I am Not Easily Squished

I fall in love with wicked problems! I enjoy providing clarity to strategy, design, and engineering by keeping the “main thing the main thing” during a project’s journey.

When I’m not helping inspire product teams with my customer knowledge, I am telling stories and teaching people how to design podcasts and produce new media. Together, these skills turn me into a creative evangelist that enjoys being the optimistic member of the team.

From Concept to Prototype

TeamSnap Prototype

TeamSnap Prototype dashboard created to help coaches manage their teams (2006)

My first big web application success came when I was hired to build a prototype web-based application called TeamSnap. I was given only rough paper designs by a marketing agency out of Portland, Oregon, and asked to turn them into a real sports management application. Using PHP, Smarty Templates, PEAR, and MySQL I turned the paper version of TeamSnap into a working prototype of a web-based tool that coaches could use to manage their amateur teams, and organizers could use to manage their leagues.

The final prototype was delivered to the marketing agency with high praise and was key in their sale of application code to a third-party investor. Within 3-years, TeamSnap was transformed from a prototype application into the US$45-million Software-as-a-Service company (teamsnap.com) based in Boulder, Colorado. The current version of TeamSnap still maintains many of the features I built into the original prototype.

I have been focused on building web-based applications ever since my TeamSnap experience. Building something that grew into a successful company taught me how enjoyable developing Software-as-a-Service applications could be. Especially when I could work with others using a whiteboard, butcher-paper sketch pads, and paper-based demos to brainstorm functions, workflows, and features.

Startup Crash and Burn

‘Kites Rock! Unless you need a jet’ described PilotNorth’s positioning as a CMS and eCommerce software integrator (2008).

The desire to create new web-based applications led me to become the co-founder of PilotNorth, a web software company based in Northern Virginia, in 2008. As founder and the company’s CTO, I learned to balance business development with implementing enterprise CMS software and e-Commerce solutions for both commercial and government clients. Within our first three months of business, we had won a contract with the US Forest Service to change their public website from a static HTML site into a site controlled by a content management system.

Those first months of being part of a startup like PilotNorth were exciting. We had created over US$100,000 in potential revenue, formed a remotely-based, web development team, and invested heavily in supporting WordPress, osCommerce, and Openbravo as solid business solutions. However, founder in-fighting, cash flow disruptions, and a lack of formal agreements doomed PilotNorth before it was able to get its feet on the ground. Nothing teaches you about the difficulties that surround money, trust, and loyalty better than a company whose founders are not in alignment. It was a sad day when we had to shut PilotNorth’s doors after only 8-months of business.

Fortunately, it taught me a lifetime of business lessons that can only be understood through experience. Even though the fall of PilotNorth was a painful time in my career, I still miss the halcyon days that come with founding a startup.

Here Be Monsters

I love interesting and wicked problems and finding solutions that make software work better. That’s why I enjoy talking at conferences. It is my way of having to streamline an idea, test its validity, and gain instant feedback. Because if I cannot teach someone my solution then it isn’t a good solution. Fortunately, this process has pushed me out of my comfort zone into a new and rewarding career territory.

I started my experimentation with a very technical talk at a WordCamp event in Asheville, North Carolina in 2015. During this talk, I introduced the idea of using WordPress Multisite Design Patterns that encapsulated a number of scenarios where using a WP Multisite architecture can benefit an organization. From there I explored the number one problem that organizations experience when using WP Multisite — tight coupling of sites with an inability to separate these sites seamlessly.  The resulting MVP was a plugin called Jabberslicer that could split WP Multisites into individual WordPress instances. Unfortunately, it was unaccepted by WordPress.org due to its wicked complexity and networking dependencies. It was an idea before its time.

Surviving My Podwrecks

All my WordPress exploration lead me to find a way to share my ideas beyond blogging. That’s when I discovered podcasting! I took my creativity and talk experience to a whole new level by diving into the wicked problems created by developing, recording, and producing a podcast. In my haste to learn everything about podcasting, I made a ton of mistakes. My first podcast Merchants of Dirt started off with everything wrong: from the microphone selection to the audio editing.

However, in doing it wrong I learned all the ways to break it, tweak it, and ultimately fix it. This hard-fought journey helped create a new experimental platform: Gagglepod. Gagglepod started as a meetup (now renamed Virginia Podcasters’ Association or VAPODA) to give back to others what I had already learned about podcasting. After a year of using my meetup talks to test my understanding, ideas, and processes, I took my ideas on the road to speak at national podcasting conferences, be a guest on other podcasts, and become a voice within the independent podcasting community.

Becoming Not Easily Squished

I’ve now turned my focus to concept creation and investigating the principles behind podcast design and pre-production: all the soft things that have to happen BEFORE you buy a microphone. I’ve gone back to updating my creativity skills by learning principles over process, and have been heavily involved in supporting new podcasters that have become stuck by co-hosting Podwrecked with my good friend Timothy Kimo Brien. Together, we have smashed the myth that if you record it and they will listen in exposing how much pre-production work goes into knowing your audience and developing your content to meet their expectations.

I’ve become so fascinated with understanding what can be learned from traditional and new media design that I am doing extensive experimentations with different kinds of podcasting formats. This has led me to create my first audio drama called PAUSE for Dramatic Effect, and start a new weekly podcast about podcast design thinking called Not Easily Squished. Both have helped keep my skills sharp when it comes to creative trends and difficult podcast problems.

I continue to marvel at the benefits a healthy dose of good ‘ole fashion design thinking can have on any podcast and know that this is the aspect of podcasting I want to be known for: The Podcast Design Thinker that creates ideas that are Not Easily Squished!

Last modified: April 7, 2020

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