Jul 262018

Sometimes a Good Loss is Better than a Bad Win

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.

Aug 272015

The Joy of Coaching

I was the head coach of my two older kids’ little league team this past spring.  The whole thing was a little bit of an accident – I vaguely volunteered for something and ended up in charge.  The commitment was a little daunting, but I was ok with it since the season was only a couple months long, it was both Casey and Wilson, and both kids, especially Wilson, are really into baseball.  Other than helping out a bit here and there, I’d never coached a sports team before.

What started off as an unclear assignment ended up as one of the most fun and fulfilling things I’ve done in years.  I loved every minute of it, looked forward to our practices and games, was hugely bummed out when we got rained out, and never had a moment where I couldn’t make the time for it (though clearly the hours had to come from somewhere!).  Given some of the overlap between leading a sports team and leading a company, I thought I’d reflect on the experience a bit here.  There are some common themes between this post and something I wrote years ago, Parenting and Corporate Leadership, with the same caveat that no, I don’t think employees are children or children are employees.  But here are some things I take away from the experience and apply or compare to work.

We established a clear philosophy and stuck to it.  That’s a step that lots of coaches – and managers in the workplace – miss.  The other coaches and I discussed this before the first practice, agreed on it, and shared it directly with the kids.  For this age group in particular, we felt that we were there first and foremost to have fun; second to learn the game; and third, to play hard and fair.  Note there was nothing in this about winning, and that we were really specific about the order of the three objectives.  Even 7 and 8 year olds know the difference between “win at all costs” and “have fun and play ball.”  We reinforced this at every practice and at every game.  Being intentional about a philosophy and communicating it (and of course sticking to it) are key for any leadership situation.

We got lucky.  As I repeatedly said to the parents on the team, we had a group of awesome kids – happy and generally paying attention, and not one troublemaker in the bunch; and we had a group of awesome parents – responsive, supportive, and not a single complaint about what position a kid was playing or where someone was in the batting order.  I’d heard horror stories about both kids and parents from other coaches ahead of time.  It’s possible that the other coaches and I did such a good job that both kids and parents were great all the time…but I think you have to chalk most of that up to the luck of the draw.  Work isn’t all that different.  Having stakeholders who are consistently positive forces is something that sometimes you can shape (you can fire problematic employees) but often you can’t, in the case of customers or even Board members.  Luck matters.

Stakeholder alignment was a critical success factor.  Having said that, I do think the coaches and I did a good job of keeping our stakeholders aligned and focusing on their needs, not ours.  We put extra effort into a regular cadence of communication with the parents in the form of weekly emails and a current web site.  We used those emails to highlight kids’ performance and also let parents know what we’d be working on in practice that week.  We made sure that we rotated kids in the batting order so that everyone got to bad leadoff once and cleanup once.  We rotated kids so that almost every kid played half of each game in the infield and half in the outfield.  We took any and all requests from kids who wanted to play a specific position for a few innings.  Many of these basic principles – communicating well, a clear operating system, listening to stakeholders, a People First approach – are lessons learned from work as a CEO.

Proper expectations and a large dose of patience helped.  After the first couple games, we were 0-2, and I was very frustrated.  But I reminded myself that 7 and 8 year olds are just kids, and my frustration wasn’t going to help us achieve our objectives of having fun and learning the game.  So I recalibrated my expectations and took much more of a laid-back attitude.  For example, any time I saw one kid goofing off a little bit in practice, I gently got him or her back in line.  But when I saw multiple kids’ attention fading, I took it as a sign that whatever I was doing as a coach wasn’t working, called a break, and did something else.  This kind of “look in the mirror” approach is always helpful at work, too.

Reward and recognition were key.  We definitely adopted a Whale Done! approach with the kids.  We got the kids in the dugout fired up to cheer on batters.  First base coaches did big high fives, smiles, and literal pats on the back for every hit.  Post-game huddles and emails to parents focused on highlights and what went right for the kids.  One of my favorite moments of the season was when one player, who only had one hit all year and struck out almost every time at bat, had two hits, an RBI, and a run scored in our final game.  Not just the coaches, but the other kids and all the parents went absolutely BANANAS cheering for this player, and it brought huge smiles to all our faces.  I am 100% certain that the focus on the positive encouraged the kids to try their hardest all season, much as I believe that same philosophy encourages people to take risks and work hard at the office.

