I have an end of year work routine that’s a pull-up and self-assessment. I’ve been doing this for years, and I’ve written about its evolution in Part I and Part II of this series.

I’ve always taken a few minutes at this time of the year to ask myself these four questions:

• Am I having fun at work?
• Am I learning and growing as a professional?
• Is my work financially rewarding enough, either in the short-term or in the long-term?
• Am I having the impact I want to have on the world?

If I answer at least 2.5 of these questions as yes, I feel like things are on track. If I am below that, or even at 2.5 sometimes, it’s time for a rethink of what I’m doing or how I’m doing it.

I was having lunch with my friend Bryton, the CEO of Aquabyte, a few weeks back, and that conversation spurred on a 5th question, which I’ll now add to my end of year routine:

• Am I excited about what I’m doing?

I’ve realized now that I’m over two years into the journey at Bolster that there’s a significant value in being really into the subject matter of the business. I thought I was at Return Path…but now I realize that I wasn’t nearly as excited about what I was doing as I could have been. Our work at Bolster of helping founders be more successful is more personally meaningful to me than solving email deliverability challenges. That work had real impact on the world…but I just wasn’t into it as much.

And that makes a big difference in answering the general question of “Am I on track?” at the end of the year. I’ll skip next week and see you all in 2023. Happy New Year and Happy Holidays, everyone!

The old carpenter’s axiom of being extra careful to plan before executing is something not enough executives take to heart in business. Just like cutting a piece of wood a little too long, sometimes you execute in ways that can be modified on the fly; but other times, just like the cases where you cut a piece of wood too short, you can’t. And of course, in business, sometimes it’s somewhere in between. Some examples:

• One example that’s a little more literal is around cutting staff or planning a layoff. Layoffs are traumatic for everyone involved – mostly those impacted, but for you as CEO and for your remaining organization as well. Being thoughtful about how much you cut and (unlike the case of a piece of wood) erring on the side of cutting more than you think you need to can prevent you from having to do a second set of even more traumatic layoffs down the road
  
• Getting a lease on a new office? Plan, plan, and plan again – you can end up spending too much if you get too much space and can’t sublet it…you have a real headache if you don’t get enough space and need to scramble for more
  
• Planning a major investment in a new product? You don’t want to spin up a whole new effort internally and hire people before you’ve done enough discovery and planning to know it’s worth it

It’s an interesting question as to whether or not this axiom conflicts with the startup mentality of moving quickly and with agility. I don’t think it does, although in the startup ecosystem, a lot of fixed decisioning has moved to variable, which means you may be faced with fewer times where you need to measure twice. For example, a lot of SaaS licenses you have to buy are per-seat, or AWS costs are fluid. All that is much easier than perpetual license software models or standing up servers in a data center.

I’m a big fan of Eisenhower’s line that “plans are nothing but planning is everything.” That’s why I like to measure twice, cut once when I’m working on something big. It just raises the odds of getting it right, whatever it is.

I used to describe our culture and our employees and our leaders at Return Path as a family.

That was a mistake. It was just plain wrong. It served us well in some respects, but it bit us in the ass on others.

Great groupings of people at work are teams, not families. You can have a highly functional family. But you don’t have high performing families. Work teams need to be high performing.

Here’s what I mean.

The family metaphor worked well at Return Path around the principles of caring for people and lifting each other up. Those elements of a culture are absolutely critical. I don’t regret them for a minute.

But the downside of that metaphor is that families by definition stay families. Sure, spouses can get divorced, but usually not after years of trying to make it work. And kids and parents can’t stop being relatives. Families also don’t typically have metrics and have a structural impetus to improve how they relate to each other, or to some kind of tangible output.

The practical problem with the family metaphor comes down to holding on to people too long when those people aren’t performing well. While I am a big believer that past high performance is both an indicator of future high performance and earns you as an employee a little extra grace when something goes wrong, those things can’t be absolute in business, and they have a clock on them. High performing businesses go the extra mile for their people when their people are going through a rough patch in their lives, and they should be willing to invest in coaching and development when their people need a boost or some kind of corrective action. But not indefinitely.

