Marissa & me: A love story in three parts

F. Scott Fitzgerald famously said, "There are no second acts in American lives." Had he met Marissa Mayer, he might have thought differently.

At one time she was America's geeky sweetheart, the golden girl software engineer who'd helped to build Google into a beast and would save Yahoo from itself. [1] That didn't go entirely as planned. For the last few years she's been co-founder of Sunshine, which makes a souped-up contacts manager app (also called Sunshine).

And, once upon a time, Marissa was my boss. [2]

In late 2013, which feels like a century ago, I was hired onto the staff of Yahoo Tech, one of a dozen or so "magazines" that Marissa decided to launch to take advantage of Yahoo's enormous audience. (To this day I don't know why she called them "magazines" and not what they actually were, which was websites. But I know she wanted them to be "Posh... like Vogue or Vanity Fair.")

She unveiled the "magazines" in a splashy keynote at CES in January 2014, along with a skit from SNL members Cecily Strong and Michael Che, and a cameo appearance by Katie Couric. It was the dawn of a brand new day for Yahoo. And she looked positively radiant up there on stage.

Marissa wanted to turn Yahoo into a mobile app company, which was a not-terrible idea. But in the meantime she needed something flashy and new to announce. Hence, the whole magazines concept.

While I was at Yahoo Marissa seemed strangely obsessed with organizing one's phone. She wanted to create some kind of overarching app that would streamline everything you did on your phone and make your life more manageable and perfect in every way. I'm not doing a good job summarizing this, because I had no friggin' idea what she was talking about at the time, and neither did anybody else at Yahoo.

But I guess Sunshine is what she was talking about.

Sunshine on my contacts makes me happy

Sunshine just released a new-ish version of itself, so I decided to try it out.

The first thing it did was ask to access the contacts list on my phone. Once it got done digesting all of them, it offered to reveal my "contacts personality." Here it is:

Sunshine has some nice, useful features. For example, if your contact info has changed and you want to send a message to everyone at once updating your current status (newly hired, recently fired, married, dead, etc), you can do that with a couple of clicks. That's something I really could have used when Yahoo laid me off in February 2016, and gave me exactly 12 hours notice to reach out to my 4,000 contacts before my corporate email account was shut off forever.

It identifies possible duplicate entries inside your contacts list and lets you merge them. It allows you to assign nicknames to different contacts. It lets you put all of your contact and major social account handles in one Rolodex-like card and share it with other Sunshiners. It scours your email conversations and suggests other folks to add to your list.

Sunshine is not exactly earth shattering, but it's very simple and practical. Is it worth spending $5 a month to use it full time as my phone's primary contacts app? I'm still debating that one.

Tumbling for fun and profit

I experienced many moments of comic absurdity in my brief time at Yahoo, which I hope to one day employ in a more creative endeavor. [3] But here's a classic: The decision to buy Tumblr for $1 billion+ in late 2013. At that time, Tumblr was mostly a visual diary for angsty 13-year-old girls [4]. When someone in a meeting asked Marissa what she wanted Tumblr for, she apparently said, "I want to use it for the magazines." Period, full stop.

Nobody bothered to ask how she wanted to use it. They just assumed she wanted to use it as the content management system for publications with hundreds of millions of readers, something it was never designed to be. No one had the temerity to inquire exactly what the hell she was thinking. [5]

Tumblr had an extremely limited toolset; for example, there was no way to create subheds or captions. The Tumblr development team and the Yahoo software engineers were located on different coasts and didn't talk to each other. Every so often, Tumblr would make some minor tweak to the code and break everything. The entire site would go down for a few hours, until someone on the west coast figured out what they'd done and fix it.

Yahoo then spent the next year and a half trying to build an intermediate solution that would translate from Tumblr to Yahoo's own publishing system. So you'd publish a story to Tumblr first, then it would be ingested by this intermediate thing, and then it would appear on the Yahoo Tech page.

What do you call it when a shitshow collides with a clusterfuck? I'm sure the Germans have a word for this. Yahoo (after being absorbed by Verizon) ended up selling Tumblr in 2019 for the price of a ham sandwich and a mocha venti latte. [6]

A final curtain call

As second (or third) acts go, moving from Google to Yahoo to Sunshine is like going from a starring role on Broadway to a bit part off-Broadway, and then to a community theater production of Cats.

Not that the woman needs more money. She was employee #20 at Google, after all, and bailed out of Yahoo with a very healthy golden parachute. [7] She probably has enough dosh to buy a small third world country (and then, streamline everyone's contacts). Still, it's a bit low profile for somebody who once merited a lavish spread in Vogue and was one of Glamour magazine's women of the year.

In other words, not exactly posh.

Do you Yahoo? Add your yodels below, and feel free to share this with your elderly relatives who still think Yahoo is the Internet.

[1] A Quixotic endeavor, to be sure, doomed to ultimately fail. I wrote about Yahoo's glorious beginning and ignominious end for Fast Company a few years ago. Still one of my best stories.

[2] Technically, my boss's boss. But who's counting?

[3] People used to ask me, 'What's it like working at Yahoo?' and I would respond, 'Have you seen the movie Brazil'? I got a lot of blank stares in response. (Has nobody seen that movie? It's friggin' brilliant. Go rent it now. I'll wait.)

[4] Also a rich source of adult erotica, mostly in the form of GIFs. I kid you not.

[5] Actually, one person did: Me. In an early all-hands meeting, about three months into the job, I submitted a question along the lines of "OK, we tried Tumblr, and it's not going so great. Can we get a real content management system, please?" That did not go over well.

[6] Actually $3 million. But close enough.

[7] Estimates range from $180 million to $260 million. My own tinfoil parachute was slightly less than that.