I just said this to a fellow little league coach, and it’s certainly true for baseball.  I’ve coached games with sloppy and/or blowout wins in the past.  You take the W and move on, but it’s hard to say “good game” at the end of it and feel like you played a good game.  And I’ve coached games where we played our hearts out and made amazing plays on offense and defense…and just came up short by a run.  You are sad about the L, but at least you left it all out on the field.

Is that statement true in business?

What’s an example of a “bad” win?  Let’s say you close a piece of business with a new client…but you did it by telling the client some things that aren’t true about your competition.  Your win might not be sustainable, and you’ve put your reputation at risk.  Or what about a case where you release a new feature, but you know you’ve taken some shortcuts to launch it on time that will cause downstream support problems?  Or you negotiate the highest possible valuation from a new lead investor, only to discover that new lead investor, now on your Board, expects you to triple it in four years and is way out of alignment with the rest of your cap table.

On the other side, what’s an example of a “good” loss?  We’ve lost accounts before where the loss was painful, but it taught us something absolutely critical that we needed to fix about our product or service model.  Or same goes for getting a “pass” from a desirable investor in a financing round but at least understanding why and getting a key to fixing something problematic about your business model or management team.

What it comes down to is that both examples – little league and business – have humans at the center.  And while most humans do value winning and success, they are also intrinsically motivated by other things like happiness, growth, and truth.  So yes, even in business, sometimes a good loss is better than a bad win.

Book Short:  Entrepreneurs in Government

Leadership and Innovation:  Entrepreneurs in Government, edited by a professor I had at Princeton, Jim Doig, is an interesting series of mini-biographies of second- and third-tier government officials, mostly from the 1930s through the 1970s.  The book’s thesis is that some of the most interesting movers and shakers in the public arena (not elected officials) have a lot of the same core skills as private sector entrepreneurs.

The thesis is borne out by the book, and the examples are interesting, if for no other reason than they are about a series of highly influential people you’ve probably never heard of.  The guy who ran the Port Authority of New York for 30 years.  The guy who built the Navy’s fleet of nuclear submarines.  The head of NASA who put a man on the moon.

The biggest gap I identified between the success of these individuals and business entrepreneurs is the need for cultivation of direct relationships with congressional leaders, true in almost all cases.  I’m not sure there’s a proper analog — shareholders, maybe — but that’s clearly a skill that is required for the heads of agencies to succeed with their political patrons.

It’s an interesting read overall, particularly if you’re an entrepreneur who is considering a future career change into government.

7 Years On

My last September 11 as a New York City resident. I walked down to the World Trade Center site this morning as I have each of the last six 9/11s and rang The Bell of the Unforgotten, which is the New York City Fire Department’s port-a-memorial that they bring out for the day. As a long-time member of the lower Manhattan community, the day always bring out a lot of reflection for me. Seeing the memorial flood lights on tonight will do the same and bookend the day.

The main thing I was thinking about this morning was why there’s been nothing really built yet on the site. World Trade Center 7 (which is actually adjacent to the main site) went up in a hurry a few years ago (pictured here under construction four years ago), but nothing else.

My general understanding of the situation is that the holdup has not been around clean-up or pre-construction the last several years, but all about legal, political, and insurance issues. And that smacks to me of a leadership problem. I realize there are a lot of parties involved, and a lot at stake, but it’s just embarrassing to America that we haven’t rebuilt the site — and fast. Set an example to the rest of the world that we react swiftly and don’t let the bad guys knock us down…and keep us down.

It feels to me like a President who actually understood leadership would have gotten all the parties in a room together and not let them out until there was agreement on a plan. Don’t just let “the system” play things out laissez faire, but actually play them out in a hurry so the country and city can move forward. It feels like the kind of thing Reagan or Clinton would have done.

As I reflect on this today, the one thing I’m happy about is that no matter who wins the White House, America will be getting a leadership upgrade.

