A Fork Stuck in the Road

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 of Boston’s fastest growing startups, and integrating it into VMware has finally come to a close. It is without a doubt a bittersweet moment for me. On one hand I know it’s time for me to explore new opportunities, and maybe even form a new band (yup, leaning into this music analogy). But on the other hand, I know what a privilege it has been making music - a.k.a. driving customer value - with such incredible bandmates. I know opportunities like CloudHealth don’t come along often, and when they do, we often don't fully appreciate them until years later. But at this moment, I can see and appreciate CloudHealth in full.

I started CloudHealth in 2012 with the irrational decision to quit my job. I say “irrational”, but in truth this decision came only after agonizing months of evaluating the downside risks of starting a company. Quitting a well paying job with two young boys and a mortgage was not an easy call. But solving public cloud management felt less like a choice and more like a calling. And so I left my job to start the band. And it wasn't long before I found other musicians who wanted to play with me.

Like all bands, we had our ups and downs. We struggled the first year after signing with a record label (raising venture capital). We thought we had product market fit, only to find it was challenging to acquire new fans (customers) with consistency. We took our gigs where we could get them in those days, and no nightclub or wedding venue was too small for us - even at $250 MRR. But in 2014, we had our breakthrough album, and when the highly anticipated follow up album went gold in 2015, we were suddenly a hot band. You should have seen us play the showcase floor at re:Invent 2015 and 2016. It was definitely a Queen at Wembley moment. But whether we played small nightclubs or big stadiums, one thing always stayed the same: we had the best and most committed fans in the industry.

While we lacked the typical behind-the-music drama of drug use and divorces, we had our own challenges. We fought for every customer, struggled with hyperscale, and made our fair share of mistakes. We lost bandmates over the years too. Our lead singer went on to become an investor and board member; our drummer retired to his Cape house and boat; and our new lead singer left two years after we went double platinum and sold out (in this case, literally). But even as people came and went, a simple formula made it all work: great musicians, who loved making great music, with great people. Call me old school, but life is too short to do it any other way.

As I embark on my solo career, I don’t really know where it will take me. It’s been 8+ years since I’ve been out on my own, and so much has changed in the industry. But I know successful solo artists need to be more Sting and less Billy Corgan - i.e. they need to look forward and not back. In the end, it’s all about the music. I’m also intrigued by the music coming from some of the younger artists these days, and hope to have time to explore that scene. So over the coming months you can expect to find me listening, learning, advising, supporting, and planning. And I will be doing it in the best place to make music in the world: Boston.

I know the band will go on. I won't be surprised if they make better music without me... just hopefully not the Sammy Hagar kind of “better music.” I also know some people will think I am leaving the band over creative differences, which is simply not true. I never insisted my wife be in the studio during recording sessions, or argued over songwriting credits, or stormed offstage after a tantrum (my CMO might say here: at least not on camera). That said, I do think we could have used a little more cowbell.

I wish all the best to my bandmates, both current and former. I couldn’t have asked for better people to make music with. You may see me in your audience from time to time, and you know I am only a phone call away if you need me. Just try to say nice things about me in the Netflix behind-the-music documentary. 😉

So goodbye CloudHealth. I am going to miss you. Keep making great music. And rock on.

Joe Kinsella, CTO & Founder, CloudHealth