My latest book (I’m a co-author along with Brad Feld and Mahendra Ramsinghani), Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors, is now live on Amazon – today is publication day! The book is a major refresh of the first edition, now eight years old. I was quoted in it extensively but not an official author – Brad and Mahendra were nice enough to share that with me this time. The book includes a lot of new material and new voices, including a great Foreword by Jocelyn Mangan from Him for Her and Illumyn. It’s aligned with Startup CEO and Startup CXO in look and in format and is designed to be an easy-to-read operator’s manual to private company boards of directors. Brad also blogged about it here.

We’ve done a lot of work around startup boards at Bolster the past couple of years, including working with over 30 CEOs to help them hire amazing new independent board members. Our landmark Board Benchmark study last year highlighted the problem with startup boards, but also the opportunity that lies within: not enough diversity on the boards, but also not nearly enough independent directors — and a lot of open seats for independent directors that could be filled. That conclusion led me to my Startup Board Mantra of 1-1-1: Independent directors from Day 1, 1 member of the management team, and 1 independent for every 1 investor.

As we posted on the Bolster blog last week, our quick refresh of the Board Benchmark study revealed some good news and some bad news about progress on diversity in the boardroom with startups. The good news is that the needle is starting to move very slowly, and that independent directors present the best opportunity to add diversity to boards. Our data shows that half of all new directors brought onto boards in the last year were independents, and of those, 57.9% were women and 31.6% were non-White board members. Those numbers are well above the prior study’s benchmarks of 36% and 23%, respectively (our experience running board searches skews even further to women and non-White directors being hired).

The bad news is how slowly the needle is moving — only 20% of open independent board seats were filled over the previous year, which is a lot of missed opportunity. The main takeaway is that while overall representation on boards is still skewed largely White and male, the demographic profile of new board appointments looks a lot different from the representation on boards today, indicating that CEOs are making intentional changes to their board composition.

Startup boards are a great way to drive grassroots change to the face of leadership in corporate America. More CEOs need to follow up by filling their open board seats and fulfilling their stated desires to improve diversity in the boardroom. This takes time and prioritization — these are the places where we see board searches either never get off the ground, or falling down once they do, for all the searches we either run or pitch at Bolster.

Hopefully Startup Boards will help the startup ecosystem get there.

As I mentioned the other day, the second edition of Startup CEO is out.  This post is a teaser for the content in one of the new chapters in this edition on Authentic Leadership.

As I mentioned last week, the book went to press early in the COVID-19 pandemic and prior to all the protests around racial injustice surrounding the George Floyd killing, so nothing in it specifically addresses any of those issues.  In some ways, though, that may be better at the moment since the book is more about frameworks and principles than about specific responses to current events. Two of those principles, which are timeless and transcend turmoil, uncertainty, time and place, are creating space to think and reflect and being intentional in your actions. In a world in which CEOs are increasingly called upon to deal with more than traditional business (pricing, strategy, go-to market approaches, team building, etc.) it’s imperative to approach and solve challenging situations from a foundation that doesn’t waver. 

At Return Path our values were the foundation that provided a lens through which we made every decision. Well, not every decision, only the good ones. When we strayed from our core values, that got us into trouble. The other principle, outlined in Chapter 1 of the Second Edition, is leading an organization authentically.

Let me provide a couple concrete examples of what I mean by “Authentic Leadership” since the term can be interpreted many ways.

One example is to avoid what I call the “Say-Do” gap.  This is obviously a very different thread than talking about how the company relates to the outside world and current events.  But in some ways, it’s even more important.  A leader can’t truly be trusted and followed by their team without being very cognizant of, and hopefully avoiding close to 100%, any gap between the things they say or policies they create, and the things they do.  There is no faster way to generate muscle-pulling eyerolls on your team than to create a policy or a value and promptly not follow it. 

