May 1, 2019

OnlyOnce, Part XX

I realize I haven’t posted much lately.  As you may know, the title of this blog, OnlyOnce, comes from a blog post written by my friend and board member Fred Wilson from Union Square Ventures entitled You Are Only a First-Time CEO Once, which he wrote back in 2003 or 2004.  That inspired me to create a blog for entrepreneurs and leaders.  I’ve written close to 1,000 posts over the years, and the book became the impetus for a book that another friend and board member Brad Feld from Foundry Group encouraged me to write and helped me get published called Startup CEO:  A Field Guide to Scaling Up Your Business back in 2013. Today is a special day in my entrepreneurial journey and in the life of the company that I started back in 1999 (last century!), Return Path, as we announce that Return Path has entered into a definitive agreement to be acquired by an exciting new company called Validity.  Press release is here. Over almost 20 years, we’ve built Return Path into one of the largest and (I think) most respected companies in the email industry.  We’ve had a culture of innovation that has led to some […]


July 26, 2018

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 […]


December 1, 2017

Knowing When to Ask for Help in Your Startup

I had a great networking meeting yesterday along with Tami Forman, the CEO of our non-profit affiliate Path Forward, and Joanne Wilson, my board co-chair.  It was a meeting that Joanne set up that the three of us had been talking about for over a year.  Joanne made a great comment as we were debriefing in the elevator after the meeting that is the foundation of this post.  Tami and I shaped her comment into this metaphor: Finding wood to help start a fire is different from pouring gasoline on a fire As an entrepreneur, you need to constantly be […]


November 16, 2017

Deals are not done until they are done

We were excited to close the sale of our Consumer Insights business last week to Edison, as I blogged about last week on the Return Path blog.  But it brought back to mind the great Yogi Berra quote that “it ain’t over ’til it’s over.” We’ve done lots of deals over our 18 year existence.  Something like 12 or 13 acquisitions and 5 spin-offs or divestitures.  And a very large number of equity and debt financings. We’ve also had four deals that didn’t get done.  One was an acquisition we were going to make that we pulled away from during due […]


October 5, 2017

When in Doubt, Apply a Framework (but be sure to keep them fresh!)

I’ve always been a big believer in the consistent application frameworks for business thinking and decision-making.  Frameworks are just a great starting point to spark conversation and organize thinking, especially when you’re faced with a new situation.  Last year, I read Tom Friedman’s new book, Thank You for Being Late: An Optimist’s Guide to Thriving in the Age of Accelerations, and he had this great line that reminded me of the power of frameworks and that it extends far beyond business decision-making: When you put your value set together with your analysis of how the Machine works and your understanding of […]


August 31, 2017

Agile Everywhere, Part II

Over the years, I’ve written a lot about the Agile methodology on this blog. For those of you who are regular readers, you may remember a post I wrote about our Agile Everywhere initiative— where all Return Path teams were tasked with implementing agile practices. A little over a year later, I want to update you on our agile journey–where we are now and how we got there.  My colleague Cathy Hawley (our head of People) will write a more detailed series of guest posts  for those of you who want to get more details of our transformation process. Before […]


August 10, 2017

The Value and Limitations of Pattern Recognition

My father-in-law, who is a doctor by training but now a health care executive, was recently talking about an unusual medical condition that someone in the family was fighting.  He had a wonderful expression he said docs use from time to time: When you hear hoof beats, it’s probably horses. But you never know when it might be a zebra. With experience (and presumably some mental wiring) comes the ability to recognize patterns.  It’s one of those things that doesn’t happen, no matter how smart you are, without the passage of time and seeing different scenarios play out in the […]


June 29, 2017

Delegating Decision-Making

My dad (one of my main CEO/entrepreneur role models) and I team-teach a business school class in entrepreneurial leadership every year at USD where a friend of his is the professor.  Sometimes I go in person, usually I just do it by video.  We did this a few weeks ago, and my dad talked through a decision-making framework that I’d never heard him mention before. I sketched it out and really like it and am already using it internally, so I thought I would share it here as well: To walk through it, delegating decision-making to someone on your team can […]


June 12, 2017

Why You Won’t See Us Trash Talk Our Competition

We’ve been in business at Return Path for almost 18 years now.  We’ve seen a number of competitors come and go across a bunch of different related businesses that we’ve been in.  One of the things I’ve noticed and never quite understood is that many of our competitors expend a lot of time and energy publicly trash talking us in the market.  Sometimes this takes the form of calling us or our products out by name in a presentation at a conference; other times it takes the form of a blog post; other times it’s just in sales calls.  It’s […]


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 […]


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 […]