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!).

People First

I do not think it’s telling that my fourth post in this series of posts on Return Path’s core values (kickoff post, tag cloud) is something called People First.  Ok, it probably should have been the first post in the series.  To be fair, it is the first value on our list, but for whatever reason, the value about Ownership was top of mind when I decided to create this series.

Anyway, at Return Path,

We believe that people come first

And we aren’t shy about saying it publicly, either.  This came up in a lengthy interview I did with Inc. Magazine last year when we were profiled for winning an award as one of the top 20 small- and mid-sized businesses to work for in America.  After re-reading that article, I went back and tried to find the slide from our investor presentations that I referred to.  I have a few versions of this slide from different points in time, including one that’s simpler (it only has employees, clients, and shareholder on it) but here’s a sample of it:

That pretty much says it all.  We believe that if we have the best and most engaged workforce, we will do the best job at solving our clients’ problems, and if we do that well, our shareholders will win, too.

How does this “people first” mentality influence my/our day-to-day activities?  Here are a few examples:

• We treat all employees well, regardless of level or department.  All employees are important to us achieving our mission – otherwise, they wouldn’t be here.  So we don’t do a lot of things that other companies do like send our top performing sales reps on a boondogle together while the engineers and accountants slave away in the office as second-class citizens.  That would be something you might see in a “sales first” or “customer first” culture
• We fiercely defend the human capital of our organization.  There are two examples I can think of around this point.  First, we do not tolerate abusive clients. Fortunately, they are rare, but more than once over the years either I or a member of my senior team has had to get on the phone with a client and reprimand them, or even terminate their contract with us, for treating one of our employees poorly and unprofessionally. And along the same lines, when all economic hell broke loose in the fall of 2008, we immediately told employees that while we’d be in for a rough ride, our three top priorities were to keep everyone’s job, keep everyone’s compensation, and keep everyone’s health benefits. Fortunately, our business withstood the financial challenges and we were able to get through the financial crisis with those three things intact.
• We walk the walk with regard to employee feedback.  Everyone does employee satisfaction surveys, but we are very rigorous about understanding what areas are making people relatively unhappy (for us, even our poor ratings are pretty good, but they’re poor relative to other ratings), and where in the employee population (office, department, level) those issues lie.  We highlight them in an all-hands meeting or communication, we develop specific action plans around them, and we measure those same questions and responses the next time we do a survey to see how we’ve improved
• We invest in our people.  We pay them fairly well, but that’s not what I’m talking about.  We invest in their learning and growth, which is the lifeblood of knowledge workers.  We do an enormous amount of internal training.  We encourage, support, and pay for outside training and education.  We are very generous with the things that allow our employees to be happy and healthy, from food to fitness to insurance to time off to a flexible environment to allowing them to work from another office, or even remotely, if their lives require them to move somewhere else
• I spend as little time as I possibly can managing my shareholders and as much time as I can with employees and prospective employees.  That doesn’t mean I don’t interact with my Board members – I do that quite a bit.  But it does mean that when I do interact with them, it’s more about what they can do for Return Path and less about reporting information to them.  I do send them a lot of information, but the information flow works well for them and simultaneously minimizes my time commitment to the process:  (1) reporting comes in a very consistent format so that investors know WHAT to expect and what they’re looking at, (2) reporting comes out with a consistently long lead time prior to a meeting so investors know WHEN to expect the information, (3) the format of the information is co-developed with investors so they are getting the material they WANT, and (4) we automate as much of the information production as possible and delegate it out across the organization as much as possible so there’s not a heavy burden on any one employee to produce it
• When we do spend time with customers (which is hopefully a lot as well), we try to spread that time out across a broad base of employees, not just salespeople and account managers, so that as many of our employees can develop a deep enough understanding of what our customers’ lives are like and how we impact them

There are plenty of companies out there who have a “shareholder first” or “customer first” philosophy.  I’m not saying those are necessarily wrong – but at least in our industry, I’ll bet companies like that end up with significantly higher recruiting costs (we source almost half our new hires from existing employee referrals), higher employee churn, and therefore lower revenue and profit per employee metrics at a minimum.  Those things must lead to less happy customers, especially in this day and age of transparency.  And all of those things probably degrade shareholder value, at least over the long haul.

