I came into the software world at the crossroads of the change from waterfall to agile. Most of my older colleagues had spent their careers in waterfall: writing detailed requirements, building comprehensive designs, writing code that adhered closely to the designs and requirements, and then going through long testing and…

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 the…

All early stage entrepreneurs get asked this question at some point in their venture: do you have product market fit? It’s a simple question that investors and advisors use to assess the risk in a business. But unfortunately, it’s also a question too many entrepreneurs feel the reflexive need to…

I’ve binge watched enough Netflix behind-the-music documentaries to know that if CloudHealth were a rock band, today would be the scene where I announce I’m leaving the band. Yes, today is my last day at CloudHealth by VMware. My 8+ year journey of founding a company, building it into one…

My first Dotcom Boom startup was a spin out of the MIT Media Labs called FireFly. I was a full convert to the internet by then, believing I was engaged in a movement that would change the world. In those heady days we worked in “internet time”, competed for “eyeballs”…

After social distancing on Cape Cod for 13+ months, I returned to Boston to find a very different tech community than the one I left. Gone were the coffee meetings, the meetups, the collaborating at a white board, the conferences, and the after work drinks. Replacing them was Zoom, Zoom…

In the early formative phases of CloudHealth, I ran an experiment called “The Sale.” The idea of the experiment was to try to sell my crude Minimum Viable Product (MVP) for $50K, which was my estimated average selling price for the proposed business model. The idea of the experiment was…

A little over a year ago I drove through Boston on my way to Cape Cod. The pandemic had started to spread across the country, and the previous day my company closed our downtown offices for mandated work from home. The early morning light on the empty rush hour streets…

I once tried recruiting an employee from a large tech company who had a great background but one noticeable flaw: he’d only worked in big companies. While this is usually a red flag for me, I thought it was worth a Hangout to see if he might have crossover potential…