Posts for "Entrepreneur"

The inauguration has me in a patriotic mood. Instead of writing my planned post on leadership, I’d like to tell a story from American history. For those of you who don’t know me, in addition to being an entrepreneur and a technologist, I am also a bit of

I learn more from my failures than I do from successes, and so as a result, I have done a lot of learning in my career. My list of failures is long and growing. Among my more notable ones include not being able to get a software job out of

I had a great idea for a feature in the early days of CloudHealth: enabling customers to collaborate around their cloud resources. For example, a manager might want to let their DevOps engineer know they forgot to “turn the lights out” on some infrastructure; a developer might want to let

One of my early Minimum Viable Products (MVPs) in the founding of CloudHealth Technologies was to test the value proposition of cloud cost optimization. I needed to validate two critical assumptions to my product idea: (1) I could drive a meaningful reduction in cloud costs for customers, and (2) there

The Lean Startup movement popularized the concept of Build-Measure-Learn (BML) as a means to reduce the risk of the creation of new products and businesses. The concept is simple: build a Minimum Viable Product (MVP), measure the product’s effectiveness in the market, derive critical validated learning, and then start

October is the two year anniversary of the acquisition of my company, CloudHealth Technologies, by VMware. CloudHealth as a private company was definitely a labor of love for me, starting with the irrational decision to leave my job with two young kids in 2012, and ending with me in front

As the CTO and founder of CloudHealth Technologies (acquired by VMware in 2018), I am intimately familiar with the razors edge existence on which startups live. A startup typically derives its revenue from a single product or service, spends more cash than it takes in, and lives on the law

When CloudHealth was still a private company, I would regularly get congratulations from people over the performance of our business. If we were raising money, it would be common for a potential investor to say: “Congratulations on a really impressive business.” Or if I were at a networking event, I

In spite of the fact the Red Sox are playing like they're in spring training, I'm glad to have baseball back in my life. My interest in baseball and technology have been intertwined since I wrote my first serious software at age 11: a simulator to predict how Babe Ruth

I re-listened to Reid Hoffman’s Masters of Scale episode 4 (Imperfect Is Perfect) on the walk from the office to North Station last night. This episode highlights the criticality of putting your product in front of customers early and often. The topic is an obvious one for Reid, who

I was on Cape Cod with my family when my CEO called to tell me the time had come to make a decision. In the anatomy of a deal, there are many points at which you can safely safely hit the eject button, but this perhaps was the most important

A year ago I made my Last Post to my blog. Over the previous eight years I had made 325 posts on topics that ranged from the cloud to product management to software development. But last March I decided to make it official: I was tapped out. I’m sure

Last year on a long drive from New York, my wife and I found the Tech in Boston podcast. If you are in Boston technology and haven't listened to Dave Gerhardt's podcast, you are missing out on one of the best channels for startup shop talk in the area. At

I had a couple meetings with entrepreneurs this week, which I occasionally do as a pay-it-forward approach to the support I’ve received over the years. In both cases the hot topic on the entrepreneurs' minds was raising early stage venture capital. I always start by telling my story from

Last summer I did a blog post titled My Startup Anniversary: 3 Years In Blog Posts. The goal of the post was to provide a journey through my personal blog as written while starting and growing CloudHealth Technologies. I thought I'd update this post for my 4th year. And So

In April this year CloudHealth hosted a NewCo Boston presentation called Agility Experienced. Success Realized. Our VP of marketing had signed me up for the session, which I prompting forgot about until I had to scramble to figure out what to present the day before. Below are the slides, which

I sometimes hear the name of a new company and can’t help but appreciate its simplicity and power. For example: Cloudera, Docker, Pinterest, Uber. I like to think that these names came from an HBO Silicon Valley-esque vision quest by its founder, mushrooms optional of course. But in truth

While in truth there is no singular moment in which you start a company, I still mark the official start of CloudHealth to a Lean experiment that took place three years ago. It’s a story that reveals the power of experimentation, the value of taking managed risks, and the

I'm a big fan of listening to startup founders tell the stories of how their companies came to be. These narratives often read like tightly written short stories, with a protagonist, a conflict, unexpected plot twists, and always some kind of resolution. Founding stories can give you insight into the

One of my favorite chapters of Peter Thiel’s Zero To One is called “Secrets”. It reads like a late night revelation, that wanders from the Unabomber to HP’s business failure in the 2000s to Fermat’s Last Theorem. Thiel outlines the premise that secrets about nature and/or

An Irish entrepreneur I know asked me yesterday how I’ve dealt with the ups and downs of starting a company. For all the books, articles and blogs on entrepreneurship, there is surprisingly little discussion on the emotional side of being an entrepreneur. Until I read Brad Feld’s post

This morning I took a journey back through my blog, reflecting on my three year journey in founding CloudHealth Technologies. It's hard to believe how quickly the time has passed from working out of the entrepreneur space at NBVP to having a fast growing company in downtown Boston. Here is

Just like we have founders of a business, we also have founding customers. These are customers who took a chance on you at the earliest stages when there was very little to take a chance on. While they may have paid for your product in those early days, they more

As entrepreneurs of early stage businesses, we all aspire to help our companies navigate the turbulent waters from idea to product market fit. But once you've achieved product market fit, a new and sometimes harder challenge often arises: scaling the business. During the scaling phase, an upside to being an

There are many ingredients that go into building a company: hard work, emotional fortitude, agility, willingness to take risks, fanatical commitment to driving customer value, ability to execute in the face of ambiguity, and more. But there is one ingredient that often gets overlooked: an ability to will something to