In 2005, I wrote a post called Unfolding the Map in which I looked at these two seemingly opposing philosophies from successful entrepreneurs:

• If you don’t have a map, you can’t get lost
• If you don’t have a map, you can’t get where you’re going

and tried to combine them when thinking about product roadmapping. The same contradiction and combination could be applied to anything, including coaching and development.

That’s why I was excited to read my friend Matt Spielman’s new book, Inflection Points: How to Work and Live with Purpose. Matt worked at Return Path twice over the years — first as employee #3 (more on that in a minute) and then over a decade later as CMO. We live near each other and know each other’s families. I’ve been lucky enough to see his career unfold and develop into what it is today, a flourishing coaching business called Inflection Point Partners that helps clients tremendously…and that also feeds Matt’s soul.

When I first met Matt and he joined me and Jack to launch Return Path in 1999, he was fresh out of business school and focused on sales and marketing from his prior career in investment banking. Our idea was that he would do the same for us as we got our product in market. But as I started focusing more on what kind of company we wanted to build and how to get there, Matt became my leading thought partner on those topics. When we got to about 25 people, he and I created a new role for him — head of Human Capital and Organization Development. While a bit clunky, that title meant that Matt was the principal person helping me create at small scale what we later branded our People First philosophy. That philosophy and the practices we developed out of it led to 20 years of a strong track record of investing in people and helping over 1,300 colleagues grow their careers by being simple, actionable, and broad-based in the way we handled feedback and development planning. This started back in 2000.

Matt’s book puts the ethos that I saw percolating over 20 years ago into a tight framework around his coaching methodology of the GPS (Game Plan System). The book is short and sweet and walks through both the philosophy and the framework in accessible terms. And while it’s true that you have to be open to new ideas, open to serendipity, and go with flow sometimes…it’s also true that if you have specific goals in mind, you are unlikely to achieve them without a focused effort.

I’ve written a lot about coaching lately between The Impact of a Good Coach and another recent post about a strong coaching framework about intentionality in Russell Benaroya’s book. In that second post, I noted that “While I have become less and less of a life planner as I’ve gotten older under the headline of ‘man plans, God laughs,’ I am a huge believer in being intentional about everything. And that pretty much sums up Matt’s book: If you don’t have a map, you can’t get where you’re going.

Book Short: There is No Blueprint to $1B

Blueprint to a Billion: 7 Essentials to Achieve Exponential Growth, by David Thomson (book, Kindle) sounds more formulaic than it is. It’s not a bad book, but you have to dig a little bit for the non-obvious nuggets (yes, I get that growing your company to $1B in sales requires having a great value proposition in a high growth market!). The author looked for commonalities among the 387 American companies that have gone public since 1980 with less than $1B in revenues when they went public and had more than $1B in revenue (and were still in existence) at the time of the book’s writing in 2005.

Thompson classifies the blueprint into “7 Essentials,” which blueprint companies do well on across the board. The 7 Essentials are:

– Create and sustain a breakthrough value proposition

– Exploit a high growth market segment

– Marquee/lighthouse customers shape the revenue powerhouse

– Leverage big brother alliances for breaking into new markets

– Become the masters of exponential returns

– The management team: inside-outside leadership

– The Board: comprised of essentials experts

As I said above, there were some nuggets within this framework that made the entire read worthwhile. For example, crafting a Board that isn’t just management and investors but also includes industry experts like customers or alliance partners is critical. That matches our experience at Return Path over the years (not that we’re exactly closing in on $1B in revenues – yet) with having outside industry CEOs sit on our Board. Our Board has always been an extension of our management and strategy team, but we have specifically gotten some of our most valuable contributions and thought-provoking dialog from the non-management and non-investor directors.

Another critical item that I thought was interesting was this concept of not just marquee customers (yes, everyone wants big brand names as clients), but that they also need to be lighthouse customers. They need to help you attract other large customers to your solution – either actively by helping you evangelize your business, or at least passively by lending their name and case study to your cause.

The book is more of a retrospective analysis than a playbook, and some of its examples are a bit dated (marveling at Yahoo’s success seems a bit awkward today), and the author notes as well that many of the “blueprint” companies faltered after hitting the $1B mark. But it was a good read all-in. What I’d like to see next is a more microscopic view of the Milestones to $100 Million!

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:  I Wish This Existed 12 Years Ago

Brad Feld has been on my board for over a decade now, and when he and his partner Jason Mendelson told me about a new book they were writing a bunch of months ago called Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist, I took note.  I thought, “Hmmm.  I’d like to be smarter than my lawyer or venture capitalist.”

Then I read an advanced copy.  I loved it.  At first, I thought, I would really have benefited from this when I started Return Path way back when.  Then as I finished reading it, I realized it’s just a great reference book even now, all these years and financings later.  But as much as I enjoyed the early read, I felt like something was missing from the book, since its intended audience is entrepreneurs.