The biggest thing I take back to the workplace with me from the experience.  I was reminded about how powerful achieving a state of “flow,” or “relaxed concentration” is.  I recounted these principles in this blog post from a couple different books I’ve read over the years – Mihaly Csikszentmihalyi’s Flow and Tim Gallway’s Inner Game books – Golf, Tennis, and Work.  The gist of achieving a state of flow is to set clear goals that are stretch but achievable, become immersed in the activity, pay attention to what’s happening, and learn to enjoy immediate experience.  All leaders – in sports, business, or any walk of life – can benefit from this way of living and leading.

I loved every minute of coaching.  It helped that we ended up with a really strong record.  But more than that, building relationships with a bunch of great kids and great parents was fun and fulfilling and incredibly thankful and rewarding.  The “thank you ball” that all the kids autographed for me is now a cherished possession.  Working and getting extra time with my own two kids was the icing on the cake.  All I want to know is…is it time for next season yet?  I am ready!

This post is really for Coaches Mike, Paul, and Oliver; and players Emily, Casey, Lauryn, Mike, Josh, Holden, Hudson, Wilson, Drew, Kevin, Matthew, and Christian.

Nov 112008

Why Do I Have to Be Frisked to Go to an NFL Game?

Why Do I Have to Be Frisked to Go to an NFL Game?


I am freaked out about terrorism as much as the next person, but our obsession with security has gone too far.  Some of the airport-related security is dumb enough — I can’t hijack a plane with my shampoo any more — but at least there’s some logic to the general premise.


But the major pat-down I got last weekend when I went to see the Chargers beat the Chiefs was just silly.  It certainly didn’t make me feel more secure sitting in the stadium.  It wouldn’t have even occurred to me to feel insecure in the first place. 


The experience reminded me of all the medium-security office buildings in New York City.  What does signing-in really do for the building’s safety?  If you want to x-ray people and their bags on the way in, fine.  But a quick visual scan of my drivers’ license and asking me to write in which floor I’m going to…what does that actually do?


And in the meantime, my understanding is that 95% of cargo containers coming into our ports still go uninspected.  Go figure.

Sep 222008



This past weekend was a weekend of closure for me. As I prepare to leave the city after almost 17 years and the apartment I’ve lived in for almost 15, we had my two original roommates from this apartment in town for the weekend with their families for a bit of a farewell party. Times certainly have changed – from three single guys to three families and 7, almost 8 kids between us. Sitting around and noting that all three couples had either gotten engaged or first started dating within the confines of Apartment 35B, then saying goodbye as everyone left the apartment for the last time, was a little surreal. But overall, having everyone around was great fun and was a fitting way to mark the occasion.

If that wasn’t enough to drive the point home, we were lucky enough to get tickets to the Yankees game last night, which was the last home game the Yanks will play in their 85-year old stadium before moving across the street next season to their fancy new home. The ceremony before the game, which featured a bunch of prominent Yankee greats and their progeny (Babe Ruth’s daughter threw out the opening pitch!), was similarly surreal, but a fitting ending to a long-standing tradition.


Why is closure important? I’m not a psychologist, but for me and my brain anyway, celebrating or formally noting the END of something helps move on to the BEGINNING of the next thing. It helps compartmentalize and define an experience. It provides time to reflect on a change and WHY it’s (inevitably) both good and bad. And I suppose it appeals to the sentimentalist in me.

I think it’s important to create these moments in business as well as in one’s personal life. We and I have done them sporadically at Return Path over the years. Moving offices as we expand. Post-mortems on projects gone well or badly. Retrospectives with employees who didn’t work out, sometimes months after the fact. Whether the moment is an event, a speech at an all-hands meeting, or even just an email to ALL, one of the main jobs of a leader in building and driving a corporate culture is to identify them and mark them.

Aug 252008

Half as Long, One Third as Hard

Half as Long, One Third as Hard

(Post written on Saturday, August 23.) I ran the Mesa Falls Marathon & Half Marathon near our house in Teton Valley, Idaho today.  I ran the 1/2 and Brad ran the full marathon as part of his quest to run 50 marathons, one in each state, by the time he turns 50.  Return Path is a proud sponsor of Brad’s running, donating $1,000 for each race he completes to the Accelerated Cure project for Multiple Sclerosis.

Brad chronicled the race here.

The run was set up well for us.  I wasn’t up for training for a full marathon, and this race had a half marathon that started at the halfway point of the full race, 2 hours after the start of the race.  So I waited a few minutes with Amy at that point until Brad came cruising by us, and then he and I ran it in together.  I was in charge of keeping him fresh and focused during a big hill and when he hit the proverbial wall.

