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: 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.
Book Short: Alignment Well Defined, Part II
Book Short: Alignment Well Defined, Part II
Getting the Right Things Done: A Leader’s Guide to Planning and Execution, by Pascal Dennis, is an excellent and extraordinarily practical book to read if you’re trying to create or reengineer your company’s planning, goal setting, and accountability processes. It’s very similar to the framework that we have generally adapted our planning and goals process off of at Return Path for the last few years, Patrick Lencioni’s The Advantage (book, post/Part I of this series). My guess is that we will borrow from this and adapt our process even further for 2014.
The book’s history is in Toyota’s Lean Manufacturing system, and given the Lean meme floating around the land of tech startups these days, my guess is that its concepts will resonate with most of the readers of this blog. The book’s language — True North and Mother Strategies and A3s and Baby A3s — is a little funky, but the principles of simplicity, having a clear target, building a few major initiatives to drive to the target, linking all the plans, and measuring progress are universal. The “Plan-Do-Check-Adjust” cycle is smart and one of those things that is, to quote an old friend of mine, “common sense that turns out is not so common.”
One interesting thing that the book touches on a bit is the connection between planning/goals and performance management/reviews. This is something we’ve done fairly well but somewhat piecemeal over the years that we’re increasingly trying to link together more formally.
All in, this is a good read. It’s not a great fable like Lencioni’s books or Goldratt’s classic The Goal (reminiscent since its example is a manufacturing company). But it’s approachable, and it comes with a slew of sample processes and reports that make the theory come to life. If you’re in plan-to-plan mode, I’d recommend Getting the Right Things Done as well as The Advantage.
Book Short: Blogging Alone?
Book Short: Blogging Alone?
I usually only blog about business books, but since I read Bowling Alone: The Collapse and Revival of American Community, by Robert Putnam, because of its connection to the topic of Internet community and social media, I’ll record some thoughts about and from it here.
It’s an interesting read, although a little long. Putnam’s basic thesis is that America’s social capital — the things that have brought us physically and emotionally together as a country throughout much of the 20th century such as church, voting, and participation in civic organizations like the PTA or the Elks Club — are all severely on the decline. The reasons in Putnam’s view are television (you knew all those re-runs of The Brady Bunch would eventually catch up to you), suburban sprawl, two-career families, and “generational values,” which is Putnam’s way of saying things like people in their 60s all read newspapers more than people in their 50s, who all read newspapers more than people in their 40s, etc. He believes the decline is leading to things like worse schools, less safe neighborhoods, and poorer health.
The book does a good job laying out the decline in social capital with some really interesting and somewhat stunning numbers, but the book’s biggest shortcoming is that Putnam doesn’t do the work to determine causation. I buy that there’s a correlation between less voting and less safe neighborhoods, for example, but the book doesn’t convince me that A caused B as opposed to B causing A, or C causing both A and B. What I really wanted at the end of the book was for Putnam to go mano-a-mano with the Freakonomics guy for a couple hours. Preferably in those big fake sumo suits.
The book was published in 2000, so probably written from 1997-1999, and therefore its treatment of the Internet was a little dated — so I found myself wanting more on that topic since so much of the social media revolution on the Internet is post-2004. His basic view of the Internet is that it is in fact a bright spot in the decline of community, but that it’s changing the nature of communities. Now instead of chatting with whoever is bowling in the next lane over at the Tuesday night bowling league on Main Street, we are in an online discussion group with other people who own 1973 BMW 2002 series cars, preferably the turbo-charged ones. So the micro-communities of the Internet circa 2000 are more egalitarian (“on the Internet, no one knows you’re a dog”), but more narrow as well around interests and values.
What has social media done to Putnam’s theories in the last seven or eight years? How have things like blogging, MySpace, LinkedIn, YouTube, and Photobucket changed our concept of community in America or in the world at large? I welcome your comments on this and will write more about it in the future.
