Check out my latest project, AnyFu, a site that makes it easy to hire proven technology experts for short-term screen-share sessions.

I began building a web-based version of PowerPoint called Preezo back in the Spring of 2005 after switching the direction of my angel-funded startup for the third time in less than a year. Prior to that I had been working on a web collaboration concept akin to JotSpot, but after awakening to the the potential of AJAX I was tempted to go after something a little more cutting edge. While I was partially lured by the siren song of a new technology, I also perceived what I felt was a singular startup opportunity.

The previous year Google and Yahoo (with the purchase of Oddpost) had replicated much of Microsoft Outlook's functionality and responsiveness with their new email services and it seemed pretty obvious to me that the rest of Microsoft Office would be challenged in much the same way. The only uncertainty was how long it would take before that happened. My feeling was that while Google and Yahoo were likely to move fairly quickly I could still get there first and if I did I would be perfectly positioned as an acquisition candidate. While that's not exactly how things played out, it seemed like a pretty solid bet to me at the time.

After working a full year and a half on Preezo I finally (and I mean finally) unveiled it to the public in October of 2006 at the Office 2.0 conference in San Francisco. While Yahoo had yet to demonstrate any interest in the the web office category, Google was moving full steam ahead with their Google Docs offering and at that time consisted of both a word processor (formerly Writely) and a spreadsheet (also an acquisition). The only piece that was conspicuously missing was a PowerPoint replacement, but once that was in place the Google productivity suite would be complete.

On the second day of the conference, the product manager for Google Docs, Jonathan Rochelle, stopped by my demo table along with an entourage of fresh-faced Googlers to see what Preezo was all about. I was caught a little off-guard at the timing as I was on the phone with my wife when they emerged from the crowd, but I remember hurriedly saying to her "I gotta go, Google is here." While that wouldn't normally be the kind of thing worth recounting, the reason I mention it is that upon hanging up Jonathan Rochelle repeated wryly and with a smile, "Yes, time to go. Google is here," and that pretty much set the tone.

After two days of giving presentations to interested attendees I had polished my five-minute demo to a fine sheen and to my relief the Google contingent appeared duly impressed. In fact, the first words out of Jonathan Rochelle's mouth at the completion of the demo was, "So, where have you been?" While I didn't have much of an answer to that question, based on the ensuing conversation it appeared that Preezo was just what Google was looking for. And as if it was all unfolding to some kind of script, Mike Arrington had just published a TechCrunch story that morning predicting that Preezo would be acquired in short order. Things were certainly looking good.

The remainder of the conversation went so well the whole matter appeared as if it was preordained and my confidence couldn't have been higher. Jonathan's plan was to get me up to the Googleplex as soon as possible to meet with the "Writely guys", however scheduling became complicated due to the fact that he and the spreadsheet team were based out of New York. After a few weeks of emails and phone calls attempting to coordinate the summit, Jonathan ultimately decided that the best way to move the process forward would be to go ahead and arrange for a phone call between myself and a director of engineering.

Since things would be moving beyond his direct sphere of influence, he gave me a few parting words of advice on navigating the acquisition process and wished me luck. About a month later I finally received a call from the director of engineering, David Glazer. The call ended up lasting only about twenty minutes and he spent most of the time explaining how Google worked as an organization and culture. The fact that he didn't reference Preezo or the acquisition process struck me as a little odd, but I figured that they just wanted to make sure Google would be a good fit for me. Overall, I thought the call went well, but since I didn't do much talking there wasn't a whole lot that I could have screwed up.

After that the communication fell silent. I resisted contacting Jonathan or David because I didn't want to appear too eager and I figured I was in a fairly strong position since they needed what I had and there didn't appear to be any other serious competitors in the space. Plus, I convinced myself that Preezo would appear only more valuable in the coming months as I continued to roll out a slew of advanced features like transitions, animations, diagramming and real-time collaboration. In fact, I had mentioned to Jonathan that in order to achieve pixel perfect text styles and bullet points I had decided to route around the built-in browser editing functionality by intercepting all key and mouse events and manipulating the DOM directly. This concept seemed to really intrigue him and I felt that if I could make it work (which I ultimately did) it would be an ace in the hole.

But the months rolled by and I heard nothing from Google until the following June when I read that they had acquired Zenter, a YCombinator startup working on the same problem. At that point my heart sank as it was obvious that the window of opportunity had closed and it wasn't a few months later that Google Presentations itself was released. While the Google version wasn't quite as powerful or polished as Preezo, being that it was free, solidly good enough and integrated into a complete productivity suite meant it was going to be very tough going for Preezo as a standalone product. To make matters worse, Yahoo and Microsoft had continued to abstain from the web office race, shunting any hopes that acquisition offers might be soon forthcoming.

A number of months later and shortly before the funding ran out I contacted Jonathan to see if Google might still have some interest in purchasing Preezo, but as expected they were no longer interested. While on the phone I took the opportunity to ask him the burning question of why I had never heard back from them in regards to the acquisition of Preezo. I had developed my own theory which was that since Google acquisitions were known to be primarily about talent and not technology, a one-man show like Preezo would represent distinctly less value and ultimately more risk for them than if it was, for example, a team of five engineers. However, according to Jonathan that wasn't the reason as at all. It was simply that they were so busy during that time that the deal just fell through the cracks.

Now I don't know if sending a few emails to Jonathan and David would have meant the difference between Preezo being acquired or not, but my guess is that it would have significantly increased the chances. Maybe other impediments to the sale would have arisen, but I have a hard time imagining what those might have been. While I learned a lot of lessons from my experience with Preezo, the one that I shouldn't have had to learn in the first place is to never let a line of communication go cold with a potential acquirer and especially if it's a large and very active corporation like Google.

As an aside, Google Docs announced this past May that they had implemented text editing without using the browser's editable HTML element and I've wondered ever since whether it was my conversation with Jonathon that provided the critical existence proof for the Google Docs team. No doubt this is a question which will remain unanswered.

Sign up for the Appignite beta, a tool that makes it possible to create data-driven web applications in minutes rather than months.
And follow me on Google+ because that's where all the action is.