My Chocolateyfest (WinOps) Conference Experience

Several months ago I was text messaging with Rob Reynolds, found of Chocolatey. Rob and I have become friends over the past several years due to my involvement in using and writing about Chocolatey software. Rob mentioned the idea of a conference focused around Chocolatey. I immediately response “wow that would be awesome”. This idea came to fruition a few months later when Chocolateyfest was announced.

Initially, Chocolateyfest was supposed to be a conference dedicated to automating Windows with Chocolatey, later it was changed to WinOps, broadening a bit the topics that could be discussed so that it would be automating Windows with anything. WinOps is a newer conference that was held in London in 2017 and will be held there again in November.

The inaugural Chocolateyfest (WinOps) being held in San Francisco seems to be an appropriate location being that is an innovative technology today. It is part of a movement in automating Windows that has been growing for years.

My trip – Day 1

Back in July, I proposed a talk at Chocolateyfest focused around how we implemented Chocolatey on our Windows end user machines. At the time I was super excited to go and present this to our community, although as time got closer to the conference I was close to backing out. My wife is due with our second child next month and work has been a bit crazy lately. Fortunately, for me, my wife urged me to go so I decided to make it out.

I flew out early on Sunday morning, a day before the conference began. My plan was to stay on east coast time so that going back after a two-day stay would be easier. As I write this, its 4 a.m. local time (San Francisco time) so I can say that my plan help up well. After arriving in SF, I was taxied to my hotel at the Park Central. My reaction to seeing the area was the same as when I travel anywhere beautiful “damn it I want to move here”.

My friend and peer Michael Lombardi was already in SF so I met him for a drink at the hotel bar after I arrived. One of the great things about going to tech conferences, especially ones that are small like this, is that you meet people. Even if you do not want to, trust me you will. Although I had initially met Michael prior to PowerShell Summit this year, we keep in touch regularly and I now consider him a friend for sure.

After a drink, we headed out to a speakers dinner that Rob was kind enough to organize to the Thirsty Bear, a brewpub close to the hotel. There I met several speakers and great people. A few people:

Gilbert – senior engineer from Facebook

Mark – Solutions architect

Michel – DevOps coach

Stefan – software engineer at Seal

I was also able to meet some new Chocolatey folks, all of whom were fantastic human beings. After a great dinner and a few beers, I headed back to my room to crash.

My trip – Day 2

Day 2 started early as hell. I was up at 3:30 a.m. and headed to the hotel gym for god knows why. I like to try to exercise a bit when I am traveling, but there is something just wrong about being there at 4 a.m. After some last minute changes to my presentation, a quick FaceTime conversation with my wife and daughter, I headed downstairs to start the conference.

I will not go into detail about the talks I attended, mostly because they were ALL amazing and it would take forever to write. We heard about Docker, Chef, PowerShell, Chocolatey, Puppet, Otter, Ansible, Boxstarter among many other technologies. We heard from organizations like Facebook, Yelp, Chef and Microsoft. I can honestly say there was not one talk that I did not want to attend. These engineers are doing the latest in greatest in best practice in our community. There was not one talk I left without learning something new or having something I wanted to implement.

My talk

One of the downsides to the conference for me personally, was that because I had a talk myself to do, I was a bit nervous about that. This is only my second public talk, and when you start looking at the other speakers around like Steven Murawski, you start to wonder if you really belong here.

My talk was titled “How I completely automated Managing Windows Desktop Software…Forever: A Chocolatey Story“. Yes, I know that is a long a** title and yes it was created with the idea to gain interest. I am a shameless promoter of myself. My talk was a bit of a deviation from the other DevOps-y talks. I do not work in a DevOps environment, so is not a topic I felt comfortable talking about. My talk was on using simple tools to automate a lot of crap, really geared towards people who are just starting with Chocolatey and wanted to see how someone else went about implementing it.

Overall, my talk went very well, at least that is what I feel. I did notice a typo on one slide IN THE MIDDLE OF MY TALK but whatever, it happens I suppose. The attendees were great and respectful, which is nice because it is a little bit unnerving presenting in front of peers. I am SO glad I did it though because it was an awesome experience and I plan to come here next year as well.

My takeaways

Back in April, I attended the PowerShell Summit for the first time. Outside of WinOps, Summit is the only tech conference focused on Windows automation. The main difference obviously, is that it’s focused on PowerShell. I LOVE PowerShell but it is necessary to have a conference that opens up the topics a bit outside of PowerShell completely, and Chocolateyfest (WinOps) is it. For us in the community, this is a conference we need to promote, attend and keep alive. I will urge people this year to attend because not only is the content and quality of the talks fantastic, it’s a great networking event. Attending the conference felt similar to PowerShell Summit, which is a very good thing.

I am already looking forward to attending this event next year.