I am Wes Wilson. This is my site. This is how I got here.

This is my attempt at being open and honest about the experiences that have shaped my career. Minor successes, lessons learned, miscalculations... all of it. (Side note: I left off my personal milestones including marrying my wife, raising 3 kids and a cross-country move to Portland to name a few. If you really want to hear about any of that, I'm happy to share over a beverage.) There is real value in people being vulnerable, sharing their failures alongside their successes. As Yoda once said, “The greatest teacher, failure is.”

To early to tell

Momentum is strong. 2019 was a success and the future of open infrastructure is bright.

Open Infrastructure Summit
Open Infrastructure Summit

Open infrastructure starts with OpenStack (but it doesn't end there). For several years, the OpenStack Summit has expanded to welcoming dozens of open source communities including Ceph, Kubernetes, Docker, OPNFV and more. To better reflect the expansion of the communities the event serves, we rebranded the OpenStack Summit to the Open Infrastructure Summit. The name is long and "infrastructure" is tough to type, but the category is what we needed to capture. The first rebranded Summit was held in April in Denver, the second in November in Shanghai. Both were a resounding success!

Open Infrastructure Summit
Director of Marketing, OpenStack Foundation

Leading our badass marketing and events teams in communicating the benefits of open infrastructure through OpenStack, Kata Containers, Airship, StarlingX and Zuul, while defining OSF's place in the quickly evolving open source market. Level of success TBD.

Made this website

This site started off as a fun side project to get my hands further into serverless development. It turned into a writing exercise and deep dive into forgotten experiences. From the technical side, it's built off of a set of tools that we cobbled together for OSF pilot projects including Vuepress, Bulma, Buefy and Netlify CMS. Feel free to dig into the code, take what you want and send any ideas. Please don't giggle too loudly at all of the trial and error that's happening in my commits.

GitHub repo
What is OSF?
What is OSF?

Since being founded in 2012, the OpenStack Foundation has not had it's own identity. The foundation's sole purpose was to support the OpenStack software project. A unique identity would have countered that mission. As we expand OSF's role to fostering open infrastructure, including hosting other open source projects and building new OSS communities, we realize OSF needs an identity that differentiates the foundation from the software. Luckily, I get to work with tremendous writers, designers and developers that can bring the vision to life.

visit OSF.dev
Led our team in writing keynotes for the OpenStack Summit in Berlin for the first time
Led our team in writing keynotes for the OpenStack Summit in Berlin for the first time

Then rewrote and rewrote and rewrote and rewrote and rewrote. The rewrites were absolutely the right call, even though they happened the night before it went on stage in front of 2,500+. I had no idea I'd be on stage and would not have selected a hoodie to wear if I had known.

Watch the Day 1 keynote Watch the Day 2 keynote
Creative Director for my first Summit in Sydney, Australia
Creative Director for my first Summit in Sydney, Australia

I had the chance to work with some amazing designers like Joe Basnight, illustrators like Lola Scarpatti and event managers (looking at you FNtech.) We introduced the term “open infrastructure”, which would become OSF’s primary category moving forward. We move locations and reinvent the design theme for every Summit every 6 months. Each one is a labor of love and a lot of work. The team makes all the difference.

Expanded design team to accomodate new OSF projects and expanded mission

And by "expanded" I mean we went from one full time designer (me) to two, with additional support from freelance contractors. I have always been proud of what we've been able to accomplish with such a lean crew supporting OpenStack, OpenStack Foundation and now a handful of new pilot projects including Airship, Kata Containers, StarlingX and Zuul.

Lead Designer, OpenStack Foundation
Lead Designer, OpenStack Foundation

Working with arguably the greatest team ever assembled. For the first time in my career I was able to focus on one skillset... graphic design. UI, events, collateral, keynotes and more. I gave myself permission to fully trust my teammates and it paid off. My eyes were opened to how much impact the right team could have when combined with the right amount of autonomy. We were making an impact on hugely impactful organizations like CERN, Walmart, Nike, BMW, Blizzard Entertainment, Baidu and more.

Check out openstack.org
Freelance designer and consultant

Worked mostly with startups and Texas firms doing UI/UX work and the occasional logo design. I quicky discovered I’m not a great designer when I’m juggling clients. My head needs to be fully invested in something for me to be worth a crap. I need to be all in or not at all.

