
Survivors
Failure. It smells. People are afraid of it. It’s like cancer. When you have it you find you who your true friends are because they’re the ones who double down on helping, on being available, on listening, on understanding. Most people run from failure or disease because they’re hard to handle. Hard to know how […]

When things go wrong
In technology, as in so much else, things go wrong all the time. Web sites go down, companies lose your data, and more. We all know this and – to greater or lesser degrees – broadly accept that it will eventually happen to us. The real trick, often, isn’t to prevent everything going wrong but to […]

So You’re Shutting Down Your Startup And You’re Scared…
I ran across Startups Anonymous, and a post entitled, “We’re Shutting Down and I’m Scared” caught my eye. For better or worse, I’ve either been through or participated in shutting many companies down, so I thought it would be fun and potentially useful to provide my blow-by-blow advice: *** After over two years, backing from […]

Celebrating Failures
Being a passionate design thinker I am a big believer in failing fast and failing often. I have taken this one step further; I celebrate one failure every week. Here’s why: You get more comfortable looking for failures, analyzing them, and learn from it I have sat through numerous post-mortem workshops and concluded that the […]

Why most startups have to fail, and why that’s a good thing
Some people think I’m a pessimist for pointing out the long odds against any particular startup succeeding. It’s not fun to hear that even venture-backed startups have a 90% chance of failure. But startup failure isn’t just reality; it’s also a necessity…and even a benefit. 1) The number of companies getting started far exceeds the […]

Why I hate acquihires (unless I’m doing the selling)
The always insightful Mark Suster recently tackled the subject of acquihires–the practice of large companies buying small startups simply to acquire their people. Mark lays out an excellent argument for why the acquiring companies are actually losing out when they make acquihires: “You have been at Google, Salesforce.com, Yahoo! for years. You have worked faithfully. […]

Who is to blame when a SAP Payroll Project Fails
There have been several high profile SAP Payroll failures over the past few years in the United States at places such as the State of California, National Grid, Kentucky Government, City of Portland, LA School District, City of San Diego, California Judicial Council, Marin County and an epic train wreck happening down under at Queensland […]

A debate with the Doctor of Failure
Failure happens. There are many issues and stakeholders in any technology implementation process and any of them adds complexity that can lead to failure. The question is how much technology, the DNA of the technology vendor, and other stakeholders contributes to the failure. Is it always a project management issue…

Failure Fridays
Someone very close to me is about to begin a very cool new gig. Its a role that most would love and in fact be envious of (I sure am – and will be blogging about it soon!). So this…

And They Call Me Crazy
Nine years ago today I was driving into the city of Boston to pick up my wife. Normally she’d take the ferry from Boston back to Hingham, but today was different. I quickly noticed while driving northbound on Hwy 93 that all of the cars were headed South. There wasn’t a single car driving North […]

There Is No Upside In Being A Jerk
The world is full of jerks. But it must be some kind of innate instinct, because there is no upside to being a jerk. One of the first questions I ever responded to on Quora asked if being nice was an advantage for VCs. The consensus was that success trumps affability, and that entrepreneurs would […]

Little Bets and the Power Of Quitting
As an entrepreneur or a company, you should appreciate the underrated power of quitting. While we often glorify a never-say-die attitude, and celebrate the entrepreneurs who build great companies despite near-universal criticism, extreme persistence comes at a price. I caught up with a friend yesterday, a high-profile entrepreneur who will remain nameless (I forgot to […]

What is the Right Amount of Money to Raise at a Startup?
This is part of my ongoing series on Raising Venture Capital. Recently I’ve been debating with a number of young startup companies that are raising money in the next few months, “what is the right about of capital to raise at a startup?” It’s a tricky question with no clear answer. There are trade offs. […]

Social Media is the New Collaboration
When we look at corporate frameworks and how we use collaboration and innovation across corporate boundaries, including collaborating with other companies to get a product out to market we are looking at social networking. We just have a fancy new label for it, but in the longer run, what we saw as collaborative teaming and […]

You’re Most Vulnerable Right After You Win a Deal
This is part of my ongoing series, “Start-up Lessons.” Recently I wrote a blog post about how I hated losing, but I embrace it. My starting line with every entrepreneur is that everything I learned about being an entrepreneur I learned from F’ing it up on my first business. I even put that in the […]