So even with all the caring and lifting each other up…the family is just the wrong metaphor for a business.

Here’s why the team is the right one, and I’ll use the language of sports teams here a bit more than I normally do.

Teams train together. They have a common goal, which is winning. They know that they are only as good as their weakest link. They have leaders like coaches, managers, GMs, and captains, who they look to for guidance and direction. They are disappointed when they fall short of their goals.

But — and this is the critical learning — the best teams, the highest performing teams in the world, don’t only focus on performance, metrics, and improvement. They care about their people and lift them up. Sure, there are winning teams with tyrannical bosses like the 1970s Yankees. But would you have rather been on one of the George Steinbrenner/Billy Martin teams, or worked for Joe Torre or even Joe Girardi?

The best groupings of people at work are high performing teams…AND they care about each other as people. They just don’t care about each other as people to the detriment of the team, at least not longer than a very brief cure period would allow when something goes sideways.

You can lead your organization to have the orientation of a team, with some of the best elements of families. But not the other way around.

I’ve gotten to know a number of Bolster members over the last few years, and one who I have come to appreciate quite a bit is Tim Porthouse. I’m on Tim’s email list, and with his permission, I’m reprinting something he wrote in his newsletter this month on the topic of CEO engagement in politics and current events. As you may know, I’ve written a bunch on this topic lately, with two posts with the same title as this one, Should CEOs wade into Politics (part I here, part II here). Thanks to Tim for having such an articulate framework on this important subject.

Your Leadership Game: “No Comment.”

Should you speak up about news events/ politics?

Most of the time, I say, no!

Startup CEOs feel pressure to speak up on news events: Black Lives Matter, Abortion, LBGTQ+ rights, the conflict in Israel/Palestine, Trump vs. Biden. Many tell me they feel pressured to say something, but are deeply conflicted.

Like you, I am deeply distressed by wars, murder, restrictions on human rights, bias, and hate. But if we feel something, should we say something?

Before you speak up, ask the following questions:

1.      Mission relevance. Is your startup’s success or mission on the line? Are customers or employees directly impacted? Example: It makes sense for Airbnb to advocate when a city tries to ban short-term rentals. It makes sense to advocate for your LBGTQ+ employees when a state tries to restrict their rights.

2.      Moving the needle. Will speaking out change anything? If you “denounce” something or “take a stand,” what really happens? Example: If you have employees in a state banning abortion and you tell them your startup will support them as much as the law allows, this could create great peace of mind for employees. But if your startup does not operate in Ukraine or Russia, then denouncing Russia does little (and Russia does not care!)

3.      Expertise. Do you have a deep understanding of the situation? It’s usually more complicated than it appears, especially at first. Once you speak out, you have painted yourself into a corner you will be forced to defend.

4.      Precedence and equivalence. If you issue a statement about today’s news event, will you react to tomorrow’s event? Why not? Where do you draw the line?Someone will be offended that you spoke up about X but not Y.

5.      Backlash. Are you ready to spend significant time engaging with those who disagree with you?It can get ugly quickly, and mistakes can be costly. Plus, the American public is tiring of business leaders commenting on the news.

6.      Vicarious liability. Who are you speaking for? When you say, “Our startup denounces X”?Does the whole company denounce it? You don’t know, and probably not. Does the Leadership Team? They may feel pressured to support you. What you are really saying is, “I denounce X!” OK, great, then say it to your friends and family. Leave your startup to talk about business.

If your answers are “yes,” – then speak out.

If not, I recommend keeping quiet.

In my opinion, our job is to build great companies, not debate current events.

By not speaking out, you can say, “We don’t talk politics here.” You can shut down any two-sided arguments at work and say, “Let’s get back to work,”removing a big distraction. Remember when employees protested because Google was bidding for Pentagon contracts?

I realize that you will be challenged to make a statement, that, “Saying nothing is unacceptable/ complicit.” But whoever challenges you will only be satisfied if you support their view.

If you still want to speak out, I respect your choice. Some of you will be angry with me for writing this, and I accept that. I’m asking you to think carefully before you make a statement.