(Post 3 of 4 in the series of Scaling CRO’s- the other posts are When to Hire your First Chief Revenue Officer and What does Great Look like in a Chief Revenue Officer).

If you’ve hired a “great” CRO (see previous post) you might think that you’re set for a long time and that the great CROs are also able to scale. Not always, and you’ll have to check to make sure that your CRO is scaling and growing as much as your company. I’ve found that there are several telltale signs that your CRO isn’t scaling and fortunately, they are easy to spot and easy to correct.

First, if your CRO gravitates to being an individual contributor sales rep and focuses on closing big deals instead of mentoring sales managers and sales reps to do that work on their own, that could be a sign that your CRO lacks the confidence to be a true executive.  The risk in being an executive is not that you can’t do the work, it’s that you don’t trust your team to do the work. To be clear, sometimes the role of a sales leader (or a CEO) is to swoop in and help close a big deal–sometimes.  But CROs who can’t shake their addiction to closing deals almost never build enough of that muscle into their organization and end up creating unhealthy dependency on themselves. Worse, they do not create a career path for others in the sales organization to learn and take risks. 

Second, I’ve found that a CRO who gets the sales commission plans out in March or April instead of January or early February is maybe someone who can’t scale.  While it’s true that, in a lot of businesses, it’s very difficult to get sales commission plans out until after the year starts, getting them out after late February is a sign that your CRO doesn’t have enough of a grip on numbers, isn’t partnering effectively with finance, doesn’t care enough about their people, or isn’t good at prioritizing the important over the urgent when needed. Obviously, if this happens once it’s not a big deal, but if you find that the CRO is the last person on your team to get their plans together year after year, that’s a telltale sign that maybe they’re in over their heads. You might hear them say, “They’ll all be fine, they know I’ll take care of them, the plan is a lot like last year’s.” That might be okay for the majority of the sales team but it won’t be good enough for the best reps who are constantly doing Sales Math in their heads.  It’s a lot easier to mentor or CRO, or find a new one, than to build a new team of dedicated sales reps.

Finally, a sign that your CRO isn’t scaling is if they regularly deliver surprises at the end of the quarter – both good and bad surprises.  A “surprise” every once in awhile is not a big deal, but regular surprises are a big deal and that tells you something important about the CRO: They might be incapable of scaling and the surprises are coiming because your CRO doesn’t have a good grip on the pipeline and in particular on larger deals. Either they don’t have a grip on the pipeline or they are bad at managing expectations; or both!

( You can find this post on the Bolster Blog here)

People Should Come with an Instruction Manual

Almost any time we humans buy or rent a big-ticket item, the item comes with an instruction manual.  Why are people any different?

No one is perfect.  We all have faults and issues.  We all have personal and professional development plans.  And most of those things are LONG-TERM and surface in one form or another in every single performance review or 360 we receive over the years.  So shouldn’t we, when we enter into a long-term personal or professional employment relationship, just present our development plans as instruction manuals on how to best work with, live with, manage, us?

The traditional interview process, and even reference check questions around weaknesses tend to be focused on the wrong things, and asked in the wrong ways.  They usually lead to lame answers like “my greatest weakness is that I work too hard and care too much,” or “No comment.”

The traditional onboarding process also doesn’t get into this.  It’s much more about orientation — here’s a pile of stuff you need to know to be successful here — as opposed to true onboarding — here’s how we’re going to get you ramped up, productive, integrated, and successful working here.

It’s quite disarming to insist that a candidate, or even a new employee, write out their instruction manual, but I can’t recommend it highly enough as part of one or both of the above two processes.  Since everyone at Return Path has a 360/Development Plan, I ask candidates in final interviews what theirs looks like in that context (so it’s clear that I’m not trying to pull a gotcha on them).  Failure to give an intellectually honest answer is a HUGE RED FLAG that this person either lacks self-confidence or self-awareness.  And in the onboarding process, I literally make new employees write out a development plan in the format we use and present it to the rest of my staff, while the rest of my staff shares their plans with the new employee.

