Let’s Start a Ruckus

Kyle Bondo – Creative Strategist, Product Manager, Podcaster, and Speaker

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 niche audiences has a podcast producer and host. Together, these skills turn me into an internal evangelist that keep teams aligned, optimistic, and practical.

From Concept to Customers

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.

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, and if forced me to go in-house for a time, I still miss the halcyon days of PilotNorth’s founding.

There Be Dragons Here

Monsters of WordPress

Monsters of WordPress was created to support my interest in WordPress Multisite patterns and plugin development (2015).

I love telling stories and teaching niche audiences interesting ways to look at wicked problems. That’s why I find talking at conferences is a perfect way to streamline an idea, test its validity, and gain instant feedback. Sometimes the crazier the talk, the better the feedback!

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.

Merchants of Dirt

Kyle Bondo recording an episode of Merchants of Dirt, a podcast that teaches Race Directors how to build better races (2018).

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 to give back to others what I had already learned about podcasting. But after a year of using my talks to test my understanding, ideas, and processes, I moved out from local talks to share my ideas at national podcasting conferences.

Good Stories Told Well

Kyle Bondo at MAPCON 2018

Kyle Bondo at MAPCON 2018 presenting a talk on podcast show design principles (2018).

I’ve now turned my focus back to building Software-as-a-Service. I’ve gone back to updating my programming skills by learning Node.js, and have been heavily involved in support Enterprise migrations of on-site applications into Amazon AWS environments. The challenge of the lift-and-shift fallacy is in learning how much the customer requirements have changed from when the application was first created to now.

I love how cloud migrations are not simple and enjoy the complexity that comes with figuring out how wicked moving code from one location to another can be. There is nothing like redesigning over-complicated parts of software systems and filling the gaps that stop it from breaking the same way again. I’ve really become fascinated with understanding what can be learned from fail-fast and post-incident experimentation. It not only has allowed me to see how a service can be improved but allowed me to learn something new every day.

Who knows what tomorrow’s wicked problem will bring me. Hopefully, it will be something I can use to start another ruckus!

Last modified: August 19, 2019

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