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 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.

Understanding the Drivers of Success

Although generally business is great at Return Path  and by almost any standard in the world has been consistently strong over the years, as everyone internally knows, the second part of 2012 and most of 2013 were not our finest years/quarters.  We had a number of challenges scaling our business, many of which have since been addressed and improved significantly.

When I step back and reflect on “what went wrong” in the quarters where we came up short of our own expectations, I can come up with lots of specific answers around finer points of execution, and even a few abstracted ones around our industry, solutions, team, and processes.  But one interesting answer I came up with recently was that the reason we faltered a bit was that we didn’t clearly understand the drivers of success in our business in the 1-2 years prior to things getting tough.  And when I reflect back on our entire 14+ year history, I think that pattern has repeated itself a few times, so I’m going to conclude there’s something to it.

What does that mean?  Well, a rising tide — success in your company — papers over a lot of challenges in the business, things that probably aren’t working well that you ignore because the general trend, numbers, and success are there.  Similarly, a falling tide — when the going gets a little tough for you — quickly reveals the cracks in the foundation.

In our case, I think that while some of our success in 2010 and 2011 was due to our product, service, team, etc. — there were two other key drivers.  One was the massive growth in social media and daily deal sites (huge users of email), which led to more rapid customer acquisition and more rapid customer expansion coupled with less customer churn.  The second was the fact that the email filtering environment was undergoing a change, especially at Gmail and Yahoo, which caused more problems and disruption for our clients’ email programs than usual — the sweet spot of our solution.

While of course you always want to make hay while the sun shines, in both of these cases, a more careful analysis, even WHILE WE WERE MAKING HAY, would have led us to the conclusion that both of those trends were not only potentially short-term, but that the end of the trend could be a double negative — both the end of a specific positive (lots of new customers, lots more market need), and the beginning of a BROADER negative (more customer churn, reduced market need).

What are we going to do about this?  I am going to more consistently apply one of our learning principles, the Post-Mortem  –THE ART OF THE POST-MORTEM, to more general business performance issues instead of specific activities or incidents.  But more important, I am going to make sure we do that when things are going well…not just when the going gets tough.

What are the drivers of success in your business?  What would happen if they shifted tomorrow?

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.

Book Short: Stick Figures That Matter

I have read a bunch of books lately to try to improve my presentation skills. The latest one, The Back of the Napkin: Solving Problems and Selling Ideas with Pictures, by Dan Roam, was good, and quite different from some of the others I’ve read recently like Presentation Zen and Beyond Bullet Points, both of which are much more focused on effective use of Powerpoint.

The Back of the Napkin takes a different approach. The focus is much more on creating compelling visuals. It’s not about Powerpoint so much as it is about teaching how to crystallize concepts into tight and compelling schematics. Roam creates two pretty good frameworks for thinking about this: one that breaks down the message of a given slide into its most simple element — are you describing a who (use a portrait), what (chart), when (timeline), where (map), why (plot), or how (flowchart)? And a second that takes that element and asks five questions about the best way to convey the information — simple vs. elaborate, quality vs. quantity, vision vs. execution, individual vs. comparison, or change state vs. as-is.

Both frameworks are good, and if you’re already doing really good presentations, this will help improve them. In short, I’d say The Back of the Napkin is a good read if you’re obsessed with creating compelling visuals, but it’s more of a deeper drill than the two books I noted above. I’d read and master the material from Presentation Zen for 101, then dive into this topic for the 201 course.

Book Short:  Fables and Morals

Courtesy of my colleague Stephanie Miller, I had a quick holiday read of Aesop & The CEO: Powerful Business Lessons from Aesop and America’s Best Leaders, by David Noonan, which I enjoyed.  The book was similar in some ways to Squirrel, Inc., which I recently posted about, in that it makes its points by allegory and example (and not that it’s relevant, but that it relies on animals to make its points).

Noonan takes a couple dozen of Aesop’s ancient Greek fables and groups them in to categories like Rewards & Incentives, Management & Leadership, Strategy, HR, Marketing, and Negotiations & Alliances – and for each one, he gives modern-day management examples of the lessons.

For example, in the Wolf in Sheep’s Clothing, the lesson clearly is to strike while the iron is hot, or that a good plan executed today is better than a perfect one that’s too late.  Noonan gives the example of Patton’s capture of Messina, Sicily during World War II.

