Welcome to the new StartupCEO.com!

I started writing this blog in May of 2004 with an objective of writing about the experience of being a first-time entrepreneur — a startup CEO — inspired by a blog post written by my friend, long-time Board member and mentor Fred Wilson entitled “You’re only a first time CEO once.”  The blog and the receptivity I got along the way from fellow startup CEOs encouraged me to write a book called Startup CEO:  A Field Guide to Scaling Up Your Business, which was originally published in 2013 and then again as a second edition last year in 2020.

Today I am relaunching the blog as StartupCEO.com both to reflect that relevance of that brand as the book continues to get good traction in the startup ecosystem, and to reflect the fact that I’m now on my second startup as CEO, so “Only Once” doesn’t seem so fitting any more.

The web site has a very minimalist design – and I realize many of you read posts on either RSS or email — those will still operate the same as they have been (no new RSS feed).

As I approach the first anniversary of starting our new company, Bolster, where we help startup CEOs scale their teams, themselves, and their boards, I am recommitting to this blog and will try to post at least once a week.  Because there is a lot of overlap between this blog and Bolster’s blog (which I’d encourage you to subscribe to here either by email or RSS), posts will occasionally show up on both blogs, or I’ll put digests of Bolster blog posts here.  

But the Bolster blog will be broader and will also have many additional authors besides me, while this blog will remain distinct about some of the experiences I’m having as a startup CEO.

Try It On For Size

I’ve always been a big fan of taking a decision or a change in direction I’m contemplating and trying it on for size.  Just as you never know how a pair of pants is really going to fit until you slip them on in a dressing room, I think you need to see how decisions feel once you’re closing in on them.

Here’s why:  decisions have consequences.  No matter how prescient leaders are, no matter if they’ve been trained in chess-like (three-moves-ahead) thinking, they can almost never perfectly foresee all the downstream reactions and effects of decisions.  Figuring out how to create “mental fittings” is a skill that I think is critical for CEOs and other leaders.

When I try something on for size, I’m usually trying to accomplish one of a few things.  Sometimes, I’m simply trying to see how words sound when they come out of my mouth.  As Homer Simpson periodically muses, “did I think that, or did I say that out loud?”  There’s no substitute for articulating a new phrase, or theory, out in the open and seeing if it sounds the way YOU expect it to.  Other times, I’m trying to see how different messages or stories play with different audiences.  Will employees think it’s exciting when we announce X, or scary, or confusing?  Will a customer understand the new positioning of our company when you include the new product?  Will investors understand the story in 9 words or less?  Finally, there are times when my objective in trying something on for size is to understand specific downstream effects of a decision.  Throwing something out into the open and taking copious notes as people give you their “blink” concerns and reactions are invaluable.

Of course, the main thing to avoid when trying decisions or changes in direction on for size is creating chaos!  There are a few ways to create chaos.  One is by having your “try it on for size” conversation with an employee turn into a de facto decision because the employee takes your words and then deliberately acts on them.

Alternatively, the same thing could happen inadvertently because even though the employee knows intellectually not to act on your comments, he or she starts to incorporate them subconsciously, thinking they are likely to become the law of the land.

Another is by creating false expectations and disappointment if you decide an idea doesn’t fit when you try it on, and then you scrap it, leaving behind a trail of the idea for others to see and discuss.  All the same can be said with customers or investors or any other stakeholder.  Your words as CEO or any kind of a leader can be quite powerful, and trying something on for size can have real unintended consequences if not done carefully.

In all cases, the best antidotes are communication and judgment.  Make sure if you are trying something on for size internally that you communicate early and often to your audience that all you are doing is just that – trying something on, and follow up with people afterwards to make sure your intent really sunk in.  But judgment is also critical.  Pick your target audience for a fitting on carefully, make sure to blend trusted internal AND external associates, and make sure to rotate who you talk to about new things so you don’t develop a consistent bias in your idea generation.