Brad and Jason took me up on my offer to participate in the book’s content a little bit, and they are including in the book a series of 50-75 sidebars called “The Entrepreneur’s Perspective” which I wrote and which they and others edited.  For almost every topic and sub-topic in the book, I chime in, either building on, or disagreeing, with Brad and Jason’s view on the subject.

The book is now out.  As Brad noted in his launch post, the book’s table of contents says a lot:

1. The Players
2. How to Raise Money
3. Overview of the Term Sheet
4. Economic Terms of the Term Sheet
5. Control Terms of the Term Sheet
6. Other Terms of the Term Sheet
7. The Capitalization Table
8. How Venture Capital Funds Work
9. Negotiation Tactics
10. Raising Money the Right Way
11. Issues at Different Financing States
12. Letters of Intent – The Other Term Sheet
13. Legal Things Every Entrepreneur Should Know

Fred has posted his review of the book as well.

Bottom line:  if you are an aspiring or actual entrepreneur, buy this book.  Even if you’ve done a couple of financings, this is fantastic reference material, and Brad and Jason’s points of view on things are incredibly insightful beyond the facts.  And I hope my small contributions to the book are useful for entrepreneurs as well.

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!)

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!

Boards That Lead, by Ram Charan, Dennis Carey, and Michael Useem, was recommended to me by a CEO Coach in the Bolster network, Tim Porthouse, who said he’s been referring it to his clients alongside Startup Boards. I don’t exactly belong in the company of Ram Charan (Brad and Mahendra probably do!), so I was excited to read it. While it’s definitely the “big company” version to Startup Boards, there are some good lessons for startup CEOs and founder to take away from it.

The best part about the book as it relates to ALL boards is the framework of Partner, Take Charge, Stay out of the Way, and Monitor. You can probably lump all potential board activities into these four buckets. If you look at it that way…these are pretty logical:

• Monitor – what you’d expect any board to do
• Stay out of the Way – basic execution/operations
• Partner – strategy, goals, risk, budget, leadership talent development
• Take Charge – CEO hiring/firing, Exec compensation, Ethics, and Board Governance itself.

There was an interesting nugget in the book as well called the Central Idea that I hadn’t seen articulated quite this way before. It’s basically a statement of what the business is and how it’s going to win. It’s about a page long, 8-10 bullet points, and it includes things like mission, strategy, key goals, and key operating pillars that underlie the goals. It basically wraps up all of Lencioni’s key questions in one page with a little more meat on the bones. I like it and may adopt it. The authors put the creation of the Central Idea into the Take Charge bucket, but I’d put it squarely in the Partner bucket.

Other than that, the book is what you’d expect and does have a lot of overlap with the world of startups. Its criteria for director selection are very similar to what we use at Bolster, as is its director evaluation framework. The book has a ton of handy checklists as well, some of which are more applicable than others to startups, for example Dealing with Nonperforming Directors and Spotting a Failing CEO.

All in, a good read if you’re a student of Boards.

Book Shorts:  One Up, One Down

I read new books by two of my favorite authors today:  Geoffrey Moore and Seth Godin.  Moore’s was his best book in years; Godin’s was his worst.

Geoffrey Moore’s latest book, Dealing with Darwin:  How Great Companies Innovate at Every Phase of their Evolution, is Moore’s best book in a while. While I loved Crossing the Chasm and thought Inside the Tornado was a close second, both The Gorilla Game and Living on the Fault Line didn’t do it for me — they both felt like a pile of Silicon Valley buzzwords as opposed to the insightful and groundbreaking market definition in his first two books.

But Darwin is a gem. It goes back to Moore’s strengths in analyzing leading companies and creating a powerful framework for innovation that transcends industry and stage of company. And even better, the book has a few very useful “how to” lists to help readers interpret the content and adapt it to their own environments.

So whether you’re a Geoffrey Moore fan or not — assuming you are a fan of innovation and kicking your competitors’ collective butts — this book’s for you.

By contrast, Seth Godin’s Small Is the New Big is old news if you are a Seth Godin fan. It is literally a repackaging of essays, articles, and blog postings he’s written over the years. He’s trended down lately in his writing, like Moore (and most authors who have a single theme or two, it should be said), but unlike Moore, this book isn’t his recovery. The book is a must-have if you (a) love Seth’s writing and want a hard copy archive of his soft-copy stuff, (b) you don’t read Seth’s blog and want to see what you’ve been missing, or (c) you have his other books and are compulsive enough that you can’t stand incomplete collections.

Otherwise, wait for his next book, which hopefully will have some more of the original thinking and writing and ideas that made books like Permission Marketing, Unleashing the Ideavirus, and Purple Cow such new business classics.  I have to say, the thing that disappointed me most here is that I felt like Seth totally sold out with this book — as a regular reader of his, I just felt duped by the Godin Marketing Machine, which is precisely the kind of thing he rants against.  There was definitely NO Free Prize Inside this one.