I’ll give you an example that just drove me nuts early in my career here, though there are others in the book.  I worked for a company that had an expense policy – one of those old school policies that included things like “you can spend up to $10 on a taxi home if you work past 8 pm unless it’s summer when it’s still light out at 8 pm” (or something like that).  Anyway, the policy stipulated a max an employee could spend on a hotel for a business trip, but the CEO  (who was an employee) didn’t follow that policy 100% of the time.  When called out on it, did the CEO apologize and say they would follow the policy just like everyone else? No, the CEO changed the policy in the employee handbook so that it read “blah blah blah, other than the CEO, President, or CFO, who may spend a higher dollar amount at his discretion.”

What does that say about the CEO? How engaged are employees likely to be, how much effort are they willing to devote to the company if there are special rules for the executives? You can make any rule you want — as you probably know if you have read a bunch of my posts or my book over the years, I’m a proponent of rule-light environments — but you can’t make rules for everyone else that you aren’t willing to follow yourself unless you own the whole company and don’t care what anyone thinks about you or says about you behind your back.

Beyond avoiding the Say-Do Gap, this new chapter of the book on Authentic Leadership also talks about how CEOs respond to current events in today’s increasingly politicized and polarized world.  This has always felt to me like a losing proposition for most CEOs, which I talk about quite a bit in the book.  When the world is polarized, whatever you do as CEO, whatever position you take on things, is bound to upset, alienate, or infuriate some nontrivial percentage of your workforce.  I even give some examples in the book of how I focused on using the company’s best interests and the company’s values as guideposts for reacting (or not reacting) to politically divisive or charged issues like guns or “religious liberty” laws.  I say this noting that there are some people who *believe* that their side of an issue like this is right, and the other side is wrong, but the issues have some element of nuance to them.

Today’s world feels a bit different, and I’m not sure what I would be doing if I was leading a known, scaled enterprise at this stage in the game.  The largely peaceful protests around all aspects of racial injustice in America in the wake of the murder of George Floyd — and the brutality and senselessness of that murder itself — have caused a tidal wave of dialog reaching all corners of the country and the world.  The root of this issue doesn’t feel to me like one that has a lot of nuance or a second side to the argument.  After all, what reasonable person is out there arguing that George Floyd’s death was called for, or even that black Americans don’t have a deep-seeded and widespread reasonable claim to inequality…even if their view of what to do about it differs?

I *think* what I would be doing in a broader leadership role today is figuring out what my organization could be doing to help reduce or eliminate structural racial inequality where we could based on our business, as opposed to driving my organization to take a specific political stand. I know for sure that I wouldn’t solicit feedback from a select group of people only, but I would create a space where voices from across the organization (and stakeholders outside of it as well) could be heard. That’s not a solution, but a start, and in challenging times making a little bit of headway can lead to a cascading effect. It can, if you keep the momentum.

And, in line with “authentic leadership,” it’s okay to admit that you don’t have the answers, that you might not even know the questions to ask. But doing nothing, or operating in a “business as usual” way won’t make your company stronger, won’t open up new opportunities, won’t generate new ideas, and won’t sit well with your employees, who are very much thinking about these issues. 

So, in today’s challenging times I would follow my own advice, be thoughtful and reflective, and intentional in searching for common solutions.  I’d try to avoid “mob mentality” pressure — but I would also be listening carefully to my stakeholders and to my own conscience.

In the coming weeks, I’ll write posts that get into some of the other topics I cover in the book, but none of them will be as good as reading the full thing!

Startup CEO (OnlyOnce- the book!), Part II – Crowdsourcing the Outline

As I mentioned a few weeks ago here, I’m excited to be writing a book called Startup CEO:  A Field Guide to Building and Running Your Company, to be published by Wiley & Sons next summer.  Since many readers of OnlyOnce are my target audience for the book, I thought I’d post my current outline and ask for input and feedback on it.  So here it is, still a bit of a work in progress.  Please comment away and let me know what you think, what’s missing, what’s not interesting!