Post 4 of 4 in the series of Scaling CMO’s- the other posts are, When to Hire your First Chief Customer Officer, What does Great Look like in a Chief Customer Officer and Signs your Chief Customer Officer isn’t Scaling.

You can engage with each person on the executive team one-on-one to understand what their issues and challenges are, but I’ve found that engaging with the CCO offsite with customers is far more productive and leads to a better understanding of the service organization than any other meeting time. I have typically spent the most time with or gotten the most value out of CCOs over the years doing the following.

In person at “Canary in the Coal Mine” customers. They don’t use canaries any more in coal mines, but the principle applies to companies: What are the early warning signs that you’ve got big problems looming? The earlier you discover those problems the better, and the CCO is usually the first person to figure out that something isn’t right with your product or service. I always find that the largest clients, the most demanding ones, the ones who push you around, the ones who are highly critical or you, are the ones who make your company a better company.  At Return Path, we had those types of clients over the years, from eBay, to DoubleClick, to Microsoft, to Groupon, to Facebook, to Bank of America—and that’s just the short list off the top of my mind.  The demanding customer is the one who breaks things and forces you to own up to your lack of scalability.  They also either take you to task or threaten to pull their business if you don’t clean up your act.  As painful as some of those meetings are, they are also ones I always wanted to attend in person with my CCO, both so I could eat whatever form of crow needed to be eaten as the Chief Crow Eater (which sends a very powerful message to the customer), and also because the CCO and I could experience the chirping of the canary in the coal mine and learn from the experience together.

While it’s important to engage with the CCO in the critical meetings with demanding customers, it’s also important to understand the base.  There’s an old saying from the hardware world that goes, “God was able to create the world in only 7 days because God didn’t have an installed base.”  The new world of Internet technologies, SaaS, and agile development is one where your installed base of customers is your biggest asset, not a millstone around your neck.  Some of the most meaningful experiences I had over the years with our CCOs was to be in market, spending time with all kinds of customers together in small groups and large, deeply understanding their needs and use of our product.

The CCO role is one that is easy to ignore or put on the back burner if things are going smoothly at your company, but as CEO I feel that it is best to stay close to the market and engaging with the CCO with demanding customers and with the base is a good way to understand your company and CCO better.

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

Living With Less…For Good?

Like all companies, Return Path is battening down the hatches a bit on expenses these days.  Our business is very strong and still growing nicely, but in this environment, the specter of disaster looms large, so there's no reason not to be more cautious and more profitable.

We weren't an extravagant company before this, and we never have been. But there is almost always room to save. Less travel, leaner budgets for office cafeterias, no more pilates classes in the Colorado office.  We've been very clear internally that our three priorities are protecting everyone's job, everyone's salary, and everyone's health benefits.  Hopefully things continue to go well and those can remain sacrosanct.

We are now a few months into our various cost savings plans, and it's great to see the results on the income statement and balance sheet.  More than that, it's great to see how everyone in the company is rallying around the common cause and looking for other ways to save money as well.  We've made it chic to be cheap.  And so far, there's no impact on the business. 

It will be interesting to me to see what happens on the far end of this economic badness.  It's often said the companies that make it through times like these emerge stronger on the other side, and I think I now understand why:  it's clear to me that some of the changes will work long term and some will only work short term, which means that we'll learn during this period that we can live with less. 

That doesn't mean we were profligate in the past; but it does mean that I think we are going to retrain ourselves.  We don't have to send 10 people to a big trade show to have an impact and drive the business forward.  We don't have to be the vendor who picks up the tab at the end of the night.  We don't need to pay for half the company to have cell phones (a very 1999 policy) to retain top talent.  I bet we will learn those things — and a bunch of others to come — in the next few months.

Someone asked me the other day how things are going at Bolster, the new company I started along with a bunch of long-time colleagues from Return Path last year. My visceral answer was “I’m having a blast!”  I thought about it more after and came up with five reasons why. 

First, I am working with a hand-picked group of people. My co-founders, I’ve worked with for an average of 15 years – we know and trust each other tremendously. And for the most part, the same is true about our cap table. Almost everyone else at the company is also someone multiple of us have known or worked with for years. That may not last forever, but it makes things so much easier and almost friction-free out of the gate here. 

