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.

My long-time friend and former Board member Brad Feld has become a prolific writer on the startup world over the years and is the person (other than me) most responsible for me getting into that scene as well. Startup CEO is part of his Startup Revolution series, which followed me writing an essay for Do More Faster, and then writing a series of sidebars call “The Entrepreneur’s Perspective” in Venture Deals.

All Brad’s books are listed here. If you’re in the startup universe, I’d encourage you to read all of them. I’m excited to dive into his newest book, The Startup Community Way, which comes out this week from our same publisher, John Wiley & Sons. I’ve gotten part of the way through an early copy, and I love it already.

The approach Brad and his co-author Ian Hathaway take is to evolve their Boulder Thesis from the original Startup Communities book. They dive into the topic and examine it from the perspective of a complex system, which of course anything as fragmented as an ecosystem of public, private, and academic organizations is.

The book — and the whole topic, quite frankly — remind me of a great management book I read several years ago by General Stanley McChrystal called Team of Teams. Organizations have gotten more complex and have had to adapt their structures, and the most successful ones are the ones that have shifted from hierarchical structures to node-based structures, or teams of teams, where individual, agile teams operate with loose points of connection to other teams that focus on dependencies and outcomes.

In the same way, startup communities and the broader ecosystems that touch them have changed and adapted, and the successful ones have learned how to stay loosely connected to other startup communities, prioritize collaboration, and remain focused on inclusion and entrepreneurial leadership.

(This is the fifth post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  Other posts in order are 1, 2, 3, and 4.)

Thursday, March 26, Day 10

• Sarah continuing to take over and stronger by the day
• Sarah cleared me to go home, only one more person to ask
• Deep deep dive on Mass Testing – so good to spend that time 
• Pretty much got the strategy right – shocking we could get that close with so little public health experience – Kyle awesome – EOC leadership briefing
• That was most of the day
• Some downloads to Sarah and Kacey
• Feeling that two of our project teams are going sideways – that will be a big focus for me tomorrow before I leave
• Quick assignments for tomorrow
• Talked to Jared – he’s good with me going now that Sarah is in place and things are running.  Awesome!

Friday, March 27,  Day 11

• Download with a couple of the project teams to help get them back on track 
• This whole thing is one big exercise in Agile!
• Serendipitously might have found private sector partner for one of the teams in need.  Reminded of George’s great line, “when the student is ready, the teacher appears”
• Gov briefing on mass testing plan
• Spent a lot of the day on strategy/overview/retrospective deck.  Have to review it with Brad and core team members. Gov wants to get it in front of the National Governors Association to share learnings/best practices for the states behind us in this fight
• Gov thankful goodbye
• Brad thank you Haiku – so awesome – “You see things others don’t see”
• FInal team check-in, lots of nice thank yous from people on team
• Close out drinks with Sarah, Kacey, Kyle – persevered despite lack of corkscrew.  Poor Kyle’s shirt looks like he was standing next to a shooting victim
• Incredibly thankful moment with team – really like and care about these people – we’ve done such great work together – 11 days but feels like months and months
• Close out email to Governor and Chief of Staff about team

Saturday, March 28, Day 12

• Check out!  Fly home! Happy to see Mariquita, Casey, Wilson, and Elyse!

Stay tuned for two more wrap-up posts, tomorrow and the next day…

(This is the third post in a series documenting the work I did in Colorado on the Governor’s COVID-19 Innovation Response Team – IRT.  First two posts are here and here.)

Friday, March 20, Day 4

• Morning pilates going pretty well, a good daily routine here
• Wellness Screening on the way in for the first time.  Uniformed National Guard guys taking temperature on surface of face/temples.  Can’t get it to work – takes 6x
• Leadership and prioritization of important over urgent – staff the team
• Strategic National Stockpile failure – they send us 60,000 masks and Colorado is using 68,000/day.  They send us ZERO ventilators. Seems like it’s neither strategic nor a stockpile. Guess it really is every state for itself
• Unclear sometimes what the actual role of the state is – sometimes procuring, sometimes getting private sector to procure with some coordination, etc.
• Getting out in front of the parade – the private sector is swarming all over this, how can we help coordinate and channel the energy?
• State gov seems incredibly nimble here – seconding people from departments all over to the crisis, etc.  Bureaucracy is real, but it can melt away in an emergency, or when the governor wants it to. Really impressive
• Going to try DoorDash and see if it’s any different than UberEats.  (It’s not.) Big night.

