With the "build in public" trend in fashion these days, I decided to comb through my old blog posts to bring together the nine year story of CloudHealth Technologies. It is particularly timely since the company that acquired my startup, VMware, has now also been acquired. As for my interest in "build in public," I was just never one of those people who believed in stealth mode startups. If telling someone what you are going to do makes it likely they will do it better than you, maybe you shouldn't be doing it in the first place.

CloudHealth Technologies was a pioneer in the cloud cost optimization market. It started as a one-person business in 2012, driven by my professional passion around all things public cloud. We raised our first round of venture capital in early 2013, and slogged our way to product market fit in 2014. After this we started to grow - to borrow a famous Hemingway quote - two ways, slowly and then suddenly. After turning down acquisition offers in 2015 and 2016, we decided in 2017 that we were "going long" (venture speak for IPO). We raised one more large round of venture capital, did a CEO transition, brought in several new executives, and then were approached in the spring of 2018 by VMware for a "strategic partnership." Things moved quickly from there: term sheet, due diligence, public announcement at VMworld, and the acquisition close in October 2018. So much for that IPO.

I stayed at VMware for 2 1/2 years after the acquisition, leaving in 2021. While I have long ago lost touch with my former business, I have kept in regular touch with its most important assets: the people. In fact, this September we had a company reunion at an Irish pub in downtown Boston to celebrate the incredible journey we had together.

So here is my "build in public" startup journey, as told through my public blog posts.

And So It Begins (2012)

I had originally thought of starting CloudHealth in 2010 after deciding to leave Dell. I suppose it was obvious to explore creating a business at the intersection of my two professional passions: cloud computing and infrastructure management. But after receiving a lot of push back on the idea, I decided to take a detour in 2010 to be a VP of engineering at a cloud startup called Sonian. This was a fortuitous digression though, since it let me work with one of my favorite founders, Greg Arnette, and became the proof point for the product idea. So by 2012 I had returned back to the idea of starting a company.

February

March

May

  • Disruption in the Cloud - I had realized in 2010 the public cloud was a tsunami that was going to sweep over all industries in the coming years, fundamentally changing the landscape of tech for decades. This was me trying to verbalize this thought using the Innovator's Dilemma.
  • Defining a Cloud Reference Architecture - While this post talks about a cloud reference architectures, it was in many ways my first attempt to start talking about the product vision for what would become CloudHealth.

June

  • 5 Signs It May Be Time To Move On - I had realized it was time to resign and was working up the courage to make it happen. I think I resigned shortly after this post.
August
  • Movement in the Cloud - I decided to make my resignation from Sonian official with this post. With a mortgage and two kids in elementary school, even then this felt like a highly irrational decision.
  • Amazon Reserved Instance Calculator - I guess you can call this my first Minimum Viable Product (MVP). Good idea, not so good execution. I wrote this while on vacation with my extended family on Cape Cod, where I tried hard to avoid having to explain to them why I quit my job.
September
  • 9 Tips To Improving Your Lean Startup Validation - The Lean experimentation began, and with it a post on what I learned. While I fully bought into the Lean concepts, I couldn't help but feel Lean Startup was just the marketing version of the real book that opened my eyes: The Four Steps to the Epiphany.
  • A Cloud Is a Terrible Thing To Waste - I was always intrigued by the stories of cloud dropouts, since I believed they were canaries in the cloud coal mine. I was certain these failures were proof my emerging product vision.
October
  • 10 Steps To a Read Only AWS User - I needed least-privilege credentials for a concierge service I ran to prove out the idea of cost management, and decided to document this for other AWS users. This of course pre-dates AWS making this easy.
November
  • The $18 Billion Disruption - My first public rumination on the target market for my business.
  • Burning Your Boats and Bridges - I wrote this post over lunch at a sushi restaurant in Somerville while taking a break from a contract software gig. I knew the next phase required a new level of commitment that wouldn't give me time for a side hustle. This was me saying publicly that I was all-in.
December
  • 6 Steps To Running a Lean B2B Experiment - By this time I had closed my first two paying customers and brought in my former colleague Dan Phillips, as CEO. It was now a two-person business and we were busy pulling together an investor pitch deck.