As usual, the 26.2 mile run is an awe-inspiring distance.  Even more so running the second half of it with Brad today when I had fresh legs at the beginning and he had already done 13.1 miles.  My conclusion, based on my training, my strength at the finish, and the way my legs feel at the moment (pre-Advil and pre-cocktail), is that a half marathon is a nice accomplishment, but it’s not 1/2 as hard as a full marathon.  It’s probably about 1/3 as hard.  I’m sure there’s some great CEO metaphor about doing something halfway with a third of the effort, but I can’t conjure it up at the moment. 

So hats off to Brad on completing #12 in his amazing series. I was delighted to have my favorite people in the world meet me at the finish line, shown herePost_finish_with_family_and_brad  with Amy taking our picture.  (Yes, for those who are wondering, we are expecting #3 in January.) 

Also, Happy Birthday to my colleague Brian Westnedge, who was born in Ashton, Idaho (right near Mesa Falls) a bunch of years ago on the race day of all days.

Jun 192008

Run, Brad, Run!

Run, Brad, Run!

A few years ago we announced our support of a charity called the Accelerated Cure Project for Multiple Sclerosis (see the post about it here and learn more about Accelerated Cure here).  While we have a strong culture of giving back to the community at Return Path and do that in several ways, we chose this charity as the main beneficiary of our corporate philanthropy efforts for three reasons:

  1. We wanted to support research into finding a cure for MS to honor and support one of our earliest colleagues, Sophie Miller Audette who was diagnosed with MS about 5 years ago (and is still going strong as one of our key sales directors!) – and since then, two other members of the Return Path extended family have also been diagnosed with MS
  2. We wanted to support an organization with a focused mission and one where our contributions could really make a difference
  3. Accelerated Cure has a very entrepreneurial, innovative culture that’s consistent with our own – and a solution-oriented approach to their cause that resonates with our business philosophy

We got introduced to Accelerated Cure by Brad Feld, one of Return Path’s venture investors, who is a friend of Art Mellor, Accelerated Cure’s founder and CEO.  Brad’s an interesting guy for many reasons, but one reason is that he has a goal of running 50 marathons (one in each state) by the time he’s 50.  He has eight years and 40 marathons to go, and to make it a little more significant he decided to try and drum up some sponsorships for his quest and donate the money to Accelerated Cure. 

Return Path has decided to be one of Brad’s anchor tenant sponsors by pledging $1,000 for every race he completes.  This is half of Brad’s goal of $2,000 per race, and we hope it will inspire others to donate so he can beat his goal.  Of course, Brad wants to do more than just run these marathons – he wants to, well, accelerate his performance.  So, taking a page out of the VC handbook, we’re setting up an incentive program for Brad of an additional $500 donation for every race that he completes in less than four hours. 

Besides liking both Brad and Accelerated Cure, this particular vehicle for donating money is especially meaningful to us.  A good number of Return Path employees past and present have run marathons and even competed in triathlons and Ironman competitions (including yours truly, but in a way that certainly makes me want to keep my day job).  And Seth Matheson, Accelerated Cure’s new development director who has MS, is an avid marathoner who is contemplating an Ironman competition himself.  And as I always tell our team members, running a startup is a marathon, not a sprint!

You can follow Brad’s progress – and make a donation yourself – here.

Filed under: Leadership, Sports

Nov 072005

Only Twice? or The Un-Big Sur Marathon

Only Twice? or The Un-Big Sur Marathon

Well, it wasn’t pretty, but Brad and I finished the 36th running of the New York City Marathon yesterday.  Here we are shortly after the end.

Matt_and_brad_at_marathonThis was my second marathon.  When I finished Big Sur in 1996 with my friend Karl Florida, I had a nagging feeling that I’d do another one someday and figured it should be New York given how long I’ve lived here and what a great race it is.  From where I sit today, it’s hard to imagine doing another one.  Finishing is a truly great feeling, but boy is it a lot of work to get ready for it (not to mention a fair amount of pain both getting ready for it and doing it!).  Brad’s nuts — I say this with the utmost admiration — he’s in the process of doing 50 marathons, 1 in each state, mostly over the next 10 years.

The whole thing was incredible.  37,000 runners is just a sea of people.  There was never a point on the course when the field really thinned out – all you could see as a runner, in either direction, was just miles of heads bobbing up and down.  The crowd was amazing.  The New York Roadrunners Club estimates that 2 million people turn out to watch the marathon somewhere along the course, and I believe it.

The race was truly the opposite of the Big Sur Marathon, though.  Big Sur was silent, serene, and picturesque, with about 3,000 runners and zero spectators until about mile 24.  Yesterday’s race was raucous, crowded, and while Central Park and 5th Avenue were nice, you’d be hard pressed to call some of the sections of Queens and The Bronx we ran through picturesque.

Anyway…back to limping around the office today!