Saturday, March 21, Day 5

• Saturday but office still 75%
• Wellness Screening again.  Still can’t get thermometer to work for quite a while
• Mike Willis asked for feedback and observations (good) – they are
  • Atmosphere in EOC calm, focused, integrated, SMART, nimble, fast – opposite of “government”
  • Opening meeting on Tuesday morning – calm, focused, caring, quiet urgency
  • Didn’t realize he was military
  • Mentioned yesterday’s “not vetted, not integrated, not helpful” moment, poignant but respectful
• Team pull up, drowning in emails, plan to get organized
• Governor briefing
• Working on replacing me…
• Seamless prioritization of things that are gateway items and enablers.  We have a project tracker, but it’s almost useless. Mostly we are just doing prioritization in the moment.  No choice. Crisis mode
• Gov call – carefully weighing isolation strategy (economic as well as risk of civil disobedience) with number of projected deaths – sounds like the same conversation I’m reading about in the papers at the national level, but really interesting to see it up close and personal. Asked for plan around making food and services safer – super thoughtful “it’s not the economic activity that causes problems, it’s social proximity, are there ways we can keep one and minimize the other?”
• Colorado still has around 500 cases statewide – about ¼ of Westchester County.  Denver has less than 100. Still, feels like we are watching the tsunami coming at us in slow motion
• Dinner at a very close friend’s house who lives in town – elbow bumps and sat at the other end of the table.  Fun and social, but feels like even things like this are about to come to an end. Got to do laundry

Sunday, March 22, Day 6

• Sunday but office still 75%
• Multiple failures again with wellness screen, then we figure it out – on the walk over from the hotel, it’s cold enough that my skin temperature is out of range for the contact thermometers they have.  Since I am coming in early when there is no line, my face is too cold when I get to the front
• Adding staff, nowhere to put them, no organized email lists, working on org charts, have to retool O/S for meetings/tasks.  A little chaotic, but at least I know how to do this stuff
• Finally got connection to NY State to do some benchmarking on testing – doesn’t seem like states coordinate or share info a lot, but the team there was happy to 
• Finally have a few minutes to do planning on major swim lanes
• More working on replacing me
• This is the problem with statistics.  Models are only as good as the inputs, and the inputs here seem like they’re all over the place…not just here in CO, but everywhere.  It’s not like we have a pandemic every year to refine our math
• Interviewing Sarah Tuneberg (came in via Brad) to replace me with Lisa and Stan – she’s AWESOME and she’s hired – starts on the spot by coming in to stand with us behind the Governor at a press conference.  Talk about a rapid recruiting process!
• Seems like she will be awesome.  Probably way better than me – has a ton of public health and emergency/disaster response experience in addition to some private sector/startup/tech experience
• Her first worry never even occurred to me – Fatality Management – morgue surge capacity.  “Gift to the living” – so awesome
• Lameness of Trump press conference – self praise followed by sycophants in the midst of a typhoon
• Gov press conference (here) – authentic and well received.  “Grim reaper” was quite poignant. He worked in the key messages we asked him to about public misinformation of testing, talking points was Google Doc with 30+ people in it – good example of collaboration and control, seamless, last minute but still came out great.  Announces social distancing and lots of good examples about groceries, jogging, still no lockdown
• Lots of RP Colorado people seeing press conference…phone buzzing like mad in my pocket!  So many awesome notes from friends and former colleagues thanking me for being there to help, only one or two snarky comments about my orange tee shirt while others were in blazers (hey, it was a Sunday and the presser was called last minute!)

Stay tuned for more tomorrow…

We run a massive employee survey every year or so called The Loop, which is powered by Culture Amp.  We are big fans of Culture Amp, as they provide not only a great survey tool but benchmarks of relevant peer companies so our results can be placed in external context as well as internal context.

The survey is anonymous and only really rolled up to large employee groups (big teams, departments, offices, etc.), and we take the results very seriously.  Every year we run it, we create an Organization Development Plan out of the results that steers a lot of the work of our Leadership team and People team for the coming year.