Calling for the Boss’s Head

Maybe it’s just a heightened sense of awareness on my part, but I feel like our culture has really turned up the time-to-fire-the-boss-o-meter to a new level of late.  What is going on that has caused the media and vocal people among us feel this thirst for public lynchings over a single incident?  The list isn’t small — just in recent weeks or months, you have Rumsfeld, Dunn (HP), Gonzales, Imus, Wolfowitz, and even last week, Snyder (Vonage).  And I’m sure there are a dozen others, both corporate and political, that I’m not dredging up mentally here on a Sunday night.

Now I’m all for accountability, believe me, but sometimes it doesn’t help an organization for someone to resign at the top over a single incident.  Jarvis says it best when he says that he would have fired Imus a long time ago because he’s boring and because he’s always been a racist, not because of a few choice words last week.  Should chronic poor performers be dismissed regardless of level?  Absolutely.  Should a leader be forced to step down just to make a point?  I’m much less certain.  In some ways, to carry Jarvis’s theme forward, that kind of dismissal is just a sign to me of lackadaisical oversight along the way, finally coming to a head.

I’m no psychologist, but my guess is that in many cases, a flash dismissal of another otherwise competent leader can pretty bad and traumatic for the underlying organization (be it a company or country).  Consider the alternative — an honest apology, some kind of retribution, and a clear and conspicuous post-mortem — that leaves the ship with its captain and sends the message to the troops that honest mistakes are tolerated as long as they’re not repeated and amends are made.

This in no way is meant to defend the actions of any specifics of the above list.  For many of them, their actions may have prompted an unrecoverable crisis of confidence.  But for my part, I’d rather see regular accountability and transparency, not just at the peaks and troughs.

An Execution Problem

My biggest takeaway from the TED Conference this week is that we — that is to say, all of us in the world — have an execution problem.  This is a common phrase in business, right?  You’ve done the work of market research, positioning, and strategy and feel good about it.  Perhaps as a bigger company you splurge and hire McKinsey or the like to validate your assumptions or develop some new ones.  And now all you have to do is execute — make it happen.  And yet so many businesses can’t make the right things happen so that it all comes together.  I’d guess, completely unscientifically, that far, far more businesses have execution problems than strategic ones.  Turns out, it’s tough to get things to happen as planned BUT with enough flexibility to change course as needed.  Getting things done is hard.

So what do I mean when I say that humanity has an execution problem?  If nothing else, the intellectual potpourri that is TED showed me this week that we know a lot about the world’s problems, and we don’t lack for vision and data on how to solve them.  A few of the things we heard about this week are the knowledge — and in many cases, even real experiences — about how to:

– Steer the evolution of deadly disease-causing bacteria to make them more benign within a decade

– Build world class urban transportation systems and growth plans to improve urban living and control pollution

– Drive down the cost of critical pharmaceuticals to developing nations by 95%

– Dramatically curb CO2 emissions

We have the knowledge, and yet the problems remain unsolved.  Why is that?  Unlike the organized and controlled and confined boundaries of a company, these kinds of problems are thornier to solve, even if the majority of humans agree they need to be solved.  Whether the roadblock is political, financial, social — or (d) all of the above — we seem to be stuck in a series of execution problems.

The bright spot out of all of this (at least from this week’s discussions) is that, perhaps more than ever before in the history of mankind, many of our most talented leaders AND our wealthiest citizens are taking more of a personal stake in not just defining the problems and solutions, but making them happen.  They’re giving more money, buiding more organizations, and spending more time personally influencing society and telling and showing the stories.  It will take years to see if these efforts can solve our execution problems, but in the meantime, the extraordinary efforts are things we can all be proud of.

Naked Talking

Naked Conversations:  How Blogs Are Changing The Way Businesses Talk with Consumers, by Robert Scoble and Shel Israel, would have been mildly interesting had I never read, let alone written, a blog.  So chances are if you’re reading this blog regularly, it’s not a great use of your time or money, but if you just ran across this post while trying to learn more about blogging – or really about any form of post-2002 Internet marketing – it’s probably worthwhile as a primer. But if you’re knee-deep in internet marketing or blogging, it may be a bit of a snoozer.

