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.

Delicious Irony

Great coverage in The Washington Post of an ironic aspect to the auto industry's poverty plea for a government bail-out this week.

The three execs from GM, Ford, and Chrysler each took a separate private jet from Detroit to DC for the Congressional hearings for the occasion. 

I'm not a fan of Congressional hearing grandstanding and think most members of congress are asses when they do things like this, but not this time.  These guys had it coming and clearly don't have a clue about symbolism (either the importance of it or the art of it). 

The details are rich.  Read them here.  Thanks to my colleague Stephanie Miller for pointing this one out.  Yeesh.

I love the concept of Servant Leadership.  From the source, the definition is:

While servant leadership is a timeless concept, the phrase “servant leadership” was coined by Robert K. Greenleaf in The Servant as Leader, an essay that he first published in 1970. In that essay, Greenleaf said:

“The servant-leader is servant first… It begins with the natural feeling that one wants to serve, to serve first. Then conscious choice brings one to aspire to lead. That person is sharply different from one who is leader first, perhaps because of the need to assuage an unusual power drive or to acquire material possessions…The leader-first and the servant-first are two extreme types. Between them there are shadings and blends that are part of the infinite variety of human nature.

“The difference manifests itself in the care taken by the servant-first to make sure that other people’s highest priority needs are being served. The best test, and difficult to administer, is: Do those served grow as persons? Do they, while being served, become healthier, wiser, freer, more autonomous, more likely themselves to become servants? And, what is the effect on the least privileged in society? Will they benefit or at least not be further deprived?“

A servant-leader focuses primarily on the growth and well-being of people and the communities to which they belong. While traditional leadership generally involves the accumulation and exercise of power by one at the “top of the pyramid,” servant leadership is different. The servant-leader shares power, puts the needs of others first and helps people develop and perform as highly as possible.

This is a very broad societal definition, but it’s fairly easy to apply to a more narrow corporate, or even startup environment.  Are you as a CEO oriented primarily towards your people, or towards other stakeholders like customers or shareholders?  By the way, trying to do right by all three stakeholders is NOT a problem in a world of being oriented towards one.  It’s just a philosophy around which comes first, and why.  Our People First philosophy at Return Path is fair clear that at the end of the day, all three stakeholders win IF you do right by employees, so they do the best possible work for customers, so you build a healthy and profitable and growing business.

CEOs who practice Servant Leadership aren’t necessarily focused on power dynamics, or on helping those least privileged in society (at least not as part of their job)…but they are focused on making sure that their employees most important needs are met — both in the moment, as in making sure employees are empowered and not blocked or bottlenecked, and over the long haul, as in making sure employees have opportunities to learn, grow, advance their careers, make an impact, and have the ability to live a well balanced life.

I was in a meeting a couple weeks back with another leader and a few people on his team.  He *seemed* to practice Servant Leadership the way he was speaking to his team members.  But he wasn’t, really.  He was doing something I refer to as Sucking Down.  He was telling them things they clearly wanted to hear.  He was lavishing praise on them for minor accomplishments.  He was smiling and saying yes, when what he really meant was no.  He was practicing the art of Sucking Up, only to people on his team, not to a boss.  I got a sense that something wasn’t right during the meeting, and then post meeting, he actually fessed up to me — even bragged about it — that he was being disingenuous to get what he wanted out of his people.

There’s a clear difference between Servant Leadership and Sucking Down in the long run.  The danger comes in the moment.  Just as managers need to build good detection skills to sniff out evidence of someone on their team Sucking Up, employees need to be able to understand that clear difference in their managers’ behavior as they think about how to manage their careers, and even where to work.

Book Short:  Bringing it on Home

You Can’t Teach a Cat How to Bark, But You Might be Able to Teach it How to Walk on its Hind Legs

My co-founder George and I have had this saying for a while.  Cats don’t bark.  They can’t.  Never will.  They also don’t usually walk on their hind legs in the wild, but some of them, after some training, could probably be taught to do so.

Working with people on career evolution sometimes follows that same path.  Lots of the time, an employee’s career evolution is natural and goes well.  They’re playing to their strengths, in their sweet spot, progressing along nicely.  But often that’s not the case.  And it goes both ways.  Some employees want something different.  The sales rep wants to be a sales manager.  The product manager wants to try marketing.  Sometimes the organization needs something different out of the person.  Be a stronger manager.  Be more collaborative.  Acquire more domain or functional expertise.

These transitions might or might not be difficult.  It completely depends on the person involved and the competencies required for the new role.  And that’s where the barking cat comes into play.  There’s more art than science here, but as a manager or as the employee, figuring out the gap between existing strengths/experience and the required competencies for the new job, and whether the missing elements *can* be taught or not is the exercise at hand.

I’m not sure there’s a useful rule of thumb here, either.  I had a boss once many years ago who said you can teach smart people how to do anything other than sales.  Another boss said you can teach anyone any fact, but you can’t teach anyone empathy.  Both of these feel too one-size-fits-all for me.  One thing we do at Return Path from time to time is encourage an employee facing some kind of stretch transition (for whatever reason) to participate in or run a short-term side project with a mentor that lets them flex some relevant new muscles.  Essentially we let them try it on for size.