Co-Founder, Awesomatic

Think Slack before there was Slack. We posted a group chat concept on HackerNews and saw 2,000 signups overnight. Naively, we decided that was enough to quit our jobs and make a startup run. Investors told us there was "no market in chat", which we believed. We shifted from group chat to customer service without any real differentiation in the market. I experienced nearly one year of startup pains with two of the greatest people I know. Awesomatic, through the perseverance of one of our co-founders, made it into an incubator in Cincinati called Brandery. It fizzled out shortly after.

Read the Hacker News post
Mentor, Techstars Cloud
Mentor, Techstars Cloud

Techstars opened one of their signature startup incubator programs in San Antonio as a means to attract and create cloud-based startups. San Antonio became a temporary home to some exciting startups like Cloudability, Keen.io and Distil. At the time I was pretty tied into the local startup community, so I was asked to be a mentor. Imposter syndrome run wild!

Co-Founder, Pressable

Previously known as ZippKid (a name purchased through BrandStack), we provided Wordpress hosting in the hay day of Wordpress. I wasn't a co-founder in the traditional sense of the word. I came on to help the real founder, a close friend of mine. I didn’t yet see the value in allowing others to contribute to any success, so “staying in my lane” and working with a partner was tough. Thus my next startup attempt. Later, Pressable obtained significant investment from Automattic (creators of WordPress.) They stripped the team and are currently operating under new management.

Visit pressable.com
Sold BrandStack

At a loss. Techcrunch described it as us being “pulled from the deadpool” which wasn't entirely incorrect. It wasn't the outcome I had hoped for, but selling allowed me to get right with my customers and it took some major stress off of my shoulders. Unfortunately, I wasn't able to make my investors whole. I experienced unbeleiveable stress in the months leading to this date. Did you know that excess stress can trigger all sorts of auto-immune issues such as allopecia and shingles? It can. Take care of yourselves.

Read the TechCrunch article
I made Techcrunch, finally!
I made Techcrunch, finally!

Unfortunately, it wasn’t quite the article I was hoping for. I was unprepared for the security risks that come with a startup online marketplace. And remember, this was before SaSS services like Stripe that help combat credit card fraud. It went like this... One user hires themselves on UpStack using a stolen credit card, pretending to be separate users. They complete the project quickly, so we send the "designer" their payment. Owner of the credit card reports the stolen funds. Bank takes funds from us, even though we already paid the funds out to the designer. This happened in a short period of time to the tune of almost $100k, meaning I no longer have cash in the bank and the model wasn't strong enough to encourage further investment. Time to shut it down.

Read the TechCrunch article
Launched UpStack
Launched UpStack

Sister product to BrandStack, later named BrandStack Custom, that utilized our pool of 30k designers to create custom designs for clients through our project management portal. We even ate our own dog food and purchased the logo from a designer on BrandStack. While great in concept, UpStack's operational needs eventually led to our downfall.

See the original logo on BrandCrowd
Hired my first 3 employees

Designer, illustrator and writer. I micromanaged the hell out of them. I honestly had no idea how to manage people, so I started every day with a standup (which is very managerial), but then gave daily tasks. I gave no autonomy, which prevented them from helping me grow. They took it like champs. I still heart all of them and love following their success.

Raised seed capital
Raised seed capital

Raised seed round of funding from 2 founders of Rackspace. Stumbled into that relationship and didn't realize raising at that scale was possible until I met them. Part of the process included rebranding IncSpring to BrandStack, which I think was partially to see how well we worked together. Luckily it all worked out and with $250k in the bank, it was time to take my startup full time.

Fielded significant acquisition offers for IncSpring
Fielded significant acquisition offers for IncSpring

Getty Images was one suitor who was persistent, we chatted for months. I declined to move forward shortly after finalizing my seed round. iStockPhoto, a subsidiary of Getty, announced on their forums that they would be launching a competing service shortly after. Looking back, these could have also been fishing expeditions. Their competing service was not launched that I'm aware of, so they might have seen the writing on the wall before I did.