In Defense of Email, Part 9,732

I commented today on our partner Blue Sky Factory’s CEO, Greg Cangialosi’s excellent posting in defense of email as a marketing channel called Email’s Role and Future Thoughts.  Since the comment grew longer than I anticipated, I thought I’d re-run parts of it here.

A couple quick stats from Forrester’s recent 5-year US Interactive forecast back up Greg’s points con gusto:

– 94% of consumers use email; 16% use social networking sites (and I assume they mean USE them – not just get solicitations from their friends to join).  That doesn’t mean that social networking sites aren’t growing rapidly in popularity, at least in some segments of the population, and it doesn’t mean that email marketing may not be the best way to reach certain people at certain times.  But it does mean that email remains the most ubiquitous online channel, not to mention the most “pull-oriented” and “on demand.”

– Spend on email marketing is $2.7b this year, growing to $4.2b in 2012.  Sure, email by 2012 is the smallest “category” by dollars spent, but first of all, one of the categories is “emerging channels,” which looks like it includes “everything else” in the world other than search, video, email, and display.  So it includes mobile as well as social media, and who knows what else.  Plus, if you really understand how email marketing works, you understand that dollars don’t add up in the same way as other forms of media since so much of the work can be done in-house. 

What really amazes me is how all these “web 2.0” people keep talking about how email is dying (when in fact it’s growing, albeit at a slower rate than other forms of online media) and don’t focus on how things like classifieds and yellow pages are truly DYING, and what that means for those industries.

I think a more interesting point is that in Forrester’s forecast, US Interactive Marketing spend by 2012 in aggregate reached $61b, more than triple where it is today — and that the percent of total US advertising going to interactive grows from 8 to 18 over the five years in the forecast. 

The bigger question that leaves me with is what that means for the overall efficiency of ad spend in the US.  It must be the case that online advertising in general is more efficient than offline — does that mean the total US advertising spend can shrink over time?  Or just that as it gets more efficient,
marketers will use their same budgets to try to reach more and more prospects?

My name is Matt Blumberg. I am a technology entrepreneur and business builder based in New York City who just (in 2020) started a new company called Bolster.

Bolster is an on-demand executive talent marketplace that helps accelerate companies’ growth by connecting them with experienced, highly vetted executives for interim, fractional, advisory, project-based or board roles. Bolster also provides on-demand executives with software and services to help them manage their careers as independent consultants and provides startup and scaleup CEOs with software and content to help them assess, benchmark and diversify their leadership teams and boards.  We are creating a new way to scale executive teams and boards.

Before that, I started a company called Return Path, 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 have been married for over 20 years to Mariquita, who is, as I tell her all the time, one of the all-time great wives. We have three great kids, 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.

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.

The Gift of Feedback, Part IV

I wrote a few weeks ago about my live 360 – the first time I’ve ever been in the room for my own review discussion.  I now have a development plan drafted coming out of the session, and having cycled it through the contributors to the review, I’m ready to go with it.  As I did in 2008, 2009, and 2011, I’m posting it here publicly.  This time around, there are three development items:

1. Continue to spend enough time in-market.  In particular, look for opportunities to spend more time with direct clients.  There was a lot of discussion about this at my review.  One director suggested I should spend at least 20% of my time in-market, thinking I was spending less than that.  We track my time to the minute each quarter, and I spend roughly 1/3 of my time in-market.  The problem is the definition of in-market.  We have a lot of large partners (ESPs, ISPs, etc.) with whom I spend a lot of time at senior levels.  Where I spend very little time is with direct clients, either as prospects or as existing clients.  Even though, given our ASP, there isn’t as much leverage in any individual client relationship, I will work harder to engage with both our sales team and a couple of larger accounts to more deeply understand our individual client experience.
2. Strengthen the Executive Committee as a team as well as using the EC as the primary platform for driving accountability throughout the organization.  On the surface, this sounds like “duh,” isn’t that the CEO’s job in the first place?  But there are some important tactical items underneath this, especially given that we’ve changed over half of our executive team in the last 12 months.  I need to keep my foot on the accelerator in a few specific ways:  using our new goals and metrics process and our system of record (7Geese) rigorously with each team member every week or two; being more authoritative about the goals that end up in the system in the first place to make sure my top priorities for the organization are being met; finishing our new team development plan, which will have an emphasis on organizational accountability; and finding the next opportiunity for our EC to go through a management training program as a team.
3. Help stakeholders connect with the inherent complexity of the business.  This is an interesting one.  It started out as “make the business less complex,” until I realized that much of the competitive advantage and inherent value from our business comes fom the fact that we’ve built a series of overlapping, complex, data machines that drive unique insights for clients.  So reducing complexity may not make sense.  But helping everyone in and around the business connect with, and understand the complexity, is key.  To execute this item, there are specifics for each major stakeholder.  For the Board, I am going to experiment with a radically simpler format of our Board Book.  For Investors, Customers, and Partners, we are hard at work revising our corporate positioning and messaging.  Internally, there are few things to work on — speaking at more team/department meetings, looking for other opportunities to streamline the organization, and contemplating a single theme or priority for 2015 instead of our usual 3-5 major priorities.

Again, I want to thank everyone who participated in my 360 this year – my board, my team, a few “lucky” skip-levels, and my coach Marc Maltz.  The feedback was rich, the experience of observing the conversation was very powerful, and I hope you like where the development plan came out!

Why Publishing Will Never Be the Same, Part I

As you may know, we published a book earlier this year at Return Path called Sign Me Up! Sales are going quite well, in case you’re wondering, and we also launched the book’s official web site, where you can subscribe to our “email best practices” newsletter.

The process of publishing the book was fascinating and convinced me that publishing will never be the same.  Even in two parts, this will be a long post, so apologies in advance. Front to back, the process went something like this:

– We wrote the content and selected and prepared the graphics

– We hired iUniverse to publish the book for a rough total cost of $1,500

– iUniverse provided copy editing, layout, and cover design services

– Within 8 weeks, iUniverse put the book on Amazon.com and BN.com for us (in addition to their site) and properly indexed it for search, and poof — we were in business

– Any time someone places an order on any of those three sites, iUniverse prints a copy on demand, binds it, and ships it off. No fuss, no muss, no inventory, but a slightly higher unit cost than you’d get from a traditional publisher who mass prints. We receive approximately 20% of the revenue from the book sale, and iUniverse receives 80%.  I’m not sure what cut they give Amazon, but it’s hard to imagine it’s more than 10-20% of the gross

Other than the writing part (not to be minimized), how easy is that?  So of course, that made me think about the poor, poor publishing industry. It seems to me that, like many other industries, technology is revolutionizing publishing.  Here’s how:

– Publishers handle printing and inventory.  iUniverse and its competitors can do it for you in a significantly more economic way.  Print on Demand will soon be de rigeur.

– Publishers handle marketing and distribution.  iUniverse gets you on Amazon.com and BN.com for free.  Amazon.com and BN.com now represent something like 12% of all book sales (cobbled together stats from iMedia Connection saying the annual online book sale run rate is now about $3 billion and the Association of American Publishers saying that the total size of the industry is $24 billion).  Google and Overture take credit cards and about 5 minutes to drive people to buy your book online.  Buzz and viral and email marketing techniques are easy and cheap.

– Publishers pay you.  Ok, this is compelling, but they only pay you (especially advances) if you’re really, really good, or a recognized author or expert. iUniverse pays as well, just in a pay-for-performance model.  Bonus points for setting yourself up as an affiliate on Amazon and BN to make even more money on the sale.  iUniverse actually pays a higher royalty (20% vs. 7.5-15% in the traditional model), so you’re probably always a fixed amount “behind” in the self-publish model, but you don’t have an agent to pay.

