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 the Master of the Spreadsheet and who has access to a lot of data about your company.  And there is certainly a lot of value to be gained from investors with large portfolios of similar companies who can identify learnings from experience you haven’t had as a CEO and help you apply that experience thoughtfully to your company in any given situation.  In The Value and Limitations of Pattern Matching, I quoted my father-in-law, who noted once that When you hear hoof beats, it’s probably horses. But you never know when it might be a zebra.  I am still a firm believer that […]


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 […]


May 14, 2015

Give the Gift of a 360 to Your Board of Directors

Give the Gift of a 360 to Your Board of Directors I recently ran our biennial Board 360, and I thought it would be interesting to share the details.  Attached are a few pages from, my book, Startup CEO:  A Field Guide to Scaling Up Your Business  which describe the process as well as share the survey I developed, which I adapted from one that the legendary Bill Campbell uses at larger public companies like Intuit. If you’ve read this blog a lot over the years, you know that we are big on 360s for staff at all levels at Return Path , […]


April 24, 2014

Breaking New Ground on Transparency

Breaking New Ground on Transparency I’ve written a lot over time about our Live 360 process for senior leaders in the business.  (This post is a good one, and it links to a couple earlier ones that are good, as well.)  We take a lot of pride in feedback and in transparency at Return Path, and after 15 years, even for an innovative business, it’s unusual that we do something big for the first time around people.  But we did today. This image is of something never seen before at our company.  It’s my own handwritten notes about my own […]


March 20, 2014

Secrets to Yawn-Free Board Meetings

Secrets to Yawn-Free Board Meetings [This post first appeared as an article in Entrepreneur Magazine as part of a new series I’m publishing there in conjunction with my book, Startup CEO:  A Field Guide to Scaling Up Your Business] The objective of board meetings should always be to have great conversations that help you and your executive team think clearly about the issues in front of you, as well as making sure your directors have a clear and transparent view of the state of the business. These conversations come from a team dynamic that encourages productive conflict. There’s no sure-fire […]


November 7, 2013

Getting the Most out of Your Investors

Getting the Most out of Your Investors Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures.  We’ve been through a lot of wars together.  In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class.  The first two posts were mine on selecting investors and Fred’s on selecting investments.  This is my second one…and Fred’s post on the other […]


October 31, 2013

Selecting Your Investors

Selecting Your Investors Fred Wilson has been a venture investor and director in Return Path since 2000, first with Flatiron Partners and then with Union Square Ventures.  We’ve been through a lot of wars together.  In a couple of weeks, he and I are team-teaching a class in Entrepreneurship at Princeton, and the professor gave us the assignment of writing two pairs of blog posts to tee up discussion with the class.  This is the first one…and Fred’s post on the other side of the topic is here.  Next week, we’ll address the topic of building a successful CEO-VC partnership […]


May 1, 2013

Return Path’s Newest Board Member: Jeff Epstein

Return Path’s Newest Board Member: Jeff Epstein I’ve written before about how much I love my Board. Well, I’m pleased to announce I have a new reason to love it – today, I’m officially welcoming Jeff Epstein to the Return Path Board of Directors. He is joining an all-star cast that includes Greg Sands, Fred Wilson, Brad Feld, Scott Weiss and Scott Petry. I first met Jeff back in 2000 when, as CFO of DoubleClick, he and DoubleClick CEO Kevin Ryan agreed to invest in Return Path as our first institutional investor, along with Flatiron Partners.  He is one of […]


February 2, 2012

What Makes an Awesome Board Member

What Makes an Awesome Board Member (This post was requested by my long-time Board member Brad Feld and is also running concurrently on his blog today) I’ve written a bunch of posts over the years about how I manage my Board at Return Path.  And I think part of having awesome Board members is managing them well – giving transparent information, well organized, with enough lead time before a meeting; running great and engaging meetings; mixing social time with business time; and being a Board member yourself at some other organization so you see the other side of the equation.  […]


December 20, 2011

Transparency Rules

Transparency Rules I think each and every one of our 13 core values at Return Path is important to our culture and to our success.  And I generally don’t rank them.  But if I did, People First is a leading contender to be at the top of the list. The other leading contender would be this last one in the series: We believe in being transparent and direct The big Inc. Magazine story about us last year talked a lot about our commitment to transparency and some of the challenges that come with being transparent and direct with people. I’d like […]


October 7, 2011

Must-Read New Blog

Must-Read New Blog I’ve talked about Why I Love My Board a few times in the past.  I was reminded at my quarterly Board meeting and dinner this week that it’s a great and unusually strong group, and we’re lucky to have them.  Fred and Brad have both been prolific bloggers for years,and I know many of you follow their blogs closely.  Think of that as getting a taste of the input and wisdom you’d get by having them on your Board. In a very exciting development, one of my independent directors, Scott Weiss, has now started blogging on the […]