Read the article on TechCrunch See an embed of the original forum post
Spoke on my first SXSW panel
Spoke on my first SXSW panel

Got a little freaked out by the size of the crowd of 10s of people (shown in the pic) and nervously chatterted my way through the Q&A. I spoke mostly about the ups and downs of online markets, which is ironic since I was only in the "biz" for less than one year. Just look at how excited everyone was to hear us (yawning was a common reaction.) Side note, iPhone photos were not great back then.

Founder, IncSpring
Founder, IncSpring

IncSpring was a marketplace for unused logos and domain names. My office was my 2001 Ford Explorer. While working my full-time banking gig, I’d sit on my laptop outside of a nearby coffee shop with wifi that reached the parking lot. I designed the first front-end myself and worked with a firm to build the backend. They were a fantastic dev shop based in Ukraine. I never actually spoke to them, everything happened via Skype and email. I literally have never heard any of their voices to this day.

Vice President of Commercial Banking

At the time was the youngest VP in the bank. Regardless of the accomplishment, I quickly realized I was not cut out for banking. My job was to maintain a multi-million dollar commerical loan portfolio and find new businesses to loan money to. I was good at the maintaining, but not so much the sales part. I was much more interested in helping myself be an entrepreneur than someone else.

Credit Analyst, Commercial Banking

Somehow I was the person that determined if businesses could repay multi-million dollar loans, without successfully repaying any loans myself. I was able to peek behind the curtains of startups, profitable businesses and many more that wouldn’t make it. I tended to spend my time thinking about the business as a concept and what could be done to improve on their ideas. The bank thought my time was better served looking at the actual numbers, doing actual forecasting. Meanwhile, I was making so little that I had a second job working the register at a driving range.

Bachelors in Business Management and Entrepreneurship, University of TX at San Antonio
Bachelors in Business Management and Entrepreneurship, University of TX at San Antonio

My initial intention was to get a degree in marketing, but I changed majors when I realized how out of my league I was in Spanish 2. It's ironic that I couldn't tough out the marketing degree considering that's where my career ended up. Fortunately, UTSA just created the entrepreneurship track. I couldn't switch tracks fast enough, especially considering I was already writing business plans and dabbling in the worls of startups. That experience didn't always work in my favor, however. I once turned in my business plan for Fusion Boots as a final. I was certain I would ace that class. To my surprise, I received a "D" with a note saying I likely copied it from the internet. Go Runners!

Managed family construction business

In addition to experiencing my first “real” job (not counting skating rink DJ or stocker at the GAP), I learned to operate a roller, front-end loader, shovel and a broom. We had up to 13 employees at one time and worked on some pretty cool projects. For example, JKS Contracting helped to put a basement into the Alamo. That's right, Pee Wee Herman's Big Adventure would be inaccurate if retold today.

Founded Fusion Boots

I started my first company building custom speed skating boots. In additional to learning in-home manufacturing (building boots out of carbon fiber, leather, and other synthetic materials), I learned the true power of the internet, sourcing inventory from Italy and Japan via email. In a move that would become the lynchpin for my career, I also taught myself design and web development because I couldn’t afford to hire anyone experienced. Was it successful? Product quality never got to where it needed to be and college became a startup "distraction". I sold one single pair of boots for $700.

Graduate, Health Careers High School

I opted to attend a magnet school that only accepted a limited number of students. The goal was to use the "elite" status as a way to beef up the college resume. Unfortunately, schools don't get excted about less than stellar GPAs. Fortunately, I made great friends and wouldn't change a thing. Plus, I won "Best Legs" in my class... it's in the yearbook so it's legit. How could I not be happy?!

National Junior Olympic Speed Skating Champion
National Junior Olympic Speed Skating Champion

Not directly a career milestone, but it shaped my mindset. Gold medal in the 4000m two-man relay. We even set a national record (that would be beaten the following year.) Woohoo! In reality, the rest of the event was a disapointment. Why? That year, I trained at the US Olympic Training Center. I won or placed in every solo event I entered leading up to Nationals. I also became full of myself and slacked on training leading into Nationals. I didn't place in any individual events at Nationals.

Hello World

This isn't a personal timeline, but timelines have to start somewhere. Jumping ahead to things that I had a little more to do with.