1           Part One: Vision and Strategy (Defining the Company)
1.1          Setting the Company’s Agenda
1.2          NIHITO! (or, “Nothing Interesting Happens in the Office”)
1.3          Setting the Business Direction
1.4          Strategic Planning, Part I: Turning Concepts Into Strategy
1.5          Strategic Planning, Part II: Creating the Plan
1.6          Defining Mission, Vision and Values
1.7          Communicating Vision and Strategy
1.8          The Role of M&A
1.9          The Art of the Pivot
1.10       How Vision and Strategy Change over Time

2           Part Two: Talent (Building the Company’s Human Capital)
2.1          Building a Team
2.2          Scaling the Team
2.3          Culture
2.4          Interviewing
2.5          Recruiting
2.6          Onboarding
2.7          Setting Goals
2.8          Feedback
2.9          Development
2.10       Compensation
2.11       Promoting
2.12       Rewarding
2.13       Managing Remote Offices and Employees
2.14       Firing: When It’s Not Working
2.15       How Talent Changes over Time

3           Part Three: Execution (Aligning Resources with Strategy)
3.1          Making Sure There’s Enough Money in the Bank
3.2          Types of Financing
3.3          Fundraising Basics
3.4          Negotiating Deals
3.5          Pros and Cons of Outside Financing
3.6          Forecasting and Budgeting
3.7          Creating a Company Operating System
3.8          Meeting Routines
3.9          Driving Alignment
3.10       A Metrics-Driven Approach to Running a Business
3.11       Learning
3.12       Post-Mortems
3.13       Thinking About Exits
3.14       How Execution Changes over Time
3.14.1      Finance
3.14.2      Execution

4           Part Four: Management And Leadership (The How of Being a CEO)
4.1          Leading an Executive Team
4.2          Critical Personal Traits
4.3          Being Collaborative
4.4          Being Decisive: Balancing Authority and Consensus
4.5          The Value of Symbolism
4.6          Getting the Most out of People
4.7          Diving Deep without Being Disruptive
4.8          Articulating Purpose
4.9          Collecting Data from the Organization
4.10       Managing in an Economic Downturn
4.11       Managing in Good Times vs. Bad Times
4.12       Communication
4.12.1      Macro (to Your Company and Customers)
4.12.2      Micro (One-on-One)
4.13       How Management and Leadership Change over Time

5           Part Five: Boards (A Unique Aspect of the CEO’s Job)
5.1          Building Your Board
5.2          Meeting Materials
5.3          Meetings
5.4          Between Meetings
5.5          Making Decisions and Maximizing Effectiveness
5.6          The Social Aspects of Running a Board
5.7          Working with the Board on Compensation
5.8          Evaluating the Board
5.9          Serving on Other Boards
5.10       How Boards Change over Time

6           Part Six: Managing Yourself So You Can Manage Others
6.1          Creating a Personal Operating System
6.2          Working with an Executive Assistant
6.3          Working with a Coach
6.4          Finding Your Voice
6.5          The Importance of Peer Groups
6.6          Your Family
6.7          Taking Stock
6.8          Staying Fresh
6.9          Staying Healthy
6.10       Traveling

Book Shorts:  Sales, Sales, Sales, Sales, Sales

Jeffrey Gitomer’s Little Red Book of Selling and Little Red Book of Sales Answers were great refreshers in sales basics for you as CEO (and head of sales, and sales manager, and sales rep).  The books were a bit “self-help” flavor for my taste as a reader, but they were excellent on content, and I have two long pages of notes of “back to basics” items I need to remind myself and my team about.

Anyone at Return Path in sales/account-project management/marketing — your copy is on the way, hopefully by way of a barter I proposed with the author (sorry, Stephanie and Tami…), but in any case, we’ll buy them.  Anyone else who is interested at RP, let me know, and the copy is on me.

Some of the most critical reminders — although you have to read the books to get to get the color:

– Ask questions, don’t talk talk talk at prospects (just like the SPIN Selling methodology we always train with at Return Path)

– Never say “tell me a little bit about your business” — do the research first

– Importance of testimonials in selling

– Never blame others or blame circumstances when things go wrong.  Take control and solve the problem (good for sales and for everyone!)

Seth Responds

About an hour after I posted a not so flattering review of Seth Godin’s new book this morning, I got an email from Seth with a couple good points worth responding to here.

