, led us to completely rethink the function and make it one of the most important functions in the company.
Martina brings that to live with Loved. Simply put, Loved is a handbook or a field guide to running the Product Marketing function. I can imagine it being a section of Startup CXO in that way — it’s incredibly practical, hands-on, how-to, and rich with examples from Martina’s amazing career at Microsoft, Netscape, Silicon Valley Product Group, and Costanoa. And she believes in Agile Marketing, which is always a plus in my book (and I find rare in marketers).
Martina has lots of great frameworks and stories in the book – key responsibilities of product marketing, key metrics, the release scale, the connection to Geoffrey Moore’s TALC, strategies for messaging, pricing and packaging, and more. I won’t spoil more than one here, but I will paraphrase one that I found particularly impactful, a bit of a checklist on the essence of great product marketing:
Share data around shifting trends in buyer behavior
Connect your product’s purpose with broader trends
Rebrand to make your product seem bigger than it is (and save room for expansion down the road)
Make it free, especially if you’re defining a new category
Share the “why” and advance access with influencers
If the measure of a book’s impact is how many pages you dog ear or highlight, this says it all about Loved.
I’m sure author Robert Cialdini would blanch if he read this comparison, but then again, I can’t be the first person to make it, either. His book, Influence: The Psychology of Persuasion, is an outstanding read for any marketing or sales professional, but boy does it remind me of Malcolm Gladwell’s The Tipping Point and Blink (book; blog post). Of course, Cialdini’s book came out a decade before Gladwell’s! Anyway, Influence is a great social science look at the psychology that makes sales and marketing work.
Cialdini talks about sales and marketing professionals as “compliance practitioners,” which is a great way to think about them, quite frankly. He boils down the things that make sales and marketing work to six core factors: consistency, reciprocation, social proof, authority, liking, and scarcity.
Reciprocation – we hate being in a state of being beholden so much that we might even be willing to do a larger favor than the one done for us in order to remove the state. Think about “free gifts” in merchandising as an example of this, or being in a negotiation where someone trying to make a cold sale on you offers a fallback, smaller sale. For example, you don’t want to buy anything from the boy scout, but after you say no to the $5 raffle ticket and he asks about the $1 candy bar, you feel more obligated to buy the $1 candy bar because the boy scout has “given” on his initial request.
Consistency – once we have made a choice, personal and interpersonal pressures force us to back it up and justify our earlier decision – even more so when in writing or when declared to others. This is why marketers love getting testimonials from customers; the testimonial locks the customer in emotionally, as well as encouraging others to buy the product.
Social proof – if others think it’s correct, it must be correct, especially if those other people are like us. There are some scary examples in the book here, such as Reverand Jim Jones and The People’s Temple mass suicides. Gripping, but creepy.
Liking – we listen to people we like, and we like people to whom we’re similar or who are physically attractive. This section was especially reminiscent of Blink, but with different and more marketer-focused examples.
Authority – we have an extreme willingness to listen to authority, even when the authority isn’t quite relevant. This is why celebrity endorsements work so well.
Scarcity – we have a extreme motivation of fear of loss, either or something, or of the opportunity to have something. Who doesn’t like to keep doors open as long as possible?
The one place the book falls down a little bit is in the sections at the end of each chapter talking about how to resist that particular technique through jujitsu – the art of “turning the enemy’s strength to your advantage.” While nice in theory, Cialdini’s examples aren’t super helpful beyond saying “when you think you’re getting suckered, stop — and then say no.”
Overally, though, the book is well written and choc full of examples. Thanks to marketer Mallory Kates for sending me this great book!
Joy, Inc.: How We Built a Workplace People Love, by Richard Sheridan, CEO of Menlo Innovations, was a really good read. LikeRemote which I reviewed a few weeks ago, Joy, Inc. is ostensibly a book about one thing — culture — but is also full of good general advice for CEOs and senior managers.
Also like Remote, the book was written by the founder and CEO of a relatively small firm that is predominately software engineers, so there are some limitations to its specific lessons unless you adapt them to your own environment. Unlike Remote, though, it’s neither preachy nor ranty, so it’s a more pleasant read. And I suppose fitting of its title, a more joyful read as well. (Interestingly on this comparison, Sheridan has a simple and elegant argument against working remotely in the middle of the book around innovation and collaboration.)
Some of the people-related practices at Sheridan’s company are fascinating and great to read about. In particular, the way the company interviews candidates for development roles is really interesting — more of an audition than an interview, with candidates actually writing code with a development partner, the way the company writes code. Different teams at Return Path interview in different ways, including me for both the exec team and the Board, but one thing I know is that when an interview includes something that is audition-like, the result is much stronger. There are half a dozen more rich examples in the book.
Some of the other quotable lines or concepts in the book include:
the linkage between scalability with human sustainability (you can’t grow by brute force, you can only grow when people are rested and ready to bring their brain to work)
“Showcasing your work is accountability in action” (for a million reasons, starting with pride and ending with pride)
“Trust, accountability, and results — these get you to joy” (whether or not you are a Myers-Briggs J, people do get a bit of a rush out of a job well done)
“…the fun and frivolity of our whimsically irreverent workplace…” (who doesn’t want to work for THAT company?)