I find it entertaining that leading bloggers like Scoble and Israel, who are part of the ultra-small group of hardcore bloggers, as they describe, that “posts 50 times a day, mostly at 4 a.m.,” think blogs are really conversations.  Don’t get me wrong, I believe that blogs are revolutionary in that they allow anyone to run his or her own printing press.  I also think it’s critical for companies to have corporate blogs (Return Path had one of the first), for CEOs and other executives to blog (obviously I do), for companies to allow their employees to blog relatively unencumbered by corporate policy, and, perhaps most important, for companies to track and listen to what others who blog are saying about them and their products.

But let’s not get too caught up in our own euphoria as bloggers to think that what’s happening is actually a conversation the way we humans think of conversations.  Blogging allows more people to have their voices heard, and it certainly allows for transparency and authenticity, as the authors say, but there’s almost never dialog.  Many popular blogs don’t have comments at all.  Those who do allow comments have few if any posted.  And those who have comments posted rarely have any other readers who actually see the comments, since the blog is a publishing forum and RSS is a publishing format, neither is a truly interactive medium like chat.

I’m sure there are some blogs that have active commenters, particularly political ones, and hopefully someone, somewhere, reads and internalizes those comments when they’re relevant. And certainly, high circ bloggers who read and know each other participate in a dialog by talking AT each other via their blog postings, not via comments (meaning that for the “dialog” to make sense to the greater world, the greater world must read all blogs participating in a “conversation.”). But, please, let’s not pretend there is really a 20-million-way conversation happening.

Book Short:  Underdog Victorious

The Underdog Advantage, by David Morey and Scott Miller, was a worthwhile read, though not a great book.  It was a little shallow, and although I enjoyed its case studies (who doesn’t love hearing about Ben & Jerry’s, Southwest, JetBlue, Starbucks?), I didn’t feel like the authors did enough to tie the details of the success of the case study companies back to the points they made in the book.

That said, the book had some great reminders in it for companies of all sizes and stages.  The main point was that successful companies always think of themselves as the underdog, the insurgent, and never get complacent.  They run themselves like a political campaign, needing to win an election every single day.  A lot of the tactics suggested are timeless and good to remember…things like never declare victory, always play offense, always respond to attacks, remember to communicate from the inside out, and remember to sell employees on a mision and purpose in order to make them your main ambassadors.  The laundry list of tactics is the book’s greatest strength.

Counter Cliche:  No Conflict, No Interest

The entrepreneur’s take on Fred’s VC cliche of the week — "No conflict, No interest" is that it applies equally but differently to management teams. 

Our nation’s first president, George Washington, is often said to have brilliantly placed political enemies Thomas Jefferson and Alexander Hamilton on his first cabinet so he would have differing points of view from which to choose when deciding some of the complex and delicate issues that faced our nation in its infancy.  And many of those early decisions of the Washington administration — things like how to pay down the debt from the Revolution, or whether and how to put down the Whiskey Rebellion — were critical in forming our nation and deciding how much power to invest in our government.

The tension between one executive and another on a management team is, though perhaps less historically important, no different.  A management team that finds itself 100% in agreement, 100% of the time, is in trouble.  A management team that can have disagreements and use that tension productively to drive decisions is much better off.  Building such a team requires the CEO to seek out executives who view the world differently, who have the courage to speak their minds in the face of strong opposition, and who have the ability to see different points of view.

I’ve always thought that the ability to stare down adversity in business — or turning lemons into lemonade, as a former boss of mine used to say — is a critical part of being a mature professional. We had a prime example of this a couple weeks ago at Return Path.