Early Company (2013)

We convinced our former CFO from SilverBack, Dave Eicher, to come join us in February. In March we closed on a series A round of capital, sublet some office space at 280 Summer Street, hired the first team members, and launched our first product. We were simultaneously learning how to build, market, sell and support our early customers. What I didn't know when the year started was that we didn't have product market fit yet - so this ended up being a rollercoaster year on the product side. This year went by in a blur.

January
  • A Cloud Management Taxonomy - The start of fund raising found me spending an increasing amount of time thinking about how to position my company in the market. I used to call this the "15 minute elevator pitch," since it took that long time for investors to make sense of what we did - with many never really figured it out. That is one of the downsides of creating a new product category.
February
  • My VC Thought Experiment - We signed the term sheet for our series A around this time. This post was me lamenting on the challenges of getting investors to see an entrepreneurial vision. While we closed the round, it was not easy, and we were turned down by many investors.
  • Goldilocks and the Three Startups - It always amazed me the wildly conflicting opinions we received from investors. This was a bit of rant by me on the small bullseye you sometimes have to hit in order to raise venture capital.
  • Cloud Fratricide - This is me thinking about the single greatest point of failure in managing large scale cloud infrastructure: people. It is also the first public example of me starting to talk about the rapidly growing complexity of the cloud.
March
  • Recommended Reading For Entrepreneurs - I'd read dozens of books on startups / entrepreneurship prior to and during starting the company. This post included some of my favorites, most of which I had read the previous year.
  • My Lean Startup Journey - With the term sheet signed, we were waiting on closing the round of capital. I decided to pass on some tips from the early phase of my journey.
  • Product Management Is a Company, Not a Department - My early thoughts on how I wanted to run product management in my new company. We are always optimizing for what didn't go right in our last venture.
June
July
September
November
  • 5 Tips to Hiring in Boston - When will the recruiting end? Getting a great early tech team at place was an all-consuming mission. But when you are lucky enough to get engineers like Vikram Pillai, Andi Abes, Steve Frank, Efe Yardimci, Dick Wallace, Adap Schepis, and Jeff Zhou on the same team, it's hard not to build a successful product.
  • Day 1 at re:Invent: Sold Out - AWS re:Invent even in these early days was the conference to be at for anyone who cared about the public cloud. We were too cheap to get a booth at re:Invent, but had great customer meetings in our hotel suites. We bought too few passes, so I am embarrassed to say we had to share passes to get on the show floor.
  • My Jeff Barr Interview - Our VP of marketing, Melodye Mueller, scored a hit by getting me a video interview with Amazon's chief evangelist, Jeff Barr (the assist goes to Greg Arnette who gave us the tip).
  • Day 3 at re:Invent: Disruption Achieved - Thoughts as I headed home after re:Invent.
  • Cloud Escape Velocity: PaaS on IaaS - More thinking about the power of AWS's latest service announcements and how it a would shape the future of the cloud.
  • On Startup Execution & Adversity - My mother passed away in January 2013, just as we were about to go for our first venture pitch. It hit me hard and almost made me abandon the business. This post was my personal reflections months after the experience.
December
  • Cloud Evolution: Cloud 2.0 - More thinking on the future of the cloud.
  • 2014 Predictions for the Cloud - Every VP of marketing is obliged to make their CTO & founder make predictions in December.
  • The String of Pearls - Sharing my thoughts as we converged toward product market fit. If you work with me, this is one of those analogies you will hear me use regularly, because it is foundational to how I think about early stage products and companies.
  • Google Glass: Day 1 - This had absolutely nothing to do with my company, but was a digression on my lifelong pursuit of becoming a human cyborg. I used to tell people that I would be attending re:Invent 2020 with my mind clone and a body made up of 10% machine parts. 😉

Product Market Fit (2014)

This was a break out year for our company. We achieved product market fit, had the first substantial growth in our business, and signed a term sheet for our series B round of capital with Scale Venture Partners (which closed in 2015). It took incredibly hard and dedicated work by our team to get to the point where we had a real chance at success - but even then, our future was not certain.

