December 5, 2019

What Job is Your Customer Hiring You to Do?

My friend George, one of our co-founders at Return Path (according to him, the best looking of the three), has a wonderful and simple framing question for thinking about product strategy:  what job is your customer hiring you to do?  I am increasingly turning to that question as I work with our team on developing a new strategy for my new company, LRN. Even though LRN is in a different space, solving different problems for different buyers, I am finding George’s wisdom as relevant as ever, maybe even more so since I am still learning the new context. Why is this a useful question to ask?  It seems really simple – maybe even too simple to drive strategy, doesn’t it? It’s very easy in technology and content businesses (maybe other spaces too) to get caught up in a landslide of features and topics. In a dynamic world of competition and feature parity, product roadmaps can easily get cluttered. They can also get cluttered by product teams who have their own view of what should be the next feature, module, or content widget. Sometimes looking at product usage data is helpful, but sometimes it produces more noise than signal because it […]


October 17, 2019

The Nachos Don’t Have Enough Beef in Them!

(This is an excerpt from Chapter 23 of Startup CEO, “Collecting Data,” in which I write about the importance of observing and learning from customers and friends of the firm, as well as employees.) Here’s a story for you that happened 10+ years ago. I’m sitting at the bar of Sam Snead’s Tavern in Port St. Lucie, Florida, having dinner solo while I wait for my friend Karl to arrive. I ask the bartender where he’s from, since he has an accent. Nice conversation about how life is rough in Belfast and thank goodness for the American dream. I ask […]


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 […]


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 […]


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 […]