As I’ve written in the past, hiring  new senior people into an organization is a little like doing an organ transplant.  Sometimes you just have to wait a while to see if the body rejects the organ or not.  As we get better at asking this “where’s your instruction manual?” question in the interview process, we are mitigating this risk considerably.  I’m sure there’s a whole parallel track on this same topic about personal relationships as opposed to professional ones, but I’ll leave that to someone else to write up!

Sometimes the work we do as CEOs, leaders, management teams is glamorous, and sometimes it’s not. But it all matters. One thing we tried to do at Bolster this past year is to really amp up employee benefits. The war for talent is real. The Great Resignation is real. Sometimes startups like ours have natural advantages in terms of attracting and retaining talent such as being made up of letting people in on the ground floor of something, having small teams so individual impact is easy to see, being mission-driven and full of creativity and purpose, and having equity to give that could be very valuable over time. But sometimes startups like ours have natural disadvantages around recruiting like having less certain futures, being relatively unknown to potential employees, being unable to pay huge salaries in the face of the Googles and Facebooks of the world, and having limited career path options since the teams are so small.

My co-founders and I have always been big believers in innovating People Practices. We did an enormous amount of work around this at our prior company, Return Path, which has been pretty well documented and we feel was very successful. Things like our People First philosophy of investing in our team, an extraordinary amount of transparency in the way we ran the company, a sabbatical policy, an open vacation policy, a peer recognition system, 360 reviews (I’ve written about this a lot, but I don’t have a great single post on it – this one is good enough and has some links to others), and an open expense policy.

Most of those things, when we started doing them 20 years ago, were revolutionary. We had our own version of the then-infamous Netflix deck even before we saw the Netflix deck. But today, many of those people practices are more common, not quite table stakes, but not exactly unique either. So this year when we set out to do our annual retrospective and planning process, we decided to try to innovate on a fairly standard topic for people, employee benefits. Although there’s not a lot of room for innovation on this topic, we are doing a few things that new and existing employees alike have told us are noteworthy, so I thought I would share them here.

We started by getting the basics right. We have a good solid health plan, dental plan, vision, transit benefits, etc. And we are paying 100% of the basic plan and allowing employees to pay more for a premium plan. That’s not the innovative part.

Next, we decided to max out the HSA contribution. HSAs and FSAs are some of those things that people don’t really think about, or they think “oh that’s great, employees can set aside health care expenses pre-tax.” But employer contribution to them matters, especially because the plans are portable. So we are giving people whatever the legal limit is towards their HSA, something in the neighborhood of $7k/year for a family plan or $3k for an individual plan. This is real money in people’s pockets, and it takes away from fears and concerns about health and wellness.

Next, we decided to begin addressing two things we felt were always weird quirks or inequities in benefit plans. One is the fact that employees who DO take advantage of your benefits program essentially get a huge additional amount of compensation than employees who DON’T because they are on their spouse’s plan. So we decided to give all employees who DON’T use our benefits program a monthly stipend. The amount doesn’t quite equal what we would be paying for their health insurance (which varies widely for employees based on single vs. family plans), but it’s a material number. So those people who aren’t on our plan still receive a healthcare proxy benefit from us.

Another (and the final thing I’ll talk about today) was instituting a 401k match, but doing so with a dollar cap instead of a percentage cap. Percentage caps FEEL fair, but they’re not fair since the company ends up paying more money towards the retirement plan of the people who earn the most money and who presumably need that benefit the least. The IRS tries to help do this leveling with their nondiscrimination testing, but that doesn’t come close to achieving the same outcome because it’s about employee contributions, not employer matches. By instituting a dollar cap, we are making the statement that we value all employees’ retirements equally. Incidentally, this simple change is proving to be very difficult to implement since our systems and benefits providers aren’t set up to do it, but we will persevere and find workarounds and get it right.

Investing in our people is critical to who we are as a business, and if you take your business seriously, it should be in your playbook as well. Benefits sound like a dumb area in which to innovate since they’re very common across all companies other than the percentage of the premium covered…but there’s still room for creativity even in that field.

