Shapiro - Hot seat : the startup CEO guidebook

• 2015-05-06: First Release

I became the CEO of my first startup in an elevator. I didnt seize the reins of power in a bloodless coup. There was no passionate discussion or debate. I wasnt even planning to discuss the topic when it happened. My cofounder merely informed me that we were being stupid as the doors were about to open, and I was going to be the CEO from that moment forward.

When Charles and I first decided to found Ontela, we were unclear about who exactly was going to do what. My background was as a program manager and my cofounders was as a developer. Neither of us had ever managed more than a handful of people. So we decided on what we thought was a perfect compromise: I would be the President, and Charles would be CEO.

Needless to say, neither one of us had any idea how to do these jobs.

But from the start, we had a ridiculous amount of work to do. We knew little about startupsId worked at one, but not as a founder; Charles had been a part of ), and other conundrums of startup life to solve.

Charles was an accomplished software developer. I was a marginally competent software dabbler. So I did design, recruiting, pitching, fundraising, business plan writing, financial modeling, and many of the aforementioned odds and ends. I also managed the output of a motley assortment of a half-dozen developers in various far-off lands, who hadfor a total cost of less than $500built our first proof-of-concept prototype, and were continuing to maintain it while Charles worked on doing it the Right Way" (i.e. something marginally more scalable than a few shell scripts and a dodgy shared FTP server located in an indeterminate part of Southeast Asia).

We continued in this manner for a while, spending nights and weekends banging away on the nascent project. And after a few months, we decided to double down on our ignorance: we quit our jobs to work on Ontela full time. As soon as that die was cast, I began to sink more and more energy into fundraising. And it was early in February of 2006 when our fateful elevator ride occurred.

We were in the lobby of the Millennium Tower in downtown Seattle, WA, just north of the historical district of Pioneer Square, where we would eventually found our company. Its just one street south that the century-old cobblestones and purple glass sidewalks appear, but the Millennium Tower was clearly on the modern side of the divide.

We passed muster with the lobby guardian, wearing our finest khaki slacks and button-up shirtsthe semi-casual entrepreneurs standard-issue uniform. We stepped into the elevator, which quietly streaked to the buildings top floor.

My ears were still popping when Charles turned to me and gave me an intent look. Hey Dan... when they ask what our jobs are, youre the CEO and President. Im the CTO. OK?

Ding. The doors swung open. I furrowed my brow and opined on this unexpected development. Um. Huh?

Charles stepped into the gap and the elevator doors banged on his foot. Were deluding ourselves. Youre the CEO. Youre doing the fundraising, the legal stuff. Youre the face of the company. Youre selling the vision. Im building it. Youre the CEO, Im the CTO. Then he stepped out. I jumped after him as the doors slid closed, narrowly missing me on the way. We walked up to the receptionist and introduced ourselves. And thats how I received the qualifications, training, and authority to be the CEO of Ontela.

Needless to say, I had no idea what I was doing.