Book Short:  Internet Fiction, part II

I hate to write a lame post, but here’s what I wrote earlier in the year about Eliot Peper’s first Internet thriller, Uncommon Stock:

Eliot Pepper’s brand new startup thriller, Uncommon Stock, was a breezy and quick read that I enjoyed tremendously. It’s got just the right mix of reality and fantasy in it. For anyone in the tech startup world, it’s a must read. But it would be equally fun and enjoyable for anyone who likes a good juicy thriller.

Like my memory of Hackoff, the book has all kinds of startup details in it, like co-founder struggles and a great presentation of the angel investor vs. VC dilemma. But it also has a great crime/murder intrigue that is interrupted with the book’s untimely ending.  I eagerly await the second installment, promised for early 2015.

Having just finished that second installment, called Uncommon Stock: Power Play, basically I want to say “ditto.”  Power Play was just as good as the first book, and now I can’t wait for the third. Where the first installment’s startup focus was around funding and founder dynamics, this one’s startup focus was around shipping product and customers. The thriller part was just as juicy.

It’s also kind of fun reading about the Boulder startup scene, especially from a writer who doesn’t and who has never spent a ton of time there. He gets some things remarkably accurate with crisp descriptions. I was kind of hoping for a cameo by Brad, at least in the form of a throw-away comment about the “long haired homeless-looking investor in the corner of Frasca.”

Book Short:  Catchiest Title in a Long Time

You have to admit, a book called The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich has a pretty enticing title.  The email geek in me thinks that if it were a subject line, it would have a good open rate.  Anyway, the book, by Timothy Ferriss, is a breezy read that  blends self help with entrepreneurship, has a lot of good resource lists in it, and is worth reading  if you don’t take it too  seriously.

There are some good central points to the book.  First, life has changed, and people don’t want to slave away until they’re 65 any more so they can do all the fun stuff in their old age — they want to change directions, unplug more regularly, and enjoy life with their families when they’re younger.  I buy that.
Second, good companies are increasingly allowing employees more degrees of freedom in the where and when and even how of getting things done, just as long as they get things done — and people should take advantage of that.  I buy that as well — we practice that at Return Path, generally speaking.  Third, startups that are mainly virtual organizations and internet-based are easier, cheaper, and potentially more profitable than most businesses have been, historically speaking.  Ok, fair enough.

Fourth, anyone can be just like the author and do all of this stuff, too, right?  Start a business that turns into a cash machine that requires little to no maintenance while becoming one of the best tango dancers in the world in South America, etc. etc. etc.  Well, maybe not.  I guess the point of self-help books is to show an extreme example and inspire people to achieve it, and I do think there’s a lot to what Ferriss says about how people can live richly without being rich, but the fact is that the world would fall apart if everyone did what he does.  And the other fact is that Ferriss is well above average in intellect and drive, and probably some physical talents as well from his descriptions of tango dancing and kick boxing, which must contribute to his success in life far more than his operating philosophy does.

But as I said, it’s a fun read, and if you don’t take it too seriously, or at least take the feedback directionally as opposed to whole hog, it’s well worth it.

Book Short:  Worth Buying Free

The cynic in me wanted to start this book review of  Free: The Future of a Radical Price, by Chris Anderson, by complaining that I had to pay for the book.  But it ended up being good enough that I won’t do that (plus, the author said there are free digital versions available — though the Kindle edition still costs money).  At any rate, a bunch of reviews I read about the book panned it when compared to Anderson’s prior book, The Long Tail (post, link to book).

I won’t get into the details of the book, though you’ll get an idea from the paragraph below, but Anderson has a few gems worth quoting:

• Any topic that can divide critics into two opposite camps — “totally wrong” and “so obvious” — has got to be a good one
• Free makes Paid more profitable
• Younger players have more time than money…older players have more money than time
• Doing things we like without pay often makes us happier than the work we do for a salary
• It’s true that each generation takes for granted some things their parents valued, but that doesn’t mean that generation values everything less
  

While Free is s probably not quite as good as The Long Tail, it does a good job of organizing and classifying and explaining the power of different economic models that involve a free component, and I found it very thought provoking about our own business at Return Path.