Unless you are dying to be accepted into literary or academic circles that require Someone & Sons to annoint you…why bother with a traditional publisher? As long as you have the up-front money and the belief that you’ll sell enough books to cover your expenses and then some, do it yourself.

In Part II, I will talk about how iUniverse pitches a “traditional publishing model” and why it only reinforces the point that the traditional model doesn’t make a lot of sense any more in many cases.

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?

The Gift of Feedback, Part III

I’ve written about our 360 Review process at Return Path a few times in the past:

• overall process
• process for my review in particular
• update on a process change and unintended consequences of that process change)
• learnings from this year’s process about my staff

And the last two times around, I’ve also posted the output of my own review publicly here in the form of my development plan:

• Here in 2008
• Here in 2009

So here we are again.  I have my new development plan all spruced up and ready to go.  Many thanks to my team and Board for this valuable input, and to Angela Baldonero (my fantastic SVP People and in-house coach), and Marc Maltz of Triad Consulting for helping me interpret the data and draft this plan.  Here at a high level is what I’m going to be working on for the next 1-2 years:

• Institutionalize impatience and lessen the dependency dynamic on me.  What does this mean?  Basically it means that I want to make others in the organization and on my team in particular as impatient as I am for progress, success, reinvention, streamlining and overcoming/minimizing operational realities.  I’ll talk more about something I’ve taken to calling “productive disruption” in a future blog post
• Focus on making every staff interaction at all levels a coaching session.  Despite some efforts over the years, I still feel like I talk too much when I interact with people in the organization on a 1:1 or small group basis.  I should be asking many more questions and teaching people to fish, not fishing for them
• Continue to foster deep and sustained engagement at all levels.  We’ve done a lot of this, really well, over the years.  But at nearly 250 people now and growing rapidly, it’s getting harder and harder.  I want to focus some real time and energy in the months to come on making sure we keep this critical element of our culture vibrant at our new size and stage
• I have some other more tactical goals as well like improving at public speaking and getting more involved with leadership recruiting and management training, but the above items are more or less the nub of it

One thing I know I’ll have to do with some of these items and some of the tactical ones in particular is engage in some form of deliberate practice, as defined by Geoffrey Colvin in his book Talent is Overrated (blog post on the book here).  That will be interesting to figure out.

But that’s the story.  Everyone at Return Path and on my Board – please help me meet these important goals for my development over the next couple of years!

Does size matter?

It is the age-old question — are you a more important person at your company if you have more people reporting into you?  Most people, unfortunately, say yes.

I’m going to assume the origins of this are political and military. The kingdom with more subjects takes over the smaller kingdom. The general has more stars on his lapel than the colonel. And it may be true for some of those same reasons in more traditional companies. If you have a large team or department, you have control over more of the business and potentially more of the opportunities. The CEO will want to hear from you, maybe even the Board.

In smaller organizations, and in more contemporary organization structures that are flatter (either structurally or culturally) or more dynamic/fluid, I’m not sure this rule holds any more. Yes, sure, a 50-person team is going to get some attention, and the ability to lead that team effectively is incredibly important and not easy to come by. But that doesn’t mean that in order to be important, or get recognized, or be well-compensated, you must lead that large team.

Consider the superstar enterprise sales rep or BD person. This person is likely an individual contributor. But this person might well be the most highly paid person in the company. And becoming a sales manager might be a mistake — the qualities that make for a great rep are quite different from those that make a great sales manager. We have lost a few great sales reps over the years for this very reason. They begged for the promotion to manager, we couldn’t say no (or we would lose them), then they bombed as sales managers and refused as a matter of pride to go back to being a sales rep.

Or consider a superstar engineer, also often an individual contributor. This person may be able to write code at 10x the rate and quality of the rest of the engineering organization and can create a massive amount of value that way. But everything I wrote above about sales reps moving into management holds for engineers as well.  The main difference we’ve seen over the years is that on average, successful engineers don’t want to move into management roles at the same rate as successful sales reps.