“When even your vendors want to align with your culture, you know you’re on the right path” (how you treat people is how you treat PEOPLE, not just clients, not just colleagues)
“One of the key elements of a joyful culture is having team members who trust one another enough to argue” (if you and I agree on everything, one of us is not needed)
“The reward is in the attempt” (do you encourage people to fail fast often enough?)
“Good problems are good problems for the first five minutes. Then they just feel like regular problems until you solve them” (Amen, Brother Sheridan)
The benefits of a joyful culture (at Return Path, we call it a People-First culture) have long been clear to me. As Sheridan says, we try to “create a culture where people want to come to work every day.” Cultures like ours look soft and squishy from the outside, or to people who have grown up in tough, more traditional corporate environments. And to be fair, the challenge with a culture like ours is keeping the right balance of freedom and flexibility on one side and high performance and accountability on the other. But the reality is that most companies struggle with most of the same issues — the new hire that isn’t working out or the long-time employee who isn’t cutting it any more, the critical path project that doesn’t get done on time, the missed quarter or lost client. As Sheridan notes though, one key benefit of working at a joyful company is that problems get surfaced earlier when they are smaller…and they get solved collaboratively, which produces better results. Another key benefit, of course, is that if you’re going to have the same problems as everyone else, you might as well have fun while you’re dealing with them.
If you don’t love where you work and wish you did, read Joy, Inc. If you love where you work but see your company’s faults and want to improve them, read Joy, Inc. If you are not in either of the above camps, go find another job!
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.
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.
I keep expecting one of his books to be repetitive or boring, but Patrick Lencioni’s The Five Dysfunctions of a Team held my interest all the way through, as did his others. It builds nicely on the last one I read, Death by Meeting (post, link).
I’d say that over the 9 1/2 years we’ve been in business at Return Path, we’ve systematically improved the quality of our management team. Sometimes that’s because we’ve added or changed people, but mostly it’s because we’ve been deliberate about improving the way in which we work together. This particular book has a nice framework for spotting troubles on a team, and it both reassured me that we have done a nice job stamping out at least three of the dysfunctions in the model and fired me up that we still have some work to do to completely stamp out the final two (we’ve identified them and made progress, but we’re not quite there yet.
The dysfunctions make much more sense in context, but they are (in descending order of importance):
Absence of trust
Fear of conflict (everyone plays politically nice)
Lack of commitment (decisions don’t stick)
Avoidance of accountability
Inattention to results (individual ego vs. team success)
For those who are wondering, the two we’re still working on at the exec team level here are conflict and commitment. And the two are related. If you don’t produce engaged discussion about an issue and allow everyone to air their opinions, they will invariably be less bought into a decision (especially one they don’t agree with). But we’re getting there and will continue to work aggressively on it until we’ve rooted it out.
There’s one other interesting takeaway from the book that’s not part of the framework directly, which is that an executive has to be first and foremost a member of his/her team of peers, not the head of his/her department. That’s how successful teams get built. AND (this is key) this must trickle down in the organization as well. Everyone who manages a team of group heads or managers needs to make those people function well as a team first, then as managers of their own groups second.
At any rate, another quick gem of a book. I’m kind of sorry there’s only one left in the series.
The Entrepreneur’s Guide to Business Law, by Constance Bagley (HBS) and Craig Dauchy (Cooley Godward), while not exactly a page-turner, is a great reference book for even experienced CEOs. It’s pretty broad in its coverage of all major legal issues an entrepreneur will face, from patent law to firing employees.
Remember, you may make fun of lawyers on occasion or grips about their fees, but they DID attend law school for three years, after all. If nothing else, the $20 on this book will almost certainly save you at least 10x that in reduced legal fees someday, for something.
Trade Show and Event Marketing: Plan, Promote, and Profit, by our direct marketing colleague Ruth Stevens, is hardly a page-turner, but it is a great read and well worth the money for anyone in your B2B marketing department. That’s true as much for the event marketing specialist as the marketing generalist.
The author brings a very ROI-focused approach to planning and executing events – whether big trade shows or smaller corporate events, which are becoming increasingly popular in recent years for cost, focus, and control reasons. But beyond events, the book has a number of excellent checklists that are more general for marketers that I found quite useful both as a reminder of things we should be doing at Return Path as well as ways we should be thinking about the different elements of our B2B marketing mix.
Some of the best tables and charts include: strengths, weaknesses, and best applications of trade shows vs. corporate events; comparative analysis of marketing tools by channel (this was great – talks about best applications for all major tools from events to newsletters to search to inside sales); 12-month exhibitor timeline for trade shows; a great riff on bad booth signage vs. good booth signage (hint: don’t make the visitor do the work – be obvious!); business event strategic planning grid; pre-show campaign and post-show follow-up checklists; dos, don’ts and options for corporate events; a great section on qualifying and handling leads that extends well beyond trade shows; and several good case studies that are show-focused.
Thanks to Ruth herself for an autographed copy! Team Marketing and sales leaders at Return Path – your copies are on the way.
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:Â 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.
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