We already do a couple forms of Free — we practice the “third party” model, by giving things away to ISPs but selling them to mailers; and we practice Freemium by providing Senderscore.org and Feedback Loops for free in order to attract paying customers to our testing and monitoring application and whitelist.  But could we do others?  Maybe.  They may not be revolutionary, but they’re smart marketing.

As some of the reviewers write, the book isn’t the be-all-end-all of marketing, it overreaches at times, and it is more applicable to some businesses than others, but Free was definitely worth paying for.

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!

Book Short: What’s For Dinner Tonight, Honey?

The Paradox of Choice: Why More is Less, by Barry Schwartz, presents an enlightening, if somewhat distressing perspective on the proliferation of options and choices facing the average American today. The central thesis of the book is that some choice is better than no choice (I’d rather be able to pick blue jeans or black jeans), but that limited choice may be better in the end than too much choice (how do I know that the jeans I really want are relaxed cut, tapered leg, button fly, etc.?). We have this somewhat astonishing, recurring conversation at home every night, with the two of us sitting around paralyzed about where to eat dinner.

The author’s arguments and examples are very interesting throughout, and his “Laffer curve” type argument about choice vs. too much choice rings true. While there’s obviously no conclusive proof about this, the fact that our society is more rife with depression than ever before at least feels like it has a correlation with the fact that most of us now face a proliferation of choices and decisions to make exponentially more than we used to. The results of this involve ever-mounting levels of regret, or fear of regret, as well as internal struggles with control and expectations. Perhaps the best part of the book is the final chapter, which ties a lot of the material of the book together with 11 simple suggestions to cope better with all the choices and options in life — summed up in the last few words of the book suggestions that “choice within constraints, freedom within limits” is the way to go. Amen to that. We all need some basic structure and frameworks governing our lives, even if we create those constructs ourselves. The absence of them is chaos.

Overall, this is a good social science kind of read, not overwhelming, but definitely interesting for those who are students of human psychology, marketing, and decision making. It’s squarely in the genre of Gladwell’s The Tipping Point and Blink, and Robert Cialdini’s Influence, most of which I’ve written about recently, and though not as engaging as Gladwell, worth a read on balance if you like the genre.

Thanks to my friend Jonathan Shapiro for this book.

Book Short:  Deep Dive on Customer Development

I continue to be on a tear reading books about startups as I finish and get ready for the publication of Startup CEO (now available for pre-ordering at Amazon).   This week’s selection was The Startup Owners Manual:  A Step-by-Step Guide for Building a Great Company, by Steve Blank and Bon Dorf.  This book is a significantly more detailed version of Blank’s first book, The Four Steps to the Epiphany, which was a revolutionary book a few years ago that helped spawn the Lean Startup movement.

And when I say significantly, I mean it!  The Startup Owners Manual is 600 pages of really detailed how-to around the first two steps of Blank’s four steps, Customer Discovery and Customer Validation.  It doesn’t get into the last two steps at all, Customer Creation and Company Building.  It has a lot of overlap with Ash Maurya’s Running Lean (post, book), although it’s significantly more detailed.  And essentially, especially around the topic of “Company Building,” my book starts where this one stops.

One of Blank’s great lines in the book is that a “A startup is a temporary organization in search of a scalable, repeatable, profitable business model.”  That frames the whole Lean Startup movement really, really well.  The whole concept of Customer Discovery and Validation, of testing hypotheses, is critical to getting product-marketing fit right in a capital-efficient manner.  If I were starting Return Path today, we’d be using these methods from the get-go.

But Lean principles are wholly compatible with larger companies, as well, and in fact we use all of these principles in our product development organization today.  We adapt them for our size and scale and the fact that often we are selling either new or enhanced versions of existing product into existing customers, but our product teams have all embraced the Lean principles and the vocabulary around them, and our goal is that we should never bring a product to market that isn’t already being bought.

Selling a Line of Business

It’s been a couple of years since Return Path decided to focus on our deliverability business by divesting and spinning out our other legacy businesses. That link tells some of the story, and the rest is that subsequently, Authentic Response divested part of the Postmaster Direct business to Q Interactive.  Those three transactions, plus a number of experiences over the years on the buy side of similar transactions (Bonded Sender, Habeas, NetCreations), plus my learnings from talking to a number of other CEOs who have done similar things over the years, form the basis of this post.  The Authentic Response spin-out was also partially chronicled by Inc. Magazine in this article earlier this year.

