Book Short: Continuing to make “sustainability” a mainstream business topic
Book Short: Continuing to make “sustainability” a mainstream business topic
The Big Pivot: Radically Practical Strategies for a Hotter, Scarcer, and More Open World, by my friend Andrew Winston, is a great book. It just got awarded one of the Top 10 business books of 2014 by Strategy+Business, which is a great honor.
Andrew builds nicely on his first book, Green to Gold: How Smart Companies Use Environmental Strategy to Innovate, Create Value, and Build Competitive Advantage (post, book link) (and second book, which I didn’t review, Green Recovery), as I said in my review of Green to Gold, to bring:
the theoretical and scientific to the practical and treat 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.
Andrew’s central thesis, with plenty of proof points in the book for our planet of 7 Billion people, rapidly heading to 9-10 Billion, is this:
Whether you take a purely fiscal view of these challenges or look through a human-focused lens, one thing is clear: we’ve passed the economic tipping point. A weakening of the pillars of our planetary infrastructure— a stable climate, clean air and water, healthy biodiversity, and abundant resources— is costing business real money. It’s not some futuristic scenario and model to debate, but reality now, and it threatens our ability to sustain an expanding global economy… If this hotter, scarcer, more transparent, and unpredictable world is the new normal, then how must companies act to ensure a prosperous future for all, including themselves?
Andrew’s writing is accessible and colorful. The book is full of useful analogies and metaphors like this one:
Climate can also seem easy to write off because the warming numbers don’t sound scary. A couple degrees warmer may sound pleasant, but we’re not really talking about going from 75 to 77 degrees Fahrenheit on a nice spring day. As many others have pointed out, the right metaphor is a fever. Take your core body temperature up one degree, and you don’t feel so great. Five degrees, and you’re sick as a dog. Ten degrees, and you’re dead.
The book also does a really nice job of looking at the externalities of climate change in a different way. Not the usual “I can pollute, because there’s no cost to me to doing so,” but more along the lines of “If I had to pay for all the natural resources my business consumes, I would treat them differently.”
Some of Andrew’s points are good but general and maybe better made elsewhere (like the problems of short-termism on Wall Street), but overall, this book is a great think piece for all business leaders, especially in businesses that consume a lot of natural resources, around how to make the challenge of climate change work for your business, not against it.
Two things occurred to me during my read of The Big Pivot that I think are worth sharing for the people in my life who still don’t believe climate change is real or threatening. The first is Y2K. Remember the potentially cataclysmic circumstance where mission critical systems all around the world were going to go haywire at midnight at the turn of the millennium? The conventional wisdom on why nothing major went wrong is that society did enough work ahead of time to prevent it, even though the outcomes weren’t clear and no one system problem alone would have been an issue. I was thinking about this during the book…and then Andrew mentioned it explicitly towards the end.
The second is something I read several years ago in my personal news bible, The Economist. I couldn’t find the exact quote online just now, but it was something to the effect of “Even if you don’t believe man created climate change, or that climate change is real and imperiling to humanity and can be fixed by man, the risks of climate change are so great, the potential consequences so dire, and the path to solve the problem so lengthy and complex and global…it’s worth investing in that solution now.”
Let’s all pivot towards that, shall we? If you want to download the introduction to the book for free, you can find it on Andrew’s web site. Or for a three-minute version of the story, you can watch this whiteboard animation on YouTube.
Book Short: Hire Great
Book Short: Hire Great
It’s certainly not hiring season for most of America The World The Universe, but we are still making some limited hires here at Return Path, and I thought – what better time to retool our interviewing and hiring process than in a relatively slow period?
So I just read Who: The A Method for Hiring, by Geoff Smart and Randy Street. It’s a bit of a sequel, or I guess more of a successor book, to the best book I’ve ever read about hiring and interviewing, Topgrading, by Geoff Smart and his father Brad (post, link to buy). This one wasn’t bad, and it was much shorter and crisper.