His main points (other than offering me a refund, which was nice) were that (a) the book itself was very clear about its content — on the book itself (back cover, inside flap, marketing copy), kind of like a ‘live album’ for a recording artist; and (b) if I thought the blog postings were worthwhile, why  did I still feel like there was a downward trend in his writing?

Ok, so these are fair points.  Let me try to clarify.  I am 99% sure that I bought the book off the Amazon.com email which said “if you enjoyed other books by Seth Godin, then here’s his latest,” which prompted my robotic one-click order without paying attention to the fine print.  That’s why I was disappointed when I got the book.  My bad, I guess, although that’s somehow an unsatisfying thought as a consumer — that I should have paid more attention to the fine print.  Live albums from musicians usually have that in the title so the marketing is clear, and they still sell a ton, probably even more so.

In re-reading my review, I actually think it’s balanced — I do say there are a bunch of circumstances where the book is a must-have — but my use of the word “sell-out” was a bit harsh given the attempts to present the book as a compendium.  But the downward trend in my mind is more than just this book.  I think a lot of Seth’s writings have been hitting the same notes for the last couple of years, while I’ve been hoping to hear his next Big Moo.

I didn’t take up Seth’s offer for a refund, as I fall somewhere between (a) and (c) in my definition of why this is a must-have.  And while I’m at it, maybe I should rethink my earlier point that this whole blog thing isn’t about conversations.

Doing Well by Doing Good, Part IV

This series of posts has mostly been about things that people or companies do that help make the world a better place — sometimes when it’s their core mission, other times (here and here) when it becomes an important supporting role at the company.

Today’s post is different — it’s actually a Book Short as well of a new book that’s coming out later this fall called Green to Gold:  How Smart Companies Use Environmental Strategy to Innovate, Create Value, and Build Competitive Advantage, published by Yale Press and written by Daniel Esty (a Yale professor and consultant), and a good friend of mine, Andrew Winston, a corporate sustainability consultant.

Green to Gold is a must-read for anyone who (a) holds a leadership position in business or is a business influencer, and (b) cares about the environment we live in.  Its subtitle really best describes the book, which is probably the first (or if not, certainly the best) documentation of successful corporate environmentalstrategy on the market.

It’s a little reminiscent to me of Collins Built to Last and Good to Great in that it is meticulously researched with a mix of company interviews/cooperation and empirical and investigative work.  It doesn’t have Collins “pairing” framework, but it doesn’t need to in order to make its point.

If you liked Al Gore’s movie, An Inconvenient Truth, this book will satisfy your thirst for information about what the heck the corporate world is doing or more important, can do, to do its part in not destroying our ecosystem.  If you didn’t like Gore’s movie or didn’t see it because you don’t like Al Gore or don’t think that many elements of the environmental movement are worthwhile, this book is an even more important read, as it brings the theoretical and scientific to the practical and treats sustainability as the corporate world must treat it in order to adopt it as a mainstream practice — as a driver of capitalistic profit and competitive advantage.

This is a really important work in terms of advancing the cause of corporate social responsibility as it applies to the environment.  Most important, it proves the axiom here that you can, in fact, Do Well by Doing Good.  If you’re interested, you can pre-order the book here.  Also, the authors are writing a companion blog which you can get to here.

Book Shorts:  Fred the Cow?

I enjoyed two interesting, super-quick reads from last week that have a common theme running through them:  being remarkable.

The Fred Factor, by Mark Sanborn, is one of those learn-by-storytelling business novellas.  It’s all about the author’s mailman, Fred, and how Fred has figured out how to make a difference in people’s lives even with a fairly routine job.  The focal points of the book are things like “practice random acts of kindness” and “turn the ordinary into the extraordinary by putting passion into your work.”  It’s a good reminder that it is unbelievably easy, not to mention free, to be kind and thoughtful, and that those things are always always always worth doing.  Kinda makes me wonder what the Brad factor is.  <g>

The Big Moo, a collection of essays written by 33 different business thinkers/writers and edited by Seth Godin, isn’t out yet, but you can pre-order it via that link on Amazon.  It follows the main theme of another of Seth’s books, Purple Cow, about how to make your business remarkable and backs it up with various vignettes from the different writers.  It has some great reminders about how easy and inexpensive it can be to be remarkable in business.  Wisdom like “Criticism?  Internalize it,” and “Get great ideas about your business from new employees,” and “How would you run your business if you relied on donations from your customers in order to survive?” are all insightful and thought provoking.