Five Years On

As of this past weekend, I’ve been blogging on OnlyOnce for five years.  My main reflection as I was thinking about it during this morning’s run is that blogging is different.  I started blogging to try out what was at the time the “new, new thing” (there were almost no CEO blogs at the time), just like I have tried out lots of other new technologies or web services from time to time over the years — from Skype to Facebook to Twitter to about 50 others.

You’ll never see a tweet from me about an anniversary of using Twitter.  Or any other comparable from that above list.  Blogging has ended up being fundamentally different.  It’s not just another expression of my status updates or another way to connect with friends and colleagues.  It’s become a core part of my business operating system, although I suppose that’s the case for many other tools as well. 

I think the main difference is that OnlyOnce has become a true form of creative expression for me.  It’s like (I imagine) writing a book or composing a piece of music. I’m not suggesting it’s high art, but I view it more as an ongoing project than most other online tools or sites I’ve tried out over the years.

Here’s to the next five years of it.

Symbolism in Action

A couple months ago, I wrote about how the idiots who run the Big 3 US automakers in Detroit don’t have a clue about symbolism — the art or the science of it.  Yesterday, I wrote about how I think the non-headcount cuts to G&A that we’re making at Return Path during these challenging economic times will be positive for the company in the long run.  The two topics are closely related.

Obama announces on Day 1 that White House staffers who make more than $100k won’t be getting a pay raise this year.  Presumably all of those people just started their jobs on January 20 and wouldn’t be eligible for a raise until 2010.  Return Path cuts pilates classes in its Colorado office — an expense that must cost around $3,000/year.  Practically speaking, it won’t make a difference to our budget one way or another.  Microsoft lays off 1,400 people — a real number, certainly for those families — but that’s the equivalent of Return Path laying off 2 people. 

Sometimes the symbolic is just that.  It is something designed to send a signal to others, and not much more.  You could argue that all three examples above mean nothing in reality, so they were just symbolic.  A waste of time.

You can also make the argument that sometimes, when done right, symbolism turns into action as it motivates or serves as a catalyst for other changes.  Obama’s cuts may be fictitious, but they set the tone for broader action across a 2mm person bureaucracy.  Pilates in the office?  Feels too excessive these days, even for a company obsessed with its employees and their well being, in an era where we’re cutting back other things that are more serious.  Microsoft has gobs of cash and doesn’t need to worry about its future, but it wants to tell the other 99% of its employee population that it’s time to buckle down and fly straight.  And they will.

Anyone who thinks the synbolic doesn’t influence the practical should think again.  Or just talk to Caroline Kennedy about the impact of her admission that she hadn’t voted in years on her political ambitions.

Protecting the Inbox

We only have one out of our 13 core values at Return Path that’s closely related to the content of our business. But as with the other values, it says a lot about who we are and how we approach the work that we do. That value is:

We believe inboxes should only contain messages that are relevant, trusted, and safe

We occupy a pretty unique space in the email universe – we serve senders and receiving networks, but aren’t directly in the mail stream and therefore don’t directly touch end users.  So much of our business, from our Certification or whitelisting business, to our new Domain Assurance anti-spoofing/anti-phishing business, revolves around building trust in our company that this core value is critical to our survival. If we ran afoul of this core value — and it comes up all the time — we’d be dead in the water.

Here’s how it comes up:  because our Certification program is the closest thing on the Internet to guaranteed universal email delivery, every spammer and grey mailer in the world wants to be on it. We don’t just SELL access to our whitelist. Even once a prospect has been converted to an under-contract client, they have to APPLY for Certification.

It’s not easy to GET Certified. You have to be a really, really good mailer. Not just a real entity. Not just a big spender. You have to send mail that is safe and secure and wanted by end users. We have a variety of qualitative and quantitative methods we can use to determine this, and the requirements for Certified status and therefore Inbox placement are carefully negotiated and regularly reviewed with our ISP partners. Once a client is Certified, it’s not easy to STAY Certified because we are monitoring all of those same standards in real time, 24×7. Clients who go out of bounds get immediately suspended from the program until they are back in bounds. Clients who go out of bounds enough, we just terminate from the program for good.

By the way, just because we won’t certify a particular client isn’t an indictment that they are a spammer. It just means that their email programs still need to be subject to all the state of the art filtering and security measures that our ISPs have in their arsenal.  And most of the time, it doesn’t mean that we won’t work with them to improve the quality of their mail programs so their messages are relevant, trusted, and safe.

But at the end of the day, we’d rather not take money from questionable clients than compromise the quality of our Certification program. That’s a hard decision to make sometimes.  I’ve had to call large clients who are poor mailers and fire them more than once, and I’ve had to take angry phone calls and threatened legal action from clients or prospects many times over the years.  But for us, respect for end users and inbox security are deeply baked into the culture.  It’s why we developed the Domain Assurance product and launched it earlier this year.  And that’s why it’s one of our core values.