First in my series of posts around creating the best place to work  is to Surround yourself with the best and brightest.  This one is simple.  Build the best team you can possibly build…as you need it.

As a founder, you may be the best person at doing everything in your company, especially if you are a technical founder.  But as my long-time Board member at Return Path Greg Sands always says, when the organism grows, cells start to specialize.  Eventually, you need a liver and a brain.  Just like companies need a head of sales and a CFO (not to imply that Anita likes the occasional cocktail or that Jack likes math – turns out both like both).

How does this come into play as a CEO?

-Don’t be afraid to hire people better than you at their specialty – older, wiser, more experienced, more expensive

– Check references carefully – don’t get suckered in by resume or rolodex – some successful big company people don’t actually know how to do work or build a business, so you have to dig and find back-channel references

– Don’t overhire before you’re ready, but especially as a start-up, better to hire 3 months before you need the position, not 6 months too late

-Remember that you are the CEO.  Even if you hire very experienced people in specific roles, you have the best global view of everything going on in the company.  And you need to pay attention to people on your team and actively manage them, even experts who are older or wiser than you are

Surrounding yourself with the best and brightest can be daunting and even threatening to some CEOs.  But you have to do it to grow your business.  And you have to keep doing it as you keep growing your business (and your staff has to do the same!).

Book Not-So-Short:  Not Just for Women

At the request of the women in our Professional Services team, I recently read Sheryl Sandberg’s Lean In:  Women, Work, and the Will to Lead, and while it may seem like dancing the meringue in a minefield for a male CEO to blog about it, I think it’s an important enough topic to give it a shot.  So here goes.

First, given the minefield potential, let me issue a few caveats up front.  These are deep, ages old, complex, societal issues and behaviors we’re talking about here.  There is no quick answer to anything.  There is no universal answer to anything.  Men don’t have the same perspective as women and can come across as observers (which in some respects, they are).  Working moms don’t have the same perspective as stay-at-home moms, or as single women.  We try to be good about all these issues at Return Path, but I’m sure we’ve only scratched the surface.  </caveats>

Perhaps most important, my overall take on the book is that it’s a very good business book that everyone should read – not just women.  I have a strong reaction to the reactions I’ve read and heard about the book – mostly from women dismissing the book because Sandberg has immense financial resources, so how could she possibly know the plight of the ordinary mom, and how could she understand what it is like to be a stay-at-home mom?  That reaction is to dismiss the dismissals!  I found the book to be very broadly applicable.  Of course things about life with a two-working parent family are easier if you have more money.  But that’s completely not the point of the book.  And Sandberg doesn’t once criticize stay-at-home moms for that choice – in fact, she acknowledges feelings of guilt and inferiority around them and admiration for the work they do that benefits all families and kids, not just their own.

Here are a few of the biggest areas of thinking, AHA, or questioning, that the book gave me:

