Timing is Everything: A long (but hopefully interesting) thread.

Here’s a personal story from the wild west days of the internet, about a pioneering company you’ve probably never heard of.

The year was 2000 and despite predictions to the contrary the world hadn’t ended...

So here I was, VP of Product at a Silicon Valley startup named Gator, a little known company that has the distinction of being the first mass consumer app, long before apps were a thing. I had crash landed at Gator via an acqui-hire of my own failed startup, a direct competitor.

It was a humbling experience. My company had built a better product but Gator had won the distribution game. It was my fault - I was a 27 y.o. first time old founder and Gator’s team was seasoned & had struck early internet gold in the search engine biz (remember Excite?).

Gator’s app was a browser plug-in that managed passwords, a feature now embedded in most browsers. At its peak Gator had *50 million MAU’s*, making it the most popular app of that era.

The Gator team essentially pioneered app install marketing. The company had raised $60M (a massive amount at the time) from top VCs *right before* the dot com bubble burst so we were able to squeeze publishers, buying online advertising for pennies on the dollar.

Those of you who are OG internet geeks will appreciate the clever (and slightly shady) app distribution mechanism we devised. At the time, web browsers would present a pop-up (from VeriSign) as a warning before plug-ins were installed.

We had observed through testing that about 7% of the time people would automatically click “Yes” on those popups (often not even knowing what they were installing).

Our clever idea (again, squeezing revenue-starved publishers) was to buy VeriSign pop-ups on a *CPM basis*.

This resulted in a cost-per-install of about *14 cents*. Whether they meant to install Gator or not, users generally liked the app (passwords are an age-old problem) and the company reached scale quickly.

What proved more controversial was our revenue model….

You know how you visit a website & then later when you’re on facebook or instagram you’ll see an ad for a related product? It’s a little creepy but these days all social platforms do it. Gator was the first company to do that kind of advertising at scale.

Our plug in monitored the websites you visited (all data was anonymous) and served related ads to support our free password software.

As we all know, this type of “retargeting” works very well - we were able to attract a roster of brand name advertisers...

...and generate 20-30 cents per month in ad revenue per active user (remember that it cost us only 14 cents to acquire a user).

It was a cash cow model, except for one thing...

Retargeting is commonplace now but at the turn of the century this was a highly controversial model and Gator was labeled by the media and consumer watchdogs as “spyware” (despite the fact that we didn’t collect or store PII).

The combination of our sneaky distribution tactics and being first to do retargeting ads was too much for the world to swallow. We had a huge PR problem that turned into scores of lawsuits.

Despite this, Gator reached $120M in revenue & had flipped profitable. The company filed an S-1 and but immediately had to pull it due to legal and PR backlash. We started losing advertisers. A large software company in Washington made a play to acquire Gator for a big number...

...then in a crafty move leaked the news to test the waters. More negative publicity & the buyer walked. Somewhere along the line I was “excused” from the company.

Ultimately Gator pivoted twice but it was too little too late.

So what’s the lesson here?

I think of Gator as a cautionary tale of *the importance of timing*. The difference between wild success and a complete write off is often very narrow. Here’s a company that was way ahead of its time, pioneering two models that became the foundation of many unicorns to come.

Under slightly different circumstances Gator could have been a unicorn. *But the timing was wrong.*

The silver lining for me was I left the company with “a very particular set of skills” that proved valuable in future ventures.

But at the time it was a hard lesson to swallow.