Category

Entrepreneurship

Knowing When to Ask for Help in Your Startup

I had a great networking meeting yesterday along with Tami Forman, the CEO of our non-profit affiliate Path Forward, and Joanne Wilson, my board co-chair.  It was a meeting that Joanne set up that the three of us had been talking about for over a year.  Joanne made a great comment as we were debriefing in the elevator after the meeting that is the foundation of this post.  Tami and I shaped her comment into this metaphor: Finding wood to help start a fire is different from pouring gasoline on a fire As an entrepreneur, you need to constantly be asking for help and networking.  Those meetings will shape your business in ways that you can never predict.  They’ll shape…

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…

Agile Everywhere, Part II

Over the years, I’ve written a lot about the Agile methodology on this blog. For those of you who are regular readers, you may remember a post I wrote about our Agile Everywhere initiative— where all Return Path teams were tasked with implementing agile practices. A little over a year later, I want to update you on our agile journey–where we are now and how we got there.  My colleague Cathy Hawley (our head of People) will write a more detailed series of guest posts  for those of you who want to get more details of our transformation process. Before we started our Agile Everywhere initiative, only our product and engineering teams were using agile. The rest of the organization…

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 wild.  It’s one of the big things that I’ve found that VC investors as Board members, and independent directors, bring…

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 weird.  You don’t see that all that often in other industries, even when people take aim at market leaders. During…

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 you want to be about running your own agenda, things happen around you — with your people, your customers, your…

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 used to take at least one full two week vacation, completely unplugged, at least once a year. I miss that!…

Reboot – Back to Basics

As I mentioned in last week’s post, I’m rebooting my work self this year, and this quarter in particular.  One of the things I am doing is getting back to basics on a few fronts. Over the holiday break, as I was contemplating a reboot, I emailed a handful of people with whom I’ve worked closely over the years, but for the most part people with whom I no longer work day in day out, to ask them a few questions.  The questions were fairly backward looking: 1.       When I was at my best, what were my personal habits or routines that stand out in your mind? 2.       When I was at my best, what were my work behaviors or routines…

Ideas Matter Less Than Execution Which Matters Less Than Timing Which Matters Less Than Luck

Well, that’s a mouthful.  Let me break it down. Ideas Matter Less Than Execution Execution Matters Less Than Timing Timing Matters Less Than Luck There’s a persistent myth about entrepreneurs as heroes – the people with the brilliant ideas and Eureka moments that bring companies to life and create success.  I’ve never believed in that myth, or at least not in its universality, as I’ve always valued both ideation and execution in terms of business building.  But as I was thinking about that construct more the other day, it occurred to me that there’s actually a hierarchy of the two, and not just of the two, but of timing and luck as well.  The best businesses — the runaway successes…

You Have To Be All In, Until You’re Not

One of the things I’ve learned over the years is that as the organization scales, you have to be all-in, until you’re not.  What the heck does that mean? It means that, other than confiding your indecision to a very small number of trusted advisors on a given issue, indecision is poison to the people around you and to the organization in general.  So even if you’re thinking of doing something new or different or making a tough call on something, you generally need to project confidence until you’ve made the call. One example of this is around a decision to fire someone on the team, especially a senior executive.  Public indecision about this reminds me of years ago when…