Each is great and an easy read, and while one is more personal and the other business-oriented, in they are both somewhat remarkable.

I read a ton of books.  I usually blog about business books, at least the good ones.  I almost never blog about fiction or non-business/non-fiction books, but I had a good “what did you read this summer” conversation the other night with my CEO Forum, so I thought I’d post super quick snippets about my summer reading list, none of which was business-related.

If you have kids, don’t read Sheryl Sandberg and Adam Grant’s Option B:  Facing Adversity, Building Resilience, and Finding Joy unless you’re prepared to cry or at least be choked up.  A lot.  It is a tough story to read, even if you already know the story.  But it does have a number of VERY good themes and thoughts about what creates resilience (spoiler alert – my favorite key to resilience is having hope) that are wonderful for personal as well as professional lives.

Underground Airlines, by Ben Winters, is a member of a genre I love – alternative historical fiction.  This book is set in contemporary America – except that its version of America never had a Civil War and therefore still has four slave states.  It’s a solid caper in its own right, but it’s a chillingly realistic portrayal of what slavery and slave states would be like today and what America would be like with them.

Hillbilly Elegy, by J.D. Vance, is the story of Appalachia and white working class Americans as told by someone who “escaped” from there and became a marine, then a Yale-educated lawyer.  It explains a lot about the struggles of millions of Americans that are easy for so many of us to ignore or have a cartoonish view of.  It explains, indirectly, a lot about the 2016 presidential election.

Everybody Lies:  Big Data, New Data, and What the Internet Can Tell Us About Who We Really Are, written by Seth Stephens-Davidowitz, was like a cross between Nate Silver’s The Signal and The Noise and Levitt & Dubner’s Freakonomics.  It’s full of interesting factoids derived from internet data.  Probably the most interesting thing about it is how even the most basic data (common search terms) are proving to be great grist for the big data mill.

P.J. O’Rourke’s How the Hell Did This Happen? was a lot like the rest of P.J. O’Rourke’s books, but this time his crusty sarcasm is pointed at the last election in a compilation of articles written at various points during the campaign and after.  It didn’t feel to me as funny as his older books.  But that could also be because the subject was so depressing.  The final chapter was much less funny and much more insightful, not that it provides us with a roadmap out of the mess we’re in.

Sapiens: A Brief History of Humankind, by Noah Harari, is a bit of a rambling history of our species.  It was a good read and lots of interesting nuggets about biology, evolution, and history, though it had a tendency to meander a bit.  It reminded me a bit of various Richard Dawkins books (I blogged a list of them and one related business topic here), so if you’re into that genre, this wouldn’t be bad to pick up…although it’s probably higher level and less scientific than Dawkins if that’s what you’re used to.

Finally, I finished up the fourth book in the massive Robert Caro quadrilogy biography of Lyndon Johnson (full series here).  I have written a couple times over the years about my long-term reading project on American presidential biographies, probably now in its 12th or 13th year.  I’m working my way forward from George Washington, and I usually read a couple on each president, as well as occasional other related books along the way.  I’ve probably read well over 100 meaty tomes as part of this journey, but none as meaty as what must have been 3000+ pages on LBJ.  The good news:  What a fascinating read.  LBJ was probably (with the possible exception of Jefferson) the most complex character to ever hold the office.  Also, I’d say that both Volumes 3 and 4 stand alone as interesting books on their own – Volume 3 as a braoder history of the Senate and Civil Rights; Volume 4 as a slice of time around Kennedy’s assassination and Johnson’s assumption of power.  The bad news:  I got to the end of Vol 4 and realized that there’s a Vol 5 that isn’t even published yet.