It’s an important topic — as entrepreneurs build businesses, they frequently end up creating new revenue opportunities and go off on productive tangents.  Those new lines of business might or might not take off; but sometimes they can take off and still, down the road, end up being non-core to the overall mission of the company and therefore candidates for divestiture.  Even if they are good businesses, the overall enterprise might benefit from the focus or cash provided by a sale.  Look at the example of Occipital building the Red Laser app, then selling it to eBay to finance the rest of their business.

Here are some of the signs of a successful divestiture:

• Business is truly non-core or relies on starkly different competencies for success (e.g., one is B2B, the other is B2C)
• Business is growing rapidly and requires assistance to scale properly (either technology, or sales)
• Business has its own culture and operations and “a life of its own”

Conversely, here are some of the reasons why a divestitures of a business unit might stall or fail:

• Lack of a very compelling story as to why you’re selling the business unit
• Stand-alone financials of the unit are too hard for the buyer to determine with confidence
• Operations of the unit too tethered to the mothership
• There is some problem with the leadership of the unit (there is no stand-alone leader, the leader isn’t involved in the divestiture, the leader isn’t squarely behind the divestiture)
• Business performance weakens during the process

I have a couple points of advice to entrepreneurs in this situation.  The first is to clarify for yourself up front:  are you selling a true line of business, or are you selling assets?  If you are selling assets, you need to clearly define what they are, and what they aren’t, and you need to make sure all legal details (contracts, IP, etc.) are buttoned up before the process starts.

If you are selling a true line of business, beware that buyers will not be interested in doing any hard work, or if they feel like they have to do hard work, the price they pay for the business will reflect that in the form of a steep, steep discount.  The financials must be understandable and credible on a stand-alone basis.  The business must be completely separated from the core already.  The business must have its own management team, completely aligned with the decision to sell.

You also have to be extremely cognizant of the human aspects of what you’re doing.  Every culture is different, and I’m not advocating one style over another, but selling or spinning out a business is very different than selling a company.  There’s going to be a big difference in reactions, perceptions, hopes, and fears between the people in the core who are staying, and the people in the business unit that’s going.  Having a heightened awareness of those differences and factoring them into your communications plan is critical to success, as a poorly managed effort can end up harming both sides.

In terms of valuation expectations, don’t expect to get any credit for synergies.  You have to present them and sell them, and they may make the different between getting a deal done and not, but they will most likely not impact the price you get for the divestiture.

Finally, remember that buyers understand your psychology as well.  They know you’re selling the business for a reason (you need to raise cash, you’re concerned about its future performance, it’s become a distraction or has the potential to suck scarce resources out of your core, etc.).  They will completely understand the costs you carry, whether financial, opportunity, or mental, in continuing to own the business.  And they will factor that into the price they’re willing to offer.  Of course, as with all deals, the best thing you can do to maximize price is have multiple interested parties bidding on the deal!

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.

I was excited to read Launchpad Republic: America’s Entrepreneurial Edge and Why It Matters, by Howard Wolk and John Landry the minute Brad sent it to me. I love American history, I love entrepreneurship, and I’m deeply concerned about the health of our country right now. I have to say…on all fronts, the book did not disappoint!

The authors make several points, but the one that sets the tone for the book is that like our country’s origins and culture in general, entrepreneurship is itself rebellious. It’s about upstarts challenging the status quo in some way or other with a better way to do something, or with a new thing. The balance between protecting private property rights and allowing for entrepreneurs to fail and to disrupt incumbent leaders is what makes America unique, especially compared to the way European business culture has traditionally operated (consensus-oriented) and the way China operates (authoritarian).

I loved how the authors wove a number of business history vignettes together with relevant thru lines. Business in Colonial times and how Alexander Hamilton thought about national finances may seem dusty and distant, but not when you see the direct connection to John D. Rockefeller, IBM, GE, Microsoft, or Wendy Kopp.

The book was also a good reminder that some of the principles that have made America great and exceptional also underly our successful business culture, things like limited government, checks and balances within government and between government and the private sector, and decentralized finance.

Without being overly political, the authors also get into how our political and entrepreneurial system can and hopefully will tackle some of today’s more complex issues, from climate change to income inequality to stakeholder capitalism.