• One of Sandberg’s underlying points is that the world would be a better place with more women in leadership positions, so that’s an important goal.  It’s interesting that few enough of our leaders are women, that it’s hard for me to draw that same conclusion, but it makes sense to me on the surface, and there’s some research about management teams and boards to back it up.  As far as I can tell, the world has yet to see a brutal female dictator.  Or a fair share of political or corporate scandals caused by women.  There are definitely some horror stories of “tough boss” women, but probably no more than “tough boss” men.  It’s interesting to note that in our society, leadership roles seem to be prized for their power and monetary reward, so even if the world wouldn’t be a better place with more female leaders, it would certainly be a more fair place along those two dimensions
• I felt that a bunch of Sandberg’s points about women were more generalizations about certain personality types which can be inherent in men and women.  Maybe they’re more prevalent in women, even much more, but some are issues for some men as well.  For example, her general point about women not speaking up even if they have something to say.  I have seen this trait in women as well as more introverted men.  As a leader, I work hard to draw comments out of people who look like they have something to say in a meeting but aren’t speaking up.  This is something that leaders need to pay close attention to across the board so that they hear all the voices around their tables.  Same goes for some of the fears she enumerates.  Many male leaders I know, myself included at times, have the “fear of being found out as a fraud” thought.  Same goes for the “desire to be liked by everyone” holding people back – that’s not gender specific, either.  All that said, if these traits are much more prevalent in women, and they are traits that drive attainment of leadership roles, well, you get the point
• The fact that women earn 77 cents on the dollar in equivalent jobs for men is appalling.  I’ve asked our People Team to do a study of this by level, factoring in experience and tenure, to make sure we don’t have that bias at Return Path.  I know for sure we don’t at the leadership level.  And I sure as heck hope we don’t anywhere in the organization.  We are also about to launch an Unconscious Bias training program, which should be interesting
• Sandberg made a really interesting point that most of the women who don’t work are either on the low end or high end of the income spectrum.  Her point about the low end really resonated with me – that women who don’t earn a lot stop working if their salaries only barely cover childcare costs.  However, she argues that that’s a very short term view, and that staying in the workforce means your salary will escalate over time, while childcare costs stay relatively flat.  This is compounded by the fact that women who lean back early in their careers simply because they are anticipating someday having children are earning less than they should be earning when they do finally have children.
• The other end of the income spectrum also made sense once I parsed through it – why do women whose husbands make a lot of money (most of whom make a lot of money as well) decide to off-ramp?  Sandberg’s point about the “Leadership ambition gap” is interesting, and her example of running a marathon with the spectators screaming “you know you don’t have to do this” as opposed to “you’ve got this” is really vivid.  See two bullets down for more on this one.  But it might not be straight-up Leadership Ambition Gap so much as a recognition that some of the high-earning jobs out there are so demanding that having two of them in the household would be a nightmare (noting that Dave and Sheryl seem to have figured some of that out), or that moms don’t want to miss out on that much of their children’s lives.  They want to be there…and they can afford to.  Another related topic that I wish Sandberg had covered in more depth is the path of moms who off-ramp, then re-on-ramp once their youngest children are in school, whether into the career they left or a different one.  That would be an interesting topic on many fronts
• Societal influences must matter.  The facts that, in 2011 – Gymboree manufactured onesies that say “smart like Daddy” and “pretty like Mommy,” and that JC Penney teenage girl t-shirts say “I’m too pretty to do homework so my brother has to do it for me” are more than a little troublesome on the surface (unless Gymboree also produces “handsome like Daddy” and “wicked smart like Mommy,” which somehow I doubt).  The fact that women do worse on math and science tests when they have to identify their gender at the top of the test is surprising and shocking
• I am really fortunate that Mariquita only works part time, and it’s unclear to me how our lives would work if we both worked full time, especially given my extremely heavy travel schedule, though I am sure we’d figure it out.  And there’s no way that I carry 50% of the burden of household responsibilities.  Maybe 20-25% at best.  But I was struck by Sandberg’s comments (I am sure true) that in two-working-parent families, women still carry the preponderance of household responsibilities on their shoulders.  I totally don’t get this.  If you both work, how can you not be equal partners at home?  A quick mental survey of a couple of the two-working-parent families we know would indicate that the parents split household responsibilities somewhat evenly, though you can never know this from the outside.  This should be a no brainer.  Sandberg’s point that men need to “lean into their families” is spot on in these cases for sure
• On a related note, Sandberg’s comment that “as women must be more empowered at work, men must be more empowered at home…moms can be controlling and critical…if he’s forced to do things her way, pretty soon she’ll be doing them herself” made me smile.  I have definitely seen this “learned helplessness” on the home front with dads quite a bit over the years
• One really good point Sandberg makes is that younger employees who don’t have kids should be allowed to have a life outside of work just as much as women who do have kids.  And that she pays people for the quality and quantity of their output, not their hours.  These are principles that match our values and philosophy at Return Path 100%
• Probably the most startling moment in the book for me – and I suspect many other men – was Sandberg’s vignette about the young woman at Facebook who was starting to “lean back” because she might someday have a family – before she was even dating anyone!  This really gave me a lot of pause.  If widespread (and I assume it is), there are clearly societal forces at work that we need to do more to help women early in their careers overcome, if they want to overcome them
• Sandberg’s point that a rich and fulfilling career “is a Jungle Gym, not a Ladder” is spot on, but this is true for men as well as women.  It matches our philosophy of Scaling Horizontally perfectly
• Another very poignant moment in the book was when Sandberg talked about how she herself had shown bias against women in terms of who she called on in meetings or lectures during Q&A.  Again, lots of pause for me.  If female leaders have the same societal bias against women, that’s a sign that we all have real work in front of us to help level the playing field around giving women air time.  Similarly, her example of the Heidi/Howard study was fascinating around how women with the same characteristics are perceived differently by both male and female co-workers gives me pause (for the record, I know the Heidi in question, and I like her!).  Likewise, the fact that female leaders are often given unflattering nicknames like “The Iron Lady” – you’d never see something like that for a man in the same position.  At least Thatcher wore the name as a badge of honor

