October 11, 2019

Necessity is the Mother of Leadership Innovation

About 8 years ago, I wrote a blog post that talked about the story from my MovieFone days when I went from managing 1 person to 20 overnight and had to completely rejigger my Operating System to the new environment. It was a case of required revolution over evolution for me. Trial by fire. I feel like I am living in an analogous world now. After 7 days on the job as CEO of LRN (announcement) (first days post) I am realizing that going from leading a company that I founded and led for two decades to leading a 25-year old company in a new industry is going to require some structural changes to the way I lead. For example: I will still be as “retail” as possible with my new colleagues since my natural inclination is to focus on the people in the business, but I can’t possibly get to know hundreds upon hundreds of people all at onece the way I got to know an even greater number over many years of hiring and onboarding them myself. Because I that, I will end up changing my interaction patterns with those colleagues with whom I don’t engage day in, […]


October 3, 2019

First Days

As I mentioned last week, I just started a new chapter of my career journey as CEO of LRN, a SaaS company based in New York City that provides ethics and compliance education software while advising companies on shaping values-based leadership, cultures and governance as sources of competitive advantage. That’s all good and well, but Tuesday morning, I was also a new employee walking into his office on the first day of a new job. The last time I’d done that was when I started at MovieFone in 1995 (the first day of starting one’s own company doesn’t count!). During […]


September 26, 2019

Second Lap Around the Track

Second Lap Around the Track As people who have read my blog for some or all of the last 15 years know, the theme of the blog, which is called OnlyOnce, is that “You’re only a first time CEO once” inspired by my friend, long-time board member and mentor Fred Wilson.  I always give the advice to people in business or in life that “the second lap around the track is a lot easier,” whether it’s referring to the second year of a new job, the second new job out of college, or even a second marriage.  And now I’m […]


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 […]


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 […]


July 12, 2018

How to Get Laid Off

How to Get Laid Off – an Employee’s Perspective One of my colleagues at Return Path  saw my post about How to Quit Your Job about 5 years ago and was inspired to share this story with me.  Don’t read anything into this post, team!  There is no other meaning behind my posting it at this time, or any time, other than thinking it’s a very good way of approaching a very difficult situation, especially coming from an employee. In 2009 I was working at a software security start up in the Silicon Valley.  Times were exceedingly tough, there were several […]


July 3, 2018

Response to the Journal

(This post is running concurrently on the Return Path blog.) It is now widely understood that the Internet runs on data. I first blogged about this in 2004—14 years ago!— here.  People have come to expect a robust—and free!—online experience. Whether it’s a shopping app or a social media platform like Instagram, these free experiences provide a valuable service. And like most businesses, the companies that provide these experiences need to make money somehow. Consumers are coming to understand and appreciate that the real cost of a “free” internet lies in advertising and data collection. Today, the Wall Street Journal ran an article […]


June 28, 2018

Feedback Overload and Confusion – a Guide for Commenting on Employee Surveys

We run a massive employee survey every year or so called The Loop, which is powered by Culture Amp.  We are big fans of Culture Amp, as they provide not only a great survey tool but benchmarks of relevant peer companies so our results can be placed in external context as well as internal context. The survey is anonymous and only really rolled up to large employee groups (big teams, departments, offices, etc.), and we take the results very seriously.  Every year we run it, we create an Organization Development Plan out of the results that steers a lot of […]


April 19, 2018

There’s a word or two missing from the English language

In my personal life, I have acquaintances, I have friends, and I have good/close friends. In my work life, I have colleagues – the professional equivalent of acquaintances. But what comes after that professionally?  We spend over half our waking life at work.  Of course we are going to build important relationships.  Some of them will cross over to personal and become legitimate “friends” or “good friends.” I always feel some sense of honor when a colleague introduces me to someone as a true friend. But for those that don’t cross that chasm – for those who are truly just professional […]


March 8, 2018

You Don’t Know How to Drive a Car Because You Know How to Read a Map

I was having breakfast with the CEO of another SaaS company the other day, as I often do to network.  He was telling me about his experience working with his company’s new Private Equity owner. There are always a mix of pros and cons that come with any particular shareholder, Board member, or owners, of course.  In his case, my fellow CEO was bemoaning the 29-year old associate who acted like a know-it-all in every Board meeting.  Lots of CEOs have been there.  There’s a lot of value you can get from an associate or VP-level person at an investor who is […]


February 22, 2018

No One Will Ever Thank You for Keeping Prices Low

I was in a Board meeting last week (not Return Path’s), when one of my fellow directors came out with this gem:  “No one will ever thank us for keeping our prices low.” When I first heard this, as is the case with most great quotes, I was drawn to its wit and simplicity. But then I started thinking – is it true?  My mind first went to retail.  Having a reputation as being a low-cost provider can be in and of itself effective marketing – if that reputation is strong enough and your selection is wide enough, at least […]