And in The Hare & The Tortoise, where of course the moral is that slow & steady wins the race, Noonan gives the example of how New York Knicks coach Rick Pitino inspired Mark Jackson, who was chosen 18th in the NBA draft, to win the rookie of the year award in 1987 by helping him gain confidence by building on his strengths.

All in, a good read, even with that painful reminder that the Knicks used to have a decent basketball team.

Book Short:  Great Marketing Checklists

Trade Show and Event Marketing:  Plan, Promote, and Profit, by our direct marketing colleague Ruth Stevens, is hardly a page-turner, but it is a great read and well worth the money for anyone in your B2B marketing department.  That’s true as much for the event marketing specialist as the marketing generalist.

The author brings a very ROI-focused approach to planning and executing events – whether big trade shows or smaller corporate events, which are becoming increasingly popular in recent years for cost, focus, and control reasons.  But beyond events, the book has a number of excellent checklists that are more general for marketers that I found quite useful both as a reminder of things we should be doing at Return Path as well as ways we should be thinking about the different elements of our B2B marketing mix.

Some of the best tables and charts include:  strengths, weaknesses, and best applications of trade shows vs. corporate events; comparative analysis of marketing tools by channel (this was great – talks about best applications for all major tools from events to newsletters to search to inside sales); 12-month exhibitor timeline for trade shows; a great riff on bad booth signage vs. good booth signage (hint:  don’t make the visitor do the work – be obvious!); business event strategic planning grid; pre-show campaign and post-show follow-up checklists; dos, don’ts and options for corporate events; a great section on qualifying and handling leads that extends well beyond trade shows; and several good case studies that are show-focused.

Thanks to Ruth herself for an autographed copy!  Team Marketing and sales leaders at Return Path – your copies are on the way.

Book Short:  Just One Minute

What The One Minute Manager does for basic principles of management and goal setting, The One Minute Manager Meets the Monkey does for delegation.  Both are blessedly quick reads (the classic “airport” book), and Ken Blanchard really nails some of management’s most critical components with simplicity and grace.

I’m a fan of the One Minute Manager school, and it does work well for some of the basics, but it has its limitations in terms of how broadly it can be applied.  My colleague Whitney McNamara‘s words in an email to me a few months back say it all:

OMM has actually been useful.  I have to agree that it’s got a bit of a “Jonathan Livingston Seagull” mystical simplicity thing going, but as you say, simple is sometimes what works best.

It’s really strong in that the basic lessons are at root so simple that they’re easy to forget about day to day…having them articulated in a similarly simple way, so that they stick at the top of mind easily, is nice.

The other side of that is that it presents such a simplified, best-of-all-possible-worlds sort of scenario that I did sometimes find myself wanting to set fire to the OMM’s office building and scream “let’s see you deal with *this* in 60 seconds, buddy”…but on balance a pretty good experience. 🙂

In the end, it’s not that good management is easy — but it can be quick and relatively painless if done well and regularly.

Book Short:  Another 8 Habits

Besides having a fantastic title, Richard St. John’s Stupid, Ugly, Unlucky, and Rich is a fun and quick read.  It’s a completely different style than Stephen Covey’s “habits” books (The 7, The 8th).  It’s a little cartoony and list-oriented, and it’s a much quicker read — and also easier to put down and pick up without feeling like you’re losing your place.

The book’s foundation is interviews, mostly by the author, of successful people who span many different careers, from artists to actors and models to athletes to politicians to business leaders.  The organization is very solid, and the content is highly motivating.  It’s a good guide to success in any field, and in particular many of the examples are spot-on for entrepreneurship.

At a minimum, I’m buying it for my senior staff…and for every new entry-level employee as good career foundation reading material.

Startup CEO (OnlyOnce- the book!), Part IV – Book Launches Today!

My book is officially on sale on Amazon and iTunes today.  The full detailed outline is here if you’re interested, and the link to buy it is here.

This is very exciting.  I had been saying for a while that I had no idea whether 50 people would buy it or 5,000, but the publisher (Wiley) tells me we had over 2,000 pre-orders, so that’s a great start, at least.

So thanks to those 2,000 brave souls, and anyone else who buys it as well.  I hope you enjoy it and look forward to your feedback directly, via OnlyOnce, via the #StartupCEO hashtag, via a rating/review on Amazon, or via the Startup Revolution web site.

I hope to get back to more regular blogging soon.  As you hay have noted, I’ve been more quiet than usual the last six months while writing the book.  But I have lots of great posts stored up…

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.