March 24, 2011

Size of Pie, a.k.a. What Type of Entrepreneur Are You?

Size of Pie, a.k.a. What Type of Entrepreneur Are You? Mmmm…pie.  A post that Fred had up a few weeks ago about an M&A Case study involving WhatCounts, a company in the email space that I’ve known and had a lot of respect for for years, got me thinking about two different topics.  The first is thinking about types of entrepreneurs.  I’ve always said there were two types:  serial entrepreneurs who are great at starting companies but less great at scaling them, and entrepreneurs who are often part of a group of founders but who go on to continue to run the business for the long-haul. CEO David Geller’s quote that gets to the heart of this in Fred’s post was: …a bigger piece of a smaller pie, at some point, is the same as a smaller piece of a much larger pie.  And, donʼt let anyone tell you that baking a bigger pie isnʼt a whole lot more difficult. Although David is talking about taking in outside capital and founder dilution in pursuit of larger business growth and objectives, he is also getting to the same point about entrepreneur type.  Scaling an organization beyond proof of concept, happy few […]


August 26, 2010

Style, or Substance?

Style, or Substance? I had an interesting conversation the other day with a friend who sits on a couple of Boards, as do I (besides Return Path’s).  We ended up in a conversation about some challenges one of his Boards is having with their CEO, and the question to some extent boiled down to this:  a Board is responsible for hiring/firing the CEO and for being the guardians of shareholder value, but what does a Board do when it doesn’t like the CEO’s style? There are lots of different kinds of CEOs and corporate cultures.  Some are command-and-control, others are […]


December 6, 2009

A Perfect Ten

A Perfect Ten Return Path turns 10 years old today.  We are in the midst of a fun week of internal celebrations, combined with our holiday parties in each office as well as year-end all-hands meetings.  I thought I would share some of my reflections on being 10 in the blog as I’ve shared them with our team. What being 10 means to me – and what’s enabled us to make it this long: It means we’ve beaten the odds.  Two major global economic meltdowns.  The fact that 90% of new small businesses fail before they get to this point.  […]


September 3, 2009

Ten Characteristics of Great Investors

Ten Characteristics of Great Investors Fred had a great post today called Ten Characteristics of Great Companies.  This link includes the comments, which numbered over 70 when I last looked.  Great discussion overall, especially for Fred’s having come up with the list on a 15-minute subway ride.  Fred used to write a series of posts about VC Chiches, and I would periodically write a Counter-Chiche post from the entrepreneur’s perspective.  This post inspired me to do the same. So I’ve taken 15 minutes here, pretended I’m on the subway, and here is my list of Ten Characteristics of Great Investors, […]


June 10, 2009

Poking a little fun at VCs

Poking a little fun at VCs Fred posted a great slideshow this morning of “things VCs will never say.”  I can’t tell if the show is meant to be serious or not — some of the things would be great to hear from VCs, some would be terrible — though Fred’s comment at the bottom leads me to believe he thinks it was serious. At any rate, it reminded me of the brilliant and hilarious “VC Calendar Calisthenics” post of Dave Hornick from 5-6 years ago, which you can see here.  Even if you’ve read it before, it’s worth a […]


December 6, 2008

Next One is the Big One, a.k.a. Nine is Fine

Next One is the Big One, a.k.a. Nine is Fine Today, Return Path turns nine years old.  What an exciting year we’ve had, too.  As I mentioned a couple months back, we completely reorganized the company this year, marking a major transition and a new stage in the life of the business.  We acquired our largest competitor, Habeas, consolidating our space and further establishing ourselves as the leader in email deliverability and whitelisting.  We marched right past our 1,000th client milestone and now are well on our way to our 1,500th. Thanks again to our fantastic team and our great […]


April 30, 2008

You Have to Shoot to Score

You Have to Shoot to Score Fred’s recent post called From Messes to Successes left me thinking about the reasons why successful companies often have rough patches along the road to their ultimate success — the times Fred refers to when he says “they’re a mess.”   First, his premise is right.  Good companies are often a mess.  Probably more than most outside Board members (even good VC ones) even realize!  And while his explanation as to why this occurs, which is that the company focuses exclusively on the product to the exclusion of infrastructure, scaling, and planning issues, may be […]


November 21, 2007

VCs Are Full of It

VCs Are Full of It …at least that’s what Brad says.  Well, he says a lot more than that, but certainly makes for a good pre-holiday headline, doesn’t it? Brad’s brilliant advice is not to confuse data – or even worse – anecdotes – with fact.  I’d add to the axiom my own observation that “just because someone says something with extreme conviction doesn’t mean it’s true.” His whole post is very worthwhile – one of the best ones I’ve read in a long time.  Read it here.


September 26, 2007

Lighten Up!

Lighten Up! As with Brad, I love a good rant, and Dave McClure’s wild one this week about how VCs and Lawyers Need to Simplify, Innovate, and Automate is fantastic.  I have a roughly 3 foot shelf in my office that has all the bound paper documentation for the financings and M&A we’ve done here over the years and have always felt like it’s an enormous waste on many levels.  The insanity of the faxes, zillions of signatures, original copies, and triplicates is overwhelming. But the core of the rant is a beautiful and simple suggestion that those who invest […]