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 a contributing factor was the six years of grinding it out building a startup, which had taken from me nearly every ounce of energy. The process of stopping the blog had started by just slowing down, with weekly posts becoming monthly, and monthly becoming every few months. Eventually though I had to just admit it: I had nothing more to say.
A lot changed in my life during the year since that last post. My oldest son went off to college at Northeastern University. In June of 2018, my company started acquisition conversations with VMware, a public company that is a leader in cloud infrastructure and digital workplace technology. By August, VMware announced their intent to acquire CloudHealth, and by October the deal was closed. As part of the acquisition, I moved back into an operating role, leading an organization with a focus on driving transformation. A lot of experiences were packed into that short year, from the pride and sadness of sending a child off the college to investor conflicts to the emotions of selling a company.
But during that time, something else happened: I realized I wasn’t all tapped out on tech blogging. While my passion for startups, entrepreneurship, Boston, and the technology industry never waivered, I suddenly found myself with something to say again. I started to reflect on my experiences and had questions. For example, could we have invested more in organizational scaling earlier in our business? How do you adapt your hiring for the different phases of growth? Why is it investors insist on changing management teams to support the different phases of a growth startup, but never assume board members should change too? I could go on, but you probably get the idea.
I guess this post in a long winded way of saying: I’m back. I’m not sure what I will say, or how frequently I will be posting - but I do have something to say again. So let’s get this started.