I’m not sure I believe the oft-quoted stat that a bad hire costs a company $1.5mm. Maybe sometimes (say, if the person embezzles $1.4mm), but certainly the point that bad hires are a nightmare for an organization in any number of ways is well taken. The book does a good job of explaining the linkage from strategy and execution straight to recruiting, with good examples and tips for how to create the linkage. That alone makes it a worthwhile read.
The method they describe may seem like common sense, but I bet 95 out of 100 companies don’t come close. We are very good and quite deliberate about the hiring process and have a good success average, but even we have a lot of room to improve. The book is divided into four main sections:
- Scorecard: creating job descriptions that are linked to company strategy and that are outcome and competency based, not task based
- Sourcing: going beyond internal and external recruiters to make your entire company a talent seeker and magnet
- Selection: the meat of the book – good detail on how to conduct lots of different kinds of interviews, from screening to topgrading (a must) to focused to reference
- Sell: how to reel ’em in once they’re on the line (for us anyway, the least useful section as we rarely lose a candidate once we have an offer out)
One of the most poignant examples in the book centered around hiring someone who had been fired from his previous job. The hiring method in the book uncovered it (that’s hard enough to do sometimes) but then dug deep enough to understand the context and reasons why, and, matching up what they then knew about the candidate to their required competencies and outcomes for the job, decided the firing wasn’t a show-stopper and went ahead and made the hire.
I’d think of these two books the way I think about the Covey books. If you have never read The 7 Habits of Highly Effective People, you could just get away with reading Stephen Covey’s newer book, The 8th Habit: From Effectiveness to Greatness, though the original is much richer.
Book Short: Long on Platitudes, Short on Value
Book Short: Long on Platitudes, Short on Value
I approached Success Built to Last: Creating a Life That Matters, by Jerry Porras, Stewart Emery, and Mark Thompson, with great enthusiasm, as Porras was co-author, along with Jim Collins, of two of my favorite business books of all time, Built to Last and Good to Great. I was very disappointed in the end. This wasn’t really a business book, despite its marketing and hype. At best, it was a poor attempt at doing what Malcolm Gladwell just did in Outliers in attempting to zero in on the innate, learned, and environmental qualities that drive success.
The book had some reasonably good points to make and definitely some great quotes, but it was very rambly and hard to follow. Its attempt at creating an overall framework like the one used in Built to Last and Good to Great just plain didn’t work, as two of the three legs of the stool were almost incomprehensible, or to put it more charitably, didn’t hang together well.
This isn’t a terrible book to have on your shelf, and it might be good to skim, but remember that “skim” is only one letter away from “skip.”
Book Short: Loving the Strengths Movement More Than the Book
Book Short: Loving the Strengths Movement More Than the Book
I’m a big believer in the so-called Strengths Movement — that we would all be better served by playing to our strengths than agonizing over fixing our weaknesses. I think it’s true both in professional and personal settings.
The books written by Marcus Buckingham that come out of Gallup’s extensive research into corporate America, First, Break All the Rules (about management) and Now, Discover Your Strengths (self-management) are both quite good. Another book written by someone else off the same research corpus, 12: The Elements of Great Managing is ok, but not as good, as I wrote about here.
Buckingham’s newest, Go Put Your Strengths to Work: 6 Powerful Steps to Achieve Outstanding Performance, is fine and has some good points but is way too long, a little hokey, and has a lot of online companion material that is far more interesting sounding than it is actually useful.
The book does build nicely on Now, Discover Your Strengths by giving you inspiration and a framework for taking those signature themes from the prior book and translating them into action — stuff you actually do every day that plays to your strengths and draws out your weaknesses. And that’s helpful. Some of his suggestions for what you do with that information are ok but a bit common sense only and way too drawn out (“here’s how to talk to your boss…”).
To be fair, I am going to do some of the work that Buckingham recommended doing — so I guess that says something about the power of the book, or at least the movement underlying it. But not the best read in the world.
Book Short: Loved Loved
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.

Book Short: A Twofer
Book Short: A Twofer
My friend Andrew Winston, who is one of the nation’s gurus in corporate sustainability, just published his second book, this one from Harvard Business Press — Green Recovery: Get Lean, Get Smart, and Emerge from the Downturn on Top. It builds on the cases and successes he had with his first book, Green to Gold (post, link to book), which came out a couple years ago and has become the standard for how businesses embrace sustainability and use it to their financial and strategic competitive advantage rather than thinking of it as a burden or a cost center.