I was talking to a CEO the other day who believed it was “wrong” (literally, his word) to meet directly 1:1 with people in the organization who did not report to him.  I’ve heard from other CEOs in the past that they’re casual or informal or sporadic about this practice, but I’ve never heard someone articulate before that they actively stayed away from it.  The CEO in question’s feeling was that these meetings, which I call Skip-Level Meetings, disempowers managers.

I couldn’t disagree more.  I have found Skip-Level Meetings to be an indispensable part of my management and leadership routine and have done them for years.  If your culture is set up such that you as CEO can’t interact directly and regularly with people in your organization other than the 5-8 people who report to you, you are missing out on great opportunities to learn from and have an impact on those around you.

That said, there is an art to doing these meetings right, in ways that don’t disempower people or encourage chaos.  Some of these themes will echo other things I’ve written in recent posts like Moments of Truth and Scaling Me.  My five rules for doing Skip-Level Meetings are:

1. Make them predictable.  Have them on a regular schedule, whatever that is.  The schedule doesn’t have to be uniform across all these meetings.  I have some Skip-Levels that I do monthly, some quarterly, some once a year, some “whenever I am in town.”
   
2. Use a consistent format.  I always have a few questions I ask people in these meetings – things about their key initiatives, their people, their roadblocks, what I can do to help, what their POV is about the company direction and performance, how they are feeling about their role and growth.  I also expect that people will come with questions or topics for me.  If I have more meaty ad hoc topics, I’ll let the person know ahead of time.
   
3. Vary the location.  When I have regular Skip-Levels with a given person, I try to do the occasional one over a meal or drink to make it a little more social.  For remote check-ins, I now always do Skype or Videophone.
   
4. Do groups.  Sometimes group skip-levels are fun and really enlightening, either with a full team, or with a cross-section of skip-levels from other teams.  Watching people relate to each other gives you a really different view into team dynamics.
   
5. Close the loop.  I almost always check-in with the person’s manager BEFORE AND AFTER a Skip-Level.  Before, I ask what the issues are, if there is anything I should push on or ask.  After, I report back on the meeting, especially if there are things the person and I discussed that are out of scope for the person’s job or goals, so there are no surprises.

 I’m sure there are other things I do as well, but I can’t imagine running the company without this practice.  Doing it often and well EMPOWERS people in the company…I’d argue that managers who feel disempowered by it aren’t managers you necessarily want in your business unless you really run a command-and-control shop.

Book Short:  Scrum ptious 

I just finished reading Scrum: The Art of Doing Twice the Work in Half the Time, by Jeff Sutherland and JJ Sutherland. This reading was in anticipation of an Agile Facilitation training my executive team and I are going through next week, as part of Return Path’s  Agile Everywhere initiative. But it’s a book I should’ve read along time ago, and a book that I enjoyed.

Sutherland gets credit for creating the agile framework and bringing the concept scrum to software development over 20 years ago. The book very clearly lays out not just the color behind the creation of the framework, and the central tenets of practice again, but also clear and simple illustrations of its value and benefits.  And any book that employs the Fibonacci series and includes Theodore Roosevelt’s “Man in the Arena” quote — my all-time favorite — is off to a good start by me.

I’ve always appreciated a lot of the underlying philosophy of Agile, such as regularly checking on projects, course correcting in response to feedback from customers or other stakeholders, and working hard to remove any impediments to progress in real time.

One of the author’s most poignant points is that “multitasking makes you stupid.”  I hadn’t focused in the past how agile allows you to clear away context shifts to focus on one task at a time, but that’s another great take away from the book.

Our Agile Everywhere initiative, which is designed to improve productivity across the organization, as well as increase accountability through transparency, is even more critical in my view after having read this book.

The thing that I am left struggling with, which is still very much a work in progress for us, and hopefully something that we will address more head on in our training next week, is the application of the agile framework to teams that are not involved in the production of a tangible work product, such as executive or other leadership teams.  That is something that our Agile Everywhere deployment team has developed a theory about, but it still hasn’t entirely sunk in for me.

I can’t wait for next week’s training session!  If you have any experience applying the agile framework to different types of teams in your company I’d love to hear more about it in the Comments.

Inbox = Zero = Satisfying (Quasi Book Short)

I’m a big David Allen fan.  Amazingly enough, I haven’t blogged about him and his books yet, probably for the most part because I read the books before I started blogging.  But here they are.  The first one,  Getting Things Done: The Art of Stress-Free Productivity, is probably a little better than the sequel, Ready for Anything: 52 Productivity Principles for Work and Life, but both are worth reading.  When I first read them, they didn’t revolutionize my thinking about productivity and workflow management (I was already at least decent at those things), but they did really sharpen my thinking around the edges and give me a great framework to plug all my to-do lists into.

One of Allen’s great principles is Inbox = Zero…that in an email-centric office, you should try to completely empty out your Inbox at the end of every day.  Every item should have its home, even if that home is a “Will handle tomorrow” or “Waiting for Susie” folder.

Anyway, I usually get pretty close to Inbox = Zero, but the times I actually achieve it are few and far between.  This morning was one of those times.  It’s just incredibly satisfying.

Of course, it only lasted 8 minutes.