January
February
  • Agile Product Management - I spent a lot of free time thinking about one of the weakest links in previous product teams: the product management process. So many companies freely admit they do not have good product management while simultaneously knowing that good product management is essential to company success.
March
  • Reflections: 1 Year Post Funding - My lessons learned a year into my series A funded company.
  • The Return of On-Shoring - When the company was just me, I had a small offshore team I used to supplement me writing software. As soon as I had the capital to hire local engineers, I immediately moved to a local team model. Having worked with on-shore and offshore teams in my past, there is nothing like a local team.
April
June
July
  • What To Do In Response To Code Spaces - This was a wake up call for all of us in the cloud. In addition to making me rethink our internal cloud security, it was also the first time I started thinking about security as part of the longer term vision.
  • The Agility Volume Knob - The business side of the company wanted the impossible: rapid agility with absolute predictability. I wrote this post as part of my thinking on how I wanted us to balance agility and predictability.
  • AWS Revenue Slip? - This was the days before AWS published their revenue. These are my observations on the cyclical nature of AWS revenue.
August
September
  • Conviction - When I started the business, it was based on a contrarian point of view around freemium software, which was the trend of the day. This was me reflecting on how sometimes it's important not to follow the herd.
  • Hacking at CloudHealth - Our first hackathon, which became an institution in the company.
  • Competitive Analysis - I used to tell everyone in the early days that everything I needed to know about my competition I could learn from my customers and prospective customers. I still believe this today. Too many people over-focus on the competition.
  • Entrepreneurship: The Chicken and the Pig - Steeling myself for raising a round of capital in spite of all the talk about a "Boston B round crunch." Hint: I'm the pig in this post.
  • Finding the Minimum Viable Feature (MVF) - In addition to still actively writing code, I was also the one-man product management department. The concept of MVP was deep in our DNA by this point, and this was me talking about how we had extended this to every feature.
November
December
  • The Heterogeneous Cloud - re:Invent always spawns one or two thoughts on the future of the cloud market. While I still believe in this vision, it has yet to come true.

Early Growth (2015)

Our $12M series B round of capital closed at the beginning of this year, led by the west coast Scale Venture Partners. We were fully in the growth stage at this point, with the MRR for every month increasing substantially over the previous one. We also were moving from an unknown startup to one increasingly recognized within the cloud industry. I also hired a VP of engineering this year, as part of our continued focus on scaling.

January
March
May
June
  • Software: The Process Is the Constraint - We were actively hiring for a VP of engineering at this point to help grow and scale the team. Simulatenously we were confronting the challenges of growth in every part of our business. I'm not a fan of prescriptive software process. To me, it's about the people.
July
August
September
  • The Psychology of Being an Entrepreneur - One of the underserved topics in startup community is the psychology of being an entrepreneur. Starting a business is one of the most irrational acts a person can perform. It can be at times a grind. These were some of my lessons.
  • Software Development: Adjusting Execution To Need - As we scaled, we started to lose our risk-taking startup edge. I introduced a framework to allow us to adjust the execution of projects to the business need. The concept is that all projects should not be taking the same approach to risk.
October
  • Clear Skies at re:Invent 2015 - It's time for AWS re:Invent, our biggest conference of the year. We brought a big team this year, and had a great success.
November
  • Beginning of the End of Shadow IT - We continue to see rapid enterprise adoption, and with it an increasing growth in IT departments looking to govern the cloud without adversely impacting line of business agility. This was the beginning of the early majority phase of the Technology Adoption Life Cycle in the cloud.
  • On Clouds & Containers at Structure 2015 - I took a breather from the grind to pick my head up and go to Structure Conf.
  • 5 Things Google Can Do To Get Back In the Cloud - People didn't think I liked the Google cloud very much. This post attempted to capture what I thought they needed to do in order to get back in the game.
December
  • Founding Secrets - The chapter titled Secrets of Peter Thiel's Zero To One was for me like the moment in The Matrix when Neo saw the fabric of the virtual world. My "secrets" were pivotal to starting my company. It's too bad Peter became such a political lightning rod, because this was actually a good book.
  • Founding Stories - I am a student of founding stories. I believe they carry essential lessons that can help steer future success.
  • Starting a Company the Lean Way - Took a moment to reflect on the 2012 moment of creation of my company: when a Lean experiment designed to fail accidentally succeeded. This is a story I frequently told in interviews but had never put into my blog.