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: New to the Canon of Great CEO Books
Please go put Decide and Conquer: 44 Decisions that will Make or Break All Leaders by David Siegel on your reading list, or buy it. David’s book is up there on my list with Ben Horowitz’s The Hard Thing About Hard Things. It’s a totally different kind of book than Startup CEO, and in some ways a much better one in that there’s a great through-line or storyline, as David shares his leadership framework in the context of his journey of getting hired to replace founder Scott Heiferman as Meetup’s CEO after its acquisition by WeWork, including some juicy interactions with Adam Neumann, through the trials and tribulations of WeWork as a parent company, through COVID and its impact on an in-person meeting facilitator like Meetup, through to the sale of Meetup OUT of WeWork.
It’s hard to do the book justice with a quick write up. It’s incredibly concise. It’s clear. It’s witty. Most of all, it’s very human, and David shares a very human, common sense approach to leadership. I particularly like a device he uses to reinforce his main points and principles by bolding the key phrases every time they show up in the book: be kind, be confident, be bold, expand your options, focus on the long-term picture, be pragmatic, be honest, be speedy, do what’s right for the business, work for your people and they’ll work for you, be surprised only about being surprised. These all resonate with me so much.
One of the interesting things about the book is that David is a CEO, but not a founder (although he was sort of a re-founder in this case). A lot of CEO books talk about how to run a company, or give stories from the trials and tribulations thereof, but few focus on the elements of interviewing for the CEO job, or taking over the reins of a company in the midst of a turbulent flight. So the book is about getting the job, starting the job, doing a turnaround, leading a company through growth, a buy-out, and managing a company inside of another company. And because Meetup is such an iconic brand and business, it’s easy to understand a lot of the backdrop to David’s story.
I just met David for the first time a few weeks ago. We knew a bunch of people in common from his DoubleClick days. We instantly hit it off and traded copies of our books, and then were reading them at the same time trading emails about the parts that clicked. I just can’t recommend the book enough to any CEO or founder. In my view, it joins a pretty elite canon.
Book Short: Must-Read for CXOs
Lead Upwards: How Startup Joiners Can Impact New Ventures, Build Amazing Careers, and Inspire Great Teams, by Sarah E. Brown, is an amazing book – and one that fits really well with our Startup Revolution series, in particular our book Startup CXO.
I kept thinking as I was reading it that it was the other side of the proverbial coin…that Startup CXO was about the details of each executive job in a company…but Sarah’s book is about the things common to ALL executive jobs – how to get them, how to succeed at them, essentially how to BE an executive. I read it front to back in a single day one weekend and loved it.
Some of the most insightful moments in her book are:
- Why big company executives who join startups often struggle
- How to get promoted by proactively doing the next job – act “as if” – while still excelling at your current job
- The importance of managing to the CEO’s preferred work style (personally…I’d debate this – I think CEO’s should manage to their CXOs’ work styles or at least make it a two-way street, but her point is very valid!)
- Why executives shouldn’t just up and quit with “two weeks’ notice” but that executives also need to be mentally prepared to be shown the door when they resign
- The importance of getting your hands dirty and not being “above” doing the work of your team
- Mastering the art of data-driven storytelling
Sarah quotes a number of CEOs throughout the book who I know and respect, from Nick Mehta at Gainsight to Mindy Lauck at Broadly. It was fun to read the book and see a number of very familiar names in it along the way.
Sarah and I did an interesting format – sort of a “dueling fireside chat” about our respective books on a webinar last fall. We had a fantastic conversation that could have gone on for hours. If you’re an executive – or an aspiring executive – you should go read her book.
Book Short: On Employee Engagement
Book Short: On Employee Engagement
The first time I ever heard the term “Employee Engagement” was from my colleague David Sieh, one of the better managers I’ve ever worked with. He said it was his objective for his engineering team. He explained how he tried to achieve it. I Quit, But forgot to Tell You, by Terri Kabachnick, is a whole book on this topic, a very short but very potent one (the best kind of business books, if you ask me).
It’s got all the short-form stuff you’d expect…a checklist of reasons for disengagement, an engagement quiz, the lifecycle of an employee that leads to disengagement, rules for dealing as a manager.