I hope this post doesn’t end up as a no-win piece of writing where all I do is touch a few nerves and inspire no ongoing dialog.  “Let’s start talking about it,” the ending theme of the book, is a great way to end this post as well.  As with all tough issues, articulating the problem is the first step toward solving it.  Women need to allow men (as long as the men are open-minded, of course!) to think what they think, say what they think in a safe space, and blunder through their own learnings without feeling threatened.  And men need to be comfortable having conversations about topics like these if the paradigmatic relationship between women and leadership is going to continue to shift instead of avoiding the topic or just calling in HR.

Hopefully this blog post is one step towards that at my company.  Return Path colleagues – feel free to comment on the blog or via email and share stories of how we’ve either helped you or held you back!  But overall, I’m glad I read this book, and I’d encourage anyone and everyone to read it.

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.

5 Ways to Spot Trends That Will Make You (and Your Business) More Successful

I’ve recently started writing a column for The Magill Report, the new venture by Ken Magill, previously of Direct magazine and even more previously DMNews. Ken has been covering email for a long time and is one of the smartest journalists I know in this space. My column, which I share with my colleagues Jack Sinclair and George Bilbrey, covers how to approach the business of email marketing, thoughts on the future of email and other digital technologies, and more general articles on company-building in the online industry – all from the perspective of an entrepreneur. Below is a re-post of this week’s version, which I think my OnlyOnce readers will enjoy.

Last week I published my annual “Unpredictions” for 2011. This tradition grew out of the fact that I hate doing predictions and my marketing team loves them. So we compromise by predicting what won’t happen.

But the truth is that the annual prediction ritual – while trite – is really just trend-spotting. And trend-spotting is an important skill for entrepreneurs. Fortunately it’s a skill that can be acquired, at least it can with enough deliberate practice (another skill I talk about here).

Here are five habits you should consider cultivating if being a better trend spotter is in your career roadmap.

Read voraciously. I read about 50 books every year.  About half of them are business books, and I also mix in a bit of fiction, humor, American history, architecture and urban planning, and evolutionary biology.  I keep up with more than 50 blogs and I read all the trade publications that cover email.  I also read the Wall Street Journal and The Economist regularly.  What you read is a little less important than just reading a lot, and diversely.

Use social media (wisely). Julia Child once said that the key to success in life was having great parents. My advice to you is quite a bit simpler:  make friends with smart people. Facebook, Twitter, LinkedIn and others have given us a window into the world unlike any other. Status updates, tweets, and – maybe most important of all – links shared by your network of friends and colleagues gives you a sense of what people are talking about, thinking about and working on. And you can’t just lurk.  You actually have to be “in” to get something “out.”

Follow the money. Pay attention to where money gets invested and spent. This includes keeping an eye on venture capital, private equity, and the public markets, as well as where clients (mostly IT and marketing departments) are spending their dollars and what kinds of people they are hiring. Money flows toward ideas that people think will succeed. A pattern of investments in particular areas will give you clues to what might be the big ideas over the next five to 10 years.