At the heart of all of it is the notion that entrepreneurs’ creativity drive America forward and are a leading force for making our country and our economy durable and resilient. As a career entrepreneur, and one who is now in the business of helping other entrepreneurs be more successful, this resonated. If you’re a student of American history…or a student of entrepreneurship, this is a great read. If you’re both, it’s a must read.

Book Short:  Entrepreneurial Lessons

The Startup Playbook: Secrets of the Fastest-Growing Startups from 42 Founders, by David Kidder, is the ultimate coffee table book for entrepreneurs and people who are interested in how they think about running their businesses.

David is the author of the Intellectual Devotional series (here’s a link to one of the five or six books in the series), he’s a good friend of mine and a member of a CEO Forum that I’m in, and my major disclosure about this blog post is that I’m one of the 42 entrepreneurs David interviewed for and profiles in the book.

The Startup Playbook is very different from my own book (in progress) on being a Startup CEO.  Where my book is going to go deep on different topics – think of it as a bit of a field guide – David’s book is extremely broad in its coverage of different entrepreneurs and their stories.  Taken together, the book paints a great picture of how CEOs think about the most important parts of the job.  It’s also a nice change of pace (for me, anyway) that David profiles some entrepreneurs who aren’t in the Internet/tech space.

It was an honor to be included in The Startup Playbook next to entrepreneurs like Reid Hoffman and Elon Musk.

My name is Matt Blumberg. I am a technology entrepreneur and business builder based in New York City. I am CEO of Markup AI, the leading provider of Content Guardian Agents to companies of all sizes looking to scale their use of AI to generate content smartly and safely. We are defining a new category in the Generative AI space and crushing it.

Before that, I started a company called Bolster, which was an on-demand executive talent marketplace.  We created a new way to scale executive teams and boards aimed at early and mid-stage tech companies. The business sort of worked and sort of didn’t work. We wound it down in 2025 and decided to focus on helping the portfolio companies we invested in via Bolster Ventures and help our friends with talent referrals on a more informal basis.

My longest career stint was Return Path, a company I started in 1999, which we sold in 2019.   We created a business that was the global market leader in email intelligence, analyzing more data about email than anyone else in the world and producing applications that solve real business problems for end users, commercial senders, and mailbox providers.  In the end, we served over 4,000 clients with about 450 employees and 12 offices in 7 countries.  We also built a wonderful company with a signature People First Culture that won a number of awards over the years, including Fortune Magazine’s #2 best mid-sized place to work in 2012.

Early in my career, I ran marketing and online services for MovieFone/777-FILM (www.moviefone.com), now a division of AOL. Before that — I was in venture capital at General Atlantic Partners (www.gapartners.com), and before that, a consultant at Mercer Management Consulting (www.mercermc.com). And I went to Princeton before that.

Based on this blog, I wrote a book called Startup CEO:  A Field Guide to Scaling Up Your Business, which was published by Wiley in 2013 and updated in 2020. I followed that by co-authoring a book with a number of my fellow executives from Retutrn Path and Bolster called Startup CXO: A Field Guide to Scaling Up Your Company’s Critical Functions and Teams; as well as the second edition of Startup Boards: A Field Guide to Building and Leading an Effective Board of Directors along with Brad Feld and Mahendra Ramsinghani. I hosted a podcast called The Daily Bolster, with over 200 micro-episodes (mostly 5-6 minutes long) where I interview other CEOs to share their stories and hacks.

I have been married for over 25 years to Mariquita, who is, as I tell her all the time, one of the all-time great wives. We have three great kids now in their late teens, Casey, Wilson, and Elyse.

I have lots of other hobbies and interests, like coaching my kids’ baseball and softball teams; traveling and seeing different corners of the world; reading all sorts of books, particularly about business, American Presidential history, art & architecture, natural sciences (for laymen!), and anything funny; cooking and wishing I lived in a place where I could grill and eat outdoors year-round; playing golf; lumbering my way through the very occasional marathon, eating cheap Mexican food; introducing my kids to classic movies; and playing around with new technology. I hosted a limited edition podcast series called Country Over Self which explored the topic of virtue in the Oval Office along with a dozen prominent presidential historians.

IF YOU WANT TO UNDERSTAND WHAT THIS BLOG IS ALL ABOUT, read my first two postings: You’re Only a First Time CEO Once, and Oh, and About That Picture, as well as my updated post when I relaunched the blog with its new name, StartupCEO.com.