More Growth (2016)

With revenue growing quickly and business processes continuing to get more efficient, we continued to scale.  We closed a $20M series C round of capital in May to support the expansion, led by Sapphire Ventures. This unfortunately created some inequities in the board that would be with us for our life as a private company.

January
  • Passions, Interests & Jobs - Great accomplishments require great effort. I understand that working in a startup is just a job for some people. I am happy these people like working in startups. I just don't want them working in my startup. 😉
February
  • Collaborate: Do Twice the Work In Half the Time - Collaboration was the key to our early company DNA. As we grew, I continued to try ways to ensure we maintained this. This was especially importance since I had handed engineering off to our new VP of engineering, who himself was still ramping.
March
  • 5 Rules To Maximizing Team Transparency - Transparency is one of the core tenants of our company culture. This is another example of me talking about one of the things I was struggling to scale. So much of my thinking in these days was around organizational scale.
June
  • Picking a Company Name - This was a walk down memory lane recounting the story of how we came up with the name CloudHealth Technologies. Dan always hated my original company name. Few people realize we closed our A-round of financing with a different name.
July
  • NewCo Boston: A Startup Journey - We hosted a session at our offices for NewCo Boston, which was mobile conference where people walked between offices for talks. I presented my entrepreneurial journey, including all the mistakes and best practices I learned along the way.
  • On Venture Rejection - We raised the first round of venture capital for our business back in 2013 in record time. I decided to finally the real story, which was a lot less pretty than it looked externally.
  • Startup People - This was unintentionally one of my more controversial posts: a rant on what makes startup people special and why they are different from everyone else. Apparently some people working in big companies didn't like how I characterized them.

August

  • My Tech In Boston Podcast - Dave Gerhardt was running a great podcast in 2016 called Tech In Boston. We were investing more at this time in local media in order to increase the visibility of the company for hiring purposes. I don't generally like to be interviewed, but I thought he did a good job with this episode.

October

  • Cloud Computing Weekly Digest with Joe Kinsella: October 22 - This is one of the few examples of the weekly post we would make on our website that made a guest appearance on my personal blog. Our goal was to increase our company profile in the industry. The format for the post was industry news with a heavy dose of satire. We had a lot of fun writing these posts.

Going Long? (2017)

While the growth continued in 2017, so did a lot of challenges in scaling the organization. We started to see more organization debt, caused in part by the standard challenges of rapid growth - but also due to some mistakes on our part. During this year we would raise a big round of capital from Kleiner Perkins, bring in our new CEO, Tom Axbey, say goodbye to Dan Phillips, and start the next phase of the company. This was the beginning of us "going long." You'll see how that worked out shortly.

January

  • Content Over Process - As we were scaling engineering, I was finding engineers increasingly disconnected from the business. It reminded me of one of the great interviews with Steve Jobs and his comments about process and content. If you have never watched the Lost Interview, you are missing out on one of the best Jobs interviews.

February

  • Book Review: Zone To Win - I was struggling with finding how to maintain innovation in an organization that was getting increasingly larger and slower. One of my customers recommended Geoffrey Moore's book.

April

  • Have You Ever Sold a Story Point? - With hindsight, this post was just bad behavior on my part. To scale engineering, we started tightening our process, and it suddenly seemed to me that there was more passion around the process than our products. This was just a rant.

October

  • Opportunities In Adversity - This is probably the most important step we took in our 2014 journey to product market fit. While this was truly a team effort, I was lucky to have a great partner in our VP of sales, Eric Shoemaker, in getting to this point. But I think I decided to tell this story at in 2017 since we had just done a CEO transition as as part of "going long."

December

  • Default To Neutral - I know the topic of working hard has become controversial today, with many people thinking this is a sign of a defective personality. But here is my unapologetic take on the topic. It is also a reflection of my continued concerns that as we grew, we were losing the one advantage all startups have over big companies: the ability to move fast.