I just read every single comment that employees took the time to write out in addition to their checkbox or rating responses.  This year, that amounted to over 1,200 verbatim comments.  I am struggling to process all of them, for a bunch of reasons you’d expect.  Next year we may give employees some examples of comments that are hard to process so they understand what it’s like to read all of them…and we may reduce the number of places where employees can make comments so we try to get only the most important (and more detailed) comments from people to keep the volume a little more manageable.

But I thought it might be useful to give some general advice to people who write comments on anonymous surveys.  Your company may have every good intention of following up on every last comment in an employee survey (we do!), but it’s difficult to do so when:

• The comment is not actionable.  For example, “The best thing about working at Return Path is…’I can afford to live nearby.'”  That doesn’t do much for us!
• The comment is too vague.  For example, “I’m not the engineer I was a year ago” – we have no idea what that means.  Is it a plus or a minus?  What is behind it?
• The comment is likely to be in conflict with other comments and doesn’t give enough detail to help resolve conflicts.  40 positive comments about the lunch program in an office and 40 negative comments about the lunch program in the same office kind of get washed out, but “Lunches are good, but please have more gluten-free options” is super helpful.
• The comment lacks context.  When the answer to the question “What would be the one thing we could do right away to make RP a better place to work?” is “Investing in some systems,” that doesn’t give us a starting point for a next step.
• The commenter disqualifies him or herself.  Things like “Take everything I’m saying with a grain of salt…I’m just an engineer and have no real idea of what I’m doing” that punctuate a comment are challenging to process.
• The commenter forgets that the comments are anonymous.  “I have serious problems with my manager and often think of leaving the company” is a total bummer to hear, but there’s not a lot we can do with it.  I hope with something like this that you are also having a discussion with someone on the People team or your manager’s manager!

We’re doing everything employees would expect us to do – reading the ratings and comments, looking at trends over time, breaking them down by office and department, and creating a solid Organizational Development Plan that we’ll present publicly and follow up on…but hopefully this is useful for our company and others in the future as a guide to more actionable commenting in employee surveys.

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.

My dad (one of my main CEO/entrepreneur role models) and I team-teach a business school class in entrepreneurial leadership every year at USD where a friend of his is the professor.  Sometimes I go in person, usually I just do it by video.  We did this a few weeks ago, and my dad talked through a decision-making framework that I’d never heard him mention before.

I sketched it out and really like it and am already using it internally, so I thought I would share it here as well:

To walk through it, delegating decision-making to someone on your team can be as simple as understanding where a decision falls along two different spectrums.  On the vertical axis is “How familiar is the person with this type of decision?” – meaning, has the person seen and made this kind of decision before?  This could be something like firing an employee, signing a contract, negotiating a vendor agreement.  On the horizontal axis is “What are the consequences of getting the decision wrong?” – which is really self explanatory…how big a deal is this?

The primary, upper right quadrant of “The person has made this decision before, and it’s not a huge deal” is an easy one – delegate the decision-making authority.  The two middle quadrants of “big deal, but familiar with the decision” and “never seen this before, but not a big deal” are ripe for the old adage of ask forgiveness later, not permission first, meaning it’s ok to delegate decision-making authority, but hold the person accountable for letting you know about decisions like that so you can be on the lookout for potential required clean-up.

But what I love most is the way my dad framed the final quadrant (lower left here), which is “high stakes decision, never seen this situation before.”  It can be tempting for a senior manager or CEO to just take this quadrant over and remove decision-making authority from a team member.  But it’s also a perfect teaching/coaching moment.  So the rule of thumb for this quadrant is “make the decision with me, but please come to me with a proposal on it.”

And that’s why my dad is such a great business mentor!

Book Short – A Smattering of Good Ideas that further my Reboot path

Ram Charan’s The Attacker’s Advantage was not his best work, but it was worth the read.  It had a cohesive thesis and a smattering of good ideas in it, but it felt much more like the work of a management consultant than some of his better books like Know How (review, buy), Confronting Reality (review, buy), Execution (review, buy), What the CEO Wants You to Know ( buy), and my favorite of his that I refer people to all the time, The Leadership Pipeline (review, buy).