Green Recovery is a shorter read (my kind of business book), and it hits a few key themes:
-
Going green not only shouldn’t wait for better economic times, it’s a key way out of this mess
- Businesses have relied on layoffs to cut costs for far too long — it’s time to get lean on stuff, not people
- This is about survival for many businesses: Detroit died because it missed the green wave of environmental interest and rising energy prices
- And the overarching theme…Green doesn’t raise costs, it lowers them – it’s a source of profit and innovation
The book reminds me a lot of my post Living With Less, For Good, which I wrote at the beginning of the financial market freefall last fall, talking about how we as a company were figuring out how to cut back without cutting people (something we’ve managed to do). Although I wasn’t talking about green initiatives specifically, the point of getting leaner on “stuff” really resonates with me.
At the end of the day, Andrew proves that steering your company to go green — no matter what industry you’re in — is a twofer: you can increase the strength of the business and simultaneously do your part to clean up the environment. That’s definitely the “change we can believe in” mentality applied quite pragmatically!
Book Short: Steve Jobs and Lessons for CEOs and Founders
Book Short: Steve Jobs and Lessons for CEOs and Founders
First, if you work in the internet, grew up during the rise of the PC, or are an avid consumer of Apple products, read the Walter Isaacson biography of Steve Jobs (book, kindle). It’s long but well worth it.
I know much has been written about the subject and the book, so I won’t be long or formal, but here are the things that struck me from my perspective as a founder and CEO, many taken from specific passages from the book:
- In the annals of innovation, new ideas are only part of the equation. Execution is just as important. Man is that ever true. I’ve come up with some ideas over the years at Return Path, but hardly a majority or even a plurality of them. But I think of myself as innovative because I’ve led the organization to execute them. I also think innovation has as much to do with how work gets done as it does what work gets done.
- There were some upsides to Jobs’s demanding and wounding behavior. People who were not crushed ended up being stronger. They did better work, out of both fear and an eagerness to please. I guess that’s an upside. But only in a dysfunctional sort of way.
- When one reporter asked him immediately afterward why the (NeXT) machine was going to be so late, Jobs replied, “It’s not late. It’s five years ahead of its time.” Amen to that. Sometimes product deadlines are artificial and silly. There’s another great related quote (I forget where it’s from) that goes something like “The future is here…it’s just not evenly distributed yet.” New releases can be about delivering the future for the first time…or about distributing it more broadly.
- People who know what they’re talking about don’t need PowerPoint.” Amen. See Powerpointless.
- The mark of an innovative company is not only that it comes up with new ideas first, but also that it knows how to leapfrog when it finds itself behind. This is critical. You can’t always be first in everything. But ultimately, if you’re a good company, you can figure out how to recover when you’re not first. Exhibit A: Microsoft.
- In order to institutionalize the lessons that he and his team were learning, Jobs started an in-house center called Apple University. He hired Joel Podolny, who was dean of the Yale School of Management, to compile a series of case studies analyzing important decisions the company had made, including the switch to the Intel microprocessor and the decision to open the Apple Stores. Top executives spent time teaching the cases to new employees, so that the Apple style of decision making would be embedded in the culture. This is one of the most emotionally intelligent things Jobs did, if you just read his actions in the book and know nothing else. Love the style or hate it – teaching it to the company reinforces a strong and consistent culture.
- Some people say, “Give the customers what they want.” But that’s not my approach. Our job is to figure out what they’re going to want before they do. I think Henry Ford once said, “If I’d asked customers what they wanted, they would have told me, ‘A faster horse!’” People don’t know what they want until you show it to them. That’s why I never rely on market research. Our task is to read things that are not yet on the page. There’s always a tension between listening TO customers and innovating FOR them. Great companies have to do both, and know when to do which.