Get out of the office: I think it’s hugely important for anyone in business, and especially entrepreneurs, to spend time in the world to get fresh perspectives. I’m not sure who coined the phrase, but our head of product management, Mike Mills, frequently refers to the NIHITO principle – Nothing Interesting Happens in the Office.  Now that’s not entirely true – running a company means needing to spend a huge amount of time with people and on people issues, but last year I traveled nearly 160,000 miles around the world meeting with prospect, clients, partners and industry luminaries. You don’t have to be a road warrior to get this one right – you can attend events in your local area, develop a local network of people you can meet with regularly – but you do have to get out there.

Take a break. While you need information to understand trends, you can quickly get overloaded with too much data.  Trend spotting is, in many ways, about pattern recognition. And that is often easier to do when your mind is relaxed.  Ever notice that you have moments of true epiphany in the shower or while running? Give yourself time every week to unplug and let your mind recharge. As Steven Covey says, “sharpen that saw”!

I wrote part I of this post in 2011, and I feel even more strongly about it today. I generally keep this blog away from politics (don’t we have enough of that running around?), but periodically, I find some common sense, centrist piece of information worth sharing. In this case, I just read a great and very short book, Six Amendments: How and Why We Should Change the Constitution, by former Supreme Court Justice John Paul Stevens, that, if you care about the polarization and fractiousness going on in our country now, you’d appreciate.

If nothing else, the shattered norms and customs of the last several years should point people to the fact that our Constitution needs some revision. Not a massive structural overhaul, but some changes on the margin to keep it fresh, as we approach its 250th anniversary in the next couple decades.

My cofounder Cathy wrote a great post on the Bolster blog back in January called Procrastinating Executive Development, in which she talks about the fact that even executives who appreciate the value of professional development usually don’t get to it because they’re too busy or don’t realize how important it is. I see this every day with CEOs and founders. Cathy had a well phrased but somewhat gentle ask at the end of her post:

My ask for all CEOs is this: give each of your executives the gift of feedback now, and hold each other accountable for continued growth and development to match the growth and development of your company.

Let me put it in starker terms:

Grow or Die.

Every executive, every professional, can scale further than they think is possible, and further than you think is possible. Most of us do have some ceiling somewhere…but it will take us years to find it (if we ever find it). The key to scaling is a growth mentality. You have to not just value development, you have to crave it, view it as essential, and prioritize it.

Startups are incredibly dynamic. You’re creating something out of nothing. Disrupting an industry. Revolutionizing something. Putting a dent in the universe. For a startup to succeed, it has to constantly put something in market, learn, calibrate, accelerate, maybe pivot, and most of all grow. How can a leader of a startup scale from one stage of life to the next without focusing on personal growth and development if the job changes from one quarter to the next?

I was lucky enough to have a great leadership team at my prior company, Return Path, over the course of 20 years. Within that long block of time with many executives, there was a particular period of time, roughly 2004-2012, that I jokingly refer to as the “golden age.” That’s when we grew the business from roughly $5mm in revenue to $50 or $60mm. The remarkable thing was that we executed that growth with the same group of 5-6 senior executives. A couple new people joined the team, and we struggled to get one executive role right, but by and large one core group took us from small to mid-sized. Why? We looked at each other — literally, in one meeting where we were talking about professional development — and said, “we have to commit to individual coaching, to team coaching, and to growth as leaders, or the company will outpace us and we’ll be roadkill.”

That set us on a path to focus on our own growth and development as leaders. We were constantly reading and sharing relevant articles, blog posts, and books. We engaged in a lot of coaching and development instruments like MBTI, TKI, and DISC. We learned the value of retrospectives, transparent 360s, and a steady diet of feedback. We challenged ourselves to do better. We worked at it. As one of the members of the Golden Age said of our work, “we went to the gym.”

The “Grow or Die” mantra is real. You can’t possibly be successful in today’s world if you’re not learning, if you don’t have a growth mentality. You are never the smartest person in the room. The minute you are convinced that you are…you’re screwed.

If you don’t believe me, look at the development of your business itself as a metaphor for your own development as a leader. What happens to your startup if it stops growing?

(You can find this post on the Bolster Blog here)