November 2, 2017

How Venture Capital Firms Work, for Entrepreneurs and Startups

A couple of months ago, I was doing an internal lunch & learn for senior managers, and the topic came up as to “how do our VC firms work?”  In the spirit of deeply understanding our customers’ businesses in order to better serve them, I thought the same would be true of our investors and Board members – that educating our team on the inner workings and economics of our investors would lead to greater empathy of one of our other key stakeholders. So with no small amount of help from my long-time investor and director Brad Feld and his colleague Jason Mendelson, whose book Venture Deals: Be Smarter Than Your Lawyer and Venture Capitalist I contributed to in a very small way by writing a series of sidebars called “The Entrepreneur’s Perspective” (that process led to my writing Startup CEO), I pulled together this presentation available on Slideshare entitled How Venture Capital Firms Work and Why You Should Care. I redacted our cap table and pictures of our VCs, but otherwise, feel free to use it with your own management team, or even your whole company.


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 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 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 […]


April 6, 2017

What kind of team do you run? Of Generalists and Specialists…

A friend of mine just left his job as CEO of a growth stage company to become CFO of a Fortune 500 company.  That’s a big deal…and also a big change.  When I was talking to him about the move, he said the following to me: Some executive teams are like baseball teams.  You play shortstop, and you bat 8th.  That’s just what you do.  The team needs one of those because the sport is structured that way.  The CEO of my new company likes to run his executive team as a basketball team.  Everyone has a position, but everyone also has […]


March 30, 2017

Everything is Data, Part II – Get Those Expenses In

Everything is Data, Part II – Get Those Expenses In My friend and former colleague Angela Baldonero (used to run our People Team at Return Path, now is COO of super cool startup Procurify), used to say about her job as head of HR, “Everything is Data.”  She guest blogged about that principle on OnlyOnce years ago here , and she particularly cited this theory when talking about the recruiting and hiring process. I’ve thought about this principle a lot over the years, and I’ve occasionally come up with other examples where I think peripheral data can inform whether or not […]


February 16, 2017

Reboot – Where do a company’s Values come from, and where do they go?

I’ve written a lot over the years about Return Path’s Core Values (summary post with lots of links to other posts here).  And I’ve also written and believe strongly that there’s a big difference between values, which are pretty unchanging, and culture, which can evolve a lot over time.  But I had a couple conversations recently that led me to think more philosophically about a company’s values. The first conversation was at a recent dinner for a group of us working on fundraising for my upcoming 25th reunion from Princeton.  Our guest speaker was a fellow alumnus who I’ve gotten to know […]


February 9, 2017

Book Short: Why Wait?

A Sense of Urgency, by John Kotter, is a solid book – not his best, but worth a read and happily short, as most business books should be.  I originally was going to hold off on writing this post until I had more time, but the subject matter alone made me think that was a mistake and that I should write it while it’s fresh in my mind.  <g> The three tools to fight complacency are the organizing framework for the book — bring the outside in, behave with urgency every day, and turn crises into opportunities — are all good thoughts, and […]


February 2, 2017

Book Short – A Smattering of Good Ideas that further my Reboot path

Book Short – A Smattering of Good Ideas that further my Reboot path Ram Charan’s The Attacker’s Advantage was not his best work, but it was worth the read.  It had a cohesive thesis and a smattering of good ideas in it, but it felt much more like the work of a management consultant than some of his better books like Know How (review, buy), Confronting Reality (review, buy), Execution (review, buy), What the CEO Wants You to Know ( buy), and my favorite of his that I refer people to all the time, The Leadership Pipeline (review, buy). Charan’s framework for […]