We had scheduled a webinar on email deliverability, a critical topic for our market, and the moment of the webinar had come, with over 100 clients and prospects on the line for the audio and web conference. There was a major technical glitch with our provider, Webex (no link for you, Webex), and after 5 or 10 minutes, we had to cancel the webinar — telling all 100 members of our target audience that we were sorry, we’d have to reschedule. What a nightmare! Even worse, Webex displayed atrocious customer service to us, not apologizing for the problem, blaming it on us (as if somehow it was our fault that half the people on the line couldn’t hear anything), and not offering us any compensation for the situation.

As you can imagine, our marketing guru Jennifer Wilson was devastated. But instead of sulking, she turned the situation on its head. She rescheduled the event for three weeks out with a different provider who was technically competent and a pleasure to work with, Raindance, and sent every person who’d been on our aborted webinar a gift certificate to Starbucks so they could enjoy a snack on our dime during the rescheduled event. Not only did we have full attendance at the rescheduled event, but Jennifer received dozens of emails from clients sympathizing with her, commending her on her attitude, and of course thanking her for the free latte.

It’s hard to do, and you hate to have to do it, but successfully turning lemons into lemonade is one of the most satisfying feelings in business!

People rarely comment on this blog (or most non-political blogs, I’ve noticed), so feel free to share your best lemons-to-lemonade story with me in a comment, and I promise I’ll post the best couple of them pronto!

Today, the FTC very shrewdly punted on the issue of the proposed “Do Not Email” list implementation, saying that authentication systems need to be put in place before such a list can be considered. This buys the world more time to work on more effective, market-driven solutions to the spam and false positive problems.

I read a few interesting posts on this today, including one from Jeff Nolan which nicely captured Chuck Schumer’s elegant combination of demagoguery and idiocy about this issue; and one from Anne Mitchell pointing out that they’re about six months late with their conclusion. Feels about right for the federal government.

What’s interesting to me is that all of the comments by and about the FTC and the proposed “Do Not Email” list focus on the wrong thing: they say that the problem with the list is that spammers would abuse it by hacking into it and stealing all the email addresses. Ok, I’ll admit, that’s one theoretical problem, but it’s not THE problem.

The structural problem with a national “Do Not Email” list is that responsible emailers, non-spammers, don’t need to use it since they get appropriate permission from their customers before sending them email…and spammers won’t bother using it since they don’t give a hoot anyway and will find a way around the list as they do everything else. In the end, the creation of such a list would do nothing to stop spam, but it would certainly create a lot of confusion for legitimate marketers and their customers around opting in and opting out. It would also, notably unlike the fairly successful national “Do Not Call” list, not do anything to reduce the volume of spam, which will create disappointment and anger among consumers (and hello, Senator Schumer, backfire on its political sponsors).

Those aren’t bigger problems than spam to be sure, but why should we implement a solution to the problem that doesn’t work at all and that causes its own ancillary problems along the way?

And here I am. In the middle of that “once.” Fred Wilson wrote a great posting by that title on his blog, and it has stuck with me. When I decided to start a blog, it was the first thing that came to mind as a main theme for the blog, so there you go. Only Once it is.

I’m not entirely sure why I’m doing a blog. Part of it is fascination with the newest corner of the Internet and its related areas like RSS (clicking on that link will get you the RSS feed of this blog). Part of it is to try out the medium and see how it might work for the hundreds of marketers and publishers who are my company’s clients. I suppose part of it is to generate some interest in my company, Return Path, which in my extremely biased opinion is one of the most interesting companies in the email services business.

My one hesitation about starting a blog is that the other part of me feels like blogs are a bit narcissistic, and I can’t imagine who on earth would want to read whatever it is that pops into my head. But I’ll give it a try and promise not to go overboard on the extraneous postings.

So, I will probably post periodically about experiences of an entrepreneur, of the one time I’ll ever be a first-time CEO. But I may also post on other things periodically that match my interests: book reviews, travelogs, Princeton, great wines, maybe even the occasional political commentary to prove to my predominantly New York friends that (a) not all Republicans are bad, and (b) not all Jewish New Yorkers are Democrats.

So, here we go…enjoy!