But beyond the practical, the book serves as a good reminder that employee engagement is the key to a successful organization, no matter what industry you’re in. All managers at Return Path — this is on the way to your desk soon!
Book Short: Getting to MVP
Book Short: Getting to MVP
Usually, when we hear the term MVP, we think Most Valuable Player. But in my line of work, that acronym has come to mean something entirely different: Minimum Viable Product. Running Lean: Iterate from Plan A to a Plan That Works, by Ash Maurya, is an incredibly useful, practical how-to guide for any entrepreneur with an idea from concept through to MVP, or the smallest bit of functionality that you can get customers to pay for. This is one of the best books I’ve read that encapsulates most of the contemporary thinking and writing about product development in the early stages of a startup’s life from thought leaders like Steven Gary Blank and Eric Ries.
I read the book recently, as I was writing Startup CEO (original outline here), and I quoted liberally from it, including using his Lean Canvas graphic:
The basic principle behind the Lean Canvas is that the old way of doing a business plan was a ton of up front planning work, assuming you’re right, then building to spec. The new way of doing a business plan is a really short series of hypotheses on a single page, then the time is spent de-risking the plan by systematically testing each element of it out. The book includes several lists of checklists that walk you through how to test each box on the Lean Canvas. As I’ve written about before, checklists are a really powerful management tool.
This is an essential read for entrepreneurs just starting a business. But it’s also an excellent read for anyone running a growth company. We have adopted more and more agile/lean methodologies over time at Return Path, and all of our product teams use the Lean Canvas with any major new features and projects.
(Side note – I’m writing this post on Friday, May 10, which is the 9th anniversary of my publishing this blog – 760 posts and one draft book later, it’s still an integral part of my business life!)
Book Short: Gladwell Lite
Book Short: Gladwell Lite
What the Dog Saw, And Other Adventures (book, Kindle) is Malcolm Gladwell’s latest book. Unlike his three other books, which I quite enjoyed:
- The Tipping Point (about how trends and social movements start and spread)
- Blink (about how the mind makes judgments)
- Outliers: The Story of Success (about how talents are genetic, situational, and cultivated)
this was not a complete book, but rather a compendium of his New Yorker articles loosely grouped into three themes.
If you love Gladwell and don’t read The New Yorker, it’s not a bad read. He’s a fantastic writer, and his vignettes are interesting. There are many “hmmm” moments as we learn why ketchup always tastes the same but mustard doesn’t; why Ron Popeil is a great salesman of kitchen gadgets; or why the inventor of the birth control pill thought the Pope would endorse it. But it falls far short of his three books, which go deep into topics and leave a much more lasting impression/impact.
Book Short: The Joys of Slinging Hash
Book Short: The Joys of Slinging Hash
Patrick Lencioni’s The Three Signs of a Miserable Job is a good read, as were his last two books, The Five Temptations of a CEO (post, link), and The Four Obsessions of an Extraordinary Executive (post, link). They’re all super short, easy reads (four express train rides on Metro North got the job done), with a single simple message and great examples. This one is probably my second favorite so far.
This book, which has a downright dreary title, is great. It points to and proposes a solution to a problem I’ve thought about for a long time, which is how do you create meaning for people in their day to day work when they’re not doing something intrinsically meaningful like curing a disease or feeding the homeless. His recipe for success is simple:
– Get people to articulate the relevance in their jobs…the meaning they derive out of their work…an understanding of the people whose lives are made better, even in small ways, by what they do every day
– Get people to measure what they do (duh, management 101), IN RELATION TO THE RELEVANCE learnings from the last point (ahh, that’s an interesting twist)
– Get to know your people as people
All of these are things you’d generally read in good books on management, but this book ties them together artfully, simply, and in a good story about a roadside pizza restaurant. It also stands in stark contrast to the book I reviewed and panned a few days ago by Jerry Porras in that it is nothing but examples from non-celebrities, non-success stories — ordinary people doing ordinary jobs.
Brad has blogged glowingly about Death by Meeting, so I’ll probably make that my next Lencioni read next month, with two more to go after that.