- What drove me? I think most creative people want to express appreciation for being able to take advantage of the work that’s been done by others before us. I didn’t invent the language or mathematics I use. I make little of my own food, none of my own clothes. Everything I do depends on other members of our species and the shoulders that we stand on. And a lot of us want to contribute something back to our species and to add something to the flow. It’s about trying to express something in the only way that most of us know how—because we can’t write Bob Dylan songs or Tom Stoppard plays. We try to use the talents we do have to express our deep feelings, to show our appreciation of all the contributions that came before us, and to add something to that flow. That’s what has driven me. This is perhaps one of the best explanations I’ve ever heard of how creativity can be applied to non-creative (e.g., most business) jobs. I love this.
My board member Scott Weiss wrote a great post about the book as well and drew his own CEO lessons from it – also worth a read here.
Appropos of that, both Scott and I found out about Steve Jobs’ death at a Return Path Board dinner. Fred broke the news when he saw it on his phone, and we had a moment of silence. It was about as good a group as you can expect to be with upon hearing the news that an industry pioneer and icon has left us. Here’s to you, Steve. You may or may not have been a management role model, but your pursuit of perfection worked out well for your customers, and most important, you certainly had as much of an impact on society as just about anyone in business (or maybe all walks of life) that I can think of.
Book Short (and great concept): Moments of Truth
Book Short (and great concept): Moments of Truth
TouchPoints: Creating Powerdul Leadership Connections in the Smallest of Moments, by Douglas Conant, former CEO of Campbell’s Soup Corporation, and Mette Norgaard (book, kindle), is a very good nugget of an idea wrapped in lots of other good, though only loosely connected management advice around self awareness and communication — something I’m increasingly finding in business books these days.
It’s a very short book. I read it on the Kindle, so I don’t know how many pages it is or the size of the font, but it was only 2900 kindles (or whatever you call a unit on the device) and only took a few Metro North train rides to finish. It’s probably worth a read just to get your head around the core concept a bit more, though it’s far from a great business book.
I won’t spend a lot of time on the book itself, but the concept echoes something I’ve been referring to a while here at Return Path as “Moments of Truth.” Moments of Truth are very short interactions between you and an employee that are high impact and, once you get the hang of them, low effort. At least, they’re low effort relative to long form meetings.
Here are a few thoughts about Moments of Truth:
- They are critical opportunities to get things both very right and very wrong with an employee
- They are more powerful than meets the eye – both for what they are and because they get amplified as employees mention them to other employees
- They can come to you (people popping into your office and the like), you can seek them out (management by walking around), and you can institutionalize them (for example, one of the things I do is call every employee on their Return Path anniversary to congratulate them on the milestone)
- They are no different than any other kind of interaction you have, just a lot shorter and therefore can be more intense (and numerous)
- Their use cases are as broad as any management interaction — coaching, positive or negative feedback, input, support, etc.
What can you as a manager or leader do to perfect your handling of Moments of Truth?
First, learn how to spot them when they come to you, and think about a typical employee’s day/week/month/year to think about when you can find opportunities to seek them out. Their first day on the job. When they get a promotion. When they get a great performance review, or new stock options. Maybe when they get a poor performance review or denied a promotion they were seeking.
Second, learn to appreciate them and leave space for them. If you have zero free minutes in every single day, you not only won’t have time to create or seek out Moments of Truth, you’ll be rushed or blow them off when they come to you.
Finally, like everything else, you have to develop a formula for handling them and then practice that formula. The book does talk about a formula of “head, heart, hand” (e.g., being logical, authentic, and competent) that’s not bad. Although I’d never thought about it systematically before writing this post, I have a few different kinds of Moments of Truth, and each one has its own rhythm to it, and its own regular ending.
But regardless of how you handle them, once you think about your day through this lens, you’ll start seeing them all over the place. Recognize their power, and dive in!
Books
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.
Startup CXO: the Sequel to Startup CEO
As I finished up my work on the Second Edition of Startup CEO: A Field Guide to Scaling Up Your Business and started working on a new startup, my colleagues and I started envisioning a new book as a sequel or companion to Startup CEO that is going to be published on June 9 with our same publisher, Wiley & Sons. The book is called Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams.