Book Short:  Tales of Two Cities

Return Path is basically dual-headquartered in New York City and Broomfield, Colorado, so two recently published books which provide history and insights into the tech industry in those two cities were both of interest to me.

Startup Communities: Building an Entrepreneurial Ecosystem in Your City, by Brad Feld (book, kindle) came out a few months ago and is part of Brad’s Startup Revolution series which will also include my upcoming book Startup CEO, to be published this fall.  In the book, Brad uses the example of the Boulder/Denver area and a few different sectors to demonstrate a blueprint to creating an entrepreneurial ecosystem – the kind that are popping up all over the world of late.

Tech and the City: The Making of New York’s Startup Community, by Alessandro Piol (kindle only) hits on many of the same themes and topics as they relate to New York City, although the book is more of a history of the New York tech scene than a framework with examples.  The book draws heavily on quotes from Fred Wilson, like Brad, a long time friend and Board member.  One of the things the book left me thinking about was what the New York tech scene will look like in 30 years after the new Cornell-Technion campus is up and running.  That plus the current momentum of the tech industry in New York, plus the sheer commercial scale of the city, could really produce an interesting environment down the road that actually starts to rival Silicon Valley, though rival probably isn’t the right word.

All in, these two books do a good job of chronicling the industry I work in, in the two cities where I work, but they also abstract nicely to broader principles about public-private collaboration as well as sector development.

Book Short:  Fixing America

I usually only blog about business books, but since I occasionally comment on politics, I thought I would also post on That Used to be Us:  How America Fell Behind in the World It Invented and How We Can Come Back, by Tom Friedman and Michael Mandelbaum (book, Kindle), which I just finished.

There is much that is good about America.  And yet, there is much that is broken and in need of serious repair.  I wrote about some thought on fixing our political system last year in The Beginnings of a Roadmap to Fix America’s Badly Broken Political System?, but fixing our political system can only do so much.  Tom Friedman, with whom I usually agree a lot, but only in part, nailed it in his latest book.  Instead of blaming one party or the other (he points the finger at both!), he blames our overall system, and our will as a people, for the country’s current problems.

The authors talk about the four challenges facing America today – globalization, the IT revolution, deficits and debt, and rising energy demand and climate change, and about how the interplay of those four challenges are more long term and less obvious than challenges we’ve faced as a country in the past, like World Wars or The Great Depression, or even The Great Recession.  The reason, according to the authors, that we have lost our way a bit in the last 20-40 years, is that we have strayed from the five-point formula that has made us successful for the bulk of our history:

• Providing excellent public education for more and more Americans
• Building and continually modernizing our infrastructure
• Keeping America’s doors to immigration open
• Government support for basic research and development
• Implementation of necessary regulations on private economic activity

It’s hard not to be in violent agreement with the book as a normal person with common sense.  Even the last point of the five-point formula, which can rankle those on the right, makes sense when you read the specifics.  And the authors rail against excessive regulation enough in the book to give them credibility on this point.

The authors’ description of the labor market of the future and how we as a country can be competitive in it is quite well thought through.  And they have some other great arguments to make – for example, about how the prior decade of wars was, for the first time in American history, not accompanied by tax increases and non-essential program cuts; or about how we can’t let ourselves be held hostage to AARP and have “funding old age” trump “funding youth” at every turn.

The one thing I disagree with a bit is the authors’ assertion that “we cannot simply cut our way to fiscal sanity.”  I saw a table in the Wall Street Journal the same day I was reading this book that noted the federal budget has grown from $2.6T in 2007 to $3.6T today – 40% in four years!  Sure sounds to me like mostly a spending program, though I do support closing loopholes, eliminating subsidies, and potentially some kind of energy tax for other reasons.

I’ll save their solution for those who read the book.  It’s not as good as the meat of the book itself, but it’s solid, and it actually mirrors something my dad has been talking about for a while now.  If you care about where we are as a country and how we can do better, read this book!

Book Short:  A Good Dose of Introspection

I rarely blog about non-business books since this is a business blog — and I read a lot of them!  But occasionally, one manages to slip in, and this time, it’s The Five People You Meet in Heaven, by Mitch Albom.  From the author of Tuesdays With Morrie, which I also liked quite a bit, this one is excellent.  And a very, very quick read.

The book, in short (i.e., a book short <g>), is about a guy who dies, and who, in heaven, meets five people who have shaped his life and died before him.  Some he knows well, some he knows barely, some he’s never met.  Each one tells him a story that explains some part of his life to him and in doing so, helps him understand more about himself and why/how he lived on earth.

The book, as I said, is a short read.  But more than that, it’s a wonderful story and provides an opportunity for a structured moment of introspection, one that I found very valuable.  Quite frankly, this book should be a “once every year or two” read.