To read the Green Pants Chronicles from the beginning, click here.

Act 1: Inception

BuzzBox – Our First Idea

The very first idea I played with had nothing to do with Windsor Circle. My thesis, in 2008-2009, was that smartphones were too expensive to gain wide adoption but that social media was taking over the world. I guess I was batting 500 on predictions. It was easier to believe then as the iPhone launched on June 29, 2007, and most of us considered ourselves lucky if we had a BlackBerry. WiFi was not ubiquitous, and 3G ruled the airwaves, and most of us had flip phones if we had anything more than a landline.

Simultaneously, pay phones were in steep decline and disappearing from the landscape, leaving in their wake millions (billions?) of dollars of hardwired infrastructure to every public place imaginable, from restaurants, to airports, to street corners. And no one was using that infrastructure!

So, the idea was to put an elegant touchscreen everywhere a payphone used to be. The user-friendly interface would be tied to social media sites, and allow users to post to Facebook or Twitter, or check email, or search for directions, in exchange for answering a few quick survey questions. This would allow brands and advertisers unparalleled first party research opportunities as demographic data based on location is well documented.

Killed by Truck Rolls

The net of it was the marketers loved the idea and VCs hated it. But the VCs didn’t hate the idea because of the cost of the hardware… we assumed that was going to be the issue. What killed the idea was the infamous “Truck Roll.” The hardware was a fixed cost, and one whose unit cost would come down with scale. However, every time a device went offline, or some drunk in a bar put her or his fist through a screen, we’d have to send a contracted service provider out to fix it. That scary, unknown, largely variable cost killed the concept. I spoke to some pretty high level RedBox management team members for perspective, but their footprint was less extensive that what I was imagining, and their units could be “hardened” in ways that didn’t limit the attractiveness of the user experience.

No More Playing Start Up

At the time, one of my most dynamic classmates from UNC Kenan-Flagler’s 2005 Full Time MBA program, Allison Philips, had joined up with Brad McGinity and me to investigate the idea. We were taking real steps to validate the concept (or invalidate it, as it turned out), but there was a point where the weight of the truck roll was looming large and we needed to make a decision about how to proceed as we were consuming valuable evening and weekend time as we were trying to figure it all out.

At the time (summer 2010), Chris Heivley and Dave Neal were underway with the Startup Factory at the American Underground, an accelerator and early stage investment fund. The call went out for applications for the next class of program participants. It would require me to quit my job, Brad to configure his second year of business school in a way that allowed him full time participation in our efforts, and Allison to move from DC to NC for at least the 12-week accelerator program. As I saw it, it’d be a good vehicle for forcing the conversation about whether or not we were serious about BuzzBox, as it would require real (and scary) life decisions.

As we explored the idea of filling out the application, the conversation had the intended consequence. We decided as a team to kill the idea, thinking that it did not have the right long term prospects to be worth the amount of sacrifice we were going to have to make. We were not ready to go from “Playing Startup” to committing, which in hindsight was a good thing.

“Call Me Back… I’ve Got the Next Idea!”

5 minutes later, I pinged Brad and said, “call me back… I’ve got the next idea!”

(Insert dramatic cliffhanger here so that you’ll come back and read the next post about how the idea that became Windsor Circle came to be!)