Second, this is the “second lap around the track” for a few of us on the founding team in terms of starting something from scratch, and even those at the company who haven’t done a raw startup before are super experienced professionals and many have worked in and around early stage businesses a lot. All this combines to cut down our error rate, reduce anxiety, and speed up the pace of work. More friction-free or at least low-friction work.

Third, after a 20-year run at Return Path, it’s great to start with a clean slate. No mountains of tech debt and legacy code bases. No installed base of customers with contracts or pricing we no longer like or offer. No institutional debt like a messy cap table, legacy people issues, leases for offices we don’t want or need any more.  This also points to low friction as part of what’s going on…and while that’s a theme, the next two areas are different. 

The fourth reason I’m having a blast at Bolster is that I love — and really live in — the problem space we are working in.  When we started Return Path, I was deeply familiar with email marketing and the challenges faced by our client set and had a good vision for the early product.  But as the years went on, the product got geekier and nicher — and even when it wasn’t, I was never a USER of the product since I’m not an email marketer.  In fact, at our peak of 500 people, the company employed one email marketer and therefore had one user of our own product.  At Bolster, we have three user personas — Member, Client, and Partner.  And I’m all three of them.  I’m constantly in the product, multiple times a day.  I’m deeply familiar with all angles of the executive search and board building process.  It’s MUCH better to be this close to the product, and the same is true for many of our team members.

Finally, the thing I was really worried about with starting another company from scratch — moving from a leadership role into an individual contributor role — has been nothing short of fantastic.  I love working with clients.  I love talking to members.  I love advising and coaching CEOs. I love being a pretend product manager.  I love writing marketing copy.  It’s just great to be on the front lines. (I still love working on strategy and leading the board and engaging with people internally — but those are things that never stopped being part of my day to day.)

I was trying to think if there’s some priority to this list. Almost all of these items are or can be made to be true in your second+ startup. But while four of the five can theoretically be true in your first startup as well, I don’t think it’s quite the same. So I’d have to weight “second lap around the track” a bit higher and also note that during your second lap around the track, hand-picking your team and cap table, appreciating a clean slate, and appreciating individual contributor work are that much easier and things you can appreciate a lot more as a repeat entrepreneur.

Silly, Silly Patent Nonsense

Some news floated around the email marketing world yesterday that is potentially disturbing and destructive but highlights some lunacy at the same time.  I hope I’m getting enough of the details right here (and quite frankly that isn’t a joke, which it feels like).

Tom DiStefano of Boca-based PerfectWeb Technologies is suing direct marketing behemoth InfoUSA for patent infringement of a business process patent for bulk email distribution that he received in 2003.

I will first issue my disclaimers that I’m not a patent lawyer (nor do I even play one on TV) and that I have only quickly read both the legal complaint and the patent.  But my general take on this is that it’s more silly than anything else — but has the potential to be destructive at the same time.

Silly reason #1.  I’d like to go patent the process of blowing my nose with facial tissue predominantly using my left hand after a sneeze — will you pay me a royalty every time you do that, please?  That’s a short way of saying that I am increasingly finding that the patent system is deeply flawed, or at least very ill-suited to the way technology and Internet innovation work today.  For centuries, patents have been put in place to provide inventors adequate incentive to invest in innovation.  That made sense in a world where innovation was expensive.  It took a long time and a lot of capital to invent, say, the cotton gin or the steam engine.  It takes a long time and a lot of capital to invent a new life-saving drug.  But Internet-oriented business process patents are just silly.  It can take a guy with a piece of paper a few minutes to sketch out a business process for some niche part of the Internet ecosystem.  No real time, no real capital.  And worst of all, it’s generally easy to “design around.”  Disclaimers and all, this seems to be just such a patent.

Silly reason #2.  The patent was issued in 2003.  Really?  I’m not sure when the patent holder claims he invented the bulk email distribution process, but unless it was in the early 90s before the likes of Mercury Mail, First Virtual, Email Publishing, etc., then it’s highly likely to be “non-novel,” “obvious,” and conflicting with lots of “prior art.”

