December 8, 2020

Introducing the Bolster Board Benchmarking Survey

Over the years,  I’ve had a list of nagging questions every time I’ve contemplated my board, but didn’t have anyone I could turn to who had deep, broad advice on this topic. Those questions were: How big should my board be at this stage?   How many independent directors should I have?  What is the right profile of an independent director?  How many options should I give a board member?  How do I find the best, diverse, talent for my board openings? That’s why Bolster is excited to announce the launch of our first CEO tool: Board Benchmarking. This application (which is free!) is the first of a series of tools that we’re designing to help CEOs understand the performance, design, and impact of themselves, their executive teams, and their boards. The results of this first application will shed light on the independence, diversity, and compensation of private company boards that’s never been available on a broad basis before. Why are we starting with Board Benchmarking? Increasing Board Diversity is top of mind right now… …and that means CEOs need to have a handle on three things at the same time to get it right:  appropriate board size/number of independent seats, […]


December 1, 2020

The New Way to Scale a Board of Directors

As we wrote in Bolster’s Founding Manifesto, one of the reasons we started Bolster was to create a new way; a faster, easier, and more cost-effective way, for startup and scaleup CEOs to grow their boards of directors and make them more diverse. There’s a lot of research out there that the more independent a board is, the better it performs for companies — and that there’s a high degree of correlation between more independent boards and higher performing companies as well. There’s also a lot of research out there that shows that teams which have diversity of gender and […]


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 […]


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.  […]