It’s certainly true that you can’t build a company consisting of only individual contributors. But that isn’t my point. My point is that you can add as much value to your organization, and have as much financial or psychic reward, by being a rock star individual contributor as you can by being the leader of a large team.

Size of Pie, a.k.a. What Type of Entrepreneur Are You?

Mmmm…pie.  A post that Fred had up a few weeks ago about an M&A Case study involving WhatCounts, a company in the email space that I’ve known and had a lot of respect for for years, got me thinking about two different topics.  The first is thinking about types of entrepreneurs.  I’ve always said there were two types:  serial entrepreneurs who are great at starting companies but less great at scaling them, and entrepreneurs who are often part of a group of founders but who go on to continue to run the business for the long-haul.

CEO David Geller’s quote that gets to the heart of this in Fred’s post was:

…a bigger piece of a smaller pie, at some point, is the same as a smaller piece of a much larger pie.  And, donʼt let anyone tell you that baking a bigger pie isnʼt a whole lot more difficult.

Although David is talking about taking in outside capital and founder dilution in pursuit of larger business growth and objectives, he is also getting to the same point about entrepreneur type.  Scaling an organization beyond proof of concept, happy few customers, and profitable to be a $50-100mm business (and beyond) requires a whole different skill set than starting something from scratch and turning an idea into reality.

And in a sense, David is right.  Baking a larger pie can be a whole lot more difficult for some entrepreneurs if they are more of the serial entrepreneur type, or at least it can be far less interesting and fulfilling if what gets you out of bed in the morning is creating new things.  But for other entrepreneurs who are more of the “run the business” variety, getting out of the creation phase and into the scaling phase is more interesting and maybe even less difficult.  Even though businesses are never de-risked and a larger business with more employees just means there are more chips on the proverbial table, baking a larger pie and tending to the things that come with it – people issues, innovating within a platform, solving customer problems – can be less daunting than creation for some entrepreneurs.  (Return Path is in its twelfth year – can you guess which kind I am?)

So David’s right in terms of his core point about founder equity value and how large a slice of how large a pie the founder ends up with.  But whether baking a larger pie is easier or harder is less about an inherent difficulty in pie-making and more about the type of entrepreneur involved.

I’ll cover my second reaction to Fred/David’s post next week.

Half the Benefit is in the Preparation

This past week, we had what has become an annual tradition for us – a two-day Board meeting that’s Board and senior management (usually offsite, not this year to keep costs down) and geared to recapping the prior year and planning out 2009 together.  Since we are now two companies, we did two of them back-to-back, one for Authentic Response and the other for Return Path.

It’s a little exhausting to do these meetings, and it’s exhausting to attend them, but they’re well worth it.  The intensity of the sessions, discussion, and even social time in between meetings is great for everyone to get on the same page and remember what’s working, what’s not, and what the world around us looks like as we dive off the high dive for another year.

The most exhausting part is probably the preparation for the meetings.  We probably send out over 400 pages of material in advance – binders, tabs, the works.  It’s the only eco-unfriendly Board packet of the year.  It feels like the old days in management consulting.  It takes days of intense preparation — meetings, spreadsheets, powerpoints, occasionally even some soul searching — to get the books right.  And then, once those are out (the week before the meeting), we spend almost as much time getting the presentations down for the actual meeting, since presenting 400 pages of material that people have already read is completely useless.

By the end of the meetings, we’re in good shape for the next year.  But before the meetings have even started, we’ve gotten a huge percentage of the benefit out of the process.  Pulling materials together is one thing, but figuring out how to craft the overall story (then each piece of it in 10-15 minutes or less) for a semi-external audience is something entirely different.  That’s where the rubber meets the road and where good executives are able to step back; remember what the core drivers and critical success factors are; separate the laundry list of tactics from the kernel that includes strategy, development of competitive advantage, and value creation; and then articulate it quickly, crisply, and convincingly. 

I’m incredibly proud of how both management teams drove the process this year – and I’m charged up for a great 2009 (economy be damned!).