Charan’s framework for success in a crazy world full of digital and other disruption is this:

Perceptual acuity (I am still not 100% sure what this means)

1. A mindset to see opportunity in uncertainty
2. The ability to see a new path forward and commit to it
3. Adeptness in managing the transition to the new path
4. Skill in making the organization steerable and agile

The framework is basically about institutionalizing the ability to spot pending changes in the future landscape based on blips and early trends going on today and then about how to seize opportunity once you’ve spotted the future.  I like that theme.  It matches what I wrote about when I read Mark Penn’s Microtrends (review, buy) years ago.

Charan’s four points are important, but some of the suggestions for structuring an organization around them are very company-specific, and others are too generic (yes, you have to set clear priorities).  His conception of something he calls a Joint Practice Session is a lot like the practices involved in Agile that contemporary startups are more likely to just do in their sleep but which are probably helpful for larger companies.

I read the book over a year ago, and am finally getting around to blogging about it.  That time and distance were helpful in distilling my thinking about Charan’s words.  Probably my biggest series of takeaways from the book – and they fit into my Reboot theme this quarter/year, is to spend a little more time “flying at higher altitude,” as Charan puts it:  talking to people outside the company and asking them what they see and observe from the world around them; reading more and synthesizing takeaways and applicability to work more; expanding my information networks beyond industry and country; creating more routine mechanisms for my team to pool observations about the external landscape and potential impacts on the company; and developing a methodology for reviewing and improving predictions over time.

Bottom line:  like many business books, great to skim and pause for a deep dive at interesting sections, but not the author’s best work.

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.

One of the things I’ve learned over the years is that as the organization scales, you have to be all-in, until you’re not.  What the heck does that mean?

It means that, other than confiding your indecision to a very small number of trusted advisors on a given issue, indecision is poison to the people around you and to the organization in general.  So even if you’re thinking of doing something new or different or making a tough call on something, you generally need to project confidence until you’ve made the call.

One example of this is around a decision to fire someone on the team, especially a senior executive.  Public indecision about this reminds me of years ago when George Steinbrenner owned the Yankees.  Every time he contemplated firing a manager, which was often, he was very public about it.  It turned the manager into a lame duck, ignored by players and mocked by the press.  No good for the manager or for the players, unhelpful for the team as a whole.  It’s the same in business.  Again, other than a small group of trusted advisors, your people have to have your full backing until the moment you decide to remove them.

Another example of this is a shift in strategy.  Strategy drives execution – meaning the course you chart translates into the goals and activities of all the other people in your organization.  Mobilizing the troops is hard enough in the first place, and it requires a tremendous amount of leadership expressing commitment.  If you’re contemplating a shift in strategy, which of course happens a lot in dynamic businesses, and you share your thinking and qualms broadly, you risk paralyzing the organization or redirecting activities and goals without intending to or without even knowing it.

Some people might look at this concept and cry “foul – what about Transparency?”  I don’t buy that.  As I wrote recently in The Difference Between Culture and Values, “When you are 10 people in a room, Transparency means you as CEO may feel compelled to share that you’re thinking about pivoting the product, collect everyone’s point of view on the subject, and make a decision together. When you are 100 people, you probably wouldn’t want to share that thinking with ALL until it’s more baked, you have more of a concrete direction in mind, and you’ve stress tested it with a smaller group, or you risk sending people off in a bunch of different directions without intending to do so. When you are 1,000 employees and public, you might not make that announcement to ALL until it’s orchestrated with your earnings call, but there may be hundreds of employees who know by then. A commitment to Transparency doesn’t mean always sharing everything in your head with everyone the minute it appears as a protean thought.  At 10 people, you can tell everyone why you had to fire Pat – they probably all know, anyway.  At 100 people, that’s unkind to Pat.  At 1,000, it invites a lawsuit.”

Book Short:  Best Book Ever

The Hard Thing About Hard Things, by Ben Horowitz, is the best business book I’ve ever read.  Or at least the best book on management and leadership that I’ve ever read.  Period.

It’s certainly the best CEO book on the market.  It’s about 1000 times better than my book although my book is intended to be different in several ways.  I suppose they’re complementary, but if you only had time left on this planet for one book, read Ben’s first.

I’m not even going to get into specifics on it, other than that Ben does a great job of telling the LoudCloud/Opsware story in a way that shows the grit, psychology, and pain of being an entrepreneur in a way that, for me, has previously only existed in my head.

Just go buy and read the book.