May 18, 2017

Being a CEO is Like Playing a Game of Hearts

Hearts was one of my favorite card games in college.  I remember staying up deep into the night regularly with my roommates playing it.  I recently taught our kids how to play and have been playing with them more regularly of late…and I was reminded how much I enjoy the game.  No metaphor or simile is perfect, and this one isn’t either, but it occurred to me the other night that being a CEO is a little bit like playing a game of Hearts. First and foremost, you have to play the hand that you’re dealt.  No matter how proactive you want to be about running your own agenda, things happen around you — with your people, your customers, your competitors, and you have to figure out how to react to situations. Second, you usually get to pass 3 cards to another player, but sometimes you have a “hold” hand.  Even within a situation you have to react to, sometimes you can mute the edges of it before you actually react (but occasionally, you can’t change the situation at all).  Consider the difference between a customer telling you they are about to churn (maybe you can still save them on […]


April 17, 2017

A Two Week Vacation is More Than Twice As Good As a One Week Vacation

I’ve said this for years, but as I sit on the train commuting into work after a week off relaxing with my family for my Dad’s 75th birthday (or as he prefers to call it, the 46th anniversary of his 29th birthday), I feel particularly inclined to write it up! I love my job, so I almost never mind going to work. But I also love being on vacation and traveling with my family and try to do as much of it as I can. Years ago before we had kids and became tethered to school and sports schedules, we […]


January 28, 2016

Ideas Matter Less Than Execution Which Matters Less Than Timing Which Matters Less Than Luck

Well, that’s a mouthful.  Let me break it down. Ideas Matter Less Than Execution Execution Matters Less Than Timing Timing Matters Less Than Luck There’s a persistent myth about entrepreneurs as heroes – the people with the brilliant ideas and Eureka moments that bring companies to life and create success.  I’ve never believed in that myth, or at least not in its universality, as I’ve always valued both ideation and execution in terms of business building.  But as I was thinking about that construct more the other day, it occurred to me that there’s actually a hierarchy of the two, […]


January 7, 2016

The Illusion and (Mis)uses of Certainty

September’s Harvard Business Review had a really thought-provoking article for me called How Certainty Transforms Persuasion.  Seth Godin wrote a blog post around the same time called The Illusion of Control.  The two together make for an interesting think about using information to shape behavior as leaders.  I’ve often been accused of delivering too many mixed messages to the company at all-hands meetings, so I enjoyed the think, though not in the way I expected to. Let’s start with Seth’s thesis, which is easier to get through.  Essentially he says that nothing is certain, at best we can influence events, we’re never […]


December 6, 2015

Sweet Sixteen (Sixteen Candles?)

Today marks Return Path’s 16th anniversary.  I am incredibly proud of so many things we have accomplished here and am brimming with optimism about the road ahead. While we are still a bit of an awkward teenager as a company continuing to scale, 16 is much less of an awkward teen year than 13, both metaphorically and actually. Hey – we are going to head off for college in two short years! In honor of 16 Candles, one of my favorite movies that came out when I was a teenager, I thought I’d mark this occasion by drawing the more obvious comparisons […]


November 12, 2015

You Have To Be All In, Until You’re Not

One of the things I’ve learned over the years is that as the organization scales, you have to be all-in, until you’re not.  What the heck does that mean? It means that, other than confiding your indecision to a very small number of trusted advisors on a given issue, indecision is poison to the people around you and to the organization in general.  So even if you’re thinking of doing something new or different or making a tough call on something, you generally need to project confidence until you’ve made the call. One example of this is around a decision […]


September 17, 2015

The Playbook

As Return Path gets older, we are having more and more alums go on to be successful senior executives at other companies – some in our space, some not.  It’s a great thing, and something I’m really proud of.  I was wondering the other day if there’s effectively some kind of “RP Playbook” that these people have taken with them.  Here’s what I learned from asking five of them. People-related practices are all prominent as part of the Playbook, not surprising for a People First company.  Our Peer Recognition program, which is almost as old as the company and has […]


August 27, 2015

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 […]


August 19, 2015

ReturnShip Program, Part III

I’ve written a couple times this past year about our ReturnShip program, which is a 4-month paid internship program designed for women who have been out of the workforce for more than 3 year to re-enter and  build credible and relevant experience, and to expand the talent pool for our organization.  I wrote about the initial concept when we launched v2 of the program, and then again when v2 concluded with the hiring of four of the six participants. I’m immensely proud of our organization for inventing the program (Andy Sautins, our CTO, gets credit) and for managing it so […]


April 29, 2015

ReturnShip Program, Part II

Today marks the graduation for the six women who participated in our inaugural ReturnShip program, which I wrote about here and which was written up at least twice, in Harvard Business Review and in the San Francisco Chronicle. The ReturnShip was a 14-week paid internship program designed for women who have been out of the workforce for more than 1 year to re-enter and  build credible and relevant experience, and to feed our funnel of prospective employees. While there are still a couple things in the air, my guess is that at least three, and as many as five, of […]


December 5, 2014

35 at 15

This was a big week for Return Path.  First we announced a $35mm financing led by Vista Equity Partners, an exceptional private equity firm that I’d never heard of before the middle of the fundraising process a few months ago.  We are happy to have them join our very strong board and syndicate and even happier to have additional investment capital to accelerate our growth, especially in newer businesses for us like Email Fraud Protection and our overall data and analytic capabilities. But in some ways even more important, or at least more sentimentally important news this week is that tomorrow, December 6, marks the […]