Acquisition (2018)

This was a year of change for the company. We brought in new executives, saw the departure of some early members of our team, and started retooling almost every part of our business.  Then in April of 2018, Tom asked me to present to a team flying in from VMware looking for a strategic partnership. I was admittedly skeptical of spending time on a VMware partnership, since we had first started talking with them over two years earlier. After presenting for eight straight hours to a team that included an SVP and multiple CTOs / VPs, we then spent 3+ hours at dinner. This would be the beginning of an M&A process that would result in the acquisition of my company in October. So much for "going long."

March

  • My Last Post - It is ironic that I chose this point in my blogging to stop the story of CloudHealth. I had become bored writing on primarily tech topics over the years, and wanted an outlet for all the other things in my life - e.g. boating, hiking, fishing, Cape Cod. I would later realize I could just blend my non-tech hobbies right in with my other posts.

November

  • Context Is King - I wrote this post after acquisition as I was trying to figure how to re-organize the engineering team. I don't remember the story of how this post slipped in after my "last post."

Post-Acquisition (2019)

At this point I was working in a big company, flying regularly to Palo Alto, and starting to confront the challenges that come with being acquired. I will confess to being somewhat relieved to have sold CloudHealth to VMware. When we were private, I felt personally responsible for every employee and everything that didn't go right in the business, even when I was not directly involved. It was mentally exhausting.

March

  • I'm Back - This was me returning to blogging after my break.
  • The Decision To Sell - I decided to explain how I went from "going long" to selling the company is less than 18 months. I'm sure this was cold comfort to my investors who wanted an IPO.
  • Iterating In the Presence of Customers - Reflecting on my strongly held belief that the only way to build great products is to interate them in the presence of customers. Unfortunately we weren't doing a lot of this though post-acquisition.

April

  • On Baseball & Startups - I have been a big baseball fan for my entire life. April is the start of the MLB season. Of course I would have a baseball-themed post.
  • The 2.0 Cloud - I had been using the "digital camera" analogy around cloud computing in my public speaking for several years, but had never put it into a post. I'm not entirely sure what prompted me to do this then.
  • My 1st Lesson In Incremental Delivery - The relief of no longer being responsible for my company put me in a reflective mood. This is a story from back in my wild Dotcom Boom days.

May

  • My Hot Red Sports Car - At our investor dinner to celebrate the acquisition, everyone talked about how they knew CloudHealth was going to be a success from the start. I was the only person who spent my entire time at the company feeling we were one bad decision away from failure.

Working In a Big Company (2020)

I returned from visiting Red Sox Spring Training in Fort Myers with youngest son to find the world shutting down due to Covid-19. I immediately decided that if I had to work from home, I would do it on Cape Cod. Like many of us, I did a lot of reflection over this year personally and professionally, so my posts varied widely in topics.

April

  • Resignation: Doing It the Right Way - If you have worked with me before, you will have heard me say: "No one ever remembers how you arrived at a company, but everyone will remember how you left." I am a big believer in leaving companies the right way. Reputations matter.

October

November

  • The Importance of the M in the MVP - This is an overview of one of the key Lean experiments I did in 2012.
  • A Product Manager's Lessons From a Failed Feature - More thinking on my belief that the best way to build successful products is through continuous experimentation.
  • The Art of Failure - I think this post was sparked by a conversation I had with a friend who had just shutdown his company. I have an odd relationship with failure. I simultaneously fear it while acknowledging it has also propelled my greatest growth.

December

Leaving (2021)

When I resigned in November 2020, I agreed to give six months notice. While I didn't plan it, the timing aligned perfectly with my contractual commitments to VMware. It was tough though to know I had resigned but not make it public. I spent these last few months hiring my replacement and getting ready to move on. This was my least enjoyable time at CloudHealth.

January

  • On Leadership - I love this statue of George Washington in the Boston Public Garden. I also love history. These two came together in this post.

February

March

April

If you are interested in learning more about my journey, check out one of my favorite interviews on the Authentically Successful podcast.