Category

Startup CEO

Sabbaticals

I’ve written a few times over the years about our Sabbatical policy at Return Path, including this post and this post about my experience as CEO when one of my direct reports was on his sabbatical, and this post about my own sabbatical. People ask me this all the time, so I thought I’d write the policy out here.  This is the language in our employee handbook about them: You have big dreams. We know. This is your chance to cross something off your life list. Whether it’s climbing Mt. Everest, learning Russian or taking your kids across the country in a Winnebago, we believe in rewarding longevity at Return Path and know that a good long break will leave…

5 Ways to Get Your Staff on the Same Page

5 Ways to Get Your Staff on the Same Page [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] When a major issue arises, is everybody at your company serving the same interests? Or is one person serving the engineering team, another person serving the sales team, one board member serving the VC fund, another serving the early-stage “angels” and another serving the CEO? If that’s the case, then your team is misaligned. No individual department’s interests are as important as the company’s. To align everyone behind your company’s interests, you must first define and…

Onboarding vs. Waterboarding

Onboarding vs. Waterboarding One of our new senior hires just said to me the other day that he has been enjoying his Onboarding process during his first 90 days at Return Path and that at other companies he’s worked at in the past, the first few months were more like Waterboarding. At Return Path, we place a lot of emphasis on onboarding – the way we ask employees to spend their first 90 days on the job.  I’ve often said that the hiring process doesn’t end on the employee’s first day.  I think about the employee’s first day as the mid-point of the hiring process. The things that come after the first day — orientation (where’s the bathroom?), context-setting (here’s…

Debunking the Myth of Hiring for Domain Expertise vs. Functional Expertise

Debunking the Myth of Hiring for Domain Expertise vs. Functional Expertise As a CEO scaling your business, you’ll invariably want to hire in new senior people from the outside.  Even if you promote aggressively from within, if you’re growing quickly enough, you’ll just need more bodies.  And if you’re growing really fast, you will be missing experience from your employee base that you’ll need to augment. For years, I’ve thought and heard that there’s a basic tradeoff in hiring senior people — you can hire someone with great domain expertise, or you can hire someone with great functional expertise, but it’s almost impossible to find both in the same person, so you need to figure out which is more important…

Startup CEO “Bibliography”

Startup CEO “Bibliography” A couple people who read Startup CEO:  A Field Guide to Scaling Up Your Business asked me if I would publish a list of all the other business books I refer to over the course of the book.  Here it is — I guess in some respects an all-time favorite list for me of business books. The Lean Startup by Eric Ries The Four Steps to the Epiphany by Steven Gary Blank Running Lean by Ash Maurya The Entrepreneur’s Guide to Customer Development: A Cheat Sheet to the Four Steps to the Epiphany by Brant Cooper and Patrick Vlaskovits Profitable Growth Is Everyone’s Business by Ram Charan The Innovator’s Dilemma by Clay Christensen The Innovator’s Solution by…

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 side of the topic is here. Once you’ve done a venture financing and the smoke clears, you have to transition…

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 once it’s established. If you’re fortunate enough to have built a really strong early stage company, you will find yourself…

The Boomerang Club, or How to Quit Your Job, Part II

The Boomerang Club, or How to Quit Your Job, Part II My post last week on How to Quit Your Job has generated about two dozen comments as well as a really lengthy thread on Y Combinator’s Hacker News.  My various replies to comments are worth summarizing here – this is a reprint of my comment on Hacker News: First, my post was not intended to be general advice to employees of all companies on how to handle a situation where they’re starting to look for jobs.  Of course, many environments would not respond well to that approach.  My point was just that that’s how we encourage employees to handle the situation at Return Path, and we have created a…

How to Quit Your Job

How to Quit Your Job I sent an email out to ALL at Return Path a few years ago with that as the subject line.  A couple people suggested it would make a good blog post in and of itself.  So here’s the full text of it: ALL – This may be one of the weirdest emails you’ll see me (or any CEO write)…but it’s an important message that I want to make sure everyone hears consistently.  If nothing else, the subject line will probably generate a high open rate.  🙂 First off, I hope no one here wants to leave Return Path.  I am realistic enough to know that’s not possible, but as you know, employee engagement, retention, and…

Startup CEO (OnlyOnce- the book!), Part IV – Book Launches Today!

Startup CEO (OnlyOnce- the book!), Part IV – Book Launches Today! My book is officially on sale on Amazon and iTunes today.  The full detailed outline is here if you’re interested, and the link to buy it is here. This is very exciting.  I had been saying for a while that I had no idea whether 50 people would buy it or 5,000, but the publisher (Wiley) tells me we had over 2,000 pre-orders, so that’s a great start, at least. So thanks to those 2,000 brave souls, and anyone else who buys it as well.  I hope you enjoy it and look forward to your feedback directly, via OnlyOnce, via the #StartupCEO hashtag, via a rating/review on Amazon, or…

Unknown Unknowns

Unknown Unknowns There are known knowns. These are things we know that we know. There are known unknowns. That is to say, there are things that we know we don’t know. But there are also unknown unknowns. There are things we don’t know we don’t know.”   –Donald Rumsfeld Say what you will about Rumsfeld or the Iraq war, but this is actually a great and extensible quote.  And more to the point, I’d say that one of the main informal jobs of a CEO, sort of like Connecting the Dots in that it’s not one of the three main roles of a CEO) is to understand and navigate known unknowns and unknown unknowns for your organization (hopefully you already understand…