That’s it for summer reading…now back to school!

It’s good that my friend Brad Feld‘s new book (co-authored by Dave Jilk, who I’ve also known on and off over the years), is divided into 52 chapters and is designed as a bit of a devotional, to be read one chapter per week.

Each chapter of The Entrepreneur’s Weekly Nietzsche: A Book for Disruptors is, as the authors write in the Introduction, worth “chewing on a while.” The structure of the book is laid out as:

The book contains fifty-two individual chapters (one for each week) 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.

That structure is perfect for me. I did ok in Philosophy classes, but I wouldn’t say it was my preferred subject. So the fact that Brad and Dave turned every Nietzsche quote into plain English before applying it to entrepreneurship and disruption was a welcome tactic to make the book as accessible as possible.

I wrote one of the essays in the book on creating a Company Operating System, which is in the chapter called “Doing is not Leading.” It’s an honor to be included as a contributor alongside a number of awesome CEOs, including Reid Hoffman, Ingrid Alongi, Daniel Benhammou, Sal Carcia, Ben Casnocha, Ralph Clark, David Cohen, Mat Ellis, Tim Enwall, Nicole Glaros, Will Herman, Mike Kail, Luke Kanies, Walter Knapp, Gary LaFever, Tracy Lawrence, Jenny Lawton, Seth Levine, Bart Lorang, David Mandell, Jason Mendelson, Tim Miller, Matt Munson, Ted Myerson, Bre Pettis, Laura Rich, Jacqueline Ros, and Jud Valeski.

In his Foreword, Reid Hoffman connects the dots perfectly:

Returning to Nietzsche, let’s examine why he in particular is such an apt patron philosopher for entrepreneurs. Nietzsche was rebelling against a stultifying philosophical practice that exalted the past—specifically the ideals and images of former thinkers and former leaders. He wanted to refocus on the now, on what humanity was and what it could become. As part of his rebellion, Nietzsche philosophized with a hammer: he wanted to destroy the old mindsets that locked people into the past, and thus better equip them to embrace the possibility of the new. Nietzsche’s desire to shift mindsets is also why he emphasized new styles of argument. Whereas most philosophers would typically open an argument in a classical form or by reviewing a historical great, Nietzsche would lead with an arresting aphorism or a completely new mythological narrative. He was, above all else, a disruptor of pieties and convention, always in search of new and original ways to be contrarian and right, never satisfied with the status quo. This is exactly the kind of mindset entrepreneurs should adopt. This is why a daily practice of philosophy can be the way that an entrepreneur moves from good to great. And, why a daily practice of Nietzsche is a great practice of philosophy for entrepreneurs.

What I love about the book is that you can read any given chapter at any time without having to read it front to back, and the combination of Nietzsche and entrepreneur essays makes the topics come to list. Pick one — they are organized into five sections, Strategy, Culture, Free Spirits, Leadership, and Tactics — and you’re sure to get both something chewy (e.g, thoughtful) and delicious (e.g., practical).

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.

I haven’t done a book review yet on this blog because I haven’t found a very relevant one. I will do more as I go here — I’ve actually read a few pretty useful business books lately — but there’s no better book to kick off a new category of postings here than the one I just finished: The MouseDriver Chronicles: The True-Life Adventures of Two First-Time Entrepreneurs.

The book details how two freshly-minted Wharton MBAs skipped the dot com and investment banking job offers to start a two-person company that produced the MouseDriver (a computer mouse shaped like a the head of a golf club) back in 1999-2000. It’s a great, quick read and really captures the spirit of much of what I’m trying to do with this blog, which is talk about first-time CEO issues, or company leadership/management issues in general.

Although it’s not about an internet business, the book also has an interesting side story, which is the powerful impact that email had on the MouseDriver business, with an email newsletter the entrepreneurs started that developed great readership and ultimately some viral marketing. Sort of like a blog, circa 1999.

Thanks to Stephanie Miller at Return Path for giving me the book!