Silly reason #3.  Why wait four years to prosecute a patent that the inventor believes has been violated so obviously by so many (hundreds, maybe thousands) companies for so many years?  I don’t quite get that.

I’m not exactly seeing the David vs. Goliath here.

So here we go.  It will likely take months and millions before this thing gets resolved.  If our legal system doesn’t come through as it should, or worse, if InfoUSA punts and settles, this is going to cause big problems for many, many companies in the industry.

I hope our friends at InfoUSA are happy to dig in and fight to have the patent invalidated, although that’s expensive and time consuming.  And assuming that the patent holder is likely to go on a rampage of legal complaints against every other player in the industry — someone should tell Vin Gupta that we can all band together to fight this silliness.  We’re happy to help here at Return Path.

We live on the 35th floor of our building in Tribeca (downtown Manhattan), facing south, about 7 blocks up from the World Trade Center site. From 1994-2001, our view was grand and corporate. For a short time in September 2001, it was horrific. Since then, it’s just been depressing. Seeing such a large gap in the skyline every morning just made us remember what — and who — used to be there.

It’s not getting a lot of coverage because it’s not the Freedom Tower, but the new World Trade Center 7 building is on its way up.

As far as I’m concerned, it’s the most beautiful construction site I’ve ever seen. It’s definitely morning once again in Tribeca!

It’s election season, the GOP convention is literally in my backyard, and while this is not a political blog, I can’t help myself. As we as Americans grapple with the question of who we want to be our next leader (or at least those people who live in the 11 annointed swing states do), I have had a lot of thoughts lately about the question of what makes a good leader, and what the differences are between successful leadership in politics and successful leadership in business.

James O’Toole’s article on President Bush on page 31 of the September issue of Fast Company (no link available yet) brings up a really interesting point in comparing Bush to former president Ronald Reagan. He asserts that “what made Reagan effective and respected was that his actions followed consistently from a positive worldview.” (I’d also argue that the positive worldview as a starting point had something to do with it, but that’s beside the point.) He goes on to say that Bush has an “implementation problem” in that he “has vacillated between contradictory approaches to leadership: realism and idealism.” His central thesis is stated very clearly that

“Realists and idealists can both be effective leaders. But one cannot be both at once…The leadership lesson for GW – and for any leader – is simple: Followers don’t much care if leaders are realists or idealists, but they distrust inconsistency.”

This may or may not be true in the political arena, but I know it’s not true in business. Jim Collins’ watershed books Built to Last and Good to Great — both must reads! — describe the ideal CEO as someone who can simultaneously be optimistic and idealistic about the future of the company while simultaneously recognizing and dealing with the realities of the short-term situation. Ironically for this posting, Collins calls this the Stockdale paradox, after retired Admiral James Stockdale, a military leader and erstwhile vice presidential candidate of Ross Perot in the 1992 election.

As CEO, I have to constantly be selling the vision of the company — what we’re trying to become and how we’re going to get there — in broad strokes to my investors, board, management team, employees, and even customers. It’s that vision that keeps the whole machine running and keeps everyone focused and excited and working hard towards our long-term goals. But I have to be equally vigilant about the mundane realities of the current quarter, making our numbers, containing costs, and running the machine. If I did either one without the other, I think the whole system would break down.

Is Bush’s problem, as O’Toole asserts, that he articulated two different types of reasons for the war in Iraq — one rooted in Realism (WMD) and one rooted in Idealism (freedom and democracy)? Same goes for his states reasons for the tax cut — Realism on the one hand (to stimulate the economy) and Idealism on the other hand (shrink government). I agree that the Bush Administration has occasional implementation problems and doesn’t have nearly the “following” that Reagan and other more successful leaders in the past have, but I don’t think they’re caused by combining Realism and Idealism in the President’s leadership style. I think the leader of the free world has to do both well, each at its appropriate time, in order to be effective at his job.

Next up in this series: Admitting Mistakes.

If Only International Relations Were This Easy

Iceland is one of those weird places on earth where two continental plates meet — and you can see it. Here we are, me on the American plate and Mariquita on the Eurasian plate, with the earth seemingly coming apart at the seams in between.

If anyone’s interested in a short travelog to Iceland, here it is.