Simply put, the first book left me with the nagging feeling that it wasn’t enough to only help CEOs excel, because starting and scaling a business is a collective effort. What about the other critical leadership functions that are needed to grow a company? If you’re leading HR, or Finance, or Marketing, or any key function inside a startup, what resources are available to you? What should you be thinking about? What does ‘great’ look like? What challenges lurk around the corner as you scale your function that you might not be focused on today? If you’re a CEO who has never managed all these functions before, what should you be looking for when you hire and manage all these people? If you’re an aspiring executive, from entry-level to manager to director, what do you need to think about as you grow your career and develop your skills?
Startup CXO is a “book of books,” with one section for each major function inside a company. Each section is be composed of 15-20 discrete short chapters outlining the key “playbooks” for each functional role in the company – Chief People Officer, Chief Financial Officer, Chief Marketing Officer, Chief Revenue Officer, etc., hence the title Startup CXO – which is a generally accepted label in the startup ecosystem for “Chief ____ Officer.”
Here are the front and back covers of the book, with some great endorsements we’re so proud of on the back.


This is an important topic to write about at this particular time because America’s “startup revolution” continues to gather steam. There are only increasing numbers of venture capital investors, seed funds, and accelerators supporting increasing numbers of entrepreneurial ventures. While there are a number of books in the marketplace about CEOs and leadership, and some about individual functional disciplines (lots of books about the topic of Sales, the topic of Product Development), there are very few books that are practical how-to guides for any individual function, and NONE that wrap all these functions into a compendium that can be used by a whole startup executive team. Very simply, each section of this book serves as a how-to guide for a given executive, and taken together, the book will be a good how-to guide for startup executive teams in general.
Startup CXO has my name on it as principal author, and I’m writing parts of it, but I can’t even pretend to write it on my own, so the book has a large number of contributors who have the experience, credibility, and expertise to share something of value with others in their specific functional disciplines — most of my Bolster co-founders are writing sections, and the others are being written by former Return Path executive colleagues — Jack Sinclair, Cathy Hawley, Ken Takahashi, Anita Absey, George Bilbrey, Dennis Dayman, Nick Badgett, Shawn Nussbaum, and Holly Enneking.
Startup CXO is also pretty closely related to Bolster’s business, since we are in the business of helping assess and place on-demand CXO talent, and as such, the final section of the book has a series of chapters written by Bolster members who are career Fractional Executives about their experience as a Fractional CXO.
The book is available for pre-order now at Amazon and Barnes & Noble.
Oh, and stay tuned for a third book in the series (kind of) due out late this year. More on that over the summer as the project takes shape!
Book Short: Triumph over Adversity
Book Short: Triumph over Adversity
In truth, Malcolm Gladwell’s most recent book, David and Goliath: Underdogs, Misfits, and the Art of Battling Giants, was a bit of a disappointment. I thought his first three books, Tipping Point, Blink, and Outliers, were fantastic, and I routinely refer to them in business. David and Goliath isn’t bad, it’s just a little light and hangs together a lot less than Gladwell’s other books.
I just read a scathing review of it in The New Republic, which I won’t bother linking to, mostly because the reviewer was on a total rant about Gladwell in general and was particularly insulting to people who read Gladwell (an interesting approach to a book review), essentially calling us self-help seekers who aren’t interested in reality or wisdom. Nice.
Two seminal quotes from the book that get at its essence are:
To play by David’s rules you have to be desperate. You have to be so bad that you have no choice.
and
He was an underdog and a misfit, and that gave him the freedom to try things no one else ever dreamt of.
Those things are probably generally true in life, but also applicable to business. A business book I read years ago called The Underdog Advantage: Using the Power of Insurgent Strategy to Put Your Business on Top, by David Morey and Scott Miller, brings this principle to life for work.
I also liked the concept Gladwell talked about a few times in the book about being a big fish in a small pond, and how that can sometimes be a better place to be than a small fish in a big pond in terms of building self-confidence. That’s certainly been true for me in my life.
If you go back the premise of Gladwell’s books in general, as I heard him say on The Daily Show the other night — “to get people to look at the world a little differently” — then David and Goliath does that on some level. And for that alone, it’s probably worth a quick read.